PE20001494A1 - DERIVATIVES OF CICLOBUTEN-3,4-DIONA ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS - Google Patents

DERIVATIVES OF CICLOBUTEN-3,4-DIONA ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS

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Publication number
PE20001494A1
PE20001494A1 PE2000000185A PE0001852000A PE20001494A1 PE 20001494 A1 PE20001494 A1 PE 20001494A1 PE 2000000185 A PE2000000185 A PE 2000000185A PE 0001852000 A PE0001852000 A PE 0001852000A PE 20001494 A1 PE20001494 A1 PE 20001494A1
Authority
PE
Peru
Prior art keywords
cyclohexan
trans
alkyl
methyl
diona
Prior art date
Application number
PE2000000185A
Other languages
Spanish (es)
Inventor
Philippe R Bovy
Gerad Defosse
Claudie Gautier
Gilbert Marciniak
Christophe Philippo
Dorsselaer Viviane Van
Original Assignee
Sanofi Synthelabo
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 Sanofi Synthelabo filed Critical Sanofi Synthelabo
Publication of PE20001494A1 publication Critical patent/PE20001494A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Abstract

SE REFIERE A DERIVADOS DE CICLOBUTEN-3,4-DIONA DE FORMULA I, DONDE: R1 Y R2 SON H, ALQUILO C1-C6, ALQUENILO C2-C6, -(CH2)n-CICLOALQUILO C3-C6; R3 ES H, ALQUILO C1-C6, -(CH2)n- CICLOALQUILO C3-C6, -CH2-CO2-ALQUILO C1-C3, CH2COOH; W ES NR4R5; R4 Y R5 SON H, ALQUILO C1-C6, ALQUENILO C2-C6, ALQUINILO C2-C6, (CH2)n-CICLOALQUILO C3-C6, FLUOROALQUILO, ENTRE OTROS; O R4 Y R5 JUNTOS FORMAN UN GRUPO a; n ES 0-2, m ES 1-2, p y p` SON 1-3. SON COMPUESTOS PREFERIDOS TRANS-4-[[[2-DIPROPILAMINO)-3,4-DIOXOCICLOBUT-1-EN-1-IL]AMINO]-METIL]CICLOHEXAN-1-CARBOXAMIDA, TRANS-4-[[[2-DIPROPILAMINO)-3,4-DIOXOCICLOBUT-1-EN-1-IL]AMINO]-METIL]CICLOHEXAN-1-N-CICLOPROPILCARBOXAMIDA; TRANS-4-[[[2-BUTILETILAMINO)-3,4-DIOXOCICLOBUT-1-EN-1-IL]METILAMINO]-METIL]CICLOHEXAN-1-CARBOXAMIDA, TRANS-4-[[[2-DIPROPILAMINO)-3,4-DIOXOCICLOBUT-1-EN-1-IL]METILAMINO]METIL]CICLOHEXAN-1-CARBOXAMIDA. SE REFIERA TAMBIEN A UN PROCEDIMIENTO PARA LA PREPARACION. LOS DERIVADOS DE CICLOBUTEN-3,4-DIONA SON INHIBIDORES DE LA FOSFODIESTERASA 5 POR LO QUE PUEDEN SER UTILES EN EL TRATAMIENTO DE HIPERTROFIA BENIGNA PROSTATICA, INCONTINENCIA, DISFUNCIONES SEXUALES, VESICULA OBSTRUIDA, DISMENORREA, PARTO PREMATURO, DISFUNCIONES SEXUALES, ANGINA, HIPERTENSION PULMONAR, ATAQUE DE APOPLEJIA, ARTERIOSCLEROSISREFERS TO CYCLOBUTEN-3,4-DIONA DERIVATIVES OF FORMULA I, WHERE: R1 AND R2 ARE H, C1-C6 ALKYL, C2-C6 ALKENYL, - (CH2) n-CYCLOALKYL C3-C6; R3 IS H, C1-C6 ALKYL, - (CH2) n- C3-C6 CYCLOALKYL, -CH2-CO2-C1-C3 ALKYL, CH2COOH; W IS NR4R5; R4 AND R5 ARE H, C1-C6 ALKYL, C2-C6 ALKENYL, C2-C6 ALKINYL, (CH2) n-C3-C6 CYCLOALKYL, FLUOROALKYL, AMONG OTHERS; OR R4 AND R5 TOGETHER FORM A GROUP a; n IS 0-2, m IS 1-2, p and p` ARE 1-3. THE PREFERRED COMPOUNDS ARE TRANS-4 - [[[2-DIPROPYLAMINE) -3,4-DIOXOCICLOBUT-1-EN-1-IL] AMINO] -MEthyl] CYCLOHEXAN-1-CARBOXAMIDE, TRANS-4 - [[[2-DIPROPYLAMINE ) -3,4-DIOXOCYCLOBUT-1-EN-1-IL] AMINO] -MEthyl] CYCLOHEXAN-1-N-CYCLOPROPYLCARBOXAMIDE; TRANS-4 - [[[2-BUTYLETHYLAMINE) -3,4-DIOXOCICLOBUT-1-EN-1-IL] METHYLAMINO] -MEthyl] CYCLOHEXAN-1-CARBOXAMIDE, TRANS-4 - [[[2-DIPROPYLAMINE) -3 , 4-DIOXOCYCLOBUT-1-EN-1-IL] METHYLAMINO] METHYL] CYCLOHEXAN-1-CARBOXAMIDE. IT ALSO REFERS TO A PROCEDURE FOR THE PREPARATION. THE DERIVATIVES OF CYCLOBUTEN-3,4-DIONA ARE INHIBITORS OF PHOSPHODIESTERASE 5 SO THEY MAY BE USEFUL IN THE TREATMENT OF BENIGN PROSTATIC HYPERTROPHIA, INCONTINENCE, SEXUAL DYSFUNCTIONS, OBSTRUED VESICULA, ANGUISHED DYSMENORHEA, PREMENORAL DYSMENORHEA , APOPLEJIA ATTACK, ARTERIOSCLEROSIS

PE2000000185A 1999-03-04 2000-03-03 DERIVATIVES OF CICLOBUTEN-3,4-DIONA ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS PE20001494A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR9902679A FR2790472B1 (en) 1999-03-04 1999-03-04 DERIVATIVES OF CYCLOBUTENE-3, 4-DIONE, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION

Publications (1)

Publication Number Publication Date
PE20001494A1 true PE20001494A1 (en) 2001-03-04

Family

ID=9542807

Family Applications (1)

Application Number Title Priority Date Filing Date
PE2000000185A PE20001494A1 (en) 1999-03-04 2000-03-03 DERIVATIVES OF CICLOBUTEN-3,4-DIONA ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS

Country Status (6)

Country Link
AR (1) AR022809A1 (en)
AU (1) AU2922700A (en)
CO (1) CO5160254A1 (en)
FR (1) FR2790472B1 (en)
PE (1) PE20001494A1 (en)
WO (1) WO2000051973A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6548508B2 (en) 2000-10-20 2003-04-15 Pfizer, Inc. Use of PDE V inhibitors for improved fecundity in mammals
US6495576B2 (en) 2001-02-07 2002-12-17 Abbott Laboratories Aminal diones as potassium channel openers
AR068509A1 (en) * 2007-09-19 2009-11-18 Jerini Ag BRADIQUININE B1 RECEIVER ANTAGOSNIST

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9312210D0 (en) * 1993-06-14 1993-07-28 Smithkline Beecham Plc Chemical compounds

Also Published As

Publication number Publication date
CO5160254A1 (en) 2002-05-30
FR2790472B1 (en) 2001-04-06
WO2000051973A1 (en) 2000-09-08
AU2922700A (en) 2000-09-21
AR022809A1 (en) 2002-09-04
FR2790472A1 (en) 2000-09-08

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