IL38964A - 16,17-byclopropa androstanes,their preparation and pharmaceutical compositions containing them - Google Patents
16,17-byclopropa androstanes,their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL38964A IL38964A IL38964A IL3896472A IL38964A IL 38964 A IL38964 A IL 38964A IL 38964 A IL38964 A IL 38964A IL 3896472 A IL3896472 A IL 3896472A IL 38964 A IL38964 A IL 38964A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compounds
- prepared
- steroid
- acetoxy
- Prior art date
Links
- 150000001441 androstanes Chemical class 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000003431 steroids Chemical class 0.000 claims abstract 13
- 150000001875 compounds Chemical class 0.000 claims abstract 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract 7
- -1 difluorocarbene Chemical class 0.000 claims abstract 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001356 alkyl thiols Chemical class 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 150000002222 fluorine compounds Chemical class 0.000 claims 1
- 230000003054 hormonal effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 238000006266 etherification reaction Methods 0.000 abstract 2
- RGVHVYXPVVRNAJ-UHFFFAOYSA-N 3-(3-methylindol-1-yl)propanenitrile Chemical compound C1=CC=C2C(C)=CN(CCC#N)C2=C1 RGVHVYXPVVRNAJ-UHFFFAOYSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- QGXBDMJGAMFCBF-UHFFFAOYSA-N Etiocholanolone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 QGXBDMJGAMFCBF-UHFFFAOYSA-N 0.000 abstract 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 abstract 1
- 229910007565 Zn—Cu Inorganic materials 0.000 abstract 1
- 125000005035 acylthio group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000001195 anabolic effect Effects 0.000 abstract 1
- 230000001548 androgenic effect Effects 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 abstract 1
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 abstract 1
- QGXBDMJGAMFCBF-LUJOEAJASA-N epiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-LUJOEAJASA-N 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 238000000197 pyrolysis Methods 0.000 abstract 1
- MRTAVLDNYYEJHK-UHFFFAOYSA-M sodium;2-chloro-2,2-difluoroacetate Chemical compound [Na+].[O-]C(=O)C(F)(F)Cl MRTAVLDNYYEJHK-UHFFFAOYSA-M 0.000 abstract 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
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12458971A | 1971-03-15 | 1971-03-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL38964A0 IL38964A0 (en) | 1972-05-30 |
| IL38964A true IL38964A (en) | 1976-03-31 |
Family
ID=22415750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL38964A IL38964A (en) | 1971-03-15 | 1972-03-13 | 16,17-byclopropa androstanes,their preparation and pharmaceutical compositions containing them |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3732209A (OSRAM) |
| AU (1) | AU468273B2 (OSRAM) |
| BE (1) | BE780644A (OSRAM) |
| CA (1) | CA955929A (OSRAM) |
| CH (1) | CH579104A5 (OSRAM) |
| DE (1) | DE2212548A1 (OSRAM) |
| DK (1) | DK136829B (OSRAM) |
| FR (1) | FR2130285B1 (OSRAM) |
| GB (1) | GB1367384A (OSRAM) |
| IL (1) | IL38964A (OSRAM) |
| NL (1) | NL7202984A (OSRAM) |
| SE (1) | SE380028B (OSRAM) |
| ZA (1) | ZA721683B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980638A (en) * | 1974-09-20 | 1976-09-14 | The Upjohn Company | Testosterone derivatives |
| 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 |
| US5486511A (en) * | 1993-05-25 | 1996-01-23 | Merrell Dow Pharmaceuticals Inc. | 4-amino-17β-(cyclopropyloxy)androst-4-en-3-one, 4-amino-17β-(cyclopropylamino)androst-4-en-3-one and related compounds as C17-20 lyase and 5α-reductase |
| PT1343806E (pt) * | 2000-12-11 | 2008-07-04 | Organon Nv | Esteróides de metileno como novos androgénios |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1240078B (de) * | 1964-12-02 | 1967-05-11 | Schering Ag | Verfahren zur Herstellung von 16, 17-Methylen-delta 1,3,5(10)-oestratrien-derivaten |
| US3646074A (en) * | 1969-11-26 | 1972-02-29 | Searle & Co | 3 17-dioxygenated 16alpha 17alpha-methano-5alpha-androstanes and unsaturated congeners |
-
1971
- 1971-03-15 US US00124589A patent/US3732209A/en not_active Expired - Lifetime
-
1972
- 1972-02-11 CH CH203172A patent/CH579104A5/xx not_active IP Right Cessation
- 1972-03-07 NL NL7202984A patent/NL7202984A/xx not_active Application Discontinuation
- 1972-03-13 SE SE7203191A patent/SE380028B/xx unknown
- 1972-03-13 IL IL38964A patent/IL38964A/en unknown
- 1972-03-13 ZA ZA721683A patent/ZA721683B/xx unknown
- 1972-03-14 CA CA137,005A patent/CA955929A/en not_active Expired
- 1972-03-14 AU AU39980/72A patent/AU468273B2/en not_active Expired
- 1972-03-14 GB GB1177872A patent/GB1367384A/en not_active Expired
- 1972-03-14 BE BE780644A patent/BE780644A/xx unknown
- 1972-03-15 FR FR7209051A patent/FR2130285B1/fr not_active Expired
- 1972-03-15 DK DK121572AA patent/DK136829B/da unknown
- 1972-03-15 DE DE19722212548 patent/DE2212548A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2212548A1 (de) | 1972-09-21 |
| DK136829B (da) | 1977-11-28 |
| FR2130285A1 (OSRAM) | 1972-11-03 |
| SE380028B (OSRAM) | 1975-10-27 |
| DK136829C (OSRAM) | 1978-06-12 |
| CA955929A (en) | 1974-10-08 |
| AU468273B2 (en) | 1973-09-20 |
| AU3998072A (en) | 1973-09-20 |
| CH579104A5 (OSRAM) | 1976-08-31 |
| GB1367384A (en) | 1974-09-18 |
| ZA721683B (en) | 1972-12-27 |
| IL38964A0 (en) | 1972-05-30 |
| NL7202984A (OSRAM) | 1972-09-19 |
| FR2130285B1 (OSRAM) | 1975-06-20 |
| US3732209A (en) | 1973-05-08 |
| BE780644A (fr) | 1972-09-14 |
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