NO322499B1 - Anvendelse av oksazol-og tiazolderivater, for fremstilling av medikament, forbindelse og krystallform omfattende samme, samt farmasoytisk sammensetning. - Google Patents
Anvendelse av oksazol-og tiazolderivater, for fremstilling av medikament, forbindelse og krystallform omfattende samme, samt farmasoytisk sammensetning. Download PDFInfo
- Publication number
- NO322499B1 NO322499B1 NO20020831A NO20020831A NO322499B1 NO 322499 B1 NO322499 B1 NO 322499B1 NO 20020831 A NO20020831 A NO 20020831A NO 20020831 A NO20020831 A NO 20020831A NO 322499 B1 NO322499 B1 NO 322499B1
- Authority
- NO
- Norway
- Prior art keywords
- groups
- group
- substituted
- optionally
- imidazolyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 116
- 239000013078 crystal Substances 0.000 title claims description 111
- 239000003814 drug Substances 0.000 title claims description 51
- 238000002360 preparation method Methods 0.000 title claims description 43
- 150000007979 thiazole derivatives Chemical class 0.000 title claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 229940079593 drug Drugs 0.000 title description 11
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 title description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 62
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 61
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 59
- 125000003118 aryl group Chemical group 0.000 claims abstract description 36
- 125000005843 halogen group Chemical group 0.000 claims abstract description 30
- 125000002252 acyl group Chemical group 0.000 claims abstract description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 28
- 125000003277 amino group Chemical group 0.000 claims abstract description 24
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 24
- 208000033808 peripheral neuropathy Diseases 0.000 claims abstract description 20
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 20
- 230000001737 promoting effect Effects 0.000 claims abstract description 18
- 230000028327 secretion Effects 0.000 claims abstract description 17
- 230000032064 neurotrophin production Effects 0.000 claims abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 13
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 201000001119 neuropathy Diseases 0.000 claims abstract description 10
- 230000007823 neuropathy Effects 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 150000007980 azole derivatives Chemical class 0.000 claims abstract description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- 239000000203 mixture Substances 0.000 claims description 258
- -1 pyrazolyl 1,2,3-oxadiazolyl Chemical group 0.000 claims description 248
- 125000001424 substituent group Chemical group 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 49
- AUNKHRSXVAIONW-UHFFFAOYSA-N 3-[4-(4-chlorophenyl)-2-(2-methylimidazol-1-yl)-1,3-oxazol-5-yl]propan-1-ol Chemical group CC1=NC=CN1C1=NC(C=2C=CC(Cl)=CC=2)=C(CCCO)O1 AUNKHRSXVAIONW-UHFFFAOYSA-N 0.000 claims description 37
- 229940124597 therapeutic agent Drugs 0.000 claims description 36
- 125000004076 pyridyl group Chemical group 0.000 claims description 33
- 125000001931 aliphatic group Chemical group 0.000 claims description 32
- 125000004414 alkyl thio group Chemical group 0.000 claims description 31
- 230000000069 prophylactic effect Effects 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 238000004519 manufacturing process Methods 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000004104 aryloxy group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 125000002883 imidazolyl group Chemical group 0.000 claims description 23
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 150000007978 oxazole derivatives Chemical class 0.000 claims description 17
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 16
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 16
- 125000002723 alicyclic group Chemical group 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000002971 oxazolyl group Chemical group 0.000 claims description 15
- 125000000335 thiazolyl group Chemical group 0.000 claims description 15
- UZKXVFBKGNVTFE-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2-methylimidazol-1-yl)-5-[3-(2-methylphenoxy)propyl]-1,3-oxazole Chemical compound CC1=NC=CN1C(O1)=NC(C=2C=CC(Cl)=CC=2)=C1CCCOC1=CC=CC=C1C UZKXVFBKGNVTFE-UHFFFAOYSA-N 0.000 claims description 14
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 14
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 14
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000002757 morpholinyl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
- 125000005936 piperidyl group Chemical group 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 11
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 10
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 10
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 10
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 10
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 10
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 9
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- YMOSKPJTKUNTFI-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-[3-(2-methoxyphenoxy)propyl]-2-(2-methylimidazol-1-yl)-1,3-oxazole Chemical compound COC1=CC=CC=C1OCCCC1=C(C=2C=CC(Cl)=CC=2)N=C(N2C(=NC=C2)C)O1 YMOSKPJTKUNTFI-UHFFFAOYSA-N 0.000 claims description 8
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000005035 acylthio group Chemical group 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 6
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 6
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 6
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 6
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 6
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000003838 furazanyl group Chemical group 0.000 claims description 6
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 6
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 6
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- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 6
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 5
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- 239000000470 constituent Substances 0.000 claims description 5
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- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
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- 125000003566 oxetanyl group Chemical group 0.000 claims description 5
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- BVKFQERYQBHAPC-UHFFFAOYSA-N 5-[3-(4-chloro-2-methylphenoxy)propyl]-4-(4-chlorophenyl)-2-(2-methylimidazol-1-yl)-1,3-oxazole Chemical group CC1=NC=CN1C(O1)=NC(C=2C=CC(Cl)=CC=2)=C1CCCOC1=CC=C(Cl)C=C1C BVKFQERYQBHAPC-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- ZWKXHKXLLNETEI-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2-methylimidazol-1-yl)-5-[3-(3-methylphenoxy)propyl]-1,3-oxazole Chemical group CC1=NC=CN1C(O1)=NC(C=2C=CC(Cl)=CC=2)=C1CCCOC1=CC=CC(C)=C1 ZWKXHKXLLNETEI-UHFFFAOYSA-N 0.000 claims description 3
- RMDXSJGEUONAFJ-UHFFFAOYSA-N 5-[4-(4-chlorophenyl)-2-(2-methylimidazol-1-yl)-1,3-oxazol-5-yl]pentan-1-ol Chemical compound CC1=NC=CN1C1=NC(C=2C=CC(Cl)=CC=2)=C(CCCCCO)O1 RMDXSJGEUONAFJ-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- NWDGTUZCJHACMU-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(3-imidazol-1-ylpropyl)-2-(2-methylimidazol-1-yl)-1,3-oxazole Chemical compound CC1=NC=CN1C(O1)=NC(C=2C=CC(Cl)=CC=2)=C1CCCN1C=NC=C1 NWDGTUZCJHACMU-UHFFFAOYSA-N 0.000 claims description 2
- YBAOPYYUKJYLFH-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(4-imidazol-1-ylbutyl)-2-(2-methylimidazol-1-yl)-1,3-oxazole Chemical compound CC1=NC=CN1C(O1)=NC(C=2C=CC(Cl)=CC=2)=C1CCCCN1C=NC=C1 YBAOPYYUKJYLFH-UHFFFAOYSA-N 0.000 claims description 2
- UATUWZRXPPGICN-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-[3-(3-methoxyphenoxy)propyl]-2-(2-methylimidazol-1-yl)-1,3-oxazole Chemical compound COC1=CC=CC(OCCCC2=C(N=C(O2)N2C(=NC=C2)C)C=2C=CC(Cl)=CC=2)=C1 UATUWZRXPPGICN-UHFFFAOYSA-N 0.000 claims description 2
- PRFWWSYPGITMMC-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-[3-(4-methoxyphenoxy)propyl]-2-(2-methylimidazol-1-yl)-1,3-oxazole Chemical compound C1=CC(OC)=CC=C1OCCCC1=C(C=2C=CC(Cl)=CC=2)N=C(N2C(=NC=C2)C)O1 PRFWWSYPGITMMC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
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- C07D263/36—One oxygen atom
- C07D263/38—One oxygen atom attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
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- C—CHEMISTRY; METALLURGY
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- C07D263/48—Nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D277/54—Nitrogen and either oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
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- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP23891799 | 1999-08-25 | ||
PCT/JP2000/005681 WO2001014372A2 (en) | 1999-08-25 | 2000-08-24 | Oxazole and thiazole derivatives as neurotrophin production/secretion promoting agent |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20020831D0 NO20020831D0 (no) | 2002-02-20 |
NO20020831L NO20020831L (no) | 2002-04-24 |
NO322499B1 true NO322499B1 (no) | 2006-10-16 |
Family
ID=17037204
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20020831A NO322499B1 (no) | 1999-08-25 | 2002-02-20 | Anvendelse av oksazol-og tiazolderivater, for fremstilling av medikament, forbindelse og krystallform omfattende samme, samt farmasoytisk sammensetning. |
Country Status (29)
Country | Link |
---|---|
US (3) | US6605629B1 (ja) |
EP (1) | EP1206472B1 (ja) |
JP (2) | JP3558588B2 (ja) |
KR (3) | KR100667646B1 (ja) |
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EP0555149B1 (en) * | 1992-02-07 | 1997-08-27 | Mitsubishi Gas Chemical Company, Inc. | Use of oxazopyrroloquinolines and pyrroloquinolinequinones for the manufacture of nerve growth factor production accelerators |
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JP4289688B2 (ja) * | 1996-04-03 | 2009-07-01 | 武田薬品工業株式会社 | オキサゾール誘導体、その製造法および剤 |
PT891340E (pt) * | 1996-04-03 | 2003-03-31 | Takeda Chemical Industries Ltd | Derivados de oxazol sua preparacao e utilizacao |
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EP1019081A2 (en) * | 1997-09-30 | 2000-07-19 | Duke University | Apolipoprotein e/growth factor complexes and methods of use |
CN1314899A (zh) | 1998-07-01 | 2001-09-26 | 武田药品工业株式会社 | 视黄酸类相关的受体机能调节剂 |
AR035016A1 (es) * | 1999-08-25 | 2004-04-14 | Takeda Chemical Industries Ltd | Composicion de azol promotor de produccion/secrecion de neurotrofina, compuesto prodroga del mismo, composicion farmaceutica que lo comprende y uso del mismo para preparar esta ultima. |
US6699995B1 (en) * | 1999-09-16 | 2004-03-02 | Takeda Chemical Industries, Ltd. | Process for the preparation of oxazole derivatives |
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