RU2001129155A - Соединения с арильными заместителями (варианты), фармацевтическая композиция и способ лечения расстройства, чувствительного к блокаде натриевых каналов у млекопитающего, способ лечения, профилактики различных заболеваний или уменьшения интенсивности гибели или потери нейронов (варианты), способ облегчения или предупреждения эпилептических припадков у животного (варианты), соединение - радиоактивный лиганд для участка связывания в натриевом канале - Google Patents
Соединения с арильными заместителями (варианты), фармацевтическая композиция и способ лечения расстройства, чувствительного к блокаде натриевых каналов у млекопитающего, способ лечения, профилактики различных заболеваний или уменьшения интенсивности гибели или потери нейронов (варианты), способ облегчения или предупреждения эпилептических припадков у животного (варианты), соединение - радиоактивный лиганд для участка связывания в натриевом канале Download PDFInfo
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- RU2001129155A RU2001129155A RU2001129155/04A RU2001129155A RU2001129155A RU 2001129155 A RU2001129155 A RU 2001129155A RU 2001129155/04 A RU2001129155/04 A RU 2001129155/04A RU 2001129155 A RU2001129155 A RU 2001129155A RU 2001129155 A RU2001129155 A RU 2001129155A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- group
- hydrogen
- phenyl
- amino
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 50
- 125000003118 aryl group Chemical group 0.000 title claims 31
- 238000000034 method Methods 0.000 title claims 10
- 241000124008 Mammalia Species 0.000 title claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims 6
- 206010010904 Convulsion Diseases 0.000 title claims 5
- 241001465754 Metazoa Species 0.000 title claims 5
- 108010052164 Sodium Channels Proteins 0.000 title claims 5
- 102000018674 Sodium Channels Human genes 0.000 title claims 5
- 230000002285 radioactive effect Effects 0.000 title claims 3
- 239000003446 ligand Substances 0.000 title claims 2
- 210000002569 neuron Anatomy 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 230000003247 decreasing effect Effects 0.000 title 1
- 201000010099 disease Diseases 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 70
- 239000001257 hydrogen Substances 0.000 claims 56
- 125000000217 alkyl group Chemical group 0.000 claims 54
- -1 cyano, amino Chemical group 0.000 claims 53
- 150000002431 hydrogen Chemical class 0.000 claims 50
- 125000001424 substituent group Chemical group 0.000 claims 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims 33
- 125000003342 alkenyl group Chemical group 0.000 claims 28
- 125000000304 alkynyl group Chemical group 0.000 claims 28
- 125000001072 heteroaryl group Chemical group 0.000 claims 28
- 125000000623 heterocyclic group Chemical group 0.000 claims 25
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 22
- 229910052760 oxygen Inorganic materials 0.000 claims 22
- 125000004103 aminoalkyl group Chemical group 0.000 claims 20
- 125000001188 haloalkyl group Chemical group 0.000 claims 20
- 229910052717 sulfur Inorganic materials 0.000 claims 20
- 125000003282 alkyl amino group Chemical group 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 17
- 125000004432 carbon atom Chemical group C* 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 15
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 13
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 13
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 12
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims 12
- 150000001356 alkyl thiols Chemical class 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 10
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 239000000651 prodrug Substances 0.000 claims 10
- 229940002612 prodrug Drugs 0.000 claims 10
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 9
- 125000006323 alkenyl amino group Chemical group 0.000 claims 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 9
- 125000004414 alkyl thio group Chemical group 0.000 claims 9
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims 9
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 229910052783 alkali metal Inorganic materials 0.000 claims 8
- 150000001340 alkali metals Chemical class 0.000 claims 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 8
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims 8
- 150000003573 thiols Chemical class 0.000 claims 8
- 150000001408 amides Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 208000002193 Pain Diseases 0.000 claims 6
- 125000004442 acylamino group Chemical group 0.000 claims 6
- 125000004423 acyloxy group Chemical group 0.000 claims 6
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 5
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 5
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 230000036407 pain Effects 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 3
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 208000009205 Tinnitus Diseases 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 206010003119 arrhythmia Diseases 0.000 claims 2
- 230000006793 arrhythmia Effects 0.000 claims 2
- 208000028683 bipolar I disease Diseases 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 238000002690 local anesthesia Methods 0.000 claims 2
- 230000000626 neurodegenerative effect Effects 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 231100000886 tinnitus Toxicity 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims 1
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
- VKBOFLKFVJNVON-UHFFFAOYSA-N 1-[3-[4-(4-nitrophenoxy)phenyl]pyrazol-1-yl]ethanone Chemical compound CC(=O)N1C=CC(C=2C=CC(OC=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)=N1 VKBOFLKFVJNVON-UHFFFAOYSA-N 0.000 claims 1
- JUTGEKQFBMEDCR-UHFFFAOYSA-N 1-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound CC(C)(O)CN1N=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 JUTGEKQFBMEDCR-UHFFFAOYSA-N 0.000 claims 1
- CIOBKBATFFYLPA-UHFFFAOYSA-N 1-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]propan-2-one Chemical compound CC(=O)CN1N=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 CIOBKBATFFYLPA-UHFFFAOYSA-N 0.000 claims 1
- LFABDKAVGRGBKB-UHFFFAOYSA-N 1-benzyl-5-[4-(4-fluorophenoxy)phenyl]pyrazole Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2N(N=CC=2)CC=2C=CC=CC=2)C=C1 LFABDKAVGRGBKB-UHFFFAOYSA-N 0.000 claims 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
- LJWPODFBXNZRNJ-UHFFFAOYSA-N 2-[3-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]acetamide Chemical compound NC(=O)CN1C=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 LJWPODFBXNZRNJ-UHFFFAOYSA-N 0.000 claims 1
- PAQCDHCQXZZOTK-UHFFFAOYSA-N 2-[3-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]pyrimidine Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C2=NN(C=C2)C=2N=CC=CN=2)C=C1 PAQCDHCQXZZOTK-UHFFFAOYSA-N 0.000 claims 1
- BIWLLWXBQCQLGG-UHFFFAOYSA-N 2-[3-[4-[4-(trifluoromethyl)phenoxy]phenyl]pyrazol-1-yl]pyrimidine Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1=CC=C(C2=NN(C=C2)C=2N=CC=CN=2)C=C1 BIWLLWXBQCQLGG-UHFFFAOYSA-N 0.000 claims 1
- RYBGVNFVNQDALX-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]-1,3-oxazole-4-carboxamide Chemical compound NC(=O)C1=COC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 RYBGVNFVNQDALX-UHFFFAOYSA-N 0.000 claims 1
- DNGUPPLQAHDYIP-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]-1h-benzimidazole Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1 DNGUPPLQAHDYIP-UHFFFAOYSA-N 0.000 claims 1
- PMYHGIHNTWYDPH-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]-1h-imidazole Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2NC=CN=2)C=C1 PMYHGIHNTWYDPH-UHFFFAOYSA-N 0.000 claims 1
- CSSAKNGWMRWKCM-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]-1h-imidazole-5-carbonitrile Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2NC=C(N=2)C#N)C=C1 CSSAKNGWMRWKCM-UHFFFAOYSA-N 0.000 claims 1
- XBMSSDWJDPMMOF-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]-1h-imidazole-5-carboxamide Chemical compound NC(=O)C1=CNC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 XBMSSDWJDPMMOF-UHFFFAOYSA-N 0.000 claims 1
- ABCFFRHJLNZMLK-UHFFFAOYSA-N 2-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]-1-morpholin-4-ylethanone Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2N(N=CC=2)CC(=O)N2CCOCC2)C=C1 ABCFFRHJLNZMLK-UHFFFAOYSA-N 0.000 claims 1
- KDGBSQOBDISXJY-UHFFFAOYSA-N 2-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2N(N=CC=2)CC(=O)N2CCCC2)C=C1 KDGBSQOBDISXJY-UHFFFAOYSA-N 0.000 claims 1
- JGJHKOJSLNYHPK-UHFFFAOYSA-N 2-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]acetamide Chemical compound NC(=O)CN1N=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 JGJHKOJSLNYHPK-UHFFFAOYSA-N 0.000 claims 1
- QGYHMLTWZSJCMM-UHFFFAOYSA-N 2-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]ethanol Chemical compound OCCN1N=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 QGYHMLTWZSJCMM-UHFFFAOYSA-N 0.000 claims 1
- SFXMKTZKDUFZLC-UHFFFAOYSA-N 2-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]ethyl carbamate Chemical compound NC(=O)OCCN1N=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 SFXMKTZKDUFZLC-UHFFFAOYSA-N 0.000 claims 1
- FTVGTSUFLFFSDY-UHFFFAOYSA-N 3-(4-phenoxyphenyl)pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 FTVGTSUFLFFSDY-UHFFFAOYSA-N 0.000 claims 1
- PVIJYBAGFROCOB-UHFFFAOYSA-N 3-[3-fluoro-4-(4-fluorophenoxy)phenyl]pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC(C=2C=C(F)C(OC=3C=CC(F)=CC=3)=CC=2)=N1 PVIJYBAGFROCOB-UHFFFAOYSA-N 0.000 claims 1
- OYOZIANRHNFTPI-UHFFFAOYSA-N 3-[4-(2,4-difluorophenoxy)phenyl]pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC(C=2C=CC(OC=3C(=CC(F)=CC=3)F)=CC=2)=N1 OYOZIANRHNFTPI-UHFFFAOYSA-N 0.000 claims 1
- DWURZDHXVIRXAE-UHFFFAOYSA-N 3-[4-(2-chloro-4-fluorophenoxy)phenyl]pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC(C=2C=CC(OC=3C(=CC(F)=CC=3)Cl)=CC=2)=N1 DWURZDHXVIRXAE-UHFFFAOYSA-N 0.000 claims 1
- PTUJSDGCLJXZRN-UHFFFAOYSA-N 3-[4-(3-chloro-2-cyanophenoxy)phenyl]pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC(C=2C=CC(OC=3C(=C(Cl)C=CC=3)C#N)=CC=2)=N1 PTUJSDGCLJXZRN-UHFFFAOYSA-N 0.000 claims 1
- VICKOKAOSUOGIB-UHFFFAOYSA-N 3-[4-(4-aminophenoxy)phenyl]pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)=N1 VICKOKAOSUOGIB-UHFFFAOYSA-N 0.000 claims 1
- ITAWDKBZOLCQET-UHFFFAOYSA-N 3-[4-(4-chloro-2-fluorophenoxy)phenyl]pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC(C=2C=CC(OC=3C(=CC(Cl)=CC=3)F)=CC=2)=N1 ITAWDKBZOLCQET-UHFFFAOYSA-N 0.000 claims 1
- RZSLUTWLYXWUSF-UHFFFAOYSA-N 3-[4-(4-cyanophenoxy)phenyl]pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC(C=2C=CC(OC=3C=CC(=CC=3)C#N)=CC=2)=N1 RZSLUTWLYXWUSF-UHFFFAOYSA-N 0.000 claims 1
- YNTRUANMLCUDBZ-UHFFFAOYSA-N 3-[4-(4-fluorophenoxy)phenyl]-n,n-dimethylpyrazole-1-carboxamide Chemical compound CN(C)C(=O)N1C=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 YNTRUANMLCUDBZ-UHFFFAOYSA-N 0.000 claims 1
- MRGZCLZDYCRVKL-UHFFFAOYSA-N 3-[4-(4-fluorophenoxy)phenyl]pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 MRGZCLZDYCRVKL-UHFFFAOYSA-N 0.000 claims 1
- CJNZUOYYPQXPIJ-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)sulfanylphenyl]pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC(C=2C=CC(SC=3C=CC(F)=CC=3)=CC=2)=N1 CJNZUOYYPQXPIJ-UHFFFAOYSA-N 0.000 claims 1
- DNSIJBDKAVUAKO-UHFFFAOYSA-N 3-[4-(4-methoxyphenoxy)phenyl]pyrazole-1-carboxamide Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C2=NN(C=C2)C(N)=O)C=C1 DNSIJBDKAVUAKO-UHFFFAOYSA-N 0.000 claims 1
- TXAVIYCBJUQLRV-UHFFFAOYSA-N 3-[4-(4-nitrophenoxy)phenyl]pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC(C=2C=CC(OC=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)=N1 TXAVIYCBJUQLRV-UHFFFAOYSA-N 0.000 claims 1
- WZVXAXUFPJMFAC-UHFFFAOYSA-N 3-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]propanamide Chemical compound NC(=O)CCN1N=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 WZVXAXUFPJMFAC-UHFFFAOYSA-N 0.000 claims 1
- NWOICISHTNVGPI-UHFFFAOYSA-N 4-[4-(2,4-difluorophenoxy)phenyl]-1-methylimidazole-2-carboxamide Chemical compound N1=C(C(N)=O)N(C)C=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1F NWOICISHTNVGPI-UHFFFAOYSA-N 0.000 claims 1
- NFXDWZKZVQNAAI-UHFFFAOYSA-N 5-[3-fluoro-4-(4-fluorophenoxy)phenyl]-1h-imidazole Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2N=CNC=2)C=C1F NFXDWZKZVQNAAI-UHFFFAOYSA-N 0.000 claims 1
- KIAHCCWSNXBWDQ-UHFFFAOYSA-N 5-[4-(2,4-difluorophenoxy)phenyl]-1h-imidazole Chemical compound FC1=CC(F)=CC=C1OC1=CC=C(C=2N=CNC=2)C=C1 KIAHCCWSNXBWDQ-UHFFFAOYSA-N 0.000 claims 1
- DIHPDGVREOKWAX-UHFFFAOYSA-N 5-[4-(2,4-difluorophenoxy)phenyl]-2-methyl-1h-imidazole Chemical compound N1C(C)=NC(C=2C=CC(OC=3C(=CC(F)=CC=3)F)=CC=2)=C1 DIHPDGVREOKWAX-UHFFFAOYSA-N 0.000 claims 1
- RRBDNNKATHQXSL-UHFFFAOYSA-N 5-[4-(4-chloro-2-fluorophenoxy)phenyl]-1h-imidazole Chemical compound FC1=CC(Cl)=CC=C1OC1=CC=C(C=2N=CNC=2)C=C1 RRBDNNKATHQXSL-UHFFFAOYSA-N 0.000 claims 1
- FMGBXNGBWPWGEK-UHFFFAOYSA-N 5-[4-(4-fluorophenoxy)phenyl]-1h-imidazole Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2N=CNC=2)C=C1 FMGBXNGBWPWGEK-UHFFFAOYSA-N 0.000 claims 1
- CGMPMLHCCFCLQL-UHFFFAOYSA-N 5-[4-(4-fluorophenoxy)phenyl]-1h-pyrazole Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C2=NNC=C2)C=C1 CGMPMLHCCFCLQL-UHFFFAOYSA-N 0.000 claims 1
- UCKUGEJNUBWWMS-UHFFFAOYSA-N 5-[4-(4-fluorophenyl)sulfanylphenyl]-1h-pyrazole Chemical compound C1=CC(F)=CC=C1SC1=CC=C(C2=NNC=C2)C=C1 UCKUGEJNUBWWMS-UHFFFAOYSA-N 0.000 claims 1
- XXNVJVIBKMMONX-UHFFFAOYSA-N 5-[4-[4-(trifluoromethyl)phenoxy]phenyl]-1h-imidazole Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1=CC=C(C=2N=CNC=2)C=C1 XXNVJVIBKMMONX-UHFFFAOYSA-N 0.000 claims 1
- GWGLECLUOBAWQJ-UHFFFAOYSA-N 5-methylsulfanyl-3-(4-phenoxyphenyl)pyrazole-1-carboxamide Chemical compound NC(=O)N1C(SC)=CC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 GWGLECLUOBAWQJ-UHFFFAOYSA-N 0.000 claims 1
- IIFSJFXZWQFZER-UHFFFAOYSA-N 5-methylsulfinyl-3-(4-phenoxyphenyl)pyrazole-1-carboxamide Chemical compound NC(=O)N1C(S(=O)C)=CC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 IIFSJFXZWQFZER-UHFFFAOYSA-N 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- LOPGZBCUMUNSFM-UHFFFAOYSA-N methyl 5-[4-(4-fluorophenoxy)phenyl]-1h-pyrrole-2-carboxylate Chemical compound N1C(C(=O)OC)=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 LOPGZBCUMUNSFM-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- AYFUNGMLUBOVCL-UHFFFAOYSA-N n-[2-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]ethyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCN1N=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 AYFUNGMLUBOVCL-UHFFFAOYSA-N 0.000 claims 1
- VKMFZYMRPXMJHH-UHFFFAOYSA-N n-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]-n-methylacetamide Chemical compound CC(=O)N(C)N1N=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 VKMFZYMRPXMJHH-UHFFFAOYSA-N 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 230000016273 neuron death Effects 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 0 *c1c(*)c(C*CC(C=*)c2c(*3)c(*)c(*)c(*)c2*)c3c(*)c1* Chemical compound *c1c(*)c(C*CC(C=*)c2c(*3)c(*)c(*)c(*)c2*)c3c(*)c1* 0.000 description 8
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
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| ATE538794T1 (de) | 1999-01-13 | 2012-01-15 | Bayer Healthcare Llc | Gamma carboxyarylsubstituierte diphenylharnstoffverbindungen als p38 kinasehemmer |
| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| DE60022333T2 (de) | 1999-04-09 | 2006-07-06 | Euro-Celtique S.A. | Natrium kanalblocker zusammensetzungen und deren verwendung |
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| US7557129B2 (en) | 2003-02-28 | 2009-07-07 | Bayer Healthcare Llc | Cyanopyridine derivatives useful in the treatment of cancer and other disorders |
| MY142651A (en) | 2003-03-18 | 2010-12-15 | Merck Sharp & Dohme | Biaryl substituted triazoles as sodium channel blockers |
| WO2004113274A2 (en) | 2003-05-20 | 2004-12-29 | Bayer Pharmaceuticals Corporation | Diaryl ureas with kinase inhibiting activity |
| PT1558582E (pt) | 2003-07-22 | 2006-05-31 | Arena Pharm Inc | Derivados de diaril- e aril-heteroaril-ureia como moduladores do receptor de serotonina 5-ht2a uteis para a profilaxia e tratamento de desordens relacionadas com o mesmo |
| EA010485B1 (ru) | 2003-07-23 | 2008-10-30 | Байер Фамэсьютиклс Копэрейшн | Производное n,n'-дифенилмочевины, фармацевтическая композиция (варианты) и способ лечения и предупреждения заболеваний и состояний с его использованием (варианты) |
| CA2551611C (en) | 2003-12-26 | 2013-06-25 | Kyowa Kirin Co., Ltd. | Thiazole derivatives for treating or preventing parkinson's disease |
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| US20060084695A1 (en) * | 2004-04-29 | 2006-04-20 | John Griffin | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
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| US20050282883A1 (en) * | 2004-04-29 | 2005-12-22 | John Griffin | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| US7199126B2 (en) | 2004-04-29 | 2007-04-03 | Pharmix Corporation | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| US20050272770A1 (en) * | 2004-04-29 | 2005-12-08 | John Griffin | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| US7163945B2 (en) * | 2004-04-29 | 2007-01-16 | Pharmix Corp. | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
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| US20060111436A1 (en) * | 2004-11-23 | 2006-05-25 | John Griffin | Compositions and treatments for modulating kinase and/or HMG-CoA reductase |
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| JP5286254B2 (ja) | 2006-05-18 | 2013-09-11 | アリーナ ファーマシューティカルズ， インコーポレイテッド | ５−ｈｔ２ａセロトニンレセプター活性のモジュレーターとして有用なフェニルピラゾールの結晶形態および調製方法 |
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| EP2082005B9 (en) | 2006-09-01 | 2013-05-22 | Pleotint, L.L.C. | Ligand exchange thermochromic, (letc), systems |
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