ZA200305622B - Heterocyclindazole and azaindazole compounds as 5-hydroxytryptamine-6 ligands. - Google Patents
Heterocyclindazole and azaindazole compounds as 5-hydroxytryptamine-6 ligands. Download PDFInfo
- Publication number
- ZA200305622B ZA200305622B ZA200305622A ZA200305622A ZA200305622B ZA 200305622 B ZA200305622 B ZA 200305622B ZA 200305622 A ZA200305622 A ZA 200305622A ZA 200305622 A ZA200305622 A ZA 200305622A ZA 200305622 B ZA200305622 B ZA 200305622B
- Authority
- ZA
- South Africa
- Prior art keywords
- indole
- piperidin
- methyl
- pyrrolo
- sulfonyl
- Prior art date
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- 239000003446 ligand Substances 0.000 title description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 102
- -1 imidazo[2, 1-b]thiazolyl Chemical group 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 108091005435 5-HT6 receptors Proteins 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 125000005605 benzo group Chemical group 0.000 claims description 6
- 210000003169 central nervous system Anatomy 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- IEUPBNVDKABQRD-UHFFFAOYSA-N 1-(1-benzothiophen-4-ylsulfonyl)-5-fluoro-3-(1-methylazepan-4-yl)indole Chemical compound C1CN(C)CCCC1C1=CN(S(=O)(=O)C=2C=3C=CSC=3C=CC=2)C2=CC=C(F)C=C12 IEUPBNVDKABQRD-UHFFFAOYSA-N 0.000 claims description 2
- NJAWBWFJLFGUHK-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-3-(1-methylpyrrolidin-3-yl)indole Chemical compound C1N(C)CCC1C1=CN(S(=O)(=O)C=2C(=CC=CC=2)Br)C2=CC=CC=C12 NJAWBWFJLFGUHK-UHFFFAOYSA-N 0.000 claims description 2
- LYDOPEFYQVEQHI-UHFFFAOYSA-N 1-(2-iodophenyl)sulfonyl-3-(1-methylpyrrolidin-3-yl)indole Chemical compound C1N(C)CCC1C1=CN(S(=O)(=O)C=2C(=CC=CC=2)I)C2=CC=CC=C12 LYDOPEFYQVEQHI-UHFFFAOYSA-N 0.000 claims description 2
- SHXFFVWCEONIIE-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)sulfonyl-3-(1-methylpyrrolidin-3-yl)indole Chemical compound C1N(C)CCC1C1=CN(S(=O)(=O)C=2C=C(Cl)C(Cl)=CC=2)C2=CC=CC=C12 SHXFFVWCEONIIE-UHFFFAOYSA-N 0.000 claims description 2
- WYIXSNCSCVYJDE-UHFFFAOYSA-N 1-(3,4-difluorophenyl)sulfonyl-3-piperidin-3-ylindole Chemical compound C1=C(F)C(F)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C2CNCCC2)=C1 WYIXSNCSCVYJDE-UHFFFAOYSA-N 0.000 claims description 2
- ZKBASIGNGVQFQO-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)sulfonyl-3-(1-methylpyrrolidin-3-yl)indole Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C2CN(C)CC2)=C1 ZKBASIGNGVQFQO-UHFFFAOYSA-N 0.000 claims description 2
- BJTFNBMRVSVEDY-UHFFFAOYSA-N 1-(3-chloro-5-methoxyphenyl)sulfonyl-3-(7,7-dimethyl-1,2,3,6-tetrahydroazepin-5-yl)-5-fluoroindole Chemical compound COC1=CC(Cl)=CC(S(=O)(=O)N2C3=CC=C(F)C=C3C(C=3CC(C)(C)NCCC=3)=C2)=C1 BJTFNBMRVSVEDY-UHFFFAOYSA-N 0.000 claims description 2
- FUQPHANCZOHROJ-UHFFFAOYSA-N 1-(3-chlorophenyl)sulfonyl-3-piperidin-3-ylindole Chemical compound ClC1=CC=CC(S(=O)(=O)N2C3=CC=CC=C3C(C3CNCCC3)=C2)=C1 FUQPHANCZOHROJ-UHFFFAOYSA-N 0.000 claims description 2
- WDVPNAKGEPYYAQ-UHFFFAOYSA-N 1-(3-fluorophenyl)sulfonyl-3-(1-methylpyrrolidin-3-yl)indazole Chemical compound C1N(C)CCC1C1=NN(S(=O)(=O)C=2C=C(F)C=CC=2)C2=CC=CC=C12 WDVPNAKGEPYYAQ-UHFFFAOYSA-N 0.000 claims description 2
- DIMTVMVPJUZJIE-UHFFFAOYSA-N 1-(3-fluorophenyl)sulfonyl-3-[1-(1-phenylethyl)pyrrolidin-3-yl]indazole Chemical compound C=1C=CC=CC=1C(C)N(C1)CCC1C(C1=CC=CC=C11)=NN1S(=O)(=O)C1=CC=CC(F)=C1 DIMTVMVPJUZJIE-UHFFFAOYSA-N 0.000 claims description 2
- GYFABGMYDPKBEU-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-3-(1-methylpyrrolidin-3-yl)indole Chemical compound C1N(C)CCC1C1=CN(S(=O)(=O)C=2C=CC(Cl)=CC=2)C2=CC=CC=C12 GYFABGMYDPKBEU-UHFFFAOYSA-N 0.000 claims description 2
- OQHLZXDYWSCSEH-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-piperidin-4-ylindazole Chemical compound C1=CC(F)=CC=C1N1C2=CC=CC=C2C(C2CCNCC2)=N1 OQHLZXDYWSCSEH-UHFFFAOYSA-N 0.000 claims description 2
- LIOMFJVXCGRTDD-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-3-(1-methylpyrrolidin-3-yl)indole Chemical compound C1N(C)CCC1C1=CN(S(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=CC=C12 LIOMFJVXCGRTDD-UHFFFAOYSA-N 0.000 claims description 2
- DAUBLWHUGYHXTF-UHFFFAOYSA-N 1-(4-iodophenyl)sulfonyl-3-(1-methylpyrrolidin-3-yl)indole Chemical compound C1N(C)CCC1C1=CN(S(=O)(=O)C=2C=CC(I)=CC=2)C2=CC=CC=C12 DAUBLWHUGYHXTF-UHFFFAOYSA-N 0.000 claims description 2
- XTMPQHUYTBBBBH-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-3-piperidin-3-ylindole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C2CNCCC2)=C1 XTMPQHUYTBBBBH-UHFFFAOYSA-N 0.000 claims description 2
- HVRRXEXBELELEV-UHFFFAOYSA-N 1-(4-nitrophenyl)-3-piperidin-4-ylindazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C2=CC=CC=C2C(C2CCNCC2)=N1 HVRRXEXBELELEV-UHFFFAOYSA-N 0.000 claims description 2
- JJNCPALKVTYAFB-UHFFFAOYSA-N 1-(5-chlorothiophen-2-yl)sulfonyl-3-piperidin-3-ylindole Chemical compound S1C(Cl)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C2CNCCC2)=C1 JJNCPALKVTYAFB-UHFFFAOYSA-N 0.000 claims description 2
- QUUSSZWUXRDTJG-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-piperidin-3-ylindole Chemical compound C1=C(C2CNCCC2)C2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 QUUSSZWUXRDTJG-UHFFFAOYSA-N 0.000 claims description 2
- SNSAZLLPGXZZDK-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-fluoro-3-(1-methyl-2,3,6,7-tetrahydroazepin-4-yl)indole Chemical compound C1CN(C)CCC=C1C1=CN(S(=O)(=O)C=2C=CC=CC=2)C2=CC=C(F)C=C12 SNSAZLLPGXZZDK-UHFFFAOYSA-N 0.000 claims description 2
- MQLCYNKSELHEED-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-3-piperidin-3-ylindole Chemical compound ClC1=CC(C(F)(F)F)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C2CNCCC2)=C1 MQLCYNKSELHEED-UHFFFAOYSA-N 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 2
- XDTDNGOPBLKLPK-UHFFFAOYSA-N 3-(1-benzylpyrrolidin-3-yl)-1-(3,4-dichlorophenyl)sulfonylindole Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C2CN(CC=3C=CC=CC=3)CC2)=C1 XDTDNGOPBLKLPK-UHFFFAOYSA-N 0.000 claims description 2
- KADCFEDAPDSNRT-UHFFFAOYSA-N 3-(1-benzylpyrrolidin-3-yl)-1-(4-methylphenyl)sulfonylindole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C2CN(CC=3C=CC=CC=3)CC2)=C1 KADCFEDAPDSNRT-UHFFFAOYSA-N 0.000 claims description 2
- ZHYYDISGIDQJTN-UHFFFAOYSA-N 3-(1-benzylpyrrolidin-3-yl)-1-(5-bromothiophen-2-yl)sulfonylindole Chemical compound S1C(Br)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C2CN(CC=3C=CC=CC=3)CC2)=C1 ZHYYDISGIDQJTN-UHFFFAOYSA-N 0.000 claims description 2
- ZHKMIYUKCINEKH-UHFFFAOYSA-N 3-(1-methyl-2,3,4,7-tetrahydroazepin-5-yl)-1-naphthalen-1-ylsulfonylindole Chemical compound C1N(C)CCCC(C=2C3=CC=CC=C3N(C=2)S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=C1 ZHKMIYUKCINEKH-UHFFFAOYSA-N 0.000 claims description 2
- ZKLYWSXXCZFOCY-UHFFFAOYSA-N 3-(1-methyl-2,5-dihydropyrrol-3-yl)-1-naphthalen-2-ylsulfonylindole Chemical compound C1N(C)CC=C1C1=CN(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C2=CC=CC=C12 ZKLYWSXXCZFOCY-UHFFFAOYSA-N 0.000 claims description 2
- TVIJGTRVSVKFMA-UHFFFAOYSA-N 3-(1-methylazepan-4-yl)-1-naphthalen-1-ylsulfonylindole Chemical compound C1CN(C)CCCC1C1=CN(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)C2=CC=CC=C12 TVIJGTRVSVKFMA-UHFFFAOYSA-N 0.000 claims description 2
- QJVMWKDMKYQQDY-UHFFFAOYSA-N 3-(1-methylpyrrolidin-3-yl)-1-naphthalen-2-ylsulfonylindole Chemical compound C1N(C)CCC1C1=CN(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C2=CC=CC=C12 QJVMWKDMKYQQDY-UHFFFAOYSA-N 0.000 claims description 2
- PUHXOKADSPMWQH-UHFFFAOYSA-N 3-(azepan-4-yl)-1-naphthalen-1-ylsulfonylindole Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)N(C1=CC=CC=C11)C=C1C1CCCNCC1 PUHXOKADSPMWQH-UHFFFAOYSA-N 0.000 claims description 2
- FLKTZPKIHXDJRN-UHFFFAOYSA-N 3-(azepan-4-yl)-5-fluoro-1-naphthalen-2-ylsulfonylindole Chemical compound C12=CC(F)=CC=C2N(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C=C1C1CCCNCC1 FLKTZPKIHXDJRN-UHFFFAOYSA-N 0.000 claims description 2
- YAVABHOWMCDPSP-UHFFFAOYSA-N 3-piperidin-3-yl-1-(4-propan-2-ylphenyl)sulfonylindole Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C2CNCCC2)=C1 YAVABHOWMCDPSP-UHFFFAOYSA-N 0.000 claims description 2
- FCWSWRGQPHDBJT-UHFFFAOYSA-N 3-piperidin-3-yl-1-[4-(trifluoromethoxy)phenyl]sulfonylindole Chemical compound C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C2CNCCC2)=C1 FCWSWRGQPHDBJT-UHFFFAOYSA-N 0.000 claims description 2
- WABXECNSEHBCHO-UHFFFAOYSA-N 4-[3-(1-benzylpyrrolidin-3-yl)indol-1-yl]sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C2CN(CC=3C=CC=CC=3)CC2)=C1 WABXECNSEHBCHO-UHFFFAOYSA-N 0.000 claims description 2
- GRRHCXMSSPAKML-UHFFFAOYSA-N 4-[3-(1-methylpyrrolidin-3-yl)indol-1-yl]sulfonylaniline Chemical compound C1N(C)CCC1C1=CN(S(=O)(=O)C=2C=CC(N)=CC=2)C2=CC=CC=C12 GRRHCXMSSPAKML-UHFFFAOYSA-N 0.000 claims description 2
- KCLFQJWYCQGYBY-UHFFFAOYSA-N 8-[3-(1-methyl-2,3,6,7-tetrahydroazepin-4-yl)indol-1-yl]sulfonylquinoline Chemical compound C1CN(C)CCC=C1C1=CN(S(=O)(=O)C=2C3=NC=CC=C3C=CC=2)C2=CC=CC=C12 KCLFQJWYCQGYBY-UHFFFAOYSA-N 0.000 claims description 2
- KUFUGINVXAUAFR-UHFFFAOYSA-N 8-[3-(1-methyl-2,5-dihydropyrrol-3-yl)indol-1-yl]sulfonylquinoline Chemical compound C1N(C)CC=C1C1=CN(S(=O)(=O)C=2C3=NC=CC=C3C=CC=2)C2=CC=CC=C12 KUFUGINVXAUAFR-UHFFFAOYSA-N 0.000 claims description 2
- 208000000044 Amnesia Diseases 0.000 claims description 2
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- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 150000007514 bases Chemical class 0.000 claims description 2
- 230000002252 carbamoylating effect Effects 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 230000006984 memory degeneration Effects 0.000 claims description 2
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
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- MUIBJFFNNOPGCV-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)sulfonyl-3-(1-ethyl-2,5-dihydropyrrol-3-yl)pyrrolo[2,3-b]pyridine Chemical compound C1N(CC)CC=C1C1=CN(S(=O)(=O)C=2C(=CC=C(Cl)C=2)Cl)C2=NC=CC=C12 MUIBJFFNNOPGCV-UHFFFAOYSA-N 0.000 claims 1
- BNJUJPXNBNMDLU-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(1-methyl-2,3,4,7-tetrahydroazepin-5-yl)indole Chemical compound C1N(C)CCCC(C=2C3=CC=CC=C3N(C=2)S(=O)(=O)C=2C=CC=CC=2)=C1 BNJUJPXNBNMDLU-UHFFFAOYSA-N 0.000 claims 1
- VYQILQNEBYIKON-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(1-methyl-2,3,6,7-tetrahydroazepin-4-yl)indole Chemical compound C1CN(C)CCC=C1C1=CN(S(=O)(=O)C=2C=CC=CC=2)C2=CC=CC=C12 VYQILQNEBYIKON-UHFFFAOYSA-N 0.000 claims 1
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- 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
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- 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
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25762700P | 2000-12-22 | 2000-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200305622B true ZA200305622B (en) | 2004-10-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200305622A ZA200305622B (en) | 2000-12-22 | 2003-07-21 | Heterocyclindazole and azaindazole compounds as 5-hydroxytryptamine-6 ligands. |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US6767912B2 (no) |
| EP (1) | EP1355904B1 (no) |
| JP (1) | JP4307073B2 (no) |
| KR (1) | KR20030062442A (no) |
| CN (1) | CN1281605C (no) |
| AR (1) | AR034283A1 (no) |
| AT (1) | ATE368658T1 (no) |
| BR (1) | BR0116323A (no) |
| CA (1) | CA2432654A1 (no) |
| DE (1) | DE60129746T2 (no) |
| DK (1) | DK1355904T3 (no) |
| EA (1) | EA200300717A1 (no) |
| ES (1) | ES2290187T3 (no) |
| HU (1) | HUP0400684A2 (no) |
| IL (1) | IL156517A0 (no) |
| MX (1) | MXPA03005432A (no) |
| NO (1) | NO20032840L (no) |
| PL (1) | PL363241A1 (no) |
| WO (1) | WO2002051837A2 (no) |
| ZA (1) | ZA200305622B (no) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL156517A0 (en) * | 2000-12-22 | 2004-01-04 | Wyeth Corp | Heterocyclindazole and azaindazole compounds as 5-hydroxytryptamine-6 ligands |
| MXPA03009490A (es) * | 2001-04-20 | 2004-02-12 | Wyeth Corp | Derivados de heterociclilalcoxi-,-alquiltio-y- alquilaminobenzazol como ligando de 5-hidroxitriptamina-6. |
| MXPA03009476A (es) * | 2001-04-20 | 2004-02-12 | Wyeth Corp | Derivados de heterocicliloxi-,-tioxi-y-aminobenzazol como ligandos de 5-hidroxitriptamina-6. |
| CZ20033529A3 (cs) * | 2001-06-07 | 2004-04-14 | F. Hoffman-La Roche Ag | Nové deriváty indolu s afinitou k receptoru 5-HT6 |
| AU2003208711A1 (en) * | 2002-02-12 | 2003-09-04 | Akzo Nobel N.V. | 1-arylsulfonyl-3-substituted indole and indoline derivatives useful in the treatment of central nervous system disorders |
| ES2201899B1 (es) | 2002-04-01 | 2005-06-01 | Almirall Prodesfarma, S.A. | Derivados de la azaindolilpiperidina como agentes antihistaminicos y antialergicos. |
| US7534897B2 (en) * | 2002-05-16 | 2009-05-19 | Shionogi & Co., Ltd. | Indole arylsulfonaimide compounds exhibiting PGD 2 receptor antagonism |
| TW200401641A (en) * | 2002-07-18 | 2004-02-01 | Wyeth Corp | 1-Heterocyclylalkyl-3-sulfonylindole or-indazole derivatives as 5-hydroxytryptamine-6 ligands |
| PL378120A1 (pl) * | 2003-02-14 | 2006-03-06 | Wyeth | Heterocyklilo-3-sulfonyloindazole jako ligandy 5-hydroksytryptaminy |
| EP1608628A2 (en) * | 2003-03-17 | 2005-12-28 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| WO2005005439A1 (en) * | 2003-07-09 | 2005-01-20 | Suven Life Sciences Limited | Benzothiazino indoles |
| AU2004259736A1 (en) * | 2003-07-23 | 2005-02-03 | Wyeth | Sulfonyldihydroimid- azopyridinone compounds as 5-hydroxytryptamine-6 ligands |
| ES2222828B1 (es) | 2003-07-30 | 2006-04-16 | Laboratorios Del Dr. Esteve, S.A. | Derivados de 1-sulfonilindoles, su preparacion y su aplicacion como medicamentos. |
| US7511145B2 (en) | 2003-08-01 | 2009-03-31 | Genelabs Technologies, Inc. | Bicyclic heteroaryl derivatives |
| DE10337184A1 (de) | 2003-08-13 | 2005-03-10 | Gruenenthal Gmbh | Substituierte 3-Pyrrolidin-Indol-Derivate |
| PT1704154E (pt) * | 2004-01-02 | 2009-08-05 | Suven Life Sciences Ltd | Novos indeno[2,1a]indenos e isoindol[2,1-a]indóis |
| WO2005066157A1 (en) * | 2004-01-02 | 2005-07-21 | Suven Life Sciences | 3-(pyrolidin-3-l) indoles as 5-ht6 receptor modulators |
| EP1747202A1 (en) | 2004-02-27 | 2007-01-31 | F.Hoffmann-La Roche Ag | Indazole derivatives and pharmaceutical compositions containing them |
| BRPI0508036A (pt) | 2004-02-27 | 2007-07-17 | Hoffmann La Roche | derivados fundidos de pirazola |
| MXPA06009462A (es) | 2004-02-27 | 2007-03-15 | Hoffmann La Roche | Derivados pirazolo heteroaril fusionados. |
| US7507826B2 (en) | 2004-03-30 | 2009-03-24 | Vertex Pharmaceuticals Incorporated | Azaindoles useful as inhibitors of JAK and other protein kinases |
| AR050253A1 (es) | 2004-06-24 | 2006-10-11 | Smithkline Beecham Corp | Compuesto derivado de indazol carboxamida, composicion que lo comprende y su uso para la preparacion de un medicamento |
| US7452993B2 (en) | 2004-07-27 | 2008-11-18 | Sgx Pharmaceuticals, Inc. | Fused ring heterocycle kinase modulators |
| US7626021B2 (en) | 2004-07-27 | 2009-12-01 | Sgx Pharmaceuticals, Inc. | Fused ring heterocycle kinase modulators |
| MX2007001127A (es) | 2004-07-27 | 2007-07-11 | Sgx Pharmaceuticals Inc | Moduladores de pirrolo-piridina cinasa. |
| US7361764B2 (en) | 2004-07-27 | 2008-04-22 | Sgx Pharmaceuticals, Inc. | Pyrrolo-pyridine kinase modulators |
| TW200626142A (en) | 2004-09-21 | 2006-08-01 | Glaxo Group Ltd | Chemical compounds |
| ATE460415T1 (de) * | 2004-11-29 | 2010-03-15 | Warner Lambert Co | Therapeutische pyrazoloä3,4-büpyridine und - indazole |
| US8063071B2 (en) | 2007-10-31 | 2011-11-22 | GlaxoSmithKline, LLC | Chemical compounds |
| EP1915348A1 (en) * | 2005-08-15 | 2008-04-30 | Wyeth a Corporation of the State of Delaware | Azinyl-3-sulfonylindazole derivatives as 5-hydroxytryptamine-6 ligands |
| KR20080039994A (ko) * | 2005-08-15 | 2008-05-07 | 와이어쓰 | ５-하이드록시트립타민-６ 리간드로서의치환된-３-설포닐인다졸 |
| KR101011956B1 (ko) | 2005-08-25 | 2011-01-31 | 에프. 호프만-라 로슈 아게 | Ｐ３８ ｍαｐ 키나아제 저해제 및 이의 사용 방법 |
| US20080275058A1 (en) * | 2005-09-15 | 2008-11-06 | Korea Research Institute Of Chemical Technology | N-Substituted-1H-Quinoline-2,4-Diones, Preparation Method Thereof, And Pharmaceutical Composition Containing The Same |
| WO2007031838A1 (en) | 2005-09-16 | 2007-03-22 | Ranbaxy Laboratories Limited | Substituted pyrazolo [3,4-b] pyridines as phosphodiesterase inhibitors |
| US20080015214A1 (en) * | 2005-10-24 | 2008-01-17 | Bignan Gilles C | 3-piperidin-4-yl-indole orl-1 receptor modulators |
| GB2431927B (en) | 2005-11-04 | 2010-03-17 | Amira Pharmaceuticals Inc | 5-Lipoxygenase-activating protein (FLAP) inhibitors |
| US7977359B2 (en) | 2005-11-04 | 2011-07-12 | Amira Pharmaceuticals, Inc. | 5-lipdxygenase-activating protein (FLAP) inhibitors |
| US8399666B2 (en) | 2005-11-04 | 2013-03-19 | Panmira Pharmaceuticals, Llc | 5-lipoxygenase-activating protein (FLAP) inhibitors |
| JP2010519171A (ja) * | 2006-02-17 | 2010-06-03 | メモリー・ファーマシューティカルズ・コーポレイション | ５−ｈｔ６受容体親和性を有する化合物 |
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| WO2007120596A1 (en) * | 2006-04-12 | 2007-10-25 | Wyeth | DIHYDRO[1,4]DIOXINO[2,3-e]INDAZOLE DERIVATIVES AS 5-HYDROXYTRYPTAMINE-6 LIGANDS |
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| JP2010519226A (ja) * | 2007-02-16 | 2010-06-03 | メモリー・ファーマシューティカルズ・コーポレイション | ５−ｈｔ６受容体親和性を有する６’位置換インドール及びインダゾール誘導体 |
| CN103497185A (zh) | 2007-03-14 | 2014-01-08 | 兰贝克赛实验室有限公司 | 用作磷酸二酯酶抑制剂的吡唑并(3,4-b)吡啶衍生物 |
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| CA2695456A1 (en) * | 2007-08-15 | 2009-02-19 | Robert Dunn | 3' substituted compounds having 5-ht6 receptor affinity |
| UA102379C2 (ru) * | 2007-11-05 | 2013-07-10 | Мерк Патент Гмбх | Производные 7-азаиндола как селективные ингибиторы бета-гидроксистероида дегидрогеназы 1 типа |
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| US4670447A (en) * | 1983-08-22 | 1987-06-02 | Hoechst-Roussel Pharmaceuticals Inc. | Antipsychotic 3-(piperidinyl)- and 3-(pyrrolidinyl)-1H-indazoles |
| US5196425A (en) * | 1988-09-02 | 1993-03-23 | Janssen Pharmaceutica N.V. | Antihypertensive 3-piperidinyl-indazole derivatives |
| US5409941A (en) | 1992-02-03 | 1995-04-25 | Pfizer Inc. | 5-heteroyl indole derivatives |
| ZA951822B (en) * | 1994-12-23 | 1996-09-26 | Glaxo Group Ltd | Chemical compounds |
| WO1997049698A1 (en) * | 1996-06-21 | 1997-12-31 | Glaxo Group Limited | Piperidine acetic acid derivatives and their use in the treatment of thrombotic disorders |
| JP2001504501A (ja) * | 1996-11-26 | 2001-04-03 | アレリックス バイオファーマスーティカルス インコーポレーテッド | ５−ｈｔ▲下１ｄ▼レセプターのリガンドとしての５−シクロインドール化合物 |
| ZA98376B (en) | 1997-01-23 | 1998-07-23 | Hoffmann La Roche | Sulfamide-metalloprotease inhibitors |
| GB9805716D0 (en) * | 1998-03-17 | 1998-05-13 | Merck Sharp & Dohme | Therapeutic agents |
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| AU778682B2 (en) * | 1999-04-21 | 2004-12-16 | Nps Pharmaceuticals, Inc. | Piperidine-indole compounds having 5-HT6 affinity |
| US6191141B1 (en) | 1999-08-12 | 2001-02-20 | Nps Allelix Corp. | Azaindoles having serotonin receptor affinity |
| IL156517A0 (en) * | 2000-12-22 | 2004-01-04 | Wyeth Corp | Heterocyclindazole and azaindazole compounds as 5-hydroxytryptamine-6 ligands |
-
2001
- 2001-12-11 IL IL15651701A patent/IL156517A0/xx unknown
- 2001-12-11 CA CA002432654A patent/CA2432654A1/en not_active Abandoned
- 2001-12-11 JP JP2002552932A patent/JP4307073B2/ja not_active Expired - Fee Related
- 2001-12-11 DK DK01986147T patent/DK1355904T3/da active
- 2001-12-11 EA EA200300717A patent/EA200300717A1/ru unknown
- 2001-12-11 ES ES01986147T patent/ES2290187T3/es not_active Expired - Lifetime
- 2001-12-11 BR BR0116323-0A patent/BR0116323A/pt not_active IP Right Cessation
- 2001-12-11 HU HU0400684A patent/HUP0400684A2/hu unknown
- 2001-12-11 CN CNB018228283A patent/CN1281605C/zh not_active Expired - Fee Related
- 2001-12-11 AT AT01986147T patent/ATE368658T1/de not_active IP Right Cessation
- 2001-12-11 DE DE60129746T patent/DE60129746T2/de not_active Expired - Lifetime
- 2001-12-11 WO PCT/US2001/047935 patent/WO2002051837A2/en active IP Right Grant
- 2001-12-11 KR KR10-2003-7008394A patent/KR20030062442A/ko not_active Application Discontinuation
- 2001-12-11 MX MXPA03005432A patent/MXPA03005432A/es active IP Right Grant
- 2001-12-11 EP EP01986147A patent/EP1355904B1/en not_active Expired - Lifetime
- 2001-12-11 PL PL01363241A patent/PL363241A1/xx unknown
- 2001-12-20 US US10/028,168 patent/US6767912B2/en not_active Expired - Fee Related
- 2001-12-21 AR ARP010106001A patent/AR034283A1/es unknown
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2003
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- 2003-07-21 ZA ZA200305622A patent/ZA200305622B/en unknown
- 2003-10-23 US US10/691,937 patent/US6903112B2/en not_active Expired - Fee Related
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- 2005-01-20 US US11/039,344 patent/US20050124603A1/en not_active Abandoned
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| AR034283A1 (es) | 2004-02-18 |
| DE60129746D1 (de) | 2007-09-13 |
| WO2002051837A3 (en) | 2003-01-16 |
| US6767912B2 (en) | 2004-07-27 |
| ATE368658T1 (de) | 2007-08-15 |
| NO20032840D0 (no) | 2003-06-20 |
| EP1355904B1 (en) | 2007-08-01 |
| DE60129746T2 (de) | 2008-04-30 |
| EA200300717A1 (ru) | 2003-12-25 |
| NO20032840L (no) | 2003-08-20 |
| ES2290187T3 (es) | 2008-02-16 |
| US20020198213A1 (en) | 2002-12-26 |
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| MXPA03005432A (es) | 2003-09-10 |
| CN1281605C (zh) | 2006-10-25 |
| US20050124603A1 (en) | 2005-06-09 |
| KR20030062442A (ko) | 2003-07-25 |
| EP1355904A2 (en) | 2003-10-29 |
| JP4307073B2 (ja) | 2009-08-05 |
| WO2002051837A2 (en) | 2002-07-04 |
| BR0116323A (pt) | 2003-10-14 |
| CA2432654A1 (en) | 2002-07-04 |
| US20040092526A1 (en) | 2004-05-13 |
| CN1553910A (zh) | 2004-12-08 |
| JP2004518668A (ja) | 2004-06-24 |
| IL156517A0 (en) | 2004-01-04 |
| DK1355904T3 (da) | 2007-10-15 |
| HUP0400684A2 (hu) | 2004-07-28 |
| US6903112B2 (en) | 2005-06-07 |
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