KR890002117A - 4H-1-benzopyran-4-one derivative, preparation method thereof and use thereof as medicament - Google Patents

4H-1-benzopyran-4-one derivative, preparation method thereof and use thereof as medicament Download PDF

Info

Publication number
KR890002117A
KR890002117A KR1019870006829A KR870006829A KR890002117A KR 890002117 A KR890002117 A KR 890002117A KR 1019870006829 A KR1019870006829 A KR 1019870006829A KR 870006829 A KR870006829 A KR 870006829A KR 890002117 A KR890002117 A KR 890002117A
Authority
KR
South Korea
Prior art keywords
alkyl
compound
hydrogen
formula
cycloalkyl
Prior art date
Application number
KR1019870006829A
Other languages
Korean (ko)
Other versions
KR950013768B1 (en
Inventor
락스미나라얀 카티지 삼바
가나파티 나이크 람찬드라
다우드브하이 라크 다왈라 아프타브
세인 노만브하이 도하드 왈라 알리후
헬무트 루프 리차드
데 소오자 노엘존
Original Assignee
하인리히 벡커, 베른하르트 베크
훽스트 아크티엔게젤샤프트
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 하인리히 벡커, 베른하르트 베크, 훽스트 아크티엔게젤샤프트 filed Critical 하인리히 벡커, 베른하르트 베크
Priority to KR87006829A priority Critical patent/KR950013768B1/en
Publication of KR890002117A publication Critical patent/KR890002117A/en
Application granted granted Critical
Publication of KR950013768B1 publication Critical patent/KR950013768B1/en

Links

Classifications

    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond

Landscapes

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

Abstract

내용 없음No content

Description

4H-1-벤조피란-4-온 유도체, 이의 제조방법 및 약제로서의 이의 용도4H-1-benzopyran-4-one derivative, preparation method thereof and use thereof as medicament

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

Claims (12)

하기 일반식(I)이 화합물 및 이의 약물학적으로 허용되는 산부가염 및 광학적 이성체.Formula (I) is a compound and its pharmaceutically acceptable acid addition salts and optical isomers. 상기식에서 R1은 수소, 비치환되거나 치환된 C1-C6-알킬, 아릴-C1-C4-알킬C1-C6-사이클로알킬, C3-C6-사이클로알킬-C1-C6-알킬, C2-C6-알케닐, C3-C6-알키닐, 아릴, 카복실 또는 알데히드 또는 -COO-C1-C4-알킬그룹이고, R2는 수소, C1-C6-알킬, 니트로, 아미노, 디-C1-C4-알킬아미노 또는 디-C1-C4-알킬아미노메틸 또는 할로겐원자이며, R3는 C1-C4-알킬, 치환된 C1-C4-알킬, 하이드록실, C1-C4-알콕시, 아릴C1-C4-알킬, 니트로 할로겐, 아미노, C1-C4-알킬아미노 또는 디- C1-C4-알킬아미노이고, R4는 수소, 하이드록실, C1-C4-알콕시, C1-C4-알카노일옥시, C1-C4-알콕시카보닐, 아릴옥시, 아미노, C1-C4-알킬아미노 또는 디-(C1-C4-알킬)-아미노이며, R5는 수소, C1-C6-알킬, 치환된 C1-C6-알킬, 아릴-C1-C4-알킬, C1-C6-사이클로알킬, C3-C6-사이클로알킬-C1-C4-알킬, C1-C4-알킬노일 또는 아로일이고, m은 0 내지 3의 정수이며, n은 0 내지 2의 정수이고, 단, 상기식에서 라세미 화합물 5,7-디하이드록시-2-메틸-8-[4'-(3-하이드록시-1-메틸)-피페리디닐]-4H-1-벤조피란-4-온은 제외된다.Is hydrogen, unsubstituted or substituted C 1 -C 6 -alkyl, aryl-C 1 -C 4 -alkylC 1 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, aryl, carboxyl or aldehyde or -COO-C 1 -C 4 -alkyl group, R 2 is hydrogen, C 1 -C 6 -alkyl, nitro, amino, di-C 1 -C 4 -alkylamino or di-C 1 -C 4 -alkylaminomethyl or a halogen atom, R 3 is C 1 -C 4 -alkyl, substituted C 1 -C 4 -alkyl, hydroxyl, C 1 -C 4 -alkoxy, arylC 1 -C 4 -alkyl, nitro halogen, amino, C 1 -C 4 -alkylamino or di-C 1 -C 4 -alkylamino R 4 is hydrogen, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkanoyloxy, C 1 -C 4 -alkoxycarbonyl, aryloxy, amino, C 1 -C 4 -alkyl amino or di - (C 1 -C 4 - alkyl) amino, and, R 5 is hydrogen, C 1 -C 6 - alkyl, substituted C 1 -C 6 - alkyl, aryl -C 1 -C 4 - alkyl, C 1 -C 6 - cycloalkyl Is an alkyl alkanoyl or aroyl, m is an integer from 0 to 3, n is an integer from 0 to 2, and-kill, C 3 -C 6 - cycloalkyl, -C 1 -C 4 - alkyl, C 1 -C 4 Provided that the racemic compound 5,7-dihydroxy-2-methyl-8- [4 '-(3-hydroxy-1-methyl) -piperidinyl] -4H-1-benzopyran-4- ON is excluded. 제1항에 있어서, R1, R2및 R5가 상기에서 정의된 바와 같고, R3및 R4가 하이드록실그룹이며, m이 2이고 n이 1인 화합물.The compound of claim 1 , wherein R 1 , R 2 and R 5 are as defined above, R 3 and R 4 are hydroxyl groups, m is 2 and n is 1. 4. 제1항에 있어서, R1이 수소 또는 C1-C3-알킬이고, R2가 수소 또는 C1-C3-알킬이며, R3및 R4가 각각 하이드록실그룹이고, R5가 C1-C3-알킬 또는 C3-C5-사이클로알킬이며, m이 2이고 n이 1인 화합물.The compound of claim 1, wherein R 1 is hydrogen or C 1 -C 3 -alkyl, R 2 is hydrogen or C 1 -C 3 -alkyl, R 3 and R 4 are each a hydroxyl group, and R 5 is C 1- C 3 -alkyl or C 3 -C 5 -cycloalkyl, wherein m is 2 and n is 1. 시스-(±)-2-(2-클로로페닐)-5,7-디하이드록시-8-[4'-(3-하이드록시-1'-메틸)-피페리디닐]-4H-1-벤조피란-4-온 및 이의 약물학적으로 허용되는 산부가염.Cis- (±) -2- (2-chlorophenyl) -5,7-dihydroxy-8- [4 '-(3-hydroxy-1'-methyl) -piperidinyl] -4H-1- Benzopyran-4-one and its pharmacologically acceptable acid addition salts. 시스-(-)-2-(2-클로로페닐)-5,7-디하이드록시-8-[4'-(3-하이드록시-1'-메틸)-피페리디닐]-4H-1-벤조피란-4-온 및 이의 약물학적으로 허용되는 산부가염.Cis-(-)-2- (2-chlorophenyl) -5,7-dihydroxy-8- [4 '-(3-hydroxy-1'-methyl) -piperidinyl] -4H-1- Benzopyran-4-one and its pharmacologically acceptable acid addition salts. 시스-(-)-2-페닐-5,7-디하이드록시-8-[4'-(3-하이드록시-1'-메틸)-피페리디닐]-4H-1-벤조피란-4-온 및 이의 약물학적으로 허용되는 산부가염.Cis-(-)-2-phenyl-5,7-dihydroxy-8- [4 '-(3-hydroxy-1'-methyl) -piperidinyl] -4H-1-benzopyran-4- Warm and pharmacologically acceptable acid addition salts thereof. 시스-(±)-2-페닐-5,7-디하이드록시-8-[4'-(3'-하이드록시-1'-메틸)-피페리디닐]-4H-1-벤조피란-4-온 및 이의 약물학적으로 허용되는 산부가염.Cis- (±) -2-phenyl-5,7-dihydroxy-8- [4 '-(3'-hydroxy-1'-methyl) -piperidinyl] -4H-1-benzopyran-4 Warm and pharmacologically acceptable acid addition salts thereof. 시스-(±)-2-(p-플루오로페닐)-5,7-디하이드록시-8-[4'-(3-하이드록시-1'-메틸)-피페리디닐]-4H-1-벤조피란-4-온 및 이의 약물학적으로 허용되는 산부가염.Cis- (±) -2- (p-fluorophenyl) -5,7-dihydroxy-8- [4 '-(3-hydroxy-1'-methyl) -piperidinyl] -4H-1 -Benzopyran-4-one and its pharmacologically acceptable acid addition salts. 시스-(±)-2-(2-피리딜)-8-[4'-(3-하이드록시-1'-메틸)-피페리디닐]-4H-1-벤조피란-4-온 및 이의 약물학적으로 허용되는 산부가염.Cis- (±) -2- (2-pyridyl) -8- [4 '-(3-hydroxy-1'-methyl) -piperidinyl] -4H-1-benzopyran-4-one and its Pharmacologically acceptable acid addition salts. 일반식(XII)의 화합물을 알칼리금속 또는 알칼리금속 수소화물 및 일반식 R1-COO-알킬의 산의 알킬에스테르와 반응시켜 일반식(XIII)의 디케톤을 수득하고, 생성된 화합물을 무기산과 반응시킴으로써 폐환시켜 R4가 하이드록실그룹이고 R2가 수소인 일반짓(I)의 화합물을 수득하거나, 경우에 따라, R5가 CH3인 일반식(I)의 화합물을, 하이드록시그룹을 보호시킨 후에, 브롬화시아노겐과 반응시키고 생성된 화합물을 산성 또는 알칼리성 조건하에서 반응시켜 R5가 수소인 일반식(I)의 화합물을 수득하거나, 경우에 따라, R5가 수소인 일반식(I)의 화합물을 할라이드, 산 클로라이드, 토실레이트 및 에논과 갖은 적합한 친전자성 시약과 반응시켜 R5가 비치환되거나 치환된 C1-C6-알킬, 아릴-C1-C4-알킬, C3-C|6-사이클로알킬 또는 C3-C6-사이클로알킬 -C1-C4-알킬인 일반식(I)의 화합물을 수득하거나, 경우에 따라, R2가 수소인 일반식(I)의 화합물을 2급 아민하이드로클로라이드 및 파라포름알데히드와 반응시켜 R2가 디알킬아미노메틸인 일반식(I)의 화합물을 수득하거나, 또는 경우에 따라, R2가 수소인 일반식(I)의 화합물을 니트로화시켜 R2가 NO2인 일반식(I)의 화합물을 수득하거나, 경우에 따라, R2가 NO2인 일반식(I)의 화합물을 수소화시켜 R2가 아미노그룹인 일반식(I)의 화합물을 수득함을 특징으로 하여, 일반식(I)의 화합물 및 이의 약물학적으로 허용되는 산부가염 및 광학적 이성체를 제조하는 방법.The compound of formula (XII) is reacted with an alkyl ester of an alkali metal or alkali metal hydride and an acid of formula R 1 -COO-alkyl to give a diketone of formula (XIII), and the resulting compound is combined with an inorganic acid By ring reaction to obtain a compound of general formula (I) wherein R 4 is a hydroxyl group and R 2 is hydrogen, or optionally a compound of general formula (I) wherein R 5 is CH 3 to protect the hydroxy group After reacting with cyanogen bromide and reacting the resulting compound under acidic or alkaline conditions to give a compound of formula (I) wherein R 5 is hydrogen, or optionally, R 5 is hydrogen ) Is reacted with a suitable electrophilic reagent with halides, acid chlorides, tosylate and enones to form a substituted or substituted C 1 -C 6 -alkyl, aryl-C 1 -C 4 -alkyl, C 3 -C | Obtain a compound of formula (I) wherein 6 -cycloalkyl or C 3 -C 6 -cycloalkyl -C 1 -C 4 -alkyl, or optionally a compound of formula (I) wherein R 2 is hydrogen Reacting with secondary aminehydrochloride and paraformaldehyde to give a compound of formula (I) wherein R 2 is dialkylaminomethyl, or optionally a compound of formula (I) wherein R 2 is hydrogen To obtain a compound of formula (I) wherein R 2 is NO 2 , or optionally to hydrogenate a compound of formula (I) wherein R 2 is NO 2 , wherein R 2 is an amino group A process for preparing a compound of formula (I) and pharmacologically acceptable acid addition salts and optical isomers thereof, characterized by obtaining a compound of 상기식에서 R1은 수소, 비치환되거나 치환된 C1-C6-알킬, 아릴-C1-C4-알킬, C3-C6-사이클로알킬, C3-C6-사이클로알킬-C1-C6-알킬, C2-C6-알케닐, C3-C6-알키닐, 아릴, 카복실 또는 알데히드 또는 -COO-C1-C4-알킬그룹이고, R2는 수소, C|1-C6-알킬, 니트로, 아미노, 디-C1-C4-알킬아미노 또는 디-C1-C4-알킬아미노메틸 또는 할로겐원자이며, R3는 C1-C4-알킬, 치환된 C1-C4-알킬, 하이드록실, C1-C4-알콕시, 아릴C1-C4-알킬, 니트로 할로겐, 아미노, C1-C4-알킬아미노 또는 디- C1-C4-알킬아미노이고, R4는 수소, 하이드록실, C1-C4-알콕시, C1-C4-알카노일옥시, C1-C4-알콕시카보닐, 아릴옥시, 아미노, C1-C4-알킬아미노 또는 디-(C1-C4-알킬)-아미노이며, R5는 수소, C1-C6-알킬, 치환된 C1-C6-알킬, 아릴-C1-C4-알킬, C1-C6-사이클로알킬, C3-C6-사이클로알킬-C1-C4-알킬, C1-C4-알킬노일 또는 아로일이고, m은 0 내지 3의 정수이며, n은 0 내지 2의 정수이다.Wherein R 1 is hydrogen, unsubstituted or substituted C 1 -C 6 -alkyl, aryl-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1- C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, aryl, carboxyl or aldehyde or -COO-C 1 -C 4 -alkyl group, R 2 is hydrogen, C | 1- C 6 -alkyl, nitro, amino, di-C 1 -C 4 -alkylamino or di-C 1 -C 4 -alkylaminomethyl or a halogen atom, R 3 is C 1 -C 4 -alkyl, substituted C 1 -C 4 -alkyl, hydroxyl, C 1 -C 4 -alkoxy, arylC 1 -C 4 -alkyl, nitro halogen, amino, C 1 -C 4 -alkylamino or di-C 1 -C 4 -Alkylamino, R 4 is hydrogen, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkanoyloxy, C 1 -C 4 -alkoxycarbonyl, aryloxy, amino, C 1 -C 4 -alkylamino or di- (C 1 -C 4 -alkyl) -amino, R 5 is hydrogen, C 1 -C 6 -alkyl, substituted C 1 -C 6 -alkyl, aryl-C 1 -C 4 -Alkyl, C 1 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylnoyl or aroyl, m is an integer from 0 to 3 and n is an integer of 0-2. 제1항에서 청구된 일반식(I)의 화합물 또는 이의 약물학적으로 허용되는 산 부가염을 함유하는 약제.A medicament containing a compound of formula (I) as claimed in claim 1 or a pharmaceutically acceptable acid addition salt thereof. 소염 및/또는 면역 조절작용을 갖는 약제를 제조하는데 있어서의 제1항에서 청구된 화합물의 용도.Use of a compound as claimed in claim 1 in the manufacture of a medicament having anti-inflammatory and / or immunomodulatory activity. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR87006829A 1987-07-01 1987-07-01 4h-1-benzopyran-4-one derivatives KR950013768B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR87006829A KR950013768B1 (en) 1987-07-01 1987-07-01 4h-1-benzopyran-4-one derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR87006829A KR950013768B1 (en) 1987-07-01 1987-07-01 4h-1-benzopyran-4-one derivatives

Publications (2)

Publication Number Publication Date
KR890002117A true KR890002117A (en) 1989-04-08
KR950013768B1 KR950013768B1 (en) 1995-11-15

Family

ID=19262542

Family Applications (1)

Application Number Title Priority Date Filing Date
KR87006829A KR950013768B1 (en) 1987-07-01 1987-07-01 4h-1-benzopyran-4-one derivatives

Country Status (1)

Country Link
KR (1) KR950013768B1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100392468B1 (en) * 2000-09-18 2003-07-22 주식회사 엘지생명과학 3-Hydroxychromene-4-on derivatives useful as cyclin dependendent kinase inhibitors

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100392468B1 (en) * 2000-09-18 2003-07-22 주식회사 엘지생명과학 3-Hydroxychromene-4-on derivatives useful as cyclin dependendent kinase inhibitors

Also Published As

Publication number Publication date
KR950013768B1 (en) 1995-11-15

Similar Documents

Publication Publication Date Title
KR870010045A (en) 4H-1-benzopyran-4-one derivative and preparation method thereof
FR2371454A1 (en) NEW PHARMACEUTICAL COMPOSITIONS BASED ON PEPTIDIC ALKALOIDS OF RYE ERGOT
GB1425059A (en) 1,4-dihydropyridines their production and their medicinal use
ES8506677A1 (en) Novel 8-chloro-1,5-benzothiazepine derivatives, processes for preparing the same and pharmaceutical compositions.
ATE19878T1 (en) BENZIMIDAZOLE DERIVATIVES, PROCESS FOR THEIR MANUFACTURE AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
ES499870A0 (en) A PROCEDURE FOR THE PREPARATION OF INDANO DERIVATIVES
ES8506705A1 (en) 3-(1-Substituted-4-piperidyl)-1,2-benzisoxazoles, a process for the preparation thereof, a pharmaceutical composition comprising the same, and their use as medicaments.
KR920701177A (en) 3-aryloxazolidinone derivatives, methods for their preparation and therapeutic uses thereof
ATE108440T1 (en) ARYLAR ALKYL ETHER, PROCESS FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL COMPOSITION CONTAINING THERE.
DK96286A (en) 6-AMIDINO-2-NAPHTHYL-4-AMINO-BENZOATE DERIVATIVES AND PHARMACEUTICAL ACCEPTABLE ACID ADDITION SALTS THEREOF
ES463240A1 (en) Pyrazol-1-ylphenylacetic acids
KR890002117A (en) 4H-1-benzopyran-4-one derivative, preparation method thereof and use thereof as medicament
ES378520A1 (en) 4-morpholinoethoxy-benzophenones
ATE48994T1 (en) BENZIMIDAZOLE DERIVATIVE, PROCESS FOR ITS PRODUCTION AND PHARMACEUTICAL COMPOSITION.
JPS6434978A (en) Benzimidazole derivative, manufacture and application to medicine
US4261998A (en) Tetrahydro-isoquinoline derivatives
KR960017669A (en) Amphoteric Tricyclic Compound
GB2014141A (en) 8???-ethyl- and 8???-methyl-4,5??? epoxymorphinan-6-one compounds
KR910006310A (en) Novel naphthalene and tetrahydro naphthalene substituted gem-diphosphonate derivatives
JPH0667880B2 (en) gem-dihalo-1,8-diamino-4-aza-octane
US3322778A (en) Novel ether derivatives of benzmorphans
US3108045A (en) Metal chelates of oxazolidinones as central nervous system stimulants
KR910000648A (en) Phenoxypyridinamine and its derivatives, preparation methods and uses as medicaments
US3792048A (en) Process for hydrolyzing 3-trifluoromethyl phenethylamines
US3399204A (en) 2-(heterocyclic aminoalkyl)-cyclic ketone-2 carboxylic acid benzyl esters

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
G160 Decision to publish patent application
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20091110

Year of fee payment: 15

EXPY Expiration of term