CA2635318A1 - Triterpenequinone and triterpenephenol derivatives and their application for the treatment of tumors and parasitic diseases - Google Patents

Triterpenequinone and triterpenephenol derivatives and their application for the treatment of tumors and parasitic diseases Download PDF

Info

Publication number
CA2635318A1
CA2635318A1 CA002635318A CA2635318A CA2635318A1 CA 2635318 A1 CA2635318 A1 CA 2635318A1 CA 002635318 A CA002635318 A CA 002635318A CA 2635318 A CA2635318 A CA 2635318A CA 2635318 A1 CA2635318 A1 CA 2635318A1
Authority
CA
Canada
Prior art keywords
substituted
alkyl
group
independently hydrogen
hydroxyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA002635318A
Other languages
French (fr)
Inventor
Juan Carlos Lacal Sanjuan
Ana Ramirez De Molina
Monica Banez Coronel
Angel Gutierrez Ravelo
Ana Estevez Braun
Dulce Yazmin Mesa Siverio
Elisa Perez Sacau
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Consejo Superior de Investigaciones Cientificas CSIC
Universidad de La Laguna
Original Assignee
Consejo Superior De Investigaciones Cientificas
Universidad De La Laguna
Juan Carlos Lacal Sanjuan
Ana Ramirez De Molina
Monica Banez Coronel
Angel Gutierrez Ravelo
Ana Estevez Braun
Dulce Yazmin Mesa Siverio
Elisa Perez Sacau
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Consejo Superior De Investigaciones Cientificas, Universidad De La Laguna, Juan Carlos Lacal Sanjuan, Ana Ramirez De Molina, Monica Banez Coronel, Angel Gutierrez Ravelo, Ana Estevez Braun, Dulce Yazmin Mesa Siverio, Elisa Perez Sacau filed Critical Consejo Superior De Investigaciones Cientificas
Publication of CA2635318A1 publication Critical patent/CA2635318A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
    • C07C49/727—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

The invention relates to triterpenequinone and triterpenephenol derivatives, their pharmaceutically acceptable 5 salts, prodrugs, solvates or stereoisomers as selective blocking agents of the choline kinase enzyme, pharmaceutical compositions containing them and their use in the treatment of tumors and parasitic diseases or diseases caused by viruses, bacteria or fungi.

Description

TRITERPENEQUINONE AND TRITERPENEPHENOL DERIVATIVES AND THEIR
APPLICATION FOR THE TREATMENT OF TUMORS AND PARASITIC DISEASES
FIELD OF THE INVENTION
The invention generally relates to triterpenequinone and triterpenephenol derivatives blocking the biosynthesis of phosphorylcholine by means of the selective blocking of the choline kinase enzyme in tumor cells or in cells affected by parasitic infection, and which are consequently applicable in the treatment of tumors and parasitic diseases or diseases caused by viruses, bacteria and fungi in animals, including human beings, as well as to a method for preparing the compounds of the invention.

BACKGROUND OF THE INVENTION
Choline kinase is the first enzyme of the Kennedy pathway or the phospatidylcholine (PC) synthesis pathway, and it phosphorylates choline to phosphorylcholine (PCho) using adenosine 5'-triphosphate (ATP) as a phosphate group donor. Ras genes form a family of the so-called oncogenes which have been widely studied since they are activated in 25-30% of all human tumors and in several of them in 90%. Ras proteins have an important role in the transmission of intracellular signals due to their involvement in the regulation of cell proliferation, terminal differentiation and senescence. The transformation mediated by different oncogenes, among which the ras oncogenes stand out, induces high choline kinase activity levels, resulting in an abnormal increase in the intracellular levels of its product, PCho. Complementary facts support the role of ChoK
in the generation of human tumors, as studies using nuclear magnetic resonance (NMR) techniques have shown high PCho levels in human tumor tissues with respect to normal tissues including breast, colon, lung and prostate tumors, among others. It is common knowledge that ras is one of the most deeply studied oncogenes in human carcinogenesis and that ChoK inhibition has been shown to be a new and effective antitumor strategy in cells transformed by oncogenes. These first observations were later extrapolated in vivo in nude mice.
In view of this data, the design of compounds directly affecting choline kinase activity or the enzyme activated by phosphorylcholine in an individual or combined manner would allow the development of effective antitumor therapies.
In this sense, the research on ChoK inhibitors has identified Hemicholinium-3 (HC-3) as a relatively potent and selective blocking agent [Cuadrado A., Carnero A., Dolfi F., Jimenez B. and Lacal J.C. Oncogene 8, 2959-2968 (1993); Jimenez B., del Peso L., Montaner S., Esteve P. and Lacal J.C. J. Cell Biochem. 57, 141-149 (1995); Hernandez-Alcoceba, R., Saniger, L., Campos, J., Nunez, M. C., Khaless, F., Gallo, M. A., Espinosa, A., Lacal, J. C. Oncogene, 15, 2289-2301 (1997)]. This choline homologue with a biphenyl structure has been used for designing new antitumor drugs, nevertheless, due to the fact that HC-3 is a potent respiratory paralyzing agent, it is not a good candidate for its use in clinical practice. The synthesis of some derivatives has been based on structural modifications of HC-3 improving the inhibitory activity of the ChoK enzyme and partly eliminating its toxic effects.
Bisquaternized symmetric compounds derived from pyridinium have also been used and their ability to inhibit PCho production in entire cells has been evaluated (W098/05644) . However, these derivatives have high toxicity levels limiting their extended therapeutic application.
On the other hand, it is known that the compounds called celastrol and pristimerin, formed by a pentacyclic triterpene structure, induce apoptosis, said activity having been proved in human models with leukemia [Nagase, M., Oto, J., Sugiyama, S., Yube, K., Takaishi, and Sakato, N., Biosci. Biotechnol. Biochem 67, 1883 (2003)]. Nevertheless, these compounds show a serious toxicity at cell level which makes their development as useful drugs in the treatment of tumor conditions impossible. In this sense, application US 2004/0220267 describes celastrol and pristimerin derivatives which allow improving the toxicity problem.
Nevertheless, there is a great need to develop compounds that provide a high inhibitory activity of the ChoK enzyme for the purpose of allowing their use for the treatment of tumors, while at the same time they considerably reduce their toxicity against compounds of the state of the art.
BRIEF DESCRIPTION OF THE INVENTION

After laborious research, the authors of the present invention have found that certain modifications in the structure of the previously described compounds celastrol and pristimerin allow providing compounds acting as blocking agents of the biosynthesis of phosphorylcholine by means of the selective blocking of the choline kinase (ChoK) enzyme and which have shown to be a new and effective antitumor strategy in human tumor cells.
Thus, in one aspect the present invention relates to the use of a compound of formula (I):
R:o Rg R~~
,,\\\R8 R12i Rs R
a HsC R
R, R2 (I) where:
Rl, R2, R3, R4, R5, R6, R7 , R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; an OCOR group, where R is (CH2) 2COOH or (CH2) 2CO2CH2CH3; or each pair can form a(C=0) group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(R14) (R ) amino, where RI4 and R' are independently hydrogen or a Cl-Clz alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group;
the bond ------ means a double bond or a single bond;
and where the tricyclic structure is selected from the following structures:
R14 R13 R14 R13 R14 Ris R a"" Rtr;Rwu'~' 0 RzoO RzoO

R17 R1;
R,,O R,,O R,,)O Rz3 Ria Ria R21 R22 Rje, R21 (a) (b) (c) Ri3 Ria Ris R1a Ris Ri5 R15 RR1~RzRiS
Rza Rz5 CH ;
R20 CH, R R

zozoRz~"0 Rzo ,,,. Rzo HRj~' R

R,~' Rzs Rzs Rzs RRi RIe Rz1 RI e" R18 R21 Rip, Rz, (d) (e) (f) where:

R13, R14, R15, R16, R21, R22 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted Cl-Clz alkyl;
substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-Clz alkyl group; an OCOR III group, where R III is (CH2) 2COOH or (CH2) 2CO2CH2CH3; or each pair can form a(C=0) group together with the carbon to which they are attached or each pair can form a (C=O) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
5 R18 and R18, are independently hydrogen; hydroxyl; halogen; Cl-C12 alkyl; C6-Clo aryl; CORIX (where RIX is hydrogen; hydroxyl; Cl-C12 alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12 alcoxyl); or trifluoromethyl;
R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen;
or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof, in the manufacture of a medicament for the treatment and/or prevention of a ChoK
mediated disease or condition.
In another aspect, the present invention refers to the use of a compound of formula (II) :

R
s \\\Ro :17 (II) where:

Rlr R2, R3, R4, R5, R6r R9r Rlor Rllr R1zr R13r R14r R15r R16r R17r Rl8r R19 and R20 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(Rxv) (Rxvz) amino group, where Rxv and Rxvl are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a carboxyl (C=O) group together with the carbon to which they are attached;
R7 and R8 are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a CORxvII group (where Rxvzz is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(Rxvzzz) (Rxzx) amino, where RxvIII and Rxlx are independently hydrogen or a Cl-C12 alkyl group) ; a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10) ; or together form a methylene group, R21 and R24 are independently substituted or non-substituted Cl-C12 alkyl; a CORxx group (where Rxx is hydrogen; hydroxyl;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxz) (Rxxzz) amino, where Rxxl and Rxxzz are independently hydrogen or a Cl-C12 alkyl group); a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl;

R22 and R23 are:

- hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORxxIII group (where RxxIII is hydrogen; hydroxyl;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxzv) (Rxxv) amino, where Rxxiv and Rxxv are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the para position with respect to R20; or OR22' and OR23' respectively, where R22' and R23' are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORxxvz group (where Rxxvz is hydrogen; hydroxyl;

substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxvzz) (Rxxvzzz) amino, where Rxxviz and Rxxvzzz are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the meta position with respect to R20=
or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof, in the manufacture of a medicament for the treatment and/or prevention of a ChoK
mediated disease or condition.
In a particular embodiment, the disease or condition is cancer. In another particular embodiment the disease is a parasitic disease. In another particular embodiment the disease is a bacterial disease. Finally, in another particular embodiment the disease is a fungal disease.
In another aspect the present invention relates to compounds of general formula (I):
Rlo Ro R~~
,\\\R8 R12i Rs R
a ) H3C R~
h3 R, R2 (I) where:

Rl, R2, R3, R4, R5, R6, R7, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; an OCOR group, where R is (CH2) 2COOH or (CH2) 2CO2CH2CH3; or each pair can form a(C=0) group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Cl2 alkyl; substituted or non-substituted C6-Clo aryl; O-Cl-C12 alkyl;
or N(R14) (R ) amino, where RI4 and R are independently hydrogen or a Cl-Clz alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group;
the bond ------ means a double bond or a single bond;
and where the tricyclic structure is selected from the following structures:

R14 Ris R14 R13 Riz R1z R RI s R,5 r i6 R R ' R \ \ õ =
0 RzzO R20O
R1;

R zO R1eO R,,O Rz., R18 Ria R21 R22 Rie R21 (a) (b) (c) Ris R14 Ris Ria Ris Ri, R~5 RRGim,,, R,5 Rza Rz~CH Rza CH;
RzCi' R20 Rz*R' R20 \~Rzo ' '~ CH Rzo , RI,' Rl~' RRRz Rz3 Rzs 19 R1e Rz1 R1e' R,e 21 RieRie Rz, (d) (e) (f) where:

R13, R14, R15, R16, R21, R22 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted Cl-Clz alkyl;
substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-Clz alkyl group; an OCOR III group, where R III is (CH2) 2COOH or (CH2) 2CO2CH2CH3; or each pair can form a(C=0) group together with the carbon to which they are attached or each pair can form a (C=O) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
R18 and R18, are independently hydrogen; hydroxyl; halogen; Cl-C12 alkyl; C6-Clo aryl; CORIX (where RIX is hydrogen; hydroxyl; Cl-C12 alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12 alcoxyl) or trifluoromethyl;
R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl- ]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen;

or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof, with the following provisos:

- when the tricyclic structure is (a) then the compound of formula (I) is not:
- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid;

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3,10-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3-Hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 3,9-Dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-5 7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;
- 3,7,9-Trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

10 - 14-Bromo-3,7,9-trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- Succinic acid mono-(10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl) ester;

- Succinic acid ethyl ester 10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl ester;

- Acetic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dodecanoic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dimethyl-carbamic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Nicotinic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;
- 3,10-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester.

- when the tricyclic structure is (b) and R19 and R20 are independently hydrogen or an acyl group, then:

- R5 is hydroxyl; or - R21 and R22 form a C=O group together with the carbon to which they are attached and Rlo is not COOH.

- when the tricyclic structure is (c) and R19 and R20 are both CH3, then R15 and R16 do not form a C=O group together with the carbon to which they are attached.

In another aspect, the invention relates to a compound of formula (II):

:::1 Rl9 R16 R15 (II) where:

Rlr R2, R3, R4, R51 R61 R9r Rlor Rllr R12r R13r R14r R15r R16r Rl7r Rlar R19 and R20 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(Rxv) (Rxvz) amino group, where RX4 and RX41 are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a carboxyl (C=O) group together with the carbon to which they are attached;
R7 and R8 are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a CORxvII group (where Rxvzz is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(Rxvzzz) (Rxzx) amino, where RxvIII and Rxlx are independently hydrogen or a Cl-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10) ; or together form a methylene group, R21 and R24 are independently substituted or non-substituted Cl-C12 alkyl; a CORxx group (where Rxx is hydrogen; hydroxyl;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxz) (Rxxzz) amino, where Rxxl and Rxxzz are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl;

R22 and R23 are:

- hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORxxIII group (where RxxIII is hydrogen; hydroxyl;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxzv) (Rxxv) amino, where Rxxzv and Rxxv are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the para position with respect to R20; or - OR22' and OR23' respectively, where R22' and R23' are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORxxvz group (where Rxxvz is hydrogen; hydroxyl;

substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxvzz) (Rxxvzzz) amino, where Rxxviz and Rxxvzzz are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the meta position with respect to Rzo=
or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof.

In another aspect, the invention is directed to a pharmaceutical composition comprising a compound of formula (I), or a compound of formula (II), or mixtures thereof, or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof together with a pharmaceutically acceptable carrier, adjuvant or vehicle, for the administration to a patient.

DETAILED DESCRIPTION OF THE INVENTION
One object of the present invention is the use of a compound of formula (I) Rlo Ro Rll Ra ,o\R12i ,~~11nRs ""Ra NsC R3 R, R2 (I) where:

Rl, R2, R3, R4, R5, R6, R,, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; an OCOR group, where R is (CH2) 2COOH or (CH2) 2CO2CH2CH3; or each pair can form a(C=0) group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Cl2 alkyl; substituted or non-substituted C6-Clo aryl; O-Cl-C12 alkyl;
or N(R14) (R ) amino, where RI4 and R are independently hydrogen or a Cl-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group;
the bond ------ means a double bond or a single bond;
and where the tricyclic structure is selected from the following structures:

R14 R13 R14 R13 R14 Rjs Ris RIs R~5 Rr~~ ,,,,. R o ,,,, R ~~",,,.
w 0 RzzO R20O
R17 R;

R ,0 R1z0 Rlc) O r R R18 R1o R21 R22 R18 R21 (a) (b) (c) Ri R 14 Ris R 14 Ris R15 RR16RR~5 Rza Rz~CH za CH, Rzo Rz0 Rz0 ~
R2 ~~~~,,,. R20 "\~,,,,. CH Rzo """.~
, R~~~ Rlc' Rlc' R2, Rzs Rzs Ri Ri Ri Rje R21 R18' R~e R21 Rje~ ~R1e R21 (d) (e) (f) where:
R13f R14f R15f R16, R21, R22 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-Clz alkyl group; an OCOR III group, where R III is (CH2) 2COOH or (CH2) 2CO2CH2CH3; or each pair can form a (C=O) group together with the carbon to which they are attached or each pair can form a (C=O) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
R18 and R18, are independently hydrogen; hydroxyl; halogen; Cl-Clz 5 alkyl; C6-Clo aryl; CORIX (where RIX is hydrogen; hydroxyl; Cl-Clz alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12 alcoxyl); or trifluoromethyl;
R19r R19,, R20 and R20, are independently hydrogen; substituted or 10 non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-O- (Cl-C12) alkyl-] n group (where n is 15 comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen;

or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof, in the manufacture of a medicament for the treatment and/or prevention of a ChoK
mediated disease or condition.
In a particular embodiment of the invention, the compound of formula (I) used in the prevention and/or treatment of a ChoK
mediated disease or condition is a compound of formula (Ia):
Rio Ry Rll opRa Ris R~a~ CH3 ~
Ris /11, = -111iiRa H CH3Rs O ~10Ra R H3C '~ Rs R i R2 R1gO

Ria (Ia) where Rl, R2, R3, R4, R5, R6, R,, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; an OCOR group, where R is (CH2) 2COOH or (CH2) 2CO2CH2CH3; or each pair can form a(C=0) group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(R14) (R ) amino, where RI4 and R are independently hydrogen or a Cl-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R14, R15 and R16 are independently hydrogen; hydroxyl;
halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-C12 alkyl group; an OCOR III group, where R III is (CH2) 2COOH or (CH2) 2CO2CH2CH3; or each pair can form a(C=0) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
R18 is hydrogen; hydroxyl; halogen; Cl-C12 alkyl; C6-Clo aryl; CORIX
(where RIX is hydrogen; hydroxyl; Cl-C12 alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12alcoxyl); or trifluoromethyl;
R19 is hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3) ;
or trifluoromethyl; and the bond ------ means a double bond or a single bond.
In a preferred embodiment, the compounds of formula (Ia) used in the invention comprise a substructure having the following formula (Ia'):
CH,, R12/,,, R7 CH,, O ~

CH ; CH,, ~ ~

CH,, (Ia') where R5 is hydroxyl or a OCOR group where R is (CH2) 2COOH or (CH2) 2CO2CH2CH3;
R7 and R8 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R' )(R" ) amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R12 is independently hydrogen or a halogen; and R19 is hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3) ;
or trifluoromethyl; and the bond ------ means a double bond or a single bond.

Particular examples of this substructure (Ia') are:
- 3,9-Dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;
- Acetic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl propionic acid ester (C1);

- Dodecanoic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dimethyl-carbamic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Nicotinic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- 4-bromo-(9-hydroxy-6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl) benzoic acid ester (C2) ;

- 14-Bromo-3,7,9-trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 12-bromo-9-hydroxy-6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl dimethyl-carbamic acid ester (C4);

- 4-bromo-(12-bromo-9-hydroxy-6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl) benzoic acid ester (C5);

- 12-bromo-3,9-dihydroxy-6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione (C3);

- 3,9,10-trihydroxy-6b,8a,11,12b,14a-hexamethyl-7,8,8a,9,10,11,12,12a,12b,13,14,14a-dodecahydro-6bH-picene-2-one (C6);

- Succinic acid mono-(10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl) ester;

- Succinic acid ethyl ester 10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl ester.
In another preferred embodiment, the compounds of formula (Ia) used in the present invention comprise a substructure having the following formula (Ia "):
CH;

C_H3 CH;
O

CH,, CH,, H;
(Ia" ) where:
R7 and R8 are independently hydrogen, hydroxyl, halogen, substituted or non-substituted Cl-C12 alkyl, substituted or non-substituted C6-Clo aryl, a N(R' )(R" ) amino group, where R' and R'' are independently hydrogen or a Cl-C12 alkyl group, or each pair can form a(C=0) group together with the carbon to which they are attached;
R15 is hydrogen or halogen;
R19 is hydrogen, substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3) ;
or trifluoromethyl; and the bond ------ means a double bond or a single bond.
Particular examples of this substructure (Ia'') are:

-14-bromo-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione (C7);

-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-5 2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl acetic acid ester (C8);

-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl nicotinic acid ester (C9);

10 -3,10-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,9,10,11,12,12a,12b,13,14,14a-dodecahydro-6bH-picene-2-one (C10);

-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,12a,12b,13,14,14a-octahydro-6bH,9H-picene-2,10-15 dione (C11) .

In another preferred embodiment, the compounds of formula (Ia) used in the present invention comprise a substructure having the following formula (Ia "'):
H;C ,COOCH;

CH~

O ~

CH~ CH;
~ ~ J
20 H;
(Ia,,,) where:
R7 is hydrogen, hydroxyl, halogen, substituted or non-substituted Cl-C12 alkyl, substituted or non-substituted C6-Clo aryl, or a N(R' )(R" ) amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; and R19 is substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl.

Particular examples of this substructure (Ia "') are:
- 10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3,10-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C12);

- 2,4a,6a,9,12b,14a-hexamethyl-11-oxo-10-propionyloxy-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C13);

- 10-dimethylcarbamoyloxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C14).

In another particular embodiment of the invention, the compound of formula (I) used in the prevention and/or treatment of a ChoK mediated disease or condition is a compound of formula (Ib) :
Rio Ro R i i 12m1,,, R
R~qR~~ CH3 R7 R 16\"",,,, R200 ,,,,/R
a 1 R~~ NsC R3 RioO R23 (Ib) where:

Rl, R2, R3, R4, R5, R6, R7, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ' ) amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(R14) (R ) amino, where RI4 and R' are independently hydrogen or a Cl-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R14, R15, R16, R21, R22 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-Clz alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
R18 is hydrogen; hydroxyl; halogen; Cl-C12 alkyl; C6-Clo aryl; CORIX
(where RIX is hydrogen; hydroxyl; Cl-C12 alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-Cl2alcoxyl); or trifluoromethyl;
R19 and R20 are independently hydrogen, substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen;
hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl; and the bond ------ means a double bond or a single bond.

In a preferred embodiment, the compounds of formula (Ib) used in the present invention comprise a substructure having the following formula (Ib'):
O

OH
CH;

CH; CH3 CH; OH
(Ib') where:
R19 and R20 are independently substituted or non-substituted Cl-C12 alkyl; a CORxII group (where RxII is hydrogen; hydroxyl;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(RxIII) (RxI ) amino, where RxIII and Rxzv are independently hydrogen or a Cl-C12 alkyl group); a[(Cl-C12) alkyl-O- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl.

A particular example of this substructure (Ib') is 4-nitro-(3-dimethylcarbamoyloxy-5,9-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-10-oxo-5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-2-yl) benzoic acid ester (C15).
In another preferred embodiment, the compounds of formula (Ib) comprise a substructure having the following formula (Ib"):
H3COOC CH;
H~

CH;
HO I CH~ CH;

R190 R2s (Ib" ) where:
R18 is hydrogen; hydroxyl; halogen; Cl-C12 alkyl; C6-Clo aryl; CORIX
(where RIX is hydrogen; hydroxyl; Cl-C12 alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12alcoxyl); or trifluoromethyl;
R19 is hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3) ;
or trifluoromethyl;
R23 is hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R 1 and R411 are independently hydrogen or a Cl-Cl2alkyl group.

Particular examples of this substructure (Ib'') are:

- 7,10,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester (F16);

- 9-formyl-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C17);

- 11-hydroxy-10-(2-methoxy-ethoxymethoxy)-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C18).

In another particular embodiment of the invention, the compound of formula (I) used in the prevention and/or treatment of a ChoK mediated disease or condition is a compound of formula (Ic) :

Rlo Ro R ll R1,,~111\ Ra 4 R1 H~ R7 C
R15 = ., Rs R 16\" " H CHRS

R200 ""'/iRa R, R2 (Ic) where:

5 Rl, R2, R3, R4, R5, R6, R7, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) 10 group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
15 or N(R14) (R ) amino, where RI4 and R are independently hydrogen or a Cl-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group;

R13, R14, R15, R16, R21 and R23 are independently hydrogen;
20 hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-Clz alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
25 R18 is hydrogen; hydroxyl; halogen; Cl-C12 alkyl; C6-Clo aryl; CORIX
(where RIX is hydrogen; hydroxyl; Cl-C12 alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-Cl2alcoxyl); or trifluoromethyl;
R19 and R20 are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen;
hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl- ]n group (where n is comprised between 1 and 3); or trifluoromethyl; and the bond ------ means a double bond or a single bond.

In an embodiment, the compounds of formula (Ic) used in the present invention comprise a substructure having the following formula (Ic'):

(Ic') where:
R19 and R20 are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen;
hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3) or trifluoromethyl; and the bond ------ means a double bond or a single bond.
Particular examples of this substructure (Ic') are:
- 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-1,4,4a,5,6,6a,13,14,14a,14b-decahydro-2H-picene-3-one (C19) ;
- 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-4a,5,6,6a,13,14,14a,14b-octahydro-4H-picene-3-one (C20).
In another preferred embodiment, the compounds of formula (Ic) used in the present invention comprise a substructure having the following formula (Ic"):
H3 ,C --COOCH~
CH~

CH;

(Ic" ) where:
R19 and R20 are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen;
hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl- ]n group (where n is comprised between 1 and 3); or trifluoromethyl.
A particular example of this substructure (Ic") is 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-1,2,3,4,4a,5,6,6a,13,14,14a,14b-dodecahydro-picene-2-carboxylic acid methyl ester.

In another particular embodiment of the invention, the compound of formula (I) used in the prevention and/or treatment of a ChoK mediated disease or condition is a compound of formula (Id) :
Rlo Ro R12m,,,, Ra R13 CH~ R~
R15 nRs R2o R20 ;C R3 R, R2 R1o' ; R2s Rjo (Id) where:

Rl, R2, R3, R4, R5, R6, R7, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Cl2 alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(R14) (R ) amino, where RI4 and R are independently hydrogen or a Cl-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R15, R21 and R23 are independently hydrogen; hydroxyl;
halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R18 is hydrogen; hydroxyl; halogen; Cl-C12 alkyl; C6-Clo aryl; CORIX
(where RIX is hydrogen; hydroxyl; Cl-C12 alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-Cl2alcoxyl); or trifluoromethyl;
R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl- ]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen; and the bond ------ means a double bond or a single bond.

In a preferred embodiment, the compounds of formula (Id) used in the present invention comprise a substructure having the following formula (Id'):

O
R
R ~ R%~ 2 CH~

R20' R20ii~ õ CH3 Rlg' \; ~ R~~

(Id') where:
R5 and R6 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R' )(R" ) amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl-] group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
5 R24 and R25 are independently hydrogen, hydroxyl or halogen.
Particular examples of this substructure (Id') are:

- 1-bromo-9-hydroxy-4,6b,8a,11,12b,14b-hexamethyl-6b,7,8,8a,9,11,12,12a,12b,14b-decahydro-lH-picene-2,3,10-trione (C22);

10 - 1-bromo-4,6b,8a,11,12b,14b-hexamethyl-6b,7,8,8a,9,11,12,12a,12b,14b-decahydro-lH-picene-2,3,10-trione (C23).
In another preferred embodiment, the compounds of formula (Id) used in the present invention comprise a substructure 15 having the following formula (Id '):
H;C C00CH;
CH~

, CH~ CJ'C H;
R 2o~
R20~~ii õ
CH;
\; ~
Rlg' R~~

(Id" ) where:
R19r R19,, R20 and R20, are independently hydrogen; substituted or 20 non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is 25 comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen.

A particular example of this substructure (Id ' ) is 12-bromo-2,4a,6a,9,12a,14a-hexamethyl-10,11-dioxo-1,2,3,4,4a,5,6,6a,10,11,12,12a,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C24).
In another particular embodiment of the invention, the compound of formula (I) used in the prevention and/or treatment of a ChoK mediated disease or condition is a compound of formula (Ie) :
Rlo Ro R12nn,,,. ,"\\\Ra R~6R15 ;
_ ~nR
R2a H CHRS s R20 /iRa R20\\\\",,.
H I NsC R
R, R2 R1 ' Rlo ' R18' R18 R21 (Ie) where:

Rl, R2, R3, R4, R5, R6, R7, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(R14) (R ) amino, where RI4 and R' are independently hydrogen or an alkyl group Cl-C12) ; a carbinol group (CH2) n-OH (where n is an integer comprised between 1 and 10); or together form a methylene group;

R13, R14, R15, R16, R21 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl;

substituted or non-substituted C6-Clo aryl; a N(RvI) (RvII) amino group, where RvI and RvII are independently hydrogen or a Cl-Clz alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R18 and R18, are independently hydrogen; hydroxyl; halogen; Cl-Clz alkyl; C6-Clo aryl; CORIx (where RIx is hydrogen; hydroxyl; Cl-Clz alkyl; N(Rx) (RxI) amino, where Rx and RxI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12 alcoxyl); or trifluoromethyl;
R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORxII group (where RxII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(Rxzzz) (Rxzv' amino, where RxIII and Rxlv are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl- ]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen; and the bond ------ means a double bond or a single bond.

In a preferred embodiment, the compounds of formula (Ie) used in the present invention comprise a substructure having the following formula (Ie'):
H3C ,COOCH;
CH~

Rza Rzo' CH;
R2011ii1".
CH3 CH;
Rlo \\\,.
Rio R, 8 R18 (1e') where:
R18 and R18, are independently hydrogen; hydroxyl; halogen; Cl-Clz alkyl; C6-Clo aryl; CORIx (where RIx is hydrogen; hydroxyl; Cl-Clz alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12 alcoxyl); or trifluoromethyl;
R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl- ]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen.

A particular example of this substructure (Ie') is 9-hydroxy-2,4a,6a,9,12b-hexamethyl-10,11-dioxo-1,2,3,4,4a,5,6,6a,9,10,11,12b,13,14,14a,14b-hexadecahydro-picene-2-carboxylic acid methyl ester (C25).

In another particular embodiment of the invention, the compound of formula (I) used in the prevention and/or treatment of a ChoK mediated disease or condition is a compound of formula (If) :
Rlo Ro R12um,,, Ra R1;
R14 CH~ R7 R2a CH~ H CHR5 R2o R20""" ;C Rs Rio' R, R2 Rlo R1g' R18 R21 (If) where:

Rl, R2, R3, R4, R5, R6, R,, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(R14) (R ) amino, where RI4 and R are independently hydrogen or a Cl-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R14, R15, R21 and R23 are independently hydrogen; hydroxyl;
halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R18 and R18, are independently hydrogen; hydroxyl; halogen; Cl-Clz alkyl; C6-Clo aryl; CORIX (where RIX is hydrogen; hydroxyl; Cl-Clz alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12 alcoxyl) or trifluoromethyl;
R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl- ]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen; and the bond ------ means a double bond or a single bond.

In a preferred embodiment, the compounds of formula (If) used in the present invention comprise a substructure having the following formula (If'):
H;C 'COOCH;
CH~

R2a CH3 CH;

R20' R20i~~~
CH;
R lg' R, 8R1a 5 (If'~
where:
R18 and R18, are independently hydrogen; hydroxyl; halogen; Cl-Clz alkyl; C6-Clo aryl; CORIX (where RIX is hydrogen; hydroxyl; Cl-Clz alkyl; N(RX) (RXI) amino, where RX and RXI are independently 10 hydrogen or a Cl-C12 alkyl group; or Cl-C12 alcoxyl); or trifluoromethyl;
R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
15 substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-O- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a group C=O group together with the carbon 20 to which they are attached;
R24 is hydrogen, hydroxyl or halogen.

A particular example of this substructure (If') is the 9-hydroxy-2,4a,6a,6b,9-hexamethyl-10,11-dioxo-25 1,2,3,4,4a,5,6,6a,6b,8a,9,10,11,14,14a,14b-hexadecahydro-picene-2-carboxylic acid methyl ester (C26).

In another particular embodiment of the invention, the compound of formula (II) used in the prevention and/or treatment of a ChoK mediated disease or condition is a compound of formula (IIa) :

Rg R5 in/,,, ;
R2~ 2 R
R
a R1o R
R23 "'IR11 Cr13,12 R16 -11ii1IR13 (IIa) where:

Rlr R2, R3, R4, R5, R6r R9r Rlor Rllr R12r R13r R14r R15r R16r R17r R1ar R19 and R20 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(Rxv) (Rxvz) amino group, where Rxv and Rxvl are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a carboxyl (C=O) group together with the carbon to which they are attached;
R7 and R8 are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a CORxvII group (where Rxvzz is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; O-Cl-C12 alkyl;
or N(Rxvzzz) (Rxzx) amino, where RxvIII and Rxlx are independently hydrogen or a Cl-C12 alkyl group) ; a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10) ; or together form a methylene group, R21 and R24 are independently substituted or non-substituted Cl-C12 alkyl; a CORxx group (where Rxx is hydrogen; hydroxyl;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxz) (Rxxzz) amino, where Rxxl and Rxxzz are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl;

R22 and R23 are:

- hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORxxIII group (where RxxIII is hydrogen; hydroxyl;

substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxzv) (Rxxv) amino, where Rxxiv and Rxxv are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the para position with respect to R20; or OR22' and OR23' respectively, where R22' and R23' are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORxxvz group (where Rxxvz is hydrogen; hydroxyl;

substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxvzz) (Rxxvzzz) amino, where Rxxviz and Rxxvzzz are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the meta position with respect to Rzo=

In a preferred embodiment, the compounds of formula (IIa) used in the present invention comprise a substructure having the following formula (IIa'):
H3C '--COOCH;
R2a (IIa') where:
R19 and R20 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(Rxv) (Rxvz) amino group, where Rxv and Rxvl are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) carboxyl group together with the carbon to which they are attached;
R21 and R24 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(Rxxz) (Rxxzz) amino group, where Rxxl and RxxII are inde endentl h dro en or a C C alk 1 rou p Y Y g ~- ~z Y g p; or each pair can form a(C=0) carboxyl group together with the carbon to which they are attached;
R22 and R23 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; a N(Rxxzv) (Rxxv) amino group, where Rxxzv and Rxxv are independently hydrogen or a Cl-Clz alkyl group; or each pair can form a(C=0) carboxyl group together with the carbon to which they are attached.
A particular example of this substructure (IIa') is:
- 8-[2-(6,7-dihydroxy-1,5-dimethyl-naphthalen-2-yl)-ethyl]-2,4a-tetramethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-carboxylic acid methyl ester (C27).
The compounds of the invention act as blocking agents of the biosynthesis of phosphorylcholine by means of the selective blocking of the choline kinase (ChoK) enzyme and have shown a selective effect on signaling pathways necessary for the transformation by certain oncogenes which do not affect normal cells with the same intensity and therefore leave a sufficient margin for a greater efficacy in the tumor treatment.
Accordingly, in a particular embodiment, the Chok mediated disease or condition to be prevented or treated is cancer, preferably selected from breast, lung, colorectal and pancreatic cancer.
On the other hand, the biological assays carried out allow extending the use of the compounds described in the present invention for the treatment of viral, parasitic, bacterial and fungal conditions because some parasites such as Plasmodium falciparum or Trypanosoma cruci, some viruses such as adenovirus, bacteria such as Streptococcus pneumoniae and fungi such as Candida albicans require the metabolic phosphatidylcholine synthesis pathway through choline kinase to complete its infective cycles in humans and animals. In this sense, the bibliographic background supports the role of the ChoK enzyme in the intracellular metabolism of certain nucleosides in Hep-G2 cells, the use of said enzyme as an enzymatic marker in parasitic diseases and the participation thereof in the biosynthesis of important phospholipids in viruses, bacteria and fungi.
Consequently, in another embodiment the ChoK mediated disease or condition to be prevented and/or treated is a viral disease, preferably that caused by Adenovirus.
In another embodiment the ChoK mediated disease or condition to be prevented and/or treated is a parasitic disease, preferably that caused by Plasmodium or Trypanosoma.
In another embodiment the ChoK mediated disease or condition to be prevented and/or treated is bacterial disease, preferably that caused by Streptococcus.
In another embodiment the ChoK mediated disease or condition to be prevented and/or treated is a fungal disease, preferably that caused by Candida.

Another object of the present invention are the compounds of general formula (I):
Rlo Ro Rll R12i R8 CH ,.. R7 -111iRs (~ H CH3R5 R
a ~ ~~ Hsc R3 R, R2 (I) where:

Rl, R2, R3, R4, R5, R6, R7, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; an OCOR group, where R is (CH2) 2COOH or (CH2) 2CO2CH2CH3; or each pair can form a(C=0) group together with the carbon to which they are attached;

R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-Clz alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-Cl-Clz alkyl;
5 or N(R14) (R ) amino, where RI4 and R are independently hydrogen or a Cl-Clz alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group;
the bond ------ means a double bond or a single bond;
10 and where the tricyclic structure is selected from the following structures:

R14 R13 R14 R13 R14 Ris R RI s R15 tr;~~oõ~ Rw \o ,,,.
R
tr, 0 RzoO Rzo0 R zO R,,o R,,)O Rz3 Ria Ria R21 R22 Ria R21 (a) (b) (c) R 13 Ria Ris R1a Ris R15 RR1~Rza RiS
Rza RzSCH
CH, R2~j Rz0 Rzo R ,,,. Rzo """,. ~ Rzo "'~=.
o CH, R~~ ~ Ric' Ric' R2; Rz. Rz.
R~~ R~~ R
Rie R21 Rie~ ~Rip, R21 Rie' Rip, Rz, (d) (e) (f) where:
R13, R14, R15, R16, R21, R22 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted Cl-Clz alkyl;

substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-C12 alkyl group; an OCOR III group, where R III is (CH2) 2COOH or (CH2) 2CO2CH2CH3; or each pair can form a(C=0) group together with the carbon to which they are attached or each pair can form a (C=O) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
R18 and R18, are independently hydrogen; hydroxyl; halogen; Cl-C12 alkyl; C6-Clo aryl; CORIX (where RIX is hydrogen; hydroxyl; Cl-C12 alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12 alcoxyl); or trifluoromethyl;
R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen;

or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof, with the following provisos:

- when the tricyclic structure is (a) then the compound of formula (I) is not:

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid;

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3,10-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3-Hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 3,9-Dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 3,7,9-Trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 14-Bromo-3,7,9-trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- Succinic acid mono-(10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl) ester;

- Succinic acid ethyl ester 10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl ester;

- Acetic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dodecanoic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dimethyl-carbamic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Nicotinic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- 3,10-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester.

- when the tricyclic structure is (b) and R19 and R20 are independently hydrogen or an acyl group, then:

- R5 is hydroxyl; or - R21 and R22 form a C=O group together with the carbon to which they are attached and Rlo is not COOH.

- when the tricyclic structure is (c) and R19 and R20 are both CH3, then R15 and R16 do not form a C=O group together with the carbon to which they are attached.
In one particular aspect, the invention is directed to compounds of formula (Ia):
Rio Ro R> > Ra Ris Ri2iii111,,. ,-' JR7 Ris -11iiRo CH3 Rs O

R i R2 R1gO

(Ia) where Rl, R2, R3, R4, R5, R6, R7, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted Co-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; an OCOR group, where R is (CH2) 2COOH or (CH2) 2CO2CH2CH3; or each pair can form a(C=0) group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(R14) (R ) amino, where RI4 and R' are independently hydrogen or a Cl-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R14, R15 and R16 are independently hydrogen; hydroxyl;
halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-C12 alkyl group; an OCOR III group, where R III is (CH2) 2COOH or (CH2) 2CO2CH2CH3; or each pair can form a(C=0) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
R18 is hydrogen; hydroxyl; halogen; Cl-C12 alkyl; C6-Clo aryl; CORIX
(where RIX is hydrogen; hydroxyl; Cl-C12 alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12alcoxyl); or trifluoromethyl;
R19 is hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3) ;
or trifluoromethyl; and the bond ------ means a double bond or a single bond, with the proviso that the compound of formula (Ia) is not:
- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid;

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3,10-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-5 1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3-Hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

10 - 3,9-Dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 3,7,9-Trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-15 dione;

- 14-Bromo-3,7,9-trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- Succinic acid mono-(10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-20 3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl) ester;

- Succinic acid ethyl ester 10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-25 4-yl ester;

- Acetic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dodecanoic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-30 2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dimethyl-carbamic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-35 picen-3-yl ester;

- Nicotinic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester.

In a preferred embodiment, the compounds of formula (Ia) comprise a substructure having the following formula (Ia'):

CH;
O *61 (Ia') where R5 is hydroxyl or a OCOR group where R is (CH2) 2COOH or (CH2) 2CO2CH2CH3;
R7 and R8 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R' )(R" ) amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R12 is independently hydrogen or a halogen; and R19 is hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3) ;
or trifluoromethyl; and the bond ------ means a double bond or a single bond, with the proviso that the compound of formula (Ia') is not:

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid;

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3,10-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3-Hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 3,9-Dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 3,7,9-Trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 14-Bromo-3,7,9-trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- Succinic acid mono-(10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl) ester;

- Succinic acid ethyl ester 10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl ester;

- Acetic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dodecanoic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dimethyl-carbamic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Nicotinic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- 3,10-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester.

Particular examples of this substructure (Ia') are:
- 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl propionic acid ester (C1);

- 4-bromo-(9-hydroxy-6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl) benzoic acid ester (C2);

- 12-bromo-3,9-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione (C3);

- 12-bromo-9-hydroxy-6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl dimethyl-carbamic acid ester (C4);

- 4-bromo-(12-bromo-9-hydroxy-6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl) benzoic acid ester (C5);

- 3,9,10-trihydroxy-6b,8a,11,12b,14a-hexamethyl-7,8,8a,9,10,11,12,12a,12b,13,14,14a-dodecahydro-6bH-picene-2-one (C6).
In another preferred embodiment, the compounds of formula (Ia) comprise a substructure having the following formula (Ia"):

~~uRa C_H~
R15 =

O

CHJ~ CH3 C H;
(Ia" ) where:
R7 and R8 are independently hydrogen, hydroxyl, halogen, substituted or non-substituted Cl-C12 alkyl, substituted or non-substituted C6-Clo aryl, a N(R' )(R" ) amino group, where R' and R'' are independently hydrogen or a Cl-C12 alkyl group, or each pair can form a(C=0) group together with the carbon to which they are attached;
R15 is hydrogen or halogen;
R19 is hydrogen, substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3) ;
or trifluoromethyl; and the bond ------ means a double bond or a single bond, with the proviso that the compound of formula (Ia ") is not:
- 3-Hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,9,10,11,12,12a,12b,13,14,14a-dodecahydro-6bH-picen-2-one;

- 3-Hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione.

Particular examples of this substructure (Ia'') are:

-14-bromo-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione (C7);

-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-5 2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl acetic acid ester (C8);

-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl nicotinic acid ester (C9);

10 -3,10-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,9,10,11,12,12a,12b,13,14,14a-dodecahydro-6bH-picene-2-one (C10);

-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,12a,12b,13,14,14a-octahydro-6bH,9H-picene-2,10-15 dione (C11) .

In another preferred embodiment, the compounds of formula (Ia) comprise a substructure having the following formula (Ia,,,) :
H;C ,COOCH;

CH~

O ~

CH~ CH;
~ ~ J

20 H;
(Ia,,,) where:
R7 is hydrogen, hydroxyl, halogen, substituted or non-substituted Cl-C12 alkyl, substituted or non-substituted C6-Clo 25 aryl, or a N(R' )(R" ) amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; and R19 is substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl;
with the proviso that the compound of formula (Ia "') is not:
- 3,10-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester.

Particular examples of this substructure (Ia "') are:
- 2,4a,6a,9,12b,14a-hexamethyl-11-oxo-10-propionyloxy-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C13);

- 10-dimethylcarbamoyloxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C14).
In another particular aspect, the invention is directed to compounds of formula (Ib):
Rlo Ro R ll R1,,~111\ Ra R~~ DH R~

R16' .......

R200 ""'/iRa I I R17 NsC R3 R, R2 R1oO R23 (Ib) where:

Rl, R2, R3, R4, R5, R6, R7, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(R14) (R ) amino, where RI4 and R are independently hydrogen or a Cl-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R14, R15, R16, R21, R22 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-Clz alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
R18 is hydrogen; hydroxyl; halogen; Cl-C12 alkyl; C6-Clo aryl; CORIX
(where RIX is hydrogen; hydroxyl; Cl-C12 alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12 alcoxyl) ; or trifluoromethyl;
R19 and R20 are independently hydrogen, substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen;
hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl; and the bond ------ means a double bond or a single bond, with the proviso that when R19 and R20 are independently hydrogen or an acyl group, then:
R5 is hydroxyl; or R21 and R22 form a C=O group together with the carbon to which they are attached and Rlo is not COOH.
In another preferred embodiment, the compounds of formula (Ib) comprise a substructure having the following formula (Ib'):

O
CH~

OH
CH;

CH~ CH;

CH; OH
(Ib') where:
R19 and R20 are independently substituted or non-substituted Cl-C12 alkyl; a CORxII group (where RxII is hydrogen; hydroxyl;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(RxIII) (RxI ) amino, where RxIII and Rxzv are independently hydrogen or a Cl-C12 alkyl group); a[(Cl-C12) alkyl-O- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl.

A particular example of this substructure (Ib') is 4-nitro-(3-dimethylcarbamoyloxy-5,9-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-10-oxo-5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-2-yl) benzoic acid ester (C15).
In another preferred embodiment, the compounds of formula (Ib) comprise a substructure having the following formula (Ib"):
H3COOC CH;
H~

CH;
HO I CH~ CH;

R190 R2s (Ib" ) where:

R18 is hydrogen; hydroxyl; halogen; Cl-C12 alkyl; C6-Clo aryl; CORIX
(where RIX is hydrogen; hydroxyl; Cl-C12 alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12alcoxyl); or trifluoromethyl;
R19 is hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3) ;
or trifluoromethyl;
R23 is hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R 1 and R411 are independently hydrogen or a Cl-Cl2alkyl group.

Particular examples of this substructure (Ib'') are:

- 7,10,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester (F16);

- 9-formyl-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C17);

- 11-hydroxy-10-(2-methoxy-ethoxymethoxy)-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C18).

In another particular aspect, the invention is directed to compounds of formula (Ic):

Rlo Ro R ll R12iu,,,, ,,~111\ Ra R1 4 H~ R7 C
R15 = ., Rs R 16\" " H CHRS
R200 ""'/iRa R, R2 R1oO Rz3 (Ic) where:

5 Rl, R2, R3, R4, R5, R6, R7, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) 10 group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
15 or N(R14) (R ) amino, where RI4 and R are independently hydrogen or a Cl-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group;

R13, R14, R15, R16, R21 and R23 are independently hydrogen;
20 hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-Clz alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
25 R18 is hydrogen; hydroxyl; halogen; Cl-C12 alkyl; C6-Clo aryl; CORIX
(where RIX is hydrogen; hydroxyl; Cl-C12 alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-Cl2alcoxyl); or trifluoromethyl;

R19 and R20 are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen;
hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl- ]n group (where n is comprised between 1 and 3); or trifluoromethyl; and the bond ------ means a double bond or a single bond, with the proviso that when R19 and R20 are both CH3, then R15 and R16 do not form a C=O group together with the carbon to which they are attached.

In a preferred embodiment, the compounds of formula (Ic) comprise a substructure having the following formula (Ic'):

CH~

(Ic') where:
R19 and R20 are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen;
hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3) or trifluoromethyl; and the bond ------ means a double bond or a single bond.
Particular examples of this substructure (Ic') are:

- 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-1,4,4a,5,6,6a,13,14,14a,14b-decahydro-2H-picene-3-one (C19) ;

- 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-4a,5,6,6a,13,14,14a,14b-octahydro-4H-picene-3-one (C20).
In another preferred embodiment, the compounds of formula (Ic) comprise a substructure having the following formula (Ic"):
H3C \--COOCH3 CH~

(Ic" ) where:
R19 and R20 are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen;
hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl- ]n group (where n is comprised between 1 and 3); or trifluoromethyl.

A particular example of this substructure (Ic") is 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-1,2,3,4,4a,5,6,6a,13,14,14a,14b-dodecahydro-picene-2-carboxylic acid methyl ester (C21).
In another particular aspect, the invention is directed to compounds of formula (Id):

Rlo Ro R12m,,,, Ra R13 CH~ R~
R15 nRs R2o R20 ;C R3 R, R2 R1o' ; R2s Rjo (Id) where:

Rl, R2, R3, R4, R5, R6, R7, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Cl2 alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(R14) (R ) amino, where RI4 and R are independently hydrogen or a Cl-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R15, R21 and R23 are independently hydrogen; hydroxyl;
halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R18 is hydrogen; hydroxyl; halogen; Cl-C12 alkyl; C6-Clo aryl; CORIX
(where RIX is hydrogen; hydroxyl; Cl-C12 alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-Cl2alcoxyl); or trifluoromethyl;

R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl- ]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen; and the bond ------ means a double bond or a single bond.

In a preferred embodiment, the compounds of formula (Id) comprise a substructure having the following formula (Id'):

O
C_H~
= R5 R%4RCH; HR6 R2o R20u~

Rig' Rlg CH;
(Id') where:
R5 and R6 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R' )(R" ) amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen.
5 Particular examples of this substructure (Id') are:

- 1-bromo-9-hydroxy-4,6b,8a,11,12b,14b-hexamethyl-6b,7,8,8a,9,11,12,12a,12b,14b-decahydro-lH-picene-2,3,10-trione (C22);

- 1-bromo-4,6b,8a,11,12b,14b-hexamethyl-10 6b,7,8,8a,9,11,12,12a,12b,14b-decahydro-lH-picene-2,3,10-trione (C23).
In another preferred embodiment, the compounds of formula (Id) comprise a substructure having the following formula (Id"):
H3C OOCH;
CH~

CH~ CH;
R20' R20~~ii Rlo' Rlo 15 CH;
(Id" ) where:
R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is 20 hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl- ]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 25 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen.

A particular example of this substructure (Id ' ) is 12-bromo-2,4a,6a,9,12a,14a-hexamethyl-10,11-dioxo-1,2,3,4,4a,5,6,6a,10,11,12,12a,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester (C24).
In another particular aspect, the invention is directed to compounds of formula (Ie):

R1o Ro R12u~~,,, R15 ;
,111nR6 R2a H CHRS
R2o' "/R
a \\\~~~,,, R20 CH , H3C R3 R1o' R1 R2 ~ R23 R1o R1g' R18 R21 (Ie) where:

Rl, R2, R3, R4, R5, R6, R7, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Cl2 alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(R14) (R ) amino, where RI4 and R are independently hydrogen or an alkyl group Cl-C12) ; a carbinol group (CH2) n-OH (where n is an integer comprised between 1 and 10); or together form a methylene group;

R13, R14, R15, R16, R21 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-Cl2 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R18 and R18' are independently hydrogen; hydroxyl; halogen; Cl-Clz alkyl; C6-Clo aryl; CORIx (where RIx is hydrogen; hydroxyl; Cl-Clz alkyl; N(Rx) (RxI) amino, where Rx and RxI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12 alcoxyl); or trifluoromethyl;
R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORxII group (where RxII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(Rxzzz) (Rxzv' amino, where RxIII and Rxlv are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-O- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen; and the bond ------ means a double bond or a single bond.

In a preferred embodiment, the compounds of formula (Ie) comprise a substructure having the following formula (Ie'):
H3C ,COOCH;
CH~

R2a CH;
R20' R2011ii1".
CH~ CH;
Rlg .~'Rig ";
R18' R18 (1e') where:
R18 and R18, are independently hydrogen; hydroxyl; halogen; Cl-Clz alkyl; C6-Clo aryl; CORIx (where RIx is hydrogen; hydroxyl; Cl-Clz alkyl; N(Rx) (RxI) amino, where Rx and RxI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12 alcoxyl) or trifluoromethyl;

R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl- ]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen.

A particular example of this substructure (Ie') is 9-hydroxy-2,4a,6a,9,12b-hexamethyl-10,11-dioxo-1,2,3,4,4a,5,6,6a,9,10,11,12b,13,14,14a,14b-hexadecahydro-picene-2-carboxylic acid methyl ester (C25).
In another particular aspect, the invention is directed to compounds of formula (If):

Rlo Ro R12m,,,, ,,\\\ Ra R1a 131 R~

R15 = R6 R2a CH~ H CHR5 ""'/iRa \\\\~,,,.
R20 3C Rs R, R2 Rlo' R2s R1o R1g' R18 R21 (If) where:

Rl, R2, R3, R4, R5, R6, R,, R8, Rll and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R')(R ') amino group, where R' and R" are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;

R9 and Rlo are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a COR' '' group (where R' '' is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(R14) (R ) amino, where RI4 and R are independently hydrogen or a Cl-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R14, R15, R21 and R23 are independently hydrogen; hydroxyl;
halogen; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(R41) (R411) amino group, where R41 and R411 are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R18 and R18, are independently hydrogen; hydroxyl; halogen; Cl-Clz alkyl; C6-Clo aryl; CORIX (where RIX is hydrogen; hydroxyl; Cl-Clz alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12 alcoxyl); or trifluoromethyl;
R19r R19,, R20 and R20, are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen; and the bond ------ means a double bond or a single bond.

In a preferred embodiment, the compounds of formula (If) comprise a substructure having the following formula (If'):

H3C \COOCH;

CH~
R2a R2o' R20i~~

Rlg R ~~

(If') where:
R18 and R18, are independently hydrogen; hydroxyl; halogen; Cl-Clz 5 alkyl; C6-Clo aryl; CORIX (where RIX is hydrogen; hydroxyl; Cl-Clz alkyl; N(RX) (RXI) amino, where RX and RXI are independently hydrogen or a Cl-C12 alkyl group; or Cl-C12 alcoxyl); or trifluoromethyl;
R19r R19,, R20 and R20, are independently hydrogen; substituted or 10 non-substituted Cl-C12 alkyl; a CORXII group (where RXII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-Clo aryl; or N(RXIII) (RXI ) amino, where RXIII and RX14 are independently hydrogen or a Cl-C12 alkyl group) ; a [(Cl-C12) alkyl-O- (Cl-C12) alkyl-] n group (where n is 15 comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a group C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen.

20 A particular example of this substructure (If') is the 9-hydroxy-2,4a,6a,6b,9-hexamethyl-10,11-dioxo-1,2,3,4,4a,5,6,6a,6b,8a,9,10,11,14,14a,14b-hexadecahydro-picene-2-carboxylic acid methyl ester (C26).
Another aspect of the invention is formed by compounds of 25 formula (II):

R
s \Ro ::1 (11) where:

R, R2, R3, R4, R5, R6i R9i Rloi Rlli R12i R13i R14i R15i R16i R17i Rlai R19 and R20 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(Rxv) (Rxvz) amino group, where Rxv and Rxvl are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a carboxyl (C=O) group together with the carbon to which they are attached;
R7 and R8 are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a CORxvII group (where Rxvzz is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; O-Cl-C12 alkyl;
or N(Rxvzzz) (Rxzx) amino, where RxvIII and Rxlx are independently hydrogen or a Cl-C12 alkyl group) ; a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10) ; or together form a methylene group, R21 and R24 are independently substituted or non-substituted Cl-C12 alkyl; a CORxx group (where Rxx is hydrogen; hydroxyl;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxz) (Rxxzz) amino, where Rxxl and Rxxzz are independently hydrogen or a Cl-C12 alkyl group); a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl;

R22 and R23 are:

- hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORxxIII group (where RxxIII is hydrogen; hydroxyl;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxzv) (Rxxv) amino, where Rxxiv and Rxxv are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the para position with respect to R20; or OR22' and OR23' respectively, where R22' and R23' are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORxxvz group (where Rxxvz is hydrogen; hydroxyl;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxvzz) (Rxxvzzz) amino, where Rxxviz and Rxxvzzz are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the meta position with respect to R20=
or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof.

In one particular aspect, the invention is directed to compounds of formula (IIa):

R
s '\\Rg R 2 R R5 nu",,.
R

a R1o Cr~12 ~~'~

(IIa) where:

Rlr R2, R3, R4, R5, R6, R9r Rlor Rllr R12r R13r R14r R15r R16r R17r R18r R19 and R20 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; a N(Rxv) (Rxvz) amino group, where Rxv and Rxvl are independently hydrogen or a Cl-C12 alkyl group; or each pair can form a carboxyl (C=O) group together with the carbon to which they are attached;

R7 and R8 are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; C6-Clo aryl; a CORxvII group (where Rxvzz is hydrogen; hydroxyl; substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; 0-C1-C12 alkyl;
or N(Rxvzzz) (Rxzx) amino, where RxvIII and Rxlx are independently hydrogen or a Cl-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10) ; or together form a methylene group, R21 and R24 are independently substituted or non-substituted Cl-C12 alkyl; a CORxx group (where Rxx is hydrogen; hydroxyl;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxz) (Rxxzz) amino, where Rxxl and Rxxzz are independently hydrogen or a Cl-C12 alkyl group); a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl;

R22 and R23 are:

- hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORxxIII group (where RxxIII is hydrogen; hydroxyl;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxzv) (Rxxv) amino, where Rxxzv and Rxxv are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the para position with respect to R20; or - OR22' and OR23' respectively, where R22' and R23' are independently hydrogen; substituted or non-substituted Cl-C12 alkyl; a CORxxvz group (where Rxxvz is hydrogen; hydroxyl;
substituted or non-substituted Cl-C12 alkyl; substituted or non-substituted C6-Clo aryl; or N(Rxxvzz) (Rxxvzzz) amino, where Rxxviz and Rxxvzzz are independently hydrogen or a Cl-C12 alkyl group) ; a[(Cl-C12) alkyl-0- (Cl-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the meta position with respect to Rzo=

In a preferred embodiment, the compounds of formula (IIa) comprise a substructure having the following formula (IIa'):

H3C '--COOCH;

Rz4 CH;

(IIa') where:
R19 and R20 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-C1z alkyl; substituted or non-substituted C6-Clo aryl; a N(Rxv) (Rxvz) amino group, where Rxv and Rxvl are independently hydrogen or a Cl-Clz alkyl group; or each pair can form a (C=O) carboxyl group together with the carbon to which they are attached;
R21 and R24 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; a N(Rxxz) (Rxxzz) amino group, where Rxxl and RxxII are inde endentl h dro en or a C C alk 1 rou p Y Y g ~- ~z Y g p; or each pair can form a (C=O) carboxyl group together with the carbon to which they are attached;
R22 and R23 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted Cl-Clz alkyl; substituted or non-substituted C6-Clo aryl; a N(Rxxzv) (Rxxv) amino group, where Rxxzv and Rxxv are independently hydrogen or a Cl-Clz alkyl group; or each pair can form a (C=O) carboxyl group together with the carbon to which they are attached.

A particular example of this substructure (IIa') is:
- 8-[2-(6,7-dihydroxy-1,5-dimethyl-naphthalen-2-yl)-ethyl]-2,4a-tetramethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-carboxylic acid methyl ester (C27).
In another aspect the present invention relates to a process for preparing compounds of formula (I) comprising the following features:
a) The usual methodology for the chemoselective introduction in the hydroxyl in C-3 of the natural Friedelane derivative of the chemical family of pristimerin-related methylene triterpenequinones requires an analysis of the basicity conditions for abstracting the phenolic proton and subsequent reaction 5 with the indicated acylation agents or agents of another type. It is relevant that if the pH control is not appropriate, reactions on C-6 that complicate the synthetic process occur.
b) The method for the chemoselective introduction in C-23 10 of the indicated groups will be carried out by controlled oxidation with specific reagents for allyl aromatic systems and subsequent transformations of the functionality thus obtained.
c) By means of an already studied process, C-25 will be 15 transformed in a fluoromethyl group and the subsequent functional group transformations will allow reaching the indicated groups.
d) The use of heterolytic and homolytic halogenation reactions together with chemoselective oxidation 20 processes and the introduction of nitrogens by means of the use of azides forms parts of any of the methods to be used for obtaining the objectives.
e) Taking advantage of the functionalizations in C-11, the previously studied methodology will be used to obtain 25 C11-C12 double bonds which will serve as a functional group to apply a FGT (Functional Group Transformations) to them for the purpose of preparing the envisaged compounds.
f) The C-15 and C16 positions have been functionalized by 30 carrying out allylic oxidation reactions from double bonds in ring E or in ring C and from then onwards, the application of FGT.
g) The C-19, C-20, C-21 and C-22 positions can be partially functionalized in some starting substrates and the 35 chemistry for introducing functional groups in this ring has been widely elaborated.

Particular examples of the present invention are described in the preparation example section, nevertheless a person skilled in the art would achieve synthesizing any of the described compounds by conventional synthetic compounds of the state of the art.
The term "pharmaceutically acceptable salts, solvates, prodrugs" refers to any pharmaceutically salt, ester, solvate or any other compound which when administered to a receptor is able to provide (directly or indirectly) a compound as described in the present document. However, it will be observed that pharmaceutically unacceptable salts are also within the scope of the invention because the latter can be useful in the preparation of pharmaceutically acceptable salts. The preparation of salts, prodrugs and derivatives can be carried out by means of methods known in the art.
For example, pharmaceutically acceptable salts of compounds provided in the present document are synthesized by means of conventional chemical methods from an original compound containing a basic or acid residue. Such salts are generally prepared, for example, by reacting the free acid or base forms of the compounds with a stoichiometric amount of the suitable base or acid in water or an organic solvent or a mixture of both. Non-aqueous media such as ether, ethyl acetate, ethanol, isopropanol or acetonitrile are generally preferred. Examples of acid addition salts include mineral acid addition salts such as for example, hydrochloride, bromohydrate, iodohydrate, sulfate, nitrate, phosphate and organic acid addition salts such as for example, acetate, maleate, fumarate, citrate, oxalate, succinate, tartrate, malate, mandelate, methanesulfonate and p-toluenesulfonate. Examples of base addition salts include inorganic salts such as for example sodium, potassium, calcium, ammonium, magnesium, aluminium and lithium salts and organic base salts such as for example ethylenediamine, ethanolamine, N,N-dialkylenethanolamine, triethanolamine, glucamine and basic amino acid salts.
The particularly preferred derivatives or prodrugs are those increasing the bioavailability of the compounds of this invention when such compounds are administered to a patient (for example, by making a compound administered orally be absorbed more easily by blood), or enhancing the release of the original compound in a biological compartment (for example, the brain or the lymphatic system) in relation to the original species.
Any compound which is a prodrug of a compound of formula (I) or of formula (II) is within the scope of the invention. The term "prodrug" is used in its widest sense and includes those derivatives which are converted in vivo into the compounds of the invention. Such derivatives are evident for the persons skilled in the art and depending on the functional groups present in the molecule and without limitation, include the following derivatives of the present compounds: esters, amino acid esters, phosphate esters, metal salt sulfonate esters, carbamates and amides. Examples of methods for producing a prodrug of a given active compound are known by the person skilled in the art and can be found for example in Krogsgaard-Larsen et al. "Textbook of Drug design and Discovery" Taylor &
Francis (April 2002).
The compounds of the invention can be in crystalline form as free compounds or as solvates and it is intended that both of them are within the scope of the present invention. The solvation methods are generally known in the art. The suitable solvates are pharmaceutically acceptable solvates. In a particular embodiment, the solvate is a hydrate.
The compounds of the present invention represented by the formula (I) described previously can include enantiomers, depending on the presence of chiral centers on a C, or isomers, depending on the presence of multiple bonds (for example, Z, E).
The individual isomers, enantiomers or diastereoisomers and the mixtures thereof are included within the scope of the present invention.
The different substituents selected for the different compounds of the invention provide a series of factors considerably affecting the values of log P. Thus, hydroxyl groups act as hydrogen bond donors and intra or intermolecular links can be established even in the case of phenols. The presence of carbonyl or carboxyl groups generates proton acceptor groups in the molecule. The presence of halogens generates very deficient carbons and considerably modifies the biological properties. The amino groups generate good nucleophiles on the molecule and in most cases significantly modify its polarity and polarizability and the presence of additional alkyl and/or aryl groups increases the lypophilicity of the molecules.
The present invention additionally provides pharmaceutical compositions comprising a compound of formula (I), (Ia), (Ia'), (Ia" ) , (Ia,, , ) , (Ib) , (Ib' ) , (Ib" ) , (Ic) , (Ic' ) , (Ic' ) , (Id) , ( I d ' (Id " ) , (1e), (1e'(If) , (If'), (II) , (IIa), (IIa') or mixtures thereof, a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof together with a pharmaceutically acceptable carrier, adjuvant or vehicle for the administration to a patient.
The pharmaceutical compositions can be administered by any suitable administration route, for example an oral, topical, rectal or parenteral route (including subcutaneous, intraperitoneal, intradermal, intramuscular and intravenous route).
Suitable pharmaceutical forms for oral administration include any solid composition (tablets, pastilles, capsules, granules, etc.) or liquid composition (solutions, suspensions, emulsions, syrups, etc.) and can contain conventional excipients known in the art, such as binding agents, for example syrup, acacia, gelatin, sorbitol, tragacanth, or polyvinylpyrrolidone;
fillers, for example lactose, sugar, cornstarch, calcium fosfate, sorbitol or glycine; lubricants for the preparation of tablets, for example magnesium stearate, disintegrants, for example starch, polyvinylpirrolidone, sodium starch glycolate or microcrystalline cellulose; or pharmaceutically acceptable wetting agents such as sodium laurylsulfate.
Solid oral compositions can be prepared by means of conventional methods for mixing, filling or preparing tablets.
The repeated mixing operations can be used to distribute the active ingredient through the entire compositions by using large amounts of filler agents. Such operations are conventional in the art. The tablets can be prepared, for example by means of wet or dry granulation and can be optionally coated according to methods well known in normal pharmaceutical practice, particularly with an enteric coating.
The pharmaceutical compositions can also be adapted for parenteral administration such as sterile solutions, suspensions or lyophilized products in a suitable unitary pharmaceutical form. Suitable excipients such as bulk agents, buffering agents or surfactants can be used.
The mentioned formulations will be prepared using usual methods such as those described or referred to in Spanish Pharmacopoeia and the Pharmacopoeia of the United States and in similar reference texts.
The administration of the compounds or compositions used in the present invention can be by any suitable method, such as intravenous infusion, oral preparations and intraperitoneal and intravenous administration. Nevertheless, the preferred administration route will depend on the patient's condition.
Oral administration is preferred due to the comfort for the patient and the chronic character of the diseases which are to be treated.
For their application in therapy, the compounds of formula (I) and formula (II) will preferably be found in pharmaceutically acceptable or substantially pure form, i.e. the compounds of formula (I) and formula (II) have a pharmaceutically acceptable purity level excluding the pharmaceutically acceptable excipients and not including material considered to be toxic at the normal dosage levels. The purity levels for a compound of formula (I) or for a compound of formula (II) preferably exceed 50%, more preferably exceed 70%, more preferable exceed 90%. In a preferred embodiment, they exceed 95%.
The therapeutically effective amount of the compound of formula (I) or of the compound of formula (II) to be administered will generally depend, among other factors, on the individual who is to be treated, on the severity of the disease said individual suffers from, on the administration form chosen etc. For this reason, the doses mentioned in this invention must be considered as guides for the person skilled in the art and the latter must adjust the doses according to the variables 5 mentioned previously. Nevertheless, a compound of formula (I) can be administered once or more times a day, for example, 1, 2, 3 or 4 times a day in a typical daily total amount comprised between 1 and 200 mg/kg body mass/day, preferably 1-10 mg/kg body mass/day. In the same manner a compound of formula (II) can 10 be administered once or more times a day, for example, 1, 2, 3 or 4 times a day in a typical daily total amount comprised between 1 and 200 mg/kg body mass/day, preferably 1-10 mg/kg body mass/day.
The compounds described in this invention, their 15 pharmaceutically acceptable salts, prodrugs and/or solvates, as well as the pharmaceutical compositions containing them can be used together with other additional drugs to provide a combination therapy. Said additional drugs can form part of the same pharmaceutical composition or can alternatively be provided 20 in the form of a separate composition for its simultaneous or non-simultaneous administration with the pharmaceutical composition comprising a compound of formula (I) or of formula (II), or a pharmaceutically acceptable prodrug, solvate or salt thereof.
25 The other drugs can form part of the same composition or be provided as a separate composition for its administration at the same time or at different times.

A last object of the invention is formed by a compound of 30 formula (I), (Ia), (Ia' ) , (Ia" ) , (Ia"' ), (Ib), (Ib' ) , (Ib" ) , (Ic), (Ic' ) , (Ic" ) , (Id), (Id' ) , (Id" ) , (Ie), (Ie' ) , (If), (If'), (II), (IIa), (IIa') or mixtures thereof, or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof for use in the treatment of cancer, 35 parasitic diseases, bacterial diseases or fungal diseases.

The following examples are given only as an additional illustration of the invention, they must not be interpreted as limiting the invention as it is defined in the claims.

EXAMPLES
PREPARATION EXAMPLES
Example 1 Compound C3: 12-bromo-3,9-dihydroxy-6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picen-2,10-dione 300 g of Maytenus amazonica root bark were extracted in 2 liters of a n-hexane-ethyl ether 1:1 solvent mixture in soxhlet equipment under reflux for 48 hours, obtaining 70 grams of a reddish solid after evaporating the solvent. The extract was chromatographed on a sephadex LH-20 column, using a n-hexane-CHC13-MeOH 2:1:1 mixture as eluent. A total of 41 fractions were obtained which were gathered in seven groups (A, B, C, D, E, F
and G) according to thin layer chromatography. These groups were in turn fractioned in sephadex LH-20 columns, in medium pressure silica gel columns and in preparation plates, from which the starting compound 22(3-hydroxy-tingenone or [3,9-dihydroxy-6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picen-2,10-dione] was obtained.

342 mg (0.78 mmoles) of 22(3-hydroxy-tingenone in 50 ml of dry CH2C12, under an inert atmosphere and at 0 C were treated with 1.5 eq of BBr3 (1M) . The reaction mixture was followed by thin layer chromatography, and was left stirring for 30 minutes until the starting product ran out. After this time, 50 ml of cold distilled water was added and the mixture was stirred for another 30 minutes. Then, an extraction with CH2C12 was carried out. The organic phases were dried with anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure.
The residue was purified by LH-20 sephadex chromatography using n-hexane:chloroform:methanol 2:1:1 mixture as eluent and in a silica gel chromatography column using n-hexane-ethyl acetate 7:3 as eluent. 111 mg (27%) of product C3 was obtained.

1H NMR (300 MHz, CDC13) S 0.50 (3H, s, Me-27); 1.16 (3H, d, J=
5.9 Hz, Me-30); 1.29 (3H, s, Me-26); 1.36 (3H, s, Me-28); 1.44 (3H, s, Me-25); 2.20 (3H, s, Me-23); 2.61 (1H, m, H-20); 3.70 (1H, d, J= 2. 9 Hz, H-22) ; 4.03 (1H, dd, J1= 2. 6, J2= 10.2 Hz, H-19) ; 6.32 (1H, d, J= 7.2 Hz, H-7) ; 6.50 (1H, d, J= 1.3 Hz, H-1) ;
7.00 (1H, dd, J1= 1.3, J2= 7.1 Hz, H-6) . 13C NMR (75 MHz, CDC13) $
10.2 (c, C-23); 20.3 (c, C-27); 20.9 (c, C-30); 21.7 (c, C-26);
27. 9(t, C-16) ; 28.0 (t, C-15) ; 28. 9(t, C-12) ; 30. 9(c, C-28) ;
33.4 (t, C-11); 37.9 (c, C-25); 40.0 (d, C-20); 40.4 (s, C-14);
42.7 (s, C-9) ; 44.4 (s, C-13) ; 45.5 (s, C-17) 48.7 (d, C-18) ;
76. 6 (d, C-19) ; 77.2 (d, C-22) ; 118. 6(d, C-7) ; 119. 6(d, C-1) ;
127.7 (s, C-5); 133.7 (d, C-6); 146.1 (s, C-4); 149.5 (s, C-3);
164.1 (s, C-10) ; 167.9 (s, C-8); 178.4 (s, C-2) ; 216.5 (s, C-21). High resolution MS Calculated for (M+-Br) C28H3604 436.2614, observed 436.2695.
Example 2 Compound C7: 14-Bromo-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione 100 mg (0.23 mmoles) of 22(3-hydroxy-tingenone, obtained according to example 1, were dissolved in 10 ml of CH2C12 and were treated with 82 mg of NBS (2eq) for 2h at room temperature.
The reaction mixture was followed by TLC and when there was no more starting product, an extraction with CH2C12 was carried out.
The organic phase was dried with anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using n-hexane:AcOEt mixtures in polarity increasing from 10% to 60% as an eluent to obtain: 1.2 mg (1%) of compound C7 and a mixture of other compounds.

1H NMR (300 MHz, CDC13) S 0.99 (3H, s, Me-28); 1.00 (3H, d, J=
5.2 Hz, Me-30); 1.01 (3H, s, Me-27); 1.38 (3H, s, Me-26); 1.76 (3H, s, Me-25); 2.20 (3H, s, Me-23); 4.81 (1H, dd, J1= 6.7 Hz, J2= 12.0 Hz, H-11); 6.28 (1H, d, J= 7.0 Hz, H - 7 ) ; 6.89 (1H, d, J= 7.0 Hz, H-6) ; 7.35 (1H, s, H-1).. 13C NMR (75 MHz, CDC13) S
10.2 (c, C-23); 14.9 (c, C-30); 19.5 (c, C-27); 21.2 (c, C-26);

28.3 (t, C-15); 31.7 (t, C-16); 32.0 (c, C-28); 35.0 (t, C-19);
37.6 (c, C-25); 38.1 (s, C-13); 41.6 (d, C-18); 42.4 (s, C-14) ;
42.8 (d, C-20); 44.3 (s, C-17); 44.9 (t, C-12); 46.8 (s, C-9);
51.6 (t, C-22); 58.3 (d, C-11); 117.9 (s, C-4); 118.4 (d, C-7) ;
121.1 (d, C-1) ; 129. 6(s, C-5) ; 131.4 (d, C-6) ; 152. 9(s, C-3) ;
162.7 (s, C-10); 165.4 (s, C-8); 178.3 (s, C-2); 212.8 (s, C-21) . High resolution MS Calculated for C28H35BrO3 498.1770, observed 498.1801.
Example 3 Compound C8: (4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl) acetic acid ester 300 g of Maytenus amazonica root bark were extracted in 2 liters of a n-hexane-ethyl ether 1:1 solvent mixture in soxhlet equipment under reflux for 48 hours, obtaining 70 grams of a reddish solid after evaporating the solvent. The extract was chromatographed on a sephadex LH-20 column, using a n-hexane-CHC13-MeOH 2:1:1 mixture as eluent. A total of 41 fractions were obtained which were gathered in seven groups (A, B, C, D, E, F
and G) according to thin layer chromatography. These groups were in turn fractioned in sephadex LH-20 columns, in medium pressure silica gel columns and in preparation plates, from which the starting compound called tingenone was obtained.
40 mg (0.096 mmoles) of tingenone in 10 ml of dry CH2C12 were treated with 0.04 ml (3 eq) of dry Et3N and 0.01 ml (1.5 eq) of acetyl chloride. The reaction was carried out at room temperature, followed by TLC and stirred for 2h. The process described in the previous reactions was followed. The raw product was purified by preparative chromatography on silica gel using n-hexane:AcOEt (2:3) as a mobile phase, to give 24 mg (54%) of product C8. The residue was starting product.

'H NMR (300 MHz, CDC13) 8 7.08 (1H, dd, J1= 1.3, J2= 7.0 Hz, H-6) ;
6.50 (1H, d, J=1.4 Hz, H-1) ; 6.35 (1H, d, J= 7.1 Hz, H-7) ; 2.49 (1H, m, H-20); 2.36 (3H, s, Me-C00); 2.16 (3H, s, Me-23); 1.52 (3H, s, Me-25); 1.35 (3H, s, Me-26); 1.00 (3H, s, Me-27); 0.99 (3H, d, J- 6.2 Hz, Me-30) ; 0.98 (3H, s, Me-28) . 13C NMR (75 MHz, CDC13) S 11.1 (c, C-23); 14.8 (c, C-30); 19.5 (c, C-27) ; 20.3 (c, CH3C00); 21.6 (c, C-26); 28.2 (t, C-15); 29.6 (t, C-12);
31.8 (t, C-19); 32.3 (c, C-28); 33.6 (t, C-11) ; 35.2 (t, C-16);
37.9 (s, C-17); 38.8 (c, C-25); 40.2 (s, C-13); 41.7 (d, C-20);
42.2 (s, C-9); 43.3 (d, C-18); 44.6 (s, C-14); 52.3 (t, C-22);
117.6 (d, C-7); 122.9 (d, C-1) ; 126.4 (s, C-5); 133.5 (s, C-4);
134.9 (d, C-6); 142.8 (s, C-3); 162.9 (s, C-10); 168.5 (s, CH3CO0); 170.4 (s, C-8) ; 177.3 (s, C-2) ; 213.4 (s, C-21) . High resolution MS Calculated for C30H3804 462.2770, observed 462.2784.
Example 4 Compound C9: (4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl) nicotinic acid ester 98 mg (0.23 mmoles) of tingenone (obtained according to example 3) were dissolved in 10 ml of dry CH2C12 and were treated with 0.097 ml (3 eq) of dry Et3N, 62.12 mg (1.5 eq) of nicotyl chloride and catalytic amounts of DMAP. The reaction was carried out at room temperature, followed by TLC and stirred for 20 minutes. The process described in the previous reactions was followed and the raw product was purified by preparative chromatography on silica gel using CH2C12:AcOEt (1:1) as a mobile phase, to give 55 mg (46%) of product C9. The residue was starting product.

'H NMR (300 MHz, CDC13) S 9.37 (1H, dd, J1= 0.9, J2= 2.1 Hz, Ha) ;
8.81 (1H, dd, J1= 1.7, J2= 4. 9 Hz, Hd) ; 8. 43 (1H, dd, J1= 1. 9, J2=
8.2 Hz, Hb) ; 7.44 (1H, m, HC) ; 7.13 (1H, dd, J1= 1.2, J2= 7.0 Hz, H-6) ; 6.53 (1H, d, J=1 .3 Hz, H-1) ; 6.38 (1H, d, J= 7.1 Hz, H-7) ;
2.49 (1H, m, H-20); 2.22 (3H, s, Me-23); 1.54 (3H, s, Me-25);
1.35 (3H, s, Me-26) ; 0.99 (3H, s, Me-27) ; 0.97 (3H, d, J- 6.6 Hz, Me-30) ; 0. 95 (3H, s, Me-28) . 13C NMR (75 MHz, CDC13) 6 11.23 (c, C-23); 14.84 (c, C-30); 19.54 (c, C-27); 21.59 (c, C-26);
28.26 (t, C-15) ; 29.63 (t, C-12) ; 31.78 (t, C-19) ; 32.30 (c, C-28); 33.69 (t, C-11); 35.23 (t, C-16); 37.91 (s, C-17); 38.81 (c, C-25); 40.23 (s, C-13); 41.65 (d, C-20); 42.29 (s, C-9);
43.26 (d, C-18) ; 44.64 (s, C-14) ; 52.26 (t, C-22) ; 117.6 (d, C-7); 123.0 (d, C-1); 123.2 (d, CH-Ar); 125.0 (s, C-Ar); 126.3 (s, C-5); 133.8 (s, C-4); 135.2 (d, C-6); 137.6 (d, CH-Ar); 142.7 (s, C-3); 151.3 (d, N-CH); 153.7 (d, N-CH); 162.8 (s, C-10);
162.9 (s, OCO-Nic); 170.7 (s, C-8); 176.8 (s, C-2); 213.3 (s, C-21) . High resolution MS Calculated for C34H39NO4 525.2879, 5 observed 525.2899.
Example 5 Compound C12: 3,10-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-2-carboxylic acid methyl ester.
10 1500 g of Salacia root bark were extracted in 2 liters of a n-hexane-ethyl ether 1:1 solvent mixture, obtaining 5 grams of a reddish extract after evaporating the solvent. The extract was chromatographed on several silica gel columns, from which compound C12 was obtained.
15 Example 6 Compound C14: 10-Dimethylcarbamoyloxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-2-carboxylic acid methyl ester 300 g of Maytenus amazonica root bark were extracted in 2 20 liters of a n-hexane-ethyl ether 1:1 solvent mixture in soxhlet equipment under reflux for 48 hours, obtaining 70 grams of a reddish solid after evaporating the solvent. The extract was chromatographed on a sephadex LH-20 column, using a n-hexane-CHC13-MeOH 2:1:1 mixture as eluent. A total of 41 fractions were 25 obtained which were gathered in seven groups (A, B, C, D, E, F
and G) according to thin layer chromatography. These groups were in turn fractioned in sephadex LH-20 columns, in medium pressure silica gel columns and in preparation plates, from which the starting compound called pristimerin was obtained.
30 65 mg (0.14 mmoles) of pristimerin in 5 ml of dry CH2C12 were treated with 0.062 ml (3 eq) of dry Et3N, 0.02 ml (1.5 eq) of N,N-dimethylcarbamoyl chloride and catalytic amounts of DMAP.
The reaction was carried out at 0'C and under an inert atmosphere, followed by TLC and stirred for 24h. Then 5% diluted 35 hydrochloric acid was added until neutralization. Then the organic phase was extracted with CH2C12 and was dried with anhydrous magnesium sulfate. It was filtered and concentrated under reduced pressure. The raw product was purified by preparative chromatography using n-hexane:AcOEt (2:3) as a mobile phase to yield 36 mg (48%) of product C14. The residue corresponded to starting product.

'H NMR (300 MHz, CDC13) S 7.00 (1H, dd, J1= 1. 4, J2= 7.0 Hz, H-6) ;
6.46 (1H, d, J= 1. 4 Hz, H-1) ; 6.29 (1H, d, J= 7.2 Hz, H-7) ; 3.56 (3H, s, OMe) ; 3.13 (s, N-CH3) ; 3. 00 (s, N-CH3) ; 2.17 (3H, s, Me-23); 1.46 (3H, s, Me-25); 1.26 (3H, s, Me-26); 1.17 (3H, s, Me-30); 1.09 (3H, s, Me-28) ; 0.54 (3H, s, Me-27) . 13C NMR (75 MHz, CDC13) 6 10.97 (c, C-23); 18.09 (c, C-27); 21.63 (c, C-26);
28.39 (t, C-15) ; 29.38 (t, C-12) ; 29. 67 (t, C-21) ; 30.29 (s, C-17); 30.61 (t, C-19); 31.34 (c, C-28); 32.40 (c, C-30); 33.45 (t, C-11) ; 34.49 (t, C-22); 36.15 (t, C-16); 36.57 (c, N-CH3) ;
36.58(c, N-CH3); 37.99 (c, C-25); 38.99 (s, C-13); 40.14 (s, C-20) ; 42.23 (s, C-9) ; 44.07 (d, C-18) ; 44.87 (s, C-14) ; 51.34 (q, OCH3); 117.5 (d, C-7) 122.9 (d, C-1) ; 126.5 (s, C-4) ; 133.1 (s, C-5); 134.5 (d, C-6); 143.0 (s, C-3); 153.9 (s, OCON); 162.6 (s, C-10); 170.8 (s, C-8); 178.3 (s, C-2) ; 178.4 (s, C-29) . High resolution MS Calculated for C33H45N05 535.3298, observed 535.3294.
EX VIVO ASSAYS OF HUMAN CHOK ACTIVITY
Recombinant human alpha-1 choline kinase expressed in E.
coli in the assay of the buffer (100 mM Tris-HC1 pH 8.0, 100 mM
MgC12, 10 mM ATP and 200 M of choline in the presence of methyl [ 14C ] -choline chloride (50-60 Ci/mmol) were used for the ex vivo assays. The reactions were carried out at 37 C for 30 min and were stopped with trichloroacetic acid cooled with ice at a final 16% concentration. The samples were washed with diethyl ether saturated with water and were lyophilized. The hydrophilic choline derivatives were resolved in thin layer chromatography plates according to a described process [Ramirez, A., Penalva, V., Lucas, L., Lacal, J.C. Oncogene 21, 937-946 (2002)].
These assays were carried out with the compounds of the invention C3, C7, C8, C9, C10, C12 and C14 as well as with another eight compounds known in the state of the art (IS 2 117 950). The results are summarized in table I.
From the obtained results it is concluded that the compounds of the invention allow considerably and selectively reducing the activity of the choline kinase (ChoK) enzyme in cell models.
CELL PROLIFERATION ASSAYS

HT-29 cells were seeded in 24-well plates (35 H 103 cells/well) and were incubated for 24 h. Then, the cells were treated with different concentrations of ChoK inhibitors in the usual culture medium. Three days later, the wells were aspirated and both fresh medium and more drug was added, and the cells were kept for 3 more days. The quantification of the cells remaining in each well was carried out by means of the Crystal Violet method [Gillies, R. J., Didier, N., Denton, M. Anal.
Biochem. 159, 109-113 (1986)], with some modifications [Hernandez-Alcoceba, R., Saniger, L., Campos, J., Nunez, M. C., Khaless, F., Gallo, M. A., Espinosa, A., Lacal, J. C. Oncogene, 15, 2289-2301 (1997)]. Briefly, the cells were washed with TD
buffer and were fixed with 1% glutaraldehyde for 15 min. After washing again with TD, the cell nuclei were stained with 0.1%
Crystal Violet for at least 30 min and were washed 3 times with distilled water. The adsorbed dye was resuspended in 10% acetic acid and the absorbance at 595 nm was determined in a spectrometer. The obtained results are summarized in the form of an IC50 value, i.e. the concentration of the compound required to cause a 50% inhibition. This value is determined by the iterative adjustment of the curve. Two values were determined for each point of the curve, the experiment was repeated two or three times and the average values were estimated. In the few cases in which the two values differed by more than 50%, a third experiment was carried out to determine the real value. The IC50 value as a measurement of the potency is used to relate the biological activity of the compounds with their chemical structure.

These assays are carried out with the compounds of the invention C3, C7, C8, C9, C10, C12 and C14 as well as with another eight compounds known in the state of the art (ES 2 117 950). The results are summarized in table I.
The following table summarizes the results obtained in the conducted assays and which are shown as an example.

Table I

IC50 ex vivo No. Code IC50 HT-2 9( M) (NM) 3.3 13.6 % F, 5.3 =1 4 8.8 1 11.2 ~ .
7.4 11 7.1 11.3 r-r1ih, 1 1, amr-.tl1...,;1-11,1% l11};,1 4.1 r,.r :};H, ',H ri l 4, (;b, ; , 11, 11};, 14a -am:-.t1 :1-l, 1)- li 4.8 11.1 1~;a, 1~};, 1 1 1 , 14;a-t-.t - , 1- a1 -:,1- -pi -.i - ;-al) fii : a-~i~1 in-filj~,rl r-. -t 1 ~_i 1~'Trl-5.2 4 , ~};, :õ , 11, 1 1}_;, 1 1;a-m: tlr,;l li _ :

1;; li};, 1 11, 11 tit - _i!=1 1':_: r,l 4, };, 11, 11};, 14a --_ m-t1 l l ) li _ _ 14.6 17.0 114 , 1 1a ti-t i 1 r Cl -r;i ri yl dim-th,rl a -}"amir t 1% 1 1, };, , 11, 12};, 14 1 :- _xaint lr%1-'l li 8.6 7.2 11_=i, 11 14 , 14 1) i iili _ i 1 t 114-} m 1 il - 1:__ }, };, 11, 11};, 1 1a -rrn: t11-,71-10.8 12.1 14 , 14 i 1c-},H, H r i n 1( li:_ r:
14 m i~o (1 -;
4_i, , 11},, 1 1i-1 :-_ lrn:-t1i,-1-, 11- li 4.7 11.3 1, 1, 1. , , , r.; , 11, 1%
}", 1},, 1 1, 14 a, 1};-t-t ~l1 a1 -: 1 .- -r,i -r - 1-;l) z=: ii i= i 1 t 1r 1 } m 1( 1 ;-1 llt;, 14 tl-1-11- li 1, 4 1 1 1 2.1 4.1 },,1 11,11; 11};-t t 1. 17 ,1 -r;i 1--,7 1 -tlj 1 lz= iiii:= a _ i 1 t From the data of table I it is observed that the compounds of the present invention have similar antiproliferative values against cells derived from cultured tumors.

Claims (71)

1.- Use of a compound of formula (I):

where:

R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; an OCOR group, where R is (CH2)2COOH or (CH2)2CO2CH2CH3; or each pair can form a (C=O) group together with the carbon to which they are attached;
R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV)(R V) amino, where R IV and R V are independently hydrogen or a C1-C12 alkyl group); a (CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group;
the bond means a double bond or a single bond;
and where the tricyclic structure is selected from the following structures:

where:

R13, R14, R15, R16, R21, R22 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; a N(R VI)(R VII) amino group, where R VI and R VII are independently hydrogen or a C1-C12 alkyl group; an OCOR VIII group, where R VIII is (CH2)2COOH or (CH2)2CO2CH2CH3; or each pair can form a (C=O) group together with the carbon to which they are attached or each pair can form a (C=O) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
R18 and R18' are independently hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX (where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X)(R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl) or trifluoromethyl;
R19, R19', R20 and R20' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII)(R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen;

or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof, in the manufacture of a medicament for the prevention and/or treatment of ChoK mediated disease or condition.
2.- Use according to claim 1 wherein the compound of formula (I) is a compound of formula (Ia):

where R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; an OCOR group, where R is (CH2)2COOH or (CH2)2CO2CH2CH3; or each pair can form a (C=O) group together with the carbon to which they are attached;
R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV) (R V) amino, where R IV and R V are independently hydrogen or a C1-C12 alkyl group); a (CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R14, R15 and R16 are independently hydrogen; hydroxyl;
halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R VI)(R VII) amino group, where R VI and R VII are independently hydrogen or a C1-C12 alkyl group; an OCOR VIII group, where R VIII is (CH2)2COOH or (CH2)2CO2CH2CH3; or each pair can form a (C=O) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
R18 is hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX
(where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X)(R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12alcoxyl); or trifluoromethyl;
R19 is hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XIII)(R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3);
or trifluoromethyl; and the bond means a double bond or a single bond.
3.- Use according to claim 2 wherein the compound of formula (Ia) is a compound of formula (Ia'):

where R5 is hydroxyl or a OCOR group where R is (CH2)2COOH or (CH2)2CO2CH2CH3;
R7 and R8 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R12 is independently hydrogen or a halogen; and R19 is hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XIII)(R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3);
or trifluoromethyl; and the bond means a double bond or a single bond.
4.- Use according to claim 3 wherein the compound of formula (Ia') is:

- 3,9-Dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- Acetic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl propionic acid ester;

- Dodecanoic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dimethyl-carbamic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Nicotinic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;
- 4-bromo-(9-hydroxy-6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl) benzoic acid ester;
- 14-Bromo-3,7,9-trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 12-bromo-9-hydroxy-6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl dimethyl-carbamic acid ester;
- 4-bromo-(12-bromo-9-hydroxy-6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl) benzoic acid ester;
- 12-bromo-3,9-dihydroxy-6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 3,9,10-trihydroxy-6b,8a,11,12b,14a-hexamethyl-7,8,8a,9,10,11,12,12a,12b,13,14,14a-dodecahydro-6bH-picene-2-one;

- Succinic acid mono-(10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl) ester;

- Succinic acid ethyl ester 10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl ester.
5.- Use according to claim 2 wherein the compound of formula (Ia) is a compound of formula (Ia''):

where:
R7 and R8 are independently hydrogen, hydroxyl, halogen, substituted or non-substituted C1-C12 alkyl, substituted or non-substituted C6-C10 aryl, a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group, or each pair can form a (C=O) group together with the carbon to which they are attached;
R15 is hydrogen or halogen;
R19 is hydrogen, substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XIII)(R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3);
or trifluoromethyl; and the bond means a double bond or a single bond.
6.- Use according to claim 5 wherein the compound of formula (Ia'') is:

-14-bromo-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-
7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl acetic acid ester;

-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl nicotinic acid ester;
-3,10-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,9,10,11,12,12a,12b,13,14,14a-dodecahydro-6bH-picene-2-one;

-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,12a,12b,13,14,14a-octahydro-6bH,9H-picene-2,10-dione 7.- Use according to claim 2 wherein the compound of formula (Ia) is a compound of formula (Ia"'):

where:
R7 is hydrogen, hydroxyl, halogen, substituted or non-substituted C1-C12 alkyl, substituted or non-substituted C6-C10 aryl, or a N(R')(R") amino group, where R' and R" are independently hydrogen or a C1-C12 alkyl group; and R19 is substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl;
with the proviso that when R19 is hydrogen, R7 is not hydrogen.
8.- Use according to claim 7 wherein the compound of formula (Ia"') is:

- 10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3,10-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 2,4a,6a,9,12b,14a-hexamethyl-11-oxo-10-propionyloxy-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- (10-dimethylcarbamoyloxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic) acid methyl ester
9.- Use according to clam 1 wherein the compound of formula (I) is a compound of formula (Ib):

where:

R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R" are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV) (R V) amino, where R IV and R V are independently hydrogen or a C1-C12 alkyl group); a (CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R14, R15, R16, R21, R22 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; a N(R VI) (R VII) amino group, where R VI and R VII are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
R18 is hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX
(where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl); or trifluoromethyl;
R19 and R20 are independently hydrogen, substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen;
hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group) ; a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl; and the bond means a double bond or a single bond.
10.- Use according to claim 9 wherein the compound of formula (Ib) is a compound of formula (Ib'):

where:
R19 and R20 are independently substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV
are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl.
11.- Use according to claim 10 wherein the compound of formula (Ib') is 4-nitro-(3-dimethylcarbamoyloxy-5,9-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-10-oxo-5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-2-yl) benzoic acid ester.
12.- Use according to claim 9 wherein the compound of formula (Ib) is a compound of formula (Ib"):

where:
R18 is hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX
(where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl); or trifluoromethyl;
R19 is hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group) ; a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3);
or trifluoromethyl;
R23 is hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R VI) (R VII) amino group, where R VI and R VII are independently hydrogen or a C1-C12alkyl group.
13.- Use according to claim 12 wherein the compound of formula (Ib'') is:

- 7,10,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 9-formyl-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 11-hydroxy-10-(2-methoxy-ethoxymethoxy)-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester
14.- Use according to claim 1 wherein the compound of formula (I) is a compound of formula (Ic):

where:

R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R" are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV) (R V) amino, where R IV and R V are independently hydrogen or a C1-C12 alkyl group); a (CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group;

R13, R14, R15, R16, R21 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; a N(R VI) (R VII) amino group, where R VI and R VII are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R18 is hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX
(where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-Cl2 alcoxyl); or trifluoromethyl;

R19 and R20 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen;
hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl; and the bond means a double bond or a single bond.
15. Use according to claim 14 wherein the compound of formula (Ic) is a compound of formula (Ic'):

where:
R19 and R20 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen;
hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3) or trifluoromethyl; and the bond means a double bond or a single bond.
16.- Use according to claim 15 wherein the compound of formula (Ic') is:

- 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-1,4,4a,5,6,6a,13,14,14a,14b-decahydro-2H-picene-3-one;
- 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-4a,5,6,6a,13,14,14a,14b-octahydro-4H-picene-3-one.
17.- Use according to claim 14 wherein the compound of formula (Ic) is a compound of formula (Ic"):

where:
R19 and R20 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen;
hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl.
18.- Use according to claim 17 wherein the compound of formula (Ic") is 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-1,2,3,4,4a,5,6,6a,13,14,14a,14b-dodecahydro-picene-2-carboxylic acid methyl ester.
19.- Use according to claim 1 wherein the compound of formula (I) is a compound of formula (Id):

where:

R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R" are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV) (R V) amino, where R IV and R V are independently hydrogen or a C1-C12 alkyl group); a (CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R15, R21 and R23 are independently hydrogen; hydroxyl;
halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R VI) (R VII) amino group, where R VI and R VII are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R18 is hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX
(where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl); or trifluoromethyl;

R19, R19', R20 and R20' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or
20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen; and the bond means a double bond or a single bond.

20.- Use according to claim 19 wherein the compound of formula (Id) is a compound of formula (Id'):

where:
R5 and R6 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R") amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R19, R19', R20 and R20' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen.
21.- Use according to calim 20 wherein the compound of formula (Id') is:

- 1-bromo-9-hydroxy-4,6b,8a,11,12b,14b-hexamethyl-6b,7,8,8a,9,11,12,12a,12b,14b-decahydro-1H-picene-2,3,10-trione;

- 1-bromo-4,6b,8a,11,12b,14b-hexamethyl-6b,7,8,8a,9, 11,12,12a,12b,14b-decahydro-1H-picene-2,3,10-trione.
22.- Use according to claim 19 wherein the compound of formula (Id) is a compound of formula (Id''):

where:
R19, R19', R20 and R20' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII)(R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12) alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen.
23.- Use according to claim 22 wherein the compound of formula (Id'') is 12-bromo-2,4a,6a,9,12a,14a-hexamethyl-10,11-dioxo-1,2,3,4,4a,5,6,6a,10,11,12,12a,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester.
24.- Use according to claim 1 wherein the compound of formula (I) is a compound of formula (Ie) :

where:

R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV)(R V) amino, where R IV and R V are independently hydrogen or an alkyl group C1-C12); a carbinol group (CH2)n-OH (where n is an integer comprised between 1 and 10); or together form a methylene group;

R13, R14, R15, R16, R21 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-C10 aryl; a N(R VI)(R VII) amino group, where R VI and R VII are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R18 and R18' are independently hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX (where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl); or trifluoromethyl;
R19m R19', R20 and R20' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII)(RXIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen; and the bond means a double bond or a single bond.
25.- Use according to claim 24 wherein the compound of formula (Ie) is a compound of formula (Ie'):

where:
R18 and R18' are independently hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX (where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl) or trifluoromethyl;

R19, R19', R20 and R20' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII)(R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12) alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen.
26.- Use according to claim 25 wherein the compound of formula (Ie') is 9-hydroxy-2,4a,6a,9,12b-hexamethyl-10,11-dioxo-1,2,3,4,4a,5,6,6a,9,10,11,12b,13,14,14a,14b-hexadecahydro-picene-2-carboxylic acid methyl ester.
27.- Use according to claim 1 wherein the compound of formula (I) is a compound of formula (If):

where:

R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;

R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV)(R V) amino, where R IV and R V are independently hydrogen or a C1-C12 alkyl group); a (CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R14, R15, R21 and R23 are independently hydrogen; hydroxyl;
halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R VI)(R VIII) amino group, where R XI and R XII are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R18 and R18' are independently hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX (where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X)(R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl) or trifluoromethyl;
R19, R19', R20 and R20' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen; and the bond means a double bond or a single bond.
28.- Use according to claim 27 wherein the compound of formula (If) is a compound of formula (If'):

where:
R18 and R18' are independently hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX (where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl); or trifluoromethyl;
R19, R19', R20 and R20' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII)(R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a group C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen.
29.- Use according to claim 28 wherein the compound of formula (If') is 9-hydroxy-2,4a,6a,6b,9-hexamethyl-10,11-dioxo-1,2,3,4,4a,5,6,6a,6b,8a,9,10,11,14,14a,14b-hexadecahydro-picene-2-carboxylic acid methyl ester.
30.- Use of a compound of formula (II):

where:

R1, R2, R3, R4, R5, R6r R9r R10, R11, R12, R13, R14, R15, R16, R17, R18, R19 and R20 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R XV)(R XVI) amino group, where R XV and R XVI are independently hydrogen or a C1-C12 alkyl group; or each pair can form a carboxyl (C=O) group together with the carbon to which they are attached;
R7 and R8 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR XVII group (where R XVII
is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R XVIII)(R XIX) amino, where R XVIII and R XIX are independently hydrogen or a C1-C12 alkyl group); a (CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R21 and R24 are independently substituted or non-substituted C1-C12 alkyl; a COR XX group (where R XX is hydrogen; hydroxyl;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XXI)(R XXII) amino, where R XXI and R XXII
are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12) alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl;

R22 and R23 are:

- hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XXIII group (where R XXIII is hydrogen; hydroxyl;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XXIV) (R XXV) amino, where R XXIV and R XXV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the para position with respect to R20; or OR22' and OR23' respectively, where R22' and R23' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XXVI group (where R XXVI is hydrogen; hydroxyl;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XXVII)(R XXVIII) amino, where R XXVII and R XXVIII are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the meta position with respect to R20.
or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof, in the manufacture of a medicament for the prevention and/or treatment of a ChoK
mediated disease or condition.
31.- Use according to claim 30 wherein the compound of formula (II) is a compound of formula (IIa):

where:

R1, R2, R3, R4, R5, R6, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19 and R20 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R XV)(R XVI) amino group, where R XV and R XVI are independently hydrogen or a C1-C12 alkyl group; or each pair can form a carboxyl (C=O) group together with the carbon to which they are attached;
R7 and R8 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR XVII group (where R XVII
is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R XVIII)(R XIX) amino, where R XVIII and R XIX are independently hydrogen or a C1-C12 alkyl group); a (CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R21 and R24 are independently substituted or non-substituted C1-C12 alkyl; a COR XX group (where R XX is hydrogen; hydroxyl;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XXI)(R XXII) amino, where R XXI and R XXII
are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl;

R22 and R23 are:

- hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XXIII group (where R XXIII is hydrogen; hydroxyl;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XXIV)(R XXV) amino, where R XXIV and R XXV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the para position with respect to R20; or - OR22' and OR23' respectively, where R22' and R23' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XXVI group (where R XXVI is hydrogen; hydroxyl;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XXVII) (R XXVIII) amino, where R XXVIV and R XXVIII are independently hydrogen or a C1-C12 alkyl group); a[(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the meta position with respect to R20.
32.- Use according to claim 31 wherein the compound of formula (IIa) is a compound of formula (IIa'):

where:
R19 and R20 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R XV)(R XVI) amino group, where R XV and R XVI are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) carboxyl group together with the carbon to which they are attached;
R21 and R24 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R XXI)(R XXII) amino group, where R XXI and R XXII are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) carboxyl group together with the carbon to which they are attached;
R22 and R23 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R XXIV)(R XXV) amino group, where R XXIV
and R XXV are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) carboxyl group together with the carbon to which they are attached.
33.- Use according to claim 32 wherein the compound of formula (IIa') is 8-[2-(6,7-dihydroxy-1,5-dimethyl-naphthalen-2-yl)-ethyl]-2,4a-tetramethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-2-carboxylic acid methyl ester.
34. Use according to any one of claims 1 to 33 wherein the ChoK
mediated disease or condition to be prevented and/or treated is cancer, preferably selected from breast, lung, colorectal and pancreatic cancer.
35. Use according to any one of claims 1 to 33 wherein the ChoK
mediated disease or condition to be prevented and/or treated is a parasitic disease, more preferably caused by Plasmodium or Trypanosoma.
36. Use according to any one of claims 1 to 33 wherein the ChoK
mediated disease or condition to be prevented and/or treated is a parasitic disease, more preferably is a parasitic disease caused by a bacterial disease, preferably caused by Streptococcus.
37. Use according to any one of claims 1 to 33 wherein the ChoK
mediated disease or condition to be prevented and/or treated is a fungal disease, preferably caused by Candida.
38. A compound of formula (I):

where:

R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; an OCOR group, where R is (CH2)2COOH or (CH2)2CO2CH2CH3; or each pair can form a (C=O) group together with the carbon to which they are attached;

R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV)(R V) amino, where R IV and R V are independently hydrogen or a C1-C12 alkyl group); a (CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group;
the bond means a double bond or a single bond;
and where the tricyclic structure is selected from the following structures:

where:

R13, R14, R15, R16, R21, R22 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl;

substituted or non-substituted C6-C10 aryl; a N(R VI)(R VII) amino group, where R VI and R VII are independently hydrogen or a C1-C12 alkyl group; an OCOR VIII group, where R VIII is (CH2)2COOH or (CH2)2CO2CH2CH3; or each pair can form a (C=O) group together with the carbon to which they are attached or each pair can form a (C=O) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
R18 and R18, are independently hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX (where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X)(R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl); or trifluoromethyl;
R19, R19', R20 and R20' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII)(R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group) ; a [(C1-C12) alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen;

or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof, with the following provisos:

- when the tricyclic structure is (a) then the compound of formula (I) is not:

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid;

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3,10-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3-Hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 3,9-Dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 3,7,9-Trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 14-Bromo-3,7,9-trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;
- Succinic acid mono-(10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl) ester;

- Succinic acid ethyl ester 10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl ester;

- Acetic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dodecanoic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dimethyl-carbamic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Nicotinic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;
- 3,10-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester.
- when the tricyclic structure is (b) and R19 and R20 are independently hydrogen or an acyl group, then:

- R5 is hydroxyl; or - R21 and R22 form a C=O group together with the carbon to which they are attached and R10 is not COOH.

- when the tricyclic structure is (c) and R19 and R20 are both CH3, then R15 and R16 do not form a C=O group together with the carbon to which they are attached.
39. A compound according to claim 38 of formula (Ia):

where R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; an OCOR group, where R is (CH2)2COOH or (CH2)2CO2CH2CH3; or each pair can form a (C=O) group together with the carbon to which they are attached;
R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV)(R V) amino, where R IV and R V are independently hydrogen or a C1-C12 alkyl group); a (CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R14, R15 and R16 are independently hydrogen; hydroxyl;
halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R VI)(R VII) amino group, where R VI1 and R VII are independently hydrogen or a C1-C12 alkyl group; an OCOR VIII group, where R VIII is (CH2)2COOH or (CH2)2CO2CH2CH3; or each pair can form a (C=O) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
R18 is hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX
(where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X)(R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12alcoxyl); or trifluoromethyl;
R19 is hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XIII)(R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3);
or trifluoromethyl; and the bond means a double bond or a single bond, with the proviso that the compound of formula (Ia) is not:
- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid;

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3,10-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 3-Hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 3,9-Dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 3,7,9-Trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 14-Bromo-3,7,9-trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- Succinic acid mono-(10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl) ester;

- Succinic acid ethyl ester 10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl ester;

- Acetic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dodecanoic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dimethyl-carbamic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Nicotinic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- 3,10-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester.
40. A compound according to claim 39 of formula (Ia'):

where R5 is hydroxyl or a OCOR group where R is (CH2)2COOH or (CH2)2CO2CH2CH3;
R7 and R8 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; or each pair can form a(C=O) group together with the carbon to which they are attached;
R12 is independently hydrogen or a halogen; and R19 is hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XIII)(R X IV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3);
or trifluoromethyl; and the bond means a double bond or a single bond, with the proviso that the compound of formula (Ia') is not:
- 3,9-Dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 14-Bromo-3,7,9-trihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- Succinic acid mono-(10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl) ester;

- Succinic acid ethyl ester 10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,11-dioxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picen-4-yl ester;

- Acetic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dodecanoic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Dimethyl-carbamic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester;

- Nicotinic acid 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picen-3-yl ester.
41. A compound according to claim 40 which is:

- 9-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl propionic acid ester;

- 4-bromo-(9-hydroxy-6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl) benzoic acid ester;
- 12-bromo-3,9-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

- 12-bromo-9-hydroxy-6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl dimethyl-carbamic acid ester;
- 4-bromo-(12-bromo-9-hydroxy-6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl) benzoic acid ester;
- 3,9,10-trihydroxy-6b,8a,11,12b,14a-hexamethyl-7,8,8a,9,10,11,12,12a,12b,13,14,14a-dodecahydro-6bH-picene-2-one.
42. A compound according to claim 39 of formula (Ia''):

where:
R7 and R8 are independently hydrogen, hydroxyl, halogen, substituted or non-substituted C1-C12 alkyl, substituted or non-substituted C6-C10 aryl, a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group, or each pair can form a (C=O) group together with the carbon to which they are attached;
R15 is hydrogen or halogen;

R19 is hydrogen, substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12) alkyl-O-(C1-C12) alkyl-]n group (where n is comprised between 1 and 3);
or trifluoromethyl; and the bond means a double bond or a single bond, with the proviso that the compound of formula (Ia") is not:
- 3-Hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,9,10,11,12,12a,12b,13,14,14a-dodecahydro-6bH-picen-2-one;

- 3-Hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione.
43. A compound according to claim 42 which is:
-14-bromo-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,11,12,12a,12b,13,14,14a-decahydro-6bH,9H-picene-2,10-dione;

-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl acetic acid ester;

-4,6b,8a,11,12b,14a-hexamethyl-2,10-dioxo-2,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-3-yl nicotinic acid ester;

-3,10-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,9,10,11,12,12a,12b,13,14,14a-dodecahydro-6bH-picene-2-one;

-3-hydroxy-4,6b,8a,11,12b,14a-hexamethyl-7,8,8a,12a,12b,13,14,14a-octahydro-6bH,9H-picene-2,10-dione.
44. A compound according to claim 39 of formula (Ia"'):

where:
R7 is hydrogen, hydroxyl, halogen, substituted or non-substituted C1-C12 alkyl, substituted or non-substituted C6-C10 aryl, or a N(R')(R") amino group, where R' and R" are independently hydrogen or a C1-C12 alkyl group; and R19 is substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl;
with the proviso that the compound of formula (Ia"') is not:
- 3,10-Dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester.
45. A compound according to claim 44 which is:

- 2,4a,6a,9,12b,14a-hexamethyl-11-oxo-10-propionyloxy-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

- 10-dimethylcarbamoyloxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester.
46. A compound according to claim 38 of formula (Ib):

where:

R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV) (R V) amino, where R IV and R V are independently hydrogen or a C1-C12 alkyl group); a (CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R14, R15, R16, R21, R22 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; a N(R VI) (R VII) amino group, where R VI and R VII are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R17 is hydrogen or methyl;
R18 is hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX
(where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl); or trifluoromethyl;

R19 and R20 are independently hydrogen, substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen;
hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12) alkyl-O-(C1-C12) alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl; and the bond means a double bond or a single bond, with the proviso that when R19 and R20 are independently hydrogen or an acyl group, then:
R5 is hydroxyl; or R21 and R22 form a C=O group together with the carbon to which they are attached and R10 is not COOH.
47. A compound according to claim 46 of formula (Ib'):

where:
R19 and R20 are independently substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV
are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl.
48. A compound according to claim 47 which is 4-nitro-(3-dimethylcarbamoyloxy-5,9-dihydroxy-4,6b,8a,11,12b,14a-hexamethyl-10-oxo-5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a-tetradecahydro-picene-2-yl) benzoic acid ester.
49. A compound according to claim 46 of formula (Ib''):

where:
R18 is hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX
(where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl); or trifluoromethyl;
R19 is hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3);
or trifluoromethyl;
R23 is hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R VI) (R VII) amino group, where R VI and R VII are independently hydrogen or a C1-C12alkyl group.
50. A compound according to claim 49 which is:

- 7,10,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;

9-formyl-10,11-dihydroxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester;
11-hydroxy-10-(2-methoxy-ethoxymethoxy)-2,4a,6a,9,12b,14a-hexamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester.
51. A compound according to claim 38 of formula (Ic):

where:

R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R" are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV) (R V) amino, where R IV and R V are independently hydrogen or a C1-C12 alkyl group); a (CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group;
R13, R14, R15, R16, R21 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; a N(R VI) (R VII) amino group, where R VI and R VII are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R18 is hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX
(where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl); or trifluoromethyl;
R19 and R20 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen;
hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl; and the bond means a double bond or a single bond, with the proviso that when R19 and R20 are both CH3, then R15 and R16 do not form a C=O group together with the carbon to which they are attached.
52. A compound according to claim 51 of formula (Ic'):

where:
R19 and R20 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen;
hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3) or trifluoromethyl; and the bond means a double bond or a single bond.
53. A compound according to claim 52 which is:

- 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-1,4,4a,5,6,6a,13,14,14a,14b-decahydro-2H-picene-3-one;
- 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-4a,5,6,6a,13,14,14a,14b-octahydro-4H-picene-3-one.
54. A compound according to claim 51 of formula (Ic"):

where:
R19 and R20 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen;
hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl.
55. A compound according to claim 54 which is 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-1,2,3,4,4a,5,6,6a,13,14,14a,14b-dodecahydro-picene-2-carboxylic acid methyl ester.
56. A compound according to claim 38 of formula (Id):

where:

R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV) (R V) amino, where R IV and R V are independently hydrogen or a C1-C12 alkyl group); a (CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R15, R21 and R23 are independently hydrogen; hydroxyl;
halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R VI) (R VII) amino group, where R VI and R VII are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R18 is hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX
(where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-Cl2 alcoxyl); or trifluoromethyl;

R19, R19', R20 and R20' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen; and the bond means a double bond or a single bond.
57. A compound according to claim 56 of formula (Id'):

where:
R5 and R6 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R") amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; or each pair can form a (C=O) group together with the carbon to which they are attached;
R19, R19', R20 and R20' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12)alkyl-O-(C1-C12)alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen.
58. A compound according to claim 57 which is:

- 1-bromo-9-hydroxy-4,6b,8a,11,12b,14b-hexamethyl-6b,7,8,8a,9,11,12,12a,12b,14b-decahydro-1H-picene-2,3,10-trione;

- 1-bromo-4,6b,8a,11,12b,14b-hexamethyl-6b,7,8,8a,9,11,12,12a,12b,14b-decahydro-1H-picene-2,3,10-trione.
59. A compound according to claim 56 of formula (Id''):
where:
R19, R19', R20 and R20, are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group) ; a [(C1-C12) alkyl-O- (C1-C12) alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 and R25 are independently hydrogen, hydroxyl or halogen.
60. A compound according to claim 59 which is 12-bromo-2,4a,6a,9,12a,14a-hexamethyl-10,11-dioxo-1,2,3,4,4a,5,6,6a,10,11,12,12a,14a,14b-tetradecahydro-picene-2-carboxylic acid methyl ester.
61. A compound according to claim 38 of formula (Ie):
where:

R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;
R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV) (R V) amino, where R IV and R V are independently hydrogen or an alkyl group C1-C12) ; a carbinol group (CH2)n-OH (where n is an integer comprised between 1 and 10); or together form a methylene group;

R13, R14, R15, R16, R21 and R23 are independently hydrogen;
hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; a N(R VI) (R VII) amino group, where R VI and R VII are independently hydrogen or a C1-C12 alkyl group; or each pair can form a(C=O) group together with the carbon to which they are attached;
R18 and R18' are independently hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX (where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl); or trifluoromethyl;
R19, R19', R20 and R20' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group) ; a [(C1-C12) alkyl-O- (C1-C12) alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen; and the bond ~ means a double bond or a single bond.
62. A compound according to claim 61 of formula (Ie'):
where:
R18 and R18' are independently hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX (where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R IX are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl) or trifluoromethyl;

R19, R19', R20 and R20, are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group) ; a [(C1-C12) alkyl-O- (C1-C12) alkyl-] n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen.
63. A compound according to claim 62 which is 9-hydroxy-2,4a,6a,9,12b-hexamethyl-10,11-dioxo-1,2,3,4,4a,5,6,6a,9,10,11,12b,13,14,14a,14b-hexadecahydro-picene-2-carboxylic acid methyl ester.
64. A compound according to claim 38 of formula (If):
where:

R1, R2, R3, R4, R5, R6, R7, R8, R11 and R12 are independently hydrogen; hydroxyl; halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R')(R'') amino group, where R' and R'' are independently hydrogen or a C1-C12 alkyl group; or each pair can form a(C=0) group together with the carbon to which they are attached;

R9 and R10 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR''' group (where R''' is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R IV) (R V) amino, where R IV and R V are independently hydrogen or a C1-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10); or together form a methylene group, R13, R14, R15, R21 and R23 are independently hydrogen; hydroxyl;
halogen; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R41) (R411) amino group, where R VI and R VII are independently hydrogen or a C1-C12 alkyl group; or each pair can form a(C=O) group together with the carbon to which they are attached;
R18 and R18' are independently hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX (where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl) or trifluoromethyl;
R19, R19', R20 and R20, are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group) ; a [(C1-C12) alkyl-O- (C1-C12) alkyl-]n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen; and the bond ~ means a double bond or a single bond.
65. A compound according to claim 64 of formula (If'):

where:
R18 and R18' are independently hydrogen; hydroxyl; halogen; C1-C12 alkyl; C6-C10 aryl; COR IX (where R IX is hydrogen; hydroxyl; C1-C12 alkyl; N(R X) (R XI) amino, where R X and R XI are independently hydrogen or a C1-C12 alkyl group; or C1-C12 alcoxyl); or trifluoromethyl;
R19, R19', R20 and R20, are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XII group (where R XII is hydrogen; hydroxyl; substituted or non-substituted Cl-C12 alkyl;
substituted or non-substituted C6-C10 aryl; or N(R XIII) (R XIV) amino, where R XIII and R XIV are independently hydrogen or a C1-C12 alkyl group) ; a [(C1-C12) alkyl-O- (C1-C12) alkyl-] n group (where n is comprised between 1 and 3); trifluoromethyl; or each 19-19' or 20-20' pair can form a group C=O group together with the carbon to which they are attached;
R24 is hydrogen, hydroxyl or halogen.
66. A compound according to claim 65 which is the 9-hydroxy-2,4a,6a,6b,9-hexamethyl-10,11-dioxo-1,2,3,4,4a,5,6,6a,6b,8a,9,10,11,14,14a,14b-hexadecahydro-picene-2-carboxylic acid methyl ester.
67. A compound of formula (II):

where:

R1, R2, R3, R4, R5, R6, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19 and R20 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R XV) (R XVI) amino group, where R XV and R XVI are independently hydrogen or a C1-C12 alkyl group; or each pair can form a carboxyl (C=O) group together with the carbon to which they are attached;
R7 and R8 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR XVII group (where R XVII
is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R XVIII) (R XIX) amino, where R XVIII and R XIX are independently hydrogen or a C1-C12 alkyl group) ; a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10) ; or together form a methylene group, R21 and R24 are independently substituted or non-substituted C1-C12 alkyl; a COR XX group (where R XX is hydrogen; hydroxyl;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XXI) (R XXII) amino, where R XXI and R XXII
are independently hydrogen or a C1-C12 alkyl group); a [(C1-C12) alkyl-O- (C1-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl;

R22 and R23 are:

- hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XXIII group (where R XXIII is hydrogen; hydroxyl;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XXIV) (R XXV) amino, where R XXIV and R XXV are independently hydrogen or a C1-C12 alkyl group) ; a[(C1-C12) alkyl-O- (C1-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the para position with respect to R20; or - OR22' and OR23' respectively, where R22' and R23' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XXVI group (where R XXVI is hydrogen; hydroxyl;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XXVIII) (R XXVIII) amino, where R XXVII and R XXVIII are independently hydrogen or a C1-C12 alkyl group) ; a[(C1-C12) alkyl-O- (C1-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the meta position with respect to R20.
or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof.
68. A compound according to claim 67 of formula (IIa):
where:

R1, R2, R3, R4, R5, R6, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19 and R20 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R XV) (R XVI) amino group, where R XV and R XVI are independently hydrogen or a C1-C12 alkyl group; or each pair can form a carboxyl (C=O) group together with the carbon to which they are attached;
R7 and R8 are independently hydrogen; substituted or non-substituted C1-C12 alkyl; C6-C10 aryl; a COR XVII group (where R XVII

is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; O-C1-C12 alkyl;
or N(R XVIII) (R XIX) amino, where R XVIII and R XIX are independently hydrogen or a C1-C12 alkyl group); a(CH2)n-OH carbinol group (where n is an integer comprised between 1 and 10) ; or together form a methylene group, R21 and R24 are independently substituted or non-substituted C1-C12 alkyl; a COR XX group (where R XX is hydrogen; hydroxyl;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XXI) (R XXII) amino, where R XXI and R XXII
are independently hydrogen or a C1-C12 alkyl group); a[(C1-C12) alkyl-O- (C1-C12) alkyl-]n group (where n is comprised between 1 and 3); or trifluoromethyl;

R22 and R23 are:

- hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XXIII group (where R XXIII is hydrogen; hydroxyl;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XXIV) (R XXV) amino, where R XXIV and R XXV are independently hydrogen or a C1-C12 alkyl group) ; a[(C1-C12) alkyl-O- (C1-C12) alkyl-] n group (where n is comprised between 1 and 3); or trifluoromethyl when R24 is in the para position with respect to R20; or OR22' and OR23' respectively, where R22' and R23' are independently hydrogen; substituted or non-substituted C1-C12 alkyl; a COR XXVI
group (where R XXVI is hydrogen; hydroxyl; substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; or N(R XXVII) (R XXVIII) amino, where R XXVII and R XXVIII are independently hydrogen or a C1-C12 alkyl group) ; a[(C1-C12) alkyl-O- (C1-C12) alkyl-] n group (where n is comprised between 1 and 3) ;
or trifluoromethyl when R24 is in the meta position with respect to R20.
69. A compound according to claim 68 of formula (IIa'):

where:
R19 and R20 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R XV) (R XVI) amino group, where R XV and R XVI are independently hydrogen or a C1-C12 alkyl group; or each pair can form a(C=O) carboxyl group together with the carbon to which they are attached;
R21 and R24 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C1-C12 alkyl; substituted or non-substituted C6-C10 aryl; a N(R XXI) (R XXII) amino group, where R XXI and R XXII are independently hydrogen or a C1-C12alkyl group; or each pair can form a(C=O) carboxyl group together with the carbon to which they are attached;
R22 and R23 are independently hydrogen; hydroxyl; halogen;
substituted or non-substituted C XXIV) (R XXV) amino group, where R XXIV
and R XXV are independently hydrogen or a C1-C12 alkyl group; or each pair can form a(C=O) carboxyl group together with the carbon to which they are attached.
70.- A pharmaceutical composition which comprises a compound of formula (I) or (II) as defined in any one of claims 38 to 69 or mixtures thereof, or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof together with a pharmaceutically acceptable carrier, adjuvant or vehicle for the administration to a patient.
71.- A compound as defined in any one of claims 38 to 69 or mixtures thereof, or a pharmaceutically acceptable salt, derivative, prodrug, solvate or stereoisomer thereof for use in the treatment of a ChoK mediated disease or condition.
CA002635318A 2005-12-30 2006-12-29 Triterpenequinone and triterpenephenol derivatives and their application for the treatment of tumors and parasitic diseases Abandoned CA2635318A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
ES200503263A ES2277568B1 (en) 2005-12-30 2005-12-30 DERIVATIVES OF TRITERPENOQUINONA AND TRITERPENOFENOLES AND ITS APPLICATION FOR THE TREATMENT OF TUMORS AND PARASITARY DISEASES.
ESP200503263 2005-12-30
PCT/EP2006/070276 WO2007077203A2 (en) 2005-12-30 2006-12-29 Triterpenequinone and triterpenephenol derivatives and their application for the treatment of tumors and parasitic diseases

Publications (1)

Publication Number Publication Date
CA2635318A1 true CA2635318A1 (en) 2007-07-12

Family

ID=37946257

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002635318A Abandoned CA2635318A1 (en) 2005-12-30 2006-12-29 Triterpenequinone and triterpenephenol derivatives and their application for the treatment of tumors and parasitic diseases

Country Status (11)

Country Link
EP (1) EP1976533A2 (en)
JP (1) JP2009522239A (en)
KR (1) KR20080083044A (en)
CN (1) CN101351211A (en)
AU (1) AU2006334359A1 (en)
BR (1) BRPI0620845A2 (en)
CA (1) CA2635318A1 (en)
ES (1) ES2277568B1 (en)
MX (1) MX2008008556A (en)
RU (1) RU2008131311A (en)
WO (1) WO2007077203A2 (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2007012668A (en) 2005-04-13 2008-03-11 Consejo Superior Investigacion In vitro cancer therapy compound identification method.
WO2009026163A1 (en) * 2007-08-17 2009-02-26 Burnham Institute For Medical Research Compositions and methods for inhibiting growth and metastasis of melanoma
CN101434635B (en) * 2007-11-16 2012-05-16 上海华拓医药科技发展股份有限公司 Water-soluble phenolic triterpenoid with antineoplastic activity and preparation thereof
US20100068302A1 (en) * 2008-09-17 2010-03-18 Traslational Cancer Drugs Pharma, S.L. Methods and compositions for the treatment of cancer
WO2010049173A1 (en) * 2008-10-31 2010-05-06 Cenix Bioscience Gmbh Use of inhibitors of host kinases for the treatment of infectious diseases
JP2013536203A (en) * 2010-08-23 2013-09-19 スーチョウ・ニューファーマ・カンパニー・リミテッド Specific chemical components, compositions and methods
EP3364956A4 (en) 2015-10-23 2019-05-01 ERX Pharmaceuticals, Inc. Analogs of celastrol
US10808005B2 (en) 2016-07-04 2020-10-20 Ixmedicine (Xiamen) Biological Technology Company Limited Ligand for orphan nuclear receptor Nur77 and uses thereof
WO2018019681A1 (en) 2016-07-25 2018-02-01 Nerviano Medical Sciences S.R.L. Purine and 3-deazapurine analogues as choline kinase inhibitors
EP3652177A1 (en) 2017-07-11 2020-05-20 Nerviano Medical Sciences S.r.l. Pyrazolo-quinazoline derivatives as choline kinase inhibitors
WO2020257658A1 (en) 2019-06-20 2020-12-24 University Of Iowa Research Foundation Nanoparticles comprising quinone w methides and compositions for use
CN113827599A (en) * 2021-09-23 2021-12-24 天津国际生物医药联合研究院 Potential application of demethylzelaronal in resisting dengue virus infection
CN116023426A (en) * 2022-12-30 2023-04-28 上海海洋大学 Norzeranal derivative and application thereof in preparation of anticancer drugs

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4328309A (en) * 1980-07-02 1982-05-04 The United States Of America As Represented By The Secretary Of The Department Of Health & Human Services Method for producing tripdiolide, triptolide and celastrol
DE4117854A1 (en) * 1991-05-31 1992-12-03 Wiemann Wolfram Lipoxygenase inhibiting Celastroloid(s) - used for treating rheumatism, malaria, tumours or bacterial infection
US5650167A (en) * 1995-11-16 1997-07-22 Dawa Incorporated Method and composition for treating hepatitis B
ES2117950B1 (en) 1996-08-02 1999-09-16 Univ Granada NEW COMPOUNDS THAT BLOCK THE BIOSYNTHESIS OF PHOSPHORYLCHOLINE AND ITS USE AS A SECOND MESSENGER IN CELL PROLIFERATION.
CN1155610C (en) * 2002-11-05 2004-06-30 浙江大学 Pristimerin series dorivative possessing antioxidation and antitumour activity and its synthesis method
US20040220267A1 (en) * 2003-02-07 2004-11-04 Devlin J. P. Derivatives of pentacyclic nortriterpene quinone methides as compounds useful in the treatment of inflammatory, neurodegenerative, and neoplastic diseases

Also Published As

Publication number Publication date
JP2009522239A (en) 2009-06-11
ES2277568A1 (en) 2007-07-01
ES2277568B1 (en) 2008-04-01
EP1976533A2 (en) 2008-10-08
WO2007077203A2 (en) 2007-07-12
AU2006334359A1 (en) 2007-07-12
KR20080083044A (en) 2008-09-12
BRPI0620845A2 (en) 2011-11-22
WO2007077203A3 (en) 2007-08-30
AU2006334359A2 (en) 2008-08-07
CN101351211A (en) 2009-01-21
MX2008008556A (en) 2008-09-26
RU2008131311A (en) 2010-02-10

Similar Documents

Publication Publication Date Title
CA2635318A1 (en) Triterpenequinone and triterpenephenol derivatives and their application for the treatment of tumors and parasitic diseases
Cao et al. Synthesis, acute toxicities, and antitumor effects of novel 9-substituted β-carboline derivatives
KR19980702414A (en) Benzopyran-containing compounds and methods of using them
Luo et al. Oridonin derivatives as potential anticancer drug candidates triggering apoptosis through mitochondrial pathway in the liver cancer cells
CN109134586B (en) Tripterine derivative and application thereof
CN105348219B (en) Curcumin analogue and its preparation and application
US8299125B2 (en) Water-soluble triterpenephenol compounds having antitumor activity and the preparation thereof
JP6779318B2 (en) Anti-metastatic 2H-selenopheno [3,2-h] chromen, their synthesis, and how to use the drug
Ferlin et al. Pyrrolo-quinoline derivatives as potential antineoplastic drugs
CA3169315A1 (en) Glucose triptolide conjugates and uses thereof
Li et al. Synthesis, antitumor activity evaluation and mechanistic study of novel hederacolchiside A1 derivatives bearing an aryl triazole moiety
WO2007076704A1 (en) Aryl dihydro-naphthalene compounds, their preparation and their use as akt inhibitor for the prevention and treatment of cancer
CN110156822B (en) Naphthol-phenylboronic acid compound and preparation method and application thereof
Ju et al. Design and synthesis of novel mitochondria-targeted CDDO derivatives as potential anti-cancer agents
CA2741096C (en) Triterpenoid 2-deoxy glycosides, method of preparation thereof and use thereof as medicaments
Gao et al. Three new alkaloids from Veratrum grandiflorum Loes with inhibition activities on Hedgehog pathway
US7732493B2 (en) 2-substituted D-homo-estra-1,3,5(10)-trienes as inhibitors of 17β-hydroxy steroid dehydrogenase type 1
Feng et al. Scaffold hopping of celastrol provides derivatives containing pepper ring, pyrazine and oxazole substructures as potent autophagy inducers against breast cancer cell line MCF-7
Wang et al. Synthesis, anticancer evaluation and mechanism studies of novel indolequinone derivatives of ursolic acid
Güzelcan et al. Synthesis of new derivatives of boehmeriasin A and their biological evaluation in liver cancer
US6566341B1 (en) Derivative of isoindigo, indigo and indirubin for the treatment of cancer
Kang et al. Discovery of a novel water-soluble, rapid-release triptolide prodrug with improved drug-like properties and high efficacy in human acute myeloid leukemia
Komissarova et al. New Conjugates of Betulin with 2-Aminoethanesulfonic Acid
CZ282473B6 (en) Bis(phenyl)ethane derivative, process of its preparation, the derivative as a medicament and pharmaceutical composition in which said derivative is comprised
CN112279863A (en) Conjugate of Hsp90 inhibitor and camptothecin derivative as well as preparation method and application thereof

Legal Events

Date Code Title Description
FZDE Discontinued