JP2002540155A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2002540155A5 JP2002540155A5 JP2000607628A JP2000607628A JP2002540155A5 JP 2002540155 A5 JP2002540155 A5 JP 2002540155A5 JP 2000607628 A JP2000607628 A JP 2000607628A JP 2000607628 A JP2000607628 A JP 2000607628A JP 2002540155 A5 JP2002540155 A5 JP 2002540155A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- hydrogen
- phenyl
- fifteen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 description 68
- 229910052739 hydrogen Inorganic materials 0.000 description 59
- -1 cyano, amino Chemical group 0.000 description 58
- 239000001257 hydrogen Substances 0.000 description 56
- 150000001875 compounds Chemical class 0.000 description 53
- 150000002431 hydrogen Chemical class 0.000 description 48
- 125000000753 cycloalkyl group Chemical group 0.000 description 32
- 125000003342 alkenyl group Chemical group 0.000 description 29
- 125000000304 alkynyl group Chemical group 0.000 description 29
- 125000000623 heterocyclic group Chemical group 0.000 description 29
- 125000001072 heteroaryl group Chemical group 0.000 description 28
- 125000003118 aryl group Chemical group 0.000 description 27
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 20
- 125000004103 aminoalkyl group Chemical group 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 125000004181 carboxyalkyl group Chemical group 0.000 description 20
- 125000001188 haloalkyl group Chemical group 0.000 description 20
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 20
- 229910052760 oxygen Inorganic materials 0.000 description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
- 229910052717 sulfur Inorganic materials 0.000 description 20
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 19
- 125000003282 alkyl amino group Chemical group 0.000 description 18
- 125000003710 aryl alkyl group Chemical group 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 17
- 125000004093 cyano group Chemical group *C#N 0.000 description 17
- 239000000651 prodrug Substances 0.000 description 17
- 229940002612 prodrug Drugs 0.000 description 17
- 239000012453 solvate Substances 0.000 description 17
- 125000003545 alkoxy group Chemical group 0.000 description 16
- 125000005018 aryl alkenyl group Chemical group 0.000 description 16
- 125000005843 halogen group Chemical group 0.000 description 15
- 150000003573 thiols Chemical class 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 14
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 12
- 150000001408 amides Chemical class 0.000 description 12
- 125000004663 dialkyl amino group Chemical group 0.000 description 12
- 125000000547 substituted alkyl group Chemical group 0.000 description 12
- 125000004442 acylamino group Chemical group 0.000 description 11
- 125000004423 acyloxy group Chemical group 0.000 description 11
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 11
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 10
- 125000004414 alkyl thio group Chemical group 0.000 description 10
- 125000005015 aryl alkynyl group Chemical group 0.000 description 10
- 150000001540 azides Chemical class 0.000 description 10
- 125000002837 carbocyclic group Chemical group 0.000 description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 9
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 description 9
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 8
- 125000006323 alkenyl amino group Chemical group 0.000 description 8
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 description 8
- 125000005100 aryl amino carbonyl group Chemical group 0.000 description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 8
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 208000002193 Pain Diseases 0.000 description 5
- 150000001356 alkyl thiols Chemical class 0.000 description 5
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 5
- 125000004447 heteroarylalkenyl group Chemical group 0.000 description 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 5
- 125000005312 heteroarylalkynyl group Chemical group 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 206010010904 Convulsion Diseases 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 0 Cc1c(*)c(*)c(*c2c(*)c(*)c(*)c(*)c2*)c(*)c1O* Chemical compound Cc1c(*)c(*)c(*c2c(*)c(*)c(*)c(*)c2*)c(*)c1O* 0.000 description 3
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical class N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 206010026749 Mania Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 108010052164 Sodium Channels Proteins 0.000 description 2
- 102000018674 Sodium Channels Human genes 0.000 description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002690 local anesthesia Methods 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 230000000626 neurodegenerative effect Effects 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- VKBOFLKFVJNVON-UHFFFAOYSA-N 1-[3-[4-(4-nitrophenoxy)phenyl]pyrazol-1-yl]ethanone Chemical compound CC(=O)N1C=CC(C=2C=CC(OC=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)=N1 VKBOFLKFVJNVON-UHFFFAOYSA-N 0.000 description 1
- JUTGEKQFBMEDCR-UHFFFAOYSA-N 1-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound CC(C)(O)CN1N=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 JUTGEKQFBMEDCR-UHFFFAOYSA-N 0.000 description 1
- CIOBKBATFFYLPA-UHFFFAOYSA-N 1-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]propan-2-one Chemical compound CC(=O)CN1N=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 CIOBKBATFFYLPA-UHFFFAOYSA-N 0.000 description 1
- LFABDKAVGRGBKB-UHFFFAOYSA-N 1-benzyl-5-[4-(4-fluorophenoxy)phenyl]pyrazole Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2N(N=CC=2)CC=2C=CC=CC=2)C=C1 LFABDKAVGRGBKB-UHFFFAOYSA-N 0.000 description 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 1
- LJWPODFBXNZRNJ-UHFFFAOYSA-N 2-[3-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]acetamide Chemical compound NC(=O)CN1C=CC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 LJWPODFBXNZRNJ-UHFFFAOYSA-N 0.000 description 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 description 1
- BIWLLWXBQCQLGG-UHFFFAOYSA-N 2-[3-[4-[4-(trifluoromethyl)phenoxy]phenyl]pyrazol-1-yl]pyrimidine Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1=CC=C(C2=NN(C=C2)C=2N=CC=CN=2)C=C1 BIWLLWXBQCQLGG-UHFFFAOYSA-N 0.000 description 1
- RYBGVNFVNQDALX-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenyl]-1,3-oxazole-4-carboxamide Chemical compound NC(=O)C1=COC(C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=N1 RYBGVNFVNQDALX-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 1
- ABCFFRHJLNZMLK-UHFFFAOYSA-N 2-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]-1-morpholin-4-ylethanone Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2N(N=CC=2)CC(=O)N2CCOCC2)C=C1 ABCFFRHJLNZMLK-UHFFFAOYSA-N 0.000 description 1
- KDGBSQOBDISXJY-UHFFFAOYSA-N 2-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2N(N=CC=2)CC(=O)N2CCCC2)C=C1 KDGBSQOBDISXJY-UHFFFAOYSA-N 0.000 description 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 description 1
- QGYHMLTWZSJCMM-UHFFFAOYSA-N 2-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]ethanol Chemical compound OCCN1N=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 QGYHMLTWZSJCMM-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 1
- OYOZIANRHNFTPI-UHFFFAOYSA-N 3-[4-(2,4-difluorophenoxy)phenyl]pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC(C=2C=CC(OC=3C(=CC(F)=CC=3)F)=CC=2)=N1 OYOZIANRHNFTPI-UHFFFAOYSA-N 0.000 description 1
- DWURZDHXVIRXAE-UHFFFAOYSA-N 3-[4-(2-chloro-4-fluorophenoxy)phenyl]pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC(C=2C=CC(OC=3C(=CC(F)=CC=3)Cl)=CC=2)=N1 DWURZDHXVIRXAE-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 1
- FMGBXNGBWPWGEK-UHFFFAOYSA-N 5-[4-(4-fluorophenoxy)phenyl]-1h-imidazole Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C=2N=CNC=2)C=C1 FMGBXNGBWPWGEK-UHFFFAOYSA-N 0.000 description 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 description 1
- IFERTYSUNNLIOC-UHFFFAOYSA-N 5-[4-(4-fluorophenoxy)phenyl]-1h-pyrrole-2-carboxamide Chemical compound N1C(C(=O)N)=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 IFERTYSUNNLIOC-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 1
- 208000000094 Chronic Pain 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
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- AYFUNGMLUBOVCL-UHFFFAOYSA-N n-[2-[5-[4-(4-fluorophenoxy)phenyl]pyrazol-1-yl]ethyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCN1N=CC=C1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 AYFUNGMLUBOVCL-UHFFFAOYSA-N 0.000 description 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 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12655399P | 1999-03-26 | 1999-03-26 | |
| US60/126,553 | 1999-03-26 | ||
| PCT/US2000/007944 WO2000057877A1 (en) | 1999-03-26 | 2000-03-24 | Aryl substituted pyrazoles, imidazoles, oxazoles, thiazoles and pyrroles, and the use thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010220062A Division JP2011021028A (ja) | 1999-03-26 | 2010-09-29 | アリール置換ピラゾール、イミダゾール、オキサゾール、チアゾールおよびピロール、ならびにそれらの使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002540155A JP2002540155A (ja) | 2002-11-26 |
| JP2002540155A5 true JP2002540155A5 (https=) | 2007-05-24 |
| JP4832647B2 JP4832647B2 (ja) | 2011-12-07 |
Family
ID=22425462
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000607628A Expired - Fee Related JP4832647B2 (ja) | 1999-03-26 | 2000-03-24 | アリール置換ピラゾール、イミダゾール、オキサゾール、チアゾールおよびピロール、ならびにそれらの使用 |
| JP2010220062A Withdrawn JP2011021028A (ja) | 1999-03-26 | 2010-09-29 | アリール置換ピラゾール、イミダゾール、オキサゾール、チアゾールおよびピロール、ならびにそれらの使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010220062A Withdrawn JP2011021028A (ja) | 1999-03-26 | 2010-09-29 | アリール置換ピラゾール、イミダゾール、オキサゾール、チアゾールおよびピロール、ならびにそれらの使用 |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US6414011B1 (https=) |
| EP (2) | EP2266960B1 (https=) |
| JP (2) | JP4832647B2 (https=) |
| KR (1) | KR20020015308A (https=) |
| CN (1) | CN1353605A (https=) |
| AR (1) | AR023171A1 (https=) |
| AT (1) | ATE467620T1 (https=) |
| AU (1) | AU782353B2 (https=) |
| BR (1) | BR0009322A (https=) |
| CA (1) | CA2368631A1 (https=) |
| CY (1) | CY1111163T1 (https=) |
| CZ (1) | CZ20013435A3 (https=) |
| DE (2) | DE60044395D1 (https=) |
| DK (1) | DK1173169T3 (https=) |
| ES (1) | ES2345921T3 (https=) |
| HU (1) | HUP0201314A3 (https=) |
| IL (1) | IL145508A0 (https=) |
| MX (1) | MXPA01009655A (https=) |
| NO (1) | NO20014659L (https=) |
| NZ (2) | NZ514756A (https=) |
| PL (1) | PL351439A1 (https=) |
| PT (1) | PT1173169E (https=) |
| RU (1) | RU2001129155A (https=) |
| TR (1) | TR200102790T2 (https=) |
| TW (1) | TW502019B (https=) |
| UA (1) | UA72244C2 (https=) |
| WO (1) | WO2000057877A1 (https=) |
| YU (1) | YU68701A (https=) |
| ZA (1) | ZA200108807B (https=) |
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 |
| ATE538794T1 (de) | 1999-01-13 | 2012-01-15 | Bayer Healthcare Llc | Gamma carboxyarylsubstituierte diphenylharnstoffverbindungen als p38 kinasehemmer |
| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| DE60022333T2 (de) | 1999-04-09 | 2006-07-06 | Euro-Celtique S.A. | Natrium kanalblocker zusammensetzungen und deren verwendung |
| 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 |
| NZ520875A (en) | 2000-03-24 | 2005-04-29 | Euro Celtique S | Aryl substituted pyrazoles, triazoles and tetrazoles as sodium channel blocker |
| WO2001074779A1 (en) | 2000-03-31 | 2001-10-11 | Euro-Celtique S.A. | Aminopyridines and their use as anticonvulsants and sodium channel blockers |
| 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 |
| MXPA04000411A (es) | 2001-07-16 | 2004-03-18 | Euro Celtique Sa | Tiazolidinonas arilo sustituidas y uso de las mismas. |
| IL160523A0 (en) | 2001-09-03 | 2004-07-25 | Newron Pharm Spa | PHARMACEUTICAL COMPOSITION COMPRISING GABAPENTIN OR AN ANALOGUE THEREOF AND AN alpha-AMINOAMIDE AND ITS ANALGESIC USE |
| 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 |
| 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 |
| MXPA04007832A (es) | 2002-02-11 | 2005-09-08 | Bayer Pharmaceuticals Corp | Aril-ureas con actividad inhibitoria de angiogenesis. |
| DK1483247T3 (da) * | 2002-03-13 | 2009-08-17 | Euro Celtique Sa | Arylsubstituerede pyrimidiner og anvendelsen deraf |
| JP2006504660A (ja) * | 2002-07-31 | 2006-02-09 | ユーロ−セルティーク エス．エイ． | アリール置換ベンゾイミダゾール類およびナトリウムチャネルブロッカーとしてのそれらの使用 |
| EP1438956A1 (en) * | 2003-01-16 | 2004-07-21 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful as antimigraine agents |
| US7557129B2 (en) | 2003-02-28 | 2009-07-07 | Bayer Healthcare Llc | Cyanopyridine derivatives useful in the treatment of cancer and other disorders |
| MY142651A (en) | 2003-03-18 | 2010-12-15 | Merck Sharp & Dohme | Biaryl substituted triazoles as sodium channel blockers |
| WO2004113274A2 (en) | 2003-05-20 | 2004-12-29 | Bayer Pharmaceuticals Corporation | Diaryl ureas with kinase inhibiting activity |
| PT1558582E (pt) | 2003-07-22 | 2006-05-31 | Arena Pharm Inc | Derivados de diaril- e aril-heteroaril-ureia como moduladores do receptor de serotonina 5-ht2a uteis para a profilaxia e tratamento de desordens relacionadas com o mesmo |
| EA010485B1 (ru) | 2003-07-23 | 2008-10-30 | Байер Фамэсьютиклс Копэрейшн | Производное n,n'-дифенилмочевины, фармацевтическая композиция (варианты) и способ лечения и предупреждения заболеваний и состояний с его использованием (варианты) |
| CA2551611C (en) | 2003-12-26 | 2013-06-25 | Kyowa Kirin Co., Ltd. | Thiazole derivatives for treating or preventing parkinson's disease |
| CA2559038C (en) | 2004-03-23 | 2013-09-10 | Arena Pharmaceuticals, Inc. | Processes for preparing substituted n-aryl-n'-[3-(1h-pyrazol-5-yl) phenyl] ureas and intermediates thereof |
| US20060084695A1 (en) * | 2004-04-29 | 2006-04-20 | 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 |
| US20050282883A1 (en) * | 2004-04-29 | 2005-12-22 | John Griffin | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| US7199126B2 (en) | 2004-04-29 | 2007-04-03 | Pharmix Corporation | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| US20050272770A1 (en) * | 2004-04-29 | 2005-12-08 | John Griffin | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| US7163945B2 (en) * | 2004-04-29 | 2007-01-16 | Pharmix Corp. | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| 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 |
| WO2007022568A1 (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 |
| 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 |
| ATE472529T1 (de) | 2005-10-10 | 2010-07-15 | Glaxo Group Ltd | Prolinamidderivate als natriumkanalmodulatoren |
| CA2632030A1 (en) * | 2005-12-15 | 2007-06-21 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| EP1963280B1 (en) | 2005-12-22 | 2015-10-28 | Newron Pharmaceuticals S.p.A. | 2-phenylethylamino derivatives as calcium and/or sodium channel modulators |
| ES2536762T3 (es) | 2006-05-18 | 2015-05-28 | Arena Pharmaceuticals, Inc. | Aminas primarias y sus derivados como moduladores del receptor de la serotonina 5-HT2A útiles para el tratamiento de trastornos relacionados con este |
| 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 |
| JP5286254B2 (ja) | 2006-05-18 | 2013-09-11 | アリーナ ファーマシューティカルズ， インコーポレイテッド | ５−ｈｔ２ａセロトニンレセプター活性のモジュレーターとして有用なフェニルピラゾールの結晶形態および調製方法 |
| EP2081905B1 (en) * | 2006-07-28 | 2012-09-12 | Boehringer Ingelheim International GmbH | Sulfonyl compounds which modulate the cb2 receptor |
| EP2082005B9 (en) | 2006-09-01 | 2013-05-22 | Pleotint, L.L.C. | Ligand exchange thermochromic, (letc), systems |
| CA2664310A1 (en) * | 2006-09-25 | 2008-04-03 | 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 |
| WO2009023253A2 (en) | 2007-08-15 | 2009-02-19 | Arena Pharmaceuticals Inc. | IMIDAZO[L,2-α]PYRIDINE DERIVATIVES AS MODULATORS OF THE 5-HT2A SEROTONIN RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO |
| JP5492092B2 (ja) * | 2007-11-07 | 2014-05-14 | 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受容体を調節する化合物 |
| 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 |
| EP2326629B1 (en) * | 2008-07-10 | 2013-10-02 | Boehringer Ingelheim International GmbH | Sulfone compounds which modulate the cb2 receptor |
| WO2010036630A2 (en) | 2008-09-25 | 2010-04-01 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the cb2 receptor |
| 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 |
| CN104739829B (zh) | 2008-10-28 | 2018-11-06 | 艾尼纳制药公司 | 用于治疗5-ht2a5-羟色胺受体相关障碍的5-ht2a5-羟色胺受体调节剂组合物 |
| RU2528231C2 (ru) * | 2009-04-24 | 2014-09-10 | Тиботек Фармасьютикалз | Диариловые эфиры |
| US8299103B2 (en) | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| JP5756800B2 (ja) | 2009-06-16 | 2015-07-29 | 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受容体を調節するアゼチジン２−カルボキサミド誘導体 |
| UY32826A (es) | 2009-08-04 | 2011-02-28 | Takeda Pharmaceutical | Compuestos heterocíclicos |
| JP2013505295A (ja) * | 2009-09-22 | 2013-02-14 | 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受容体を選択的に調節する化合物 |
| 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 |
| WO2011075596A1 (en) | 2009-12-18 | 2011-06-23 | 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 |
| US9315454B2 (en) | 2010-01-15 | 2016-04-19 | 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 |
| EP2542539B1 (en) | 2010-03-05 | 2014-02-26 | Boehringer Ingelheim International GmbH | Tetrazole compounds which selectively modulate the cb2 receptor |
| JP2013531687A (ja) | 2010-07-16 | 2013-08-08 | パーデュー、ファーマ、リミテッド、パートナーシップ | ナトリウムチャネル遮断剤としてのピリジン化合物 |
| JP5746764B2 (ja) | 2010-07-22 | 2015-07-08 | 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受容体を調節する化合物 |
| EP2616441B1 (en) | 2010-09-17 | 2019-08-07 | Purdue Pharma L.P. | Pyridine compounds and the uses thereof |
| EP2625169B1 (en) | 2010-10-05 | 2015-03-25 | Purdue Pharma L.P. | Quinazoline compounds as sodium channel blockers |
| CN103429571A (zh) | 2010-12-22 | 2013-12-04 | 普渡制药公司 | 作为钠通道阻断剂的取代吡啶 |
| WO2013030665A1 (en) | 2011-09-02 | 2013-03-07 | Purdue Pharma L.P. | Pyrimidines as sodium channel blockers |
| AU2012321111A1 (en) | 2011-10-31 | 2013-05-16 | Purdue Pharma L.P. | Quaternized amines as sodium channel blockers |
| WO2013064883A1 (en) * | 2011-10-31 | 2013-05-10 | Purdue Pharma L.P. | Heteroaryl compounds as sodium channel blockers |
| US9133131B2 (en) | 2011-11-15 | 2015-09-15 | Purdue Pharma L.P. | Pyrimidine diol amides as sodium channel blockers |
| JP6170944B2 (ja) | 2011-12-28 | 2017-07-26 | ヤンセン・サイエンシズ・アイルランド・ユーシー | Ｈｃｖ阻害剤としてのヘテロ−二環式誘導体 |
| 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 |
| KR102196741B1 (ko) | 2012-04-17 | 2020-12-30 | 퍼듀 퍼머 엘피 | 오피오이드-유도 유해 약역학 반응을 치료하기 위한 시스템 및 방법 |
| WO2014096941A1 (en) | 2012-12-20 | 2014-06-26 | Purdue Pharma L.P. | Cyclic sulfonamides as sodium channel blockers |
| US9637458B2 (en) | 2013-03-04 | 2017-05-02 | Jeffrey Lockman | Pyrimidine carboxamides as sodium channel blockers |
| US9120786B2 (en) | 2013-03-04 | 2015-09-01 | Purdue Pharma, L.P. | Triazine carboxamides as sodium channel blockers |
| CA3082427A1 (en) | 2013-03-15 | 2014-09-25 | Purdue Pharma L.P. | Carboxamide derivatives and use thereof |
| EP2803668A1 (en) | 2013-05-17 | 2014-11-19 | Boehringer Ingelheim International Gmbh | Novel (cyano-dimethyl-methyl)-isoxazoles and -[1,3,4]thiadiazoles |
| WO2015031036A1 (en) | 2013-08-26 | 2015-03-05 | Purdue Pharma L.P. | Azaspiro[4.5] decane derivatives and use thereof |
| US9359330B2 (en) | 2013-08-26 | 2016-06-07 | Purdue Pharma L.P. | Substituted piperidines as sodium channel blockers |
| 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 |
| US9745287B2 (en) | 2013-12-20 | 2017-08-29 | Purdue Pharma L.P. | Pyrimidines and use thereof |
| CR20160279A (es) | 2013-12-20 | 2016-08-31 | Novartis Ag | Derivados de ácido heteroaril butanóico como inhibidores de lta4h |
| US9695144B2 (en) | 2013-12-23 | 2017-07-04 | Purdue Pharma L.P. | Dibenzazepine derivatives and use thereof |
| AU2014370407B2 (en) * | 2013-12-23 | 2018-03-29 | Purdue Pharma L.P. | Indazoles and use thereof |
| EP3089978B1 (en) | 2013-12-30 | 2018-08-29 | Purdue Pharma L.P. | Pyridone-sulfone morphinan analogs as opioid receptor ligands |
| US10047075B2 (en) | 2014-01-24 | 2018-08-14 | Purdue Pharma L.P. | Pyridines and pyrimidines and use thereof |
| US10738026B2 (en) | 2014-02-12 | 2020-08-11 | 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 |
| CA2948144A1 (en) | 2014-05-06 | 2015-11-12 | Purdue Pharma L.P. | Benzomorphan analogs and use thereof |
| EP3154972A4 (en) | 2014-06-13 | 2017-11-22 | Purdue Pharma L.P. | Azamophinan derivatives and use thereof |
| WO2015192039A1 (en) | 2014-06-13 | 2015-12-17 | Purdue Pharma L.P. | Heterocyclic morphinan 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 |
| WO2017011767A2 (en) | 2015-07-15 | 2017-01-19 | Axovant Sciences Ltd. | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of hallucinations associated with a neurodegenerative disease |
| 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 |
| KR102416971B1 (ko) | 2016-03-11 | 2022-07-04 | 엔젤 파마슈티칼 컴퍼니, 리미티드 | 브루톤형 티로신 키나제를 조절하기 위한 화합물 및 방법 |
| WO2018140504A1 (en) | 2017-01-24 | 2018-08-02 | Patel Manoj K | Compositions and methods for blocking sodium channels |
| CA3076823A1 (en) | 2017-10-05 | 2019-04-11 | Biogen Inc. | Process for preparing alpha-carboxamide pyrrolidine derivatives |
| US10707913B2 (en) * | 2018-09-04 | 2020-07-07 | Raytheon Company | Composable transceiver using low bit count inputs and outputs |
| WO2020080534A1 (ja) * | 2018-10-18 | 2020-04-23 | 住友化学株式会社 | フェニルピラゾール化合物及び植物病害防除方法 |
| WO2020086149A1 (en) * | 2018-10-26 | 2020-04-30 | University Of South Florida | Drug for treating tinnitus |
| WO2020138228A1 (ja) * | 2018-12-25 | 2020-07-02 | 学校法人東京理科大学 | ジャスモン酸内生促進剤及びジャスモン酸内生促進方法 |
| CN111825658B (zh) * | 2019-04-18 | 2024-11-08 | 华东理工大学 | 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 |
| EP0479903B1 (en) | 1989-06-30 | 1996-02-21 | E.I. Du Pont De Nemours And Company | Substituted imidazoles useful as angiotensin ii blockers |
| 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 |
| CA2135160A1 (en) | 1992-05-08 | 1993-11-25 | 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 |
| CN1169149A (zh) * | 1995-09-28 | 1997-12-31 | 株式会社大制药工场 | 止痛组合物 |
| WO1998017267A1 (en) * | 1996-10-23 | 1998-04-30 | Zymogenetics, Inc. | Compositions and methods for treating bone deficit conditions |
| 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 |
| AU7294098A (en) | 1997-05-09 | 1998-11-27 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses |
| PL337020A1 (en) | 1997-05-22 | 2000-07-31 | Searle & Co | Substituted pyrazoles as kinase p38 inhibitors |
| TW450964B (en) * | 1997-08-29 | 2001-08-21 | Takeda Schering Plough Animal | 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 |
| RU2236220C2 (ru) * | 1998-05-22 | 2004-09-20 | Аванир Фармасьютикэлз | Аналоги бензимидазола в качестве понижающих регуляторов ige |
| 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 |
| EP1127051A2 (en) * | 1998-11-06 | 2001-08-29 | Basf Aktiengesellschaft | Tricyclic pyrazole derivatives |
-
2000
- 2000-03-24 CA CA002368631A patent/CA2368631A1/en not_active Abandoned
- 2000-03-24 PT PT00919636T patent/PT1173169E/pt unknown
- 2000-03-24 US US09/533,864 patent/US6414011B1/en not_active Expired - Lifetime
- 2000-03-24 DK DK00919636.1T patent/DK1173169T3/da active
- 2000-03-24 NZ NZ514756A patent/NZ514756A/en unknown
- 2000-03-24 RU RU2001129155/04A patent/RU2001129155A/ru not_active Application Discontinuation
- 2000-03-24 ES ES00919636T patent/ES2345921T3/es not_active Expired - Lifetime
- 2000-03-24 IL IL14550800A patent/IL145508A0/xx unknown
- 2000-03-24 PL PL00351439A patent/PL351439A1/xx not_active Application Discontinuation
- 2000-03-24 YU YU68701A patent/YU68701A/sh unknown
- 2000-03-24 AU AU40291/00A patent/AU782353B2/en not_active Ceased
- 2000-03-24 KR KR1020017012292A patent/KR20020015308A/ko not_active Ceased
- 2000-03-24 WO PCT/US2000/007944 patent/WO2000057877A1/en not_active Ceased
- 2000-03-24 AT AT00919636T patent/ATE467620T1/de active
- 2000-03-24 EP EP10004963.4A patent/EP2266960B1/en not_active Expired - Lifetime
- 2000-03-24 EP EP00919636A patent/EP1173169B1/en not_active Expired - Lifetime
- 2000-03-24 TW TW089105616A patent/TW502019B/zh not_active IP Right Cessation
- 2000-03-24 JP JP2000607628A patent/JP4832647B2/ja not_active Expired - Fee Related
- 2000-03-24 DE DE60044395T patent/DE60044395D1/de not_active Expired - Lifetime
- 2000-03-24 CN CN00806810A patent/CN1353605A/zh active Pending
- 2000-03-24 AR ARP000101352A patent/AR023171A1/es unknown
- 2000-03-24 CZ CZ20013435A patent/CZ20013435A3/cs unknown
- 2000-03-24 BR BR0009322-0A patent/BR0009322A/pt not_active IP Right Cessation
- 2000-03-24 TR TR2001/02790T patent/TR200102790T2/xx unknown
- 2000-03-24 DE DE20080291U patent/DE20080291U1/de not_active Expired - Lifetime
- 2000-03-24 MX MXPA01009655A patent/MXPA01009655A/es not_active Application Discontinuation
- 2000-03-24 UA UA2001107227A patent/UA72244C2/uk unknown
- 2000-03-24 HU HU0201314A patent/HUP0201314A3/hu 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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2002540155A5 (https=) | ||
| RU2001129155A (ru) | Соединения с арильными заместителями (варианты), фармацевтическая композиция и способ лечения расстройства, чувствительного к блокаде натриевых каналов у млекопитающего, способ лечения, профилактики различных заболеваний или уменьшения интенсивности гибели или потери нейронов (варианты), способ облегчения или предупреждения эпилептических припадков у животного (варианты), соединение - радиоактивный лиганд для участка связывания в натриевом канале | |
| JP2019070032A5 (https=) | ||
| JP2003528859A5 (https=) | ||
| RU2223116C2 (ru) | Применение производных арил (или гетероарил) азолилкарбинолов в приготовлении лекарственного средства для лечения нарушений, опосредованных избытком вещества p | |
| RU2436780C2 (ru) | Производные 5-фенилтиазола и их применение в качестве ингибиторов рi3 киназы | |
| CA2565813A1 (en) | Substituted methyl aryl or heteroaryl amide compounds | |
| RU2008141509A (ru) | Mglur5 модуляторы 1 | |
| JP2019077725A5 (https=) | ||
| JP2010513272A5 (https=) | ||
| JP2007523182A5 (https=) | ||
| JP2004520292A5 (https=) | ||
| RU2439068C2 (ru) | Модуляторы mglur5 | |
| JP2002534515A5 (https=) | ||
| JP2006077019A5 (https=) | ||
| RU99104179A (ru) | Дифенильные гетероциклы в качестве модуляторов каналов калия | |
| RU2001106644A (ru) | Применение производных арил (или гетероарил) азолилкарбинолов в приготовлении лекарственного средства для лечения нарушений, опосредованных избытком вещества p | |
| CA2684105A1 (en) | Pyridine derivatives | |
| JP2014511869A5 (https=) | ||
| JP2005532982A5 (https=) | ||
| JP2008523041A5 (https=) | ||
| IL160945A (en) | 4, 5 - diarylthiazole - 2 - carboxamides having cb1 - antagonistic, agonistic or partial agonistic activity and use thereof for the preparation of pharmaceutical compositions | |
| RU2006127575A (ru) | Соединение триазола и их применение в качестве антагонистов метаботропного рецептора глутамата | |
| CA2483159A1 (en) | Triazole derivatives as tachykinin receptor antagonists | |
| JP2003525872A5 (https=) |