IT1271004B - Processo per la preparazione del gestodene - Google Patents
Processo per la preparazione del gestodeneInfo
- Publication number
- IT1271004B IT1271004B ITMI941846A ITMI941846A IT1271004B IT 1271004 B IT1271004 B IT 1271004B IT MI941846 A ITMI941846 A IT MI941846A IT MI941846 A ITMI941846 A IT MI941846A IT 1271004 B IT1271004 B IT 1271004B
- Authority
- IT
- Italy
- Prior art keywords
- double bond
- gestodene
- ketone group
- group
- transposition
- Prior art date
Links
- SIGSPDASOTUPFS-XUDSTZEESA-N gestodene Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](C=C4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 SIGSPDASOTUPFS-XUDSTZEESA-N 0.000 title abstract 2
- 229960005352 gestodene Drugs 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 125000000468 ketone group Chemical group 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 125000004036 acetal group Chemical group 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 230000017105 transposition Effects 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000006664 bond formation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- HZBAVWLZSLOCFR-UHFFFAOYSA-N oxosilane Chemical compound [SiH2]=O HZBAVWLZSLOCFR-UHFFFAOYSA-N 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
-
- 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
- C07J1/0051—Estrane derivatives
- C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
- C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
-
- 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
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0096—Alkynyl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Silicon Compounds (AREA)
- Glass Compositions (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Procedimento per preparare Gestodene da (-)estra-1, 3, 5 (10), 8-tetraen-3 metossi-18metil-17 Bidrossi, comprendente le seguenti fasi:a) idrogenazione del doppio legame in 8 (L i in NH3 liquida in presenza di anilina);b) idrogenazione di un doppio legame dell'anello aromatico (Li in NH3 liquida in presenza di ter. butanolo);e) idrolisi del metossile in 3 con introduzione di gruppo chetonico e trasposizione di doppio legame da 5-10 a 4-5;d) conversione del gruppo chetonico in 3 in gruppo acetalico e trasposizione del doppio legame da 4-5 e 5-6 (o 5-10);e) ossidazione dell'ossidrile in 17 a gruppo chetonico;f) formazione di doppio legame in 15-16 mediante ossidazione con Pd (11) acetato previa trasformazione in sililenoletere;g) etinilazione in posizione 17 con Li acetiluro;h) idrolisi del gruppo acetalico di posizione 3.
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI941846A IT1271004B (it) | 1994-09-09 | 1994-09-09 | Processo per la preparazione del gestodene |
ES95112768T ES2126819T3 (es) | 1994-09-09 | 1995-08-14 | Procedimiento para la preparacion de gestodeno. |
DK95112768T DK0700926T3 (da) | 1994-09-09 | 1995-08-14 | Fremgangsmåde til fremstilling af Gestodene |
AT95112768T ATE172981T1 (de) | 1994-09-09 | 1995-08-14 | Verfahren zur herstellung von gestoden |
DE69505761T DE69505761T2 (de) | 1994-09-09 | 1995-08-14 | Verfahren zur Herstellung von Gestoden |
EP95112768A EP0700926B1 (en) | 1994-09-09 | 1995-08-14 | Process for the preparation of gestodene |
US08/515,822 US5719300A (en) | 1994-09-09 | 1995-08-16 | Process for the preparation of gestodene |
CA002157076A CA2157076A1 (en) | 1994-09-09 | 1995-08-28 | Process for the preparation of gestodene |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI941846A IT1271004B (it) | 1994-09-09 | 1994-09-09 | Processo per la preparazione del gestodene |
Publications (3)
Publication Number | Publication Date |
---|---|
ITMI941846A0 ITMI941846A0 (it) | 1994-09-09 |
ITMI941846A1 ITMI941846A1 (it) | 1996-03-09 |
IT1271004B true IT1271004B (it) | 1997-05-26 |
Family
ID=11369533
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ITMI941846A IT1271004B (it) | 1994-09-09 | 1994-09-09 | Processo per la preparazione del gestodene |
Country Status (8)
Country | Link |
---|---|
US (1) | US5719300A (it) |
EP (1) | EP0700926B1 (it) |
AT (1) | ATE172981T1 (it) |
CA (1) | CA2157076A1 (it) |
DE (1) | DE69505761T2 (it) |
DK (1) | DK0700926T3 (it) |
ES (1) | ES2126819T3 (it) |
IT (1) | IT1271004B (it) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ITMI20040443A1 (it) * | 2004-03-08 | 2004-06-08 | Poli Ind Chimica Spa | Prpcesso per la preparazione di ..15-16-17-cheto-steroidi e loro uso nella sintesi di composti farmacologicamente attivi |
EP2354150A1 (en) | 2010-02-09 | 2011-08-10 | Laboratoire Theramex | Process for the preparation of gestodene |
CN107955053B (zh) * | 2017-12-11 | 2019-10-29 | 江西宇能制药有限公司 | 一种左炔诺孕酮中间体乙基锂氨物的制备方法 |
CN115850359A (zh) * | 2022-12-14 | 2023-03-28 | 梯尔希(南京)药物研发有限公司 | 一种孕二烯酮杂质i的制备方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3704253A (en) * | 1970-09-23 | 1972-11-28 | American Home Prod | 13 - polycarbonalkyl - 16 - methylgona-1,3,5(10)-trienes and 13-polycarbonalkyl-16-methylgon - 4 - en-3-ones and intermediates for their production |
US3876670A (en) * | 1973-02-05 | 1975-04-08 | Sandoz Ag | 11,11-dimethyl-substituted steroids |
US4081537A (en) | 1975-10-10 | 1978-03-28 | Schering Aktiengesellschaft | Δ15 -Steroids and pharmaceutical compositions thereof |
CN1008820B (zh) * | 1985-05-10 | 1990-07-18 | 施林工业产权保护股份公司 | 17α-乙炔基-17β-羟基-18-甲基-4,15-雌甾二烯-3-酮的制备方法 |
DE3710728A1 (de) | 1987-03-31 | 1988-10-13 | Schering Ag | Verfahren zur herstellung von 17(alpha)-ethinyl-17ss-hydroxy-18-methyl-4,15-estradien-3-on und die neuen zwischenprodukte fuer dieses verfahren |
DE4232521A1 (de) * | 1992-09-22 | 1994-03-24 | Schering Ag | Gestagen wirksame 4,5;11,12-Estradiene, Verfahren zu ihrer Herstellung, diese Estradiene enthaltende Arzneimittel sowie deren Verwendung zur Herstellung von Arzneimitteln |
-
1994
- 1994-09-09 IT ITMI941846A patent/IT1271004B/it active IP Right Grant
-
1995
- 1995-08-14 EP EP95112768A patent/EP0700926B1/en not_active Expired - Lifetime
- 1995-08-14 AT AT95112768T patent/ATE172981T1/de active
- 1995-08-14 ES ES95112768T patent/ES2126819T3/es not_active Expired - Lifetime
- 1995-08-14 DK DK95112768T patent/DK0700926T3/da active
- 1995-08-14 DE DE69505761T patent/DE69505761T2/de not_active Expired - Lifetime
- 1995-08-16 US US08/515,822 patent/US5719300A/en not_active Expired - Lifetime
- 1995-08-28 CA CA002157076A patent/CA2157076A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
DK0700926T3 (da) | 1999-07-19 |
DE69505761T2 (de) | 1999-06-24 |
ITMI941846A0 (it) | 1994-09-09 |
ES2126819T3 (es) | 1999-04-01 |
ITMI941846A1 (it) | 1996-03-09 |
EP0700926A1 (en) | 1996-03-13 |
ATE172981T1 (de) | 1998-11-15 |
CA2157076A1 (en) | 1996-03-10 |
EP0700926B1 (en) | 1998-11-04 |
US5719300A (en) | 1998-02-17 |
DE69505761D1 (de) | 1998-12-10 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
0001 | Granted | ||
TA | Fee payment date (situation as of event date), data collected since 19931001 |
Effective date: 19970929 |