GB1310611A - Propadienyl steroids and method for their production - Google Patents
Propadienyl steroids and method for their productionInfo
- Publication number
- GB1310611A GB1310611A GB1767570A GB1767570A GB1310611A GB 1310611 A GB1310611 A GB 1310611A GB 1767570 A GB1767570 A GB 1767570A GB 1767570 A GB1767570 A GB 1767570A GB 1310611 A GB1310611 A GB 1310611A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- estra
- steroids
- homologues
- dien
- 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
- -1 Propadienyl steroids Chemical class 0.000 title abstract 6
- 238000000034 method Methods 0.000 title abstract 3
- 150000003431 steroids Chemical class 0.000 abstract 4
- 238000006266 etherification reaction Methods 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 229960001124 trientine Drugs 0.000 abstract 2
- ZPCWNEBIFWQYBE-MDMHHNQBSA-N (8R,9S,10R,13S,14S)-3-ethoxy-13-methyl-1,2,7,8,9,10,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene Chemical class C(C)OC1=CC2=CC[C@H]3[C@@H]4CCC[C@@]4(C)CC[C@@H]3[C@H]2CC1 ZPCWNEBIFWQYBE-MDMHHNQBSA-N 0.000 abstract 1
- SBYZSMHTTSGGLZ-JRRWAFEKSA-N (8R,9S,10R,13S,14S)-3-ethoxy-6-fluoro-13-methyl-2,7,8,9,10,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-one Chemical compound C(C)OC1=CC2=C(C[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@H]2CC1)=O)F SBYZSMHTTSGGLZ-JRRWAFEKSA-N 0.000 abstract 1
- FGNDENOPQCWVIW-NPCUJANDSA-N (8R,9S,10R,13S,14S)-6,6-difluoro-13-methyl-2,3,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene Chemical compound FC1(C[C@H]2[C@@H]3CCC[C@@]3(C)CC[C@@H]2[C@H]2CCCC=C12)F FGNDENOPQCWVIW-NPCUJANDSA-N 0.000 abstract 1
- QYLJNAMKKXVXBU-JAYZULETSA-N (8r,9s,10r,13s,14s)-3-ethoxy-13-methyl-2,7,8,9,10,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1C[C@@H]2[C@@H](CCC(OCC)=C3)C3=CC[C@H]2[C@@H]2CCC(=O)[C@]21C QYLJNAMKKXVXBU-JAYZULETSA-N 0.000 abstract 1
- ZPCFANFAGBOXIN-MAKQCAJESA-N (8r,9s,10r,13s,14s)-6,6-difluoro-13-methyl-2,7,8,9,10,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(F)(F)C2=C1 ZPCFANFAGBOXIN-MAKQCAJESA-N 0.000 abstract 1
- LAOZHKKMOJSCKC-SQNIBIBYSA-N (8s,13s,14s)-13-methyl-1,2,3,6,7,8,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene Chemical compound C1CC2=CCCCC2=C2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 LAOZHKKMOJSCKC-SQNIBIBYSA-N 0.000 abstract 1
- JRIZOGLBRPZBLQ-QXUSFIETSA-N 19-Norandrostenedione Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JRIZOGLBRPZBLQ-QXUSFIETSA-N 0.000 abstract 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 abstract 1
- HRDCVMSNCBAMAM-UHFFFAOYSA-N 3-prop-2-ynoxyprop-1-yne Chemical class C#CCOCC#C HRDCVMSNCBAMAM-UHFFFAOYSA-N 0.000 abstract 1
- FSMHNRHLQAABPS-UHFFFAOYSA-N 4-methoxy-3,6-dihydro-2h-pyran Chemical compound COC1=CCOCC1 FSMHNRHLQAABPS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- BHTWZQKERRCPRZ-RYRKJORJSA-N Estra-4,9-diene-3,17-dione Chemical compound C1CC(=O)C=C2CC[C@@H]([C@H]3[C@@](C)(C(CC3)=O)CC3)C3=C21 BHTWZQKERRCPRZ-RYRKJORJSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910000091 aluminium hydride Inorganic materials 0.000 abstract 1
- 150000001441 androstanes Chemical class 0.000 abstract 1
- 230000002280 anti-androgenic effect Effects 0.000 abstract 1
- 230000003509 anti-fertility effect Effects 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002085 enols Chemical class 0.000 abstract 1
- 230000001076 estrogenic effect Effects 0.000 abstract 1
- 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 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 abstract 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000001817 pituitary effect Effects 0.000 abstract 1
- 230000001072 progestational effect Effects 0.000 abstract 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 abstract 1
- 230000009467 reduction Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 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
- A61K31/567—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 position 17 alpha, e.g. mestranol, norethandrolone
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material 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)
- Organic Chemistry (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81756369A | 1969-04-18 | 1969-04-18 | |
| US87752169A | 1969-11-17 | 1969-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1310611A true GB1310611A (en) | 1973-03-21 |
Family
ID=27124181
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1767570A Expired GB1310611A (en) | 1969-04-18 | 1970-04-14 | Propadienyl steroids and method for their production |
| GB4115872A Expired GB1310612A (en) | 1969-04-18 | 1970-04-14 | 17alpha-3-substituted propynyl steroids |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4115872A Expired GB1310612A (en) | 1969-04-18 | 1970-04-14 | 17alpha-3-substituted propynyl steroids |
Country Status (15)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH571537A5 (enrdf_load_stackoverflow) * | 1970-04-24 | 1976-01-15 | Sandoz Ag | |
| GB1348186A (en) * | 1970-04-24 | 1974-03-13 | Sandoz Ltd | 17alpha-propadienyl steroids |
-
1970
- 1970-04-02 IL IL34228A patent/IL34228A/xx unknown
- 1970-04-06 CA CA079239A patent/CA919167A/en not_active Expired
- 1970-04-13 FI FI701016A patent/FI47985C/fi active
- 1970-04-14 GB GB1767570A patent/GB1310611A/en not_active Expired
- 1970-04-14 GB GB4115872A patent/GB1310612A/en not_active Expired
- 1970-04-15 DE DE19702018055 patent/DE2018055B2/de active Pending
- 1970-04-15 CH CH560270A patent/CH540894A/de not_active IP Right Cessation
- 1970-04-15 AT AT342970A patent/AT322120B/de not_active IP Right Cessation
- 1970-04-16 BE BE749067D patent/BE749067A/xx unknown
- 1970-04-17 JP JP45032883A patent/JPS4916857B1/ja active Pending
- 1970-04-17 ES ES378764A patent/ES378764A1/es not_active Expired
- 1970-04-17 NL NL7005604A patent/NL7005604A/xx unknown
- 1970-04-17 NO NO1467/70A patent/NO134553C/no unknown
- 1970-04-17 DK DK195170A patent/DK133813C/da active
- 1970-04-17 FR FR707014098A patent/FR2051496B1/fr not_active Expired
- 1970-04-17 SE SE05322/70A patent/SE355802B/xx unknown
-
1974
- 1974-01-29 IL IL44105A patent/IL44105A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI47985C (fi) | 1974-05-10 |
| FR2051496B1 (enrdf_load_stackoverflow) | 1973-03-16 |
| DE2018055B2 (de) | 1976-12-23 |
| IL34228A0 (en) | 1970-06-17 |
| JPS4916857B1 (enrdf_load_stackoverflow) | 1974-04-25 |
| DE2018055A1 (de) | 1970-10-22 |
| GB1310612A (en) | 1973-03-21 |
| DK133813B (da) | 1976-07-26 |
| NO134553C (enrdf_load_stackoverflow) | 1976-11-03 |
| CA919167A (en) | 1973-01-16 |
| IL34228A (en) | 1975-04-25 |
| FI47985B (enrdf_load_stackoverflow) | 1974-01-31 |
| DK133813C (da) | 1976-12-13 |
| ES378764A1 (es) | 1973-02-01 |
| AT322120B (de) | 1975-05-12 |
| NL7005604A (enrdf_load_stackoverflow) | 1970-10-20 |
| CH540894A (de) | 1973-08-31 |
| IL44105A0 (en) | 1974-05-16 |
| SE355802B (enrdf_load_stackoverflow) | 1973-05-07 |
| NO134553B (enrdf_load_stackoverflow) | 1976-07-26 |
| FR2051496A1 (enrdf_load_stackoverflow) | 1971-04-09 |
| BE749067A (fr) | 1970-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |