KR960014122A - 2종 결정형의 테트라졸 유도체의 제조방법 및 그의 신규 결정형 - Google Patents

2종 결정형의 테트라졸 유도체의 제조방법 및 그의 신규 결정형 Download PDF

Info

Publication number
KR960014122A
KR960014122A KR1019950036285A KR19950036285A KR960014122A KR 960014122 A KR960014122 A KR 960014122A KR 1019950036285 A KR1019950036285 A KR 1019950036285A KR 19950036285 A KR19950036285 A KR 19950036285A KR 960014122 A KR960014122 A KR 960014122A
Authority
KR
South Korea
Prior art keywords
butyl
methyl
diazaspiro
biphenyl
tetrazol
Prior art date
Application number
KR1019950036285A
Other languages
English (en)
Other versions
KR100251222B1 (ko
Inventor
까롱 앙뜨완느
샹트리 도미니끄
블루미 꼴레뜨
Original Assignee
로날 샤삐라
사노피
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 로날 샤삐라, 사노피 filed Critical 로날 샤삐라
Publication of KR960014122A publication Critical patent/KR960014122A/ko
Application granted granted Critical
Publication of KR100251222B1 publication Critical patent/KR100251222B1/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic 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
    • C07D403/10—Heterocyclic 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 carbon chain containing aromatic 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
    • A61P9/12—Antihypertensives

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (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)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

본 발명은 해당 니트릴를 알칼라인 아지드 및 트리에틸아민 히드로클로리드로 처리하여, 2-n. 부틸-3-〔〔 2′-(테트라졸-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온을 수용액 내 그의 알칼라인염증 하나의 형태로 회수하고, 상기 알칼라인염을 중화시키고, 상기와 같이 침전된 2-n. 부틸-3-〔〔 2′-(테트라졸-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온을 10% 미만의 물을 함유하는 용매 또는 10%를 초과하는 물을함유하는 용매중 하나에서 결정화하여 2종의서로 다른 결정형을 수득하는 반응에 의하여 2-n. 부틸-3-〔〔 2′-(테트라졸-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온을제조하는 방법에 관한 것이다. 또한 본 발명은 2-n. 부틸-3-〔〔 2′-(테트라졸-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온의 신규 걸정형 및 그를 함유하는 약학적 조성물에 관한 것이다.

Description

2종 결정형의 테트라졸 유도체의 제조방법 및 그이 신규 결정형
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (8)

  1. 하기의 단계로 이루어지는 2-n. 부틸-3-〔〔 2′-(테트라졸-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온의 제조 방법 : (a) 불활성 극성 비양자성 용매 내에서 2-n. 부틸-3-〔〔 2′-(테트라졸-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온을 알칼라인 아지드 및 트리에틸아민 히드로클로리드로 처리한 후, 이렇게 수득된 2-n. 부틸-3-〔〔 2′-(테트라졸-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온을 수용액내에 그의 알칼라인염증 하나의 형태로 회수하고 (b) 이렇게 수득된 2-n. 부틸-3-〔〔 2′-(테트라졸-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온의 알칼라인 염을 수성 매질 내에서 pH가 4.7 내지 5.3d 될 때까지 중화시키고; (c) 이렇게 하여 침전된 생성물을 하기와 같이 결정화한다 : -약 10부피% 미만의 물을 함유하는 용매 내에서 표 II 에 나타낸 X-레이분말 회전 패턴을 가지는 A형의 2-n. 부틸-3-〔〔 2′-(테트라졸-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온을 분리하거나; -또는, 약 10부피%를 초과하는 물을 함유하는 수-혼합성 용매내에서 표 I에 나타낸 X-레이 분말 회전 패턴을 가지는 B형의 2-n. 부틸-3-〔〔 2′-(테트라졸-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온을 분리한다.
  2. 제1항에 있어서, 단계 (a)의 반응은 110 내지 140℃의 온도에서, 디메틸포름아미드 및 1-메틸피롤리딘-2-온으로 구성된 군에서 선택되는 용매 내에서 나트륨 아지드로 수행되는 방법.
  3. 제1항에 있어서, 단계 (c)에서, A형을 분리하기 위하여 이소프로판올이 사용되건, B형을 분리하기 위하여 에탄올/물 혼합물을 사용하는 방법.
  4. 조생성물 형태 또는 A형인 2-n. 부틸-3-〔〔 2′-(테트라졸-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온을 10%이상의 물으 함유하는 수-혼합성 용매 내에서 재결정함으로 구성되는, B형 2-n. 부틸-3-〔〔 2′-(테트라졸-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온의 제조방법.
  5. 표 I에 나타낸 X-레이 분말 회전 패턴을 가지는 B형의 2-n. 부틸-3-〔〔 2′-(테트라졸-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온
  6. 제5항에 있어서, 하기의 특성을 가짐을 특징으로 하는 B형의 2-n. 부틸-3-〔〔 2′-(테트라줄-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온 : -185-186℃의 융점;-1537, 1200 및 745㎝-1에서의 IR-고유 흡수
  7. 제1항 내지 제4항중 한 항에 따라 수득할 수 있는 B형의 2-n. 부틸-3-〔〔 2′-(테트라줄-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온
  8. 제5항 내지 7항중 한 항에 따른 B형의 2-n. 부틸-3-〔〔 2′-(테트라줄-5-일)비페닐-4-일〕메틸〕-1,3-디아자스피로〔4,4〕논-1-엔-4-온을유효성분으로서 함유하는 약학적 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019950036285A 1994-10-19 1995-10-19 2종 결정형의 테트라졸 유도체의 제조방법 및 그의 신규 결정형(process for the preparation of a tetrazole derivative in two crystalline forms and novel crystalline form of said derivative) KR100251222B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9412459A FR2725987B1 (fr) 1994-10-19 1994-10-19 Procede pour la preparation d'un derive de tetrazole sous deux formes cristallines et nouvelle forme cristalline de ce derive
FR94-12459 1994-10-19

Publications (2)

Publication Number Publication Date
KR960014122A true KR960014122A (ko) 1996-05-22
KR100251222B1 KR100251222B1 (ko) 2000-05-01

Family

ID=9467986

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019950036285A KR100251222B1 (ko) 1994-10-19 1995-10-19 2종 결정형의 테트라졸 유도체의 제조방법 및 그의 신규 결정형(process for the preparation of a tetrazole derivative in two crystalline forms and novel crystalline form of said derivative)

Country Status (27)

Country Link
US (1) US5629331A (ko)
EP (1) EP0708103B1 (ko)
JP (1) JP3366786B2 (ko)
KR (1) KR100251222B1 (ko)
CN (1) CN1061656C (ko)
AT (1) ATE198478T1 (ko)
AU (1) AU698041B2 (ko)
CA (1) CA2160725C (ko)
CY (1) CY2277B1 (ko)
CZ (2) CZ288629B6 (ko)
DE (1) DE69519788T2 (ko)
DK (1) DK0708103T3 (ko)
ES (1) ES2155115T3 (ko)
FI (1) FI114156B (ko)
FR (1) FR2725987B1 (ko)
GR (1) GR3035503T3 (ko)
HK (1) HK1005135A1 (ko)
HU (1) HU226461B1 (ko)
IL (1) IL115688A (ko)
NO (1) NO307516B1 (ko)
NZ (1) NZ280293A (ko)
PL (1) PL184193B1 (ko)
PT (1) PT708103E (ko)
RU (1) RU2144536C1 (ko)
SI (1) SI0708103T1 (ko)
TW (1) TW357147B (ko)
ZA (1) ZA958850B (ko)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5994348A (en) * 1995-06-07 1999-11-30 Sanofi Pharmaceutical compositions containing irbesartan
TW442301B (en) * 1995-06-07 2001-06-23 Sanofi Synthelabo Pharmaceutical compositions containing irbesartan
FR2780403B3 (fr) 1998-06-24 2000-07-21 Sanofi Sa Nouvelle forme de l'irbesartan, procedes pour obtenir ladite forme et compositions pharmaceutiques en contenant
GEP20033114B (en) 1998-07-06 2003-11-25 Bristol Myers Squibb Co Biphenyl Sulfonamides as Dual Angiotensin Endothelin Receptor Antagonists, Method for Their Production and Pharmaceutical Compositions Containing the Same
US20050176793A1 (en) * 2001-12-10 2005-08-11 Reddy Reguri B. Amorphous form of 2-n-butyl-3-((2-(1h-tetrazol-5-yl)([1,1'-biphenyl)-4-yl)methyl)-1, 3-diazaspiro(4,4')non-1-en-4-one
CN1668612A (zh) * 2002-07-16 2005-09-14 特瓦制药工业有限公司 厄贝沙坦的新合成方法
CN101165062A (zh) * 2003-01-16 2008-04-23 特瓦制药工业有限公司 伊贝沙坦的新合成方法
DE602004015071D1 (de) 2003-02-05 2008-08-28 Teva Pharma Synthese von 2-butyl-3-(2'-(1-trityl-1h-tetrazol-5-yl)biphenyl-4-yl)-1,3-diazaspiro-4,4 -nonen-4-on
AU2003242984A1 (en) * 2003-04-07 2004-11-01 Hetero Drugs Limited A novel crystalline form of irbesartan
WO2005051943A1 (en) * 2003-11-28 2005-06-09 Ranbaxy Laboratories Limited Processes for the preparation of highly pure irbesartan
CA2568640C (en) 2004-06-04 2011-08-09 Teva Pharmaceutical Industries Ltd. Pharmaceutical composition containing irbesartan
WO2006001026A1 (en) * 2004-06-23 2006-01-05 Hetero Drugs Limited Irbesartan polymorphs
SI21849A (sl) * 2004-07-29 2006-02-28 Krka, Tovarna Zdravil, D.D., Novo Mesto Priprava hidrokloridnih soli tetrazolskega derivata
TWI346108B (en) 2004-08-23 2011-08-01 Bristol Myers Squibb Co A method for preparing irbesartan and intermediates thereof
GB2419592A (en) * 2004-10-26 2006-05-03 Cipla Ltd Process for the preparation of irbesartan hydrochloride
US20090208573A1 (en) * 2004-11-11 2009-08-20 Lek Pharmaceuticals D.D Novel polymorph form of irbesartan
ES2259909B1 (es) * 2005-02-28 2007-06-16 Inke, S.A. Procedimiento para la obtencion de un compuesto farmaceuticamente activo y de su intermedio de sintesis.
EP1951714A1 (en) 2005-07-27 2008-08-06 Jubilant Organosys Limited Process for producing 2-(n-butyl)-3-[[2'-(tetrazol-5-yl)biphenyl- 4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one
EP1806130B1 (en) 2006-01-09 2010-03-31 KRKA, D.D., Novo Mesto Solid pharmaceutical composition comprising irbesartan
WO2008041957A1 (en) * 2006-10-03 2008-04-10 Ulkar Kimya Sanayi Ve Ticaret As Method for producing pure crystalline form of 2-n-butyl-3-((2-(1h-tetrazole-5-yl) (1,1'-biphenyl)-4-methyl)-1,3-diazapspiro (4,4') non -1- en-4-one
EP1918288A1 (en) 2006-11-02 2008-05-07 Cadila Pharmaceuticals Limited A novel and improved process for the preparation of Irbesartan, an angiotensin-II receptor antagonist for the treatment of hypertension
EP2065035B1 (en) * 2007-11-28 2010-07-21 Laboratorios Lesvi, S.L. Pharmaceutical formulations containing irbesartan
US20100234614A1 (en) * 2007-12-07 2010-09-16 Hetero Drugs Limited Process for pure irbesartan
KR101009383B1 (ko) * 2008-04-30 2011-01-19 켐젠주식회사 고순도의2-부틸-3-[[2'-(1에이취-테트라졸-5-일)[1,1'-비페닐]-4-일]메틸]-1,3-디아자스피로[4.4]논-1-엔-4-온 화합물의제조방법
EP2417110B1 (en) * 2009-04-08 2014-05-07 CTX Life Sciences Pvt. Ltd. A one pot process for preparing 2-butyl-3-[[2'-(1h-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1,3-diazaspiro [4, 4]non-1-en-4-one (irbesartan)
AR078107A1 (es) * 2009-08-31 2011-10-12 Sanofi Aventis Uso de irbesartan para la preparacion de un medicamento para la prevencion de la hospitalizacion por insuficiencia cardiaca
US8080670B2 (en) 2010-05-04 2011-12-20 Divi's Laboratories, Ltd. Process for the preparation of irbesartan
FR2977253B1 (fr) 2011-06-30 2013-08-09 Centre Nat Rech Scient Reactif organostannique alcoxyle supporte, preparation et utilisation pour la synthese de tetrazoles en phase heterogene
WO2018002673A1 (en) 2016-07-01 2018-01-04 N4 Pharma Uk Limited Novel formulations of angiotensin ii receptor antagonists
US11655220B2 (en) 2020-10-22 2023-05-23 Hetero Labs Limited Process for the preparation of angiotensin II receptor blockers
IL311793A (en) 2021-10-01 2024-05-01 Sanofi Sa A process for the preparation of active SARTAN compounds having a tetrazole ring

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2697919B2 (ja) * 1989-09-29 1998-01-19 キヤノン株式会社 信号内挿回路及び該回路を備えた変位測定装置
IE70593B1 (en) * 1989-09-29 1996-12-11 Eisai Co Ltd Biphenylmethane derivative the use of it and pharmacological compositions containing same
IL99372A0 (en) * 1990-09-10 1992-08-18 Ciba Geigy Ag Azacyclic compounds

Also Published As

Publication number Publication date
CZ288629B6 (cs) 2001-08-15
HUT73179A (en) 1996-06-28
FI954992A (fi) 1996-04-20
CZ271095A3 (en) 1996-05-15
ATE198478T1 (de) 2001-01-15
GR3035503T3 (en) 2001-06-29
NZ280293A (en) 1997-10-24
SI0708103T1 (en) 2001-04-30
ZA958850B (en) 1996-05-27
DK0708103T3 (da) 2001-04-23
RU2144536C1 (ru) 2000-01-20
HK1005135A1 (en) 1998-12-24
JPH08208642A (ja) 1996-08-13
CA2160725A1 (en) 1996-04-20
CN1128261A (zh) 1996-08-07
NO954154L (no) 1996-04-22
AU3433595A (en) 1996-05-02
FI954992A0 (fi) 1995-10-19
FR2725987B1 (fr) 1997-01-10
EP0708103B1 (fr) 2001-01-03
CA2160725C (en) 2001-12-18
PT708103E (pt) 2001-06-29
FR2725987A1 (fr) 1996-04-26
IL115688A (en) 1999-09-22
NO307516B1 (no) 2000-04-17
CZ288624B6 (cs) 2001-08-15
JP3366786B2 (ja) 2003-01-14
PL184193B1 (pl) 2002-09-30
CY2277B1 (en) 2003-07-04
TW357147B (en) 1999-05-01
AU698041B2 (en) 1998-10-22
IL115688A0 (en) 1996-01-19
PL311012A1 (en) 1996-04-29
ES2155115T3 (es) 2001-05-01
CN1061656C (zh) 2001-02-07
NO954154D0 (no) 1995-10-18
FI114156B (fi) 2004-08-31
US5629331A (en) 1997-05-13
HU226461B1 (en) 2008-12-29
EP0708103A1 (fr) 1996-04-24
DE69519788D1 (de) 2001-02-08
KR100251222B1 (ko) 2000-05-01
DE69519788T2 (de) 2001-08-30
HU9503016D0 (en) 1995-12-28

Similar Documents

Publication Publication Date Title
KR960014122A (ko) 2종 결정형의 테트라졸 유도체의 제조방법 및 그의 신규 결정형
RU95118109A (ru) Способ получения производного тетразола, способ получения формы b производного тетразола, форма b производного тетразола и фармацевтическая композиция на основе производного тетразола формы b
US3758476A (en) 2-(thienyl-3'-amino)-1,3-diazacycloalkenes
JP2002053767A5 (ko)
CH628902A5 (de) Verfahren zur herstellung von 7-beta-(2-oxyimino-2-arylacetamido)-cephalosporinen.
JP2002513021A (ja) １，３−二置換−４−オキソ環式尿素の製造方法
AU764260B2 (en) Method of producing cyclene
KR100809159B1 (ko) 로사탄의 개선된 제조방법
EP2016073A1 (en) Process for the preparation of pure irbesartan
US3812102A (en) Process for producing benzodiazepine derivatives
DE1918311C3 (de) Verfahren zur Herstellung von l-Carbamoylalkyl-l.S-dihydro^H-Mbenzodiazepin-2-on-derivaten
JPH0259582A (ja) 坑潰瘍活性を有する薬剤および化合物
JP4105821B2 (ja) ジアゾ化合物
SU701535A3 (ru) Способ получени производных 1,2,4-триазола или их солей
EP1098895A1 (fr) Procede pour la preparation du sel potassique du lintitript
Molina et al. 2-MBTHnTHIW1, 3.4-THI* DIAZOLIUn CATIONS AS USEFUL PRKCURSORS FOR THE PRBPUULTION OF 2-~ INO-1.3. 4-THIliDI~ OLE DKRIVATIYES AM] AS DEHYDRATING RBAGENTS OF ALWXIYgS
JPS606944B2 (ja) 新規ウラシル誘導体の製造方法
Drumm The Constitution of Catechin: Part I
JP2004285030A (ja) 疎水性化合物をスルホン化する製造方法
HU201031B (en) New chemical process.

Legal Events

Date Code Title Description
A201 Request for examination
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20121226

Year of fee payment: 14

FPAY Annual fee payment

Payment date: 20131219

Year of fee payment: 15

LAPS Lapse due to unpaid annual fee