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
Links
- 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
- FGONIWBIKVGBNI-UHFFFAOYSA-N 2-chloro-6-[4-(1h-pyrazol-5-yl)phenoxy]benzonitrile Chemical compound ClC1=CC=CC(OC=2C=CC(=CC=2)C=2NN=CC=2)=C1C#N FGONIWBIKVGBNI-UHFFFAOYSA-N 0.000 description 1
- RXXSZJFXWNLGOG-UHFFFAOYSA-N 2-chloro-6-[4-(2-methylpyrazol-3-yl)phenoxy]benzonitrile Chemical compound CN1N=CC=C1C(C=C1)=CC=C1OC1=CC=CC(Cl)=C1C#N RXXSZJFXWNLGOG-UHFFFAOYSA-N 0.000 description 1
- WHPKLODXZPEAJU-UHFFFAOYSA-N 3-methylsulfanyl-5-(4-phenoxyphenyl)-1h-pyrazole Chemical compound N1N=C(SC)C=C1C(C=C1)=CC=C1OC1=CC=CC=C1 WHPKLODXZPEAJU-UHFFFAOYSA-N 0.000 description 1
- WWKHQSUDPSLVLO-UHFFFAOYSA-N 5-(4-phenoxyphenyl)-2-(trifluoromethyl)-1h-pyrrole-3-carbonitrile Chemical compound N#CC1=C(C(F)(F)F)NC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 WWKHQSUDPSLVLO-UHFFFAOYSA-N 0.000 description 1
- DQUCWLYNWVXPCI-UHFFFAOYSA-N 5-[4-(4-methoxyphenoxy)phenyl]-1h-pyrazole Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C=2NN=CC=2)C=C1 DQUCWLYNWVXPCI-UHFFFAOYSA-N 0.000 description 1
- XJWFRGPZAYEUPI-UHFFFAOYSA-N 5-[4-(4-nitrophenoxy)phenyl]-1h-pyrazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C=2NN=CC=2)C=C1 XJWFRGPZAYEUPI-UHFFFAOYSA-N 0.000 description 1
- XPGMZNVJAVQMEM-UHFFFAOYSA-N 5-[4-(benzenesulfonyl)phenyl]-1h-pyrazole Chemical compound C=1C=C(C=2NN=CC=2)C=CC=1S(=O)(=O)C1=CC=CC=C1 XPGMZNVJAVQMEM-UHFFFAOYSA-N 0.000 description 1
- HKKRHZMLSAJFLX-UHFFFAOYSA-N 5-methylsulfanyl-3-(4-phenoxyphenyl)-n-phenylpyrazole-1-carboxamide Chemical compound CSC1=CC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=NN1C(=O)NC1=CC=CC=C1 HKKRHZMLSAJFLX-UHFFFAOYSA-N 0.000 description 1
- PICGFWNZMBAHHC-UHFFFAOYSA-N 5-morpholin-4-yl-3-(4-phenoxyphenyl)-n-phenylpyrazole-1-carboxamide Chemical compound N1=C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)C=C(N2CCOCC2)N1C(=O)NC1=CC=CC=C1 PICGFWNZMBAHHC-UHFFFAOYSA-N 0.000 description 1
- OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 241000208822 Lactuca Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 101100010166 Mus musculus Dok3 gene Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000028389 Nerve injury Diseases 0.000 description 1
- 101710138657 Neurotoxin Proteins 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- FTALBRSUTCGOEG-UHFFFAOYSA-N Riluzole Chemical group C1=C(OC(F)(F)F)C=C2SC(N)=NC2=C1 FTALBRSUTCGOEG-UHFFFAOYSA-N 0.000 description 1
- PDOCBJADCWMDGL-UHFFFAOYSA-N Sipatrigine Chemical compound C1CN(C)CCN1C1=NC=C(C=2C(=C(Cl)C=C(Cl)C=2)Cl)C(N)=N1 PDOCBJADCWMDGL-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003282 amino acid receptor affecting agent Substances 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000001833 anti-estrogenic effect Effects 0.000 description 1
- 230000003509 anti-fertility effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229960003150 bupivacaine Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 231100000318 excitotoxic Toxicity 0.000 description 1
- 230000003492 excitotoxic effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 239000003825 glutamate receptor antagonist Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940043355 kinase inhibitor Drugs 0.000 description 1
- HTDFEXRUDGWNHA-UHFFFAOYSA-N lifarizine Chemical compound CC=1NC(C=2C=CC(C)=CC=2)=NC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 HTDFEXRUDGWNHA-UHFFFAOYSA-N 0.000 description 1
- 229950003413 lifarizine Drugs 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000003475 metalloproteinase inhibitor Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 230000008764 nerve damage Effects 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 description 1
- 229960000203 propafenone Drugs 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 229960004181 riluzole Drugs 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- A61P23/02—Local anaesthetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
- 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
-
- 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
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- 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
- C07D263/34—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 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
-
- 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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Anesthesiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12655399P | 1999-03-26 | 1999-03-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200108807B true ZA200108807B (en) | 2002-10-25 |
Family
ID=22425462
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200108807A ZA200108807B (en) | 1999-03-26 | 2001-10-25 | Aryl substituted pyrazoles, imidazoles, oxazoles, thiazoles and pyrroles, and the use thereof. |
Country Status (29)
Country | Link |
---|---|
US (2) | US6414011B1 (uk) |
EP (2) | EP1173169B1 (uk) |
JP (2) | JP4832647B2 (uk) |
KR (1) | KR20020015308A (uk) |
CN (1) | CN1353605A (uk) |
AR (1) | AR023171A1 (uk) |
AT (1) | ATE467620T1 (uk) |
AU (1) | AU782353B2 (uk) |
BR (1) | BR0009322A (uk) |
CA (1) | CA2368631A1 (uk) |
CY (1) | CY1111163T1 (uk) |
CZ (1) | CZ20013435A3 (uk) |
DE (2) | DE20080291U1 (uk) |
DK (1) | DK1173169T3 (uk) |
ES (1) | ES2345921T3 (uk) |
HU (1) | HUP0201314A3 (uk) |
IL (1) | IL145508A0 (uk) |
MX (1) | MXPA01009655A (uk) |
NO (1) | NO20014659L (uk) |
NZ (2) | NZ514756A (uk) |
PL (1) | PL351439A1 (uk) |
PT (1) | PT1173169E (uk) |
RU (1) | RU2001129155A (uk) |
TR (1) | TR200102790T2 (uk) |
TW (1) | TW502019B (uk) |
UA (1) | UA72244C2 (uk) |
WO (1) | WO2000057877A1 (uk) |
YU (1) | YU68701A (uk) |
ZA (1) | ZA200108807B (uk) |
Families Citing this family (116)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
EP2298311B1 (en) | 1999-01-13 | 2012-05-09 | Bayer HealthCare LLC | w-Carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors |
WO2000061188A1 (en) * | 1999-04-09 | 2000-10-19 | 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 |
AR029489A1 (es) | 2000-03-10 | 2003-07-02 | Euro Celtique Sa | Piridinas, pirimidinas, pirazinas, triazinas sustituidas por arilo, composiciones farmaceuticas y el uso de las mismas para la manufactura de un medicamento |
CN1321112C (zh) | 2000-03-24 | 2007-06-13 | 欧洲凯尔特股份有限公司 | 作为钠通道阻滞剂的芳基取代的吡唑、三唑和四唑化合物 |
US6335354B2 (en) | 2000-03-31 | 2002-01-01 | Cocensys Inc. | Aminopyridines and methods of using thereof |
FR2818978B1 (fr) * | 2000-12-28 | 2003-02-28 | Sod Conseils Rech Applic | Modulateurs de canaux sodiques derives de 2-piperidylimidazoles |
TWI248438B (en) * | 2001-04-10 | 2006-02-01 | Sod Conseils Rech Applic | Derivatives of heterocycles with 5 members, their preparation and their use as medicaments |
FR2825926A1 (fr) | 2001-06-14 | 2002-12-20 | Sod Conseils Rech Applic | Derives d'imidazoles modulant les canaux sodiques |
US7169782B2 (en) * | 2001-07-16 | 2007-01-30 | Euro-Celtique S.A. | Aryl substituted thiazolidinones and the use thereof |
AU2002333374B2 (en) | 2001-09-03 | 2007-03-22 | Newron Pharmaceuticals S.P.A. | Pharmaceutical composition comprising gabapentin or an analogue thereof and an (alpha)- aminoamide and its analgesic use |
AR037233A1 (es) | 2001-09-07 | 2004-11-03 | Euro Celtique Sa | Piridinas aril sustituidas, composiciones farmaceuticas y el uso de dichos compuestos para la elaboracion de un medicamento |
AR036873A1 (es) | 2001-09-07 | 2004-10-13 | Euro Celtique Sa | Piridinas aril sustituidas a, composiciones farmaceuticas y el uso de las mismas para la preparacion de un medicamento |
WO2003068228A1 (en) | 2002-02-11 | 2003-08-21 | Bayer Pharmaceuticals Corporation | Aryl ureas with angiogenesis inhibiting activity |
BR0308451A (pt) * | 2002-03-13 | 2005-01-11 | Euro Celtique Sa | Composto, composição farmacêutica, métodos para o tratamento, prevenção ou melhoria de disfunção e método de fabricação de composto |
EA200500289A1 (ru) * | 2002-07-31 | 2005-06-30 | Еуро-Селтик С. А. | Арилзамещенные бензимидазолы и их использование в качестве блокаторов натриевых каналов |
EP1438956A1 (en) * | 2003-01-16 | 2004-07-21 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful as antimigraine agents |
UY28213A1 (es) | 2003-02-28 | 2004-09-30 | Bayer Pharmaceuticals Corp | Nuevos derivados de cianopiridina útiles en el tratamiento de cáncer y otros trastornos. |
MY142651A (en) | 2003-03-18 | 2010-12-15 | Merck Sharp & Dohme | Biaryl substituted triazoles as sodium channel blockers |
EP1636585B2 (en) | 2003-05-20 | 2012-06-13 | Bayer HealthCare LLC | Diaryl ureas with kinase inhibiting activity |
ATE313532T1 (de) | 2003-07-22 | 2006-01-15 | Arena Pharm Inc | Diaryl- und arylheteroarylharnstoffderivate als modulatoren des 5-ht2a-serotoninrezeptors, die sich zur prophylaxe und behandlung von damit im zusammenhang stehenden erkrankungen eignen |
ME00294B (me) | 2003-07-23 | 2011-05-10 | Bayer Pharmaceuticals Corp | Fluoro supstituisana omega-karaboksiaril difenil urea za liječenje i prevenciju bolesti i stanja bolesti |
PL3002283T3 (pl) | 2003-12-26 | 2017-10-31 | Kyowa Hakko Kirin Co Ltd | Pochodne tiazolu |
CN1926114B (zh) | 2004-03-23 | 2011-08-24 | 艾尼纳制药公司 | 用于制备经取代n-芳基-n′-′3-(1h-吡唑-5-基)苯基脲及其中间体的方法 |
US20060084695A1 (en) * | 2004-04-29 | 2006-04-20 | John Griffin | 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 |
US7183285B2 (en) * | 2004-04-29 | 2007-02-27 | Pharmix Corp. | 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 |
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 |
SA05260357B1 (ar) | 2004-11-19 | 2008-09-08 | ارينا فارماسيتو تيكالز ، أنك | مشتقات 3_فينيل_بيرازول كمعدلات لمستقبل سيروتينين 5_ht2a مفيدة في علاج الاضطرابات المتعلقه به |
US20060111436A1 (en) * | 2004-11-23 | 2006-05-25 | John Griffin | Compositions and treatments for modulating kinase and/or HMG-CoA reductase |
KR20060087386A (ko) | 2005-01-28 | 2006-08-02 | 주식회사 대웅제약 | 신규 벤조이미다졸 유도체 및 이를 함유하는 약제학적조성물 |
WO2006137527A1 (ja) | 2005-06-23 | 2006-12-28 | Kyowa Hakko Kogyo Co., Ltd. | チアゾール誘導体 |
PE20070182A1 (es) | 2005-07-29 | 2007-03-06 | Wyeth Corp | Derivados cianopirrol-fenil amida como moduladores del receptor de progesterona |
CA2661448A1 (en) | 2005-08-25 | 2007-03-01 | Steven Michael Weiss | Reducing myocardial damage and the incidence of arrhythmia arising from loss, reduction or interruption in coronary blood flow |
ATE472529T1 (de) | 2005-10-10 | 2010-07-15 | Glaxo Group Ltd | Prolinamidderivate als natriumkanalmodulatoren |
TW200730494A (en) | 2005-10-10 | 2007-08-16 | Glaxo Group Ltd | Novel compounds |
TW200728258A (en) | 2005-10-10 | 2007-08-01 | Glaxo Group Ltd | Novel compounds |
CA2632030A1 (en) * | 2005-12-15 | 2007-06-21 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
DK1963280T3 (en) | 2005-12-22 | 2015-12-14 | Newron Pharm Spa | 2-phenylethylamine derivatives by calcium and / or sodium channel |
CA2646076C (en) | 2006-05-18 | 2015-06-30 | Arena Pharmaceuticals, Inc. | Ethers, secondary amines and derivatives thereof as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
USRE45336E1 (en) | 2006-05-18 | 2015-01-13 | Arena Pharmaceuticals, Inc. | Primary amines and derivatives thereof as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto |
MX2008014622A (es) | 2006-05-18 | 2008-11-28 | Arena Pharm Inc | Formas cristalinas y procesos para la preparacion de fenil-pirazoles utiles como moduladores del receptor de serotonina 5-ht2a. |
JP5448164B2 (ja) * | 2006-07-28 | 2014-03-19 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Cb2受容体を変調する化合物 |
EP2436750A3 (en) * | 2006-09-01 | 2014-08-20 | Pleotint, L.L.C. | Ligand exchange thermochromic, (LETC), systems |
US7928123B2 (en) * | 2006-09-25 | 2011-04-19 | Boehringer Ingelheim International Gmbh | Compounds which modulate the CB2 receptor |
TWI415845B (zh) | 2006-10-03 | 2013-11-21 | Arena Pharm Inc | 用於治療與5-ht2a血清素受體相關聯病症之作為5-ht2a血清素受體之調節劑的吡唑衍生物 |
EP1969934A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | 4-Cycloalkyl-oder 4-arylsubstituierte Phenoxyphenylamidine und deren Verwendung als Fungizide |
EP2155260A1 (en) * | 2007-06-14 | 2010-02-24 | Hammersmith Imanet, Ltd | Measurement of neural activity |
ES2421237T7 (es) | 2007-08-15 | 2013-09-30 | Arena Pharmaceuticals, Inc. | Derivados de imidazo[1,2-a]piridin como moduladores del receptor serotoninérgico 5ht2a en el tratamiento de trastornos relacionados con el mismo |
WO2009061652A1 (en) * | 2007-11-07 | 2009-05-14 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
WO2009123714A2 (en) | 2008-04-02 | 2009-10-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
JP5749162B2 (ja) * | 2008-07-10 | 2015-07-15 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Cb2受容体を調節するスルホン化合物 |
AP2011005674A0 (en) | 2008-09-25 | 2011-04-30 | Boehringer Ingelheim Int | Sulfonyl compounds which selectively modulate the CB2 receptor. |
ES2666324T3 (es) | 2008-10-28 | 2018-05-04 | Arena Pharmaceuticals, Inc. | Composiciones de un modulador del receptor de serotonina 5-HT2A útiles para el tratamiento de trastornos relacionados con el mismo |
WO2010062321A1 (en) | 2008-10-28 | 2010-06-03 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2h-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)-urea and crystalline forms related thereto |
US8436036B2 (en) | 2009-04-24 | 2013-05-07 | Janssen R&D Ireland | Diaryl ethers |
US8299103B2 (en) * | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
WO2010147791A1 (en) | 2009-06-16 | 2010-12-23 | Boehringer Ingelheim International Gmbh | Azetidine 2 -carboxamide derivatives which modulate the cb2 receptor |
UY32826A (es) | 2009-08-04 | 2011-02-28 | Takeda Pharmaceutical | Compuestos heterocíclicos |
WO2011037795A1 (en) * | 2009-09-22 | 2011-03-31 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the cb2 receptor |
US8993612B2 (en) * | 2009-10-08 | 2015-03-31 | Rhizen Pharmaceuticals Sa | Modulators of calcium release-activated calcium channel and methods for treatment of non-small cell lung cancer |
US8980891B2 (en) | 2009-12-18 | 2015-03-17 | Arena Pharmaceuticals, Inc. | Crystalline forms of certain 3-phenyl-pyrazole derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto |
EP2523936A1 (en) | 2010-01-15 | 2012-11-21 | Boehringer Ingelheim International GmbH | Compounds which modulate the cb2 receptor |
DE102010007281A1 (de) * | 2010-02-08 | 2011-08-11 | EMC microcollections GmbH, 72070 | Neue Aminoalkyl-oxazol- und Aminoalkyl-thiazolcarbonsäureamide und ihre Anwendung zur Stimulation der endogenen situ Regeneration von Haarsinneszellen im Corti'schen Organ des Innenohres beim Säuger |
US8329735B2 (en) | 2010-03-05 | 2012-12-11 | Boehringer Ingelheim International Gmbh | Tetrazole compounds which selectively modulate the CB2 receptor |
EP2593434A1 (en) | 2010-07-16 | 2013-05-22 | Purdue Pharma LP | Pyridine compounds as sodium channel blockers |
EP2595959B1 (en) | 2010-07-22 | 2015-11-04 | Boehringer Ingelheim International GmbH | Sulfonyl compounds which modulate the cb2 receptor |
KR20130056345A (ko) | 2010-09-17 | 2013-05-29 | 퍼듀 퍼머 엘피 | 피리딘 화합물 및 그의 용도 |
CA2813704A1 (en) | 2010-10-05 | 2012-04-12 | Purdue Pharma L.P. | Quinazoline compounds as sodium channel blockers |
EP2655330B1 (en) | 2010-12-22 | 2016-02-10 | Purdue Pharma LP | Substituted pyridines as sodium channel blockers |
EP2753606B1 (en) | 2011-09-02 | 2017-07-05 | Purdue Pharma LP | Pyrimidines as sodium channel blockers |
WO2013064883A1 (en) | 2011-10-31 | 2013-05-10 | Purdue Pharma L.P. | Heteroaryl compounds as sodium channel blockers |
US9388137B2 (en) | 2011-10-31 | 2016-07-12 | Purdue Pharma L.P. | Quaternized amines as sodium channel blockers |
WO2013072758A1 (en) | 2011-11-15 | 2013-05-23 | Purdue Pharma L.P. | Pyrimidine diol amides as sodium channel blockers |
CN104203940B (zh) | 2011-12-28 | 2017-01-18 | 爱尔兰詹森科学公司 | 作为hcv抑制剂的杂双环衍生物 |
US9128307B2 (en) | 2012-02-20 | 2015-09-08 | Pleotint, L.L.C. | Enhanced thermochromic window which incorporates a film with multiple layers of alternating refractive index |
WO2013136170A1 (en) | 2012-03-16 | 2013-09-19 | Purdue Pharma L.P. | Substituted pyridines as sodium channel blockers |
EP3485880A1 (en) | 2012-04-17 | 2019-05-22 | Purdue Pharma LP | Systems and methods for treating an opioid-induced adverse pharmacodynamic response |
WO2014096941A1 (en) | 2012-12-20 | 2014-06-26 | Purdue Pharma L.P. | Cyclic sulfonamides as sodium channel blockers |
CA2941171C (en) | 2013-03-04 | 2020-07-07 | Purdue Pharma L.P. | Pyrimidine carboxamides as sodium channel blockers |
US9120786B2 (en) | 2013-03-04 | 2015-09-01 | Purdue Pharma, L.P. | Triazine carboxamides as sodium channel blockers |
JP6186494B2 (ja) | 2013-03-15 | 2017-08-23 | パーデュー、ファーマ、リミテッド、パートナーシップ | カルボキサミド誘導体及びその使用 |
EP2803668A1 (en) | 2013-05-17 | 2014-11-19 | Boehringer Ingelheim International Gmbh | Novel (cyano-dimethyl-methyl)-isoxazoles and -[1,3,4]thiadiazoles |
US9359330B2 (en) | 2013-08-26 | 2016-06-07 | Purdue Pharma L.P. | Substituted piperidines as sodium channel blockers |
US9884865B2 (en) | 2013-08-26 | 2018-02-06 | Purdue Pharma L.P. | Azaspiro[4.5] decane derivatives and use thereof |
US9828348B2 (en) | 2013-11-08 | 2017-11-28 | Purdue Pharma L.P. | Benzimidazole derivatives and use thereof |
US9340504B2 (en) | 2013-11-21 | 2016-05-17 | Purdue Pharma L.P. | Pyridine and piperidine derivatives as novel sodium channel blockers |
KR102423640B1 (ko) | 2013-12-20 | 2022-07-22 | 노파르티스 아게 | Lta4h 억제제로서의 헤테로아릴 부탄산 유도체 |
US9745287B2 (en) | 2013-12-20 | 2017-08-29 | Purdue Pharma L.P. | Pyrimidines and use thereof |
US9695144B2 (en) | 2013-12-23 | 2017-07-04 | Purdue Pharma L.P. | Dibenzazepine derivatives and use thereof |
WO2015099841A1 (en) * | 2013-12-23 | 2015-07-02 | Purdue Pharma L.P. | Indazoles and use thereof |
US9902726B2 (en) | 2013-12-30 | 2018-02-27 | Purdue Pharma L.P. | Pyridone-sulfone morphinan analogs as opioid receptor ligands |
JP6526023B2 (ja) | 2014-01-24 | 2019-06-05 | パーデュー、ファーマ、リミテッド、パートナーシップ | ピリジン類及びピリミジン類並びにその使用 |
CA2939501C (en) | 2014-02-12 | 2020-07-07 | Purdue Pharma L.P. | Isoquinoline derivatives and use thereof |
US10730866B2 (en) | 2014-04-07 | 2020-08-04 | Purdue Pharma L.P. | Indole derivatives and use thereof |
WO2015161011A1 (en) * | 2014-04-17 | 2015-10-22 | Merck Sharp & Dohme Corp. | Benzamide cgrp receptor antagonists |
MA39956A (fr) | 2014-05-06 | 2015-11-12 | Purdue Pharma Lp | Analogues du benzomorphane et leur utilisation |
WO2015192039A1 (en) | 2014-06-13 | 2015-12-17 | Purdue Pharma L.P. | Heterocyclic morphinan derivatives and use thereof |
CA2951697A1 (en) | 2014-06-13 | 2015-12-17 | Purdue Pharma L.P. | Azamophinan derivatives and use thereof |
US9849124B2 (en) | 2014-10-17 | 2017-12-26 | Purdue Pharma L.P. | Systems and methods for treating an opioid-induced adverse pharmacodynamic response |
ES2912881T3 (es) | 2014-12-23 | 2022-05-30 | Convergence Pharmaceuticals | Procedimiento para preparar derivados de alfa-carboxamida pirrolidina |
WO2016201373A1 (en) | 2015-06-12 | 2016-12-15 | Axovant Sciences Ltd. | Diaryl and arylheteroaryl urea derivatives useful for the prophylaxis and treatment of rem sleep behavior disorder |
CN108472285A (zh) | 2015-07-15 | 2018-08-31 | 阿速万科学有限责任公司 | 用于预防和治疗与神经退行性疾病相关联的幻觉的二芳基和芳基杂芳基脲衍生物 |
CN107118586A (zh) * | 2016-02-24 | 2017-09-01 | 中国科学技术大学 | 含氮杂环基取代的烯类化合物的用途 |
WO2017156495A1 (en) * | 2016-03-11 | 2017-09-14 | Corvus Pharmaceuticals, Inc. | Compounds and methods for modulating bruton's tyrosine kinase |
EP3573957B1 (en) | 2017-01-24 | 2023-04-26 | Rivara, Mirko | Compositions and methods for blocking sodium channels |
SG11202002706XA (en) | 2017-10-05 | 2020-04-29 | Biogen Inc | Process for preparing alpha-carboxamide pyrolidine derivatives |
US10707913B2 (en) * | 2018-09-04 | 2020-07-07 | Raytheon Company | Composable transceiver using low bit count inputs and outputs |
AR116754A1 (es) * | 2018-10-18 | 2021-06-09 | Sumitomo Chemical Co | Compuesto de fenilpirazol y método para controlar fitoenfermedades |
US20210393596A1 (en) * | 2018-10-26 | 2021-12-23 | University Of South Florida | Drug for treating tinnitus |
EP3903576A4 (en) * | 2018-12-25 | 2022-03-16 | Tokyo University of Science Foundation | JASMONIC ACID ENDOGENIC PROMOTER AND METHOD OF JASMONIC ACID ENDOGENIC PROMOTER |
CN111825658A (zh) * | 2019-04-18 | 2020-10-27 | 华东理工大学 | 新型egfr三突变抑制剂及其应用 |
Family Cites Families (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ178996A (en) | 1974-11-15 | 1978-06-02 | Kornis G | Pyrfazole amides and thioamides;herbicidal compositions |
JPS5975257A (ja) | 1982-10-23 | 1984-04-27 | Ricoh Co Ltd | 電子写真用感光体 |
DE3307364A1 (de) * | 1983-03-02 | 1984-09-06 | Hoechst Ag, 6230 Frankfurt | Zweikomponenten-diazontypiematerial |
DE3503773A1 (de) | 1985-02-05 | 1986-08-07 | Basf Ag, 6700 Ludwigshafen | Thiazolylamide, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
GB8624879D0 (en) | 1986-10-17 | 1986-11-19 | May & Baker Ltd | Compositions of matter |
US5015651A (en) * | 1988-01-07 | 1991-05-14 | E. I. Du Pont De Nemours And Company | Treatment of hypertension with 1,2,4-angiotensin II antagonists |
US5104960A (en) * | 1989-02-22 | 1992-04-14 | The Dow Chemical Company | Nucleophilic displacement method for synthesis of non-rigid PBZ polymers |
ATE134368T1 (de) | 1989-06-30 | 1996-03-15 | Du Pont | Substituierte imidazole und ihre verwendung als hemmmstoff fur angiotensin ii |
PH27357A (en) * | 1989-09-22 | 1993-06-21 | Fujisawa Pharmaceutical Co | Pyrazole derivatives and pharmaceutical compositions comprising the same |
GB9005028D0 (en) | 1990-03-06 | 1990-05-02 | Sandoz Ltd | Improvements in or relating to organic compounds |
JPH04164032A (ja) * | 1990-10-26 | 1992-06-09 | Mitsubishi Kasei Corp | 過酸化脂質生成抑制剤 |
JPH05287563A (ja) | 1992-04-07 | 1993-11-02 | Hideaki Yamaguchi | 金属の表面処理方法 |
EP0639567A1 (en) | 1992-05-08 | 1995-02-22 | Otsuka Pharmaceutical Factory, Inc. | Indole derivative |
JPH0725849A (ja) | 1993-07-08 | 1995-01-27 | Nippon Soda Co Ltd | 2−トリフルオロメチルピロール誘導体および製造方法 |
DE4325822A1 (de) * | 1993-07-31 | 1995-02-02 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
US5744492A (en) | 1993-09-17 | 1998-04-28 | United States Of America | Method for inhibiting angiogenesis |
US5602156A (en) | 1993-09-17 | 1997-02-11 | The United States Of America As Represented By The Department Of Health And Human Services | Method for inhibiting metalloproteinase expression |
US6057346A (en) | 1994-12-12 | 2000-05-02 | The United States Of America As Represented By The Department Of Health And Human Services | Inhibition of retroviral LTR promoters by calcium response modifiers |
GB9503946D0 (en) * | 1995-02-28 | 1995-04-19 | Cancer Res Campaign Tech | Benzazole compounds |
US5741818A (en) | 1995-06-07 | 1998-04-21 | University Of Saskatchewan | Semicarbazones having CNS activity and pharmaceutical preparations containing same |
WO1997011946A1 (fr) * | 1995-09-28 | 1997-04-03 | Otsuka Pharmaceutical Factory, Inc. | Analgesiques |
EP0973513A4 (en) * | 1996-10-23 | 2003-03-19 | Zymogenetics Inc | COMPOSITIONS AND METHODS FOR TREATING CONDITIONS ASSOCIATED WITH BONE DEFICIT |
JP4039707B2 (ja) | 1996-12-03 | 2008-01-30 | 株式会社エス・ディー・エス バイオテック | 置換ピラゾール誘導体、その製造方法およびその誘導体を有効成分とする農園芸用殺菌剤 |
US5925654A (en) * | 1997-03-12 | 1999-07-20 | G.D. Searle & Co. | LTA4 , hydrolase inhibitors |
WO1998050348A1 (en) | 1997-05-09 | 1998-11-12 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses |
BR9809147A (pt) | 1997-05-22 | 2000-08-01 | Searle & Co | Composto pirazol substituìdo, composição farmacêutica, processos para tratar um distúrbio mediado por tnf, um distúrbio mediado por quinase p38, inflamação e artrite, e, para preparar pirazóis |
US6294536B1 (en) * | 1997-08-29 | 2001-09-25 | Takeda Schering-Plough Animal Health K.K. | Triazine derivatives, their production and use |
US5942532A (en) | 1997-09-05 | 1999-08-24 | Ortho Pharmaceutical Corporation | 2-substituted phenyl-benzimidazole antibacterial agents |
JP4385414B2 (ja) * | 1997-10-13 | 2009-12-16 | アステラス製薬株式会社 | アミド若しくはアミン誘導体 |
ATE292465T1 (de) * | 1998-05-22 | 2005-04-15 | Avanir Pharmaceuticals | Benzimidazol-derivate als ige-modulatoren |
JP2000109465A (ja) * | 1998-08-05 | 2000-04-18 | Nippon Soda Co Ltd | フェニルピラゾ―ル化合物、製法及び抗高脂血症薬 |
KR20010086005A (ko) * | 1998-11-06 | 2001-09-07 | 스타르크, 카르크 | 트리사이클릭 피라졸 유도체 |
-
2000
- 2000-03-24 IL IL14550800A patent/IL145508A0/xx unknown
- 2000-03-24 HU HU0201314A patent/HUP0201314A3/hu unknown
- 2000-03-24 BR BR0009322-0A patent/BR0009322A/pt not_active IP Right Cessation
- 2000-03-24 WO PCT/US2000/007944 patent/WO2000057877A1/en not_active Application Discontinuation
- 2000-03-24 YU YU68701A patent/YU68701A/sh unknown
- 2000-03-24 ES ES00919636T patent/ES2345921T3/es not_active Expired - Lifetime
- 2000-03-24 NZ NZ514756A patent/NZ514756A/en unknown
- 2000-03-24 US US09/533,864 patent/US6414011B1/en not_active Expired - Lifetime
- 2000-03-24 JP JP2000607628A patent/JP4832647B2/ja not_active Expired - Fee Related
- 2000-03-24 DE DE20080291U patent/DE20080291U1/de not_active Expired - Lifetime
- 2000-03-24 DE DE60044395T patent/DE60044395D1/de not_active Expired - Lifetime
- 2000-03-24 CA CA002368631A patent/CA2368631A1/en not_active Abandoned
- 2000-03-24 EP EP00919636A patent/EP1173169B1/en not_active Expired - Lifetime
- 2000-03-24 DK DK00919636.1T patent/DK1173169T3/da active
- 2000-03-24 EP EP10004963.4A patent/EP2266960B1/en not_active Expired - Lifetime
- 2000-03-24 UA UA2001107227A patent/UA72244C2/uk unknown
- 2000-03-24 PT PT00919636T patent/PT1173169E/pt unknown
- 2000-03-24 TW TW089105616A patent/TW502019B/zh not_active IP Right Cessation
- 2000-03-24 MX MXPA01009655A patent/MXPA01009655A/es not_active Application Discontinuation
- 2000-03-24 KR KR1020017012292A patent/KR20020015308A/ko not_active Application Discontinuation
- 2000-03-24 RU RU2001129155/04A patent/RU2001129155A/ru not_active Application Discontinuation
- 2000-03-24 AT AT00919636T patent/ATE467620T1/de active
- 2000-03-24 AU AU40291/00A patent/AU782353B2/en not_active Ceased
- 2000-03-24 AR ARP000101352A patent/AR023171A1/es unknown
- 2000-03-24 CZ CZ20013435A patent/CZ20013435A3/cs unknown
- 2000-03-24 CN CN00806810A patent/CN1353605A/zh active Pending
- 2000-03-24 PL PL00351439A patent/PL351439A1/xx not_active Application Discontinuation
- 2000-03-24 TR TR2001/02790T patent/TR200102790T2/xx unknown
-
2001
- 2001-09-25 NO NO20014659A patent/NO20014659L/no not_active Application Discontinuation
- 2001-10-25 ZA ZA200108807A patent/ZA200108807B/en unknown
-
2002
- 2002-04-30 US US10/134,697 patent/US6737418B2/en not_active Expired - Lifetime
-
2003
- 2003-11-21 NZ NZ529690A patent/NZ529690A/en unknown
-
2010
- 2010-08-10 CY CY20101100744T patent/CY1111163T1/el unknown
- 2010-09-29 JP JP2010220062A patent/JP2011021028A/ja not_active Withdrawn
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200108807B (en) | Aryl substituted pyrazoles, imidazoles, oxazoles, thiazoles and pyrroles, and the use thereof. | |
JP2002540155A5 (uk) | ||
EP0324377B1 (en) | Angiotensin II receptor blocking imidazoles and combinations thereof with diuretics and NSaids | |
US7531560B2 (en) | Anti-cytokine heterocyclic compounds | |
US6699887B2 (en) | Anti-HIV pyrazole derivatives | |
US8367710B2 (en) | Bicyclo-substituted pyrazolon azo derivatives, preparation process and pharmaceutical use thereof | |
HRP20170019T1 (hr) | Novi pirol-inhibitori od reduktaze s-nitrozoglutationa kao terapeutska sredstva | |
SK174699A3 (en) | Inhibitors of factor xa with a neutral p1 specificity group | |
JP2010513272A5 (uk) | ||
KR20100047901A (ko) | 암 및 건선 치료에 유용한 복소환 아미드 | |
CA2684105A1 (en) | Pyridine derivatives | |
MX2013001363A (es) | N- ((6-amino-piridin-3-il)-metil) -heteroaril-carboxamidas como inhibidoras de calicreina de plasma. | |
ZA200208226B (en) | Aminopyridines and their use as anticonvulsants and sodium channel blockers. | |
SI2513053T1 (en) | Pyrrolidine carboxylic acid derivatives as G-protein-coupled receptor 43 agonists (GPR43), pharmaceutical composition and methods for use in the treatment of metabolic disorders | |
PL193802B1 (pl) | Zastosowanie pochodnych arylo (lub heteroarylo) azolilokarbinoli do wytwarzania leku do leczenia zaburzeń wywoływanych nadmiarem substancji P | |
EP0733366B1 (en) | Pharmaceutical compositions comprising angiotensin II receptor blocking imidazoles and diuretics | |
CA2521227A1 (en) | Substituted pyrazole compounds | |
TH70502B (th) | อนุพันธ์ต่างๆ ของไพราโซลสำหรับการบำบัด hiv | |
TH115312A (th) | อนุพันธ์ต่างๆ ของไพราโซลสำหรับการบำบัด hiv | |
CZ444399A3 (cs) | Inhibitory faktoru Xa s neutrální Pl skupinovou specifičností |