KR860000292A - 벤조푸란유도체의 제조방법 - Google Patents
벤조푸란유도체의 제조방법 Download PDFInfo
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- KR860000292A KR860000292A KR1019850004373A KR850004373A KR860000292A KR 860000292 A KR860000292 A KR 860000292A KR 1019850004373 A KR1019850004373 A KR 1019850004373A KR 850004373 A KR850004373 A KR 850004373A KR 860000292 A KR860000292 A KR 860000292A
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- Prior art keywords
- alkyl
- independently
- compound
- hydrogen
- het
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- 238000004519 manufacturing process Methods 0.000 title claims 4
- 150000001907 coumarones Chemical class 0.000 title abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 13
- 150000001875 compounds Chemical class 0.000 claims abstract 11
- 150000002431 hydrogen Chemical class 0.000 claims abstract 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims abstract 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims abstract 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 150000003536 tetrazoles Chemical class 0.000 claims abstract 2
- 229930192474 thiophene Natural products 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- -1 parazin Chemical compound 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 231100000331 toxic Toxicity 0.000 claims 2
- 230000002588 toxic effect Effects 0.000 claims 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000003855 acyl compounds Chemical class 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- 206010027654 Allergic conditions Diseases 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000001120 cytoprotective effect Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 150000002617 leukotrienes Chemical class 0.000 abstract 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D407/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
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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
- C07D405/06—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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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07—ORGANIC CHEMISTRY
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- C07D417/00—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
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
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- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- 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
- C07F9/65515—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 five-membered ring
- C07F9/65517—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 five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Animal Behavior & Ethology (AREA)
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- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- 일반식(Ⅶ)의 화합물을 탈카복실화하여, 일반식(Ⅷ)의 화합물(즉, R2가 H인 일반식(Ⅰ)의 화합물)을 제조하거나, 계속해서 생성된 일반식(Ⅷ)의 화합물을 일반식(Ⅸ)의 산할라이드와 반응시켜 일반식(Ⅹ)의 아실화합물을 수득한 후, 일반식(Ⅹ)의 아실을 환원시킴을 특징으로 하여, 일반식(Ⅰ)의 화합물 및 그의 약제학적으로 무독한 염을 제조하는 방법.(Ⅰ) (Ⅱ)(Ⅷ) R6-COCl (Ⅸ)(Ⅹ)상기식에서, R1은 각가 독립적으로 수소 또는 C1-C6알킬이며, R2는 수소, C1-C6알킬, -(CH2)n-Het-Y 또는 -(CH2)n이고;R3는 하이드록실,, OCCCH2CH2COOH, OSO3H 또는 OPO3H2이며;R4는 각각 독립적으로 C1-C6알킬이고;R5는 각각 독립적으로 수소, C1-C6알킬이거나, 두개의 R5는 그들이 부착되어 있는 질소 원자와 함께 결합하여 5- 또는 6- 원환을 형성하고;R6는 C1-C5알킬, (CH2)n-1Het-Y 또는 -(CH2)n-1phY2Y3Y4이며;Het는 피리딘, 파라진, 피리미딘, 옥사졸, 피라졸, 옥사디아조르 테트라졸, 퀴놀린, 티오펜, 푸란, 피롤티아졸, 티아디아졸 및 이미다졸 중에서 선택된 페테로사이클릭 그룹이고;X는 산소, 황, SO 또는 SO2이며,Y,Y1,Y2,Y3,Y4및 Z는 각가 독립적으로 수소, 할로겐, OH, C|1-C5알킬, C2-C5알케닐, -COOR1, -COR1, 니트로, C1-C5알콕시, C1-C5알킬티오, -CH2SR1, OCH2CO2R1, -CON, -SCF,-SO2N, -CN, -CF31또는 -NR5R5이고; 각각 독립적으로 0내지 10이며;단, R1,R2,Y,Y1,Y2,Y3,Y4및 Z가 모두 동시에 수소이어서는 안되고; R1,R2,Y,Y1및 Z중 2개까지가 C1-C2알킬이며, 그중 나머지가 수소이면 R3는 OH가아니며;그룹에서 n이 0이고, R3,Y,Y1및 Z중 하나가 OH이면, R1은 수소 또는 C1-C2알킬이 아니다.
- 제1항에 있어서, R1이 각각 C1-C3알킬이며;R2가 수소, C1-C3알킬,또는 (CH2)nHet-Y 이고;R3하이드록실, O--R1,O--OR4, OCOCH2CH2COOH, OSO3H, 또는 OPO3H2이며;R4가 각각 독립적으로 C1-C3알킬이고;Het가 피리딘, 퀴놀린, 티아졸, 티아디아졸 및 이미다졸 중에서 선택된 헤테로 사이클릭 그룹이며;X가 산소 또는 황이고; Y,Y1,Y2,Y3,Y4및 Z가 각각 독립적으로 수소, 할로겐, C1-C3알킬, C2또는 C3알케닐, -COOR1, -COR1, C1-C3알콕시, C1-C3알킬디오,-CH2SR1,-CON, -SCF,-SO2N, -CN, -CF31이며;Y2는 또한 OCH2CO2R1이고; n이 각각 독립적으로 0내지 4인 일반식(Ⅰ)의 화합물 및 그의 약제학적으로 무독한 염을 제조하는 방법.
- 제2항에 있어서, R1이 각각 메틸이며 ;R2가 수소,또는 -CH2-Het-Y이고;R3가 4-하이드록실, 4-OSO3H, 또는 4-OPO3H2이며;Het가 피리딘이고; n이 1또는 2이며 X가 산소이고; Y,Y1,Y2,Y3,Y4및 Z가 각각 독립적으로 수소, 불소, 염소, 메틸, 프로필, 알릴, -COOR1, -COR1, 메톡시, 메틸티오, -CH2SR1, -CF31인 일반식(Ⅰ)의 화합물 및 그의 약제학적으로 무독한 염을 제조하는 방법.
- 제1항에 있어서, 하기 표에 정의한 바와 같은 일반식(Ⅰ)의 화합물 및 그의 약제학적으로 무독한 염을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US62237284A | 1984-06-20 | 1984-06-20 | |
CA622372 | 1984-06-20 |
Publications (1)
Publication Number | Publication Date |
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KR860000292A true KR860000292A (ko) | 1986-01-27 |
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---|---|---|---|
KR1019850004373A KR860000292A (ko) | 1984-06-20 | 1985-06-20 | 벤조푸란유도체의 제조방법 |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP0165810B1 (ko) |
JP (1) | JPS6117579A (ko) |
KR (1) | KR860000292A (ko) |
AT (1) | ATE45736T1 (ko) |
AU (1) | AU4377585A (ko) |
CA (1) | CA1281325C (ko) |
DE (1) | DE3572486D1 (ko) |
DK (1) | DK276985A (ko) |
ES (1) | ES8800190A1 (ko) |
GR (1) | GR851493B (ko) |
IL (1) | IL75574A0 (ko) |
PT (1) | PT80660B (ko) |
ZA (1) | ZA854652B (ko) |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4863958A (en) * | 1984-06-20 | 1989-09-05 | Merck Frosst Canada, Inc. | Benzofuran derivatives useful as inhibitors of mammalian leukotriene biosynthesis |
LU85544A1 (fr) * | 1984-09-19 | 1986-04-03 | Cird | Derives heterocycliques aromatiques,leur procede de preparation et leur application dans les domaines therapeutique et cosmetique |
GB2185741B (en) * | 1986-01-27 | 1989-10-25 | American Home Prod | Heterocyclic sulphonamides |
US4714711A (en) * | 1986-11-05 | 1987-12-22 | Merck & Co., Inc. | 6-hydroxy-2(2-hydroxy-4-methoxyphenyl)benzofuran derivatives to inhibit leukotriene biosynthesis |
JPS63123547A (ja) * | 1986-11-12 | 1988-05-27 | Aisin Seiki Co Ltd | 下降端設定ユニツトを有する自動カシメ装置 |
DE3777366D1 (de) * | 1986-12-27 | 1992-04-16 | Takeda Chemical Industries Ltd | 2,3-dihydro-cumaron-derivate, ihre herstellung und verwendung. |
EP0301692A3 (en) * | 1987-06-18 | 1989-03-15 | Merck Frosst Canada Inc. | 4,7-benzofurandione derivatives |
EP0295851A1 (en) * | 1987-06-18 | 1988-12-21 | Merck Frosst Canada Inc. | 4,7-diacyloxybenzofuran derivatives |
IT1229482B (it) * | 1988-08-01 | 1991-09-03 | Foscama Biomed Chim Farma | Acidi (rs) 2 (2,3 diidro 5 idrossi 4,6,7 trimetilbenzofuranil) acetico e 2 (2,3 diidro 5 acilossi 4,6,7 trimetilbenzofuranil) acetici e loro esteri, utili come farmaci mucoregolatori ed antiischemici. |
US4966907A (en) * | 1988-08-12 | 1990-10-30 | Merck & Co., Inc. | 6-substituted 5-hydroxy-2,3-dihydrobenzofurans as inhibitors of leukotriene biosynthesis |
WO1990003374A1 (en) * | 1988-09-28 | 1990-04-05 | The Upjohn Company | 1,4-dihydrothionapthoquinone and heterocyclic congeners which inhibit lipoxygenase enzymes |
US5093351A (en) * | 1989-01-05 | 1992-03-03 | Du Pont Merck Pharmaceutical Company | Substituted indole, benzofuran and benzothiophene derivatives as 5-lipoxygenase inhibitors |
US5006549A (en) * | 1989-05-24 | 1991-04-09 | Merck & Co., Inc. | Novel 7-aroyl-4-hydroxy-3-methyl-benzofurans as dual inhibitors of cyclooxygenase and 5-lipoxygenase |
IT1231341B (it) * | 1989-08-18 | 1991-11-28 | Foscama Biomed Chim Farma | 2,3 diidro 5 ossi 4,6,7 trimetilbenzofurani 2 (rs) sostituiti, utili come farmaci antiossidanti con proprieta' mucoregolatrici e antiischemiche. |
US5118707A (en) * | 1990-10-31 | 1992-06-02 | The Procter & Gamble Company | Compositions for regulating skin wrinkles comprising a benzofuran derivative |
IE68675B1 (en) * | 1990-11-01 | 1996-07-10 | Takeda Chemical Industries Ltd | Aminocoumaran derivatives their production and use |
JP3157882B2 (ja) * | 1991-11-15 | 2001-04-16 | 帝国臓器製薬株式会社 | 新規なベンゾチオフエン誘導体 |
DE4139888A1 (de) * | 1991-12-04 | 1993-06-09 | Jagenberg Ag, 4000 Duesseldorf, De | Vorrichtung zum abbremsen von auf einem stapel abzulegenden boegen, insbesondere papier- oder kartonboegen |
ES2132284T3 (es) * | 1993-08-05 | 1999-08-16 | Hoechst Marion Roussel Inc | Derivados de carbamato de 2-(piperidin-4-il, piridin-4-il y tetrahidropiridin-4-il)-benzofurano-7, su preparacion y su uso como inhibidores de acetilcolinesterasa. |
AU714054B2 (en) * | 1995-01-06 | 1999-12-16 | Toray Industries, Inc. | Benzene-fused heterocyclic derivatives and use of the same |
EP0988289A2 (en) * | 1997-06-05 | 2000-03-29 | Takeda Pharmaceutical Company Limited | Heterocyclic compounds, their production and use |
US6172106B1 (en) | 1998-02-09 | 2001-01-09 | R. Armour Forse | Sesamol inhibition of Δ-5-desaturase activity and uses therefor |
US7709510B2 (en) | 2001-02-20 | 2010-05-04 | Chugai Seiyaku Kabushiki Kaisha | Azoles as malonyl-CoA decarboxylase inhibitors useful as metabolic modulators |
HU229431B1 (en) | 2001-02-20 | 2013-12-30 | Chugai Pharmaceutical Co Ltd | Azoles as malonyl-coa decarboxylase inhibitors useful as metabolic modulators |
JP2005008631A (ja) * | 2003-05-29 | 2005-01-13 | New Industry Research Organization | ベンゾフラン化合物、およびそれを含有してなる医薬組成物 |
WO2004106317A1 (ja) | 2003-05-29 | 2004-12-09 | The New Industry Research Organization | ベンゾフラン化合物、およびそれを含有してなる医薬組成物 |
US7696365B2 (en) | 2003-08-01 | 2010-04-13 | Chugai Seiyaku Kabushiki Kaisha | Heterocyclic compounds useful as malonyl-CoA decarboxylase inhibitors |
JP4648317B2 (ja) | 2003-08-01 | 2011-03-09 | 中外製薬株式会社 | マロニル−CoAデカルボキシラーゼ阻害剤として有用なピペリジン化合物 |
WO2005037258A2 (en) | 2003-08-01 | 2005-04-28 | Chugai Seiyaku Kabushiki Kaisha | Cyanoguanidine-based azole compounds useful as malonyl-coa decarboxylase inhibitors |
US7351726B2 (en) | 2003-09-25 | 2008-04-01 | Wyeth | Substituted oxadiazolidinediones |
US7446201B2 (en) | 2003-09-25 | 2008-11-04 | Wyeth | Substituted heteroaryl benzofuran acids |
MY148644A (en) | 2005-07-18 | 2013-05-15 | Orion Corp | New pharmaceutical compounds |
WO2011022679A2 (en) * | 2009-08-20 | 2011-02-24 | University Of Tennessee Research Foundation, The | Benzofuran cannabinoid compounds and related methods of use |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3476760A (en) * | 1967-03-06 | 1969-11-04 | Smithkline Corp | Substituted piperidinoalkylthianaphthenes and benzofurans |
CH540247A (de) * | 1967-04-21 | 1973-09-28 | Ciba Geigy Ag | Verfahren zur Herstellung von heterocyclischen, Asthylendoppelbindungen enthaltenden Verbindungen |
US4354021A (en) * | 1978-03-31 | 1982-10-12 | The Upjohn Company | 2-Decarboxy-2-tetrazolyl-6-alkoxy-PGI1 compounds |
IT1154888B (it) * | 1980-11-12 | 1987-01-21 | Menarini Sas | Derivati del benzofurano 2-sostituiti e relativi metodi di preparazione |
US4459420A (en) * | 1982-05-17 | 1984-07-10 | The Upjohn Company | Pyrogallol synthesis of anti-atherogenic furochromones |
JPS59104374A (ja) * | 1982-12-08 | 1984-06-16 | Mitsui Petrochem Ind Ltd | ベンゾフラン誘導体の製造方法 |
-
1985
- 1985-06-14 CA CA000484076A patent/CA1281325C/en not_active Expired - Lifetime
- 1985-06-18 AU AU43775/85A patent/AU4377585A/en not_active Abandoned
- 1985-06-18 PT PT80660A patent/PT80660B/pt unknown
- 1985-06-19 DE DE8585304382T patent/DE3572486D1/de not_active Expired
- 1985-06-19 EP EP85304382A patent/EP0165810B1/en not_active Expired
- 1985-06-19 DK DK276985A patent/DK276985A/da not_active Application Discontinuation
- 1985-06-19 ES ES544349A patent/ES8800190A1/es not_active Expired
- 1985-06-19 AT AT85304382T patent/ATE45736T1/de not_active IP Right Cessation
- 1985-06-19 GR GR851493A patent/GR851493B/el unknown
- 1985-06-19 IL IL75574A patent/IL75574A0/xx unknown
- 1985-06-20 KR KR1019850004373A patent/KR860000292A/ko not_active Application Discontinuation
- 1985-06-20 JP JP60133155A patent/JPS6117579A/ja active Pending
- 1985-06-20 ZA ZA854652A patent/ZA854652B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
PT80660A (en) | 1985-07-01 |
JPS6117579A (ja) | 1986-01-25 |
PT80660B (en) | 1987-05-04 |
AU4377585A (en) | 1986-01-02 |
DK276985D0 (da) | 1985-06-19 |
ES8800190A1 (es) | 1987-10-16 |
IL75574A0 (en) | 1985-10-31 |
EP0165810A2 (en) | 1985-12-27 |
ES544349A0 (es) | 1987-10-16 |
ZA854652B (en) | 1986-04-30 |
DK276985A (da) | 1985-12-21 |
EP0165810B1 (en) | 1989-08-23 |
ATE45736T1 (de) | 1989-09-15 |
GR851493B (ko) | 1985-11-25 |
EP0165810A3 (en) | 1986-06-25 |
DE3572486D1 (en) | 1989-09-28 |
CA1281325C (en) | 1991-03-12 |
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Legal Events
Date | Code | Title | Description |
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WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |