DE69723846T2 - Verfahren zur Herstellung von Sildenafil - Google Patents

Verfahren zur Herstellung von Sildenafil Download PDF

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Publication number
DE69723846T2
DE69723846T2 DE69723846T DE69723846T DE69723846T2 DE 69723846 T2 DE69723846 T2 DE 69723846T2 DE 69723846 T DE69723846 T DE 69723846T DE 69723846 T DE69723846 T DE 69723846T DE 69723846 T2 DE69723846 T2 DE 69723846T2
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DE
Germany
Prior art keywords
acid
chloride
solvent
compound
formula
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 - Lifetime
Application number
DE69723846T
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German (de)
English (en)
Other versions
DE69723846D1 (de
Inventor
Peter James Sandwich Dunn
Albert Shaw Sandwich Wood
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Ireland Pharmaceuticals
Original Assignee
Pfizer Ltd
Pfizer Research and Development Co NV SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10795332&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DE69723846(T2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Pfizer Ltd, Pfizer Research and Development Co NV SA filed Critical Pfizer Ltd
Application granted granted Critical
Publication of DE69723846D1 publication Critical patent/DE69723846D1/de
Publication of DE69723846T2 publication Critical patent/DE69723846T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26Sulfur atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/02Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10Drugs for genital or sexual disorders; Contraceptives for impotence
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D241/00Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Reproductive Health (AREA)
  • Endocrinology (AREA)
  • Urology & Nephrology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Steroid Compounds (AREA)
DE69723846T 1996-06-14 1997-06-04 Verfahren zur Herstellung von Sildenafil Expired - Lifetime DE69723846T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9612514.1A GB9612514D0 (en) 1996-06-14 1996-06-14 Novel process
GB9612514 1996-06-14

Publications (2)

Publication Number Publication Date
DE69723846D1 DE69723846D1 (de) 2003-09-04
DE69723846T2 true DE69723846T2 (de) 2004-03-04

Family

ID=10795332

Family Applications (2)

Application Number Title Priority Date Filing Date
DE69723846T Expired - Lifetime DE69723846T2 (de) 1996-06-14 1997-06-04 Verfahren zur Herstellung von Sildenafil
DE69700321T Expired - Lifetime DE69700321T2 (de) 1996-06-14 1997-06-04 Verfahren zur Herstellung Sildenafil

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE69700321T Expired - Lifetime DE69700321T2 (de) 1996-06-14 1997-06-04 Verfahren zur Herstellung Sildenafil

Country Status (48)

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SI1371647T1 (en) 1998-04-20 2005-10-31 Pfizer Inc. Pyridine-3-carboxylic acid derivatives and their use as intermediates
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GB9822238D0 (en) * 1998-10-12 1998-12-09 Pfizer Ltd Process for preparation of pyrazolo[4,3-D]pyrimidin-7-ones and intermediates thereof
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CN1094492C (zh) * 1999-06-21 2002-11-20 杭州神鹰医药化工有限公司 西地那非的制备方法
CN1077108C (zh) * 1999-07-13 2002-01-02 成都地奥制药集团有限公司 用于制备药物昔多芬的前体化合物
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CN1127506C (zh) * 2001-06-29 2003-11-12 刘宝顺 一种治疗阳痿的新化合物
JP4450365B2 (ja) * 2001-08-28 2010-04-14 シェーリング コーポレイション 多環式グアニンホスホジエステラーゼv阻害剤
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CN100374441C (zh) 2003-06-06 2008-03-12 天津倍方科技发展有限公司 二氢吡咯[2,3-d]嘧啶-4-酮衍生物,其制备方法及其制药用途
CN100360531C (zh) * 2003-12-18 2008-01-09 中国人民解放军军事医学科学院放射与辐射医学研究所 用于预防或治疗阳萎和性冷淡的新吡唑并嘧啶类化合物
EP1779852A3 (en) * 2004-01-05 2007-05-09 Teva Pharmaceutical Industries Ltd. Processes for the production of sildenafil base and citrate salt
PL1633364T3 (pl) 2004-01-05 2008-07-31 Teva Pharma Sposób wytwarzania zasady sildenafilu i cytrynianu sildenafilu
DE102005009240A1 (de) 2005-03-01 2006-09-07 Bayer Healthcare Ag Arzneiformen mit verbesserten pharmakokinetischen Eigenschaften
CN101563348B (zh) 2006-12-21 2011-08-24 上海特化医药科技有限公司 西地那非的制备方法及其中间体
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WO2010067140A1 (es) 2008-12-12 2010-06-17 Siegfried Rhein S.A. De C.V. Composicion de liberacion pulsatil de sildenafil y proceso para prepararla
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CN102993205B (zh) * 2012-12-27 2015-04-15 华润赛科药业有限责任公司 一种高收率制备高纯度西地那非游离碱的纯化方法
CN103044330B (zh) * 2013-01-14 2018-11-13 常州亚邦制药有限公司 西地那非中间体4-氨基-1-甲基-3-正丙基吡唑-5-甲酰胺的绿色合成新工艺
CN105085526B (zh) * 2014-05-15 2017-08-01 重庆圣华曦药业股份有限公司 一种改进的西地那非制备方法
CN105753870B (zh) * 2016-04-01 2018-05-22 重庆康刻尔制药有限公司 一种西地那非杂质f及其制备方法和应用
WO2017168174A1 (en) 2016-04-02 2017-10-05 N4 Pharma Uk Limited New pharmaceutical forms of sildenafil
CN105837578A (zh) * 2016-04-05 2016-08-10 重庆康刻尔制药有限公司 一种西地那非杂质d的合成方法
EP3522920A2 (en) 2016-10-10 2019-08-14 Transgene SA Immunotherapeutic product and mdsc modulator combination therapy
CN113493459B (zh) * 2020-04-07 2022-12-13 广州白云山医药集团股份有限公司白云山制药总厂 Pde5抑制剂化合物及其制备方法和应用
CN112961160A (zh) * 2021-03-05 2021-06-15 遂成药业股份有限公司 一种西地那非的改良合成工艺
CN113754612B (zh) * 2021-10-26 2023-09-26 山东安舜制药有限公司 一种西地那非中间体的制备方法

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Publication number Publication date
AU2487897A (en) 1997-12-18
TR199700470A2 (xx) 1998-01-21
EP0812845A1 (en) 1997-12-17
SK283894B6 (sk) 2004-04-06
UY24585A1 (es) 1997-12-02
EP0916675A2 (en) 1999-05-19
ES2201397T3 (es) 2004-03-16
IS4503A (is) 1997-12-15
ES2134051T3 (es) 1999-09-16
IN187319B (US08080257-20111220-C00005.png) 2002-03-23
NO304551B1 (no) 1999-01-11
AU697684B2 (en) 1998-10-15
JP3058863B2 (ja) 2000-07-04
DK0916675T3 (da) 2003-10-27
HU9701048D0 (en) 1997-08-28
CO4780028A1 (es) 1999-05-26
MA24205A1 (fr) 1997-12-31
IN187350B (US08080257-20111220-C00005.png) 2002-03-30
US6066735A (en) 2000-05-23
EG24123A (en) 2008-07-06
HRP970326A2 (en) 1998-06-30
HRP970326B1 (en) 2000-10-31
NO972481D0 (no) 1997-05-30
HK1033459A1 (en) 2001-08-31
SA97180124B1 (ar) 2006-02-08
JPH1081688A (ja) 1998-03-31
EA199700061A1 (ru) 1997-12-30
ATE246194T1 (de) 2003-08-15
DE69700321T2 (de) 1999-11-04
NZ328084A (en) 1998-08-26
JP2866841B2 (ja) 1999-03-08
SK283896B6 (sk) 2004-04-06
CZ181197A3 (cs) 1998-03-18
SI0812845T1 (en) 1999-12-31
IL121000A (en) 2000-02-29
AR003401A1 (es) 1998-08-05
GB9612514D0 (en) 1996-08-14
MX9704433A (es) 1998-11-30
HN1997000072A (es) 1997-12-26
IS1922B (is) 2004-03-15
SG50024A1 (en) 1998-06-15
YU25497A (sh) 1998-12-23
AP717A (en) 1999-01-04
ID18745A (id) 1998-05-07
RS49924B (sr) 2008-09-29
DE69700321D1 (de) 1999-08-19
GR3031087T3 (en) 1999-12-31
SK283893B6 (sk) 2004-04-06
PL320555A1 (en) 1997-12-22
NO985064L (no) 1997-12-15
IS6634A (is) 2002-11-25
IL125411A0 (en) 1999-03-12
BG101569A (en) 1998-01-30
RS20060484A (en) 2007-04-10
KR980002051A (ko) 1998-03-30
BR9703580A (pt) 1998-11-10
CN1106399C (zh) 2003-04-23
AP9701009A0 (en) 1997-07-31
SK283895B6 (sk) 2004-04-06
CA2207694C (en) 1999-11-23
NO306115B1 (no) 1999-09-20
SA97180124A (ar) 2005-12-03
DK0812845T3 (da) 1999-11-29
PL189333B1 (pl) 2005-07-29
DZ2247A1 (fr) 2002-12-18
NO985064D0 (no) 1998-10-30
ZA975259B (en) 1997-12-15
CZ290942B6 (cs) 2002-11-13
PE20011303A1 (es) 2001-12-25
CN1149206C (zh) 2004-05-12
PE1299A1 (es) 1999-01-13
CN1168376A (zh) 1997-12-24
SI0916675T1 (en) 2003-12-31
HU224497B1 (hu) 2005-10-28
PT916675E (pt) 2003-11-28
ATE182150T1 (de) 1999-07-15
RS49653B (sr) 2007-09-21
SK283897B6 (sk) 2004-04-06
CA2207694A1 (en) 1997-12-14
DE69723846D1 (de) 2003-09-04
KR100207352B1 (en) 1999-07-15
IL125411A (en) 2000-02-29
NO972481L (no) 1997-12-15
EA000102B1 (ru) 1998-08-27
EP0812845B1 (en) 1999-07-14
UY24612A1 (es) 2000-09-29
HUP9701048A3 (en) 2000-10-30
EP0916675A3 (en) 1999-07-14
IS1923B (is) 2004-03-15
BG62554B1 (bg) 2000-02-29
US5955611A (en) 1999-09-21
SK74397A3 (en) 1998-06-03
IN187318B (US08080257-20111220-C00005.png) 2002-03-23
UA27085C2 (uk) 2000-02-28
HUP9701048A2 (hu) 1998-12-28
EP0916675B1 (en) 2003-07-30
IN187317B (US08080257-20111220-C00005.png) 2002-03-23
IN187320B (US08080257-20111220-C00005.png) 2002-03-23
OA10426A (en) 2001-12-07
IL121000A0 (en) 1997-11-20
CN1282740A (zh) 2001-02-07
TNSN97102A1 (fr) 2005-03-15
JPH11171879A (ja) 1999-06-29

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