ZA200304188B - 1-aryl or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6-ligands. - Google Patents
1-aryl or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6-ligands. Download PDFInfo
- Publication number
- ZA200304188B ZA200304188B ZA200304188A ZA200304188A ZA200304188B ZA 200304188 B ZA200304188 B ZA 200304188B ZA 200304188 A ZA200304188 A ZA 200304188A ZA 200304188 A ZA200304188 A ZA 200304188A ZA 200304188 B ZA200304188 B ZA 200304188B
- Authority
- ZA
- South Africa
- Prior art keywords
- piperazin
- sulfonyl
- compound
- group
- indole
- Prior art date
Links
- 239000003446 ligand Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 66
- -1 [1,3]thiazol-5-yl Chemical group 0.000 claims description 55
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical class 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 11
- 108091005435 5-HT6 receptors Proteins 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 208000010877 cognitive disease Diseases 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 3
- 208000019430 Motor disease Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- CUCNBYTZXUUYHX-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-4-[4-[(3-methoxyphenyl)methyl]piperazin-1-yl]indole Chemical compound COC1=CC=CC(CN2CCN(CC2)C=2C=3C=CN(C=3C=CC=2)S(=O)(=O)C=2C(=CC=CC=2)Br)=C1 CUCNBYTZXUUYHX-UHFFFAOYSA-N 0.000 claims description 2
- CDYITUGTTZIZLC-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-4-piperazin-1-ylindole Chemical compound BrC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2C=C1 CDYITUGTTZIZLC-UHFFFAOYSA-N 0.000 claims description 2
- PIFOIFDKDHFNSH-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound BrC1=CC=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=N1 PIFOIFDKDHFNSH-UHFFFAOYSA-N 0.000 claims description 2
- GPCUWXMKJFOSBB-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)sulfonyl-4-piperazin-1-ylindole Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2C=C1 GPCUWXMKJFOSBB-UHFFFAOYSA-N 0.000 claims description 2
- RUJLNJKQORDCPR-UHFFFAOYSA-N 1-(4,5-dichlorothiophen-2-yl)sulfonyl-4-piperazin-1-ylindole Chemical compound S1C(Cl)=C(Cl)C=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2C=C1 RUJLNJKQORDCPR-UHFFFAOYSA-N 0.000 claims description 2
- JLCVIUSMVZEVFU-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-4-piperazin-1-ylindole Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2C=C1 JLCVIUSMVZEVFU-UHFFFAOYSA-N 0.000 claims description 2
- MIEPBNLCYQHGTR-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=N1 MIEPBNLCYQHGTR-UHFFFAOYSA-N 0.000 claims description 2
- ZYMLGYVVUMYHAN-UHFFFAOYSA-N 1-(5-bromothiophen-2-yl)sulfonyl-4-piperazin-1-ylindole Chemical compound S1C(Br)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2C=C1 ZYMLGYVVUMYHAN-UHFFFAOYSA-N 0.000 claims description 2
- KAWUPYJMIGXXSC-UHFFFAOYSA-N 1-(5-bromothiophen-2-yl)sulfonyl-5-piperazin-1-ylindazole Chemical compound S1C(Br)=CC=C1S(=O)(=O)N1C2=CC=C(N3CCNCC3)C=C2C=N1 KAWUPYJMIGXXSC-UHFFFAOYSA-N 0.000 claims description 2
- UEDZPMHOGNIRAB-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(4-benzylpiperazin-1-yl)indole Chemical compound C1=CC2=C(N3CCN(CC=4C=CC=CC=4)CC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 UEDZPMHOGNIRAB-UHFFFAOYSA-N 0.000 claims description 2
- KJMGWYBTTGJEPR-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[4-(pyridin-3-ylmethyl)piperazin-1-yl]indole Chemical compound C1=CC2=C(N3CCN(CC=4C=NC=CC=4)CC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 KJMGWYBTTGJEPR-UHFFFAOYSA-N 0.000 claims description 2
- XGOLFYTTXJFXRL-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[4-(pyridin-4-ylmethyl)piperazin-1-yl]indole Chemical compound C1=CC2=C(N3CCN(CC=4C=CN=CC=4)CC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 XGOLFYTTXJFXRL-UHFFFAOYSA-N 0.000 claims description 2
- GOLUNWYMDGMZDY-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[4-[(3-methoxyphenyl)methyl]piperazin-1-yl]indole Chemical compound COC1=CC=CC(CN2CCN(CC2)C=2C=3C=CN(C=3C=CC=2)S(=O)(=O)C=2C=CC=CC=2)=C1 GOLUNWYMDGMZDY-UHFFFAOYSA-N 0.000 claims description 2
- OPAMDWUUNKYGOR-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-piperazin-1-ylindole Chemical compound C1=CC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 OPAMDWUUNKYGOR-UHFFFAOYSA-N 0.000 claims description 2
- GMFCAUGUBHAFAD-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-piperazin-1-ylindazole Chemical compound N1=CC2=CC(N3CCNCC3)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 GMFCAUGUBHAFAD-UHFFFAOYSA-N 0.000 claims description 2
- BWSUCEKJIUFWEW-UHFFFAOYSA-N 1-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]-4-piperazin-1-ylindole Chemical compound S1C2=CC=C(Cl)C=C2C(C)=C1S(=O)(=O)N(C1=CC=C2)C=CC1=C2N1CCNCC1 BWSUCEKJIUFWEW-UHFFFAOYSA-N 0.000 claims description 2
- WFVQECINUUFHCF-UHFFFAOYSA-N 4-(4-benzylpiperazin-1-yl)-1-(3,4-dimethoxyphenyl)sulfonylindole Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCN(CC=4C=CC=CC=4)CC3)=C2C=C1 WFVQECINUUFHCF-UHFFFAOYSA-N 0.000 claims description 2
- JHTSMNNVWCPMHR-UHFFFAOYSA-N 6-chloro-5-(4-piperazin-1-ylindol-1-yl)sulfonylimidazo[2,1-b][1,3]thiazole Chemical compound ClC=1N=C2SC=CN2C=1S(=O)(=O)N(C1=CC=C2)C=CC1=C2N1CCNCC1 JHTSMNNVWCPMHR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 9
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- LBTMMDOVMLKYIP-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-5-piperazin-1-ylindazole Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)N1C2=CC=C(N3CCNCC3)C=C2C=N1 LBTMMDOVMLKYIP-UHFFFAOYSA-N 0.000 claims 1
- RYEKXEYHXTYXLW-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-5-piperazin-1-ylindazole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C2=CC=C(N3CCNCC3)C=C2C=N1 RYEKXEYHXTYXLW-UHFFFAOYSA-N 0.000 claims 1
- BLSZNVAXIHHJLB-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-5-piperazin-1-ylindazole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(N3CCNCC3)C=C2C=N1 BLSZNVAXIHHJLB-UHFFFAOYSA-N 0.000 claims 1
- BDQYCKCBSBUROG-UHFFFAOYSA-N 1-(5-bromothiophen-2-yl)sulfonyl-6-piperazin-1-ylindazole Chemical compound S1C(Br)=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=N1 BDQYCKCBSBUROG-UHFFFAOYSA-N 0.000 claims 1
- VCLTVEOPWDLFIE-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(4-propylpiperazin-1-yl)indazole Chemical compound C1CN(CCC)CCN1C1=CC=CC2=C1C=NN2S(=O)(=O)C1=CC=CC=C1 VCLTVEOPWDLFIE-UHFFFAOYSA-N 0.000 claims 1
- ZMXCKJRECUDHAU-UHFFFAOYSA-N 1-(benzenesulfonyl)-6-piperazin-1-ylindazole Chemical compound N1=CC2=CC=C(N3CCNCC3)C=C2N1S(=O)(=O)C1=CC=CC=C1 ZMXCKJRECUDHAU-UHFFFAOYSA-N 0.000 claims 1
- TUPSWEWNSPJDFW-UHFFFAOYSA-N 4-(4-benzylpiperazin-1-yl)-1-(2-bromophenyl)sulfonylindole Chemical compound BrC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCN(CC=4C=CC=CC=4)CC3)=C2C=C1 TUPSWEWNSPJDFW-UHFFFAOYSA-N 0.000 claims 1
- UDLMHEREVJFTSO-UHFFFAOYSA-N 4-piperazin-1-yl-1-[4-(trifluoromethoxy)phenyl]sulfonylindole Chemical compound C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2C=C1 UDLMHEREVJFTSO-UHFFFAOYSA-N 0.000 claims 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 14
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 13
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 208000015114 central nervous system disease Diseases 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 230000036506 anxiety Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- OPSJQGZSGGUEMU-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-4-[4-(pyridin-3-ylmethyl)piperazin-1-yl]indole Chemical compound BrC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCN(CC=4C=NC=CC=4)CC3)=C2C=C1 OPSJQGZSGGUEMU-UHFFFAOYSA-N 0.000 description 1
- JCCWABGUHGKCBV-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-4-[4-(pyridin-4-ylmethyl)piperazin-1-yl]indole Chemical compound BrC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCN(CC=4C=CN=CC=4)CC3)=C2C=C1 JCCWABGUHGKCBV-UHFFFAOYSA-N 0.000 description 1
- QKYKZJKFPNBMRL-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=N1 QKYKZJKFPNBMRL-UHFFFAOYSA-N 0.000 description 1
- YRMRYQWKRPQPKF-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-4-piperazin-1-ylindole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2C=C1 YRMRYQWKRPQPKF-UHFFFAOYSA-N 0.000 description 1
- LDJPCLLPMBJKNY-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[4-(3-phenylpropyl)piperazin-1-yl]indazole Chemical compound N1=CC2=C(N3CCN(CCCC=4C=CC=CC=4)CC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 LDJPCLLPMBJKNY-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- LUNUNJFSHKSXGQ-UHFFFAOYSA-N 4-Aminoindole Chemical compound NC1=CC=CC2=C1C=CN2 LUNUNJFSHKSXGQ-UHFFFAOYSA-N 0.000 description 1
- LAVZKLJDKGRZJG-UHFFFAOYSA-N 4-nitro-1h-indole Chemical compound [O-][N+](=O)C1=CC=CC2=C1C=CN2 LAVZKLJDKGRZJG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010013654 Drug abuse Diseases 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 206010033664 Panic attack Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- TXFLGZOGNOOEFZ-UHFFFAOYSA-N bis(2-chloroethyl)amine Chemical compound ClCCNCCCl TXFLGZOGNOOEFZ-UHFFFAOYSA-N 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 230000007659 motor function Effects 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229940124606 potential therapeutic agent Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24511800P | 2000-11-02 | 2000-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200304188B true ZA200304188B (en) | 2004-08-30 |
Family
ID=22925357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200304188A ZA200304188B (en) | 2000-11-02 | 2003-05-29 | 1-aryl or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6-ligands. |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US20020115670A1 (ja) |
| EP (2) | EP1343756A2 (ja) |
| JP (1) | JP4184077B2 (ja) |
| KR (1) | KR100822655B1 (ja) |
| CN (1) | CN1222511C (ja) |
| AR (1) | AR034270A1 (ja) |
| AU (2) | AU2005102A (ja) |
| BR (1) | BR0115102B1 (ja) |
| CA (1) | CA2426031C (ja) |
| EA (1) | EA006205B1 (ja) |
| HU (1) | HUP0303756A3 (ja) |
| IL (2) | IL155443A0 (ja) |
| MX (1) | MXPA03003800A (ja) |
| NO (1) | NO326610B1 (ja) |
| NZ (1) | NZ525592A (ja) |
| PL (1) | PL213134B1 (ja) |
| TW (1) | TWI282787B (ja) |
| WO (1) | WO2002036562A2 (ja) |
| ZA (1) | ZA200304188B (ja) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001296193B2 (en) | 2000-10-20 | 2006-04-27 | Biovitrum Ab | 2-, 3-, 4-, or 5-substituted-N1-(benzensulfonyl)indoles and their use in therapy |
| RU2294932C2 (ru) * | 2001-06-07 | 2007-03-10 | Ф.Хоффманн-Ля Рош Аг | Новые производные индола со сродством к рецептору 5-ht6 |
| KR20040010709A (ko) * | 2001-06-15 | 2004-01-31 | 에프. 호프만-라 로슈 아게 | 5-ｈｔ6 수용체 친화력을 갖는 4-피페라지닐인돌 유도체 |
| CN1321110C (zh) * | 2001-06-15 | 2007-06-13 | 弗·哈夫曼-拉罗切有限公司 | 具有5－ht6受体亲和力的4－哌嗪基吲哚衍生物 |
| US7504395B2 (en) * | 2001-07-20 | 2009-03-17 | Psychogenics, Inc. | Treatment for attention-deficit hyperactivity disorder |
| GB0203811D0 (en) | 2002-02-18 | 2002-04-03 | Glaxo Group Ltd | Compounds |
| BRPI0308696B8 (pt) | 2002-03-27 | 2021-05-25 | Axovant Sciences Gmbh | composto derivado de quinolina, seu processo de preparação, sua composição farmacêutica e seus usos |
| WO2003104193A1 (en) * | 2002-06-05 | 2003-12-18 | F. Hoffmann-La Roche Ag | 1-sulfonyl-4-aminoalkoxy indole derivatives as 5-ht6-receptor modulators for the treatment of cns-disorders |
| BR0314363A (pt) | 2002-09-17 | 2005-07-19 | Hoffmann La Roche | Indóis 2,4-substituìdos e seu uso como moduladores de 5-ht6 |
| AU2004213374A1 (en) * | 2003-02-14 | 2004-09-02 | Wyeth | Heterocyclyl-3-sulfonylindazoles as 5-hydroxytryptamine-6 ligands |
| WO2005012254A1 (en) | 2003-07-22 | 2005-02-10 | Arena Pharmaceuticals, Inc. | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of disorders related therto |
| SE0302760D0 (sv) * | 2003-10-20 | 2003-10-20 | Biovitrum Ab | New compounds |
| AU2004290499C1 (en) | 2003-11-03 | 2011-02-24 | Probiodrug Ag | Combinations useful for the treatment of neuronal disorders |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| CA2575359A1 (en) | 2004-07-28 | 2006-02-02 | Glaxo Group Limited | Piperazine derivatives useful for the treatment of gastrointestinal disorders |
| CA2619010C (en) * | 2005-08-15 | 2013-10-01 | Wyeth | Substituted-3-sulfonylindazole derivatives as 5-hydroxytryptamine-6 ligands |
| PE20071143A1 (es) * | 2006-01-13 | 2008-01-20 | Wyeth Corp | Composicion farmaceutica que comprende un inhibidor de acetilcolinesterasa y un antagonista 5-hidroxitriptamina-6 |
| CA2637531A1 (en) * | 2006-02-17 | 2007-08-30 | Memory Pharmaceuticals Corporation | Compounds having 5-ht6 receptor affinity |
| JP2009531385A (ja) | 2006-03-31 | 2009-09-03 | グラクソ グループ リミテッド | 成長ホルモン分泌促進物質（ｇｈｓ）受容体アゴニストとしてのピペラジン誘導体 |
| RU2008139078A (ru) * | 2006-04-05 | 2010-05-10 | Вайет (Us) | Производные сульфонил-3-гетероциклилиндазола в качестве лигандов 5-гидрокситриптамина-6 |
| WO2007120596A1 (en) * | 2006-04-12 | 2007-10-25 | Wyeth | DIHYDRO[1,4]DIOXINO[2,3-e]INDAZOLE DERIVATIVES AS 5-HYDROXYTRYPTAMINE-6 LIGANDS |
| ES2533902T3 (es) * | 2007-01-08 | 2015-04-15 | Suven Life Sciences Limited | Compuestos de 4-(heterociclil)alquil-N-(arilsulfonil)indol y su uso como ligandos del 5-HT6 |
| ATE491685T1 (de) | 2007-01-08 | 2011-01-15 | Suven Life Sciences Ltd | 5-(heterocyclyl)alkyl-n- (arylsulfonyl)indolverbindungen und ihre verwendung als 5-ht6-liganden |
| US20080200471A1 (en) * | 2007-02-16 | 2008-08-21 | Memory Pharmaceuticals Corporation | 6' substituted compounds having 5-ht6 receptor affinity |
| TW200848021A (en) | 2007-03-06 | 2008-12-16 | Wyeth Corp | Sulfonylated heterocycles useful for modulation of the progesterone receptor |
| DK2155674T3 (da) | 2007-05-03 | 2011-09-26 | Suven Life Sciences Ltd | Aminoalkoxy-aryl-sulfonamidforbindelser og anvendelse heraf som 5-HT6-ligander |
| AU2008286760A1 (en) * | 2007-08-15 | 2009-02-19 | Memory Pharmaceuticals Corporation | 3' substituted compounds having 5-HT6 receptor affinity |
| EP2508177A1 (en) * | 2007-12-12 | 2012-10-10 | Glaxo Group Limited | Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline |
| 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 |
| US20100016297A1 (en) * | 2008-06-24 | 2010-01-21 | Memory Pharmaceuticals Corporation | Alkyl-substituted 3' compounds having 5-ht6 receptor affinity |
| US20100022581A1 (en) * | 2008-07-02 | 2010-01-28 | Memory Pharmaceuticals Corporation | Pyrrolidine-substituted azaindole compounds having 5-ht6 receptor affinity |
| US20100029629A1 (en) * | 2008-07-25 | 2010-02-04 | Memory Pharmaceuticals Corporation | Acyclic compounds having 5-ht6 receptor affinity |
| US20100056531A1 (en) * | 2008-08-22 | 2010-03-04 | Memory Pharmaceuticals Corporation | Alkyl-substituted 3' compounds having 5-ht6 receptor affinity |
| MX2011002884A (es) | 2008-09-17 | 2011-04-21 | Suven Life Sciences Ltd | Compuestos de aril-sulfonamida-amina y su uso como ligandos de 5-ht6. |
| US8318725B2 (en) | 2008-09-17 | 2012-11-27 | Suven Life Sciences Limited | Aryl indolyl sulfonamide compounds and their use as 5-HT6 ligands |
| US9126946B2 (en) | 2008-10-28 | 2015-09-08 | 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 |
| UA100192C2 (en) * | 2008-11-11 | 2012-11-26 | УАЙТ ЭлЭлСи | 1-(arylsulfonyl)-4-(piperazin-1-yl)-1h-benzimidazoles as 5-hydroxytryptamine-6 ligands |
| JP2012525355A (ja) * | 2009-04-30 | 2012-10-22 | アボット ゲーエムベーハー ウント カンパニー カーゲー | セロトニン５−ｈｔ６受容体の調節に応答する障害を治療するのに適したベンゼンスルホンアニリド化合物 |
| US8940716B2 (en) | 2010-05-06 | 2015-01-27 | Bristol-Myers Squibb Company | Bicyclic heteroaryl compounds as GPR119 modulators |
| CA2799154A1 (en) | 2010-05-12 | 2011-11-17 | Abbvie Inc. | Indazole inhibitors of kinase |
| PL395469A1 (pl) * | 2011-06-29 | 2013-01-07 | Adamed Spólka Z Ograniczona Odpowiedzialnoscia | Pochodne indoloamin do leczenia chorób osrodkowego ukladu nerwowego |
| PL3030561T3 (pl) | 2013-08-07 | 2017-08-31 | Cadila Healthcare Limited | N-cyjanometyloamidy jako inhibitory kinaz janusowych |
| WO2015090233A1 (en) | 2013-12-20 | 2015-06-25 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic compounds and their application in pharmaceuticals |
| CN103880750A (zh) * | 2014-03-18 | 2014-06-25 | 上海皓元生物医药科技有限公司 | 一种替格列汀关键中间体的制备方法 |
| AU2015286049B2 (en) * | 2014-07-08 | 2018-03-01 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
| US9550754B2 (en) | 2014-09-11 | 2017-01-24 | AbbVie Deutschland GmbH & Co. KG | 4,5-dihydropyrazole derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CN111943890B (zh) * | 2014-11-03 | 2023-10-31 | 艾欧米制药有限公司 | 药用化合物 |
| MX2017016413A (es) | 2015-06-12 | 2018-08-01 | Axovant Sciences Gmbh | Derivados de diaril y arilheteroaril urea como moduladores del receptor 5ht2a de serotonina útiles para la profilaxis y el tratamineto de un trastorno conductual del sueño rem. |
| MX2018000465A (es) | 2015-07-15 | 2018-09-17 | Axovant Sciences Gmbh | Derivados de diaril y arilheteroaril urea como moduladores del receptor de serotonina 5-ht2a útiles para la profilaxis y el tratamiento de alucinaciones asociadas con una enfermedad neurodegenerativa. |
| TWI651308B (zh) * | 2016-09-23 | 2019-02-21 | 瑞士商諾華公司 | 用於肌腱及／或韌帶傷害之吲唑化合物 |
| TWI748194B (zh) | 2018-06-28 | 2021-12-01 | 德商菲尼克斯 Ｆｘｒ有限責任公司 | 含有雙環核心部分之新穎lxr調節劑 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0773942A1 (en) * | 1994-07-26 | 1997-05-21 | Pfizer Inc. | 4-indole derivatives as serotonin agonists and antagonists |
| US5849759A (en) * | 1995-12-08 | 1998-12-15 | Berlex Laboratories, Inc. | Naphthyl-substituted benzimidazole derivatives as anti-coagulants |
| GB9716656D0 (en) * | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| DE69906397T2 (de) * | 1998-01-16 | 2004-02-19 | F. Hoffmann-La Roche Ag | Benzosulfonderivate |
| US6251893B1 (en) * | 1998-06-15 | 2001-06-26 | Nps Allelix Corp. | Bicyclic piperidine and piperazine compounds having 5-HT6 receptor affinity |
| SE0002754D0 (sv) * | 2000-07-21 | 2000-07-21 | Pharmacia & Upjohn Ab | New pharmaceutical combination formulation and method of treatment with the combination |
| AU2001296193B2 (en) * | 2000-10-20 | 2006-04-27 | Biovitrum Ab | 2-, 3-, 4-, or 5-substituted-N1-(benzensulfonyl)indoles and their use in therapy |
-
2001
- 2001-10-31 CN CNB018216587A patent/CN1222511C/zh not_active Expired - Fee Related
- 2001-10-31 BR BRPI0115102-9B1A patent/BR0115102B1/pt not_active IP Right Cessation
- 2001-10-31 EA EA200300528A patent/EA006205B1/ru not_active IP Right Cessation
- 2001-10-31 HU HU0303756A patent/HUP0303756A3/hu unknown
- 2001-10-31 EP EP01992697A patent/EP1343756A2/en not_active Withdrawn
- 2001-10-31 WO PCT/US2001/045389 patent/WO2002036562A2/en active IP Right Grant
- 2001-10-31 EP EP10177536A patent/EP2298738B1/en not_active Expired - Lifetime
- 2001-10-31 IL IL15544301A patent/IL155443A0/xx unknown
- 2001-10-31 PL PL362138A patent/PL213134B1/pl unknown
- 2001-10-31 CA CA2426031A patent/CA2426031C/en not_active Expired - Fee Related
- 2001-10-31 KR KR1020037006000A patent/KR100822655B1/ko not_active IP Right Cessation
- 2001-10-31 AU AU2005102A patent/AU2005102A/xx active Pending
- 2001-10-31 MX MXPA03003800A patent/MXPA03003800A/es active IP Right Grant
- 2001-10-31 JP JP2002539322A patent/JP4184077B2/ja not_active Expired - Fee Related
- 2001-10-31 NZ NZ525592A patent/NZ525592A/en not_active IP Right Cessation
- 2001-10-31 AU AU2002220051A patent/AU2002220051B2/en not_active Ceased
- 2001-11-01 AR ARP010105112A patent/AR034270A1/es unknown
- 2001-11-01 US US10/003,015 patent/US20020115670A1/en not_active Abandoned
- 2001-11-01 TW TW1-ARYL-ORA patent/TWI282787B/zh not_active IP Right Cessation
-
2003
- 2003-04-15 IL IL155443A patent/IL155443A/en not_active IP Right Cessation
- 2003-04-30 NO NO20031977A patent/NO326610B1/no not_active IP Right Cessation
- 2003-05-29 ZA ZA200304188A patent/ZA200304188B/en unknown
- 2003-12-04 US US10/727,956 patent/US20040087595A1/en not_active Abandoned
- 2003-12-04 US US10/728,330 patent/US20040132741A1/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200304188B (en) | 1-aryl or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6-ligands. | |
| US6509357B1 (en) | 1-aryl or 1-alkylsulfonylbenzazole derivatives as 5-hydroxytryptamine-6 ligands | |
| AU2002220051A1 (en) | 1-aryl- or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands | |
| CN101595098B (zh) | 作为σ受体抑制剂的1,2,4-三唑衍生物 | |
| RU2347780C2 (ru) | Гетероциклил-3-сульфонилиндазолы в качестве лигандов 5-гидрокситриптамина-6 | |
| US20030069278A1 (en) | Heterocyclyloxy-, -thioxy- and -aminobenzazole derivatives as 5-hydroxytryptamine-6 ligands | |
| AU2002251811A1 (en) | 1-aryl-or 1-alkylsulfonylbenzazole derivatives as 5-hydroxytryptamine-6 ligands | |
| MXPA05000649A (es) | Derivados de 1-heterociclilalquil-3-sulfonilindol o indazol como ligandos de 5-hidroxitriptamina-6. | |
| US20040192749A1 (en) | 1-Aryl- or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands | |
| ZA200305625B (en) | Heterocyclyalkylindole or -azaindole compounds as 5-hydroxytryptamine-6 ligands. | |
| AU2002309585B2 (en) | Heterocyclylalkoxy-, -alkylthio- and -alkylaminobenzazole derivatives as 5-hydroxytryptamine-6 ligands | |
| US7541358B2 (en) | 1-aryl-or 1-alkylsulfonylbenzazole derivatives as 5-hydroxytryptamine-6 ligands | |
| SK17899A3 (en) | Palladium catalyzed indolization | |
| WO1996011195A1 (en) | Indole derivatives as 5ht1-like agonists | |
| Bhat et al. | Research Article Enaminone-Derived Pyrazoles with Antimicrobial Activity | |
| AU2008200380A1 (en) | Use of GAL3 receptor antagonists for the treatment of depression and/or anxiety and compounds useful in such methods |