GB780301A - Manufacture of steroids with oxygen in 11-position - Google Patents
Manufacture of steroids with oxygen in 11-positionInfo
- Publication number
- GB780301A GB780301A GB25355/53A GB2535553A GB780301A GB 780301 A GB780301 A GB 780301A GB 25355/53 A GB25355/53 A GB 25355/53A GB 2535553 A GB2535553 A GB 2535553A GB 780301 A GB780301 A GB 780301A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetoxy
- acid
- trichloracetoxy
- methyl ester
- hydroxy
- 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 229910052760 oxygen Inorganic materials 0.000 title 1
- 239000001301 oxygen Substances 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- XIIAYQZJNBULGD-UHFFFAOYSA-N (5alpha)-cholestane Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 XIIAYQZJNBULGD-UHFFFAOYSA-N 0.000 abstract 2
- JWMFYGXQPXQEEM-GCOKGBOCSA-N 5α-pregnane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-GCOKGBOCSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- WAAWMJYYKITCGF-WTPIMUJOSA-N 5alpha-ergostane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@H](C)C(C)C)[C@@]2(C)CC1 WAAWMJYYKITCGF-WTPIMUJOSA-N 0.000 abstract 1
- GKBHKNPLNHLYHT-UHFFFAOYSA-N 5beta-Stigmastan Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 GKBHKNPLNHLYHT-UHFFFAOYSA-N 0.000 abstract 1
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 abstract 1
- QSHQKIURKJITMZ-VVVZRFTHSA-N 5α-cholane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCC)[C@@]2(C)CC1 QSHQKIURKJITMZ-VVVZRFTHSA-N 0.000 abstract 1
- QZLYKIGBANMMBK-DYKIIFRCSA-N 5β-androstane Chemical class C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-DYKIIFRCSA-N 0.000 abstract 1
- QSHQKIURKJITMZ-OBUPQJQESA-N 5β-cholane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCC)[C@@]2(C)CC1 QSHQKIURKJITMZ-OBUPQJQESA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- XIIAYQZJNBULGD-LDHZKLTISA-N cholestane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XIIAYQZJNBULGD-LDHZKLTISA-N 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 abstract 1
- LBBIAJCNVBWXHN-NZJNOUNASA-N methyl (4R)-4-[(3R,8S,9S,10S,11R,12R,13R,14S,17R)-3-acetyloxy-12-hydroxy-10,13-dimethyl-11-(2,2,2-trichloroacetyl)oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate Chemical compound COC(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](CC[C@]4(C)[C@H]3[C@H]([C@@H]([C@]12C)O)OC(C(Cl)(Cl)Cl)=O)OC(C)=O)=O LBBIAJCNVBWXHN-NZJNOUNASA-N 0.000 abstract 1
- FKEDTKXWEOKYFM-NCRMOOSUSA-N methyl (4R)-4-[(8R,9S,10S,12S,13R,14S,17R)-12-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate Chemical compound COC(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3C[C@@H]([C@]12C)O)=O FKEDTKXWEOKYFM-NCRMOOSUSA-N 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- -1 sitostane Chemical compound 0.000 abstract 1
- INLFWQCRAJUDCR-LYLBMTSKSA-N spirostane Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 INLFWQCRAJUDCR-LYLBMTSKSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- GKBHKNPLNHLYHT-LWQAOISPSA-N stigmastane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 GKBHKNPLNHLYHT-LWQAOISPSA-N 0.000 abstract 1
- LAGFCVRVICMFFF-UHFFFAOYSA-N stigmastane Natural products CCC(CCC(C)C1CCC2C3CCC4CC(=O)CC(C)C4C3CCC12C)C(C)C LAGFCVRVICMFFF-UHFFFAOYSA-N 0.000 abstract 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 abstract 1
- 229960004319 trichloroacetic acid Drugs 0.000 abstract 1
- XIIAYQZJNBULGD-CJPSHIORSA-N β-cholestane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 XIIAYQZJNBULGD-CJPSHIORSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
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 |
|---|---|---|---|
| CH309920T | 1952-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB780301A true GB780301A (en) | 1957-07-31 |
Family
ID=4493996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25355/53A Expired GB780301A (en) | 1952-09-18 | 1953-09-04 | Manufacture of steroids with oxygen in 11-position |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2776302A (OSRAM) |
| CH (1) | CH309920A (OSRAM) |
| DE (1) | DE1027663B (OSRAM) |
| FR (1) | FR1171304A (OSRAM) |
| GB (1) | GB780301A (OSRAM) |
| NL (2) | NL83898C (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2986560A (en) * | 1952-11-19 | 1961-05-30 | Ciba Pharm Prod Inc | Process for the manufacture of 11-oxygenated steroids and intermediates therefor |
| US3142690A (en) * | 1956-01-25 | 1964-07-28 | Merck & Co Inc | 12alpha-halo-pregnenes |
| US2973377A (en) * | 1957-06-21 | 1961-02-28 | Olin Mathieson | 11beta, 12beta-epoxy and 12alpha-bromo steroids of the pregnane series and their method of preparation |
| US2944052A (en) * | 1957-06-26 | 1960-07-05 | Julian Lab Inc | Novel epoxy pregnanes |
| US2953583A (en) * | 1958-05-09 | 1960-09-20 | Olin Mathieson | 12alpha halo steroids of the androstane series |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2401775A (en) * | 1942-10-05 | 1946-06-11 | Reichstein Tadeus | Alpha-substituted side-chain ketones of the cyclopentanopolyhydrophenanthrene series and process of making the same |
| US2554882A (en) * | 1943-02-04 | 1951-05-29 | Reichstein Tadeus | 3-hydroxy-11-ketoetiocholanic acid and its esters |
| US2495735A (en) * | 1947-02-19 | 1950-01-31 | Research Corp | Process for preparing lower alkyl esters of 3-hydroxy-11-keto-12-bromonorcholanic acid |
| US2656348A (en) * | 1949-07-27 | 1953-10-20 | Ciba Pharm Prod Inc | Steroids having a 17-positioned semicyclic double bond |
| US2656365A (en) * | 1949-07-27 | 1953-10-20 | Ciba Pharm Prod Inc | Oxo-steroids and process of making same |
| US2590637A (en) * | 1949-08-26 | 1952-03-25 | Ciba Pharm Prod Inc | Direct halogenation of steroids with an unsaturated side chain in 17-position and the dehydrohalogenation of resultant products |
| US2655500A (en) * | 1951-10-15 | 1953-10-13 | Upjohn Co | Steroid ketone adducts |
| US2602769A (en) * | 1952-02-23 | 1952-07-08 | Upjohn Co | Oxygenation of steroids by mucorales fungi |
-
1952
- 1952-09-18 CH CH309920D patent/CH309920A/de unknown
-
1953
- 1953-08-11 US US373664A patent/US2776302A/en not_active Expired - Lifetime
- 1953-09-04 GB GB25355/53A patent/GB780301A/en not_active Expired
- 1953-09-11 FR FR1171304D patent/FR1171304A/fr not_active Expired
- 1953-09-15 DE DEC8185A patent/DE1027663B/de active Pending
- 1953-09-17 NL NL181423A patent/NL83898C/xx active
- 1953-09-17 NL NLAANVRAGE7606300,A patent/NL181423B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL83898C (OSRAM) | 1956-12-16 |
| DE1027663B (de) | 1958-04-10 |
| US2776302A (en) | 1957-01-01 |
| CH309920A (de) | 1955-09-30 |
| NL181423B (nl) | 1956-08-15 |
| FR1171304A (fr) | 1959-01-23 |
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