CS235959B2 - Method of 3-ketoandrosterones production - Google Patents
Method of 3-ketoandrosterones production Download PDFInfo
- Publication number
- CS235959B2 CS235959B2 CS826085A CS608582A CS235959B2 CS 235959 B2 CS235959 B2 CS 235959B2 CS 826085 A CS826085 A CS 826085A CS 608582 A CS608582 A CS 608582A CS 235959 B2 CS235959 B2 CS 235959B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- chloroform
- dien
- solution
- mixture
- ethylthio
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000007858 starting material Substances 0.000 claims description 13
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UUNNZQKYXLJLFV-LBLPMHNRSA-N (8s,9r,10s,11s,13s,14s)-17-butylsulfanyl-17-ethylsulfanyl-9-fluoro-11-hydroxy-10,13-dimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CCC(SCC)(SCCCC)[C@@]1(C)C[C@@H]2O UUNNZQKYXLJLFV-LBLPMHNRSA-N 0.000 claims 1
- 101100515513 Arabidopsis thaliana XI-E gene Proteins 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 230000000707 stereoselective effect Effects 0.000 claims 1
- MSEZLHAVPJYYIQ-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 MSEZLHAVPJYYIQ-VMXHOPILSA-N 0.000 abstract description 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 134
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- 239000000243 solution Substances 0.000 description 72
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000047 product Substances 0.000 description 33
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- 229910052757 nitrogen Inorganic materials 0.000 description 29
- 239000007787 solid Substances 0.000 description 21
- 229910052799 carbon Inorganic materials 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 17
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- 229910052717 sulfur Inorganic materials 0.000 description 13
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- 238000004458 analytical method Methods 0.000 description 12
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- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- IQUXBKUKXDWZLA-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 IQUXBKUKXDWZLA-VMXHOPILSA-N 0.000 description 6
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- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 6
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 6
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- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 4
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- 150000003573 thiols Chemical class 0.000 description 4
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- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- 229910052905 tridymite Inorganic materials 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS84576A CS235999B2 (cs) | 1981-08-20 | 1984-01-25 | Způsob výroby 3-ketoandrostenů |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/294,680 US4361559A (en) | 1981-08-20 | 1981-08-20 | Antiinflammatory 17,17-bis (substituted thio) androstenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS235959B2 true CS235959B2 (en) | 1985-05-15 |
Family
ID=23134474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS826085A CS235959B2 (en) | 1981-08-20 | 1982-08-19 | Method of 3-ketoandrosterones production |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4361559A (en]) |
| EP (1) | EP0073026B1 (en]) |
| JP (1) | JPS5841900A (en]) |
| KR (1) | KR890000678B1 (en]) |
| AT (1) | ATE18671T1 (en]) |
| AU (1) | AU564228B2 (en]) |
| CA (1) | CA1213270A (en]) |
| CS (1) | CS235959B2 (en]) |
| DD (3) | DD215086A5 (en]) |
| DE (1) | DE3269987D1 (en]) |
| DK (1) | DK165838C (en]) |
| ES (3) | ES515110A0 (en]) |
| FI (1) | FI78916C (en]) |
| GR (1) | GR76251B (en]) |
| HU (1) | HU187783B (en]) |
| IE (1) | IE53732B1 (en]) |
| IL (1) | IL66564A (en]) |
| NO (1) | NO159601C (en]) |
| NZ (1) | NZ201343A (en]) |
| PH (2) | PH18594A (en]) |
| PL (2) | PL244113A1 (en]) |
| PT (1) | PT75442B (en]) |
| SU (1) | SU1189353A3 (en]) |
| ZA (1) | ZA825260B (en]) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4447363A (en) * | 1982-07-07 | 1984-05-08 | E. R. Squibb & Sons, Inc. | Androstene-17-dithioketals |
| US4435326A (en) * | 1982-09-09 | 1984-03-06 | E. R. Squibb & Sons, Inc. | Intermediates useful in the preparation of 17,17-bis(substituted thio)androstenes |
| US4420428A (en) * | 1982-12-27 | 1983-12-13 | E. R. Squibb & Sons, Inc. | 16-Ketoandrostene-17-dithioketals |
| US4427592A (en) | 1983-01-31 | 1984-01-24 | E. R. Squibb & Sons, Inc. | Androstene-17-dithioketals |
| US4481144A (en) * | 1984-02-03 | 1984-11-06 | E. R. Squibb & Sons, Inc. | 17-Substituted thia-17-alkyl(or alkenyl or alkynyl)androstenes |
| US4499021A (en) * | 1984-04-12 | 1985-02-12 | E. R. Squibb & Sons, Inc. | 17β(Substituted thio)-16-ketoandrostene-17α..-carboxylic acid derivatives |
| US4529548A (en) * | 1984-05-07 | 1985-07-16 | E. R. Squibb & Sons, Inc. | 17β-(substituted thio)androstenes |
| US4529547A (en) * | 1984-06-20 | 1985-07-16 | E.R. Squibb & Sons, Inc. | 17-(substituted thio)-17-(substituted dithio)androstenes |
| US4528138A (en) * | 1984-06-20 | 1985-07-09 | E. R. Squibb & Sons, Inc. | 16-Keto-17-substituted thia-17-alkyl(or alkenyl or alkynyl) androstenes |
| US4891367A (en) * | 1987-04-22 | 1990-01-02 | Merrell Dow Pharmaceuticals Inc. | 17β-(cyclopropyloxy)androst-5-en-3β-ol and related compounds useful as C17-20 lyase inhibitors |
| US4868168A (en) * | 1987-11-13 | 1989-09-19 | E. R. Squibb & Sons, Inc. | Steroid ointment formulation |
| US4868169A (en) * | 1987-11-13 | 1989-09-19 | E. R. Squibb & Sons, Inc. | Steroid cream formulation |
| US5016635A (en) * | 1988-11-29 | 1991-05-21 | Sigmedics, Inc. Of Delaware | Control of FNS via pattern variations of response EMG |
| US4883792A (en) * | 1989-01-17 | 1989-11-28 | Peter Timmins | Steroid cream formulation |
| GB9103824D0 (en) * | 1991-02-23 | 1991-04-10 | Fisons Ag | Formulation |
| IE922301A1 (en) * | 1991-07-25 | 1993-01-27 | Squibb & Sons Inc | Selective thioketalization process, process for preparing¹thioenol ethers from thioketals, and process for the¹preparation of thioketals |
| DE4235220A1 (de) * | 1992-10-13 | 1994-06-16 | Schering Ag | Gestagen wirksame 19,11ß-überbrückte 4-Estrene |
| PL309402A1 (en) * | 1992-12-24 | 1995-10-02 | Rhone Poulenc Rorer Ltd | Novel steroides |
| US5439901A (en) * | 1993-07-23 | 1995-08-08 | The Procter & Gamble Company | Cyproterone thiopivalate |
| US5344651A (en) * | 1993-07-23 | 1994-09-06 | The Procter & Gamble Company | Cyproterone acetate thioacetate |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2840577A (en) * | 1956-12-21 | 1958-06-24 | Searle & Co | 17-thio derivatives of estratrien-3-ol and of estratetraen-3-ol |
| US2949477A (en) * | 1959-03-04 | 1960-08-16 | Searle & Co | 1, 3, 17-triacetoxyestra-1, 3, 5(10), 16-tetraene and congeners |
| US4094840A (en) * | 1977-05-12 | 1978-06-13 | E. R. Squibb & Sons, Inc. | 17-Alkylthio (and arylthio) androsteno[16α,17α-b]benzodioxin-3-ones |
| US4091036A (en) * | 1977-05-12 | 1978-05-23 | E. R. Squibb & Sons, Inc. | 17-Alkylthio (and arylthio)-1',2',3',4'-tetrahydroandrosteno [16 α, 17 α-b]naphthalenes and derivatives |
| US4133811A (en) * | 1978-02-17 | 1979-01-09 | E. R. Squibb & Sons, Inc. | 13-Alkylthio (and arylthio)-11,17-epoxy-17-methyl-18-norandrostenes |
| US4146538A (en) * | 1978-02-27 | 1979-03-27 | E. R. Squibb & Sons, Inc. | 17-Alkylthio (and arylthio) androsteno[17α,16α-b]benzopyran-3-ones and [16α,17α]naphthopyran-3-ones |
-
1981
- 1981-08-20 US US06/294,680 patent/US4361559A/en not_active Expired - Lifetime
-
1982
- 1982-07-19 CA CA000407557A patent/CA1213270A/en not_active Expired
- 1982-07-21 NZ NZ201343A patent/NZ201343A/en unknown
- 1982-07-22 ZA ZA825260A patent/ZA825260B/xx unknown
- 1982-07-22 AU AU86318/82A patent/AU564228B2/en not_active Ceased
- 1982-08-10 PH PH27702A patent/PH18594A/en unknown
- 1982-08-12 IE IE1951/82A patent/IE53732B1/en not_active IP Right Cessation
- 1982-08-12 GR GR69029A patent/GR76251B/el unknown
- 1982-08-17 PL PL24411382A patent/PL244113A1/xx unknown
- 1982-08-17 PL PL1982237936A patent/PL141303B1/pl unknown
- 1982-08-18 IL IL66564A patent/IL66564A/xx not_active IP Right Cessation
- 1982-08-18 HU HU822683A patent/HU187783B/hu not_active IP Right Cessation
- 1982-08-19 SU SU823480340A patent/SU1189353A3/ru active
- 1982-08-19 AT AT82107589T patent/ATE18671T1/de not_active IP Right Cessation
- 1982-08-19 CS CS826085A patent/CS235959B2/cs unknown
- 1982-08-19 ES ES515110A patent/ES515110A0/es active Granted
- 1982-08-19 DK DK372982A patent/DK165838C/da not_active IP Right Cessation
- 1982-08-19 NO NO822823A patent/NO159601C/no unknown
- 1982-08-19 DE DE8282107589T patent/DE3269987D1/de not_active Expired
- 1982-08-19 EP EP82107589A patent/EP0073026B1/en not_active Expired
- 1982-08-19 JP JP57144576A patent/JPS5841900A/ja active Granted
- 1982-08-19 FI FI822890A patent/FI78916C/fi not_active IP Right Cessation
- 1982-08-19 PT PT75442A patent/PT75442B/pt not_active IP Right Cessation
- 1982-08-19 KR KR8203735A patent/KR890000678B1/ko not_active Expired
- 1982-08-20 DD DD82257409A patent/DD215086A5/de not_active IP Right Cessation
- 1982-08-20 DD DD82242677A patent/DD211567A5/de not_active IP Right Cessation
- 1982-08-20 DD DD82257403A patent/DD215556A5/de not_active IP Right Cessation
-
1983
- 1983-04-29 ES ES521951A patent/ES521951A0/es active Granted
- 1983-04-29 ES ES521952A patent/ES521952A0/es active Granted
-
1984
- 1984-06-29 PH PH30900A patent/PH19857A/en unknown
Also Published As
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