KR970074750A - Intermediates in Simvastatin Production - Google Patents

Intermediates in Simvastatin Production Download PDF

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Publication number
KR970074750A
KR970074750A KR1019970018306A KR19970018306A KR970074750A KR 970074750 A KR970074750 A KR 970074750A KR 1019970018306 A KR1019970018306 A KR 1019970018306A KR 19970018306 A KR19970018306 A KR 19970018306A KR 970074750 A KR970074750 A KR 970074750A
Authority
KR
South Korea
Prior art keywords
simvastatin
lovastatin
open
compound
preparing
Prior art date
Application number
KR1019970018306A
Other languages
Korean (ko)
Other versions
KR100503923B1 (en
Inventor
칸나 자그모한
쿠마 야텐드라
쿠마르 타퍼 라제쉬
미스라 사탸난다
엠. 디리프 쿠마 에스.
Original Assignee
에스 케이 파타와리
랜박시 래보러터리스 리미티드
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
Priority claimed from IN1683DE1996 external-priority patent/IN184809B/en
Priority claimed from US08/816,574 external-priority patent/US5763653A/en
Application filed by 에스 케이 파타와리, 랜박시 래보러터리스 리미티드 filed Critical 에스 케이 파타와리
Publication of KR970074750A publication Critical patent/KR970074750A/en
Application granted granted Critical
Publication of KR100503923B1 publication Critical patent/KR100503923B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being unsaturated and containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pyrane Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

로바스타틴(lovastatin)을 출발물질로 하여 시클로프포필아미드나 부틸아미드로 처리함으로서 피라논(pyranone)고리를 개방시키는 단계, 메틸기를 2-메틸부티레이트 곁사슬에 첨가하는 단계 및 개방된 피라논 고리를 폐쇄하여 심바스타틴(simvastatin)을 제조하는 단계를 포함하는 로바스타틴 또는 메비놀린산(mevinolinic acid)으로부터 심바스타틴염을 제조하는 방법.Treatment with cyclopropofamide or butylamide with lovastatin as a starting material to open the pyranone ring, to add methyl groups to the 2-methylbutyrate side chain, and to close the open pyranone rings. Method for preparing a simvastatin salt from lovastatin or mevinolinic acid comprising the step of preparing simvastatin (simvastatin).

본 발명은 개방된 피라논 고리의 두 개의 히드록시기를 보호(protect) 및 미보호(deprotect)없이 실행된다. 출발물질을 시클로프로필아민으로 처리하여 신규한 중간체인 로바스타틴 시클로프로필아미드를 거쳐 심바스타틴이 제조된다.The invention is practiced without protecting and deprotecting the two hydroxyl groups of the open pyranone ring. Simvastatin is prepared via a novel intermediate, lovastatin cyclopropylamide, by treating the starting material with cyclopropylamine.

Description

심바스타틴 제조에서의 중간체Intermediates in Simvastatin Production

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (6)

구조식 (Ⅲ')의 화합물 :Compound of formula (III '): 식 중, R1은 메틸, R3은 시클로프로필, n=1 또는 2Wherein R 1 is methyl, R 3 is cyclopropyl, n = 1 or 2 청구항 1에 있어서, n은 1인 것을 특징으로 하는 화합물(Ⅲ).The compound (III) according to claim 1, wherein n is 1. 청구항 1에 있어서, n은 2인 것을 특징으로 하는 화합물(Ⅲ).The compound (III) according to claim 1, wherein n is 2. 구조식 (Ⅰ)의 화합물 처리단계를 포함하는 구조식 (Ⅲ)의 화합물을 제조하는 방법 :A process for preparing a compound of formula (III) comprising the step of treating a compound of formula (I): 식중, R은 :식중, R2는 시클로프로필 아미드와; Na, k 또는 NH4 Wherein R is: Wherein R 2 is cyclopropyl amide; Na, k or NH 4 청구항 4에 있어서, R2는 NH4인 것을 특징으로 하는 구조식 (Ⅲ)의 화합물을 제조하는 방법.The method of claim 4, wherein R 2 is NH 4 . 청구항 4에 있어서, 구조식 (Ⅳ)의 화합물을 제조하기 위하여 메틸부티레이트 결사슬의 메틸화를 또한 포함하는 것을 특징으로 하는 구조식 (Ⅲ)의 화합물을 제조하는 방법.The process of claim 4, further comprising methylation of the methylbutyrate chain to prepare the compound of formula (IV). 식 중, R3은 상기와 같다.In formula, R <3> is as above. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019970018306A 1996-05-30 1997-05-12 Intermediates in Simvastatin Production KR100503923B1 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
IN1683DE1996 IN184809B (en) 1996-05-30 1996-05-30
IN1683/?/96 1996-05-30
ID1683/DEL/96 1996-07-30
US08/816574 1997-03-13
US08/816,574 US5763653A (en) 1997-03-13 1997-03-13 Key intermediates in the manufacture of simvastatin
US08/816,574 1997-03-13

Publications (2)

Publication Number Publication Date
KR970074750A true KR970074750A (en) 1997-12-10
KR100503923B1 KR100503923B1 (en) 2005-10-13

Family

ID=26324705

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019970018306A KR100503923B1 (en) 1996-05-30 1997-05-12 Intermediates in Simvastatin Production

Country Status (4)

Country Link
KR (1) KR100503923B1 (en)
CN (1) CN1101805C (en)
AU (1) AU692409B2 (en)
HR (1) HRP970436B1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20010009846A (en) * 1999-07-14 2001-02-05 구광시 Intermediates useful for manufacturing simvastatin and processes for the preparation thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103254076A (en) * 2008-05-09 2013-08-21 上海医药工业研究院 Synthesis method for simvastatin ammonium salt, used intermediate and preparation methods for both
CN103864611B (en) * 2013-12-24 2015-11-11 深圳华润九新药业有限公司 The preparation method of a kind of preparation method of Simvastatin alcohol acid compound, composition, composition and application thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20010009846A (en) * 1999-07-14 2001-02-05 구광시 Intermediates useful for manufacturing simvastatin and processes for the preparation thereof

Also Published As

Publication number Publication date
HRP970436B1 (en) 2003-06-30
CN1173488A (en) 1998-02-18
HRP970436A2 (en) 1999-06-30
KR100503923B1 (en) 2005-10-13
AU692409B2 (en) 1998-06-04
AU2140997A (en) 1998-01-29
CN1101805C (en) 2003-02-19

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