KR880009930A - Heterocyclic Compounds, Methods for Making the Same, and Pharmaceutical Formulations - Google Patents

Heterocyclic Compounds, Methods for Making the Same, and Pharmaceutical Formulations Download PDF

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KR880009930A
KR880009930A KR870001430A KR870001430A KR880009930A KR 880009930 A KR880009930 A KR 880009930A KR 870001430 A KR870001430 A KR 870001430A KR 870001430 A KR870001430 A KR 870001430A KR 880009930 A KR880009930 A KR 880009930A
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compound
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formula
alkyl
hydrogen
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KR870001430A
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KR950011410B1 (en
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세메라로 끌라우디오
미첼리 디노
피에라치올리 다니엘
가비라찌 지오반니
데이비드 보드윅 알란
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글락소 에스. 페. 아.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
    • C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

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

Abstract

내용 없음.No content.

Description

헤테로시클릭 화합물, 이의 제조방법 및 약학적 제형Heterocyclic Compounds, Methods for Making the Same, and Pharmaceutical Formulations

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

Claims (13)

일반식(Ⅰ)의 화합물 및 생리학적으로 허용되는 이의 염.Compounds of formula (I) and physiologically acceptable salts thereof. 상기식에서, R1은 수소 또는 C1-4알킬이고, R2는 수소 또는 C1-4알킬이며, Alk는 메틸렌 또는 에틸렌 쇄이고, R3및 R4는 독립적으로 C1-4직쇄 또는 측쇄 알킬 그룹이며, R5는 C1-4알킬이고, R6은 C1-13알킬그룹, 또는 C1-3알킬로 치환될 수 있는 C5-8시클로알킬그룹이며, R7은 수소원자 또는 C1-3알킬그룹이다.Wherein R 1 is hydrogen or C 1-4 alkyl, R 2 is hydrogen or C 1-4 alkyl, Alk is methylene or ethylene chain, and R 3 and R 4 are independently C 1-4 straight or branched chain Is an alkyl group, R 5 is C 1-4 alkyl, R 6 is a C 1-13 alkyl group, or a C 5-8 cycloalkyl group which may be substituted with C 1-3 alkyl, and R 7 is a hydrogen atom or C 1-3 alkyl group. 제1항에 있어서, R1R2N은 아미노, 메틸아미노, 에틸아미노, 이소프로필아미노 또는 디메틸아미노 그룹이고, R3및 R4는 독립적으로 메틸 또는 에틸그룹이며, R5는 메틸그룹이고, R5은 시클로헥실, 에틸, 프로필, 이소프로필, 3급 부틸, 펜틸 또는 옥틸 그룹이며, R7은 수소원자이거나, 메틸 또는 에틸그룹인 화합물.The compound of claim 1, wherein R 1 R 2 N is an amino, methylamino, ethylamino, isopropylamino or dimethylamino group, R 3 and R 4 are independently methyl or ethyl group, R 5 is methyl group, R 5 is cyclohexyl, ethyl, propyl, isopropyl, tertiary butyl, pentyl or octyl group, and R 7 is a hydrogen atom or a methyl or ethyl group. 제1항 또는 제2항에 있어서, R1R2N은 메틸아미노, 이소프로필아미노 또는 디메틸아미노 또는 모르포리노 그룹이고, Alk는 메틸렌 쇄이며, R3및 R4는 에틸그룹이고, R5는 메틸그룹이며, R6은 이소프로필 또는 3급 부틸그룹이고 R7은 수소원자이거나, R5은 에틸, 이소프로필, 프로필, 3급 부틸 또는 펜틸그룹이고, R7은 메틸 또는 에틸그룹인 화합물.3. The compound of claim 1, wherein R 1 R 2 N is a methylamino, isopropylamino or dimethylamino or morpholino group, Alk is a methylene chain, R 3 and R 4 are ethyl groups, and R 5 Is methyl group, R 6 is isopropyl or tertiary butyl group and R 7 is hydrogen atom, R 5 is ethyl, isopropyl, propyl, tertiary butyl or pentyl group, R 7 is methyl or ethyl group . 제1항 내지 3항중 어느 한 항에 있어서, R6가 3급 부틸그룹인 화합물.The compound of any one of claims 1-3, wherein R 6 is a tertiary butyl group. 제1항에 있어서, 2-디메틸아미노메틸-6-메틸-4-(2-(3-(1, 1-디메틸에톡시)-3-옥소-1-프로페닐)페닐)-1, 4-디히드로피리딘-3, 5-디카복실산 디에틸 에스테르; 및 생리학적으로 허용되는 이의 염.The method of claim 1, wherein 2-dimethylaminomethyl-6-methyl-4- (2- (3- (1,1-dimethylethoxy) -3-oxo-1-propenyl) phenyl) -1, 4- Dihydropyridine-3, 5-dicarboxylic acid diethyl ester; And physiologically acceptable salts thereof. 제1항 내지 5항중 어느 한 항에 따른 화합물의 트란스-이성체.The trans-isomer of the compound according to any one of claims 1 to 5. 제1항 내지 5항중 어느 한 항에 따른 화합물의 S-에난티오머.S-enantiomer of a compound according to any one of claims 1 to 5. (a) 일반식(Ⅱ)의 화합물을 일반식 R1R2NH의 아민과 반응시켜 Alk가 메틸렌인 일반식(Ⅰ)의 화합물을 제조하거나, (b)일반식(Ⅳ)의 화합물을 팔라듐 염 및 유기 염기의 존재하에서 일반식 CH2=CR7CO2R6의 아크릴산 에스테르와 반응시켜 R1및/또는 R2가 수소가 아닌 일반식(Ⅰ)화합물의 트란스 이성체를 제조하거나, (c) 일반식(Ⅲ)의 화합물을 일반식 R1R2NH의 아민 또는 이의 염 및 포름알데히드와 반응시켜 Alk가 에틸렌인 일반식(Ⅰ)의 화합물을 제조하거나, (d) R6가 수소인 상응하는 일반식(Ⅰ)의 산을 에스테르화하거나, (e) 일반식(Ⅴ)의 화합물을 일반식 Ph3P=CR7CO2R6의 트리페닐포스포란과 반응시키거나, (f) 일반식(X)의 화합물을 디아미노에스테르 (XVⅡ)와 반응시켜 일반식(Ⅰ)의 화합물을 제조하거나, (g) 상응하는 일반식(Ⅰ)의 트란스 이성체의 용액에 광선을 조사하여 일반식(I)화합물의 시스 이성체를 제조하거나, (h) 광학적으로 활성인 산을 사용하여 적절한 일반식(I)의 화합물의 시스 또는 트란스 이성체를 분할함으로써 일반식(I)의 화합물의 분리된 S 및/도는 R에난티오머를 제조하고; 경우에 따라 생성된 일반식(Ⅰ)의 화합물 또는 이의 염을 생리학적으로 허용되는 이의 염으로 전환시킴을 특징으로 하여, 일반식(Ⅰ)의 화합물을 제조하는 방법.(a) reacting a compound of formula (II) with an amine of formula R 1 R 2 NH to prepare a compound of formula (I) wherein Alk is methylene, or (b) a compound of formula (IV) Reacting with an acrylic acid ester of the general formula CH 2 = CR 7 CO 2 R 6 in the presence of a salt and an organic base to prepare trans isomers of compounds of formula (I) in which R 1 and / or R 2 are not hydrogen, or (c ) A compound of formula (III) is reacted with an amine of formula R 1 R 2 NH or a salt thereof and formaldehyde to prepare a compound of formula (I) wherein Alk is ethylene, or (d) R 6 is hydrogen Esterifying the corresponding acid of general formula (I), or (e) reacting a compound of general formula (V) with triphenylphosphorane of general formula Ph 3 P = CR 7 CO 2 R 6 , or (f) The compound of general formula (X) is reacted with diamino ester (XVII) to prepare a compound of general formula (I), or (g) of the corresponding trans isomer of general formula (I). The solution is irradiated with light to prepare a cis isomer of the compound of formula (I), or (h) by dividing the cis or trans isomer of the compound of formula (I) with an optically active acid. Isolated S and / or R enantiomers of compounds of Optionally converting the resulting compound of formula (I) or a salt thereof into a physiologically acceptable salt thereof, wherein said compound of formula (I) is prepared. 상기식에서, R1은 수소 또는 C1-4알킬이고, R2는 수소 또는 C1-4알킬이며, Alk는 메틸렌 또는 에틸렌 쇄이고, R3및 R4는 독립적으로 C1-4직쇄 또는 측쇄 알킬 그룹이며, R5는 C1-4알킬이고, R6은 C1-13알킬그룹, 또는 C1-3알킬로 치환될 수 있는 C5-6시클로알킬그룹이며, R7은 수소원자 또는 C1-3알킬그룹이고, 단, 일반식(XVⅡ)의 경우, R1, R2, 및 R3는 상기 정의한 바와 같거나 이러한 그룹으로 전환시킬 수 있는 구룹이며, X는 이탈그룹이고, Hal는 브롬 또는 요오드이다.Wherein R 1 is hydrogen or C 1-4 alkyl, R 2 is hydrogen or C 1-4 alkyl, Alk is methylene or ethylene chain, and R 3 and R 4 are independently C 1-4 straight or branched chain An alkyl group, R 5 is C 1-4 alkyl, R 6 is a C 1-13 alkyl group, or a C 5-6 cycloalkyl group which may be substituted with C 1-3 alkyl, and R 7 is a hydrogen atom or C 1-3 alkyl group, provided that in the general formula (XVII), R 1 , R 2 , and R 3 are as defined above or a group which can be converted into such a group, X is a leaving group, Hal Is bromine or iodine. 약제학적으로 허용되는 담체 또는 희석제와 함께 제1항에 따른 화합물을 함유함을 특징으로 하는 약제학적 조성물.A pharmaceutical composition comprising a compound according to claim 1 together with a pharmaceutically acceptable carrier or diluent. 제9항에 있어서, 경구, 설하, 경피, 비경구 또는 직장투여용, 또는 흡입 또는 가스주입법에 의한 투여용으로 적합한 형태의 조성물.10. A composition according to claim 9, suitable for oral, sublingual, transdermal, parenteral or rectal administration, or for administration by inhalation or gas injection. 제10항에 있어서, 정제 또는 켑슐 형태의 경구 투여용 조성물.The composition for oral administration according to claim 10, in the form of a tablet or capsule. 제11항에 있어서, 활성성분의 용량이 0. 3내지 40㎎인 조성물.The composition of claim 11 wherein the dose of the active ingredient is between 0.3 and 40 mg. 제1항에 있어서, R1내지 R5및 R7이 제1항에서 정의한 바와 같고 R6이 수소원자인 일반식(Ⅰ)의 화합물.A compound of formula (I) according to claim 1, wherein R 1 to R 5 and R 7 are as defined in claim 1 and R 6 is a hydrogen atom. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019870001430A 1987-02-20 1987-02-20 A process for the preparation of heterocyclic compounds KR950011410B1 (en)

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