ZA200108807B - Aryl substituted pyrazoles, imidazoles, oxazoles, thiazoles and pyrroles, and the use thereof. - Google Patents
Aryl substituted pyrazoles, imidazoles, oxazoles, thiazoles and pyrroles, and the use thereof. Download PDFInfo
- Publication number
- ZA200108807B ZA200108807B ZA200108807A ZA200108807A ZA200108807B ZA 200108807 B ZA200108807 B ZA 200108807B ZA 200108807 A ZA200108807 A ZA 200108807A ZA 200108807 A ZA200108807 A ZA 200108807A ZA 200108807 B ZA200108807 B ZA 200108807B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- group
- hydrogen
- compound
- phenyl
- Prior art date
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- 125000003118 aryl group Chemical group 0.000 title claims description 37
- 150000003217 pyrazoles Chemical class 0.000 title description 6
- 150000003233 pyrroles Chemical class 0.000 title description 4
- 150000002460 imidazoles Chemical class 0.000 title description 3
- 150000002916 oxazoles Chemical class 0.000 title description 3
- 150000003557 thiazoles Chemical class 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 60
- 150000002431 hydrogen Chemical class 0.000 claims description 51
- -1 cyano, amino Chemical group 0.000 claims description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000011734 sodium Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 208000002193 Pain Diseases 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 4
- 208000009205 Tinnitus Diseases 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 231100000886 tinnitus Toxicity 0.000 claims description 4
- SGQSMRQYEPPNIA-UHFFFAOYSA-N 5-(4-phenoxyphenyl)-1h-pyrazole Chemical compound C=1C=C(C=2NN=CC=2)C=CC=1OC1=CC=CC=C1 SGQSMRQYEPPNIA-UHFFFAOYSA-N 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 108010052164 Sodium Channels Proteins 0.000 claims description 3
- 102000018674 Sodium Channels Human genes 0.000 claims description 3
- 208000028867 ischemia Diseases 0.000 claims description 3
- 208000020925 Bipolar disease Diseases 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 208000028683 bipolar I disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 208000004296 neuralgia Diseases 0.000 claims description 2
- 208000021722 neuropathic pain Diseases 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 58
- 125000003342 alkenyl group Chemical group 0.000 claims 34
- 125000000304 alkynyl group Chemical group 0.000 claims 31
- 125000000623 heterocyclic group Chemical group 0.000 claims 29
- 125000003282 alkyl amino group Chemical group 0.000 claims 28
- 125000001188 haloalkyl group Chemical group 0.000 claims 21
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 21
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 20
- 125000004432 carbon atom Chemical group C* 0.000 claims 19
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 19
- 125000004103 aminoalkyl group Chemical group 0.000 claims 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 17
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 125000004414 alkyl thio group Chemical group 0.000 claims 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 14
- 125000004423 acyloxy group Chemical group 0.000 claims 13
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 13
- 125000004663 dialkyl amino group Chemical group 0.000 claims 13
- 150000003573 thiols Chemical class 0.000 claims 13
- 125000004442 acylamino group Chemical group 0.000 claims 12
- 150000001408 amides Chemical class 0.000 claims 12
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 12
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 11
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 150000001356 alkyl thiols Chemical class 0.000 claims 10
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 10
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 10
- 239000000651 prodrug Substances 0.000 claims 10
- 229940002612 prodrug Drugs 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims 10
- 125000006323 alkenyl amino group Chemical group 0.000 claims 9
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims 9
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims 9
- 229910052783 alkali metal Inorganic materials 0.000 claims 8
- 150000001340 alkali metals Chemical class 0.000 claims 8
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- 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
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 230000036407 pain Effects 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 3
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 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
- 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
- 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
- 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
- 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
- YYFHWJGANSMBCH-UHFFFAOYSA-N 4-[3-fluoro-4-(4-fluorophenoxy)phenyl]-1,3-thiazole-2-carboxamide Chemical compound S1C(C(=O)N)=NC(C=2C=C(F)C(OC=3C=CC(F)=CC=3)=CC=2)=C1 YYFHWJGANSMBCH-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
- OQKGTYKILXDSGY-UHFFFAOYSA-N 5-(4-phenoxyphenyl)-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)N)=CC=C1C(C=C1)=CC=C1OC1=CC=CC=C1 OQKGTYKILXDSGY-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
- 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
- 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
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 238000000291 inelastic electron tunnelling spectroscopy Methods 0.000 claims 1
- 238000002690 local anesthesia Methods 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
- 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
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 230000000626 neurodegenerative effect Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 1
- 239000002287 radioligand Substances 0.000 claims 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 12
- 108091006146 Channels Proteins 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000001961 anticonvulsive agent Substances 0.000 description 6
- 229940125681 anticonvulsant agent Drugs 0.000 description 5
- 229960000623 carbamazepine Drugs 0.000 description 4
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 4
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229960004194 lidocaine Drugs 0.000 description 3
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 description 2
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229960001848 lamotrigine Drugs 0.000 description 2
- PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 description 2
- 230000000324 neuroprotective effect Effects 0.000 description 2
- 239000002581 neurotoxin Substances 0.000 description 2
- 231100000618 neurotoxin Toxicity 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229960002036 phenytoin Drugs 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
- 150000007659 semicarbazones Chemical class 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 210000004885 white matter Anatomy 0.000 description 2
- PQSKWJVRACFIGK-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)sulfonyl-n,n-dimethyl-4-(4-phenoxyphenyl)pyrazol-3-amine Chemical compound CN(C)C1=NN(S(=O)(=O)C=2C(=CC(Cl)=CC=2)Cl)C=C1C(C=C1)=CC=C1OC1=CC=CC=C1 PQSKWJVRACFIGK-UHFFFAOYSA-N 0.000 description 1
- LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 description 1
- IDYAYDHLGPEZAG-UHFFFAOYSA-N 2-(4-phenoxyphenyl)-1h-pyrrole Chemical compound C=1C=C(C=2NC=CC=2)C=CC=1OC1=CC=CC=C1 IDYAYDHLGPEZAG-UHFFFAOYSA-N 0.000 description 1
- XDVZABUNTQTOMU-UHFFFAOYSA-N 2-(4-phenylsulfanylphenyl)-1h-pyrrole Chemical compound C=1C=C(C=2NC=CC=2)C=CC=1SC1=CC=CC=C1 XDVZABUNTQTOMU-UHFFFAOYSA-N 0.000 description 1
- JIAOXABVTMPZRF-UHFFFAOYSA-N 2-[4-(3-carbamimidoylphenoxy)phenyl]-1h-indole-6-carboximidamide Chemical compound NC(=N)C1=CC=CC(OC=2C=CC(=CC=2)C=2NC3=CC(=CC=C3C=2)C(N)=N)=C1 JIAOXABVTMPZRF-UHFFFAOYSA-N 0.000 description 1
- FXJNEGGDELALIX-UHFFFAOYSA-N 2-chloro-6-[4-(1-methylpyrazol-3-yl)phenoxy]benzonitrile Chemical compound CN1C=CC(C=2C=CC(OC=3C(=C(Cl)C=CC=3)C#N)=CC=2)=N1 FXJNEGGDELALIX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C07D207/34—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 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- 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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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EP (2) | EP2266960B1 (pt) |
JP (2) | JP4832647B2 (pt) |
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CN (1) | CN1353605A (pt) |
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AU (1) | AU782353B2 (pt) |
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MX (1) | MXPA01009655A (pt) |
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WO (1) | WO2000057877A1 (pt) |
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US7517880B2 (en) * | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
JP2002534468A (ja) | 1999-01-13 | 2002-10-15 | バイエル コーポレイション | p38キナーゼ阻害剤としてのω−カルボキシアリール置換ジフェニル尿素 |
EP1169060B1 (en) * | 1999-04-09 | 2005-08-31 | Euro-Celtique S.A. | Sodium channel blocker compositions and the use thereof |
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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2000
- 2000-03-24 BR BR0009322-0A patent/BR0009322A/pt not_active IP Right Cessation
- 2000-03-24 AT AT00919636T patent/ATE467620T1/de active
- 2000-03-24 CN CN00806810A patent/CN1353605A/zh active Pending
- 2000-03-24 CZ CZ20013435A patent/CZ20013435A3/cs unknown
- 2000-03-24 CA CA002368631A patent/CA2368631A1/en not_active Abandoned
- 2000-03-24 AR ARP000101352A patent/AR023171A1/es unknown
- 2000-03-24 MX MXPA01009655A patent/MXPA01009655A/es not_active Application Discontinuation
- 2000-03-24 AU AU40291/00A patent/AU782353B2/en not_active Ceased
- 2000-03-24 RU RU2001129155/04A patent/RU2001129155A/ru not_active Application Discontinuation
- 2000-03-24 WO PCT/US2000/007944 patent/WO2000057877A1/en not_active Application Discontinuation
- 2000-03-24 EP EP10004963.4A patent/EP2266960B1/en not_active Expired - Lifetime
- 2000-03-24 PT PT00919636T patent/PT1173169E/pt unknown
- 2000-03-24 ES ES00919636T patent/ES2345921T3/es not_active Expired - Lifetime
- 2000-03-24 YU YU68701A patent/YU68701A/sh unknown
- 2000-03-24 HU HU0201314A patent/HUP0201314A3/hu unknown
- 2000-03-24 US US09/533,864 patent/US6414011B1/en not_active Expired - Lifetime
- 2000-03-24 TR TR2001/02790T patent/TR200102790T2/xx unknown
- 2000-03-24 JP JP2000607628A patent/JP4832647B2/ja not_active Expired - Fee Related
- 2000-03-24 NZ NZ514756A patent/NZ514756A/en unknown
- 2000-03-24 PL PL00351439A patent/PL351439A1/xx not_active Application Discontinuation
- 2000-03-24 IL IL14550800A patent/IL145508A0/xx unknown
- 2000-03-24 KR KR1020017012292A patent/KR20020015308A/ko not_active Application Discontinuation
- 2000-03-24 UA UA2001107227A patent/UA72244C2/uk unknown
- 2000-03-24 DE DE60044395T patent/DE60044395D1/de not_active Expired - Lifetime
- 2000-03-24 DK DK00919636.1T patent/DK1173169T3/da active
- 2000-03-24 DE DE20080291U patent/DE20080291U1/de not_active Expired - Lifetime
- 2000-03-24 TW TW089105616A patent/TW502019B/zh not_active IP Right Cessation
- 2000-03-24 EP EP00919636A patent/EP1173169B1/en not_active Expired - Lifetime
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2001
- 2001-09-25 NO NO20014659A patent/NO20014659L/no not_active Application Discontinuation
- 2001-10-25 ZA ZA200108807A patent/ZA200108807B/en unknown
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2002
- 2002-04-30 US US10/134,697 patent/US6737418B2/en not_active Expired - Lifetime
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2003
- 2003-11-21 NZ NZ529690A patent/NZ529690A/en unknown
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2010
- 2010-08-10 CY CY20101100744T patent/CY1111163T1/el unknown
- 2010-09-29 JP JP2010220062A patent/JP2011021028A/ja not_active Withdrawn
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