ZA200509241B - New benzimidazole derivatives - Google Patents
New benzimidazole derivatives Download PDFInfo
- Publication number
- ZA200509241B ZA200509241B ZA200509241A ZA200509241A ZA200509241B ZA 200509241 B ZA200509241 B ZA 200509241B ZA 200509241 A ZA200509241 A ZA 200509241A ZA 200509241 A ZA200509241 A ZA 200509241A ZA 200509241 B ZA200509241 B ZA 200509241B
- Authority
- ZA
- South Africa
- Prior art keywords
- benzimidazol
- acetamide
- nitro
- trifluoromethyl
- phenyl
- Prior art date
Links
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 115
- 150000001875 compounds Chemical class 0.000 claims description 97
- -1 Cy.shaloalkylO Chemical group 0.000 claims description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
- 238000011282 treatment Methods 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 230000001154 acute effect Effects 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 208000035475 disorder Diseases 0.000 claims description 24
- 208000002193 Pain Diseases 0.000 claims description 23
- 230000001684 chronic effect Effects 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 208000004296 neuralgia Diseases 0.000 claims description 10
- 208000021722 neuropathic pain Diseases 0.000 claims description 10
- 206010065390 Inflammatory pain Diseases 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 230000001404 mediated effect Effects 0.000 claims description 9
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- 208000005298 acute pain Diseases 0.000 claims description 8
- 239000000543 intermediate Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- SMLSIPPNQZWIOR-UHFFFAOYSA-N 2-(2-bromo-6-nitroanilino)ethanol Chemical compound OCCNC1=C(Br)C=CC=C1[N+]([O-])=O SMLSIPPNQZWIOR-UHFFFAOYSA-N 0.000 claims description 7
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- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 230000036407 pain Effects 0.000 claims description 7
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- PLWWZNCKGRRXOP-UHFFFAOYSA-N 2-(7-bromobenzimidazol-1-yl)acetic acid Chemical compound C1=CC(Br)=C2N(CC(=O)O)C=NC2=C1 PLWWZNCKGRRXOP-UHFFFAOYSA-N 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 6
- TZGFBDWLXYAMDY-UHFFFAOYSA-N 2-(2-amino-6-bromoanilino)ethanol Chemical compound NC1=CC=CC(Br)=C1NCCO TZGFBDWLXYAMDY-UHFFFAOYSA-N 0.000 claims description 5
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- QDBKFHDOAYGNJE-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1NCCO QDBKFHDOAYGNJE-UHFFFAOYSA-N 0.000 claims description 5
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- YMGMBTMVANYRLE-UHFFFAOYSA-N 3-amino-2-(2-hydroxyethylamino)-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(N)=C1NCCO YMGMBTMVANYRLE-UHFFFAOYSA-N 0.000 claims description 5
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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 claims description 5
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- UZZYGJUPFKPADV-UHFFFAOYSA-N methyl 2-(2-hydroxyethylamino)-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1NCCO UZZYGJUPFKPADV-UHFFFAOYSA-N 0.000 claims description 5
- MZGLXQDJSUOGMG-UHFFFAOYSA-N n-(2-methyl-6-nitrophenyl)formamide Chemical compound CC1=CC=CC([N+]([O-])=O)=C1NC=O MZGLXQDJSUOGMG-UHFFFAOYSA-N 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- HABIAWQPYSFYAP-UHFFFAOYSA-N 2-(2-fluoro-6-nitroanilino)ethanol Chemical compound OCCNC1=C(F)C=CC=C1[N+]([O-])=O HABIAWQPYSFYAP-UHFFFAOYSA-N 0.000 claims description 4
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- CTMUOPMCEIJFPH-UHFFFAOYSA-N 2-(7-cyanobenzimidazol-1-yl)acetic acid Chemical compound C1=CC(C#N)=C2N(CC(=O)O)C=NC2=C1 CTMUOPMCEIJFPH-UHFFFAOYSA-N 0.000 claims description 4
- GSXRESWOZKELOS-UHFFFAOYSA-N 2-(7-methylsulfonylbenzimidazol-1-yl)ethanol Chemical compound CS(=O)(=O)C1=CC=CC2=C1N(CCO)C=N2 GSXRESWOZKELOS-UHFFFAOYSA-N 0.000 claims description 4
- PFXOXYJJWUYAJY-UHFFFAOYSA-N 2-(7-nitrobenzimidazol-1-yl)propanenitrile Chemical compound C1=CC([N+]([O-])=O)=C2N(C(C#N)C)C=NC2=C1 PFXOXYJJWUYAJY-UHFFFAOYSA-N 0.000 claims description 4
- BXOCOVZSCBKVCP-UHFFFAOYSA-N 2-chloro-1-nitro-3-propylsulfonylbenzene Chemical compound CCCS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1Cl BXOCOVZSCBKVCP-UHFFFAOYSA-N 0.000 claims description 4
- BUTSTAATVMYIHU-UHFFFAOYSA-N 3-(2-hydroxyethyl)-n,n-dimethylbenzimidazole-4-sulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC2=C1N(CCO)C=N2 BUTSTAATVMYIHU-UHFFFAOYSA-N 0.000 claims description 4
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- 206010003246 arthritis Diseases 0.000 claims description 4
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 4
- 201000003146 cystitis Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- CYMFZHDSEUFIII-UHFFFAOYSA-N ethyl 2-(n-formyl-2-methyl-6-nitroanilino)acetate Chemical compound CCOC(=O)CN(C=O)C1=C(C)C=CC=C1[N+]([O-])=O CYMFZHDSEUFIII-UHFFFAOYSA-N 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- KIIDYVDGOFLEMH-UHFFFAOYSA-N methyl 3-(2-hydroxyethyl)benzimidazole-4-carboxylate Chemical compound COC(=O)C1=CC=CC2=C1N(CCO)C=N2 KIIDYVDGOFLEMH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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- 208000009935 visceral pain Diseases 0.000 claims description 4
- SBPHCNNHDIQASA-UHFFFAOYSA-N 2-(7-chlorobenzimidazol-1-yl)ethanol Chemical compound C1=CC(Cl)=C2N(CCO)C=NC2=C1 SBPHCNNHDIQASA-UHFFFAOYSA-N 0.000 claims description 3
- KUUUIUJSKYPFJX-UHFFFAOYSA-N 2-(7-fluorobenzimidazol-1-yl)ethanol Chemical compound C1=CC(F)=C2N(CCO)C=NC2=C1 KUUUIUJSKYPFJX-UHFFFAOYSA-N 0.000 claims description 3
- MWRXEWAYZFDWAZ-UHFFFAOYSA-N 2-(7-nitrobenzimidazol-1-yl)acetic acid Chemical compound C1=CC([N+]([O-])=O)=C2N(CC(=O)O)C=NC2=C1 MWRXEWAYZFDWAZ-UHFFFAOYSA-N 0.000 claims description 3
- RWTVJVBEEPSAII-UHFFFAOYSA-N 2-[7-(trifluoromethyl)benzimidazol-1-yl]acetic acid Chemical compound C1=CC(C(F)(F)F)=C2N(CC(=O)O)C=NC2=C1 RWTVJVBEEPSAII-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
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- ZFDARQNNEWGUBD-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-(7-nitrobenzimidazol-1-yl)acetamide Chemical compound C1=CC(OC)=CC=C1NC(=O)CN1C2=C([N+]([O-])=O)C=CC=C2N=C1 ZFDARQNNEWGUBD-UHFFFAOYSA-N 0.000 claims description 3
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- DWMWQTSBJIUPMM-UHFFFAOYSA-N 2-(2-amino-6-propylsulfonylanilino)ethanol Chemical compound CCCS(=O)(=O)C1=CC=CC(N)=C1NCCO DWMWQTSBJIUPMM-UHFFFAOYSA-N 0.000 claims description 2
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- SOOKONZRBGILGB-UHFFFAOYSA-N 2-(4-methylbenzimidazol-1-yl)-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound C1=NC=2C(C)=CC=CC=2N1CC(=O)NC1=CC=CC(C(F)(F)F)=C1 SOOKONZRBGILGB-UHFFFAOYSA-N 0.000 claims description 2
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- RDYUVMUWKOLDQH-UHFFFAOYSA-N 2-(6,7-difluorobenzimidazol-1-yl)-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound C12=C(F)C(F)=CC=C2N=CN1CC(=O)NC1=CC=CC(C(F)(F)F)=C1 RDYUVMUWKOLDQH-UHFFFAOYSA-N 0.000 claims description 2
- IMOXIHQVEAJYAD-UHFFFAOYSA-N 2-(7-bromobenzimidazol-1-yl)-n-(3,5-dimethoxyphenyl)acetamide Chemical compound COC1=CC(OC)=CC(NC(=O)CN2C3=C(Br)C=CC=C3N=C2)=C1 IMOXIHQVEAJYAD-UHFFFAOYSA-N 0.000 claims description 2
- NJNANHLUIFTEFA-UHFFFAOYSA-N 2-(7-bromobenzimidazol-1-yl)-n-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(NC(=O)CN2C3=C(Br)C=CC=C3N=C2)=C1 NJNANHLUIFTEFA-UHFFFAOYSA-N 0.000 claims description 2
- ZMMIJGDKSGFFNF-UHFFFAOYSA-N 2-(7-chlorobenzimidazol-1-yl)-n-(4-methylphenyl)acetamide Chemical compound C1=CC(C)=CC=C1NC(=O)CN1C2=C(Cl)C=CC=C2N=C1 ZMMIJGDKSGFFNF-UHFFFAOYSA-N 0.000 claims description 2
- QOTWWGPYJMHWTB-UHFFFAOYSA-N 2-(7-fluorobenzimidazol-1-yl)acetic acid Chemical compound C1=CC(F)=C2N(CC(=O)O)C=NC2=C1 QOTWWGPYJMHWTB-UHFFFAOYSA-N 0.000 claims description 2
- BVLWOSHETIPVRV-UHFFFAOYSA-N 2-(7-methylsulfonylbenzimidazol-1-yl)acetic acid Chemical compound CS(=O)(=O)C1=CC=CC2=C1N(CC(O)=O)C=N2 BVLWOSHETIPVRV-UHFFFAOYSA-N 0.000 claims description 2
- CPDAUFHCDLJIJT-UHFFFAOYSA-N 2-(7-nitrobenzimidazol-1-yl)-n-(3,4,5-trimethoxyphenyl)acetamide Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)CN2C3=C([N+]([O-])=O)C=CC=C3N=C2)=C1 CPDAUFHCDLJIJT-UHFFFAOYSA-N 0.000 claims description 2
- DXOVTBGMKLEUIW-UHFFFAOYSA-N 2-(7-nitrobenzimidazol-1-yl)-n-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C1=2C([N+](=O)[O-])=CC=CC=2N=CN1CC(=O)NC1=CC=C(C(F)(F)F)C=C1 DXOVTBGMKLEUIW-UHFFFAOYSA-N 0.000 claims description 2
- SBCMGWCPHHIRRP-UHFFFAOYSA-N 2-(7-nitrobenzimidazol-1-yl)-n-[[4-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound C1=2C([N+](=O)[O-])=CC=CC=2N=CN1CC(=O)NCC1=CC=C(C(F)(F)F)C=C1 SBCMGWCPHHIRRP-UHFFFAOYSA-N 0.000 claims description 2
- AEKQHBBRHBSFAB-UHFFFAOYSA-N 2-(7-nitrobenzimidazol-1-yl)propanoic acid Chemical compound C1=CC([N+]([O-])=O)=C2N(C(C(O)=O)C)C=NC2=C1 AEKQHBBRHBSFAB-UHFFFAOYSA-N 0.000 claims description 2
- WSNGLRCFOCEWGQ-UHFFFAOYSA-N 2-(benzimidazol-1-yl)-n-(3,5-dimethoxyphenyl)acetamide Chemical compound COC1=CC(OC)=CC(NC(=O)CN2C3=CC=CC=C3N=C2)=C1 WSNGLRCFOCEWGQ-UHFFFAOYSA-N 0.000 claims description 2
- KLPQMNGCXDTXOV-UHFFFAOYSA-N 2-(benzimidazol-1-yl)-n-(3-chloro-4-fluorophenyl)acetamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(=O)CN1C2=CC=CC=C2N=C1 KLPQMNGCXDTXOV-UHFFFAOYSA-N 0.000 claims description 2
- QUXUDJCOVLONFB-UHFFFAOYSA-N 2-(benzimidazol-1-yl)-n-(3-fluoro-4-methylphenyl)acetamide Chemical compound C1=C(F)C(C)=CC=C1NC(=O)CN1C2=CC=CC=C2N=C1 QUXUDJCOVLONFB-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
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- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- ABDGUBJFBFFDJV-UHFFFAOYSA-N methyl 3-[2-(3,5-dimethoxyanilino)-2-oxoethyl]benzimidazole-4-carboxylate Chemical compound C1=2C(C(=O)OC)=CC=CC=2N=CN1CC(=O)NC1=CC(OC)=CC(OC)=C1 ABDGUBJFBFFDJV-UHFFFAOYSA-N 0.000 claims description 2
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- POYHQOWEAHCOGC-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-(7-nitrobenzimidazol-1-yl)acetamide Chemical compound C1=C(C)C(C)=CC=C1NC(=O)CN1C2=C([N+]([O-])=O)C=CC=C2N=C1 POYHQOWEAHCOGC-UHFFFAOYSA-N 0.000 claims description 2
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- WZXRTHFIHZXDTF-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(7-nitrobenzimidazol-1-yl)acetamide Chemical compound C1=2C([N+](=O)[O-])=CC=CC=2N=CN1CC(=O)NC1=CC=CC(Cl)=C1 WZXRTHFIHZXDTF-UHFFFAOYSA-N 0.000 claims description 2
- IRHZXUKPOXDSBS-UHFFFAOYSA-N n-(3-ethoxyphenyl)-2-(7-nitrobenzimidazol-1-yl)acetamide Chemical compound CCOC1=CC=CC(NC(=O)CN2C3=C([N+]([O-])=O)C=CC=C3N=C2)=C1 IRHZXUKPOXDSBS-UHFFFAOYSA-N 0.000 claims description 2
- KKOPARIYKSAPOP-UHFFFAOYSA-N n-(3-ethoxyphenyl)-2-(7-nitrobenzimidazol-1-yl)propanamide Chemical compound CCOC1=CC=CC(NC(=O)C(C)N2C3=C([N+]([O-])=O)C=CC=C3N=C2)=C1 KKOPARIYKSAPOP-UHFFFAOYSA-N 0.000 claims description 2
- WWJNIHMINOPOOW-UHFFFAOYSA-N n-(4-cyanophenyl)-2-(7-nitrobenzimidazol-1-yl)acetamide Chemical compound C1=2C([N+](=O)[O-])=CC=CC=2N=CN1CC(=O)NC1=CC=C(C#N)C=C1 WWJNIHMINOPOOW-UHFFFAOYSA-N 0.000 claims description 2
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- WEZGZEULFBUYMK-UHFFFAOYSA-N n-(3-fluoro-4-methoxyphenyl)-2-(7-nitrobenzimidazol-1-yl)acetamide Chemical compound C1=C(F)C(OC)=CC=C1NC(=O)CN1C2=C([N+]([O-])=O)C=CC=C2N=C1 WEZGZEULFBUYMK-UHFFFAOYSA-N 0.000 description 1
- YHJITKUVZKHYHY-UHFFFAOYSA-N n-(3-methylsulfonylphenyl)-2-(7-nitrobenzimidazol-1-yl)acetamide Chemical compound CS(=O)(=O)C1=CC=CC(NC(=O)CN2C3=C([N+]([O-])=O)C=CC=C3N=C2)=C1 YHJITKUVZKHYHY-UHFFFAOYSA-N 0.000 description 1
- IBMGVCGIWJKMJQ-UHFFFAOYSA-N n-(4-bromo-2-fluorophenyl)-2-(7-nitrobenzimidazol-1-yl)acetamide Chemical compound C1=2C([N+](=O)[O-])=CC=CC=2N=CN1CC(=O)NC1=CC=C(Br)C=C1F IBMGVCGIWJKMJQ-UHFFFAOYSA-N 0.000 description 1
- IYRCLHVSFDRKQB-UHFFFAOYSA-N n-(4-butylphenyl)-2-(7-nitrobenzimidazol-1-yl)acetamide Chemical compound C1=CC(CCCC)=CC=C1NC(=O)CN1C2=C([N+]([O-])=O)C=CC=C2N=C1 IYRCLHVSFDRKQB-UHFFFAOYSA-N 0.000 description 1
- YDRDRPXOAVABHZ-UHFFFAOYSA-N n-(4-methylsulfonylphenyl)-2-(7-nitrobenzimidazol-1-yl)acetamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC(=O)CN1C2=C([N+]([O-])=O)C=CC=C2N=C1 YDRDRPXOAVABHZ-UHFFFAOYSA-N 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- BZKQPMWBAIIWNE-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-2-(7-nitrobenzimidazol-1-yl)acetamide Chemical compound C1=CC(C(C)(C)C)=CC=C1CNC(=O)CN1C2=C([N+]([O-])=O)C=CC=C2N=C1 BZKQPMWBAIIWNE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
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- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
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- 238000002953 preparative HPLC Methods 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 description 1
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- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
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- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 208000017520 skin disease Diseases 0.000 description 1
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- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
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- 230000000472 traumatic effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
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- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Classifications
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
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- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/16—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to carbon atoms of six-membered aromatic rings
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- C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
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- C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C07D235/30—Nitrogen atoms not forming part of a nitro radical
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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
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- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D417/12—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 chain containing hetero atoms as chain links
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SE0301446A SE0301446D0 (sv) | 2003-05-16 | 2003-05-16 | New Compounds |
SE0400043A SE0400043D0 (sv) | 2003-05-16 | 2004-01-12 | New compounds |
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ZA200509241A ZA200509241B (en) | 2003-05-16 | 2005-11-15 | New benzimidazole derivatives |
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EP (2) | EP1626964B1 (pt) |
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KR (1) | KR101110404B1 (pt) |
CN (2) | CN101328150A (pt) |
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AT (1) | ATE421506T1 (pt) |
AU (2) | AU2004238177B2 (pt) |
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DK (1) | DK1626964T3 (pt) |
ES (1) | ES2319529T3 (pt) |
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HR (1) | HRP20090167T1 (pt) |
IL (1) | IL199668A0 (pt) |
IS (1) | IS2656B (pt) |
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PL (1) | PL1626964T3 (pt) |
PT (1) | PT1626964E (pt) |
RU (1) | RU2337098C2 (pt) |
SE (2) | SE0301446D0 (pt) |
SG (2) | SG171471A1 (pt) |
SI (1) | SI1626964T1 (pt) |
TW (1) | TWI333950B (pt) |
UA (1) | UA85842C2 (pt) |
WO (1) | WO2004100865A2 (pt) |
ZA (1) | ZA200509241B (pt) |
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PE20081692A1 (es) * | 2007-01-24 | 2008-12-18 | Mochida Pharm Co Ltd | Nuevo derivado de heterocicliden acetamida |
BRPI0810035A2 (pt) * | 2007-04-16 | 2016-07-26 | Gruenenthal Gmbh | ligantes de receptor de vaniloide e seu uso para produção de medicamento |
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JP2018052817A (ja) * | 2015-01-21 | 2018-04-05 | 大日本住友製薬株式会社 | 新規ベンズイミダゾール誘導体およびその医薬用途 |
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