BRPI0813654B8 - método industrial para a síntese de 17-acetóxi-11ß-[4-(dimetilamino)-fenil]-21-metóxi-19-norpregna-4,9-dieno-3,20-diona e os intermediários essenciais do processo - Google Patents
método industrial para a síntese de 17-acetóxi-11ß-[4-(dimetilamino)-fenil]-21-metóxi-19-norpregna-4,9-dieno-3,20-diona e os intermediários essenciais do processoInfo
- Publication number
- BRPI0813654B8 BRPI0813654B8 BRPI0813654A BRPI0813654A BRPI0813654B8 BR PI0813654 B8 BRPI0813654 B8 BR PI0813654B8 BR PI0813654 A BRPI0813654 A BR PI0813654A BR PI0813654 A BRPI0813654 A BR PI0813654A BR PI0813654 B8 BRPI0813654 B8 BR PI0813654B8
- Authority
- BR
- Brazil
- Prior art keywords
- formula
- oxy
- bis
- phenyl
- dimethylamino
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 4
- 239000000543 intermediate Substances 0.000 title abstract 3
- 238000003786 synthesis reaction Methods 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 238000004587 chromatography analysis Methods 0.000 abstract 2
- 238000011065 in-situ storage Methods 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005051 trimethylchlorosilane Substances 0.000 abstract 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 238000006859 Swern oxidation reaction Methods 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000003388 anti-hormonal effect Effects 0.000 abstract 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- OFDIPUNYMRLSER-UHFFFAOYSA-M magnesium;n,n-dimethylaniline;bromide Chemical compound [Mg+2].[Br-].CN(C)C1=CC=[C-]C=C1 OFDIPUNYMRLSER-UHFFFAOYSA-M 0.000 abstract 1
- -1 methoxy-methyl grignard reagent Chemical class 0.000 abstract 1
- 238000005667 methoxymethylation reaction Methods 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000006884 silylation reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- 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
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Reproductive Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Endocrinology (AREA)
- Animal Behavior & Ethology (AREA)
- Toxicology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
método industrial para a síntese de 17-acetóxi-11(beta)-[4-(dimetilamino)- fenil]-21-metóxi-19-norpregna-4,9-dieno-3,20-diona e os intermediários essenciais do processo a presente invenção refere-se a um processo para a síntese do 17-acetóxi-11-ss-[4-(dimetilamino)-denil]-21-metóxi-19-norpregna-4,9-dien-3,20-diona conhecido (posteriormente no cdb-4124) da fórmula (i) derivado do 3,3-[1,2-etandiil-bis(óxi)]-oestr-5(10),9(11)-dien-17-ona da fórmula (ii). o composto cdb-4124 pertence ao grupo dos anti-hormônios. o processo de acordo com a invenção é o seguinte: i) formação de um epóxido na ligação dupla na posição 5(10) de 3,3-[1,2-etandiil- bis(óxi)]-oestr-5(10),9(11)-dien-17-ona da fórmula (ii) com peróxido de hidrogênio formado in situ na posição 17 do 5,10a- epóxi-3,3-[1,2-etandiil-bis(óxi)]-5a-oestr9(11)-en-17-ona obtido da fórmula (iii); iii) siliação do grupo hidroxila na posição 17 do 5,10a-epóxi-3,3[1,2 etandiil-bis(óxi)]-17a-hidróxi-5a-oestr-9(11)-en-17ss-carbonitrilo formado da fórmula (iv) com trimetil clorossilano; iv) reação do 5,10a-epóxi-3,3-[1,2-etandiil-bis(óxi)]-17-[trimetil-silil-óxi]-5a-oestr-9(11)-en-17ss-carbolitrilo obtido da fórmula (v) com o agente de grignard brometo de magnésio 4-(dimetilamino)-fenil na presença de cuci (reação de teutsch); v) sililação do grupo hidroxila na posição 5 do i iss-[4-(dimetil-amino)-fenil] -3,-3 [1,2-etandiil-bis(óxi)] -5 -hidróxi- 17a- [trimetilsilil-(óxi)] -5 a-oestr-9-en-17ss-carbonitrilo formado da fórmula (vi) com trimetil clorossilano; vi) reação do obtido 1,2(alfa)-[4-(dimetilamino)-fenil]-3-3-[1,2-etandiil-bis(óxi)]-5,17a-bis-[trimetil-silil-(óxi)]-5a-oestr-9-en-17ss-carbonitrilo da fórmula (vii) com diisobutil alumínio hidreto e após adição of acid to a mistura da reação; vii) metóxi-metilation d obtido 1 1ss-[4-(dimetilamino)-fenil]-3,3-[1,2-etandiil-bis(óxi)]-5, 17a-bis-[trimetil-silil-(óxi)]-5a-oestr-9-en17ss-carbaldeído da fórmula (viii) com reagente de grignard metóxi-metil formado in situ, enquanto hidrolisa os grupos protetores de trimetilsilil; viii) oxidação do grupo hidroxil na posição 20 d obtido 17,20?-diidróxi-11ss-[4-(dimemilarnino)-fenil]-21-metóxi-19-norpregna-4,9-dien-3-ona da fórmula (ix) com diciclohexil carbodiimida na presença de dimetil sulfóxido e ácido orgânico forte (oxidação swern), e no dado caso, após purificação por cromatografia; ix) acetilação do grupo hidroxil na posição 17 do 11ss-[4-(dimetilamino)-fenil] -17-hidróxi-21-metóxi-19-norpregna-4,9-dien-3,20-diona obtido da fórmula (x) com anidreto acético na presença de ácido perclórico, e no dado caso, o 7-acetóxi-11-ss-[4-(dimetilamino)-fenil)]-21-metóxi-19-norpregna-4,9-dien-3,20-diona obtido da fórmula (i) é purificado por cromatografia. a invenção também refere aos novos intermediários da fórmula (vii) e (viii).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUP0700439 | 2007-06-27 | ||
| HU0700439A HU228636B1 (en) | 2007-06-27 | 2007-06-27 | Industrial method for the synthesis of 17-acetoxy-11betha-4[-(dimethylamino)-phenyl]-21-methoxy-19-norpregna-4,9-dien-3,20-dione and the key intermediates of the process |
| PCT/HU2008/000073 WO2009001148A2 (en) | 2007-06-27 | 2008-06-19 | INDUSTRIAL METHOD FOR THE SYNTHESIS OF 17-ACETOXY-11β-[4-(DIMETHYLAMINO)-PHENYL]-21-METHOXY-19-NORPREGNA-4,9-DIEN-3,20-DIONE AND THE KEY INTERMEDIATES OF THE PROCESS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| BRPI0813654A2 BRPI0813654A2 (pt) | 2014-12-30 |
| BRPI0813654B1 BRPI0813654B1 (pt) | 2021-05-04 |
| BRPI0813654B8 true BRPI0813654B8 (pt) | 2021-05-25 |
Family
ID=89987607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0813654A BRPI0813654B8 (pt) | 2007-06-27 | 2008-06-19 | método industrial para a síntese de 17-acetóxi-11ß-[4-(dimetilamino)-fenil]-21-metóxi-19-norpregna-4,9-dieno-3,20-diona e os intermediários essenciais do processo |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US8183402B2 (pt) |
| EP (1) | EP2160398B1 (pt) |
| JP (1) | JP5261481B2 (pt) |
| KR (1) | KR101535686B1 (pt) |
| CN (1) | CN101622268B (pt) |
| AR (1) | AR067189A1 (pt) |
| AT (1) | ATE528313T1 (pt) |
| AU (1) | AU2008269531B2 (pt) |
| BR (1) | BRPI0813654B8 (pt) |
| CA (1) | CA2677195C (pt) |
| CY (1) | CY1112529T1 (pt) |
| DK (1) | DK2160398T3 (pt) |
| EA (1) | EA015478B1 (pt) |
| ES (1) | ES2375320T3 (pt) |
| HR (1) | HRP20120008T1 (pt) |
| HU (1) | HU228636B1 (pt) |
| IL (1) | IL200124A (pt) |
| MX (1) | MX2009011861A (pt) |
| MY (1) | MY149296A (pt) |
| NZ (1) | NZ579029A (pt) |
| PL (1) | PL2160398T3 (pt) |
| PT (1) | PT2160398E (pt) |
| SI (1) | SI2160398T1 (pt) |
| TW (1) | TWI411616B (pt) |
| UA (1) | UA100241C2 (pt) |
| WO (1) | WO2009001148A2 (pt) |
| ZA (1) | ZA200907030B (pt) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0900171A2 (hu) * | 2009-03-20 | 2010-12-28 | Richter Gedeon Nyrt | 17-acetoxi-11ß-[4-(dimetil-amino)-fenil]-21-metoxi-19-norpregna-4,9-dién-3,20-dion új kristályos módosulata és eljárás elõállítására |
| HUP0900487A2 (hu) * | 2009-08-05 | 2011-03-28 | Richter Gedeon Nyrt | 17-acetoxi-11ß-[4-(dimetil-amino)-fenil]-21-metoxi-19-norpregna-4,9-dién-3,20-dion új kristályos polimorf módosulata és eljárás elõállítására |
| CN102516345B (zh) | 2011-11-01 | 2014-11-26 | 上海优拓医药科技有限公司 | 醋酸乌利司他及其关键中间体的制备方法 |
| CN102942612A (zh) * | 2012-10-30 | 2013-02-27 | 四川大学 | 一种合成醋酸乌利司他的新方法 |
| KR20160058722A (ko) * | 2013-03-15 | 2016-05-25 | 더 플로리다 스테이트 유니버시티 리서치 파운데이션, 인크 | ent-프로게스테론 및 그의 중간생성물의 합성 |
| HU230319B1 (hu) | 2013-10-01 | 2016-01-28 | Richter Gedeon Nyrt. | Ipari eljárás szteroid hatóanyagok előállítására |
| HU230397B1 (hu) | 2013-11-25 | 2016-04-28 | Richter Gedeon Nyrt. | Eljárás (11b,17a)-17-acetoxi-11-metil-19-norpregn-4-én-3,20-dion előállítására |
| CN103601785A (zh) * | 2013-11-25 | 2014-02-26 | 四川大学 | 一种醋酸优力斯特新的合成方法 |
| HU230381B1 (hu) * | 2014-02-17 | 2016-03-29 | Richter Gedeon Nyrt | Ipari eljárás szteroid intermedier előállítására |
| CN107200770B (zh) * | 2016-03-18 | 2019-11-01 | 华东师范大学 | 特拉司酮合成中环氧异构体的高效分离和循环利用方法 |
| CN109575098B (zh) * | 2019-01-18 | 2021-01-01 | 湖南成大生物科技有限公司 | 诺孕美特的合成方法 |
| CN115536529B (zh) * | 2022-09-26 | 2024-06-25 | 浦拉司科技（上海）有限责任公司 | 一种3,5-二（2-氰基-异丙基）-甲苯的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA8231B (en) * | 1981-01-09 | 1982-11-24 | Roussel Uclaf | New 11 -substituted steroid derivatives, their preparation, their use as medicaments, the compositions containing them and the new intermediates thus obtained |
| DE3722486A1 (de) * | 1987-07-03 | 1989-01-12 | Schering Ag | Neues epoxidierungs-reagenz und seine verwendung |
| US4954490A (en) * | 1988-06-23 | 1990-09-04 | Research Triangle Institute | 11 β-substituted progesterone analogs |
| US6900193B1 (en) | 1996-05-01 | 2005-05-31 | The United States Of America As Represented By The Department Of Health And Human Services | Structural modification of 19-norprogesterone I: 17-α-substituted-11-β-substituted-4-aryl and 21-substituted 19-norpregnadienedione as new antiprogestational agents |
| JP4260886B2 (ja) * | 1996-05-01 | 2009-04-30 | アメリカ合衆国 | 新規の抗プロゲステロンとしての２１―置換プロゲステロン誘導体 |
| EP1242444B1 (en) * | 1999-12-29 | 2005-07-20 | THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES | Process for preparing 17alpha-acetoxy-11beta- 4-n,n-(dimethylamino)phenyl]-21-methoxy-19-norpregna-4,9-diene-3,20-dione, intermediates useful in the process, and processes for preparing such intermediates |
| DK1265911T3 (da) | 2000-03-17 | 2008-09-29 | Us Gov Health & Human Serv | 17-alfa-substitueret-11-beta-substitueret-4-aryl og 21-substitueret 19-norpregnadiendion som antiprogestationelle midler |
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2007
- 2007-06-27 HU HU0700439A patent/HU228636B1/hu unknown
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2008
- 2008-06-19 UA UAA201000779A patent/UA100241C2/uk unknown
- 2008-06-19 KR KR1020097017565A patent/KR101535686B1/ko active IP Right Grant
- 2008-06-19 AU AU2008269531A patent/AU2008269531B2/en active Active
- 2008-06-19 SI SI200830476T patent/SI2160398T1/sl unknown
- 2008-06-19 CA CA2677195A patent/CA2677195C/en active Active
- 2008-06-19 MX MX2009011861A patent/MX2009011861A/es active IP Right Grant
- 2008-06-19 DK DK08762676.8T patent/DK2160398T3/da active
- 2008-06-19 AT AT08762676T patent/ATE528313T1/de active
- 2008-06-19 BR BRPI0813654A patent/BRPI0813654B8/pt active IP Right Grant
- 2008-06-19 CN CN2008800063272A patent/CN101622268B/zh active Active
- 2008-06-19 WO PCT/HU2008/000073 patent/WO2009001148A2/en active Application Filing
- 2008-06-19 PL PL08762676T patent/PL2160398T3/pl unknown
- 2008-06-19 NZ NZ579029A patent/NZ579029A/en unknown
- 2008-06-19 EP EP08762676A patent/EP2160398B1/en active Active
- 2008-06-19 EA EA201070061A patent/EA015478B1/ru unknown
- 2008-06-19 ES ES08762676T patent/ES2375320T3/es active Active
- 2008-06-19 JP JP2010514149A patent/JP5261481B2/ja active Active
- 2008-06-19 US US12/598,163 patent/US8183402B2/en active Active
- 2008-06-19 PT PT08762676T patent/PT2160398E/pt unknown
- 2008-06-19 MY MYPI20093980A patent/MY149296A/en unknown
- 2008-06-23 TW TW097123350A patent/TWI411616B/zh active
- 2008-06-26 AR ARP080102767A patent/AR067189A1/es active IP Right Grant
-
2009
- 2009-07-28 IL IL200124A patent/IL200124A/en active IP Right Grant
- 2009-10-08 ZA ZA200907030A patent/ZA200907030B/xx unknown
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2011
- 2011-12-14 CY CY20111101242T patent/CY1112529T1/el unknown
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2012
- 2012-01-03 HR HR20120008T patent/HRP20120008T1/hr unknown
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