KR920021569A - Novel Platinum (II) Complexes and Preparation Methods - Google Patents

Novel Platinum (II) Complexes and Preparation Methods Download PDF

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Publication number
KR920021569A
KR920021569A KR1019910019969A KR910019969A KR920021569A KR 920021569 A KR920021569 A KR 920021569A KR 1019910019969 A KR1019910019969 A KR 1019910019969A KR 910019969 A KR910019969 A KR 910019969A KR 920021569 A KR920021569 A KR 920021569A
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South Korea
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platinum
bis
dioxolane
aminomethyl
ethyl
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KR1019910019969A
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Korean (ko)
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KR940010296B1 (en
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김대기
김강혁
감종식
조용백
김훈택
태주호
김기협
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이승동
주식회사 선경 인더스트리
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Priority to KR1019910019969A priority Critical patent/KR940010296B1/en
Application filed by 이승동, 주식회사 선경 인더스트리 filed Critical 이승동
Priority to HU9302461A priority patent/HU220869B1/en
Priority to DE69130261T priority patent/DE69130261T2/en
Priority to PCT/KR1991/000036 priority patent/WO1992016539A1/en
Priority to EP92902293A priority patent/EP0586378B1/en
Priority to JP4502604A priority patent/JP2801965B2/en
Priority to CA002106679A priority patent/CA2106679C/en
Priority to RU9193057869A priority patent/RU2067099C1/en
Priority to ES92902293T priority patent/ES2124251T3/en
Priority to AU91247/91A priority patent/AU654990B2/en
Priority to HU9502323A priority patent/HUT72890A/en
Priority to BR9107299A priority patent/BR9107299A/en
Priority to AT92902293T priority patent/ATE171455T1/en
Priority to HU9302461A priority patent/HUT65220A/en
Priority to IE068792A priority patent/IE920687A1/en
Priority to NZ241824A priority patent/NZ241824A/en
Priority to TW081101719A priority patent/TW207542B/zh
Priority to IL10116792A priority patent/IL101167A/en
Priority to PT100272A priority patent/PT100272B/en
Priority to PH44095A priority patent/PH30926A/en
Priority to CN92102045A priority patent/CN1038590C/en
Priority to CS92873A priority patent/CZ285904B6/en
Publication of KR920021569A publication Critical patent/KR920021569A/en
Priority to US08/117,096 priority patent/US5395947A/en
Priority to NO932824A priority patent/NO304652B1/en
Priority to FI934150A priority patent/FI934150A/en
Priority to AU74439/94A priority patent/AU7443994A/en
Application granted granted Critical
Publication of KR940010296B1 publication Critical patent/KR940010296B1/en
Priority to CN97120205A priority patent/CN1063753C/en
Priority to AU45338/97A priority patent/AU704409B2/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0086—Platinum compounds
    • C07F15/0093—Platinum compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/28—Radicals substituted by nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

내용 없음No content

Description

신규한 플라티늄(II) 착화합물과 그의 제조방법Novel Platinum (II) Complexes and Preparation Methods

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

Claims (21)

다음의 일반식(1)로 표시되는 플라티늄(II)착화합물.Platinum (II) complex compound represented by following General formula (1). 상기 식에서, R1과 R2는 같거나 다르고, 각각 수소원자 또는 C1내지 C4의 저급알킬기를 나타내거나, 혹은 함께 사이클로 알칸을 형성하며, 단 4,5-비스(아미노메틸)-1,3-디옥소란 부위에서 각 부재탄소의 절대 입체배위는 다음과 같이 표시되는 (4R,5S)이거나 (4R,5S)이다.Wherein R 1 and R 2 are the same or different and each represent a hydrogen atom or a lower alkyl group of C 1 to C 4 , or together form a cycloalkane, provided that 4,5-bis (aminomethyl) -1, The absolute steric coordination of each member carbon at the 3-dioxolan site is (4 R , 5 S ) or (4 R , 5 S ) 제1항에 있어서, 상기 저급알킬기가 메틸, 에틸, 프로필, 이소프로필, 이소부틸 또는tert-부틸인 화합물.The compound of claim 1, wherein the lower alkyl group is methyl, ethyl, propyl, isopropyl, isobutyl or tert -butyl. 제1항에 있어서, 상기 사이클로알칸은 사이클로펜탄 또는 사이클로헥산인 화합물.The compound of claim 1, wherein the cycloalkane is cyclopentane or cyclohexane. 제1항에 있어서, 상기 4,5-비스(아미노메틸)-1,3-디옥소란 부위에서 각 부재탄소의 절대 입체배위가 (4R, 5R)인 화합물.A compound according to claim 1, wherein the 4,5-bis (aminomethyl) -1,3-dioxolane, each member carbon absolute steric configuration is in the region (4 R, 5 R). (글리이코레이토-O,O')-[(4R, 5R)-4,5-비스(아미노메틸)-2,2-디메틸-1,3-디옥소란]플라티늄(II).(Glycidyl Ikoma reyito - O, O ') - [ (4 R, 5 R) -4,5- bis (aminomethyl) -2,2-dimethyl-1,3-dioxolane] platinum (II). (글리이코레이토-O,O')-[(4R, 5R)-4,5-비스(아미노메틸)-1,3-디옥소란-2-스피로-1'-사이클로펜탄]플라티늄(II).(Glycidyl Ikoma reyito - O, O ') - [ (4 R, 5 R) -4,5- bis (aminomethyl) -1,3-dioxolane-2-spiro-1'-cyclopentane] platinum ( II). (글라이코레이토-O,O')(사이클로헥산스피로-2'-[(4'R, 5'R)-4',5'-비스(아미노메틸)-1',3'-디옥소란])플라티늄(II).(Article lycopene reyito - O, O ') (cyclohexane spiro -2' - [(4 'R , 5' R) -4 ', 5'- bis (aminomethyl) -1', 3'-dioxolane ]) Platinum (II). (글리이코레이토-O,O')-[(4'R, 5'R)-4',5'-비스(아미노메틸)-2,2-에틸-1,3-디옥소란]플라티늄(II).(Glycidyl Ikoma reyito - O, O ') - [ (4' R, 5 'R) -4', 5'- bis (aminomethyl) -2-ethyl-1,3-dioxolane] platinum ( II). (글리이코레이토-O,O')-[(4'R, 5'R)-4',5'-비스(아미노메틸)-2-이소프로필-1,3-디옥소란]플라티늄(II).(Glycidyl Ikoma reyito - O, O ') - [ (4' R, 5 'R) -4', 5'- bis (aminomethyl) -2-isopropyl-1,3-dioxolane] platinum (II ). (글리이코레이토-O,O')-[(4'R, 5'R)-4',5'-비스(아미노메틸)-2,2-디에틸-1,3-디옥소란]플라티늄(II).(Glycidyl Ikoma reyito - O, O ') - [ (4' R, 5 'R) -4', 5'- bis (aminomethyl) -2,2-diethyl-1,3-dioxolane] platinum (II). (글리이코레이토-O,O')-[(4'R, 5'R)-4',5'-비스(아미노메틸)-2-에틸-2-메틸-1,3-디옥소란]플라티늄(II).(Glycidyl Ikoma reyito - O, O ') - [ (4' R, 5 'R) -4', 5'- bis (aminomethyl) -2-ethyl-2-methyl-1,3-dioxolane; Platinum (II). (글리이코레이토-O,O')-[(4'R, 5'R)-4',5'-비스(아미노메틸)-2-프로필-1,3-디옥소란]플라티늄(II).(Glycidyl Ikoma reyito - O, O ') - [ (4' R, 5 'R) -4', 5'- bis (aminomethyl) -2-propyl-1,3-dioxolane] platinum (II) . 다음 일반식(2)의 디할로게노디아민 플라티늄(II) 착화합물을 글라이콜산 및 산화은(I)과 반응시켜서 제1항에 따른 일반식(I)의 플라티늄(II) 착화합물을 제조하는 방법.A method of preparing the platinum (II) complex of formula (I) according to claim 1 by reacting the dihalogenodiamine platinum (II) complex of formula (2) with glycolic acid and silver oxide (I). 상기 식들에서, R1과 R2및 절대 입체배위는 상기 제1항에서 정의한 바와 같고, Hal은 할로겐 원자이다.In the above formulas, R 1 and R 2 and absolute steric coordination are as defined in claim 1, and Hal is a halogen atom. 제13항에 있어서, 상기 일반식(2)의 화합물과 상기 글리이콜산 및 상기 산화은(I)을 수성매질중에서 또는 수성매질과 알코올성 매질과의 혼합매질중에서 차광하에 0 내지 100℃를 유지하면서 1:0.5:0.5 내지 1:5:5의 당량비로 1시간 내지 3일간 반응시키는 것인 방법.The method according to claim 13, wherein the compound of formula (2), the glycoic acid and the silver oxide (I) are kept at 0 to 100 ° C. under shading in an aqueous medium or a mixed medium of an aqueous medium and an alcoholic medium. The reaction is carried out for 1 hour to 3 days at an equivalent ratio of 0.5: 0.5 to 1: 5: 5. 다음 일반식(2)의 디할로게노디아민 플라티늄(II) 착화합물과 질산은을 반응시켜서 다음 일반식(3)으로 표시되는 수화물의 수용액을 얻고, 이어서 이 수화물의 수용액을 음이온 교환수지가 충진된 컬럼을 통과시켜 다음 일반식(4)로 표시되는 화합물로 전환시킨 다음, 이 화합물의 수용액을 글라이콜산 및 글라이콜산 나트륨과 반응시켜서 제1항에 따른 다음 일반식(1)의 플라티늄(II)착화합물을 제조하는 방법.The dihalogenodiamine platinum (II) complex of the following general formula (2) is reacted with silver nitrate to obtain an aqueous solution of the hydrate represented by the following general formula (3). After passing through to convert the compound represented by the following general formula (4), the aqueous solution of the compound is reacted with glycolic acid and sodium glycolate to prepare the platinum (II) complex compound of the following general formula (1) How to prepare. 상기 식들에서, R1과 R2및 절대 입체배위는 제1항에서 정의한 바와 같고, Hal은 할로겐 원자이다.In the above formulas, R 1 and R 2 and absolute steric coordination are as defined in claim 1, and Hal is a halogen atom. 제15항에 있어서, 상기 음이온교환수지는 OH-형의 앰버라이트 IRA-400, 도웩스 I 또는 다이아이온 SA-10A인 것인 방법.16. The method of claim 15, wherein said anion exchange resin is an OH - type Amberlite IRA-400, Dox I or Diaion SA-10A. 제15항에 있어서, 상기 일반식(4) 화합물의 수용액과 글라이콜산 및 글라이콜산 나트륨을 수성매질중에서 차광하에 0 내지 100℃를 유지하면서 1:1:1 내지 1:1:5의 몰비로 1시간 내지 3일간 반응시키는 것인 방법.The molar ratio of the compound of claim 15, wherein the aqueous solution of the compound of the general formula (4) and the glycolic acid and sodium glycolate are maintained at 0 to 100 ° C. under shading in an aqueous medium. Reaction for 1 hour to 3 days. 다음 일반식(8)로 표시되는 4,5-비스(아미노메틸)-1,3-디옥소란.4,5-bis (aminomethyl) -1,3-dioxolane represented by the following general formula (8). 상기식에서, R1과 R2는 모두 에틸이거나, 그들중 어느 하나가 메틸이고 나머지 하나가 에틸이거나, 그들 중 어느 하나가 수소이고 나머지 하나가 프로필, 이소부틸 또는tert-부틸이며, 절대입체 배위는 제1항에서 정의한 바와 같다.Wherein R 1 and R 2 are both ethyl, either one of them is methyl and the other is ethyl, one of them is hydrogen and the other is propyl, isobutyl or tert -butyl, and the absolute stereo configuration is As defined in claim 1. 다음 일반식(7)으로 표시되는 4,5-비스(아지도메틸)-1,3-디옥소란.4,5-bis (azidomethyl) -1,3-dioxolane represented by the following general formula (7). 상기식에서, R1과 R2는 모두 에틸이거나, 그들중 어느 한나가 메틸이고 나머지 하나가 에틸이거나, 그들 중 어느 하나가 수소이고 나머지 하나가 프로필, 이소부틸 또는tert-부틸이며, 절대입체 배위는 제1항에서 정의한 바와 같다.Wherein both R 1 and R 2 are ethyl, either one of them is methyl and the other is ethyl, one of them is hydrogen and the other is propyl, isobutyl or tert -butyl, and the absolute stereo coordination is As defined in claim 1. 다음 일반식(6)로 표시되는 1,3-디옥소란-4,5-비스(메틴술포네이트).1,3-dioxolane-4,5-bis (methinesulfonate) represented by following General formula (6). 상기식에서, R1과 R2는 모두 에틸이거나, 그들중 어느 GK나가 메틸이고 나머지 하나가 에틸이거나, 그들 중어느 하나가 수소이고 나머지 하나가 프로필, 이소부틸 또는tert-부틸이며, 절대입체 배위는 제1항에서 정의한 바와 같다.Wherein both R 1 and R 2 are ethyl, either GK is methyl and the other is ethyl, one of them is hydrogen and the other is propyl, isobutyl or tert -butyl, As defined in claim 1. 제1항에 따른 디아민 플라티늄(II) 착화합물을 유효성분으로 함유하는 항암제 조성물.An anticancer composition comprising the diamine platinum (II) complex according to claim 1 as an active ingredient. ※ 참고사항:최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019910019969A 1991-03-23 1991-11-11 New pt(ñœ)complexes and process for the preparation thereof KR940010296B1 (en)

Priority Applications (28)

Application Number Priority Date Filing Date Title
KR1019910019969A KR940010296B1 (en) 1991-05-03 1991-11-11 New pt(ñœ)complexes and process for the preparation thereof
DE69130261T DE69130261T2 (en) 1991-03-23 1991-12-30 PLATINUM COMPLEXES AND METHOD FOR THE PRODUCTION THEREOF
PCT/KR1991/000036 WO1992016539A1 (en) 1991-03-23 1991-12-30 Novel platinum(ii) complex and processes for preparing the same
EP92902293A EP0586378B1 (en) 1991-03-23 1991-12-30 Novel platinum(ii) complex and processes for preparing the same
HU9302461A HU220869B1 (en) 1991-03-23 1991-12-30 Platinum(ii) complexes, pharmaceutical compositions comprising thereof and processes for preparing the same
CA002106679A CA2106679C (en) 1991-03-23 1991-12-30 Novel platinum (ii) complex and processes for preparing the same
RU9193057869A RU2067099C1 (en) 1991-03-23 1991-12-30 Platinum (ii) complex compounds, method of their synthesis, intermediate compounds and methods of their synthesis
ES92902293T ES2124251T3 (en) 1991-03-23 1991-12-30 NEW PLATINUM (II) COMPLEX AND PROCEDURES FOR ITS PREPARATION.
AU91247/91A AU654990B2 (en) 1991-03-23 1991-12-30 Novel platinum(II) complex and processes for preparing the same
HU9502323A HUT72890A (en) 1991-03-23 1991-12-30 Process for producing novel platinium complexes
BR9107299A BR9107299A (en) 1991-03-23 1991-12-30 New platinum II complex and processes for its preparation
AT92902293T ATE171455T1 (en) 1991-03-23 1991-12-30 PLATINUM COMPLEXES AND METHOD FOR THE PRODUCTION THEREOF
HU9302461A HUT65220A (en) 1991-03-23 1991-12-30 Process for producing new platinum(ii) complexes
JP4502604A JP2801965B2 (en) 1991-03-23 1991-12-30 Novel platinum (II) complex compound and method for producing the same
IE068792A IE920687A1 (en) 1991-03-23 1992-03-04 Novel platinum(ii) complex and processes for preparing the¹same
NZ241824A NZ241824A (en) 1991-03-23 1992-03-04 Platinum (ii) complexes of 4,5-bis(aminomethyl)-1,3- dioxolane derivatives; pharmaceutical compositions and 4,5-bis(aminomethyl and azidomethyl)-1,3-dioxolane derivatives
TW081101719A TW207542B (en) 1991-03-23 1992-03-06
IL10116792A IL101167A (en) 1991-03-23 1992-03-06 Platinum (II) complexes processes for the preparation thereof and pharmaceutical compositions containing the same
PT100272A PT100272B (en) 1991-03-23 1992-03-20 A NEW PLATINUM COMPLEX (II) AND PROCESS FOR THEIR PREPARATION
PH44095A PH30926A (en) 1991-03-23 1992-03-23 Platinum (II) complex and processes for preparing the same.
CN92102045A CN1038590C (en) 1991-03-23 1992-03-23 Platinum complex and processes for preparing same
CS92873A CZ285904B6 (en) 1991-03-23 1992-03-23 Platinum(ii) complex compounds, process of their preparation as well as pharmaceutical composition containing thereof
US08/117,096 US5395947A (en) 1991-03-23 1993-09-14 Platinum(II) complex and processes for preparing the same
NO932824A NO304652B1 (en) 1991-03-23 1993-09-22 Analogous methods for the preparation of therapeutically active platinum (II) complexes
FI934150A FI934150A (en) 1991-03-23 1993-09-22 NYA PLATINUM (II) COMPLEX OR FARING FARING FOR FRAMSTAELLNING AV DESSA
AU74439/94A AU7443994A (en) 1991-03-23 1994-10-05 Intermediates for the preparation of platinum (II) complexes
CN97120205A CN1063753C (en) 1991-03-23 1997-10-31 Method for preparing platinum compound
AU45338/97A AU704409B2 (en) 1991-03-23 1997-11-24 4,5-bis(aminomethyl and azidomethyl)-1,3-dioxolane intermediates useful for the preparation of platinum (II) complexes

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR90-7207 1991-05-03
KR91-7207 1991-05-03
KR910007207 1991-05-03
KR1019910019969A KR940010296B1 (en) 1991-05-03 1991-11-11 New pt(ñœ)complexes and process for the preparation thereof

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Publication Number Publication Date
KR920021569A true KR920021569A (en) 1992-12-18
KR940010296B1 KR940010296B1 (en) 1994-10-22

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