KR900018064A - 피라닐 시아노구아니딘 유도체 - Google Patents
피라닐 시아노구아니딘 유도체 Download PDFInfo
- Publication number
- KR900018064A KR900018064A KR1019900007840A KR900007840A KR900018064A KR 900018064 A KR900018064 A KR 900018064A KR 1019900007840 A KR1019900007840 A KR 1019900007840A KR 900007840 A KR900007840 A KR 900007840A KR 900018064 A KR900018064 A KR 900018064A
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- South Korea
- Prior art keywords
- compound
- cyano
- alkyl
- trans
- benzopyran
- Prior art date
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- PSUZFEOOWHGNNG-UHFFFAOYSA-N 1-cyano-1-(2h-pyran-2-yl)guanidine Chemical class NC(=N)N(C#N)C1OC=CC=C1 PSUZFEOOWHGNNG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 63
- 125000000217 alkyl group Chemical group 0.000 claims 28
- 229910052739 hydrogen Inorganic materials 0.000 claims 23
- 239000001257 hydrogen Substances 0.000 claims 23
- 150000002431 hydrogen Chemical class 0.000 claims 18
- -1 Pyranyl cyanoguanidine derivative compound Chemical class 0.000 claims 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- MYOPMNPRQGVXDQ-MSOLQXFVSA-N 1-cyano-2-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-3-phenylguanidine Chemical compound N(/[C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)=C(/NC#N)NC1=CC=CC=C1 MYOPMNPRQGVXDQ-MSOLQXFVSA-N 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- SETYANBYAYCKCM-CABCVRRESA-N 1-cyano-3-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-2-(2-methoxyethyl)guanidine Chemical compound C1=C(C#N)C=C2[C@@H](NC(\NC#N)=N/CCOC)[C@H](O)C(C)(C)OC2=C1 SETYANBYAYCKCM-CABCVRRESA-N 0.000 claims 2
- AHAASCKCEGQFIO-KGLIPLIRSA-N 1-cyano-3-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-2-ethylguanidine Chemical compound C1=C(C#N)C=C2[C@@H](NC(\NC#N)=N/CC)[C@H](O)C(C)(C)OC2=C1 AHAASCKCEGQFIO-KGLIPLIRSA-N 0.000 claims 2
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- XOYZVGFXSLYSCF-CVEARBPZSA-N 1-cyano-2-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-3-(2-methylbutan-2-yl)guanidine Chemical compound C1=C(C#N)C=C2[C@@H](NC(/NC#N)=N/C(C)(C)CC)[C@H](O)C(C)(C)OC2=C1 XOYZVGFXSLYSCF-CVEARBPZSA-N 0.000 claims 1
- HDSGGODQOVEPBS-CABCVRRESA-N 1-cyano-2-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-3-propan-2-ylguanidine Chemical compound C1=C(C#N)C=C2[C@@H](NC(\NC#N)=N/C(C)C)[C@H](O)C(C)(C)OC2=C1 HDSGGODQOVEPBS-CABCVRRESA-N 0.000 claims 1
- KTWWUKLYXUDVNA-NEPJUHHUSA-N 1-cyano-2-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]guanidine Chemical compound C1=C(C#N)C=C2[C@@H](\N=C(\N)NC#N)[C@H](O)C(C)(C)OC2=C1 KTWWUKLYXUDVNA-NEPJUHHUSA-N 0.000 claims 1
- BPAZGLAROZJRQD-MOPGFXCFSA-N 1-cyano-2-[(3s,4r)-6-ethynyl-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-3-phenylguanidine Chemical compound N(/[C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#C)=C(/NC#N)NC1=CC=CC=C1 BPAZGLAROZJRQD-MOPGFXCFSA-N 0.000 claims 1
- WXYLVMSYXAQHBI-MSOLQXFVSA-N 1-cyano-3-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-2-(pyridin-3-ylmethyl)guanidine Chemical compound N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)C(NC#N)=NCC1=CC=CN=C1 WXYLVMSYXAQHBI-MSOLQXFVSA-N 0.000 claims 1
- GHBLOUSEXUGORM-CVEARBPZSA-N 1-cyano-3-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-2-[2-(dimethylamino)ethyl]guanidine Chemical compound C1=C(C#N)C=C2[C@@H](NC(\NC#N)=N/CCN(C)C)[C@H](O)C(C)(C)OC2=C1 GHBLOUSEXUGORM-CVEARBPZSA-N 0.000 claims 1
- ZGWBHTSVFICBRG-OLZOCXBDSA-N 1-cyano-3-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-2-methylguanidine Chemical compound C1=C(C#N)C=C2[C@@H](NC(/NC#N)=N/C)[C@H](O)C(C)(C)OC2=C1 ZGWBHTSVFICBRG-OLZOCXBDSA-N 0.000 claims 1
- KQAVXJSFLGZEQV-MOPGFXCFSA-N 2-benzyl-1-cyano-3-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]guanidine Chemical compound N(/[C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)=C(NC#N)\NCC1=CC=CC=C1 KQAVXJSFLGZEQV-MOPGFXCFSA-N 0.000 claims 1
- KJZVGXCHTXABSU-CVEARBPZSA-N 2-cyano-1-[(3s,4r)-3-hydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-c]pyridin-4-yl]-1-phenylguanidine Chemical compound N#CN=C(N)N([C@@H]1C2=CN=CC=C2OC([C@H]1O)(C)C)C1=CC=CC=C1 KJZVGXCHTXABSU-CVEARBPZSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- MGLPCSJEBIGEFC-CABCVRRESA-N [1-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-5,6-dihydro-4h-pyrimidin-2-yl]cyanamide Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)CCCNC1=NC#N MGLPCSJEBIGEFC-CABCVRRESA-N 0.000 claims 1
- 125000005251 aryl acyl group Chemical group 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
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 230000003213 activating effect Effects 0.000 abstract 1
- 230000002253 anti-ischaemic effect Effects 0.000 abstract 1
- 229940125692 cardiovascular agent Drugs 0.000 abstract 1
- 239000002327 cardiovascular agent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 108010083133 potassium channel protein I(sk) Proteins 0.000 abstract 1
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 abstract 1
Classifications
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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
- C07D405/02—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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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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
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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
- A61P9/10—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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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
- C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
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Abstract
내용 없음
Description
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Claims (36)
- 하기 일바식을 갖는 피라닐 시아노구아니딘 유도체 화합물.식 중, a,b 및 c는 모두 탄소원자이거나, 또는 a,b 및 c중의 하나는 질소 원자 또는 -NO- 이고, 나머지는 탄소 원자들이고,R2는 수소, 히드록시 또는이고, R3및 R4는 각각 독립적으로 수소, 알킬 또는 아릴알킬이거나, 또는 R3및 R4는 이들에 결합된 탄소 원자와 함께 5 내지 7원 카르보시클릭 고리를 형성하고, R5는 H, 알킬, 할로알킬, 알케닐, 알키닐, 시클로알킬, 아릴알킬, 시클로알킬알킬, -CN, NO2,-COR, -COOR, -CONHR,-CONR3,-CF3, S-알킬, -SO알킬,-SO2알킬,(O-알킬)2 , 할로겐, 아미노, 치환아미노, O-알킬, OCF3, OCH2CF3, OCO알킬, -OCONR 알킬, -NRCO알킬 및 NRCOO알킬, NRCONR2(상기 기들 중에서, R은 수소, 알킬, 아릴, 아릴알킬, 시클로알킬, 또는 (시클로알킬)알킬기임)중에서 선택되고, R6는 H, 알킬, OH, O-알킬, 아미노, 치환 아미노, CN, 및 NO2중에서 선택되고, R7과 R8은 각각 독립적으로 수소, 알킬, 알케닐, 아릴, 헤테로시클로, (헤테로시클로)알킬, 아릴알킬, 시클로알킬 및 (시클로알킬)알킬, 치환 알킬기(여기서, 치환체는 알콕시, 알킬티오, 및 치환 아미노를 포함함)중에서 선택되거나, 또는 R7및 R8은 이들에 결합된 질소원자와 함게 1-피롤리디닐, 1-피페리디닐, 1-아제피닐, 4-모르폴리닐, 4-티아모르필리닐, 1-피페라지닐, 4-알킬-1-피페라지닐 또는 4-아릴알킬-1-페페라지닐기를 형성할 수 있고, 여기서, 이와 같이 형성된 기들은 각각 알킬, 알콕시, 알킬티오, 할로겐 또는 트리플루오로메틸기로 치환될 수 있으며, R9와 R10은 수소, 알킬, 알케닐, 아릴, 알릴알킬, 시클로알킬 또는 시클로 알킬알킬 중에서 선택되고, n은 1,2 또는 3이다.
- 1항에 있어서 다음과 같이 정의되는 화합물, 즉 a는 질소 원자 또는 -CR5이고, b 및 c는 각각 -CH-이고,R2는 히드록시 또는 -OCO알킬이고, R3및 R4각각은 알킬이고, R5는 전자를 끄는 기이고, R6는 수소, 알킬, O-알킬, 아미노이고, R7은 수소, 알킬, 아릴 또는 아릴알킬이고, R8은 수소이고, R9는 수소 또는 알킬이고, R10은 수소이고, n은 1 또는 2이다.
- 1항에 있어서 다음과 같이 정의되는 화합물, 즉, a는 질소 원자 또는 -CR5이고, b 및 c는 각각 -CH- 이고, R2는 트란스히드록시이고, R3및 R4는 각각 메틸이고, R5는 -CN 또는 -NO2이고, R6는 수소이고, R7은 수소, 메틸, 에틸, 페틸 또는 페닐메틸이고, R8는 수소이고, R9는 수소이고, R10은 수소이고, n은 1이다.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(1,1-디메틸프로필)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-에틸구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-페닐구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-에틸구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-3,4-디히드로-3-히드록시-2,2-디메틸-4-[2-(시아노이미노-1-피롤리디닐]-2H-1-벤조피란-6-카르보니트릴인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(3,4-디히드로-3-히드록시-2,2-디메틸-2H-피라노[3,2-c]피리딘-4-일)-페닐구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드로시-2,2-디메틸-2H-1-벤조피란-4-일)-1-피롤리딘-카르복스이미다미드인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드로시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-에틸-N-메틸구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-[2(디메틸아미노)에틸]구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-4[[(시아노이미노)(1-피롤리디닐)-메틸]아미노]-3,4-디히드록시-2,2-디메틸-2H-1-벤조피란-6-카르보니트릴인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-메틸구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-4[(시아노이미노)[[4-(페닐메틸)-1-피페라지닐]메틸]아미노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-6-카르보니트릴인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(메틸에틸)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-디메틸구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-페닐메틸구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-[2-[(페틸메틸)메틸아미노]에틸]구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(2-메록시에틸)구아니딘인 화합물.
- 제1항에있어서, 화합물이 (3S-트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-페닐구아니딘인 화합물.
- 제1항에있어서, 화합물이 (3S-트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-페닐구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-4-[2-(시아노이미노)테트라히드로-1-(2H)-피리미디닐]-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-6-카르보니트릴인 화합물.
- 제1항에 있어서, 하기 구조식을 갖는 화합물.
- 제1항에 정의한 바와 같은 화합물의 치료학적으로 유효한 양을 치료를 요하는 포유류 동물종에 투여함을 특징으로 하는 심근성 허혈증의 치료 방법.
- 제26항에 있어서, 상기 호합물에 있어서, R7이 아릴 및 아릴아킬중에서 선택되고, R8및 R9이 각각 수소인 방법.
- 제26항에 있어서, 상기 화합물이 하기 구조식을 갖는 방법.
- 제1항의 화합물의 치료학적으로 유효한 양을 치료를 요하는 포유류 동물종에 투여함을 특징으로 하는 고혈압 치료의 방법.
- 제29항에 있어서, 상기 화합물에서 R7이 수소 및 1 내지 3개의 탄소 원자를 갖는 알킬기 중에서 선택되거나, 또는 R7및 R8이 함께 피롤리딘 또는 피페리딘을 형성하고, R9및 R10이 각각 수소이고, n이 1 또는 2인 방법.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(2-메톡시에틸)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(4-피리디메틸)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(3-피리디닐메틸)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(6-에티닐-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-페닐구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N″-시아노-N-(3,4-디히드로-6-(페닐에티닐)-2H-1-벤조피란-4-일)-N'-페닐구아니딘인 화합물.
- 하기 일반식을 갖는 피라닐 시아노구아니딘 유도체 화합물.식 중, a, b 및 c는 모두 탄소 원자이거나, 또는 a, b 및 c중 하나는 질소 원자 또는 -NO- 이고, 나머지는 탄소 원자들이고,R2는 수소, 히드록시,이고, R3및 R4는 각각 독립적으로 수소, 알킬 또는 아릴알킬이거나, 또는 R3및 R4는 이들에 결합된 탄소 원자와 함께 5 내지 7원 카르보시클릭 고리를 형성하고, R5는 H, 알킬, 할로알킬, 알케닐, 알키닐, 시클로알킬, 아릴알킬, 시클로알킬알킬, -CN, -NO2, -COOR, -CONHR, -CONR2, -CF3, S-알킬, -SO알킬, -SO2알킬, 할로겐, 아미노, 치환된 아미노 O-알킬, OCF3, OCH2CF3, OCO알킬, -OCONR 알킬, -NRCO알킬 및 NRCOO알킬, NRCONR2(여기서, 상기 기들 중에서, R은 수소, 알킬, 아릴, 아릴알킬, 시클로알킬, 또는 시클로알킬알킬기일 수 있음)중에서 선택되고, R6는 H, 알킬, OH, O-알킬, 아미노, 치환 아미노, CN, 및 NO2중에서 선택되고, R7과 R8은 각각 독립적으로 수소, 알킬, 알케닐, 아릴, 아릴알킬, 헤테로시클로, 시클로알킬 및 시클로알킬알킬중에서 선택되거나, 또는 R7및 R8은 이들에 결합된 질소원자와 함게 1-피롤리디닐, 1-피페리디닐, 1-아제피닐, 4-모르폴리닐, 4-티아모르필리닐, 1-피페라지닐, 4-알킬-1-피페라지닐 또는 4-아릴알킬-1-페페라지닐기를 형성할 수 있고, 여기서, 이와 같이 형성된 기들은 각각 알킬, 알콕시, 알킬티오, 할로겐 또는 트리플루오로메틸기로 치환될 수 있으며, R9와 R10은 수소, 알킬,알케닐, 아릴, 알릴알킬, 시클로알킬 또는 시클로알킬알킬기 중에서 선택되고; n은 1,2 또는 3이다.※ 참고사항 : 최초출원내용에 의하여 공개하는 것임.
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US49306090A | 1990-03-13 | 1990-03-13 | |
US493,060 | 1990-03-13 | ||
US493060 | 1990-03-13 |
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HU (1) | HU207857B (ko) |
IE (1) | IE901793A1 (ko) |
IL (1) | IL94326A (ko) |
NO (1) | NO174807B (ko) |
NZ (1) | NZ233845A (ko) |
PL (4) | PL166192B1 (ko) |
PT (1) | PT94210B (ko) |
RU (1) | RU2057129C1 (ko) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ231969A (en) * | 1988-12-23 | 1992-09-25 | Beecham Group Plc | Benzopyran derivatives, analogues, precursors, and medicaments |
US5104890A (en) * | 1989-03-28 | 1992-04-14 | Fujisawa Pharmaceutical Company, Ltd. | Benzopyran derivatives and processes for preparation thereof |
US5140031A (en) * | 1989-05-31 | 1992-08-18 | E. R. Squibb & Sons, Inc. | Pyranyl cyanoguanidine derivatives |
CA2015296C (en) * | 1989-05-31 | 2001-08-07 | Karnail Atwal | Pyranyl cyanoguanidine derivatives |
FR2657872B2 (fr) * | 1989-11-06 | 1992-06-12 | Sanofi Sa | Derive d'amidino-4 chromanne, procede d'obtention et compositions pharmaceutiques le contenant. |
RU2102547C1 (ru) * | 1990-05-17 | 1998-01-20 | Юнион Кемп Корпорейшн | Способ получения отбеленной целлюлозной массы и способ делигнификации и отбелки лигноцеллюлозного материала (варианты) |
AU651105B2 (en) * | 1990-06-18 | 1994-07-14 | E.R. Squibb & Sons, Inc. | Benzopyran derivatives and heterocyclic analogs thereof as antiischemic agents |
US5643921A (en) * | 1990-09-26 | 1997-07-01 | E.R. Squibb & Sons, Inc. | Cardiopulmonary bypass and organ transplant using a potassium channel activator |
CA2055376A1 (en) * | 1990-12-05 | 1992-06-06 | Gary J. Grover | Method of treating shock using a potassium channel activator |
DE4120322A1 (de) * | 1991-06-20 | 1992-12-24 | Bayer Ag | Aminomethyl-substituierte 2,3-dihydropyrano(2,3-b)pyridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
US5374643A (en) * | 1992-09-11 | 1994-12-20 | E. R. Squibb & Sons, Inc. | Aryl urea (thiourea) and cyanoguanidine derivatives |
IL109229A0 (en) * | 1993-05-11 | 1994-07-31 | Bristol Myers Squibb Co | Heterocyclic compounds and processes for the preparation of pyranyl cyanoguanidine derivatives using the same |
US5478734A (en) * | 1993-06-18 | 1995-12-26 | Bristol-Myers Squibb Company | Method of chiral epoxidation of benzopyran or pyranopyridine derivatives using microorganisms |
US5869478A (en) * | 1995-06-07 | 1999-02-09 | Bristol-Myers Squibb Company | Sulfonamido substituted benzopyran derivatives |
US5612323A (en) * | 1995-06-07 | 1997-03-18 | Bristol-Myers Squibb Company | Phosphinic ester substituted benzopyran derivatives |
US5612370A (en) * | 1995-06-07 | 1997-03-18 | Bristol-Myers Squibb Company | Phenylglycine and phenylalaninen amido benzopyran derivatives |
US5629429A (en) * | 1995-06-07 | 1997-05-13 | Bristol-Myers Squibb Company | Process for preparing 4-arylamino-benzopyran and related compounds |
KR100429609B1 (ko) * | 1999-10-21 | 2004-05-03 | 동부한농화학 주식회사 | 벤조피라닐 구아니딘 유도체, 그의 제조방법 및 그를포함하는 약학적 조성물 |
CN1229371C (zh) * | 1999-10-21 | 2005-11-30 | 东部韩农化学株式会社 | 苯并吡喃胍衍生物,其制备方法,及其药物组合物 |
CN1854135B (zh) * | 2005-04-18 | 2013-06-12 | 李伟章 | 由氰基胍连接组成的杂环化合物及其医药应用 |
WO2007022964A2 (de) | 2005-08-24 | 2007-03-01 | Abbott Gmbh & Co. Kg | Hetaryl substituierte guanidinverbindungen und ihre verwendung als bindungspartner für 5-ht5-rezeptoren |
JP5647227B2 (ja) * | 2009-04-23 | 2014-12-24 | ピラマル イメージング ソシエテ アノニム | F−18ラベルされたpetトレーサーのための新規前駆体分子 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3682331D1 (de) * | 1985-06-08 | 1991-12-12 | Beecham Group Plc | Pyrano(3,2-c)pyridinderivate, verfahren und zwischenprodukte zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen. |
GB8521857D0 (en) * | 1985-09-03 | 1985-10-09 | Beecham Group Plc | Active compounds |
JPH027217A (ja) * | 1988-04-30 | 1990-01-11 | Mitsubishi Electric Corp | 磁気記録再生装置 |
US4988723A (en) * | 1988-06-02 | 1991-01-29 | Fujisawa Pharmaceutical Co., Ltd. | Benzopyran derivatives and their use as anti-hypertensives |
DE3823533A1 (de) * | 1988-07-12 | 1990-02-08 | Beiersdorf Ag | Substituierte 4-heterocyclyl-2h-benzo(b)pyrane, verfahren und 4-hydroxy-3-brom-, 3,4-oxiranyl-3,4-dehydro-2h-benzo(b)pyrane als zwischenprodukte zu ihrer herstellung, sowie sie enthaltende pharmazeutsche praeparate |
EP0359537B1 (en) * | 1988-09-16 | 1996-06-26 | Beecham Group Plc | Benzopyran derivatives with antihypertensive activity |
JPH02172984A (ja) * | 1988-12-23 | 1990-07-04 | Yamanouchi Pharmaceut Co Ltd | クロマン誘導体 |
US5104890A (en) * | 1989-03-28 | 1992-04-14 | Fujisawa Pharmaceutical Company, Ltd. | Benzopyran derivatives and processes for preparation thereof |
CA2015296C (en) * | 1989-05-31 | 2001-08-07 | Karnail Atwal | Pyranyl cyanoguanidine derivatives |
-
1990
- 1990-04-24 CA CA002015296A patent/CA2015296C/en not_active Expired - Lifetime
- 1990-04-30 AU AU54552/90A patent/AU633082B2/en not_active Ceased
- 1990-05-08 IL IL9432690A patent/IL94326A/xx not_active IP Right Cessation
- 1990-05-18 IE IE179390A patent/IE901793A1/en unknown
- 1990-05-29 NZ NZ233845A patent/NZ233845A/en unknown
- 1990-05-30 NO NO902394A patent/NO174807B/no not_active IP Right Cessation
- 1990-05-30 KR KR1019900007840A patent/KR950006155B1/ko not_active IP Right Cessation
- 1990-05-30 HU HU903271A patent/HU207857B/hu not_active IP Right Cessation
- 1990-05-30 JP JP2143243A patent/JPH0327375A/ja active Pending
- 1990-05-30 EG EG31990A patent/EG19389A/xx active
- 1990-05-30 PT PT94210A patent/PT94210B/pt not_active IP Right Cessation
- 1990-05-30 RU SU904830194A patent/RU2057129C1/ru not_active IP Right Cessation
- 1990-05-31 DE DE69028143T patent/DE69028143T2/de not_active Expired - Fee Related
- 1990-05-31 ES ES90305920T patent/ES2090099T3/es not_active Expired - Lifetime
- 1990-05-31 PL PL90290037A patent/PL166192B1/pl not_active IP Right Cessation
- 1990-05-31 DK DK90305920.2T patent/DK0401010T3/da active
- 1990-05-31 EP EP90305920A patent/EP0401010B1/en not_active Expired - Lifetime
- 1990-05-31 PL PL90290036A patent/PL166230B1/pl not_active IP Right Cessation
- 1990-05-31 PL PL90290035A patent/PL166174B1/pl not_active IP Right Cessation
- 1990-05-31 AT AT90305920T patent/ATE141598T1/de not_active IP Right Cessation
- 1990-05-31 PL PL90285415A patent/PL166007B1/pl not_active IP Right Cessation
- 1990-05-31 CN CN90103959A patent/CN1047672A/zh active Pending
- 1990-05-31 FI FI902710A patent/FI109120B/fi active IP Right Grant
-
1991
- 1991-06-28 JP JP3158327A patent/JPH05239049A/ja active Pending
-
1996
- 1996-11-19 GR GR960403095T patent/GR3021702T3/el unknown
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1997
- 1997-02-13 HK HK16997A patent/HK16997A/xx not_active IP Right Cessation
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