EA200900015A1 - ПРОМЫШЛЕННЫЙ СПОСОБ СИНТЕЗА 17α-АЦЕТОКСИ-11β-[4-(N,N-ДИМЕТИЛАМИНО)ФЕНИЛ]-19-НОРПРЕГНА-4,9-ДИЕН-3,20-ДИОНА И НОВЫЕ ПРОМЕЖУТОЧНЫЕ СОЕДИНЕНИЯ, ПОЛУЧЕННЫЕ В ДАННОМ СПОСОБЕ - Google Patents
ПРОМЫШЛЕННЫЙ СПОСОБ СИНТЕЗА 17α-АЦЕТОКСИ-11β-[4-(N,N-ДИМЕТИЛАМИНО)ФЕНИЛ]-19-НОРПРЕГНА-4,9-ДИЕН-3,20-ДИОНА И НОВЫЕ ПРОМЕЖУТОЧНЫЕ СОЕДИНЕНИЯ, ПОЛУЧЕННЫЕ В ДАННОМ СПОСОБЕInfo
- Publication number
- EA200900015A1 EA200900015A1 EA200900015A EA200900015A EA200900015A1 EA 200900015 A1 EA200900015 A1 EA 200900015A1 EA 200900015 A EA200900015 A EA 200900015A EA 200900015 A EA200900015 A EA 200900015A EA 200900015 A1 EA200900015 A1 EA 200900015A1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- formula
- ethylenedioxy
- reacted
- norpregn
- diene
- Prior art date
Links
- -1 N, N-DIMETHYLAMINO Chemical class 0.000 title abstract 9
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 9
- 238000000034 method Methods 0.000 abstract 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 abstract 2
- 241001135931 Anolis Species 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical compound ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- CIHXIRAAMAUYLZ-UHFFFAOYSA-N [K+].[K+].[C-]#[C-] Chemical compound [K+].[K+].[C-]#[C-] CIHXIRAAMAUYLZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 abstract 1
- OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 abstract 1
Classifications
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- 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
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/46—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of glucocorticosteroids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- 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
- C07J41/0077—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
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
Abstract
Настоящее изобретение относится к новому промышленному способу синтеза несольватированного 17α-ацетокси-11β-[4-(N,N-диметиламино)фенил]-19-норпрегна-4,9-диен-3,20-диона [CDB-2914] формулы (I), представляющего собой сильное антипрогестогенное и антиглюкокортикоидное средство. Настоящее изобретение также относится к соединениям формул (VII) и (VIII), использующихся в указанном способе в качестве промежуточных соединений. Способ по настоящему изобретению состоит в следующем: i) 3-(этилендиокси)эстра-5(10),9(11)-диен-17-он формулы (X) вводят в реакцию с ацетилидом калия, полученным in situ в сухом тетрагидрофуране известным способом, ii) полученный 3-этилендиокси)-17α-этинил-17β-гидрокси-эстра-5(10),9(11)-диен формулы (IX) вводят в реакцию с фенилсульфенилхлоридом в дихлорметане в присутствии триэтиламина и уксусной кислоты, iii) полученную смесь изомеров 3-(этилендиокси)-21-(фенилсульфинил)-19-норпрегна-5(10),9(11),17(20),20-тетраена формулы (VIII) вводят в реакцию сначала с метоксидом натрия в метаноле, затем с триметилфосфитом, iv) полученный 3-(этилендиокси)-17α-гидрокси-20-метокси-19-норпрегн-5(10),9(11),20-триен формулы (VII) вводят в реакцию с хлороводородом в метаноле, затем v) полученный 3-(этилендиокси)-17α-гидрокси-19-норпрегн-5(10),9(11)-диен-20-он формулы (VI) вводят в реакцию с этиленгликолем в дихлорметане в присутствии триметилортоформата и п-толуолсульфокислоты по известному способу, vi) полученный 3,3,20,20-бис(этилендиокси)-17α-гидрокси-19-норпрегн-5(10),9(11)-диен формулы (V) вводят в реакцию с пероксидом водорода в смеси пиридина и дихлорметана в присутствии гексахлорацетона по известному способу, vii) полученный 3,3,20,20-бис(этилендиокси)-17α-гидрокси-5,10-эпокси-19-норпрегн-9(11)-ен формулы (IV), содержащий смесь 5α,10α- и 5β,β-эпоксидов приблизительно 1:1, выделяют из раствора и вводят в реакцию с реактивом Гриньяра, полученным
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU0600491A HU227112B1 (hu) | 2006-06-14 | 2006-06-14 | Ipari eljárás 17-alfa-acetoxi-11-béta-[4-(N,N-dimetil-amino)-fenil]-19-norpregna-4,9-dién-3,20-dion elõállítására és új intermedierek az eljáráshoz |
PCT/HU2007/000045 WO2007144674A1 (en) | 2006-06-14 | 2007-05-18 | INDUSTRIAL PROCESS FOR THE SYNTHESIS OF 17α-ACETOXY-11β-[4-(N,N-DIMETHYL-AMINO)- PHENYL]-19-NORPREGNA-4,9-DIENE-3,20-DIONE AND NEW INTERMEDIATES OF THE PROCESS |
Publications (2)
Publication Number | Publication Date |
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EA200900015A1 true EA200900015A1 (ru) | 2009-04-28 |
EA015302B1 EA015302B1 (ru) | 2011-06-30 |
Family
ID=89986843
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EA200900015A EA015302B1 (ru) | 2006-06-14 | 2007-05-18 | ПРОМЫШЛЕННЫЙ СПОСОБ СИНТЕЗА 17α-АЦЕТОКСИ-11β-[4-(N,N-ДИМЕТИЛАМИНО)ФЕНИЛ]-19-НОРПРЕГНА-4,9-ДИЕН-3,20-ДИОНА И НОВЫЕ ПРОМЕЖУТОЧНЫЕ СОЕДИНЕНИЯ, ПОЛУЧЕННЫЕ В ДАННОМ СПОСОБЕ |
Country Status (22)
Country | Link |
---|---|
US (1) | US8110691B2 (ru) |
EP (1) | EP2027140B1 (ru) |
JP (1) | JP5274453B2 (ru) |
CN (1) | CN101466723B (ru) |
AR (1) | AR061052A1 (ru) |
AU (1) | AU2007258955B2 (ru) |
BR (1) | BRPI0713157A2 (ru) |
CA (1) | CA2653552C (ru) |
DK (1) | DK2027140T3 (ru) |
EA (1) | EA015302B1 (ru) |
ES (1) | ES2409841T3 (ru) |
HU (1) | HU227112B1 (ru) |
IL (1) | IL195253A (ru) |
MX (1) | MX2008015972A (ru) |
NO (1) | NO341620B1 (ru) |
PL (1) | PL2027140T3 (ru) |
PT (1) | PT2027140E (ru) |
RS (1) | RS52758B (ru) |
SI (1) | SI2027140T1 (ru) |
UA (1) | UA94269C2 (ru) |
WO (1) | WO2007144674A1 (ru) |
ZA (1) | ZA200809799B (ru) |
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CN102372760A (zh) * | 2010-08-12 | 2012-03-14 | 杭州容立医药科技有限公司 | 一种合成孕酮受体调节剂优力司特的合成方法 |
CN102477060B (zh) * | 2010-11-22 | 2014-08-13 | 华润紫竹药业有限公司 | 甾体化合物及其制备方法和用途 |
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 |
CN102295674B (zh) * | 2011-07-14 | 2013-04-10 | 四川大学 | 获得高纯度17α-乙酰氧基-11β-(4-N,N-二甲氨基苯基)-19-去甲孕甾-4,9-二烯-3,20-二酮的方法 |
CN102321141B (zh) * | 2011-07-22 | 2013-05-15 | 上海希迈医药科技有限公司 | 一种17α-乙酰氧基-11β-(4-N,N-二甲氨基苯基)-19-去甲孕甾-4,9-二烯-3,20-二酮的无定形物及其制备方法 |
CN102344478B (zh) * | 2011-07-22 | 2013-08-07 | 上海希迈医药科技有限公司 | 一种17α-乙酰氧基-11β-(4-N,N-二甲氨基苯基)-19-去甲孕甾-4,9-二烯-3,20-二酮的结晶物及其制备方法 |
CN103193850A (zh) * | 2012-01-04 | 2013-07-10 | 北京紫竹药业有限公司 | 甾体化合物的新晶型及其制备方法 |
CN106046099B (zh) * | 2012-01-19 | 2018-03-16 | 华润紫竹药业有限公司 | 甾体化合物及其制备方法和用途 |
CN104628806A (zh) * | 2012-01-19 | 2015-05-20 | 华润紫竹药业有限公司 | 甾体化合物及其制备方法和用途 |
CN103755765B (zh) * | 2012-04-17 | 2018-01-02 | 常州市第四制药厂有限公司 | 醋酸乌利司他的多晶型及其制备方法 |
CN102675395B (zh) * | 2012-04-17 | 2014-04-30 | 常州市第四制药厂有限公司 | 醋酸乌利司他的多晶型及其制备方法 |
CN102702296B (zh) * | 2012-06-19 | 2014-09-03 | 山东诚创医药技术开发有限公司 | 环-3,20-双(1,2-亚乙基缩醛)-17α-羟基-17β-乙酰基-雌甾-5(10),9(11)-二烯-3-酮的制备方法 |
JP6474722B2 (ja) | 2012-09-28 | 2019-02-27 | あすか製薬株式会社 | ウリプリスタール酢酸エステルの結晶多形 |
CA2885798A1 (en) | 2012-09-28 | 2014-04-03 | Aska Pharmaceutical Co., Ltd. | Crystalline polymorphic form of ulipristal acetate |
JP6200493B2 (ja) | 2012-09-28 | 2017-09-20 | あすか製薬株式会社 | 無定形ウリプリスタール酢酸エステル |
CN102875629B (zh) * | 2012-10-10 | 2014-11-19 | 苏州康润医药有限公司 | 醋酸乌利司他的合成方法 |
WO2014060888A1 (en) * | 2012-10-18 | 2014-04-24 | Lupin Limited | Novel process and intermediate for preparation of ulipristal |
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 |
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US6512130B1 (en) * | 2000-09-05 | 2003-01-28 | Council Of Scientific And Industrial Research | Mifepristone analogue, process for the preparation thereof and use thereof |
EP1613640A4 (en) | 2003-02-28 | 2010-05-19 | Us Gov Health & Human Serv | PROCESS FOR PREPARING 17 ALPHA-ACETOXY-11 BETA- (4-N, N-DIMETHYLAMINOPHENYL) -19-NORPREGNA-4,9-DIENE-3,20-DION, INTERMEDIATE PRODUCTS AND METHOD OF MANUFACTURING THESE INTERMEDIATE PRODUCTS |
FR2854403B1 (fr) * | 2003-04-29 | 2008-07-11 | Aventis Pharma Sa | Nouveau procede et intermediaires de preparation de composes 19-nor-steroides 17-halogenes |
HUP0301332A3 (en) * | 2003-05-14 | 2006-04-28 | Richter Gedeon Vegyeszet | New mono-and bismethylene steroid derivatives and process for their synthesis and pharmaceutical compositions containing them |
ITMI20042001A1 (it) * | 2004-10-21 | 2005-01-21 | Ind Chimica Srl | Processo per la preparazione di 21-idrossi steroidi con controllo della distribuzione epimerica nella posizione c-21 |
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Also Published As
Publication number | Publication date |
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US8110691B2 (en) | 2012-02-07 |
EP2027140A1 (en) | 2009-02-25 |
JP5274453B2 (ja) | 2013-08-28 |
DK2027140T3 (da) | 2013-06-03 |
AU2007258955B2 (en) | 2012-09-20 |
RS52758B (en) | 2013-08-30 |
HU0600491D0 (en) | 2006-08-28 |
ZA200809799B (en) | 2009-11-25 |
WO2007144674A1 (en) | 2007-12-21 |
IL195253A0 (en) | 2009-08-03 |
ES2409841T3 (es) | 2013-06-28 |
UA94269C2 (en) | 2011-04-26 |
CA2653552A1 (en) | 2007-12-21 |
CA2653552C (en) | 2013-04-23 |
NO341620B1 (no) | 2017-12-11 |
CN101466723A (zh) | 2009-06-24 |
HU227112B1 (hu) | 2010-07-28 |
AR061052A1 (es) | 2008-07-30 |
BRPI0713157A2 (pt) | 2012-04-03 |
US20090187032A1 (en) | 2009-07-23 |
PL2027140T3 (pl) | 2013-09-30 |
NO20090196L (no) | 2009-03-10 |
JP2009539964A (ja) | 2009-11-19 |
IL195253A (en) | 2011-11-30 |
EA015302B1 (ru) | 2011-06-30 |
PT2027140E (pt) | 2013-06-04 |
CN101466723B (zh) | 2011-11-02 |
HUP0600491A2 (en) | 2008-02-28 |
EP2027140B1 (en) | 2013-03-13 |
SI2027140T1 (sl) | 2013-07-31 |
MX2008015972A (es) | 2009-01-12 |
AU2007258955A1 (en) | 2007-12-21 |
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