GB780970A - Manufacture of 17--a-hydroxysteroids of the pregnane, allo-pregnane and pregnene series - Google Patents

Info

Publication number

GB780970A

GB780970A GB33073/53A GB3307353A GB780970A GB 780970 A GB780970 A GB 780970A GB 33073/53 A GB33073/53 A GB 33073/53A GB 3307353 A GB3307353 A GB 3307353A GB 780970 A GB780970 A GB 780970A

Authority

GB

United Kingdom

Prior art keywords

acetylamine

ketimine

pregnene

acetate

acid

Prior art date

1952-11-28

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

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• 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 title abstract 4
• 238000004519 manufacturing process Methods 0.000 title abstract 3
• 150000003130 pregnenes Chemical class 0.000 title abstract 2
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
• AHXYRYGQJLWGDG-LEKSSAKUSA-N 1-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 AHXYRYGQJLWGDG-LEKSSAKUSA-N 0.000 abstract 2
• ABVDSZAHODANPH-UQVNRYHBSA-N 2-[(8R,9S,10R,13S,14S)-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ylidene]ethanol Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=CCO)[C@@H]4[C@@H]3CC=C21 ABVDSZAHODANPH-UQVNRYHBSA-N 0.000 abstract 2
• ZSBDPRIWBYHIAF-UHFFFAOYSA-N N-acetyl-acetamide Natural products CC(=O)NC(C)=O ZSBDPRIWBYHIAF-UHFFFAOYSA-N 0.000 abstract 2
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 2
• 150000001875 compounds Chemical class 0.000 abstract 2
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
• PISUMXDGHKCWMR-GCYBHIIASA-N (8S,9S,10S,13R,14S,17R)-17-ethenyl-10,13-dimethyl-1,2,5,6,7,8,9,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,4,11-trione Chemical compound O=C1C(C2CC[C@H]3[C@@H]4CC[C@H](C=C)[C@]4(CC([C@@H]3[C@]2(CC1)C)=O)C)=O PISUMXDGHKCWMR-GCYBHIIASA-N 0.000 abstract 1
• AFUSHINCGQHXCX-AYKOVBTJSA-N (8S,9S,10S,13R,14S,17R)-17-ethenyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,11-diol Chemical compound OC1CC2CC[C@H]3[C@@H]4CC[C@H](C=C)[C@]4(CC([C@@H]3[C@]2(CC1)C)O)C AFUSHINCGQHXCX-AYKOVBTJSA-N 0.000 abstract 1
• ADVUWGLLXBPKHO-UQVNRYHBSA-N (8s,9s,10r,13s,14s)-17-ethylidene-10,13-dimethyl-1,2,3,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene Chemical compound C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC(=CC)[C@@]1(C)CC2 ADVUWGLLXBPKHO-UQVNRYHBSA-N 0.000 abstract 1
• DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 abstract 1
• GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 abstract 1
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 abstract 1
• YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 abstract 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
• DZMCNCYKOPTGNH-ZGWNGCAPSA-N C(C)(=O)N.C(C=C1CC[C@H]2[C@@H]3CC=C4CCCC[C@]4(C)[C@H]3CC[C@]12C)O Chemical compound C(C)(=O)N.C(C=C1CC[C@H]2[C@@H]3CC=C4CCCC[C@]4(C)[C@H]3CC[C@]12C)O DZMCNCYKOPTGNH-ZGWNGCAPSA-N 0.000 abstract 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
• HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 abstract 1
• AURFZBICLPNKBZ-UHFFFAOYSA-N Pregnanolone Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(=O)C)C1(C)CC2 AURFZBICLPNKBZ-UHFFFAOYSA-N 0.000 abstract 1
• VYXWTULYGXNMQU-LGMMMWRQSA-N [(8R,9S,10S,13R,14S,17R)-17-ethenyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] formate Chemical compound C(=O)OC1CC2CC[C@H]3[C@@H]4CC[C@H](C=C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C VYXWTULYGXNMQU-LGMMMWRQSA-N 0.000 abstract 1
• OWTSZVDOCQXOMW-RBEMGPCOSA-N [(8R,9S,10S,13R,14S,17S)-17-ethyl-10,13-dimethyl-15-oxo-1,2,3,4,5,6,7,8,9,11,12,14,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C(C)(=O)OC1CC2CC[C@@H]3[C@H](CC[C@@]4([C@H](CC([C@H]43)=O)CC)C)[C@]2(CC1)C OWTSZVDOCQXOMW-RBEMGPCOSA-N 0.000 abstract 1
• YZRJZHXWELDLDS-YXQMBUMISA-N [(8S,9S,10S,13R,14S,17R)-17-ethenyl-10,13-dimethyl-1-oxo-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C(C)(=O)OC1CC2CC[C@H]3[C@@H]4CC[C@H](C=C)[C@]4(CC[C@@H]3[C@]2(C(C1)=O)C)C YZRJZHXWELDLDS-YXQMBUMISA-N 0.000 abstract 1
• 239000002253 acid Substances 0.000 abstract 1
• ZJRXSAYFZMGQFP-UHFFFAOYSA-N barium peroxide Chemical compound [Ba+2].[O-][O-] ZJRXSAYFZMGQFP-UHFFFAOYSA-N 0.000 abstract 1
• CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 abstract 1
• ADKBGLXGTKOWIU-UHFFFAOYSA-N butanediperoxoic acid Chemical compound OOC(=O)CCC(=O)OO ADKBGLXGTKOWIU-UHFFFAOYSA-N 0.000 abstract 1
• 239000003795 chemical substances by application Substances 0.000 abstract 1
• 150000001805 chlorine compounds Chemical class 0.000 abstract 1
• CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 abstract 1
• 230000007062 hydrolysis Effects 0.000 abstract 1
• 238000006460 hydrolysis reaction Methods 0.000 abstract 1
• 150000004658 ketimines Chemical class 0.000 abstract 1
• 238000000034 method Methods 0.000 abstract 1
• 150000007524 organic acids Chemical class 0.000 abstract 1
• 235000005985 organic acids Nutrition 0.000 abstract 1
• 150000004967 organic peroxy acids Chemical class 0.000 abstract 1
• 230000003647 oxidation Effects 0.000 abstract 1
• 238000007254 oxidation reaction Methods 0.000 abstract 1
• WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 abstract 1
• PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 abstract 1
• 239000007858 starting material Substances 0.000 abstract 1