IE61594B1 - Steroid 5-alpha-reductase inhibitors - Google Patents
Steroid 5-alpha-reductase inhibitorsInfo
- Publication number
- IE61594B1 IE61594B1 IE18988A IE18988A IE61594B1 IE 61594 B1 IE61594 B1 IE 61594B1 IE 18988 A IE18988 A IE 18988A IE 18988 A IE18988 A IE 18988A IE 61594 B1 IE61594 B1 IE 61594B1
- Authority
- IE
- Ireland
- Prior art keywords
- alpha
- hydrogen
- alkyl
- alk
- compound
- Prior art date
Links
- 239000002677 5-alpha reductase inhibitor Substances 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 22
- -1 substituted-androsten-3-ones Chemical class 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 95
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 150000003431 steroids Chemical class 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- BQTTYKVRRLHMQQ-ZBKBXNIDSA-N (8r,9s,10s,13r,14s,17r)-17-ethenyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C=C)[C@@H]4[C@@H]3CCC21 BQTTYKVRRLHMQQ-ZBKBXNIDSA-N 0.000 claims description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 5
- 229930194542 Keto Natural products 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000003513 alkali Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 3
- 229940123934 Reductase inhibitor Drugs 0.000 claims 1
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- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- UVBXZOISXNZBLY-UHFFFAOYSA-L palladium(2+);triphenylphosphane;diacetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UVBXZOISXNZBLY-UHFFFAOYSA-L 0.000 description 1
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- WJCXADMLESSGRI-UHFFFAOYSA-N phenyl selenohypochlorite Chemical compound Cl[Se]C1=CC=CC=C1 WJCXADMLESSGRI-UHFFFAOYSA-N 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
- C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/007,539 US4888336A (en) | 1987-01-28 | 1987-01-28 | Steroid 5-alpha-reductase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE880189L IE880189L (en) | 1988-07-28 |
| IE61594B1 true IE61594B1 (en) | 1994-11-16 |
Family
ID=21726780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE18988A IE61594B1 (en) | 1987-01-28 | 1988-01-26 | Steroid 5-alpha-reductase inhibitors |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4888336A (esLanguage) |
| EP (1) | EP0277002B1 (esLanguage) |
| JP (1) | JPS63192800A (esLanguage) |
| AT (1) | ATE77388T1 (esLanguage) |
| AU (1) | AU608560B2 (esLanguage) |
| CA (1) | CA1325006C (esLanguage) |
| DE (1) | DE3871965T2 (esLanguage) |
| DK (4) | DK37388A (esLanguage) |
| ES (1) | ES2042725T3 (esLanguage) |
| GR (1) | GR3005284T3 (esLanguage) |
| IE (1) | IE61594B1 (esLanguage) |
| PT (1) | PT86652B (esLanguage) |
| ZA (1) | ZA88549B (esLanguage) |
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| CA2330611A1 (en) | 1998-05-22 | 1999-12-02 | The Board Of Trustees Of The Leland Stanford Junior University | Bifunctional molecules and therapies based thereon |
| JP2008539047A (ja) | 2005-04-28 | 2008-11-13 | プロテウス バイオメディカル インコーポレイテッド | ファーマインフォーマティックスシステム |
| US9062126B2 (en) | 2005-09-16 | 2015-06-23 | Raptor Pharmaceuticals Inc. | Compositions comprising receptor-associated protein (RAP) variants specific for CR-containing proteins and uses thereof |
| PT2398500T (pt) | 2009-02-20 | 2019-06-14 | 2 Bbb Medicines B V | Sistema de entrega de medicamentos à base de glutationas |
| CN102458374A (zh) | 2009-05-06 | 2012-05-16 | 实验室护肤股份有限公司 | 包含活性剂-磷酸钙颗粒复合物的皮肤递送组合物及其使用方法 |
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| US2897202A (en) * | 1956-03-19 | 1959-07-28 | Monsanto Chemicals | 3-keto-4-aza-delta5-steroids and method of preparing same |
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-
1987
- 1987-01-28 US US07/007,539 patent/US4888336A/en not_active Expired - Fee Related
-
1988
- 1988-01-26 DK DK037388A patent/DK37388A/da not_active IP Right Cessation
- 1988-01-26 DK DK037388D patent/DK168525B1/da not_active IP Right Cessation
- 1988-01-26 IE IE18988A patent/IE61594B1/en not_active IP Right Cessation
- 1988-01-27 JP JP63016790A patent/JPS63192800A/ja active Pending
- 1988-01-27 ZA ZA880549A patent/ZA88549B/xx unknown
- 1988-01-27 AT AT88300697T patent/ATE77388T1/de not_active IP Right Cessation
- 1988-01-27 CA CA000557453A patent/CA1325006C/en not_active Expired - Fee Related
- 1988-01-27 DE DE8888300697T patent/DE3871965T2/de not_active Expired - Fee Related
- 1988-01-27 EP EP88300697A patent/EP0277002B1/en not_active Expired - Lifetime
- 1988-01-27 AU AU10778/88A patent/AU608560B2/en not_active Ceased
- 1988-01-27 ES ES88300697T patent/ES2042725T3/es not_active Expired - Lifetime
- 1988-01-28 PT PT86652A patent/PT86652B/pt not_active IP Right Cessation
-
1991
- 1991-12-05 DK DK196691A patent/DK169438B1/da not_active IP Right Cessation
-
1992
- 1992-07-29 GR GR920401614T patent/GR3005284T3/el unknown
-
1994
- 1994-06-21 DK DK073594A patent/DK169840B1/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA88549B (en) | 1988-07-27 |
| PT86652B (pt) | 1992-02-28 |
| DK196691A (da) | 1991-12-05 |
| DK169840B1 (da) | 1995-03-13 |
| DK37388D0 (da) | 1988-01-26 |
| GR3005284T3 (esLanguage) | 1993-05-24 |
| DE3871965T2 (de) | 1993-01-14 |
| DE3871965D1 (de) | 1992-07-23 |
| JPS63192800A (ja) | 1988-08-10 |
| AU1077888A (en) | 1988-08-04 |
| EP0277002B1 (en) | 1992-06-17 |
| DK169438B1 (da) | 1994-10-31 |
| AU608560B2 (en) | 1991-04-11 |
| IE880189L (en) | 1988-07-28 |
| DK37388A (da) | 1988-07-29 |
| ATE77388T1 (de) | 1992-07-15 |
| CA1325006C (en) | 1993-12-07 |
| PT86652A (pt) | 1988-02-01 |
| EP0277002A2 (en) | 1988-08-03 |
| DK168525B1 (da) | 1994-04-11 |
| EP0277002A3 (en) | 1988-10-26 |
| US4888336A (en) | 1989-12-19 |
| DK196691D0 (da) | 1991-12-05 |
| ES2042725T3 (es) | 1993-12-16 |
| DK73594A (da) | 1994-06-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |