CN1284777C - 5元杂环化合物、它们的制备和作为药物的应用 - Google Patents
5元杂环化合物、它们的制备和作为药物的应用 Download PDFInfo
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- CN1284777C CN1284777C CNB02807937XA CN02807937A CN1284777C CN 1284777 C CN1284777 C CN 1284777C CN B02807937X A CNB02807937X A CN B02807937XA CN 02807937 A CN02807937 A CN 02807937A CN 1284777 C CN1284777 C CN 1284777C
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- China
- Prior art keywords
- thiazoles
- methyl
- butyl
- imidazoles
- carbamic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000003814 drug Substances 0.000 title claims description 35
- 238000002360 preparation method Methods 0.000 title description 59
- 125000000623 heterocyclic group Chemical group 0.000 title description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 351
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 20
- 230000005764 inhibitory process Effects 0.000 claims abstract description 18
- 208000002193 Pain Diseases 0.000 claims abstract description 17
- 108010052164 Sodium Channels Proteins 0.000 claims abstract description 17
- 102000018674 Sodium Channels Human genes 0.000 claims abstract description 17
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 201000010099 disease Diseases 0.000 claims abstract description 12
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims abstract description 11
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 10
- 206010027599 migraine Diseases 0.000 claims abstract description 10
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 9
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- 206010039966 Senile dementia Diseases 0.000 claims abstract description 8
- 208000004296 neuralgia Diseases 0.000 claims abstract description 8
- 208000021722 neuropathic pain Diseases 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 189
- -1 methylamino- Chemical class 0.000 claims description 107
- USIYRFTZKYKHBI-UHFFFAOYSA-N butyl n-ethylcarbamate Chemical compound CCCCOC(=O)NCC USIYRFTZKYKHBI-UHFFFAOYSA-N 0.000 claims description 98
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 95
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 89
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- 230000000694 effects Effects 0.000 claims description 50
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- 102000010909 Monoamine Oxidase Human genes 0.000 claims description 30
- 108010062431 Monoamine oxidase Proteins 0.000 claims description 30
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 230000003859 lipid peroxidation Effects 0.000 claims description 19
- AHPJFFOLNINEFK-UHFFFAOYSA-N benzyl n-ethylcarbamate Chemical compound CCNC(=O)OCC1=CC=CC=C1 AHPJFFOLNINEFK-UHFFFAOYSA-N 0.000 claims description 16
- NZUFCNSAEKVHMA-UHFFFAOYSA-N 3,3-dimethylbutyl N-ethylcarbamate Chemical compound CCNC(=O)OCCC(C)(C)C NZUFCNSAEKVHMA-UHFFFAOYSA-N 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- KWBIXTIBYFUAGV-UHFFFAOYSA-N ethylcarbamic acid Chemical compound CCNC(O)=O KWBIXTIBYFUAGV-UHFFFAOYSA-N 0.000 claims description 13
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- PNWSHHILERSSLF-UHFFFAOYSA-N 4-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C(O)=O PNWSHHILERSSLF-UHFFFAOYSA-N 0.000 claims description 6
- FJFOVISFRWPXDB-UHFFFAOYSA-N carbamoyloxymethyl carbamate Chemical compound NC(=O)OCOC(N)=O FJFOVISFRWPXDB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 5
- LPTJGJKNRQDZLV-UHFFFAOYSA-N 2-phenylethyl n-ethylcarbamate Chemical compound CCNC(=O)OCCC1=CC=CC=C1 LPTJGJKNRQDZLV-UHFFFAOYSA-N 0.000 claims description 4
- GBHCAUXEYOATDB-UHFFFAOYSA-N 3-methylbutyl n-ethylcarbamate Chemical compound CCNC(=O)OCCC(C)C GBHCAUXEYOATDB-UHFFFAOYSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- YAUWHXKOYHADTR-UHFFFAOYSA-N butyl n-methylcarbamate Chemical compound CCCCOC(=O)NC YAUWHXKOYHADTR-UHFFFAOYSA-N 0.000 claims description 3
- SURZCVYFPAXNGN-UHFFFAOYSA-N methyl-carbamic acid ethyl ester Chemical compound CCOC(=O)NC SURZCVYFPAXNGN-UHFFFAOYSA-N 0.000 claims description 3
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract description 18
- 150000002460 imidazoles Chemical class 0.000 abstract description 6
- 230000000144 pharmacologic effect Effects 0.000 abstract description 4
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 abstract description 2
- 150000002632 lipids Chemical class 0.000 abstract description 2
- CLIKZMFGJGSZOP-UHFFFAOYSA-N N1C(CCNC(=O)O)=NC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 Chemical compound N1C(CCNC(=O)O)=NC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 CLIKZMFGJGSZOP-UHFFFAOYSA-N 0.000 abstract 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 description 158
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 114
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 80
- 239000007787 solid Substances 0.000 description 73
- 235000002639 sodium chloride Nutrition 0.000 description 70
- 239000002585 base Substances 0.000 description 67
- 239000000203 mixture Substances 0.000 description 67
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
- 238000000034 method Methods 0.000 description 55
- 125000004433 nitrogen atom Chemical group N* 0.000 description 53
- 239000000047 product Substances 0.000 description 52
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 50
- 239000002253 acid Substances 0.000 description 49
- 239000002904 solvent Substances 0.000 description 49
- 125000003545 alkoxy group Chemical group 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 47
- 239000006227 byproduct Substances 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 38
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- 125000005842 heteroatom Chemical group 0.000 description 36
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 35
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- 239000012074 organic phase Substances 0.000 description 32
- 125000003118 aryl group Chemical group 0.000 description 31
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 28
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- 125000005843 halogen group Chemical group 0.000 description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
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- 239000012429 reaction media Substances 0.000 description 22
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- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- A61P25/24—Antidepressants
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
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- 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
-
- 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
- C07D417/06—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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Anesthesiology (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Description
Claims (12)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0104943A FR2823208B1 (fr) | 2001-04-10 | 2001-04-10 | Derives d'heterocycles a 5 chainons, leur preparation et leur application a titre de medicaments |
FR01/04943 | 2001-04-10 | ||
FR02/01811 | 2002-02-14 | ||
FR0201811 | 2002-02-14 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1535267A CN1535267A (zh) | 2004-10-06 |
CN1284777C true CN1284777C (zh) | 2006-11-15 |
Family
ID=26212970
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CNB02807937XA Expired - Fee Related CN1284777C (zh) | 2001-04-10 | 2002-04-09 | 5元杂环化合物、它们的制备和作为药物的应用 |
Country Status (23)
Country | Link |
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EP (1) | EP1379514B1 (zh) |
JP (1) | JP4422964B2 (zh) |
KR (1) | KR100865809B1 (zh) |
CN (1) | CN1284777C (zh) |
AR (1) | AR036329A1 (zh) |
AU (1) | AU2002307980B2 (zh) |
BR (2) | BRPI0208703B1 (zh) |
CA (1) | CA2443403C (zh) |
CZ (1) | CZ304550B6 (zh) |
DE (1) | DE60232959D1 (zh) |
ES (1) | ES2328467T3 (zh) |
HK (1) | HK1070055A1 (zh) |
HU (1) | HU228192B1 (zh) |
IL (2) | IL158121A0 (zh) |
IS (1) | IS2724B (zh) |
MX (1) | MXPA03009194A (zh) |
MY (1) | MY142094A (zh) |
NO (1) | NO326051B1 (zh) |
NZ (1) | NZ528645A (zh) |
PL (1) | PL211939B1 (zh) |
RU (1) | RU2288224C2 (zh) |
TW (1) | TWI248438B (zh) |
WO (1) | WO2002083656A2 (zh) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI283577B (en) | 1999-10-11 | 2007-07-11 | Sod Conseils Rech Applic | Pharmaceutical composition of imidazole derivatives acting as modulators of sodium channels and the use thereof |
US7291641B2 (en) * | 1999-10-11 | 2007-11-06 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Derivatives of heterocycles with 5 members, their preparation and their use as medicaments |
CA2469228A1 (en) | 2001-12-03 | 2003-06-12 | Japan Tobacco Inc. | Azole compound and medicinal use thereof |
BRPI0409136A (pt) * | 2003-04-09 | 2006-04-25 | Japan Tobacco Inc | composto heteroaromático pentacìclico e uso medicinal do mesmo |
ES2272911T3 (es) * | 2003-04-25 | 2007-05-01 | Neurofit Sas | Uso de derivados de fenotiazina piperazina en la fabricacion de un medicamento con efectos neuroprotector y/o neurotroficos sobre cns y/o pns. |
FR2888116A1 (fr) | 2005-07-08 | 2007-01-12 | Sod Conseils Rech Applic | Derives de thiazoles pour traiter les dyskinesies |
EP1806819A1 (en) * | 2006-01-05 | 2007-07-11 | Constructions Electroniques + Telecommunications, en abrégé "C.E.+T" | Backup power system |
TW200848417A (en) * | 2007-02-22 | 2008-12-16 | Organon Nv | Indole derivatives |
PE20141682A1 (es) * | 2011-10-26 | 2014-11-14 | Pfizer Ltd | Derivados de (4-fenilimidazol-2-il) etilamina utiles como moduladores de canal de sodio |
CN113831360A (zh) * | 2021-09-10 | 2021-12-24 | 中钢集团南京新材料研究院有限公司 | 酰胺邻位导向硼化合成1-咔唑-硼酸频哪醇酯的方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5326770A (en) | 1992-07-17 | 1994-07-05 | The Du Pont Merck Pharmaceutical Company | Monoamine oxidase-B (MAO-B) inhibitory 5-substituted 2,4-thiazolidinediones useful in treating memory disorders of mammals |
WO1996016040A1 (en) * | 1994-11-23 | 1996-05-30 | Neurogen Corporation | Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives; new classes of dopamine receptor subtype specific ligands |
EP0891358A1 (fr) * | 1995-10-11 | 1999-01-20 | Synthelabo | Composes derives d'oxazolidin-2-one, leur procede de preparation et leur application en therapeutique |
WO1998027108A2 (en) * | 1996-12-16 | 1998-06-25 | Fujisawa Pharmaceutical Co., Ltd. | New amide compounds and their use as nitric oxide synthase inhibitors |
FR2764889B1 (fr) * | 1997-06-20 | 2000-09-01 | Sod Conseils Rech Applic | Nouveaux derives du 2-(iminomethyl)amino-phenyle, leur preparation, leur application a titre de medicaments et les compositions pharmaceutiques les contenant |
PL339673A1 (en) * | 1997-10-06 | 2001-01-02 | Lilly Co Eli | Novel compounds suitable for use as neuroprotective agents |
NZ508765A (en) * | 1998-06-12 | 2003-10-31 | Sod Conseils Rech Applic | Beta-carboline derivatives and pharmaceuticals thereof that selectively bind somatostatin receptor subtypes |
IL145508A0 (en) * | 1999-03-26 | 2002-06-30 | Euro Celtique Sa | Aryl substituted pyrazole, imidazole, oxazole, thiazole and pyrrole derivatives and pharmaceutical compositions containing the same |
TWI283577B (en) * | 1999-10-11 | 2007-07-11 | Sod Conseils Rech Applic | Pharmaceutical composition of imidazole derivatives acting as modulators of sodium channels and the use thereof |
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2002
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- 2002-04-09 KR KR1020037013243A patent/KR100865809B1/ko not_active IP Right Cessation
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- 2002-04-09 EP EP02761921A patent/EP1379514B1/fr not_active Expired - Lifetime
- 2002-04-09 JP JP2002581412A patent/JP4422964B2/ja not_active Expired - Fee Related
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- 2002-04-09 BR BRPI0208703-0A patent/BRPI0208703B1/pt unknown
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- 2002-04-09 CZ CZ2003-3054A patent/CZ304550B6/cs not_active IP Right Cessation
- 2002-04-09 ES ES02761921T patent/ES2328467T3/es not_active Expired - Lifetime
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2003
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2005
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