CH621560A5 - Process for the preparation of 3-ketosteroids disubstituted in position 16 - Google Patents
Process for the preparation of 3-ketosteroids disubstituted in position 16 Download PDFInfo
- Publication number
- CH621560A5 CH621560A5 CH354376A CH354376A CH621560A5 CH 621560 A5 CH621560 A5 CH 621560A5 CH 354376 A CH354376 A CH 354376A CH 354376 A CH354376 A CH 354376A CH 621560 A5 CH621560 A5 CH 621560A5
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- CH
- Switzerland
- Prior art keywords
- carbon atoms
- group
- compound
- radicals
- formula
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- -1 hydroxy, acetoxy, propionyloxy, caproyloxy Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 4
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- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 229940074439 potassium sodium tartrate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto 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
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
-
- 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
-
- 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB11819/75A GB1538227A (en) | 1975-03-21 | 1975-03-21 | 16,16-disubstituted steroids of the androstene series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621560A5 true CH621560A5 (en) | 1981-02-13 |
Family
ID=9993275
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH354376A CH621560A5 (en) | 1975-03-21 | 1976-03-22 | Process for the preparation of 3-ketosteroids disubstituted in position 16 |
| CH228479A CH631996A5 (en) | 1975-03-21 | 1979-03-09 | Process for the preparation of 16-disubstituted steroids |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH228479A CH631996A5 (en) | 1975-03-21 | 1979-03-09 | Process for the preparation of 16-disubstituted steroids |
Country Status (15)
| Country | Link |
|---|---|
| JP (2) | JPS51118756A (en, 2012) |
| AT (1) | AT357700B (en, 2012) |
| AU (1) | AU501246B2 (en, 2012) |
| BE (1) | BE839751A (en, 2012) |
| CA (1) | CA1069498A (en, 2012) |
| CH (2) | CH621560A5 (en, 2012) |
| DE (1) | DE2610497C2 (en, 2012) |
| DK (1) | DK143757C (en, 2012) |
| FR (2) | FR2304345A1 (en, 2012) |
| GB (1) | GB1538227A (en, 2012) |
| IE (1) | IE42308B1 (en, 2012) |
| IL (2) | IL49132A (en, 2012) |
| NL (1) | NL184111C (en, 2012) |
| SE (2) | SE7603410L (en, 2012) |
| ZA (1) | ZA761324B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1602960A (en) * | 1977-05-25 | 1981-11-18 | Beecham Group Ltd | Process for preparing 16,16-disubstituted steroids of the androstene series |
| DE2943778A1 (de) * | 1979-10-26 | 1981-05-07 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | 17 (alpha) -alkylsteroide, diese enthaltende praeparate sowie verfahren zu ihrer herstellung |
| DE3514272A1 (de) * | 1985-04-17 | 1986-10-23 | Schering AG, 1000 Berlin und 4709 Bergkamen | Dermatica |
| GB9021546D0 (en) * | 1990-10-04 | 1990-11-21 | Beecham Group Plc | Novel composition |
| WO1992007586A1 (en) * | 1990-10-31 | 1992-05-14 | Beecham Group Plc | Topical composition with retinoid penetration enhancer |
| GB9205194D0 (en) * | 1992-03-10 | 1992-04-22 | Smithkline Beecham Plc | Novel composition |
| US20050009797A1 (en) * | 2001-12-19 | 2005-01-13 | Mitsuaki Nakamura | Androstane derivative having substituent in 7- abd 17--positions |
| CN108558975B (zh) * | 2018-04-26 | 2021-03-02 | 昆明理工大学 | 12β-羟基-雄甾4,14-二烯-16-酮类化合物及其应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3853926A (en) * | 1973-05-29 | 1974-12-10 | Searle & Co | 17{62 -hydroxy-16,16-dimethylester-4-en-3-one |
-
1975
- 1975-03-21 GB GB11819/75A patent/GB1538227A/en not_active Expired
-
1976
- 1976-03-01 IE IE412/76A patent/IE42308B1/en unknown
- 1976-03-02 IL IL49132A patent/IL49132A/xx unknown
- 1976-03-12 DE DE2610497A patent/DE2610497C2/de not_active Expired
- 1976-03-15 FR FR7607328A patent/FR2304345A1/fr active Granted
- 1976-03-16 AT AT191376A patent/AT357700B/de not_active IP Right Cessation
- 1976-03-18 BE BE165323A patent/BE839751A/xx not_active IP Right Cessation
- 1976-03-18 SE SE7603410A patent/SE7603410L/ not_active Application Discontinuation
- 1976-03-19 NL NLAANVRAGE7602949,A patent/NL184111C/xx not_active IP Right Cessation
- 1976-03-19 CA CA248,260A patent/CA1069498A/en not_active Expired
- 1976-03-19 JP JP51030741A patent/JPS51118756A/ja active Granted
- 1976-03-19 DK DK123476A patent/DK143757C/da active
- 1976-03-19 AU AU12207/76A patent/AU501246B2/en not_active Expired
- 1976-03-22 CH CH354376A patent/CH621560A5/de not_active IP Right Cessation
- 1976-04-04 ZA ZA761324A patent/ZA761324B/xx unknown
-
1979
- 1979-03-09 CH CH228479A patent/CH631996A5/de not_active IP Right Cessation
- 1979-03-13 SE SE7902256A patent/SE7902256L/ not_active Application Discontinuation
- 1979-10-19 IL IL58505A patent/IL58505A0/xx unknown
-
1980
- 1980-02-26 FR FR8004184A patent/FR2445340A1/fr active Granted
-
1985
- 1985-12-24 JP JP60291811A patent/JPS61178920A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2445340B1 (en, 2012) | 1983-02-11 |
| AU1220776A (en) | 1977-09-22 |
| CH631996A5 (en) | 1982-09-15 |
| IL49132A (en) | 1980-05-30 |
| JPS51118756A (en) | 1976-10-18 |
| DK123476A (da) | 1976-09-22 |
| JPS625920B2 (en, 2012) | 1987-02-07 |
| IE42308L (en) | 1976-09-21 |
| SE7902256L (sv) | 1979-03-13 |
| IE42308B1 (en) | 1980-07-16 |
| JPS6355488B2 (en, 2012) | 1988-11-02 |
| DE2610497C2 (de) | 1986-10-16 |
| ZA761324B (en) | 1977-02-23 |
| GB1538227A (en) | 1979-01-10 |
| JPS61178920A (ja) | 1986-08-11 |
| AU501246B2 (en) | 1979-06-14 |
| SE7603410L (sv) | 1976-09-22 |
| CA1069498A (en) | 1980-01-08 |
| DK143757B (da) | 1981-10-05 |
| FR2445340A1 (fr) | 1980-07-25 |
| BE839751A (fr) | 1976-09-20 |
| NL7602949A (nl) | 1976-09-23 |
| FR2304345B1 (en, 2012) | 1980-11-07 |
| IL58505A0 (en) | 1980-01-31 |
| NL184111B (nl) | 1988-11-16 |
| DE2610497A1 (de) | 1976-10-07 |
| FR2304345A1 (fr) | 1976-10-15 |
| NL184111C (nl) | 1989-04-17 |
| DK143757C (da) | 1982-03-22 |
| AT357700B (de) | 1980-07-25 |
| ATA191376A (de) | 1979-12-15 |
| IL49132A0 (en) | 1976-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |