KR840006236A - 디하이드로 피리딘의 제조방법 - Google Patents
디하이드로 피리딘의 제조방법 Download PDFInfo
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- KR840006236A KR840006236A KR1019830004157A KR830004157A KR840006236A KR 840006236 A KR840006236 A KR 840006236A KR 1019830004157 A KR1019830004157 A KR 1019830004157A KR 830004157 A KR830004157 A KR 830004157A KR 840006236 A KR840006236 A KR 840006236A
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- compound
- alkyl
- formula
- dichlorophenyl
- chlorophenyl
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- 238000000034 method Methods 0.000 title claims 18
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 25
- -1 alkyl Substituted Chemical class 0.000 claims 22
- 239000002253 acid Substances 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- 231100000331 toxic Toxicity 0.000 claims 7
- 230000002588 toxic effect Effects 0.000 claims 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 125000004188 dichlorophenyl group Chemical group 0.000 claims 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- 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
- A61P9/06—Antiarrhythmics
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- 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
- A61P9/08—Vasodilators for multiple indications
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- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- 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
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical Kinetics & Catalysis (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
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- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Peptides Or Proteins (AREA)
Abstract
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Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (31)
- 일반식(IA)의 화합물을 일반식 R4·NCX의 이소시아네이트 또는 이소티오시아네이트와 반응시킴을 특징으로 하여 일반식(I)의 화합물을 제조하는 방법.(I)(IA)상기식에서, R은 할로 및 트리플루오로메틸 중에서 선택된 1개 또는 2개의 치환체에 의해 임의 치환된 페닐, 나프릴 또는 티아졸릴이고, R1및 R2는 각각 독립적으로 C1-C4알킬이며 : Y는 -(CH2)2-·-CH2CH(CH3)-·-CH2C(CH3)2-이고 : X는 산소 또는 황이며 : R4는 C1-C4알킬, C3-C6사이클로알킬, -COO(C1-C4알킬), -CH2COO(C1-C4알킬), C2H5CO2-페닐-, 플루오로페닐, 페닐, 알킬에 의해 치환된 -SO2페닐 또는 피리딜이다.
- 일반식(Ⅲ)의 화합물로 부터 보호그룹 Q를 제거함을 특징으로 하여 일반식(IA)의 화합물을 제조하는 방법.(IA)(Ⅱ)상기식에서, R, R1, R2및 Y는 제1항에서 정의한 바와 같고, Q는 보호그룹이다.
- 제2항에 있어서, Q가 수소화에 의해 제거되는 벤질 또는 4-클로로벤질 그룹이거나, 산에 의해 제거되는 트리틸 그룹인 방법.
- 일반식(IA)의 화합물을 일반식 Hal·CON(C1-C4알킬)2, Hal·CH2COR9, Hal·SO2R10.[여기서, R9, R10및 R11은 이하에서 정의하는 바와 같으며, "Hal"은 Cl또는 Br이다]의 알킬화제 또는 아실화제와 반응시킴을 특징으로 하여 일반식(Ⅲ)의 화합물을 제조하는 방법.(IA)(Ⅲ)상기식에서, R은 할로겐에 의해 치환된 페닐이고 : R1및 R2는 각가가 독립적으로 C1-C4알킬이며 : Y는 -(CH2)2-이고 : R3는 (i)-CON(C1-C4알킬)2, (ⅱ)-CH2COR9[여기서, R9는 -NH2, 메틸에 의해 이치환된 -NH·페닐 또는 C1-C4알콕시이다], (ⅲ)-SO2R10[여기서, R10은 -N(C1-C4알킬)2, 또는 C1-C4알킬이다] : 및 (ⅳ)-COR''[여기서, R''은 할로메틸, -COO(C1-C4알킬), -CH2O(C1-C4알킬), C1-C4알콕시, 피리딜, 푸릴, 모르폴리노 또는 5-옥소-피롤리딘-2-일이다]중에서 선택된다.
- 일반식(IA)의 화합물과 일반식 R3·SCH3의 화합물을 반응시킴을 특징으로 하여 일반식(Ⅲ)의 화합물을 제조하는 방법.(Ⅲ)(IA)상기식에서, R, R1, R2및 Y는 제4항에서 정의한 바와 같으며, R3는 T59 =N·R8또는[여기서, R7은 -CONH(C1-C4알킬) 또는 -COO(C1-C4알킬)이고, R8는 -CN, -SO2(C1-C4알킬)또는 -SO2, 페닐이다]이다.
- 일반식(ⅢA) 또는 (ⅢB)의 화합물을 각각 일반식 R5H(여기서, R5는 하기에서 정의하는 바와 같다)의 화합물 또는 (C1-C4알킬) NH2와 반응 시킴을 특징으로 하여 다음 일반식(Ⅲ)의 화합물을 제조하는 방법.(Ⅲ)(ⅢA)(ⅢB)상기식에서, R, R1, R2및 Y는 제4항에서 정의한 바와 같으며, R3는 T62 또는 T63 (C1-C4알킬)이고, R5는 1-피롤리디닐, -NH2, -NH(C1-C4알킬), -N(C1-C4알킬)2, 또는 -NH(CH2)2N(C1-C4알킬)2이며, R6는 C1-C4알킬 또는 페닐이다.
- 일반식(IA)의 화합물을 설프아미드, 디케텐 또는 포름산과 반응시킴을특징으로 하여 일반식(Ⅲ)의 화합물을 제조하는 방법.(IA)(Ⅲ)상기식에서, R, R1, R2및 Y는 제4항에서 정의한 바와 같으며, R3는 -SO2NH2, -COCH2COCH3또는 -CHO이다.
- 제1항에 있어서, 생성물을 무독한 산과 반응시켜 약학적으로 허용되는 산부가염을 전환시킴을 특징으로 하는 방법.
- 제1항에 있어서, R이 2-클로로페닐, 2-트리플루오로메틸페닐, 2, 3-디클로로페닐, 3, 5-디클로로페닐, 2, 6-디클로로페닐, 1-나프틸, 3-클로로페닐 또는 2-플루오로페닐이고, R1이 CH3이며, R2가 C2H5인 방법.
- 제9항에 있어서, Y가 -(CH2)2-인 방법.
- 제1항에 있어서, R이 2, 3-디클로로페닐이고, R1이 CH3이며, R2가 C2H5이고, Y가 -(CH2)2-인 일반식(IA)의 화합물을 메틸 이소시아네이트와 반응시켜 X가 0이고,R4가 CH3인 일반식(I)의 화합물을 제조하는 방법.
- 일반식(IA)의 화합물을 산의 존재하에서 칼륨시아네이트와 반응시킴을 특징으로 하여 일반식(I)의 화합물을 제조하는 방법.(I)(IA)상기식에서, R은 할로 및 트리플루오로 메틸중에서 선택된 1개 또는 2개의 치환체에 의해 임의 치환된 페닐, 나프틸 또는 티아졸릴이고 : R1및 R2는 각각 독립적으로 C1-C4알킬이며 : Y는 -(CH2)2-, -CH2CH(CH3)-, -CH2C(CH3)2-이고 : X는 산소이며 : R4는 H이다.
- 제12항에 있어서, 생성물을 무독한 산과 반응시켜 약학적으로 허용되는 산부가염으로 전환시킴을 특징으로 하는 방법.
- 제12항에 있어서, R이 2-클로로페닐 또는 2, 3-디클로로페닐이고, R1이 CH3이며, R2가 C2H5인 방법.
- 제14항에 있어서, Y가 -(CH2)2-인 방법.
- 제12항에 있어서, R이 2, 3-디클로로페닐이고 R1이 CH3이며, R2가 C2H5이고, Y가 -(CH2)2-인 일반식(IA)의 화합물을 산 존재하에서 칼륨 시아네이트와 반응시켜 R3가 -CONH2인 일반식(I)의 화합물을 제조하는 방법.
- 제2항에 있어서, 생성물을 무독한 산과 반응시켜 약학적으로 허용되는 산부가염으로 전환시킴을 특징으로 하는 방법.
- 제2항에 있어서, R이 2-클로로페닐, 2-트리플루로로메틸페틸, 2, 3-디클로로페닐, 3, 5-디클로로페닐, 2, 6-디클로로페닐, 1-나프틸, 3-클로로페닐 또는 2-플루오로페닐이고, R1이 CH3이며, R2가 C2H5인 방법.
- 제18항에 있어서, Y가 -(CH2)2-인 방법.
- 제4항에 있어서, 생성물을 무독한 산과 반응시켜 약학적으로 허용되는 산부가염으로 전환시킴을 특징으로 하는 방법.
- 제4항에 있어서, R이 1클로로페닐, 2-트리플로오로 메틸, 2, 3-디클로로페닐, 3, 5-디클로로페닐, 2, 6-디클로로페닐, 1-나프틸, 3-클로로페닐 또는 2-플로오로페닐이고, R1이 CH3이며, R2가 C2H5인 방법.
- 제21항에 있어서, Y가 -(CH2)2-인 방법.
- 제5항에 있어서, 생성물을 무독한 산과 반응시켜 약학적으로 허용되는 산부가염으로 전환시킴을 특징으로 하는 방법.
- 제5항에 있어서, R이 2-클로로페닐, 2-트리플루오로메틸페닐, 2, 3-디클로로페닐, 3, 5-디클로로페닐, 2, 6-디클로로페닐, 1-나프틸, 3-클로로페닐 또는 2-플로오로페닐이고, R1이 CH3이며, R2가 C2H5인 방법.
- 제24항에 있어서, Y가 -(CH2)2-인 방법.
- 제6항에 있어서, 생성물을 무독한 산과 반응시켜 약학적으로 허용되는 산부가염으로 전환시킴을 특징으로 하는 방법.
- 제6항에 있어서, R이 2-클로로페닐 또는 2-플루오로페닐이고, R1이 CH3이며, R2가 C2H5인 방법.
- 제27항에 있어서, Y가 -(CH2)2-인 방법.
- 제7항에 있어서, 생성물을 무독한 산과 반응시켜 약학적으로 허용되는 산부가염으로 전환시킴을 특징으로 하는 방법.
- 제7항에 있어서, R이 2-클로로페닐, 2-트리플루오로메틸페닐, 2, ]디클로로페닐, 3, 5-디클로로페닐, 2, 6-디클로로페닐, 1-나프틸, 3-클로로페닐 또는 2-플로오로페닐이고, R1이 CH3이며, R2가 C2H5인 방법.
- 제30항에 있어서, Y가 -(CH2)2-인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8225246 | 1982-09-04 | ||
| GB8225246 | 1982-09-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840006236A true KR840006236A (ko) | 1984-11-22 |
| KR880000180B1 KR880000180B1 (ko) | 1988-03-12 |
Family
ID=10532690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830004157A KR880000180B1 (ko) | 1982-09-04 | 1983-09-03 | 디하이드로 피리딘의 제조방법 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4539322A (ko) |
| EP (1) | EP0106462B1 (ko) |
| JP (1) | JPS5980663A (ko) |
| KR (1) | KR880000180B1 (ko) |
| AT (1) | ATE39112T1 (ko) |
| AU (1) | AU542454B2 (ko) |
| CA (1) | CA1205470A (ko) |
| CS (1) | CS242881B2 (ko) |
| DD (1) | DD215544A5 (ko) |
| DE (1) | DE3378632D1 (ko) |
| DK (1) | DK161700C (ko) |
| ES (2) | ES8604200A1 (ko) |
| FI (1) | FI80262C (ko) |
| GR (1) | GR78985B (ko) |
| HU (1) | HU191092B (ko) |
| IE (1) | IE55904B1 (ko) |
| IL (1) | IL69627A (ko) |
| NO (1) | NO160259C (ko) |
| NZ (1) | NZ205472A (ko) |
| PH (1) | PH19166A (ko) |
| PL (2) | PL143900B1 (ko) |
| PT (1) | PT77283B (ko) |
| SU (2) | SU1364237A3 (ko) |
| YU (2) | YU43659B (ko) |
| ZA (1) | ZA836514B (ko) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4568677A (en) * | 1983-07-23 | 1986-02-04 | Pfizer Inc. | 2-(4-Pyrimidone alkoxyalkyl) dihydropyridine anti-ischaemic and antihypertensive agents |
| GB8415386D0 (en) * | 1984-06-15 | 1984-07-18 | Pfizer Ltd | Therapeutic agents |
| GR851819B (ko) * | 1984-08-17 | 1985-11-26 | Wyeth John & Brother Ltd | |
| GB8421039D0 (en) * | 1984-08-17 | 1984-09-19 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| IT1204421B (it) * | 1986-06-27 | 1989-03-01 | Boehringer Biochemia Srl | 2-(aminoalchiltio)metil-1,4-diidropiridine,un metodo per la loro preparazione e composizioni farmaceutiche che le contengono |
| GB8527698D0 (en) * | 1985-11-09 | 1985-12-11 | Pfizer Ltd | Dihydropyridine antiischaemic & antihypertensive agents |
| JP2513197B2 (ja) * | 1986-01-21 | 1996-07-03 | 日本新薬株式会社 | ピログルタミド誘導体 |
| DE3621104A1 (de) * | 1986-06-24 | 1988-01-07 | Heumann Pharma Gmbh & Co | 1,4-dihydropyridinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US5138069A (en) * | 1986-07-11 | 1992-08-11 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking imidazoles |
| IT1197012B (it) * | 1986-07-29 | 1988-11-25 | Boehringer Biochemia Srl | 2-(aciltio) metil diidropiridine, un processo per la loro preparazione e composizioni farmaceutiche che le contengono |
| US4855001A (en) * | 1987-02-10 | 1989-08-08 | Lord Corporation | Structural adhesive formulations and bonding method employing same |
| GB8712747D0 (en) * | 1987-05-30 | 1987-07-01 | Pfizer Ltd | Therapeutic agents |
| EP0711554A4 (en) * | 1993-07-28 | 1997-07-23 | Nippon Shinyaku Co Ltd | ANTIDEPRESSANT |
| DE4410822A1 (de) * | 1994-03-24 | 1995-09-28 | Schering Ag | Neue Piperidin-Derivate |
| CA2207618A1 (en) * | 1994-12-23 | 1996-07-04 | Helmut Pieper | Piperazine derivatives, medicaments comprising these compounds, their use and processes for their preparation |
| US5700801A (en) * | 1994-12-23 | 1997-12-23 | Karl Thomae, Gmbh | Piperazine derivatives, pharmaceutical compositions containing these compounds, their use and processes for preparing them |
| US6756389B2 (en) * | 1996-08-09 | 2004-06-29 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| FR2829766A1 (fr) * | 2001-09-14 | 2003-03-21 | Lipha | Derives d'oxamates comportant un heterocycle azote diversement substitue |
| WO2022175384A1 (en) * | 2021-02-17 | 2022-08-25 | Fundación Universidad Católica De Valencia San Vicente Mártir | Small-molecule agents with antiviral activity against rna viruses |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1307256A (en) * | 1970-09-15 | 1973-02-14 | Science Union & Cie | Piperazine derivatives and a process for their preparation |
| DE2218644C3 (de) * | 1972-04-18 | 1982-08-19 | Bayer Ag, 5090 Leverkusen | Basische Ester von 1,4-Dihydropyridinen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
| US3943140A (en) * | 1972-09-30 | 1976-03-09 | Bayer Aktiengesellschaft | 2,3,5,6-Tetracarboxy-1,4-dihydropyridine derivatives |
| US3946027A (en) * | 1972-09-30 | 1976-03-23 | Bayer Aktiengesellschaft | 3,5,6-Tricarboxy-4-pyridyl-1,4-dihydropyridine derivatives |
| DE2248150A1 (de) * | 1972-09-30 | 1974-04-04 | Bayer Ag | Dihydropyridinpolyester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US3946028A (en) * | 1972-09-30 | 1976-03-23 | Bayer Aktiengesellschaft | 2,3,5,6-Tetracarboxy-4-pyridyl-1,4-dihydropyridine derivatives |
| GB1552911A (en) * | 1975-07-02 | 1979-09-19 | Fujisawa Pharmaceutical Co | 1,4 dihydropyridine derivatives and the preparation thereof |
| DE2658183A1 (de) * | 1976-12-22 | 1978-07-06 | Bayer Ag | In 2-position substituierte 1,4- dihydropyridin-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4177278A (en) * | 1977-04-05 | 1979-12-04 | Bayer Aktiengesellschaft | 2-Alkyleneaminodihydropyridines compounds, their production and their medicinal use |
| US4307103A (en) * | 1978-09-08 | 1981-12-22 | Fujisawa Pharmaceutical Co., Ltd. | Dihydropyridine derivative, processes for preparation thereof and pharmaceutical composition comprising the same |
| JPS5547656A (en) * | 1978-09-29 | 1980-04-04 | Dainippon Pharmaceut Co Ltd | 2-(2-substituted aminoethyl)-1,4-dihydropyridine derivative and its derivative |
| SE7910521L (sv) * | 1979-12-20 | 1981-06-21 | Haessle Ab | Nya 2-metyl-6-substituerade-4-(2,3-disubstituerad fenyl)-1,4-dihydropyridin-3,5-diestrar med hypotesiva egenskaper, samt forfarande for deras framstellning, och farmaceutiska beredningar innehallande desamma |
| CS228917B2 (en) * | 1981-03-14 | 1984-05-14 | Pfizer | Method of preparing substituted derivatives of 1,4-dihydropyridine |
-
1983
- 1983-08-24 PH PH29436A patent/PH19166A/en unknown
- 1983-08-26 AT AT83304954T patent/ATE39112T1/de not_active IP Right Cessation
- 1983-08-26 EP EP83304954A patent/EP0106462B1/en not_active Expired
- 1983-08-26 DE DE8383304954T patent/DE3378632D1/de not_active Expired
- 1983-08-30 ES ES525241A patent/ES8604200A1/es not_active Expired
- 1983-09-01 US US06/528,507 patent/US4539322A/en not_active Expired - Fee Related
- 1983-09-01 DK DK398383A patent/DK161700C/da not_active IP Right Cessation
- 1983-09-01 IE IE2058/83A patent/IE55904B1/en not_active IP Right Cessation
- 1983-09-01 FI FI833117A patent/FI80262C/fi not_active IP Right Cessation
- 1983-09-01 YU YU1785/83A patent/YU43659B/xx unknown
- 1983-09-02 ZA ZA836514A patent/ZA836514B/xx unknown
- 1983-09-02 AU AU18658/83A patent/AU542454B2/en not_active Ceased
- 1983-09-02 GR GR72365A patent/GR78985B/el unknown
- 1983-09-02 NZ NZ205472A patent/NZ205472A/en unknown
- 1983-09-02 SU SU833641411A patent/SU1364237A3/ru active
- 1983-09-02 DD DD83254486A patent/DD215544A5/de not_active IP Right Cessation
- 1983-09-02 PT PT77283A patent/PT77283B/pt not_active IP Right Cessation
- 1983-09-02 PL PL1983250618A patent/PL143900B1/pl unknown
- 1983-09-02 PL PL1983243621A patent/PL139499B1/pl unknown
- 1983-09-02 IL IL69627A patent/IL69627A/xx not_active IP Right Cessation
- 1983-09-02 CS CS836395A patent/CS242881B2/cs unknown
- 1983-09-02 HU HU833077A patent/HU191092B/hu not_active IP Right Cessation
- 1983-09-02 CA CA000435935A patent/CA1205470A/en not_active Expired
- 1983-09-02 NO NO833159A patent/NO160259C/no unknown
- 1983-09-03 KR KR1019830004157A patent/KR880000180B1/ko not_active IP Right Cessation
- 1983-09-05 JP JP58163103A patent/JPS5980663A/ja active Granted
-
1984
- 1984-04-30 ES ES532038A patent/ES532038A0/es active Granted
- 1984-06-11 SU SU843750492A patent/SU1378782A3/ru active
-
1985
- 1985-11-19 YU YU1799/85A patent/YU43598B/xx unknown
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