CN1033088C - 新的噻唑基苯并呋喃衍生物的制备方法 - Google Patents
新的噻唑基苯并呋喃衍生物的制备方法 Download PDFInfo
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- CN1033088C CN1033088C CN92110877A CN92110877A CN1033088C CN 1033088 C CN1033088 C CN 1033088C CN 92110877 A CN92110877 A CN 92110877A CN 92110877 A CN92110877 A CN 92110877A CN 1033088 C CN1033088 C CN 1033088C
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- salt
- alkyl group
- low alkyl
- compound
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- 238000000034 method Methods 0.000 title claims abstract description 120
- 238000002360 preparation method Methods 0.000 title abstract description 29
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 4
- IQDNFLQNJPENQU-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-1,3-thiazole Chemical class C1=CSC(C=2OC3=CC=CC=C3C=2)=N1 IQDNFLQNJPENQU-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 315
- 150000003839 salts Chemical class 0.000 claims abstract description 250
- 238000006243 chemical reaction Methods 0.000 claims description 195
- 125000000217 alkyl group Chemical group 0.000 claims description 180
- -1 4Be halogen Chemical class 0.000 claims description 125
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 239000002585 base Substances 0.000 claims description 63
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 58
- 230000002829 reductive effect Effects 0.000 claims description 58
- 229910052760 oxygen Inorganic materials 0.000 claims description 51
- 125000002252 acyl group Chemical group 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000004414 alkyl thio group Chemical group 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000003513 alkali Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000004433 nitrogen atom Chemical class N* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 239000000376 reactant Substances 0.000 claims description 9
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- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
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- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
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- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
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- 238000005947 deacylation reaction Methods 0.000 claims description 2
- 230000020335 dealkylation Effects 0.000 claims description 2
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- 239000007800 oxidant agent Substances 0.000 claims description 2
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- 150000004714 phosphonium salts Chemical class 0.000 claims description 2
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- 239000002904 solvent Substances 0.000 description 63
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- 239000012141 concentrate Substances 0.000 description 46
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- 239000002253 acid Substances 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 238000005406 washing Methods 0.000 description 31
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 26
- 238000001816 cooling Methods 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 18
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
- 231100000989 no adverse effect Toxicity 0.000 description 17
- 238000003810 ethyl acetate extraction Methods 0.000 description 16
- 238000010898 silica gel chromatography Methods 0.000 description 16
- 235000014347 soups Nutrition 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 14
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
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- 238000010438 heat treatment Methods 0.000 description 11
- 239000005457 ice water Substances 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 9
- 150000001342 alkaline earth metals Chemical class 0.000 description 9
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- 239000013078 crystal Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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- 239000003153 chemical reaction reagent Substances 0.000 description 8
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- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
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- QLVFXBSHXBMJMU-UHFFFAOYSA-N n-tert-butyl-n-[[2-(5-hydroxy-1-benzofuran-2-yl)-1,3-thiazol-4-yl]methyl]acetamide Chemical compound CC(=O)N(C(C)(C)C)CC1=CSC(C=2OC3=CC=C(O)C=C3C=2)=N1 QLVFXBSHXBMJMU-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- CUWHXIJMTMMRTI-UHFFFAOYSA-N thiadiazol-4-amine Chemical class NC1=CSN=N1 CUWHXIJMTMMRTI-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9117733.7 | 1991-08-16 | ||
| GB919117733A GB9117733D0 (en) | 1991-08-16 | 1991-08-16 | New thiazolylbenzofuran derivatives, processes for the preparation thereof and pharmaceutical composition comprising the same |
| GB9201057.8 | 1992-01-17 | ||
| GB929201057A GB9201057D0 (en) | 1992-01-17 | 1992-01-17 | New thiazolylbenzofuran derivatives,processes for the preparation thereof and pharmaceutical composition comprising the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1070910A CN1070910A (zh) | 1993-04-14 |
| CN1033088C true CN1033088C (zh) | 1996-10-23 |
Family
ID=26299417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN92110877A Expired - Fee Related CN1033088C (zh) | 1991-08-16 | 1992-08-15 | 新的噻唑基苯并呋喃衍生物的制备方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5296495A (enExample) |
| EP (1) | EP0528337B1 (enExample) |
| JP (1) | JP2600644B2 (enExample) |
| KR (1) | KR930004304A (enExample) |
| CN (1) | CN1033088C (enExample) |
| AT (1) | ATE185807T1 (enExample) |
| AU (1) | AU665007B2 (enExample) |
| CA (1) | CA2076192A1 (enExample) |
| DE (1) | DE69230163T2 (enExample) |
| DK (1) | DK0528337T3 (enExample) |
| ES (1) | ES2137169T3 (enExample) |
| GR (1) | GR3032425T3 (enExample) |
| HU (2) | HUT64336A (enExample) |
| MX (1) | MX9204746A (enExample) |
| SG (1) | SG45259A1 (enExample) |
| TW (1) | TW224464B (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2102078A1 (en) * | 1992-11-02 | 1994-05-03 | Akira Takase | A process for producing (e)-alkoxyimino or hydroxyiminoacetamide compounds and intermediates therefor |
| KR100329887B1 (ko) * | 1992-11-02 | 2002-11-02 | 시오노기세이야쿠가부시키가이샤 | (e)-알콕시이미노-및하이드록시이미노-아세트아미드화합물의제조방법 및 그의 제조용중간체 |
| DE4425609A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | Benzofuranyl- und Benzothienyloxazolidinone |
| KR19990076788A (ko) * | 1996-01-22 | 1999-10-15 | 후지야마 아키라 | 티아졸릴벤조푸란 유도체 및 그를 함유하는 약제학적 조성물 |
| ATE257703T1 (de) * | 1997-10-27 | 2004-01-15 | Takeda Chemical Industries Ltd | 1,3-thiazole als adenosine a3 rezeptor antagonisten zur behandlung von asthma, allergien und diabetes |
| US6262066B1 (en) | 1998-07-27 | 2001-07-17 | Schering Corporation | High affinity ligands for nociceptin receptor ORL-1 |
| AU2002349705A1 (en) | 2001-12-03 | 2003-06-17 | Japan Tobacco Inc. | Azole compound and medicinal use thereof |
| US7148248B2 (en) | 2002-11-29 | 2006-12-12 | Masako Nozaki | Method of treating or inhibiting the development of brain inflammation and sepsis |
| EP1424101A3 (en) * | 2002-11-29 | 2004-08-18 | NOZAKI, Masako | Use of a leukotriene C4 and D4 receptor antagonist for the preparation of a medicament for treating or preventing brain inflammation and sepsis |
| WO2004089918A1 (ja) * | 2003-04-09 | 2004-10-21 | Japan Tobacco Inc. | 複素芳香５員環化合物及びその医薬用途 |
| 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 |
| EP1627873A4 (en) | 2003-05-29 | 2007-12-05 | New Ind Res Organization | BENZOFURAN-BASED COMPOUND AND MEDICINAL COMPOSITION CONTAINING THE SAME |
| ITTO20040125A1 (it) * | 2004-03-01 | 2004-06-01 | Rotta Research Lab | Nuove amidine eterocicliche inibitrici la produzione di ossido d'azoto (no) ad attivita' antinfiammatoria ed analgesica |
| CN101022796B (zh) | 2004-07-14 | 2013-02-27 | 炎症研究中心有限公司 | 抑制肿瘤转移的方法 |
| MX2007001561A (es) * | 2004-08-04 | 2007-04-16 | Schering Corp | Formulacion farmaceutica que comprende pleconaril para tratamiento de enfermedades de vias aereas. |
| WO2006046683A1 (en) * | 2004-10-25 | 2006-05-04 | Astellas Pharma Inc. | Thiazolylbenzofuran derivatives as leukotriene and prostaglandin d2 receptor antagonists |
| US20060110449A1 (en) | 2004-10-25 | 2006-05-25 | Lorber Richard R | Pharmaceutical composition |
| JPWO2006054793A1 (ja) * | 2004-11-19 | 2008-06-05 | 財団法人新産業創造研究機構 | 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 |
| KR20090026217A (ko) * | 2006-07-11 | 2009-03-11 | 쉐링 코포레이션 | 치환된 5-옥사졸-2-일-퀴놀린 화합물의 크시나포에이트 염 |
| CA2669704A1 (en) * | 2006-11-16 | 2008-05-22 | Allergan, Inc. | Sulfoximines as kinase inhibitors |
| CA2764830A1 (en) | 2009-06-16 | 2010-12-23 | Schering Corporation | Novel [3,2-c] heteroaryl steroids as glucocorticoid receptor agonists, compositions and uses thereof |
| EP2723717A2 (en) | 2011-06-24 | 2014-04-30 | Amgen Inc. | Trpm8 antagonists and their use in treatments |
| AU2012272898A1 (en) | 2011-06-24 | 2013-04-11 | Amgen Inc. | TRPM8 antagonists and their use in treatments |
| ES2790358T3 (es) | 2011-12-28 | 2020-10-27 | Global Blood Therapeutics Inc | Compuestos de heteroaril aldehído sustituido y métodos para su uso en el aumento de la oxigenación tisular |
| CA3142817A1 (en) * | 2011-12-28 | 2013-07-04 | Global Blood Therapeutics, Inc. | Substituted benzaldehyde compounds and methods for their use in increasing tissue oxygenation |
| US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
| CN112500338A (zh) | 2013-03-15 | 2021-03-16 | 全球血液疗法股份有限公司 | 化合物及其用于调节血红蛋白的用途 |
| US9802900B2 (en) | 2013-03-15 | 2017-10-31 | Global Blood Therapeutics, Inc. | Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin |
| US10266551B2 (en) | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US8952171B2 (en) | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| EP3919056B1 (en) | 2013-03-15 | 2024-08-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9422279B2 (en) | 2013-03-15 | 2016-08-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| EP2968299B1 (en) | 2013-03-15 | 2021-01-20 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9604999B2 (en) | 2013-03-15 | 2017-03-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US10100043B2 (en) | 2013-03-15 | 2018-10-16 | Global Blood Therapeutics, Inc. | Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation |
| US20140274961A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| EA202092627A1 (ru) | 2013-11-18 | 2021-09-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| SG10201911662YA (en) | 2014-02-07 | 2020-02-27 | Global Blood Therapeutics Inc | Crystalline polymorphs of the free base of 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde |
| DK3186233T3 (da) | 2014-08-29 | 2021-11-22 | Chdi Foundation Inc | Prober til billeddannelse af huntingtin-protein |
| MA41841A (fr) | 2015-03-30 | 2018-02-06 | Global Blood Therapeutics Inc | Composés aldéhyde pour le traitement de la fibrose pulmonaire, de l'hypoxie, et de maladies auto-immunes et des tissus conjonctifs |
| HUE072191T2 (hu) | 2015-12-04 | 2025-10-28 | Global Blood Therapeutics Inc | A 2-hidoxi-6-((2-(1-izopropil-1H-pirazol-5-il)piridin-3-il)metoxi)benzaldehid adagolási rendje |
| TWI825524B (zh) | 2016-05-12 | 2023-12-11 | 美商全球血液治療公司 | 用於合成2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)-吡啶-3-基)甲氧基)苯甲醛之方法 |
| TWI778983B (zh) | 2016-10-12 | 2022-10-01 | 美商全球血液治療公司 | 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑 |
| WO2018115984A1 (en) | 2016-12-19 | 2018-06-28 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammation |
| US11014884B2 (en) | 2018-10-01 | 2021-05-25 | Global Blood Therapeutics, Inc. | Modulators of hemoglobin |
| TW202500134A (zh) * | 2023-05-18 | 2025-01-01 | 美商恩維達醫療公司 | G-蛋白偶聯受體之拮抗劑 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62142168A (ja) * | 1985-10-16 | 1987-06-25 | Mitsubishi Chem Ind Ltd | チアゾ−ル誘導体及びそれを有効成分とするロイコトリエンきつ抗剤 |
| US4742057A (en) * | 1985-12-05 | 1988-05-03 | Fujisawa Pharmaceutical Co., Ltd. | Antiallergic thiazole compounds |
| US4908357A (en) * | 1986-04-30 | 1990-03-13 | Fmc Corporation | Photoactive azole pesticides |
| US5001140A (en) * | 1989-04-17 | 1991-03-19 | Hoffmann-La Roche Inc. | Cycloalkylthiazoles |
| JPH02169584A (ja) * | 1988-12-22 | 1990-06-29 | Mitsubishi Kasei Corp | ビニルチアゾール誘導体およびそれを有効成分とする薬剤 |
| US5032588A (en) * | 1989-12-08 | 1991-07-16 | Abbott Laboratories | Thiazole lipoxygenase-inhibiting compounds derived from non-steroidal antiinflammatory carboxylic acids |
| DE3941438A1 (de) * | 1989-12-15 | 1991-06-20 | Hoechst Ag | Neue 2-substituierte 4-(3-alkyl-5-tert.-butyl-4-hydroxy-phenyl)-thiazole, verfahren zu ihrer herstellung, die sie enthaltenden arzneimittel und ihre verwendung |
-
1992
- 1992-08-06 JP JP4210308A patent/JP2600644B2/ja not_active Expired - Fee Related
- 1992-08-12 AT AT92113705T patent/ATE185807T1/de not_active IP Right Cessation
- 1992-08-12 SG SG1996002173A patent/SG45259A1/en unknown
- 1992-08-12 DK DK92113705T patent/DK0528337T3/da active
- 1992-08-12 EP EP92113705A patent/EP0528337B1/en not_active Expired - Lifetime
- 1992-08-12 US US07/929,751 patent/US5296495A/en not_active Expired - Fee Related
- 1992-08-12 ES ES92113705T patent/ES2137169T3/es not_active Expired - Lifetime
- 1992-08-12 DE DE69230163T patent/DE69230163T2/de not_active Expired - Fee Related
- 1992-08-13 AU AU21029/92A patent/AU665007B2/en not_active Ceased
- 1992-08-14 HU HU9202656A patent/HUT64336A/hu unknown
- 1992-08-14 KR KR1019920014712A patent/KR930004304A/ko not_active Ceased
- 1992-08-14 CA CA002076192A patent/CA2076192A1/en not_active Abandoned
- 1992-08-14 TW TW081106455A patent/TW224464B/zh active
- 1992-08-15 CN CN92110877A patent/CN1033088C/zh not_active Expired - Fee Related
- 1992-08-17 MX MX9204746A patent/MX9204746A/es not_active IP Right Cessation
-
1995
- 1995-06-22 HU HU95P/P00346P patent/HU211630A9/hu unknown
-
2000
- 2000-01-19 GR GR20000400122T patent/GR3032425T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0528337B1 (en) | 1999-10-20 |
| ES2137169T3 (es) | 1999-12-16 |
| JP2600644B2 (ja) | 1997-04-16 |
| HU211630A9 (en) | 1995-12-28 |
| SG45259A1 (en) | 1998-01-16 |
| KR930004304A (ko) | 1993-03-22 |
| HU9202656D0 (en) | 1992-10-28 |
| GR3032425T3 (en) | 2000-05-31 |
| MX9204746A (es) | 1994-04-29 |
| TW224464B (enExample) | 1994-06-01 |
| DE69230163D1 (de) | 1999-11-25 |
| CA2076192A1 (en) | 1993-02-17 |
| AU665007B2 (en) | 1995-12-14 |
| JPH05202040A (ja) | 1993-08-10 |
| CN1070910A (zh) | 1993-04-14 |
| ATE185807T1 (de) | 1999-11-15 |
| DE69230163T2 (de) | 2000-03-23 |
| AU2102992A (en) | 1993-02-18 |
| US5296495A (en) | 1994-03-22 |
| DK0528337T3 (da) | 2000-03-27 |
| EP0528337A1 (en) | 1993-02-24 |
| HUT64336A (en) | 1993-12-28 |
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