KR840006968A - 1,4-디하이드로 피리딘의 제조방법 - Google Patents
1,4-디하이드로 피리딘의 제조방법 Download PDFInfo
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- KR840006968A KR840006968A KR1019830006010A KR830006010A KR840006968A KR 840006968 A KR840006968 A KR 840006968A KR 1019830006010 A KR1019830006010 A KR 1019830006010A KR 830006010 A KR830006010 A KR 830006010A KR 840006968 A KR840006968 A KR 840006968A
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- 238000000034 method Methods 0.000 title claims 4
- 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 18
- 239000002253 acid Substances 0.000 claims 15
- -1 methylthio, methoxy, ethoxy Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 231100000331 toxic Toxicity 0.000 claims 9
- 230000002588 toxic effect Effects 0.000 claims 9
- 238000006243 chemical reaction Methods 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- BXULNSJILNIAEU-UHFFFAOYSA-N 1-(2-amino-1,3-oxazol-5-yl)ethanone Chemical compound CC(=O)C1=CN=C(N)O1 BXULNSJILNIAEU-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000002636 imidazolinyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical group [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Classifications
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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
-
- 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
- A61P9/08—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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
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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
- C07D401/14—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 three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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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- Obesity (AREA)
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- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (36)
- 다음 일반식(II)의 화합물을 다음 일반식(IIa)의 화합물과 반응시키고; 임의로
- (a) R3가 (C1―C4알콕시)카보닐 치환체를 갖는 일반식(I)의 생성물을 C1―C4알킬아민과 반응시켜서 R3가 N―(C1―C4알킬)카바모일 치환체를 갖는 생성물로 전환시키는 반응;
- (b) R3가 메톡시 치환체를 갖는 일반식(I)의 생성물을 암모니아와 반응시켜서 R3가 아미노 치환체를 갖는 생성물로 전환시키는 반응;
- (c) R3가 아미노 치환체를 갖는 일반식(I)의 생성물을 C1―C4알킬 이소시아네이트와 반응시켜서 R3가 ―NHCONH(C1―C4알킬) 치환체를 갖는 생성물로 전환시키는 반응;
- (d) R3가 클로로 또는 브로모 치환체를 갖는 일반식(I)의 생성물을 일반식 R4R5NH의 아민과 반응시켜서 R3가 일반식 ―NR4R5의 치환체를 갖는 생성물로 전환시키는 반응;
- (e) R3가 피라지닐―N―옥사이트 그룹인 일반식(I)의 생성물을 나트륨 디티오나이트로 환원시켜서 R3가 피라지닐 그룹인 생성물로 전환시키는 반응; 및
- (f) 일반식(I)의 생성물을 적합한 산과 반응시켜서 약제학적으로 무득한 산부가염으로 전환시키는 반응중의 하나이상을 수행함을 특징으로 하여 다음 일반식(I)의 화합물 또는 이의 약제학적으로 무독한 산부가염을 제조하는 방법.
-
- 상기식에서,
- R은 임의 치환된 아릴 또는 헤테로아릴 그룹이고;
- R1및 R2는 각각 독립적으로 C1―C4알킬 또는 2―메톡시 에틸이고;
- Y는 n이 2, 3 또는 4인 ―(CH2)n―이고 한개 또는 두개의 메틸 그룹으로 임의 치환되고;
- R3는 탄소원자에 의하여 인접한 질소 원자에 부착된 임의 치환된 5―또는 6―원환의 헤테로 사이클 그룹이고[여기에서, 헤테로사이클 그룹은 또다른 5―또는 6―원환의 헤테로사이클 그룹 또는 벤젠 고리에 임의로 융합되어 있고 이들 헤테로 그룹 및 벤젠고리는 또한 임의로 치환되어 있다]; R4및 R5는 각각 독립적으로 H 또는 C1―C4알킬이거나, R4및 R5가 그들이 부착된 질소원자와 함께, O, S, NH, N(C1―C4알킬) 및 N.CHO로부터 선택된 추가의 헤테로 원자 또는 그룹을 임의로 함유하는 포화된 5―또는 6―원환의 헤테로사이클 그룹을 나타내고; Q는 이탈 그룹을 나타낸다.
- 제1항에 있어서, Q가 ―NH NO2, C1―C4알킬티오, C1―C4알콕시, Cl, Cr 또는 I임을 특징으로 하는 방법.
- 제2항에 있어서, Q가 ―NH.NO2, 메틸티오, 메톡시, 에톡시 또는 클로로이고, Q가 메틸티오 또는 클로로일 때는, 반응을 트리에틸아민, 탄산나트륨 또는 4―디메틸아미노피리딘과 같은 염기의 존재하에 수행함을 특징으로 하는 방법.
- 다음 일반식(III)의 화합물을 하이드라진 또는 하이드라진 하이드레이트, 하이드록실아민, 메틸하이드라진 또는 하이드록실아민 및 나트륨 메톡사이드와 반응시키고 임의로 제1항에서 정의된 단계(c) 및 /또는 (f)를 수행함을 특징으로 하여
- 인 일반식(I)의 화합물 또는 이의 약제학적으로 무독한 산부가염을 제조하는 방법.
-
- 상기식에서
- X는 ―SCH3, ―OCH3또는 ―O페닐이다.
- 제4항에 있어서, X가 ―SCH3또는 ―OCH3임을 특징으로 하는 방법.
- 다음 일반식(IV)의 화합물을 BrCH2CHO 또는 ClCH2CHO, BrCH2CO(C1―C4알킬) 또는 ClCH2CO(C1―C4알킬), BrCH2COCOO(C1―C4알킬) 또는 ClCH2COCOO(C1―C4알킬) 또는 BrCH2COOEt 또는 ClCH2COOEt와 각각 반응시키고, 임의로 제1항에서 정의된 단계(a) 및/또는 (d)를 수행함을 특징으로 하여
-
- 또는
- 인 일반식(I)의 화합물 또는 이의 약제학적으로 무독한 산부가염을 제조하는 방법.
-
- 일반식(II)의 화합물을 Cl, CH2CH2NCS와 반응시키고, 임의로 일반식(I)의 생성물을 적합한 산과 반응시켜서 약제학적으로 무독한 산부가염으로 전환시킴을 특징으로 하여
- 인 일반식(I)의 화합물을 제조하는 방법.
- 다음 일반식(V)의 화합물을 처음에, 수소화나트륨과 같은 강염기와 다음에, 메틸 요오다이드와 마지막으로 하이드라진 또는 하이드라진 하이드레이트와 반응시키고, 임의로 생성물을 적합한 산과 반응시켜서 약제학적으로 무독한 산부가염으로 전환시킴을 특징으로 하여
- 인 일반식(I)의 화합물 또는 이의 약제학적으로 무독한 산부가염을 제조하는 방법.
-
- 제1항에 정의된 일반식(II)의 화합물을 5―아세틸―2―아미노―옥사졸과 반응시켜서 다음의 R3를 갖는 두 개의 생성물의 혼합물을 생성하고 이 생성물의 혼합물을 분리시키고, 임의로 생성물을 적합한 산과 반응시켜서 약제학적으로 무독한 산부가염으로 전환시킴.또는을 특징으로 하여 R3가 일반식(I)의 화합물 또는 이의 약제학적으로 무독한 산부가염을 제조하는 방법.
- 제1항 내지 9항 중 어느 하나에 있어서, R1이 CH3이고 R2가 C2H5이거나, R1이 C2H5이고 R2가 CH3이고, R이 2―클로로페닐, 2, 3―디클로로페닐 또는 2―클로로―3―트리플루오로메틸 페닐이고 Y가 (CH2)2임을 특징으로 하는 방법.
- 제1항 내지 3항 중 어느 하나에 있어서, R3가 트리아졸릴, 옥사디아졸릴, 피리미디닐 또는 이의 부분 포화된 유도체, 푸리닐, 퀴나졸티닐, 이미다졸릴, 이미다졸리닐, 트리아지닐, 피티딜, 티아졸릴, 티아졸티닐, 벤즈티아졸릴, 티아디아졸릴, 피라지닐, 퀴녹살리닐 및 피롤리닐 및 이들의 N―산화물 및 S―산화물로부터 선택되는 헤테로사이클 그룹이고 R3는 C1―C4알킬, C1―C4알콕시, 할로, 하이드록시, 옥소, 시아노, 3―메틸우레이도, 페닐, 페녹시, 피리딜, 아세틸, 카바모일, N―메틸카바모일(C1―C4알콕시)카보닐, ―NR4R5또는 ―SO2NR4R5[여기에서 R4및 R5는 각각 독립적으로 H 또는 C1―C4알킬이거나, R4및 R5가 그들이 부착되는 질소원자와 함께, 피페리디노, 모르플리노, 4―메틸피페라진―1―일 또는 4―포르밀피페라진―1―일 그룹을 형성한다]임을 특징으로 하는 방법.
- 제4항에 있어서, 화합물(III)에서 R이 2, 3―디클로로페닐이고, R1이 CH3이고, R2가 C2H5이고, Y가 (CH2)2이고 X가 ―SCH3이며, 화합물(III)을 하이드라진 하이드레이트와 반응시켜서 2―[2―(3―아미노―1H―1, 2, 4―트리아졸―5―일아미노)에톡시메틸]―4―(2, 3―디클로로페닐)―3―에톡시카보닐―5―메톡시카보닐―6―메틸―1, 4―디하이드로피리딘을 생성하고 이를 적합한 산과 반응시켜 약제학적으로 무독한 산부가염으로 임의전환시킴을 특징으로 하는 방법.
- ※참고사항:최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8236347 | 1982-12-21 | ||
| GB8236347 | 1982-12-21 |
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| Publication Number | Publication Date |
|---|---|
| KR840006968A true KR840006968A (ko) | 1984-12-04 |
| KR860001921B1 KR860001921B1 (ko) | 1986-10-25 |
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| KR1019830006010A KR860001921B1 (ko) | 1982-12-21 | 1983-12-19 | 1,4-디하이드로피리딘의 제조방법 |
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| Country | Link |
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| US (3) | US4572908A (ko) |
| EP (1) | EP0116769B1 (ko) |
| JP (1) | JPS59118782A (ko) |
| KR (1) | KR860001921B1 (ko) |
| AT (1) | ATE26114T1 (ko) |
| AU (1) | AU546057B2 (ko) |
| CA (1) | CA1215050A (ko) |
| CS (1) | CS249516B2 (ko) |
| DD (1) | DD213920A5 (ko) |
| DE (1) | DE3370481D1 (ko) |
| DK (1) | DK586583A (ko) |
| ES (2) | ES8506633A1 (ko) |
| FI (1) | FI79104C (ko) |
| GR (1) | GR81351B (ko) |
| HU (1) | HU193275B (ko) |
| IL (1) | IL70477A (ko) |
| NO (1) | NO159272C (ko) |
| NZ (1) | NZ206614A (ko) |
| PH (1) | PH20114A (ko) |
| PL (2) | PL140573B1 (ko) |
| PT (1) | PT77842B (ko) |
| SU (2) | SU1296006A3 (ko) |
| YU (2) | YU246883A (ko) |
| ZA (1) | ZA839381B (ko) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0125803A3 (en) * | 1983-04-27 | 1987-01-21 | FISONS plc | Pharmaceutically active dihydropyridines |
| GB8331120D0 (en) * | 1983-11-22 | 1983-12-29 | Pfizer Ltd | Benzaldehyde derivatives |
| DE3567460D1 (en) * | 1984-06-07 | 1989-02-16 | Pfizer Ltd | Dihydropyridines |
| GR851819B (ko) * | 1984-08-17 | 1985-11-26 | Wyeth John & Brother Ltd | |
| GB8601382D0 (en) * | 1986-01-21 | 1986-02-26 | Pfizer Ltd | Dihydropyridine antiischaemic & antihypertensive agents |
| US5202330A (en) * | 1985-06-03 | 1993-04-13 | E. R. Squibb & Sons, Inc. | 2-thio or oxo-4-aryl or heterocyclo-1,5(2H)-pyrimidinedicarboxylic acid diesters and 3-acyl-5-pyrimidinecarboxylic acids and esters |
| 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 |
| DE3531498A1 (de) * | 1985-09-04 | 1987-03-05 | Bayer Ag | Dihydropyridin-2-hydroxyamine, verfahren zur herstellung und ihre verwendung in arzneimitteln |
| US4820842A (en) * | 1986-11-19 | 1989-04-11 | Warner-Lambert Company | 2-substituted-1,4-dihydropyridines |
| IT1204948B (it) * | 1987-03-13 | 1989-03-10 | Boheringer Biochemia Robin S P | 2-tiometil-sostituite-piridine, metodo per la loro preparazione e composizioni farmaceutiche che le contengono. |
| US4753946A (en) * | 1987-04-08 | 1988-06-28 | E. R. Squibb & Sons, Inc. | Pyrimidinecarboxylic acid derivatives |
| GB9319341D0 (en) * | 1993-09-17 | 1993-11-03 | Wellcome Found | Novel process |
| GB9611046D0 (en) * | 1996-05-25 | 1996-07-31 | Wivenhoe Techn Ltd | Pharmacological compounds |
| ES2151850B1 (es) * | 1998-10-26 | 2001-08-16 | Esteve Quimica Sa | Intermedio para la sintesis de amlodipino para su obtencion y utilizacion correspondiente. |
| US6653481B2 (en) * | 2000-12-29 | 2003-11-25 | Synthon Bv | Process for making amlodipine |
| AU2001294354A1 (en) | 2000-12-29 | 2002-07-16 | Bioorganics B.V. | Process for making amlodipine, derivatives thereof, and precursors therefor |
| BR0116554A (pt) * | 2000-12-29 | 2004-02-03 | Pfizer Ltd | Composto, composição farmacêutica para o tratamento da angina ou hipertensão, processo, processo para o tratamento ou prevenção da angina ou hipertensão, composição do ingrediente farmaceuticamente ativo e composição farmacêutica para o tratamento ou prevenção da angina ou hipertensão |
| CA2501534A1 (en) | 2002-10-07 | 2004-04-22 | Artesian Therapeutics, Inc. | Dihydropyridine compounds having simultaneous ability to block l-type calcium channels and to inhibit phosphodiesterase type 3 activity |
| EP1975167A1 (en) * | 2007-03-30 | 2008-10-01 | Esteve Quimica, S.A. | Acetone solvate of phthaloyl amlodipine |
| JP2010100562A (ja) * | 2008-10-23 | 2010-05-06 | Daito Kk | アムロジピン製造中間体の精製方法 |
| CN102464608B (zh) * | 2010-11-15 | 2016-05-11 | 江苏先声药物研究有限公司 | 化合物及其作为l-型钙通道阻滞剂或/和乙酰胆碱酯酶抑制剂的应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4284634A (en) * | 1975-07-02 | 1981-08-18 | Fujisawa Pharmaceutical Co., Ltd. | 1,4-Dihydropyridine derivatives, and pharmaceutical method of the same |
| 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 |
| DE2740080A1 (de) * | 1977-09-06 | 1979-03-15 | Bayer Ag | 2-alkylenaminodihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4144343A (en) * | 1978-01-04 | 1979-03-13 | Merck & Co., Inc. | Heterocycle substituted (3-loweralkylamino-2-R1 O-propoxy)pyridines |
| JPS5547656A (en) * | 1978-09-29 | 1980-04-04 | Dainippon Pharmaceut Co Ltd | 2-(2-substituted aminoethyl)-1,4-dihydropyridine derivative and its derivative |
| DE2844595A1 (de) * | 1978-10-13 | 1980-04-30 | Bayer Ag | Acylaminodihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| 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 |
| DE3022030A1 (de) * | 1980-06-12 | 1981-12-17 | Bayer Ag, 5090 Leverkusen | 4-thiazol- bzw. 4-imidazol-substituierte, 1,4-dihydropyridine, verfahren zu deren herstellung sowie diese enthaltende arzneimittel |
| CS228917B2 (en) * | 1981-03-14 | 1984-05-14 | Pfizer | Method of preparing substituted derivatives of 1,4-dihydropyridine |
| DK161312C (da) * | 1982-03-11 | 1991-12-09 | Pfizer | Analogifremgangsmaade til fremstilling af 2-aminoalkoxymethyl-4-phenyl-6-methyl-1,4-dihydropyridin-3,5-dicarboxylsyreestere eller syreadditionssalte deraf samt phthalimidoderivater til anvendelse som udgangsmateriale ved fremgangsmaaden |
| DE3363743D1 (en) * | 1982-07-22 | 1986-07-03 | Pfizer Ltd | Dihydropyridine anti-ischaemic and antihypertensive agents |
| EP0107293A3 (en) * | 1982-09-04 | 1984-06-06 | Pfizer Limited | Dihydropyridines |
| US4515799A (en) * | 1983-02-02 | 1985-05-07 | Pfizer Inc. | Dihydropyridine anti-ischaemic and antihypertensive agents |
-
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- 1983-12-16 PT PT77842A patent/PT77842B/pt not_active IP Right Cessation
- 1983-12-16 PL PL1983250215A patent/PL140573B1/pl unknown
- 1983-12-16 PL PL1983245158A patent/PL140069B1/pl unknown
- 1983-12-16 US US06/562,482 patent/US4572908A/en not_active Expired - Lifetime
- 1983-12-19 EP EP83307719A patent/EP0116769B1/en not_active Expired
- 1983-12-19 AT AT83307719T patent/ATE26114T1/de not_active IP Right Cessation
- 1983-12-19 NO NO834689A patent/NO159272C/no unknown
- 1983-12-19 ES ES528157A patent/ES8506633A1/es not_active Expired
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- 1983-12-19 IL IL70477A patent/IL70477A/xx not_active IP Right Cessation
- 1983-12-19 PH PH30000A patent/PH20114A/en unknown
- 1983-12-19 NZ NZ206614A patent/NZ206614A/en unknown
- 1983-12-19 KR KR1019830006010A patent/KR860001921B1/ko active
- 1983-12-19 ZA ZA839381A patent/ZA839381B/xx unknown
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- 1983-12-20 AU AU22559/83A patent/AU546057B2/en not_active Ceased
- 1983-12-20 YU YU02468/83A patent/YU246883A/xx unknown
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- 1983-12-20 FI FI834692A patent/FI79104C/fi not_active IP Right Cessation
- 1983-12-20 SU SU833682597A patent/SU1296006A3/ru active
- 1983-12-20 DD DD83258248A patent/DD213920A5/de unknown
- 1983-12-20 DK DK586583A patent/DK586583A/da not_active Application Discontinuation
- 1983-12-20 GR GR73290A patent/GR81351B/el unknown
- 1983-12-21 JP JP58241806A patent/JPS59118782A/ja active Granted
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1984
- 1984-05-08 SU SU843739756A patent/SU1391499A3/ru active
- 1984-07-30 ES ES534723A patent/ES534723A0/es active Granted
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- 1985-11-11 YU YU01755/85A patent/YU175585A/xx unknown
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- 1986-02-14 US US06/830,384 patent/US4670449A/en not_active Expired - Lifetime
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