IE52686B1 - 17alpha-substituted steroids,pharmaceutical preparations containing them and process for their manufacture - Google Patents
17alpha-substituted steroids,pharmaceutical preparations containing them and process for their manufactureInfo
- Publication number
- IE52686B1 IE52686B1 IE2202/80A IE220280A IE52686B1 IE 52686 B1 IE52686 B1 IE 52686B1 IE 2202/80 A IE2202/80 A IE 2202/80A IE 220280 A IE220280 A IE 220280A IE 52686 B1 IE52686 B1 IE 52686B1
- Authority
- IE
- Ireland
- Prior art keywords
- methyl
- androstan
- propyl
- group
- hydroxy
- Prior art date
Links
- 150000003431 steroids Chemical class 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000000825 pharmaceutical preparation Chemical class 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 11
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000002252 acyl group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 150000002902 organometallic compounds Chemical class 0.000 claims description 5
- VMNRNUNYBVFVQI-QYXZOKGRSA-N (5s,8s,9s,10s,13s,14s)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 VMNRNUNYBVFVQI-QYXZOKGRSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 claims 1
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- 239000001301 oxygen Substances 0.000 abstract 1
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- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004890 malting Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009256 replacement therapy Methods 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/0037—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0044—Alkenyl derivatives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Medicines Containing Plant Substances (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792943776 DE2943776A1 (de) | 1979-10-26 | 1979-10-26 | 17 (alpha) -alkylsteroide, diese enthaltende praeparate sowie verfahren zu ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE802202L IE802202L (en) | 1981-04-26 |
| IE52686B1 true IE52686B1 (en) | 1988-01-20 |
Family
ID=6084722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2202/80A IE52686B1 (en) | 1979-10-26 | 1980-10-24 | 17alpha-substituted steroids,pharmaceutical preparations containing them and process for their manufacture |
Country Status (23)
| Country | Link |
|---|---|
| US (4) | US4344941A (en, 2012) |
| EP (1) | EP0027961B1 (en, 2012) |
| JP (1) | JPS5673097A (en, 2012) |
| AT (1) | ATE2221T1 (en, 2012) |
| AU (1) | AU532515B2 (en, 2012) |
| CA (1) | CA1160216A (en, 2012) |
| CS (1) | CS228507B2 (en, 2012) |
| DD (1) | DD153694A5 (en, 2012) |
| DE (2) | DE2943776A1 (en, 2012) |
| DK (1) | DK163002C (en, 2012) |
| EG (1) | EG14998A (en, 2012) |
| ES (1) | ES8106539A1 (en, 2012) |
| FI (1) | FI69850C (en, 2012) |
| GR (1) | GR71212B (en, 2012) |
| HU (1) | HU183237B (en, 2012) |
| IE (1) | IE52686B1 (en, 2012) |
| IL (1) | IL61332A (en, 2012) |
| NO (1) | NO154231C (en, 2012) |
| PL (1) | PL125169B1 (en, 2012) |
| PT (1) | PT71842B (en, 2012) |
| SU (1) | SU973025A3 (en, 2012) |
| YU (1) | YU256680A (en, 2012) |
| ZA (1) | ZA806565B (en, 2012) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2943776A1 (de) * | 1979-10-26 | 1981-05-14 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | 17 (alpha) -alkylsteroide, diese enthaltende praeparate sowie verfahren zu ihrer herstellung |
| DE3115996A1 (de) * | 1981-04-13 | 1982-11-04 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 17(alpha)-alkyl-17(beta)-hydroxy-1(alpha)- methyl-4-androsten-3-one-.verfahren zu ihrer herstellung und pharmazeutische praeparate, die diese verbindungen enthalten |
| DE3322285A1 (de) * | 1983-06-18 | 1984-12-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1-alkyl-androsta-1,4-dien-3,17-dione, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate |
| US4885289A (en) * | 1983-12-12 | 1989-12-05 | Breuer Miklos M | Alteration of character of male beard growth |
| US5723502A (en) * | 1985-07-18 | 1998-03-03 | Proctor; Peter H. | Topical spin trap composition and method |
| US5470876A (en) * | 1985-07-18 | 1995-11-28 | Proctor; Peter H. | Topical sod for treating hair loss |
| US5728714A (en) * | 1985-07-18 | 1998-03-17 | Proctor; Peter H. | Method for treating hair loss using tempo |
| US6150405A (en) * | 1985-07-18 | 2000-11-21 | Proctor; Peter H. | Hair loss treatment with ascorbates |
| US5352442A (en) * | 1985-07-18 | 1994-10-04 | Proctor Peter H | Topical tempo |
| US5472687A (en) * | 1985-07-18 | 1995-12-05 | Proctor; Peter H. | Topical pyridine N-oxides |
| US5714510A (en) * | 1985-07-18 | 1998-02-03 | Proctor; Peter H. | Topical proxyl composition and method |
| US5716947A (en) * | 1985-07-18 | 1998-02-10 | Proctor; Peter H. | Topical doxyl composition and method |
| US5714482A (en) * | 1985-07-18 | 1998-02-03 | Proctor; Peter H. | Topical spin labels and method |
| US4898694A (en) * | 1987-11-25 | 1990-02-06 | Schwartz Arthur G | 17-Hydroxy-steroids |
| DE3824247A1 (de) * | 1988-07-13 | 1990-01-18 | Schering Ag | Neue androstan-derivate |
| EP0499779B1 (de) * | 1991-01-24 | 1996-09-11 | Rheinbraun Aktiengesellschaft | Verfahren zum Behandeln von Abfällen |
| US5328686A (en) * | 1991-10-30 | 1994-07-12 | Douglas Shander | Treatment of acne or of pseudofolliculitis barbae |
| ATE218273T1 (de) * | 1991-11-05 | 2002-06-15 | Gillette Co | Veränderung der geschindigkeit und der art des haarwuchses |
| US5364885A (en) * | 1992-11-13 | 1994-11-15 | Ahluwalia Gurpreet S | Reduction of hair growth |
| US5411991A (en) * | 1992-12-22 | 1995-05-02 | Shander; Douglas | Method of reducing hair growth employing sulfhydryl active compounds |
| US6743419B1 (en) | 1992-12-22 | 2004-06-01 | The Gillette Company | Method of reducing hair growth employing sulfhydryl active compounds |
| US5648394A (en) * | 1993-05-27 | 1997-07-15 | Boxall; Brian Alfred | Topical composition for inhibiting hair growth |
| US6414017B2 (en) | 1993-05-28 | 2002-07-02 | The Gillette Company | Inhibition of hair growth |
| US6248751B1 (en) | 1993-05-28 | 2001-06-19 | Gurpreet S. Ahluwalia | Inhibition of hair growth |
| WO1995018821A2 (en) * | 1994-01-06 | 1995-07-13 | Sri International | Novel antiandrogenic agents and related pharmaceutical compositions and methods of use |
| US5474763A (en) * | 1994-03-11 | 1995-12-12 | Shander; Douglas | Reduction of hair growth |
| US5455234A (en) * | 1994-03-16 | 1995-10-03 | Ahluwalia; Gurpreet S. | Inhibition of hair growth |
| US5468476A (en) * | 1994-03-16 | 1995-11-21 | Ahluwalia; Gurpreet S. | Reduction of hair growth |
| ES2175084T3 (es) * | 1995-02-28 | 2002-11-16 | Gillette Co | Uso de supresores de angiogenesis para inhibir el crecimiento del pelo. |
| US5674477A (en) * | 1995-02-28 | 1997-10-07 | Ahluwalia; Gurpreet S. | Reduction of hair growth |
| US5728736A (en) * | 1995-11-29 | 1998-03-17 | Shander; Douglas | Reduction of hair growth |
| US5652273A (en) * | 1995-11-30 | 1997-07-29 | Henry; James | Reduction of hair growth |
| ATE473759T1 (de) | 1998-05-22 | 2010-07-15 | Univ Leland Stanford Junior | Bifunktionelle moleküle sowie darauf basierende therapien. |
| US6294188B1 (en) | 1998-07-09 | 2001-09-25 | Aviana Biopharm Inc. | Methods involving changing the constitutive and stimulated secretions of the local reproductive system of women |
| US20070129282A1 (en) * | 1998-11-24 | 2007-06-07 | Ahlem Clarence N | Pharmaceutical treatments and compositions |
| PT1955700E (pt) * | 1999-09-30 | 2011-05-04 | Harbor Biosciences Inc | Tratamento terap?utico de doen?as associadas ao receptor de androg?nios |
| US7285109B2 (en) * | 2003-02-13 | 2007-10-23 | Boston Scientific Scimed, Inc. | Device and method for collapsing an angioplasty balloon |
| DK1889198T3 (da) | 2005-04-28 | 2015-02-09 | Proteus Digital Health Inc | Farma-informatiksystem |
| 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 |
| NZ616673A (en) | 2009-02-20 | 2014-08-29 | To Bbb Holding B V | Glutathione-based drug delivery system |
| MX2011011833A (es) | 2009-05-06 | 2012-01-27 | Lab Skin Care Inc | Composiciones de administración dérmica que comprenden complejos de partículas de fosfato de calcio-agente activo y métodos para utilizar las mismas. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1382468A (fr) * | 1964-01-28 | 1964-12-18 | Spofa Vereinigte Pharma Werke | Procédé de préparation des composés de 3-céto-androstane 1-méthyle-substitués, et produits conformes à ceux obtenus par le présent procédé ou procédé similaire |
| US3391168A (en) * | 1965-08-23 | 1968-07-02 | Searle & Co | 1, 17-dimethyl-5-androstane-3beta, 17beta-diol and esters thereof |
| US3705180A (en) * | 1971-09-02 | 1972-12-05 | Paul D Klimstra | 17-oxygenate-2-alpha-methyl-2-methylen-5 alpha-androstan-3-ones and intermediates |
| US4039669A (en) * | 1975-08-01 | 1977-08-02 | Sterling Drug Inc. | Composition for topical application and use thereof |
| DE2943776A1 (de) * | 1979-10-26 | 1981-05-14 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | 17 (alpha) -alkylsteroide, diese enthaltende praeparate sowie verfahren zu ihrer herstellung |
-
1979
- 1979-10-26 DE DE19792943776 patent/DE2943776A1/de not_active Withdrawn
-
1980
- 1980-09-26 PT PT71842A patent/PT71842B/pt unknown
- 1980-10-07 YU YU02566/80A patent/YU256680A/xx unknown
- 1980-10-08 ES ES495740A patent/ES8106539A1/es not_active Expired
- 1980-10-09 SU SU802989151A patent/SU973025A3/ru active
- 1980-10-14 DK DK434380A patent/DK163002C/da not_active IP Right Cessation
- 1980-10-16 DE DE8080106289T patent/DE3061638D1/de not_active Expired
- 1980-10-16 AT AT80106289T patent/ATE2221T1/de not_active IP Right Cessation
- 1980-10-16 EP EP80106289A patent/EP0027961B1/de not_active Expired
- 1980-10-20 US US06/198,383 patent/US4344941A/en not_active Expired - Lifetime
- 1980-10-22 DD DD80224695A patent/DD153694A5/de not_active IP Right Cessation
- 1980-10-23 PL PL1980227468A patent/PL125169B1/pl unknown
- 1980-10-23 IL IL61332A patent/IL61332A/xx not_active IP Right Cessation
- 1980-10-23 AU AU63637/80A patent/AU532515B2/en not_active Ceased
- 1980-10-24 HU HU802577A patent/HU183237B/hu not_active IP Right Cessation
- 1980-10-24 GR GR63214A patent/GR71212B/el unknown
- 1980-10-24 ZA ZA00806565A patent/ZA806565B/xx unknown
- 1980-10-24 IE IE2202/80A patent/IE52686B1/en not_active IP Right Cessation
- 1980-10-24 NO NO803172A patent/NO154231C/no unknown
- 1980-10-24 FI FI803342A patent/FI69850C/fi not_active IP Right Cessation
- 1980-10-26 EG EG651/80A patent/EG14998A/xx active
- 1980-10-27 CA CA000363342A patent/CA1160216A/en not_active Expired
- 1980-10-27 JP JP14949780A patent/JPS5673097A/ja active Granted
- 1980-10-27 CS CS807263A patent/CS228507B2/cs unknown
-
1982
- 1982-05-20 US US06/380,328 patent/US4456600A/en not_active Expired - Lifetime
-
1984
- 1984-06-13 US US06/620,216 patent/US4558041A/en not_active Expired - Fee Related
-
1986
- 1986-10-14 US US06/918,231 patent/US4892867A/en not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |