KR840008157A - Process for preparing carbapenem derivatives - Google Patents

Process for preparing carbapenem derivatives Download PDF

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KR840008157A
KR840008157A KR1019840001243A KR840001243A KR840008157A KR 840008157 A KR840008157 A KR 840008157A KR 1019840001243 A KR1019840001243 A KR 1019840001243A KR 840001243 A KR840001243 A KR 840001243A KR 840008157 A KR840008157 A KR 840008157A
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carbon atoms
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덱스트레이즈 피에드
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원본미기재
브리스톨-마이어즈 컴페니
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    • C07D477/02—Preparation
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Abstract

내용 없음.No content.

Description

카르바페넴 유도체의 제조 방법Process for preparing carbapenem derivatives

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (12)

아래 구조식(Ⅳ)의 중간 물질을 아래 구조식(Ⅶ)의 티올 화합물과 불활성 용매 중에서 염기의 존재하에 반응시켜 아래 구조식(I′)의 카르바세펨 생성물을 얻고, 소망에 따라 카르복실 보호기 R2′를 제거하여 탈보호된 대응하는 화합물(I)을 얻는 것이 특징인 아래 구조식(I)의 카르바세펨 유도체 또는 약리학적으로 허용되는 그의 염의 제조방법.The intermediate of formula (IV) below is reacted with a thiol compound of formula (VII) in the presence of a base in an inert solvent to give a carbacefem product of formula (I ′), where desired, a carboxyl protecting group R 2 ′. A process for preparing a carbacefem derivative of the formula (I) below or a pharmacologically acceptable salt thereof, characterized by removing to obtain the corresponding deprotected compound (I). 위 각 식에서, R8은 수소이고, R1은 수소, 탄소 원자 수가 1-10개인 알킬, 알케닐 및 알키닐; 시클로 알킬 환 중의 탄소 원자 수는 3-6개이고 알킬 모핵의 탄소 원자 수는 1-6개인 시클로알킬 및 시클로알킬알킬, 페닐; 아릴 모핵이 페닐이고 지방족 부분의 탄소 원자 수는 1-6개인 아랄킬, 헤테로환 모핵중의 헤테로 원자 또는 원자들이 1-4개의 산소, 질소 또는 황원자 중에서 선정되고 상기 헤테로 모핵과 결합된 알킬 모핵의 탄소 원자 수가 1-6개인 헤테로아릴, 헤테로아랄킬, 헤테로시클릴 및 헤테로시틀릴알킬, 중에서 선택되는데, 상기 라디칼들에 관련된 치환체 또는 치환체들은 아미노, 할로, 히드록시 또는 카르복실 할로로 치환된In each formula, R8 is hydrogen, R1 is hydrogen, alkyl having 1-10 carbon atoms, alkenyl and alkynyl; Cycloalkyl and cycloalkylalkyl, phenyl having 3-6 carbon atoms in the cycloalkyl ring and 1-6 carbon atoms in the alkyl nucleus; Aralkyl having 1 to 6 carbon atoms in the aryl nucleus and an aliphatic moiety, an alkyl atom having a hetero atom or atoms in the heterocyclic nucleus selected from 1-4 oxygen, nitrogen or sulfur atoms and bonded to the hetero nucleus Heteroaryl, heteroaralkyl, heterocyclyl and heterocytylalkyl having 1 to 6 carbon atoms, wherein the substituents or substituents associated with the radicals are substituted with amino, halo, hydroxy or carboxyl halo 및 -NO2중에서 선택되며, 이들 치환체가 관련하는 R3및 R4는 각각 수소; 탄소 원자수가 1-10개인 치환 또는 미치환의 알킬, 알킬렌 및 알키닐; 시클로알킬 환중의 탄소 원자 수는 3-6개이고 알킬 모핵의 탄소 원자 수는 1-6개인 시클로알킬 및 시클로알킬알킬; 페닐; 아릴 모핵이 페닐이고 지방족 부분의 탄소 원자 수는 1-6개인 아랄킬 아랄케닐 및 알랄키닐; 헤테로환 모핵중의 헤테로 원자또는 원자들이 1-4개의 산소, 질소 또는 황원자 중에서 선정되고 상기헤테로 모핵과 결합된 알킬 모핵의 탄소 원자 수가 1-6개인 헤테로아릴, 헤테로아릴, 헤로아랄킬, 헤테로시클릴 및 헤테로시클릴킬; 중에서 선택되거나, 또는 R3과 R4는 그 중 최소한 하나가 질소 원자와 결합되는데, 이들은 모두 5원 또는 6원질소함유 헤테로환을 형성할 수도 있었으며, R9는 수소가 아닌것만을 제외하고는 R3의 정의와 같다. And —NO 2 , wherein R 3 and R 4 to which these substituents are associated are each hydrogen; Substituted or unsubstituted alkyl, alkylene and alkynyl having 1-10 carbon atoms; Cycloalkyl and cycloalkylalkyl having 3-6 carbon atoms in the cycloalkyl ring and 1-6 carbon atoms in the alkyl parent; Phenyl; Aralkyl arkenyl and alkynyl having an aryl nucleus phenyl and an aliphatic moiety having 1-6 carbon atoms; Heteroaryl, heteroaryl, heroaralkyl, heterocycle, wherein the heteroatoms or atoms in the heterocyclic nucleus are selected from 1-4 oxygen, nitrogen or sulfur atoms and the alkyl nucleus bonded to the heteronuclear nucleus has 1-6 carbon atoms; Reel and heterocyclyl; Or R 3 and R 4 , at least one of which is bonded to a nitrogen atom, all of which may form a 5- or 6-membered nitrogen-containing heterocycle, except that R 9 is not hydrogen Same as the definition of R 3 . 또는 R1과 R8은 모두 C2-C10알킬리덴 또는 히드록시로 치환된 알킬리덴을 나타내고, A는 시클로로펜틸렌, 시클로헥실렌이거나 한 개 이상의 C1-C4-알킬기로 임의 치환된 C2-C6알킬렌이며, R2은 수소, 음하전 또는 용이하게 제거할 수 있는 카르복실 보호기인데, R2가 수소 또는 보호기인 경우에는 역음이온이 존재하며, R14는 환 질소를 통하여 A에 결합됨으로써 사급 암모늄기를 형성하는 사급화 질소 함유방향족 또는 비방향족 헤테로환이다.Or R 1 and R 8 both represent alkylidene substituted with C 2 -C 10 alkylidene or hydroxy, and A is cychloropentylene, cyclohexylene or optionally substituted with one or more C 1 -C 4 -alkyl groups C 2 -C 6 alkylene, R 2 is hydrogen, a negatively charged or easily removable carboxyl protecting group, when R 2 is hydrogen or a protecting group, an anion is present, and R 14 is cyclic nitrogen It is a quaternized nitrogen containing aromatic or non-aromatic heterocycle which is bonded to A and forms quaternary ammonium group. 제1항에 있어서, 염기가 비친핵성 삼급 아민 또는 트리(C1-C4)알킬아민인 것이 특징은 방법.The method of claim 1, wherein the base is a nonnucleophilic tertiary amine or tri (C 1 -C 4 ) alkylamine. 제1항에 있어서, 염기가 비친핵성 삼급 아민인 것이 특징인 방법.The method of claim 1 wherein the base is a nonnucleophilic tertiary amine. 제1,2 또는 3항에 있어서, 반응의 진행 온도가 -15℃내지 최고 실온인 것이 특징인 방법.The process according to claim 1, 2 or 3, characterized in that the reaction temperature of the reaction is from -15 ° C. to the maximum room temperature. 제4항에 있어서, 반응의 진행 온도가 -15℃내지 +15℃인 것이 특징인 방법.The process according to claim 4, wherein the progress temperature of the reaction is -15 ° C to +15 ° C. 제1,2,3,4 또는 5항에 있어서, 불활성 용매가 아세토니트릴, 아세로니트릴 및 디에틸포름아미드의 혼합물, 테트라히드로류란 및 물의 혼합물, 아세토니트릴 및 물의 혼합물 및 아세톤 중에서 선정되는 것이 특징인 방법.The method according to claim 1, 2, 3, 4 or 5, wherein the inert solvent is selected from a mixture of acetonitrile, acetonitrile and diethylformamide, a mixture of tetrahydrosilane and water, a mixture of acetonitrile and water and acetone. Characteristic method. 아래 구조식Structural formula below 의 술피드를 강산 및 아래 구조식Sulfide of strong acid and below structural formula 의 헤테로 방향족 아민이나 아래 구조식Heteroaromatic amines or the structural formulas below 의 헤테로환 아민과 반응시키는 것을 특징으로 하는 아래구조식The following structural formula characterized in that the reaction with a heterocyclic amine 의 사급아민 티올 화합물의 제조방법.Method for producing a quaternary amine thiol compound. 위 각 식에서, A는 시클로펜틸렌, 시클로헥실렌 또는In each formula above, A is cyclopentylene, cyclohexylene or 이고, ego, R10,R11,R12및 R13은 각각 수소 또는 C1-C4-알킬이며,는 역음이온이고, R14는 환 내에 최소한 한 개의 질소 원자를 함유하여 환질소를 통하여 A에 결합하여 사급 암모늄기를 형성하는 치환 또는 미치환의 모노-, 디-또는 폴리환상 방향족 또는 비방향족 헤테로환 라디칼이며,은 사급화가 가능한 환 내에 최소한 한 개의 질소 원자를 함유하며 치환체 A의 탄소 원자에 결합되는 치환 또는 미치환의 모노-, 디-또는 폴리환상 방향족 또는 비방향족 헤테로환 라디칼이고,은 치환체 R16에 의하여 사급화가 가능한 환 내에 최소한 질소 원자를 함유하며 치환체 A의 탄소 원자에 결합되는 치환 또는 미치환의 모노-, 디-또는 폴리환상 방향족 또는 비방향족 헤테로환 라디칼이며, R16은 (1)임의 치환된 지방족, 시클로지방족, 시클로지방족-지방족, 아릴, 방향족-지방족, 헤테로아릴, 헤테로방향족-지방족 라디칼 또는 (2)에 결합하여 가교 결합 폴리환기를 형성하는 이가 페닐렌 또는 C1-C4알킬렌기이다.R 10 , R 11 , R 12 and R 13 are each hydrogen or C 1 -C 4 -alkyl, Is an anion, R 14 contains at least one nitrogen atom in the ring and is substituted or unsubstituted mono-, di- or polycyclic aromatic or non-aromatic heterocyclic ring which is bonded to A via ring nitrogen to form quaternary ammonium group Radicals, Is a substituted or unsubstituted mono-, di- or polycyclic aromatic or non-aromatic heterocyclic radical containing at least one nitrogen atom in the quaternizable ring and bonded to the carbon atom of substituent A, Is a substituted or unsubstituted mono-, di- or polycyclic aromatic or non-aromatic heterocyclic radical containing at least a nitrogen atom in the ring quaternizable by substituent R 16 and bonded to a carbon atom of substituent A, and R 16 is (1) any substituted aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, aryl, aromatic-aliphatic, heteroaryl, heteroaromatic-aliphatic radicals or (2) It is a divalent phenylene or C 1 -C 4 alkylene group that forms a cross-linked poly ventilation bind to. 제7항에 있어서, 반응 진행 온도가 약 20℃ 내지 약100℃인 것이 특징인 방법.8. The method of claim 7, wherein the reaction progress temperature is from about 20 ° C to about 100 ° C. 제7 또는 8항에 있어서, 강산이 염산, 브롬산, 메탄술폰산 p-톨루엔술폰산 또는 트리플루오로메탄술폰산인 것이 특징인 방법.The method according to claim 7 or 8, wherein the strong acid is hydrochloric acid, bromic acid, methanesulfonic acid p-toluenesulfonic acid or trifluoromethanesulfonic acid. 제7항에 있어서, 반응이 비극성 유기 용매 존재하에 진행되는 것이 특징인 방법.8. The process of claim 7, wherein the reaction proceeds in the presence of a nonpolar organic solvent. 제10항에 있어서, 비극성 유기 용매가 염화메틸렌, 벤젠, 크실렌 또는 톨루엔인 것이 특징인 방법.The method of claim 10 wherein the nonpolar organic solvent is methylene chloride, benzene, xylene or toluene. 제7,8,9,10 또는 11항에 있어서, 아민과 술피드 시약이 모두 액체이거나 또는 아민은 고체, 술피드는 액체 그리고 고체 아민이 액체 술피드에 가용성인 경우, 반응이 용매추가 없이도 진행되는 것이 특징인 방법.12. The reaction of claim 7, 8, 9, 10 or 11 wherein the reaction proceeds without addition of solvent when both the amine and sulfide reagent are liquid or the amine is solid, sulfide is liquid and solid amine is soluble in liquid sulfide. Characterized by being. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
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