KR920016437A - 피라닐 시아노구아니딘 유도체 - Google Patents
피라닐 시아노구아니딘 유도체 Download PDFInfo
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- KR920016437A KR920016437A KR1019920002992A KR920002992A KR920016437A KR 920016437 A KR920016437 A KR 920016437A KR 1019920002992 A KR1019920002992 A KR 1019920002992A KR 920002992 A KR920002992 A KR 920002992A KR 920016437 A KR920016437 A KR 920016437A
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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 50
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 150000002431 hydrogen Chemical class 0.000 claims 15
- -1 Pyranyl cyanoguanidine derivative compound Chemical class 0.000 claims 10
- 238000001356 surgical procedure Methods 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 210000000056 organ Anatomy 0.000 claims 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 3
- 150000001718 carbodiimides Chemical class 0.000 claims 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 230000007774 longterm Effects 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 230000001681 protective effect Effects 0.000 claims 3
- WSTVFISGQNVURZ-MSOLQXFVSA-N 1-cyano-2-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-3-(4-nitrophenyl)guanidine Chemical compound N(/[C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)=C(/NC#N)NC1=CC=C([N+]([O-])=O)C=C1 WSTVFISGQNVURZ-MSOLQXFVSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 230000000747 cardiac effect Effects 0.000 claims 2
- 230000002612 cardiopulmonary effect Effects 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- VDFWRFMIKTZCNI-MSOLQXFVSA-N 1-(2-chlorophenyl)-2-cyano-1-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]guanidine Chemical compound N#CN=C(N)N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)C1=CC=CC=C1Cl VDFWRFMIKTZCNI-MSOLQXFVSA-N 0.000 claims 1
- BSYCDISSXFZGNT-MSOLQXFVSA-N 1-(3-chlorophenyl)-2-cyano-1-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]guanidine Chemical compound N#CN=C(N)N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)C1=CC=CC(Cl)=C1 BSYCDISSXFZGNT-MSOLQXFVSA-N 0.000 claims 1
- SADDEOBQPPLBOL-MSOLQXFVSA-N 1-(3-chlorophenyl)-3-cyano-2-[(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)NC1=CC=CC(Cl)=C1 SADDEOBQPPLBOL-MSOLQXFVSA-N 0.000 claims 1
- QJHIQUZWCIFSBC-MSOLQXFVSA-N 1-(4-chlorophenyl)-2-cyano-1-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]guanidine Chemical compound N#CN=C(N)N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)C1=CC=C(Cl)C=C1 QJHIQUZWCIFSBC-MSOLQXFVSA-N 0.000 claims 1
- VLICJSLDCJXZBG-MSOLQXFVSA-N 1-(4-chlorophenyl)-3-cyano-2-[(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)NC1=CC=C(Cl)C=C1 VLICJSLDCJXZBG-MSOLQXFVSA-N 0.000 claims 1
- YSILOOFFUQERDH-MOPGFXCFSA-N 1-cyano-2-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-3-(4-cyanophenyl)guanidine Chemical compound N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)=C(NC#N)NC1=CC=C(C#N)C=C1 YSILOOFFUQERDH-MOPGFXCFSA-N 0.000 claims 1
- OQAVHGBHFXVEDL-MSOLQXFVSA-N 1-cyano-2-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-3-(4-fluorophenyl)guanidine Chemical compound N(/[C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)=C(/NC#N)NC1=CC=C(F)C=C1 OQAVHGBHFXVEDL-MSOLQXFVSA-N 0.000 claims 1
- LQVLAJMHIRBVAF-MSOLQXFVSA-N 1-cyano-2-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-3-(4-hydroxyphenyl)guanidine Chemical compound N(/[C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)=C(/NC#N)NC1=CC=C(O)C=C1 LQVLAJMHIRBVAF-MSOLQXFVSA-N 0.000 claims 1
- APPZRPVFEIBKLL-MOPGFXCFSA-N 1-cyano-2-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-3-(4-methoxyphenyl)guanidine Chemical compound C1=CC(OC)=CC=C1N\C(NC#N)=N\[C@@H]1C2=CC(C#N)=CC=C2OC(C)(C)[C@H]1O APPZRPVFEIBKLL-MOPGFXCFSA-N 0.000 claims 1
- WUFYBMWGXAFMLY-RPBOFIJWSA-N 1-cyano-2-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-3-(4-phenylmethoxyphenyl)guanidine Chemical compound N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)=C(NC#N)NC(C=C1)=CC=C1OCC1=CC=CC=C1 WUFYBMWGXAFMLY-RPBOFIJWSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- GIKZWZCAJXUXFT-MSOLQXFVSA-N 2-cyano-1-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-1-(4-fluorophenyl)guanidine Chemical compound N#CN=C(N)N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)C1=CC=C(F)C=C1 GIKZWZCAJXUXFT-MSOLQXFVSA-N 0.000 claims 1
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical group Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000008148 cardioplegic solution Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 230000010412 perfusion Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 230000002253 anti-ischaemic effect Effects 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
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
-
- 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
- C07D405/06—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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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- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrane Compounds (AREA)
- Medicinal Preparation (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (34)
- 하기 일반식을 갖는 피라닐 시아노구아니딘 유도체 화합물.식 중, R1및 R7은 각각 독립적으로 수소, 시아노, 알콕시, 니트로, 할로 히드록시, 할로알킬, 벤질옥시이되, 단, R1및 R7중 적어도 하나는 수소가 아니고, R2는 수소, 히드록시 또는이고, R3및 R4는 각각 독립적으로 수소, 알킬 또는 아릴알킬이거나, 또는 R3및 R4는 이들이 결합된 탄소원자와 함께 5 내지 7원 카르보시클릭고리를 형성하고, R5는 H, 알킬, 할로알킬, 알케닐, 알키닐, 시크롤알킬, 아릴알킬, 시클로알킬알킬, -DN, -NO2, -COR, -COOR, -CONHR2, -CF3, S-알킬, -SO-알킬, -SO2알킬,,할로겐, 아미노, 치환 아미노, O-알킬, OCF2, OCH2CF3, -OCO알킬, -OCONR알킬, -NRCO알킬 및 NRCOO알킬, NRCONR2(상기 기들 중에서, R은 수소, 알킬, 할로알킬, 아릴, 아릴알킬, 시클로알킬, 또는 (시클로알킬)알킬기임)중에서 선택되고, R6는 H, 알킬, OH, O-알킬, 아미노, 치환 아미노, NHCOR(여기서, R은 상기한 바와 같음), CN, 및 NO2중에서 선택되고, R8은 수소, 알킬 중에서 선택되고, R9는 수소, 알킬, 알케닐, 아릴, 알릴알킬, 시클로알킬 또는 시클로알킬알킬중에서 선택되고, n은 1,2 또는 3이다.
- 제1항에 있어서, R1은 클로로 또는 플루오로이고, R2는 트란스-히드록시이고, R3및 R4는 각각 메틸이고, R5는 -CN 또는 -NO2이고, R6는 수소이고, R7은 수소이고, R8은 수소이고, R9는 수소인 화합물.
- 제1항에 있어서, 하기 일반식을 갖는 화합물.식 중, R1은 플루오로 또는 클로로이다.
- 제1항에 있어서, 화합물이 (트란스)-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(4-시아노 페닐)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-메톡시 페닐)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-니트로 페닐)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (트란스)-N-(4-클로로페닐)-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-(2-클로로페닐)-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-(3-클로로페닐)-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-(4-플루오로페닐)-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (3S-트란스)-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(4-플루오로페닐)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (3S-트란스)-N-(4-클로로페닐)-N"-시아노-N'-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (3S-트란스)-N-(3-클로로페닐)-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'-(4-(페닐 메톡시)페닐)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-히드록시페닐)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (3S-트란스)-N-(3,4-디클로로페닐)-N"-시아노-N'-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (3S-트란스)-N"-시아노-N'-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(4-트리플루오로메틸)페닐구아니딘인 화합물.
- 하기 일반식(Ⅱ)의 화합물을 카르보디이미드 존재하에 하기 일반식(Ⅲ)의 화합물과 커플링시키는 것으로 이루어지는 하기 일반식(Ⅰ)의 화합물의 제조방법.식 중, R1및 R7은 각각 독립적으로 수소, 시아노, 알콕시, 니트로, 할로 히드록시, 할로알킬, 벤질옥시이되, 단, R1및 R7중 적어도 하나는 수소가 아니고, R2는 수소, 히드록시 또는이고, R3및 R4는 각각 독립적으로 수소, 알킬 또는 아릴알킬이거나, 또는 R3및 R4는 이들이 결합된 탄소원자와 함께 5 내지 7원 카브보시클릭 고리를 형성하고, R5는 H, 알킬, 할로알킬, 알케닐, 알키닐, 시클로알킬, 아릴알킬, 시클로알킬알킬, -CN, -NO2, -COR, -COOR, -CONHR, -CONR2, -CF3, S-알킬, -SO-알킬, -SO2알킬,,할로겐, 아미노, 치환 아미노, O-알킬, OCF2, OCH2CF3, -OCO알킬, -OCONR알킬, -NRCO알킬 및 NRCOO알킬, NRCONR2(상기 기들 중에서, R은 수소, 알킬, 할로알킬, 아릴, 아릴알킬, 시클로알킬, 또는 (시클로알킬)알킬기임)중에서 선택되고, R6는 H, 알킬, -OH, O-알킬, 아미노, 치환 아미노, NHCOR(여기서, R은 상기한 바와 같음), CN, 및 NO2중에서 선택되고, R8은 수소, 알킬 중에서 선택되고, R9는 수소, 알킬, 알케닐, 아릴, 알릴알킬, 시클로알킬 또는 시클로알킬알킬중에서 선택되고, n은 1,2 또는 3이다.
- 제18항에 있어서, 상기 카르보디이미드가 하기 일반식을 갖는 방법.식중, X는 할로겐이고, Ra, Rb및 Rc는 독립적으로 알킬, 시클로알킬, 페닐, 페닐알킬, 시클로알킬알킬이거나, 또는 Ra 및 Rb가 N-원자와 함께 1-피롤리디닐, 1-피페리디닐, 4-모르폴리닐, 4-티오모르폴리닐, 4-알킬-1-피레라지닐 또는 4-페닐알킬-1-피페라지닐을 형성한다.
- 제18항에 있어서, 상기 카르보디이미드가 1-(3-디메틸아미노 프로필)-3-에틸-카르보디이미드 염산염인 방법.
- 제1항에 있어서, 화합물이 (3S-트란스)-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2디메틸-2H-1-벤조피란-4-일)-N'-(4-니트로페닐)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (3S-트란스)-N-(3니트로페닐)-N"-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸2H-1-벤조피란-4-일)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (3S-트란스)-N-(3-트리플루오로메닐페닐)-N"-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (3S-트란스)-N'-시노아-N-6(-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(3-메틸페닐)구아니딘인 화합물.
- 제1항에 있어서, 화합물이 (3S-트란스)-N"-N"-시아노-N'-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(4-메틸페닐)구아니딘인 화합물.
- 장기 보호량의 제1항의 화합물로 이루어진, 장기 외과 수술을 받는 포유동물의 허혈성 손상으로부터 장기를 보호하기 위한 제약 조성물.
- 제26항에 있어서, 상기 수술이 심폐의 보조관(bypass)수술인 조성물.
- 제26항에 있어서, 상기 수술이 장기 이식 수술인 조성물.
- 제28항에 있어서, 사기 수술이 심장 이식 수술인 조성물.
- 제26항에 있어서, 상기 화합물을 장기 기능을 보존, 보호 또는 유지하기 위하여 상기 수술에 사용되는 용액에 첨가한 조성물.
- 제30항에 있어서, 심장 보호량의 상기 화합물을 심폐의 보조관 또는 심장 이식 수술에 관련된 심장을 정지, 관류, 저장 및(또는)보호하는데 사용되는 심장마비(cadioplegic)용액에 첨가한 조성물.
- 제26항에 있어서, 상기 화합물을 상기 수술 이전 및(또는)도중 및(또는)이후에 장기 외과 수술을 받는 포유동물종에 투여하기 위한 조성물.
- 제28 또는 29항에 있어서, 상기 화합물을 상기 장기를 장기 기증자로부터 제거하기 이전 및(또는) 도중 및(또는) 이후에 장기 수용자에게 투여하기 위한 조성물.
- 심장 보호량의 제1항의 화합물 및 적당한 담체를 함유하는 심장 마비 용액.※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/661,763 US5140031A (en) | 1989-05-31 | 1991-02-27 | Pyranyl cyanoguanidine derivatives |
US661,763 | 1991-02-27 |
Publications (1)
Publication Number | Publication Date |
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KR920016437A true KR920016437A (ko) | 1992-09-24 |
Family
ID=24655020
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Application Number | Title | Priority Date | Filing Date |
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KR1019920002992A KR920016437A (ko) | 1991-02-27 | 1992-02-26 | 피라닐 시아노구아니딘 유도체 |
Country Status (19)
Country | Link |
---|---|
US (1) | US5140031A (ko) |
EP (1) | EP0501797B1 (ko) |
KR (1) | KR920016437A (ko) |
CN (1) | CN1035253C (ko) |
AT (1) | ATE138919T1 (ko) |
AU (1) | AU650512B2 (ko) |
CA (1) | CA2061699C (ko) |
CY (1) | CY1952A (ko) |
DE (1) | DE69211182T2 (ko) |
DK (1) | DK0501797T3 (ko) |
ES (1) | ES2088537T3 (ko) |
GR (1) | GR3020647T3 (ko) |
HK (1) | HK161396A (ko) |
IE (1) | IE920346A1 (ko) |
IL (1) | IL101012A0 (ko) |
MX (1) | MX9200817A (ko) |
NO (1) | NO180679C (ko) |
TW (1) | TW201741B (ko) |
ZA (1) | ZA921333B (ko) |
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-
1991
- 1991-02-27 US US07/661,763 patent/US5140031A/en not_active Expired - Lifetime
-
1992
- 1992-02-01 TW TW081100798A patent/TW201741B/zh active
- 1992-02-19 IL IL101012A patent/IL101012A0/xx unknown
- 1992-02-24 IE IE034692A patent/IE920346A1/en not_active Application Discontinuation
- 1992-02-24 AU AU11147/92A patent/AU650512B2/en not_active Ceased
- 1992-02-24 CA CA002061699A patent/CA2061699C/en not_active Expired - Fee Related
- 1992-02-24 ZA ZA921333A patent/ZA921333B/xx unknown
- 1992-02-26 NO NO920767A patent/NO180679C/no unknown
- 1992-02-26 MX MX9200817A patent/MX9200817A/es not_active IP Right Cessation
- 1992-02-26 KR KR1019920002992A patent/KR920016437A/ko active IP Right Grant
- 1992-02-27 EP EP92301654A patent/EP0501797B1/en not_active Expired - Lifetime
- 1992-02-27 CN CN92101340A patent/CN1035253C/zh not_active Expired - Fee Related
- 1992-02-27 AT AT92301654T patent/ATE138919T1/de not_active IP Right Cessation
- 1992-02-27 DK DK92301654.7T patent/DK0501797T3/da active
- 1992-02-27 DE DE69211182T patent/DE69211182T2/de not_active Expired - Fee Related
- 1992-02-27 ES ES92301654T patent/ES2088537T3/es not_active Expired - Lifetime
-
1996
- 1996-07-29 GR GR960402003T patent/GR3020647T3/el unknown
- 1996-08-29 HK HK161396A patent/HK161396A/xx not_active IP Right Cessation
-
1997
- 1997-05-16 CY CY195297A patent/CY1952A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
HK161396A (en) | 1996-09-06 |
GR3020647T3 (en) | 1996-10-31 |
AU650512B2 (en) | 1994-06-23 |
NO920767D0 (no) | 1992-02-26 |
NO180679B (no) | 1997-02-17 |
EP0501797A1 (en) | 1992-09-02 |
DE69211182T2 (de) | 1997-01-23 |
EP0501797B1 (en) | 1996-06-05 |
DK0501797T3 (da) | 1996-06-24 |
CY1952A (en) | 1997-05-16 |
CN1035253C (zh) | 1997-06-25 |
ATE138919T1 (de) | 1996-06-15 |
ZA921333B (en) | 1992-11-25 |
CA2061699C (en) | 2002-05-21 |
US5140031A (en) | 1992-08-18 |
NO920767L (no) | 1992-08-28 |
AU1114792A (en) | 1992-09-03 |
CA2061699A1 (en) | 1992-08-28 |
IE920346A1 (en) | 1992-09-09 |
TW201741B (ko) | 1993-03-11 |
MX9200817A (es) | 1992-08-01 |
CN1064272A (zh) | 1992-09-09 |
NO180679C (no) | 1997-05-28 |
ES2088537T3 (es) | 1996-08-16 |
IL101012A0 (en) | 1992-11-15 |
DE69211182D1 (de) | 1996-07-11 |
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