DE2207422A1 - 15alpha, 16alpha-methylen-5alpha-androstane - Google Patents
15alpha, 16alpha-methylen-5alpha-androstaneInfo
- Publication number
- DE2207422A1 DE2207422A1 DE19722207422 DE2207422A DE2207422A1 DE 2207422 A1 DE2207422 A1 DE 2207422A1 DE 19722207422 DE19722207422 DE 19722207422 DE 2207422 A DE2207422 A DE 2207422A DE 2207422 A1 DE2207422 A1 DE 2207422A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- androst
- group
- androstan
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LYQLGOGKDQKQAX-OJEXMJBDSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 LYQLGOGKDQKQAX-OJEXMJBDSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
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- -1 heterocyclic radical Chemical class 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
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- 239000002244 precipitate Substances 0.000 description 10
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- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
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- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
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- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
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- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE795239D BE795239A (fr) | 1972-02-11 | 15 alpha, 16 alpha-methylene-5alpha-androstanes et leur preparation | |
| DE19722207422 DE2207422A1 (de) | 1972-02-11 | 1972-02-11 | 15alpha, 16alpha-methylen-5alpha-androstane |
| DK24173A DK130988B (da) | 1972-02-11 | 1973-01-16 | Analogifremgangsmåde til fremstilling af 15alfa,16alfa-methylen-5alfa-androstan-3-on-17-oler. |
| AT112573A AT323345B (de) | 1972-02-11 | 1973-02-08 | Verfahren zur herstellung von neuen 15 alfa, 16 alfa-methylen-5 alfa-androstanen |
| CH186273A CH588506A5 (en:Method) | 1972-02-11 | 1973-02-09 | |
| NL7301923A NL7301923A (en:Method) | 1972-02-11 | 1973-02-09 | |
| FR7304679A FR2181720B1 (en:Method) | 1972-02-11 | 1973-02-09 | |
| GB681973A GB1426353A (en) | 1972-02-11 | 1973-02-12 | 15alpha,16alpha-methylene-5alpha-androstanes |
| JP1735673A JPS4886855A (en:Method) | 1972-02-11 | 1973-02-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722207422 DE2207422A1 (de) | 1972-02-11 | 1972-02-11 | 15alpha, 16alpha-methylen-5alpha-androstane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2207422A1 true DE2207422A1 (de) | 1973-08-16 |
Family
ID=5836212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722207422 Pending DE2207422A1 (de) | 1972-02-11 | 1972-02-11 | 15alpha, 16alpha-methylen-5alpha-androstane |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4886855A (en:Method) |
| AT (1) | AT323345B (en:Method) |
| BE (1) | BE795239A (en:Method) |
| CH (1) | CH588506A5 (en:Method) |
| DE (1) | DE2207422A1 (en:Method) |
| DK (1) | DK130988B (en:Method) |
| FR (1) | FR2181720B1 (en:Method) |
| GB (1) | GB1426353A (en:Method) |
| NL (1) | NL7301923A (en:Method) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1643035B2 (de) * | 1967-08-11 | 1976-01-15 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 15beta,16beta-methylen-5alpha -androst-l-ene, verfahren zu deren herstellung sowie diese enthaltende mittel |
-
0
- BE BE795239D patent/BE795239A/xx unknown
-
1972
- 1972-02-11 DE DE19722207422 patent/DE2207422A1/de active Pending
-
1973
- 1973-01-16 DK DK24173A patent/DK130988B/da unknown
- 1973-02-08 AT AT112573A patent/AT323345B/de not_active IP Right Cessation
- 1973-02-09 CH CH186273A patent/CH588506A5/xx not_active IP Right Cessation
- 1973-02-09 NL NL7301923A patent/NL7301923A/xx not_active Application Discontinuation
- 1973-02-09 FR FR7304679A patent/FR2181720B1/fr not_active Expired
- 1973-02-12 GB GB681973A patent/GB1426353A/en not_active Expired
- 1973-02-12 JP JP1735673A patent/JPS4886855A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7301923A (en:Method) | 1973-08-14 |
| AT323345B (de) | 1975-07-10 |
| JPS4886855A (en:Method) | 1973-11-15 |
| FR2181720B1 (en:Method) | 1975-11-21 |
| GB1426353A (en) | 1976-02-25 |
| DK130988C (en:Method) | 1975-10-13 |
| CH588506A5 (en:Method) | 1977-06-15 |
| DK130988B (da) | 1975-05-12 |
| FR2181720A1 (en:Method) | 1973-12-07 |
| BE795239A (fr) | 1973-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHN | Withdrawal |