NO309527B1 - Fenylsubstituerte 4-azasteroid-fluorderivater, farmasöytisk preparat inneholdende slike derivater, anvendelse derav, og fremgangsmåte for deres fremstilling - Google Patents
Fenylsubstituerte 4-azasteroid-fluorderivater, farmasöytisk preparat inneholdende slike derivater, anvendelse derav, og fremgangsmåte for deres fremstilling Download PDFInfo
- Publication number
- NO309527B1 NO309527B1 NO972186A NO972186A NO309527B1 NO 309527 B1 NO309527 B1 NO 309527B1 NO 972186 A NO972186 A NO 972186A NO 972186 A NO972186 A NO 972186A NO 309527 B1 NO309527 B1 NO 309527B1
- Authority
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- Norway
- Prior art keywords
- compound
- formula
- aza
- oxo
- carboxamide
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 18
- 239000000825 pharmaceutical preparation Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 230000008569 process Effects 0.000 title claims description 4
- -1 4-azasteroid fluorine derivatives Chemical class 0.000 title description 44
- 150000001875 compounds Chemical class 0.000 claims description 137
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
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- 206010060862 Prostate cancer Diseases 0.000 claims description 7
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 7
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 6
- 201000004384 Alopecia Diseases 0.000 claims description 6
- 206010006187 Breast cancer Diseases 0.000 claims description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims description 6
- 206010020112 Hirsutism Diseases 0.000 claims description 6
- 206010039792 Seborrhoea Diseases 0.000 claims description 6
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- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 5
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 230000002113 chemopreventative effect Effects 0.000 claims description 5
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- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 5
- 206010036049 Polycystic ovaries Diseases 0.000 claims description 4
- 229940123934 Reductase inhibitor Drugs 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
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- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
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- 238000006243 chemical reaction Methods 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 21
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
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- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- 150000000520 4-azasteroids Chemical class 0.000 description 4
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- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
- C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
- C07J73/005—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by nitrogen as hetero atom
-
- 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
- A61P5/28—Antiandrogens
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9518858.7A GB9518858D0 (en) | 1995-09-14 | 1995-09-14 | Phenylsubstituted 4-azasteroid fluoroderivatives |
| PCT/EP1996/003518 WO1997010257A1 (en) | 1995-09-14 | 1996-08-09 | Phenylsubstituted 4-azasteroid fluoroderivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO972186D0 NO972186D0 (no) | 1997-05-13 |
| NO972186L NO972186L (no) | 1997-07-02 |
| NO309527B1 true NO309527B1 (no) | 2001-02-12 |
Family
ID=10780746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO972186A NO309527B1 (no) | 1995-09-14 | 1997-05-13 | Fenylsubstituerte 4-azasteroid-fluorderivater, farmasöytisk preparat inneholdende slike derivater, anvendelse derav, og fremgangsmåte for deres fremstilling |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US5922728A (cs) |
| EP (1) | EP0793671B1 (cs) |
| JP (1) | JPH10509188A (cs) |
| KR (1) | KR100448745B1 (cs) |
| CN (1) | CN1104439C (cs) |
| AR (1) | AR004511A1 (cs) |
| AT (1) | ATE189681T1 (cs) |
| AU (1) | AU715858B2 (cs) |
| BR (1) | BR9606638A (cs) |
| CA (1) | CA2204002A1 (cs) |
| CZ (1) | CZ291450B6 (cs) |
| DE (1) | DE69606623T2 (cs) |
| DK (1) | DK0793671T3 (cs) |
| EA (1) | EA000362B1 (cs) |
| ES (1) | ES2144765T3 (cs) |
| GB (1) | GB9518858D0 (cs) |
| GR (1) | GR3033315T3 (cs) |
| HU (1) | HUP9702038A3 (cs) |
| IL (1) | IL120742A (cs) |
| MY (1) | MY116271A (cs) |
| NO (1) | NO309527B1 (cs) |
| NZ (1) | NZ316060A (cs) |
| PL (1) | PL185196B1 (cs) |
| PT (1) | PT793671E (cs) |
| TW (1) | TW357149B (cs) |
| UA (1) | UA66748C2 (cs) |
| WO (1) | WO1997010257A1 (cs) |
| ZA (1) | ZA967631B (cs) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6054446A (en) * | 1997-12-24 | 2000-04-25 | Sri International | Anti-estrogenic steroids, and associated pharmaceutical compositions and methods of use |
| US6548491B2 (en) * | 1997-12-24 | 2003-04-15 | Sri International | Anti-estrogenic steroids, and associated pharmaceutical compositions and methods of use |
| AU2001241779A1 (en) | 2000-02-25 | 2001-09-03 | Hollis-Eden Pharmaceuticals, Inc. | Method of treatment of prostate cancer |
| US7402577B2 (en) * | 2001-10-03 | 2008-07-22 | Merck & Co., Inc. | Androstane 17-beta-carboxamides as androgen receptor modulators |
| EP1641535A4 (en) * | 2003-06-30 | 2008-05-14 | Merck & Co Inc | 17-ACETAMIDO-4-AZASTEROID DERIVATIVES AS ANDROGEN RECEPTOR MODULATORS |
| AU2004255749B2 (en) | 2003-06-30 | 2008-12-18 | Merck Sharp & Dohme Corp. | 17-acetamido-4-azasteroid derivatives as androgen receptor modulators |
| JP2007522087A (ja) * | 2003-06-30 | 2007-08-09 | メルク エンド カムパニー インコーポレーテッド | アンドロゲン受容体モジュレータとしての１７−アセトアミド−４−アザステロイド誘導体 |
| AU2004255200A1 (en) * | 2003-06-30 | 2005-01-20 | Merck & Co., Inc. | 17-acetamido-4-azasteroid derivatives as androgen receptor modulators |
| CN103787894B (zh) * | 2014-02-08 | 2015-09-16 | 济南大学 | 从甲苯二异氰酸酯制备过程中形成的残渣废料中回收甲苯二胺的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9002922D0 (en) * | 1990-02-09 | 1990-04-04 | Erba Carlo Spa | 17 beta-substituted-4-aza-5 alpha-androstan-3-one derivatives and process for their preparation |
| GB9216284D0 (en) * | 1992-07-31 | 1992-09-16 | Erba Carlo Spa | Fluorinated 17beta-substituted 4-aza-5alpha-androstane-3-one derivatives |
| GB9216329D0 (en) * | 1992-07-31 | 1992-09-16 | Erba Carlo Spa | 17beta-substituted 4-aza-5alpha-androstan-3-one derivatives |
| GB9608045D0 (en) * | 1996-04-18 | 1996-06-19 | Pharmacia Spa | Process for preparing steroids having a carboxamide side-chain |
| US5686501A (en) * | 1996-04-19 | 1997-11-11 | Foamex L.P. | Breathable open cell urethane polymers |
-
1995
- 1995-09-14 GB GBGB9518858.7A patent/GB9518858D0/en active Pending
-
1996
- 1996-08-09 BR BR9606638A patent/BR9606638A/pt not_active Application Discontinuation
- 1996-08-09 UA UA97062805A patent/UA66748C2/xx unknown
- 1996-08-09 CA CA002204002A patent/CA2204002A1/en not_active Abandoned
- 1996-08-09 NZ NZ316060A patent/NZ316060A/xx unknown
- 1996-08-09 PT PT96928436T patent/PT793671E/pt unknown
- 1996-08-09 DK DK96928436T patent/DK0793671T3/da active
- 1996-08-09 CZ CZ19971460A patent/CZ291450B6/cs not_active IP Right Cessation
- 1996-08-09 JP JP9511593A patent/JPH10509188A/ja not_active Withdrawn
- 1996-08-09 AU AU68205/96A patent/AU715858B2/en not_active Ceased
- 1996-08-09 PL PL96320114A patent/PL185196B1/pl not_active IP Right Cessation
- 1996-08-09 US US08/836,052 patent/US5922728A/en not_active Expired - Fee Related
- 1996-08-09 ES ES96928436T patent/ES2144765T3/es not_active Expired - Lifetime
- 1996-08-09 HU HU9702038A patent/HUP9702038A3/hu unknown
- 1996-08-09 CN CN96191076A patent/CN1104439C/zh not_active Expired - Fee Related
- 1996-08-09 EP EP96928436A patent/EP0793671B1/en not_active Expired - Lifetime
- 1996-08-09 IL IL12074296A patent/IL120742A/en not_active IP Right Cessation
- 1996-08-09 EA EA199700063A patent/EA000362B1/ru not_active IP Right Cessation
- 1996-08-09 WO PCT/EP1996/003518 patent/WO1997010257A1/en active IP Right Grant
- 1996-08-09 AT AT96928436T patent/ATE189681T1/de not_active IP Right Cessation
- 1996-08-09 KR KR1019970703203A patent/KR100448745B1/ko not_active IP Right Cessation
- 1996-08-09 DE DE69606623T patent/DE69606623T2/de not_active Expired - Fee Related
- 1996-09-05 TW TW085110841A patent/TW357149B/zh active
- 1996-09-09 AR ARP960104280A patent/AR004511A1/es unknown
- 1996-09-10 ZA ZA967631A patent/ZA967631B/xx unknown
- 1996-09-13 MY MYPI96003782A patent/MY116271A/en unknown
-
1997
- 1997-05-13 NO NO972186A patent/NO309527B1/no unknown
-
1999
- 1999-04-28 US US09/300,454 patent/US6114345A/en not_active Expired - Fee Related
-
2000
- 2000-04-26 GR GR20000400999T patent/GR3033315T3/el not_active IP Right Cessation
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