AR049547A1 - STEROID PROPHARMS WITH ANDROGENIC ACTION - Google Patents
STEROID PROPHARMS WITH ANDROGENIC ACTIONInfo
- Publication number
- AR049547A1 AR049547A1 ARP050102084A ARP050102084A AR049547A1 AR 049547 A1 AR049547 A1 AR 049547A1 AR P050102084 A ARP050102084 A AR P050102084A AR P050102084 A ARP050102084 A AR P050102084A AR 049547 A1 AR049547 A1 AR 049547A1
- Authority
- AR
- Argentina
- Prior art keywords
- group
- hydrogen atom
- alkyl
- cycloalkyl
- atom
- Prior art date
Links
- 150000003431 steroids Chemical class 0.000 title abstract 4
- 230000001548 androgenic effect Effects 0.000 title abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 11
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 5
- 125000005843 halogen group Chemical group 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 3
- 101100240526 Caenorhabditis elegans nhr-20 gene Proteins 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 3
- 125000005275 alkylenearyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000002560 nitrile group Chemical group 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229940002612 prodrug Drugs 0.000 abstract 2
- 239000000651 prodrug Substances 0.000 abstract 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- -1 cyclic steroid Chemical class 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0038—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an androstane skeleton, including 18- or 19-substituted derivatives, 18-nor derivatives and also derivatives where position 17-beta is substituted by a carbon atom not directly bonded to a further carbon atom and not being part of an amide group
-
- 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
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/26—Androgens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0044—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an estrane or gonane skeleton, including 18-substituted derivatives and derivatives where position 17-beta is substituted by a carbon atom not directly bonded to another carbon atom and not being part of an amide group
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Profármacos de esteroides, composiciones farmacéuticas, que contienen estos compuestos, así como su uso para la preparacion de medicamentos con accion androgénica. Reivindicacion 1: Profármacos de esteroides de la formula general (1), caracterizado porque: n es un numero 0-4; R1 es un radical -SO2NH2 o -NHSO2NH2; en donde R2, R3, y X, X1 son un átomo de hidrogeno, un átomo de halogeno, un grupo nitrilo, un grupo nitro, un grupo alquilo C1-5, un grupo CpF2p+1 con p = 1-3, un grupo OC(O)-R20, COOR20, OR20, C(O)NHR20 u OC(O)NHR21, en donde R20, R21 y R22 son un grupo alquilo C1-5, un grupo cicloalquilo C3-8, un grupo arilo, un grupo alquilenarilo C1-4, un grupo alquilen C1-4-cicloalquilo C3-8 o cicloalquilen C3-8-alquilo C1-4, así como R20 puede ser, además, un hidrogeno; o R2 es un radical -SO2NH2 o -NHSO2NH2; en donde R2, R3, y X, X1 son un átomo de hidrogeno, un átomo de halogeno, un grupo nitrilo, un grupo nitro, un grupo alquilo C1-5, un grupo CpF2p+1 con p = 1-3, un grupo OC(O)-R20, COOR20, OR20, C(O)NHR20 u OC(O)NHR21, en donde R20, R21 y R22 son un grupo alquilo C1-5, un grupo cicloalquilo C3-8, un grupo arilo, un grupo alquilenarilo C1-4, un grupo alquilen C1-4-cicloalquilo C3-8 o cicloalquilen C3-8-alquilo C1-4, así como R20 puede ser, además, un hidrogeno; o R3 es un radical -SO2NH2 o -NHSO2NH2; en donde R2, R3, y X, X1 son un átomo de hidrogeno, un átomo de halogeno, un grupo nitrilo, un grupo nitro, un grupo alquilo C1-5, un grupo CpF2p+1 con p = 1-3, un grupo OC(O)-R20, COOR20, OR20, C(O)NHR20 u OC(O)NHR21, en donde R20, R21 y R22 son un grupo alquilo C1-5, un grupo cicloalquilo C3-8, un grupo arilo, un grupo alquilenarilo C1-4, un grupo alquilen C1-4-cicloalquilo C3-8 o cicloalquilen C3-8-alquilo C1-4, así como R20 también puede ser un hidrogeno; y ESTEROIDE es un sistema cíclico esteroide de acuerdo con las formulas generales (2) a (4), en donde: Y es un átomo de oxígeno o de carbono; R4 es un átomo de hidrogeno, un átomo de halogeno, un grupo metilo, trifluorometilo, hidroxi, tri(alquil C1-6)sililoxi, alcoxi C1-5 o heterocicloalquiloxi C2-5; R7 es un átomo de hidrogeno, un grupo metilo o etilo; R10 es un átomo de hidrogeno, un grupo metilo o etilo; R11 es un átomo de halogeno, un átomo de hidrogeno, un grupo hidroxi, un grupo metoxi, un grupo OC(O)-R20, un grupo metilo o etilo; R12 es un átomo de hidrogeno, un grupo metilo o un grupo etilo; R13 es un átomo de hidrogeno, un grupo metilo, etilo, etinilo, trifluorometilo, pentafluoroetilo; R14 es un átomo de hidrogeno, un grupo OH o un átomo de oxígeno unido a través de un enlace doble; R15 es un grupo hidroxi, tri(alquil C1-6)sililoxi, alcoxi C1-5, un grupo OC(O)-R20 o un grupo heterocicloalquiloxi C2-5; en donde se puede hallar un enlace doble adicional en la posicion 4,5 y cuando Y es un átomo de carbono, se pueden hallar enlaces dobles adicionales en la posicion 1,2 o cuando el radical R14 es un átomo de hidrogeno o un grupo OH, en la posicion 2,3; y sus sales farmacéuticamente aceptables.Steroid prodrugs, pharmaceutical compositions, containing these compounds, as well as their use for the preparation of drugs with androgenic action. Claim 1: Steroid prodrugs of the general formula (1), characterized in that: n is a number 0-4; R1 is a radical -SO2NH2 or -NHSO2NH2; wherein R2, R3, and X, X1 are a hydrogen atom, a halogen atom, a nitrile group, a nitro group, a C1-5 alkyl group, a CpF2p + 1 group with p = 1-3, a group OC (O) -R20, COOR20, OR20, C (O) NHR20 or OC (O) NHR21, where R20, R21 and R22 are a C1-5 alkyl group, a C3-8 cycloalkyl group, an aryl group, a C 1-4 alkylenearyl group, a C 1-8 alkylene-C 3-8 cycloalkyl or C 3-8 cycloalkylene-C 1-4 alkyl group, as well as R 20 may also be a hydrogen; or R2 is a radical -SO2NH2 or -NHSO2NH2; wherein R2, R3, and X, X1 are a hydrogen atom, a halogen atom, a nitrile group, a nitro group, a C1-5 alkyl group, a CpF2p + 1 group with p = 1-3, a group OC (O) -R20, COOR20, OR20, C (O) NHR20 or OC (O) NHR21, where R20, R21 and R22 are a C1-5 alkyl group, a C3-8 cycloalkyl group, an aryl group, a C 1-4 alkylenearyl group, a C 1-8 alkylene-C 3-8 cycloalkyl or C 3-8 cycloalkylene-C 1-4 alkyl group, as well as R 20 may also be a hydrogen; or R3 is a radical -SO2NH2 or -NHSO2NH2; wherein R2, R3, and X, X1 are a hydrogen atom, a halogen atom, a nitrile group, a nitro group, a C1-5 alkyl group, a CpF2p + 1 group with p = 1-3, a group OC (O) -R20, COOR20, OR20, C (O) NHR20 or OC (O) NHR21, where R20, R21 and R22 are a C1-5 alkyl group, a C3-8 cycloalkyl group, an aryl group, a C1-4 alkylenearyl group, a C1-4 alkylene-C3-8 cycloalkyl or C3-8 cycloalkyl-C1-4 alkyl group, as well as R20 may also be a hydrogen; and STEROID is a cyclic steroid system according to general formulas (2) to (4), where: Y is an oxygen or carbon atom; R4 is a hydrogen atom, a halogen atom, a methyl, trifluoromethyl, hydroxy, tri (C1-6 alkyl) silyloxy, C1-5 alkoxy or C2-5 heterocycloalkyloxy group; R7 is a hydrogen atom, a methyl or ethyl group; R10 is a hydrogen atom, a methyl or ethyl group; R11 is a halogen atom, a hydrogen atom, a hydroxy group, a methoxy group, an OC (O) -R20 group, a methyl or ethyl group; R12 is a hydrogen atom, a methyl group or an ethyl group; R13 is a hydrogen atom, a methyl, ethyl, ethynyl, trifluoromethyl, pentafluoroethyl group; R14 is a hydrogen atom, an OH group or an oxygen atom attached through a double bond; R15 is a hydroxy, tri (C1-6 alkyl) silyloxy, C1-5 alkoxy, an OC (O) -R20 group or a C2-5 heterocycloalkyloxy group; where an additional double bond can be found at position 4.5 and when Y is a carbon atom, additional double bonds can be found at position 1.2 or when the radical R14 is a hydrogen atom or an OH group , in position 2,3; and its pharmaceutically acceptable salts.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004025986A DE102004025986A1 (en) | 2004-05-21 | 2004-05-21 | Steroid prodrugs with androgenic effects |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR049547A1 true AR049547A1 (en) | 2006-08-16 |
Family
ID=34968657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP050102084A AR049547A1 (en) | 2004-05-21 | 2005-05-20 | STEROID PROPHARMS WITH ANDROGENIC ACTION |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP1747229A1 (en) |
| JP (1) | JP2007538026A (en) |
| CN (1) | CN1993375A (en) |
| AR (1) | AR049547A1 (en) |
| AU (1) | AU2005245568A1 (en) |
| BR (1) | BRPI0510136A (en) |
| CA (1) | CA2564963A1 (en) |
| CR (1) | CR8785A (en) |
| DE (1) | DE102004025986A1 (en) |
| EA (1) | EA200602049A1 (en) |
| EC (1) | ECSP067028A (en) |
| GT (1) | GT200500122A (en) |
| IL (1) | IL179293A0 (en) |
| MX (1) | MXPA06013469A (en) |
| NO (1) | NO20065885L (en) |
| PA (1) | PA8633601A1 (en) |
| PE (1) | PE20060271A1 (en) |
| SV (1) | SV2006002123A (en) |
| TW (1) | TW200613317A (en) |
| UY (1) | UY28911A1 (en) |
| WO (1) | WO2005113575A1 (en) |
| ZA (1) | ZA200610769B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10027887A1 (en) | 2000-05-31 | 2001-12-13 | Jenapharm Gmbh | Compounds with a sulfonamide group and pharmaceutical compositions containing these compounds |
| US7534780B2 (en) | 2004-05-21 | 2009-05-19 | Bayer Schering Pharma Aktiengesellschaft | Estradiol prodrugs |
| DE102005057224A1 (en) * | 2005-11-29 | 2007-05-31 | Bayer Schering Pharma Ag | New 9-alpha substituted estratriene derivatives esterified with a sulfamoylphenyl-substituted acid residue, are prodrugs useful as carboanhydrase inhibitors for treating estrogen deficiency disorders |
| DE102005057408A1 (en) * | 2005-11-30 | 2007-05-31 | Bayer Schering Pharma Ag | New sulfamoylsulfonate prodrugs e.g. useful for protecting red blood cells from attack by parasites or for hormone replacement therapy, female fertility control or treating hormone-associated diseases |
| CN101708338B (en) * | 2008-12-26 | 2014-06-04 | 中国人民解放军军事医学科学院放射与辐射医学研究所 | Prodrug containing sterides structures and high dispersion preparation thereof |
| CN102964417A (en) * | 2012-11-30 | 2013-03-13 | 华中药业股份有限公司 | Synthetic method of 17-hydroxy tetrahydropyran ether steroid |
| CN107556258B (en) * | 2017-08-22 | 2021-06-04 | 湖北江田精密化学有限公司 | Preparation method of 4-amino-2-chloro-5 (1H-tetrazolyl-5) benzenesulfonamide |
| EP3533619A1 (en) * | 2018-03-02 | 2019-09-04 | Basf Se | Heat sensitive recording material and color developer |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH545316A (en) * | 1970-07-17 | 1973-12-15 | Hoffmann La Roche | Process for the preparation of acyl derivatives |
| US5001234A (en) * | 1987-04-16 | 1991-03-19 | The Upjohn Company | Cyclic hydrocarbons with an aminoalkyl sidechain |
| US5571933A (en) * | 1994-11-17 | 1996-11-05 | Duquesne University Of The Holy Ghost | Derivatives of estra 1,3,5(10)triene-17-one, 3-amino compounds and their use |
| DE19712488A1 (en) * | 1997-03-25 | 1998-10-01 | Knoell Hans Forschung Ev | Steroid sulfamates, processes for their preparation and use thereof |
| DE10027887A1 (en) * | 2000-05-31 | 2001-12-13 | Jenapharm Gmbh | Compounds with a sulfonamide group and pharmaceutical compositions containing these compounds |
-
2004
- 2004-05-21 DE DE102004025986A patent/DE102004025986A1/en not_active Ceased
-
2005
- 2005-05-10 CA CA002564963A patent/CA2564963A1/en not_active Abandoned
- 2005-05-10 CN CNA200580016339XA patent/CN1993375A/en active Pending
- 2005-05-10 EA EA200602049A patent/EA200602049A1/en unknown
- 2005-05-10 BR BRPI0510136-0A patent/BRPI0510136A/en not_active Application Discontinuation
- 2005-05-10 JP JP2007517047A patent/JP2007538026A/en active Pending
- 2005-05-10 AU AU2005245568A patent/AU2005245568A1/en not_active Abandoned
- 2005-05-10 MX MXPA06013469A patent/MXPA06013469A/en not_active Application Discontinuation
- 2005-05-10 WO PCT/EP2005/005256 patent/WO2005113575A1/en not_active Ceased
- 2005-05-10 EP EP05742657A patent/EP1747229A1/en not_active Withdrawn
- 2005-05-20 PE PE2005000556A patent/PE20060271A1/en not_active Application Discontinuation
- 2005-05-20 PA PA20058633601A patent/PA8633601A1/en unknown
- 2005-05-20 TW TW094116504A patent/TW200613317A/en unknown
- 2005-05-20 UY UY28911A patent/UY28911A1/en not_active Application Discontinuation
- 2005-05-20 AR ARP050102084A patent/AR049547A1/en not_active Application Discontinuation
- 2005-05-20 GT GT200500122A patent/GT200500122A/en unknown
- 2005-05-23 SV SV2005002123A patent/SV2006002123A/en not_active Application Discontinuation
-
2006
- 2006-11-15 IL IL179293A patent/IL179293A0/en unknown
- 2006-11-27 EC EC2006007028A patent/ECSP067028A/en unknown
- 2006-12-05 CR CR8785A patent/CR8785A/en not_active Application Discontinuation
- 2006-12-19 NO NO20065885A patent/NO20065885L/en unknown
- 2006-12-20 ZA ZA200610769A patent/ZA200610769B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA06013469A (en) | 2007-01-23 |
| WO2005113575A1 (en) | 2005-12-01 |
| TW200613317A (en) | 2006-05-01 |
| UY28911A1 (en) | 2005-12-30 |
| CA2564963A1 (en) | 2005-12-01 |
| ZA200610769B (en) | 2008-08-27 |
| PA8633601A1 (en) | 2006-07-03 |
| EA200602049A1 (en) | 2007-06-29 |
| JP2007538026A (en) | 2007-12-27 |
| NO20065885L (en) | 2006-12-19 |
| PE20060271A1 (en) | 2006-05-25 |
| DE102004025986A1 (en) | 2005-12-15 |
| EP1747229A1 (en) | 2007-01-31 |
| BRPI0510136A (en) | 2007-10-02 |
| CR8785A (en) | 2007-02-05 |
| IL179293A0 (en) | 2007-03-08 |
| CN1993375A (en) | 2007-07-04 |
| GT200500122A (en) | 2006-01-24 |
| AU2005245568A1 (en) | 2005-12-01 |
| ECSP067028A (en) | 2006-12-29 |
| SV2006002123A (en) | 2006-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |