AR047748A1 - DERIVATIVES OF 3,5 - DIOXO - (2H, 4H) - 1,2,4 - TRIAZINA ACTIVATORS OF PPAR ALFA AND / OR GAMMA RECEPTORS, THEIR PREPARATION, THEIR USE IN PHARMACEUTICAL COMPOSITIONS AND THEIR USE IN THE TREATMENT OF METABOLIC DISORDERS. - Google Patents

DERIVATIVES OF 3,5 - DIOXO - (2H, 4H) - 1,2,4 - TRIAZINA ACTIVATORS OF PPAR ALFA AND / OR GAMMA RECEPTORS, THEIR PREPARATION, THEIR USE IN PHARMACEUTICAL COMPOSITIONS AND THEIR USE IN THE TREATMENT OF METABOLIC DISORDERS.

Info

Publication number
AR047748A1
AR047748A1 ARP050100598A ARP050100598A AR047748A1 AR 047748 A1 AR047748 A1 AR 047748A1 AR P050100598 A ARP050100598 A AR P050100598A AR P050100598 A ARP050100598 A AR P050100598A AR 047748 A1 AR047748 A1 AR 047748A1
Authority
AR
Argentina
Prior art keywords
formula
connector
alkyl
resin
compounds
Prior art date
Application number
ARP050100598A
Other languages
Spanish (es)
Original Assignee
Pf Medicament
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 Pf Medicament filed Critical Pf Medicament
Publication of AR047748A1 publication Critical patent/AR047748A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D253/075—Two hetero atoms, in positions 3 and 5
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Dermatology (AREA)
  • Cardiology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Compuestos activadores de los receptores PPAR alfa y/o gamma y se utilizan para fabricar composiciones farmacéuticas y medicamentos para el tratamiento de trastornos metabolicos tales como diabetes, obesidad, dislipidemia y síndrome metabolico. Reivindicacion 1: Derivados de 3,5-dioxo-(2H,4H)-1,2,4-triazina de las formulas generales (1) y (2) en las cuales R1 representa H, un radical alquilo C1-6, alcoxi o alquenilo lineal o ramificado, un radical cicloalquilo C3 o C5-6, un radical fenil alquilo C1-2 o un radical fenilo (el anillo de fenilo está opcionalmente sustituido con uno o más grupos tales como alquilo C1-4, alcoxi C1-4, nitrilo, nitro, halogeno o trifluorometilo), un heterociclo tiofen-2-ilo, una alquilamina C1- 7 secundaria, o una cicloalquilamina C5-6, o un halogeno; R2 representa H, un alquilo C1-7 lineal o ramificado o un radical alquenilo, o uno de los siguientes radicales: alquilo C1-5 sustituido con grupos tales como trifluorometilo, monofluoroetilo o polifluoroetilo, cicloalquilo C5-6 nitrilo, benzodioxan-2-ilo, ftalimida, piridinilo, 2,2,2-trifluoroacetilamino, alcoxi C1-4-carbonilvinilo, hidroxicarbonilvinilo, alcoxicarbonilo C1-4, carboxilato, tiofen-2-carbonilo, indolilo, fenilcarbamoilo (para lo cual el anillo de fenilo está opcionalmente sustituido con uno o más grupos tales como alquilo C1-2 o nitro), alcoxi C1-4 o alcoxialquilo (C1-4 para el alcoxi, C2-4 para el alquilo), feniloxi o benciloxi o fenilo o benzhidrilo (para lo cual el anillo de fenilo está opcionalmente sustituido con uno o más grupos tales como alquilo C1-4, alcoxi C1-4, nitro, halogeno o trifluorometilo); conector representa una cadena de alquilo C2-6,. -(CH2)n-C:::C-, -(CH2)n-C:::C- o -(CH2)n-O-, donde n = 1 a 5; R3 representa un grupo de la formula general (3) para lo cual X = O o S, el conector puede estar conectado a las posiciones orto, meta o para del aromático del grupo R3, R4 y R8 representan H, fluoro, o un grupo alquenilo C5-10 lineal o ramificado, R5, R6 y R7 representan H o fluoro, R9, R10 y R11 representan H un grupo alquilo C1-5 lineal o ramificado, y además las sales de adicion con bases aceptables para uso farmacéutico, y los diversos enantiomeros de los compuestos que tienen carbonos asimétricos, y además sus mezclas en cualquier proporcion, incluyendo en particular mezclas racémicas. Reivindicacion 6: El producto se trata con un derivado halogenado de formula R2Y (para los compuestos correspondientes a la formula (1)) y R3-conector-(Y o Ots) (para los compuestos correspondientes a la formula (2)) donde R2, R3, conector e Y y las condiciones de reaccion son segun se describieron en el párrafo a) anterior. Reivindicacion 7: Proceso para preparar los compuestos químicos de acuerdo con cualquiera de las reivindicaciones 1 a 5; caracterizado porque a) un compuesto de formula general (4) en la cual R1 representa los grupos segun se describieron anteriormente en las formulas (19) y (2), se trata con un derivado halogenado R2Y (para los compuestos correspondientes a la formula (1)) y R3-conector o OTS) (para los compuestos correspondientes a la formula (2)) donde R2, R3 y conector son segun se describieron para las formulas (1) y (2) e Y representa un halogeno tal como Cl, Br o yodo. Esta reaccion puede llevarse a cabo en presencia de una base tal como hidruro de sodio o ter-butoxido de potasio en dimetilformamida. B) después de la hidrolisis de ácido en un medio alcoholico (tal como HCl en etanol), el producto se trata con un derivado halogenado de formula R2Y (para los compuestos correspondientes a la formula (2)) y R3-conector-(Y o Ots) (para los compuestos correspondientes a la formula (1)) donde R2, R3, conector e Y y las condiciones de reaccion son segun se describieron en el párrafo anterior. Reivindicacion 8: Proceso para preparar los compuestos químicos solo de formula general (1) de acuerdo con cualquiera de las reivindicaciones 1 a 5 caracterizado porque: a) un soporte solido del tipo resina, tal como, por ejemplo resina Wang o resina SASRIN, se trata con un compuesto (5) en la cual R4, R5, R6, R7, R8, R9, R10, R11, X y el conector son segun se describieron anteriormente en las formulas generales (1) y (2), y Gp representa un grupo protector, entre los cuales está el tetrahidrofurano. La reaccion de acoplamiento con la resina se lleva a cabo en condiciones conocidas para los expertos en la técnica entre las cuales está el uso de diisopropilcarbodiimida en THF en presencia de DMAP. B) después de la hidrolisis en medio ácido tal como ácido paratoluensulfonico en una mezcla de metano/diclorometano, el grupo hidroxilo liberado de esta forma se activa en la forma descripta en la formula (6). En la cual R4, R5, R6, R7, R8, R9, R10, R11, X y el conector son segun se describieron anteriormente en las formulas generales (1) y (2), Y representa un halogeno tal como Cl, Br o yodo, y Z representa un grupo sulfonilo SO2R12 donde R12 representa grupos tales como metilo o 4-metilfenilo. Para esto, la resinase trata con un haluro de sulfonilo tal como cloruro de paratoluensulfonilo en presencia de una base tal como trietilamina en diclorometano; c) la resina se trata con un compuesto de formula (7) en la cual R1 es segun se definio para las formulas (1) y (2). La reaccion se lleva a cabo en presencia de una base tal como hidruro de sodio o ter-butoxido de potasio en dimetilformamida. d) La resina así obtenida de esta forma se fracciona y se hace reaccionar con varios agentes alquilantes R2Y donde R2 es segun se definio anteriormente para las formulas (1) y (2), e Y representa un halogeno tal como Cl, Br o yodo. Las condiciones de reaccion son las mismas que las definidas en el párrafo a) del método 1. Después de la escision de la resina en un medio ácido tal como ácido trifluoroacético en diclorometano, los compuestos obtenidos con este método de síntesis corresponden solo a la formula (1).Activating compounds of PPAR alpha and / or gamma receptors and are used to manufacture pharmaceutical compositions and medications for the treatment of metabolic disorders such as diabetes, obesity, dyslipidemia and metabolic syndrome. Claim 1: 3,5-Dioxo- (2H, 4H) -1,2,4-triazine derivatives of the general formulas (1) and (2) in which R1 represents H, a C1-6 alkyl radical, alkoxy or linear or branched alkenyl, a C3 or C5-6 cycloalkyl radical, a C1-2 alkyl phenyl radical or a phenyl radical (the phenyl ring is optionally substituted with one or more groups such as C1-4 alkyl, C1-4 alkoxy , nitrile, nitro, halogen or trifluoromethyl), a thiophene-2-yl heterocycle, a secondary C1-7 alkylamine, or a C5-6 cycloalkylamine, or a halogen; R2 represents H, a linear or branched C1-7 alkyl or an alkenyl radical, or one of the following radicals: C1-5 alkyl substituted with groups such as trifluoromethyl, monofluoroethyl or polyfluoroethyl, C5-6 cycloalkyl nitrile, benzodioxan-2-yl , phthalimide, pyridinyl, 2,2,2-trifluoroacetylamino, C1-4 alkoxycarbonylvinyl, hydroxycarbonylvinyl, C1-4 alkoxycarbonyl, carboxylate, thiophene-2-carbonyl, indolyl, phenylcarbamoyl (for which the phenyl ring is optionally substituted with one or more groups such as C1-2 alkyl or nitro), C1-4 alkoxy or alkoxyalkyl (C1-4 for alkoxy, C2-4 for alkyl), phenyloxy or benzyloxy or phenyl or benzhydryl (for which the ring of phenyl is optionally substituted with one or more groups such as C1-4 alkyl, C1-4 alkoxy, nitro, halogen or trifluoromethyl); connector represents a C2-6 alkyl chain ,. - (CH2) n-C ::: C-, - (CH2) n-C ::: C- or - (CH2) n-O-, where n = 1 to 5; R3 represents a group of the general formula (3) for which X = O or S, the connector may be connected to the ortho, meta or para positions of the aromatic group R3, R4 and R8 represent H, fluoro, or a group linear or branched C5-10 alkenyl, R5, R6 and R7 represent H or fluoro, R9, R10 and R11 represent H a linear or branched C1-5 alkyl group, and also the addition salts with acceptable bases for pharmaceutical use, and the various enantiomers of the compounds having asymmetric carbons, and also their mixtures in any proportion, including in particular racemic mixtures. Claim 6: The product is treated with a halogenated derivative of formula R2Y (for the compounds corresponding to the formula (1)) and R3-connector- (Y or Ots) (for the compounds corresponding to the formula (2)) wherein R2 , R3, connector and Y and the reaction conditions are as described in paragraph a) above. Claim 7: Process for preparing the chemical compounds according to any one of claims 1 to 5; characterized in that a) a compound of general formula (4) in which R1 represents the groups as described above in formulas (19) and (2), is treated with a halogenated derivative R2Y (for compounds corresponding to the formula ( 1)) and R3-connector or OTS) (for the compounds corresponding to formula (2)) where R2, R3 and connector are as described for formulas (1) and (2) and Y represents a halogen such as Cl , Br or iodine. This reaction can be carried out in the presence of a base such as sodium hydride or potassium tert-butoxide in dimethylformamide. B) after acid hydrolysis in an alcoholic medium (such as HCl in ethanol), the product is treated with a halogenated derivative of formula R2Y (for compounds corresponding to formula (2)) and R3-connector- (Y or Ots) (for the compounds corresponding to formula (1)) where R2, R3, connector and Y and the reaction conditions are as described in the previous paragraph. Claim 8: Process for preparing chemical compounds only of general formula (1) according to any of claims 1 to 5 characterized in that: a) a solid support of the resin type, such as, for example Wang resin or SASRIN resin, is deals with a compound (5) in which R4, R5, R6, R7, R8, R9, R10, R11, X and the connector are as previously described in the general formulas (1) and (2), and Gp represents a protective group, among which is tetrahydrofuran. The coupling reaction with the resin is carried out under conditions known to those skilled in the art, among which is the use of diisopropylcarbodiimide in THF in the presence of DMAP. B) after hydrolysis in acidic medium such as paratoluenesulfonic acid in a methane / dichloromethane mixture, the hydroxyl group released in this way is activated in the manner described in the formula (6). In which R4, R5, R6, R7, R8, R9, R10, R11, X and the connector are as previously described in the general formulas (1) and (2), Y represents a halogen such as Cl, Br or iodine, and Z represents a sulfonyl group SO2R12 where R12 represents groups such as methyl or 4-methylphenyl. For this, the resinase is treated with a sulfonyl halide such as paratoluenesulfonyl chloride in the presence of a base such as triethylamine in dichloromethane; c) the resin is treated with a compound of formula (7) in which R1 is as defined for formulas (1) and (2). The reaction is carried out in the presence of a base such as sodium hydride or potassium tert-butoxide in dimethylformamide. d) The resin thus obtained in this way is fractionated and reacted with various alkylating agents R2Y where R2 is as defined above for formulas (1) and (2), and Y represents a halogen such as Cl, Br or iodine . The reaction conditions are the same as those defined in paragraph a) of method 1. After the cleavage of the resin in an acidic medium such as trifluoroacetic acid in dichloromethane, the compounds obtained with this synthesis method correspond only to the formula (one).

ARP050100598A 2004-02-18 2005-02-18 DERIVATIVES OF 3,5 - DIOXO - (2H, 4H) - 1,2,4 - TRIAZINA ACTIVATORS OF PPAR ALFA AND / OR GAMMA RECEPTORS, THEIR PREPARATION, THEIR USE IN PHARMACEUTICAL COMPOSITIONS AND THEIR USE IN THE TREATMENT OF METABOLIC DISORDERS. AR047748A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0401606A FR2866339B1 (en) 2004-02-18 2004-02-18 1,2,4-TRIAZINE DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATION IN HUMAN THERAPEUTICS

Publications (1)

Publication Number Publication Date
AR047748A1 true AR047748A1 (en) 2006-02-15

Family

ID=34803438

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP050100598A AR047748A1 (en) 2004-02-18 2005-02-18 DERIVATIVES OF 3,5 - DIOXO - (2H, 4H) - 1,2,4 - TRIAZINA ACTIVATORS OF PPAR ALFA AND / OR GAMMA RECEPTORS, THEIR PREPARATION, THEIR USE IN PHARMACEUTICAL COMPOSITIONS AND THEIR USE IN THE TREATMENT OF METABOLIC DISORDERS.

Country Status (4)

Country Link
AR (1) AR047748A1 (en)
FR (1) FR2866339B1 (en)
TW (1) TW200538445A (en)
WO (1) WO2005080354A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2882750B1 (en) * 2005-03-03 2007-05-11 Pierre Fabre Medicament Sa 1,2,4-TRIAZINE DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATION IN HUMAN THERAPEUTICS
US11241420B2 (en) 2007-04-11 2022-02-08 Omeros Corporation Compositions and methods for prophylaxis and treatment of addictions
US20160331729A9 (en) 2007-04-11 2016-11-17 Omeros Corporation Compositions and methods for prophylaxis and treatment of addictions
FR2933979B1 (en) 2008-07-15 2012-08-24 Pf Medicament TRIAZINE AND URACIL DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATION IN HUMAN THERAPY
BR112016027455A2 (en) * 2014-05-23 2017-10-17 Fundacao Univ De Brasilia/Centro De Apoio Ao Desenvolvimento Tecnologico ppar modulators

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UA82048C2 (en) * 2000-11-10 2008-03-11 Эли Лилли Энд Компани Peroxisome proliferator activated receptor alpha agonists
GB0113233D0 (en) * 2001-05-31 2001-07-25 Glaxo Group Ltd Chemical compounds

Also Published As

Publication number Publication date
FR2866339A1 (en) 2005-08-19
FR2866339B1 (en) 2006-05-05
TW200538445A (en) 2005-12-01
WO2005080354A1 (en) 2005-09-01

Similar Documents

Publication Publication Date Title
RS50672B (en) Method for preparing n-phenylpyrazole-1-carboxamides
PE20020504A1 (en) APOPTOSIS-PROMOTING N-ACILSULFONAMIDES
RS54708B1 (en) Arylethynyl derivatives
RS51007B (en) Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto
RU2006101890A (en) THIAZOLYLPIPERIDINE DERIVATIVES AS BCH INHIBITORS
FR2809396B1 (en) NOVEL MOLECULES HAVING CALCIMIMETIC ACTIVITY AND THEIR METHOD OF PREPARATION
UY28823A1 (en) ALPHA ARIL OR HETEROARIL METHYL BETA PIPERIDINE PROPANOIC ACID COMPOUNDS AS ANRL RECEIVER ANTAGONISTS
PE20050142A1 (en) BENZAMIDE 2-HYDROXY-3-DIAMINOALKANES
AR034792A1 (en) DERIVATIVES OF 1-PHENYL SULFONIL-1,3-DIHIDRO-2H-INDOL-2-ONA, ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS
AR053415A1 (en) DIPEPTIDIL PEPTIDASA IV INHIBITORS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND PROCESSES FOR THE PREPARATION OF COMPOUNDS AND COMPOSITION
WO2008115098A3 (en) Substituted 2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indoles, methods for the production and the use thereof
BR0307409A (en) 2-Furanecarboxylic acid hydrazide compounds, pharmaceutical compositions containing them and use thereof for the preparation of a preventive or therapeutic agent
AR042632A1 (en) COMPOUNDS DERIVED FROM ACID (2S) -3- (4- {2- [AMINO] -2-OXOETOXI} PHENYL) -2-ETOXIPROPANOIC AS THERAPEUTIC AGENTS FOR DISORDERS IN THE METABOLISM OF LIPIDS AND PHARMACEUTICAL COMPOSITIONS
AR064730A1 (en) DERIVATIVES OF 2,4-DIANILINOPIRIMIDINAS, ITS PREPARATION, PHARMACEUTICAL COMPOSITIONS AND USES AS INHIBITORS OF IKK
AR047748A1 (en) DERIVATIVES OF 3,5 - DIOXO - (2H, 4H) - 1,2,4 - TRIAZINA ACTIVATORS OF PPAR ALFA AND / OR GAMMA RECEPTORS, THEIR PREPARATION, THEIR USE IN PHARMACEUTICAL COMPOSITIONS AND THEIR USE IN THE TREATMENT OF METABOLIC DISORDERS.
RU2502730C2 (en) Sulphonamide compounds and use thereof
AR052866A1 (en) SUBSTITUTED MONOCICLIC PHENYL-METANONES
ES2187983T3 (en) DERIVATIVES 1,2,3,4-TETRAHIDRONAFTALENO SUBSTITUTED.
AR053554A1 (en) PIRIMIDINE DERIVATIVES FOR THE TREATMENT OF HYPERPROLIFERATIVE DISORDERS
ATE473973T1 (en) SUBSTITUTED BENZIMIDAZOLES AND THEIR USE FOR INDUCING APOPTOSIS
AR033879A1 (en) SULFONAMIDE COMPOUND, PHARMACEUTICAL COMPOSITION THAT UNDERSTANDS IT, ITS USE TO PREPARE SUCH COMPOSITION AND PROCEDURE FOR OBTAINING SUCH COMPOUND
RU2014145819A (en) BICYCLE CONNECTION
NO20080739L (en) Methods for Treating Epileptogenesis
AR042362A1 (en) DERIVATIVES OF 3H-QUINAZOLIN-4-ONA, PROCESS OF OBTAINING AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
PE20120217A1 (en) DERIVATIVES OF ALKYL-HETEROCYCLES CARBAMATES, THEIR PREPARATION AND THEIR APPLICATION IN THERAPEUTICS

Legal Events

Date Code Title Description
FB Suspension of granting procedure