AU2000225442A1 - Preparation of sulfonamides - Google Patents

Preparation of sulfonamides

Info

Publication number
AU2000225442A1
AU2000225442A1 AU2000225442A AU2544200A AU2000225442A1 AU 2000225442 A1 AU2000225442 A1 AU 2000225442A1 AU 2000225442 A AU2000225442 A AU 2000225442A AU 2544200 A AU2544200 A AU 2544200A AU 2000225442 A1 AU2000225442 A1 AU 2000225442A1
Authority
AU
Australia
Prior art keywords
lower alkyl
hydrogen
hydroxy
alkoxy
alkyl
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.)
Abandoned
Application number
AU2000225442A
Inventor
Bradley S. Dehoff
Peter J. Harrington
Hiralal N. Khatri
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of AU2000225442A1 publication Critical patent/AU2000225442A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/69—Benzenesulfonamido-pyrimidines
    • 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

Abstract

The present invention provides a process for preparing 1, 2-diheteroethylene sulfonamide of the formula (i) by reacting a pyrimidine monohalide of the formula (ii) with a mono-protected 1, 2-diheteroethylene anion of the formula M1XCH2CH2YR5 and removing the protecting group, wherein R1 is hydrogen, lower alkyl, lower alkoxy, lower alkylthio, halogen or trifluoromethyl; R2 is hydrogen, halogen, lower alkoxy, trifluoromethyl or OCH2COORa; and R3 is hydrogen, halogen, lower alkyl, lower alkylthio, trifluoromethyl, cycloalkyl, lower alkoxy, or trifluoromethoxy; or R2 and R3 together can be butadienyl, methylenedioxy, ethylenedioxy or isopropylidenedioxy; R4 is hydrogen, lower alkyl, cycloalkyl, trifluoromethyl, lower alkoxy, lower alkylthio, lower alkylthio-lower alkyl, hydroxy-lower alkyl, hydroxy-lower alkoxy, lower alkoxy-lower alkyl, hydroxy-lower alkoxy-lower alkyl, hydroxy-lower alkoxy-lower alkoxy, lower alkylsulfinyl, lower alkylsulfonyl, 2-methoxy-3-hydroxypropoxy, 2-hydroxy-3-phenylpropyl, amino-lower alkyl, lower alkylamino-lower alkyl, di-lower alkylamino-lower alkyl, amino, lower alkylamino, di-lower alkylamino, arylamino, aryl, arylthio, aryloxy, aryl-lower alkyl or heterocyclyl; R5 is a protecting group; R6, R7, R8 and R9 are independently hydrogen, halogen, lower alkyl, trifluoromethyl, lower alkoxy, lower alkylthio, hydroxy, hydroxymethyl, cyano, carboxyl, formyl, methylsulfinyl, methylsulfonyl, methylsulfonyloxy or lower alkyloxy-carbonyloxy; or R7 together with R6 or R8 can be butadienyl, methylenedioxy, ethylenedioxy or isopropylidenedioxy; Z is O, S, ethylene, vinylene, C(=O), OCHR10, or SCHR10; R10 is hydrogen or lower alkyl; X and Y are independently O, S, or NH; M is hydrogen, an alkaline metal or an alkaline earth metal; M1 is an alkaline metal or an alkaline earth metal; and W is a halide.
AU2000225442A 2000-01-25 2000-01-25 Preparation of sulfonamides Abandoned AU2000225442A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2000/000556 WO2001055120A1 (en) 2000-01-25 2000-01-25 Preparation of sulfonamides

Publications (1)

Publication Number Publication Date
AU2000225442A1 true AU2000225442A1 (en) 2001-08-07

Family

ID=8163805

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2000225442A Abandoned AU2000225442A1 (en) 2000-01-25 2000-01-25 Preparation of sulfonamides

Country Status (13)

Country Link
EP (1) EP1254121B1 (en)
JP (1) JP3751882B2 (en)
KR (1) KR100495550B1 (en)
CN (1) CN1178921C (en)
AT (1) ATE316963T1 (en)
AU (1) AU2000225442A1 (en)
CA (1) CA2397258C (en)
DE (1) DE60025803T2 (en)
DK (1) DK1254121T3 (en)
ES (1) ES2255973T3 (en)
MX (1) MXPA02007192A (en)
PT (1) PT1254121E (en)
WO (1) WO2001055120A1 (en)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8288401B2 (en) * 2007-05-08 2012-10-16 Generics [Uk] Limited Polymorphic forms
EP2170841A1 (en) 2007-06-29 2010-04-07 Merck Generics (UK) Limited Process for introduction of hydroxyethoxy side chain in bosentan
CA2703230A1 (en) * 2007-10-24 2009-04-30 Generics [Uk] Limited Novel crystalline forms
CA2711043A1 (en) * 2008-01-01 2009-07-09 Cipla Limited Method of synthesis of bosentan, its polymorphic forms and its salts
EP2240469A2 (en) 2008-01-24 2010-10-20 Actavis Group PTC EHF Substantially pure and a stable crystalline form of bosentan
US8785461B2 (en) * 2008-02-08 2014-07-22 Generics [Uk] Limited Process for preparing bosentan
CN101279948B (en) * 2008-03-14 2010-08-11 苏州博鸿化工技术有限公司 Synthetic method of 4,6- dichloro-5-(2-methoxyphenoxy)-2,2'-dipyridine
WO2010015623A1 (en) * 2008-08-05 2010-02-11 Farmaprojects, S. A. Process for the preparation of endothelin receptor antagonists
US20110263623A1 (en) 2008-08-12 2011-10-27 Cadila Healthcare Limited Process for preparation of bosentan
EP2350028A1 (en) 2008-11-03 2011-08-03 Generics [UK] Limited Hplc method for the analysis of bosentan and related substances and use of these substances as reference standards and markers
IT1393136B1 (en) 2009-03-11 2012-04-11 Sifa Vitor S R L PROCEDURE FOR THE PREPARATION OF BOSENTAN
JP2012523444A (en) * 2009-04-13 2012-10-04 サンド・アクチエンゲゼルシヤフト Method for preparing an endothelial receptor antagonist (bosentan)
EP2368884A1 (en) 2010-03-25 2011-09-28 Laboratorios Lesvi, S.L. Process for the preparation of bosentan
PT2621909T (en) 2010-10-01 2019-03-29 Zach System Spa Process for preparing bosentan monohydrate and its intermediates
EP2848245A4 (en) * 2012-05-11 2016-01-27 Hanall Biopharma Co Ltd Bosentan controlled release oral preparation
KR102004422B1 (en) * 2012-12-20 2019-07-26 제일약품주식회사 A preparation method of bosentan monohydrate, novel intermediate useful for the preparation of bosentan monohydrate, and the preparation method thereof
AR095727A1 (en) * 2013-03-27 2015-11-04 Actelion Pharmaceuticals Ltd PREPARATION OF PYRIMIDINE INTERMEDIARIES
CN114907275A (en) * 2022-04-29 2022-08-16 武汉工程大学 Preparation method of bosentan

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2086544C1 (en) * 1991-06-13 1997-08-10 Хоффманн-Ля Рош АГ Benzenesulfonamide derivatives of pyrimidine or their salts, pharmaceutical composition for treatment of diseases associated with endothelin activity
TW287160B (en) * 1992-12-10 1996-10-01 Hoffmann La Roche
ATE238285T1 (en) * 1994-12-28 2003-05-15 Kowa Co PYRIMIDINE DERIVATIVES
US5739333A (en) * 1995-05-16 1998-04-14 Tanabe Seiyaku Co., Ltd. Sulfonamide derivative and process for preparing the same
EP0852226B1 (en) * 1995-09-06 2003-11-19 Kowa Co. Ltd. Pyrimidine derivatives

Also Published As

Publication number Publication date
DE60025803D1 (en) 2006-04-13
WO2001055120A1 (en) 2001-08-02
MXPA02007192A (en) 2002-12-09
CA2397258C (en) 2007-07-03
PT1254121E (en) 2006-06-30
CN1425007A (en) 2003-06-18
ES2255973T3 (en) 2006-07-16
EP1254121A1 (en) 2002-11-06
JP2003520857A (en) 2003-07-08
EP1254121B1 (en) 2006-02-01
DK1254121T3 (en) 2006-06-12
CN1178921C (en) 2004-12-08
KR100495550B1 (en) 2005-06-16
ATE316963T1 (en) 2006-02-15
JP3751882B2 (en) 2006-03-01
CA2397258A1 (en) 2001-08-02
DE60025803T2 (en) 2006-11-02
KR20020070511A (en) 2002-09-09

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