GB956251A - A process for introducing a í¸ dienic system into a 3-keto í¸ 19-nor steroid and novel 19-nor-4,9(10) - steroids and process of making them - Google Patents
A process for introducing a í¸ dienic system into a 3-keto í¸ 19-nor steroid and novel 19-nor-4,9(10) - steroids and process of making themInfo
- Publication number
- GB956251A GB956251A GB2356/61A GB235661A GB956251A GB 956251 A GB956251 A GB 956251A GB 2356/61 A GB2356/61 A GB 2356/61A GB 235661 A GB235661 A GB 235661A GB 956251 A GB956251 A GB 956251A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxyl
- keto
- group
- pyridine
- vinyl
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 10
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 3
- 239000012442 inert solvent Substances 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 3
- 229920002554 vinyl polymer Polymers 0.000 abstract 3
- MNDSSKADVGDFDF-UHFFFAOYSA-N 2,4,5-trimethylpyridine Chemical compound CC1=CC(C)=C(C)C=N1 MNDSSKADVGDFDF-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 235000006408 oxalic acid Nutrition 0.000 abstract 2
- 150000003431 steroids Chemical class 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000007269 dehydrobromination reaction Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 229960001566 methyltestosterone Drugs 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 0.000 abstract 1
- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- 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
- A61K31/569—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 substituted in position 17 alpha, e.g. ethisterone
-
- 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- 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
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4001A US3086027A (en) | 1960-01-22 | 1960-01-22 | 19-nor-4, 9(10)-steroids and process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB956251A true GB956251A (en) | 1964-04-22 |
Family
ID=21708638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2356/61A Expired GB956251A (en) | 1960-01-22 | 1961-01-20 | A process for introducing a í¸ dienic system into a 3-keto í¸ 19-nor steroid and novel 19-nor-4,9(10) - steroids and process of making them |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3086027A (https=) |
| BE (1) | BE599411A (https=) |
| CH (1) | CH402846A (https=) |
| FR (1) | FR993M (https=) |
| GB (1) | GB956251A (https=) |
| OA (1) | OA03370A (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3250793A (en) * | 1963-06-19 | 1966-05-10 | Merck & Co Inc | 17alpha-halogenated hydrocarbon derivatives of estra-4, 9-diene 3beta, 17-diols |
| US3211764A (en) * | 1963-09-25 | 1965-10-12 | American Cyanamid Co | 19-norandrostadienes and method of preparing the same |
| US3424745A (en) * | 1964-05-27 | 1969-01-28 | Roussel Uclaf | Novel process for the preparation of trienic steroid derivatives |
| BE665514A (https=) * | 1964-06-16 | |||
| NL127071C (https=) * | 1964-12-31 | |||
| NL6517141A (https=) * | 1964-12-31 | 1966-07-04 | ||
| US3370071A (en) * | 1965-06-01 | 1968-02-20 | Merck & Co Inc | 3-keto-13beta-alkyl-17beta-acetyl-gona-4, 9-dienes and process |
| US3424768A (en) * | 1965-08-17 | 1969-01-28 | Searle & Co | 17alpha-alkynylestra-4,9(10)-diene-3beta,17beta-diols and esters thereof |
| US3423404A (en) * | 1965-10-21 | 1969-01-21 | Searle & Co | (optionally 17-alkylated) estra-4,9(10)-diene - 3alpha/3beta,17beta - diols and esters corresponding |
| GB1108276A (en) * | 1966-03-14 | 1968-04-03 | British Drug Houses Ltd | 17ª‡-alka-1',3'-diynyl-oestra-4,9(10)-dien-3-ones |
| US3424769A (en) * | 1966-04-04 | 1969-01-28 | Syntex Corp | Process for the preparation of novel 6alpha-methyl-delta4,9(10)- diene steroids |
| US3461118A (en) * | 1966-10-17 | 1969-08-12 | Syntex Corp | 3beta-tetrahydrofuranyloxy - and 3beta-tetrahydropyranyloxyestra - 4,9(10) - dienes and -4,9(10),11-trienes,their preparation and intermediates thereof |
| US3875188A (en) * | 1968-04-10 | 1975-04-01 | Eugene E Galantay | 17-Beta-alpha-lower alkyl allene-substituted steroids |
| US3761591A (en) * | 1970-02-20 | 1973-09-25 | Roussel Uclaf | Novel pregnadiene |
| FR2407940A1 (fr) * | 1977-11-08 | 1979-06-01 | Roussel Uclaf | Nouveaux derives steroides 17 a-aryle, ou 17 a-heteroaryle, leur procede de preparation et leur application comme medicament |
| US4157349A (en) * | 1978-03-13 | 1979-06-05 | Sterling Drug Inc. | Dehydrohalogenation process |
| DE3027908A1 (de) * | 1980-07-21 | 1982-03-18 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 16 (beta) -ethylsteroide, diese enthaltende praeparate und verfahren zu ihrer herstellung |
| FR2495621A1 (fr) * | 1980-12-05 | 1982-06-11 | Roussel Uclaf | Nouveaux derives de l'estra 4,9-diene, leur procede de preparation et leur application comme medicaments |
| EP1163259B1 (en) * | 1999-03-08 | 2002-11-20 | Akzo Nobel N.V. | 14.beta.,17-alpha-hydroxymethylandrostane derivatives as androgens |
| ES2258037T3 (es) * | 1999-12-02 | 2006-08-16 | Akzo Nobel N.V. | Androgenos sustituidos con 14,15-beta-metilen. |
| BR0016092A (pt) | 1999-12-02 | 2002-07-30 | Akzo Nobel Nv | Composto, uso de um composto kit para contracepção hormonal em um macho, e, método de tratamento |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2729654A (en) * | 1954-05-19 | 1956-01-03 | Searle & Co | 10-hydroxy-3-ketosteroids |
-
1960
- 1960-01-22 US US4001A patent/US3086027A/en not_active Expired - Lifetime
-
1961
- 1961-01-20 GB GB2356/61A patent/GB956251A/en not_active Expired
- 1961-01-20 FR FR850341A patent/FR993M/fr active Active
- 1961-01-21 CH CH70261A patent/CH402846A/de unknown
- 1961-01-23 BE BE599411A patent/BE599411A/fr unknown
-
1967
- 1967-03-30 OA OA52885A patent/OA03370A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR993M (https=) | 1961-12-11 |
| OA03370A (fr) | 1970-12-15 |
| CH402846A (de) | 1965-11-30 |
| US3086027A (en) | 1963-04-16 |
| BE599411A (fr) | 1961-07-24 |
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