KR900016194A - Method for preparing quinazoline derivatives - Google Patents

Method for preparing quinazoline derivatives Download PDF

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KR900016194A
KR900016194A KR1019900005608A KR900005608A KR900016194A KR 900016194 A KR900016194 A KR 900016194A KR 1019900005608 A KR1019900005608 A KR 1019900005608A KR 900005608 A KR900005608 A KR 900005608A KR 900016194 A KR900016194 A KR 900016194A
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general formula
carried out
reaction
lower alkyl
following general
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KR1019900005608A
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Korean (ko)
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레이터 조세프
폰고 라스즐로
고르제니이 프리기에스
페케트 메르톤
크소르고 마르기트
스쭈헤르 일로나
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아띨라 만디, 메프톤 페케트
에기스 기오기스제르갸르
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Priority claimed from HU193189A external-priority patent/HU203342B/en
Priority claimed from HU193089A external-priority patent/HU203333B/en
Application filed by 아띨라 만디, 메프톤 페케트, 에기스 기오기스제르갸르 filed Critical 아띨라 만디, 메프톤 페케트
Publication of KR900016194A publication Critical patent/KR900016194A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Cardiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Heart & Thoracic Surgery (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

내용 없음.No content.

Description

퀴나졸린 유도체의 제조방법Method for preparing quinazoline derivatives

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

Claims (19)

퀴나졸린 유도체와 약제학적으로 허용가능한 그의 산부가염을 제조하는데 있어서, (a) 다음 일반식(III)으로 표시되는 이소티오우레아 유도체와 다음 일반식(IV)로 표시되는 아민을 150 내지 280℃의 온도범위에서 반응시키거나, 또는 (b) 다음 일반식(II)로 표시되는 화합물을 임의적으로 촉매존재하에서 고리화반응시켜서 다음 일반식(I)로 표시되는 퀴나졸린 유도체를 제조하고, 필요에 따라서는, 약제학적으로 허용가능한 산부가염으로 전환시키는 것을 특징으로 하는 다음 일반식(I)로 표시되는 퀴나졸린 유도체와 약제학적 허용가능한 그의 산부가염의 제조방법.In preparing a quinazoline derivative and a pharmaceutically acceptable acid addition salt thereof, (a) the isothiourea derivative represented by the following general formula (III) and the amine represented by the following general formula (IV) Reaction at a temperature range, or (b) optionally a cyclization reaction of a compound represented by the following general formula (II) in the presence of a catalyst to prepare a quinazoline derivative represented by the following general formula (I), if necessary A method for producing a quinazoline derivative represented by the following general formula (I) and a pharmaceutically acceptable acid addition salt thereof, characterized by converting to a pharmaceutically acceptable acid addition salt. 상기식에서, R1과 R2는 서로 같거나 다른 것으로서, 수소 또는 저급 알킬이고, 또 이들은 함께 에틸렌이나 트리메틸렌기를 형성할 수도 있고, R은 저급알킬 또는 페닐-저급알킬로서, 이때 페닐고리를 하나 또는 그 이상의 저급알킬기 및/또는 수소원자에 의해 임의적으로 치환될 수 있으며, n은 2 또는 3의 정수이다.Wherein R 1 and R 2 are the same as or different from each other, are hydrogen or lower alkyl, and they may together form an ethylene or trimethylene group, and R is lower alkyl or phenyl-lower alkyl, wherein Or optionally substituted with more lower alkyl groups and / or hydrogen atoms, n being an integer of 2 or 3. 제1항에 있어서, 상기 방법(a)에 따른 반응은 끓는점이 150℃이상인 용매, 바람직하기로는 디메틸포름아미드, 디메틸아세트아미드 또는 술포란 중에서 실행하여서 됨을 특징으로 하는 방법.The process according to claim 1, wherein the reaction according to process (a) is carried out in a solvent having a boiling point of at least 150 ° C, preferably in dimethylformamide, dimethylacetamide or sulfolane. 제1항에 있어서, 상기 방법(a)에 따른 반응은 150 내지 220℃의 온도범위에서 실행하여서 됨을 특징으로 하는 방법.The method according to claim 1, wherein the reaction according to the method (a) is carried out at a temperature range of 150 to 220 ° C. 제1항에 있어서, 상기 방법(b)에 따른 반응은 150 내지 280℃, 바람직하기로는 150 내지 220℃의 온도범위에서 실행하여서 됨을 특징으로 하는 방법.The process according to claim 1, wherein the reaction according to process (b) is carried out in a temperature range of 150 to 280 ° C, preferably 150 to 220 ° C. 제1항 또는 제4항에 있어서, 상기 방법(b)에 따른 반응은 용매를 사용하지 않고 실행하여서 됨을 특징으로 하는 방법.The process according to claim 1 or 4, wherein the reaction according to process (b) is carried out without using a solvent. 제1항 또는 제4항에 있어서, 상기 방법(b)에 따른 반응은 용매존재하에서 실행하여서 됨을 특징으로 하는 방법.The process according to claim 1 or 4, wherein the reaction according to process (b) is carried out in the presence of a solvent. 제1항에 있어서, 상기 방법(b)에 따른 반응은 촉매존재하에서 실행하여서 됨을 특징으로 하는 방법.A process according to claim 1, wherein the reaction according to process (b) is carried out in the presence of a catalyst. 제7항에 있어서, 상기 반응은 25 내지 130℃, 바람직하기로는 70 내지 100℃의 온도범위에서 실행하여서 됨을 특징으로 하는 방법.The process according to claim 7, wherein the reaction is carried out in a temperature range of 25 to 130 ° C., preferably 70 to 100 ° C. 제7항 또는 제8항에 있어서, 상기 반응은 용매로서 옥시염화인을 사용하고 촉매로는 삼염화인, 삼브롬화인 또는 루이스산을 사용하여서 됨을 특징으로 하는 방법.The process according to claim 7 or 8, wherein the reaction is carried out using phosphorus oxychloride as a solvent and phosphorus trichloride, phosphorus tribromide or Lewis acid as a catalyst. 제1항 내지 제9항중 어느 하나의 항에 있어서, 상기 일반식(I)에서 R1이 메틸, R2가 수소, n이 3인 화합물을 제조하기 위해서는 그와 동일한 R1, R2및 n을 갖는 상기 일반식(II), (III) 및 (IV)로 표시되는 화합물들을 출발물질로 하여서 됨을 특징으로 하는 방법.According to claim 1 to 9 Compounds any of the preceding, the formula R 1 is methyl in the (I), to R 2 is the production of hydrogen, and n is 3 same R and the 1, R 2 and n A method characterized in that the compounds represented by the general formula (II), (III) and (IV) having a starting material. 제1항 내지 제9항중 어느 하나의 항에 있어서, 상기 일반식(I)에서 R1과 R2가 함께 에틸렌기를 형성하고, n이 2인 화합물을 제조하기 위해서는 그와 동일한 R1, R2및 n을 갖는 상기 일반식(II), (III) 및 (IV)로 표시되는 화합물들을 출발물질로 하여서 됨을 특징으로 하는 방법.The method according to any one of claims 1 to 9, wherein in formula (I), R 1 and R 2 together form an ethylene group, and in order to prepare a compound in which n is 2, the same R 1 , R 2 And compounds represented by the general formulas (II), (III) and (IV) having n as starting materials. 제1항 내지 제11항중 어느 하나의 항에 따른 제조방법에 의해 제조되는 상기 일반식(I)로 표시되는 화합물.The compound represented by the said general formula (I) manufactured by the manufacturing method of any one of Claims 1-11. 상기 실시예들을 참고하여 실질적으로 상세하게 기술된 것과 같은 제조방법.Manufacturing method as described in substantially detail with reference to the above embodiments. 다음 일반식(II)로 표시되는 화합물.The compound represented by the following general formula (II). 상기식에서 R1과 R2는 서로 같거나, 다른 것으로서, 수소 또는 저급 알킬이고, 또 이들은 함께 에틸렌이나 트리메틸렌기를 형성할 수도 있고, n은 2 또는 3의 정수이다.Wherein R 1 and R 2 are the same as or different from each other, hydrogen or lower alkyl, and they may together form ethylene or trimethylene group, and n is an integer of 2 or 3. 다음 일반식(III)으로 표시되는 이소티오우레아 유도체와 다음 일반식(IV)로 표시되는 아민을 130℃를 초과하지 않는 온도에서 반응시켜서 됨을 특징으로 하는 다음 일반식(II)로 표시되는 화합물의 제조방법.The isothiourea derivative represented by the following general formula (III) and the amine represented by the following general formula (IV) are reacted at a temperature which does not exceed 130 degreeC of the compound represented by the following general formula (II) Manufacturing method. 상기 식에서 R1과 R2는 서로 같거나, 다른 것으로서, 수소 또는 저급 알킬이고, 또 이들은 함께 에틸렌이나 트리메틸렌기를 형성할 수도 있고, R은 저급알킬 또는 페닐-저급알킬로서, 이때 페닐고리는 하나 또는 그 이상의 저급알킬기 및/또는 수소원자에 의해 임의적으로 치환될 수 있으며, n은 2 또는 3의 정수이다.Wherein R 1 and R 2 are the same as or different from each other, hydrogen or lower alkyl, and they may together form an ethylene or trimethylene group, and R is lower alkyl or phenyl-lower alkyl, wherein the phenyl ring is Or optionally substituted with more lower alkyl groups and / or hydrogen atoms, n being an integer of 2 or 3. 제15항에 있어서, 상기 반응은 알콜 또는 극성의 비양자성 용매중에서 실행하여서 됨을 특징으로 하는 방법.The process of claim 15, wherein the reaction is carried out in an alcohol or a polar aprotic solvent. 제16항에 있어서, 상기 용매는 이소프로판올임을 특징으로 하는 방법.The method of claim 16, wherein the solvent is isopropanol. 제16항에 있어서, 상기 용매는 디메틸포름아미드임을 특징으로 하는 방법.The method of claim 16, wherein the solvent is dimethylformamide. 제15항 내지 제18항중 어느 하나의 항에 있어서, 상기 반응들은 25 내지 130℃온도범위에서 실행하여서 됨을 특징으로 하는 하는 방법.19. The process according to any one of claims 15 to 18, wherein the reactions are carried out in a temperature range of 25 to 130 ° C. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019900005608A 1989-04-21 1990-04-20 Method for preparing quinazoline derivatives KR900016194A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
HU1930/8919 1989-04-21
HU193189A HU203342B (en) 1989-04-21 1989-04-21 Process for producing quinazoline deivatives
HU193089A HU203333B (en) 1989-04-21 1989-04-21 Process for producing n-cyano-carboxamidine derivatives
HU1931/89 1989-04-21

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KR900016194A true KR900016194A (en) 1990-11-12

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JP (1) JPH02292282A (en)
KR (1) KR900016194A (en)
AT (1) AT398075B (en)
CA (2) CA2015066A1 (en)
CH (1) CH681300A5 (en)
DK (1) DK99090A (en)
ES (1) ES2019826A6 (en)
FI (1) FI902002A0 (en)
GB (1) GB2231571B (en)
GR (1) GR900100294A (en)
IT (1) IT1241128B (en)
PL (1) PL162976B1 (en)
RU (1) RU1838309C (en)
SE (1) SE9001402L (en)
YU (1) YU70890A (en)

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CA2077252C (en) * 1992-08-31 2001-04-10 Khashayar Karimian Methods of making ureas and guanidines, and intermediates therefor
ES2096518B1 (en) * 1994-03-28 1997-12-01 Grupo Farmaceutico Almirall S NEW RINGS.
WO2008015525A2 (en) * 2006-07-31 2008-02-07 Orchid Chemicals & Pharmaceuticals Limited An improved process for the preparation of alfuzosin hydrochloride
EP2152697A2 (en) 2007-05-04 2010-02-17 Actavis Group PTC EHF Process for the preparation of alfuzosin and salts thereof
WO2009016387A2 (en) 2007-08-02 2009-02-05 Cipla Limited Process for the preparation of alfuzosin hydrochloride

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US4044135A (en) * 1975-10-14 1977-08-23 Abbott Laboratories Antihypertensive agents
US4026894A (en) * 1975-10-14 1977-05-31 Abbott Laboratories Antihypertensive agents
GB1591490A (en) * 1977-08-04 1981-06-24 Abbott Lab 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-tetrahydrofuroyl)piperazine hydrochloride dihydrate
US4138561A (en) * 1977-09-30 1979-02-06 Bristol-Myers Company Cyanocarboxamidines and quinazoline process
FI57751C (en) * 1977-10-25 1980-10-10 Fermion Oy PROCEDURE FOR THE FRAMSTATION OF 6,7-DIMETOXY-ELLER 6,7,8-TRIMETOXY-4-AMINO-2- (4-SUBSTITUTES-PIPERAZIN-1-YL) -KINAZOLINE WITH BLODTRYCKSSAKANDE NETKAN
FI56836C (en) * 1977-10-25 1980-04-10 Fermion Oy 4-SUBSTITUTES OF PIPERAZIN-1- (N-ARYL-N'-CYANO) -CARBOXIMIDAMIDER BUTTER OF THE BREAST PREPARATION WITH PHARMACOLOGICAL PROPERTIES 6,7-DIMETOXY-ELLER 6,7,8-TRIMETOXY-2-AMINO -SUBSTITUERADE-Piperazine-1-YL) -KINAZOLINER
FR2421888A1 (en) * 1978-02-06 1979-11-02 Synthelabo ALKYLENE DIAMINE AMIDES AND THEIR APPLICATION IN THERAPEUTICS
FI59800C (en) * 1979-01-10 1981-10-12 Fermion Oy PROCEDURE FOR THE FRAMSTATION OF 6,7-DIMETOXY-4-AMINO-2- (4- (FURO-2-YL) -PIPERASIN-1-YL) -QUINAZOLINE
FI67699C (en) * 1979-01-31 1985-05-10 Orion Yhtymae Oy PROCEDURE FOR THE FRAMSTATION OF AV 6,7-DIMETOXY-4-AMINO-2- (4- (2-FUROYL) -1-PIPERAZINYL) QUINAZOLINE HYDROCHLORIDE WITH BLODTRYCKSSAENKANDE VERKAN
ATE32074T1 (en) * 1983-11-22 1988-02-15 Heumann Ludwig & Co Gmbh PROCESS FOR THE PREPARATION OF 4-AMINO-6,7DIMETHOXY-2-(4-(FURO-2-YL)-PIPERAZINE-1-YL)QUINAZOLINE AND ITS PHYSIOLOGICALLY ACCEPTABLE SALTS.

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GR900100294A (en) 1991-09-27
SE9001402D0 (en) 1990-04-20
DK99090A (en) 1990-10-22
FI902002A0 (en) 1990-04-20
SE9001402L (en) 1990-10-22
ES2019826A6 (en) 1991-07-01
CH681300A5 (en) 1993-02-26
RU1838309C (en) 1993-08-30
ATA93190A (en) 1994-01-15
GB2231571A (en) 1990-11-21
JPH02292282A (en) 1990-12-03
IT9020092A1 (en) 1991-10-20
IT1241128B (en) 1993-12-29
AT398075B (en) 1994-09-26
GB9008941D0 (en) 1990-06-20
PL284860A1 (en) 1991-03-11
GB2231571B (en) 1992-09-16
DK99090D0 (en) 1990-04-20
YU70890A (en) 1992-05-28
CA2015066A1 (en) 1990-10-21
CA2028953A1 (en) 1990-10-22
PL162976B1 (en) 1994-01-31
IT9020092A0 (en) 1990-04-20

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