AU2006250117A1 - Novel 8-sulfonylamino-3 aminosubstituted chroman or tetrahydronaphtalene derivatives modulating the 5HT6 receptor - Google Patents
Novel 8-sulfonylamino-3 aminosubstituted chroman or tetrahydronaphtalene derivatives modulating the 5HT6 receptor Download PDFInfo
- Publication number
- AU2006250117A1 AU2006250117A1 AU2006250117A AU2006250117A AU2006250117A1 AU 2006250117 A1 AU2006250117 A1 AU 2006250117A1 AU 2006250117 A AU2006250117 A AU 2006250117A AU 2006250117 A AU2006250117 A AU 2006250117A AU 2006250117 A1 AU2006250117 A1 AU 2006250117A1
- Authority
- AU
- Australia
- Prior art keywords
- methoxy
- dimethylamino
- dihydro
- chromen
- tetrahydronaphthalen
- 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.)
- Abandoned
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- -1 8-sulfonylamino-3 aminosubstituted chroman Chemical class 0.000 title claims description 60
- 108091005435 5-HT6 receptors Proteins 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims description 134
- 229910052739 hydrogen Inorganic materials 0.000 claims description 114
- 125000000217 alkyl group Chemical group 0.000 claims description 95
- 229940124530 sulfonamide Drugs 0.000 claims description 73
- 239000001257 hydrogen Substances 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 125000001188 haloalkyl group Chemical group 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 34
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 33
- 150000003456 sulfonamides Chemical class 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 28
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 208000010877 cognitive disease Diseases 0.000 claims description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 208000024827 Alzheimer disease Diseases 0.000 claims description 11
- 208000008589 Obesity Diseases 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 11
- 235000020824 obesity Nutrition 0.000 claims description 11
- 201000000980 schizophrenia Diseases 0.000 claims description 11
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 claims description 10
- 239000005695 Ammonium acetate Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 208000018737 Parkinson disease Diseases 0.000 claims description 10
- 229940043376 ammonium acetate Drugs 0.000 claims description 10
- 230000001404 mediated effect Effects 0.000 claims description 10
- DWBWMAAYLWUXQK-UHFFFAOYSA-N 2,3-difluorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(F)=C1F DWBWMAAYLWUXQK-UHFFFAOYSA-N 0.000 claims description 9
- AFFPZJFLSDVZBV-UHFFFAOYSA-N 2-(trifluoromethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1C(F)(F)F AFFPZJFLSDVZBV-UHFFFAOYSA-N 0.000 claims description 9
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 9
- 208000028698 Cognitive impairment Diseases 0.000 claims description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
- 239000000543 intermediate Substances 0.000 claims description 9
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- WFLBWYLZCQOPCA-UHFFFAOYSA-N 2-fluorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1F WFLBWYLZCQOPCA-UHFFFAOYSA-N 0.000 claims description 6
- GNDKYAWHEKZHPJ-UHFFFAOYSA-N 2-nitrobenzenesulfonimidic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O GNDKYAWHEKZHPJ-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 235000019257 ammonium acetate Nutrition 0.000 claims description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- MKQNYQGIPARLKO-UHFFFAOYSA-N 2-methoxybenzenesulfonamide Chemical compound COC1=CC=CC=C1S(N)(=O)=O MKQNYQGIPARLKO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- HZVNUGABGFFPJB-IBGZPJMESA-N n-[(6s)-4-methoxy-6-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalen-1-yl]naphthalene-1-sulfonamide Chemical compound N1([C@H]2CCC=3C(NS(=O)(=O)C=4C5=CC=CC=C5C=CC=4)=CC=C(C=3C2)OC)CCCC1 HZVNUGABGFFPJB-IBGZPJMESA-N 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- QIMLQYHGPSZEGS-NSHDSACASA-N (6s)-4-methoxy-6-pyrrolidin-1-yl-5,6,7,8-tetrahydronaphthalen-1-amine Chemical compound N1([C@H]2CCC=3C(N)=CC=C(C=3C2)OC)CCCC1 QIMLQYHGPSZEGS-NSHDSACASA-N 0.000 claims description 4
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 4
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 4
- UWHWOKUAYDTFKZ-SFHVURJKSA-N 2-(4-chlorophenyl)-n-[(6s)-4-methoxy-6-(methylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]benzenesulfonamide Chemical compound C([C@@H](CC1=C(OC)C=C2)NC)CC1=C2NS(=O)(=O)C1=CC=CC=C1C1=CC=C(Cl)C=C1 UWHWOKUAYDTFKZ-SFHVURJKSA-N 0.000 claims description 4
- SBXDENYROQKXBE-UHFFFAOYSA-N 2-phenylbenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 SBXDENYROQKXBE-UHFFFAOYSA-N 0.000 claims description 4
- 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 claims description 4
- 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 101150111293 cor-1 gene Proteins 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- HNQIVZYLYMDVSB-NJFSPNSNSA-N methanesulfonamide Chemical compound [14CH3]S(N)(=O)=O HNQIVZYLYMDVSB-NJFSPNSNSA-N 0.000 claims description 4
- BOWDFGZZGROJAU-LJQANCHMSA-N n-[(3r)-3-(dimethylamino)-5-methoxy-3,4-dihydro-2h-chromen-8-yl]-4-phenylbenzenesulfonamide Chemical compound C([C@H](COC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 BOWDFGZZGROJAU-LJQANCHMSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- ABOYDMHGKWRPFD-UHFFFAOYSA-N phenylmethanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1 ABOYDMHGKWRPFD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- QHENAAWCTFTYNS-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline-6-sulfonamide Chemical compound N1CCCC2=CC(S(=O)(=O)N)=CC=C21 QHENAAWCTFTYNS-UHFFFAOYSA-N 0.000 claims description 3
- UZMQSZBTFGHLAH-UHFFFAOYSA-N 1-benzothiophene-2-sulfonamide Chemical compound C1=CC=C2SC(S(=O)(=O)N)=CC2=C1 UZMQSZBTFGHLAH-UHFFFAOYSA-N 0.000 claims description 3
- CDJWMINTCGWSAW-UHFFFAOYSA-N 2,3,4-trifluorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(F)C(F)=C1F CDJWMINTCGWSAW-UHFFFAOYSA-N 0.000 claims description 3
- ALIPLMQBIORRLO-LLVKDONJSA-N 2,4,6-trichloro-n-[(3r)-3-(dimethylamino)-5-methoxy-3,4-dihydro-2h-chromen-8-yl]benzenesulfonamide Chemical compound C([C@H](COC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=C(Cl)C=C(Cl)C=C1Cl ALIPLMQBIORRLO-LLVKDONJSA-N 0.000 claims description 3
- HXYWHGSSAJAARC-GFCCVEGCSA-N 2,4-dichloro-n-[(3r)-3-(dimethylamino)-5-methoxy-3,4-dihydro-2h-chromen-8-yl]-5-methylbenzenesulfonamide Chemical compound C([C@H](COC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=CC(C)=C(Cl)C=C1Cl HXYWHGSSAJAARC-GFCCVEGCSA-N 0.000 claims description 3
- JXLSEASONLYGSC-GFCCVEGCSA-N 2-chloro-n-[(3r)-3-(dimethylamino)-5-methoxy-3,4-dihydro-2h-chromen-8-yl]benzenesulfonamide Chemical compound C([C@H](COC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=CC=CC=C1Cl JXLSEASONLYGSC-GFCCVEGCSA-N 0.000 claims description 3
- NMBWXBWFDHVLGS-UHFFFAOYSA-N 2-ethylbenzenesulfonamide Chemical compound CCC1=CC=CC=C1S(N)(=O)=O NMBWXBWFDHVLGS-UHFFFAOYSA-N 0.000 claims description 3
- MUMNFEPQABVDQS-UHFFFAOYSA-N 2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(N)(=O)=O MUMNFEPQABVDQS-UHFFFAOYSA-N 0.000 claims description 3
- SDNPBDRTPLMQBU-CYBMUJFWSA-N 3-chloro-n-[(3r)-3-(dimethylamino)-5-methoxy-3,4-dihydro-2h-chromen-8-yl]-2-methylbenzenesulfonamide Chemical compound C([C@H](COC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=CC=CC(Cl)=C1C SDNPBDRTPLMQBU-CYBMUJFWSA-N 0.000 claims description 3
- HKVSAKBPLRSUMS-LBPRGKRZSA-N 3-chloro-n-[(6s)-6-(dimethylamino)-4-methoxy-5,6,7,8-tetrahydronaphthalen-1-yl]-4-fluorobenzenesulfonamide Chemical compound C([C@H](CCC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=CC=C(F)C(Cl)=C1 HKVSAKBPLRSUMS-LBPRGKRZSA-N 0.000 claims description 3
- MGMPFLDTPKLFRL-SECBINFHSA-N 4-bromo-5-chloro-n-[(3r)-3-(dimethylamino)-5-methoxy-3,4-dihydro-2h-chromen-8-yl]thiophene-2-sulfonamide Chemical compound C([C@H](COC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=CC(Br)=C(Cl)S1 MGMPFLDTPKLFRL-SECBINFHSA-N 0.000 claims description 3
- VFWUAUDAXWVEIE-CQSZACIVSA-N 4-bromo-n-[(3r)-3-(dimethylamino)-5-methoxy-3,4-dihydro-2h-chromen-8-yl]-2-methylbenzenesulfonamide Chemical compound C([C@H](COC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=CC=C(Br)C=C1C VFWUAUDAXWVEIE-CQSZACIVSA-N 0.000 claims description 3
- CCPNDDYDSZONDW-CYBMUJFWSA-N 4-bromo-n-[(3r)-3-(dimethylamino)-5-methoxy-3,4-dihydro-2h-chromen-8-yl]benzenesulfonamide Chemical compound C([C@H](COC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=CC=C(Br)C=C1 CCPNDDYDSZONDW-CYBMUJFWSA-N 0.000 claims description 3
- GEMCOQWSLXNTPV-LBPRGKRZSA-N 4-chloro-n-[(6s)-6-(dimethylamino)-4-methoxy-5,6,7,8-tetrahydronaphthalen-1-yl]-3-nitrobenzenesulfonamide Chemical compound C([C@H](CCC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 GEMCOQWSLXNTPV-LBPRGKRZSA-N 0.000 claims description 3
- PRXZOHWSYORCIR-KRWDZBQOSA-N 4-tert-butyl-n-[(6s)-6-(dimethylamino)-4-methoxy-5,6,7,8-tetrahydronaphthalen-1-yl]benzenesulfonamide Chemical compound C([C@H](CCC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 PRXZOHWSYORCIR-KRWDZBQOSA-N 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- AWRCZFSIXWAOIE-ZETCQYMHSA-N n-[(2s)-5-amino-8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]-2,2,2-trifluoroacetamide Chemical compound C1C[C@H](NC(=O)C(F)(F)F)CC2=C1C(N)=CC=C2OC AWRCZFSIXWAOIE-ZETCQYMHSA-N 0.000 claims description 3
- QCRSQINBLTXVPR-OAHLLOKOSA-N n-[(3r)-3-(dimethylamino)-5-methoxy-3,4-dihydro-2h-chromen-8-yl]-1-(3-nitrophenyl)methanesulfonamide Chemical compound C([C@H](COC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)CC1=CC=CC([N+]([O-])=O)=C1 QCRSQINBLTXVPR-OAHLLOKOSA-N 0.000 claims description 3
- UWUFPDXBNAQUJU-LLVKDONJSA-N n-[(3r)-3-(dimethylamino)-5-methoxy-3,4-dihydro-2h-chromen-8-yl]-2,4,6-trifluorobenzenesulfonamide Chemical compound C([C@H](COC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=C(F)C=C(F)C=C1F UWUFPDXBNAQUJU-LLVKDONJSA-N 0.000 claims description 3
- SXPFGNILDIHLEN-LLVKDONJSA-N n-[(3r)-3-(dimethylamino)-5-methoxy-3,4-dihydro-2h-chromen-8-yl]-3,4-difluorobenzenesulfonamide Chemical compound C([C@H](COC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=CC=C(F)C(F)=C1 SXPFGNILDIHLEN-LLVKDONJSA-N 0.000 claims description 3
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- MQWQOQZTWROHJW-QGZVFWFLSA-N n-[(3r)-3-(dimethylamino)-5-methoxy-3,4-dihydro-2h-chromen-8-yl]-4-phenoxybenzenesulfonamide Chemical compound C([C@H](COC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 MQWQOQZTWROHJW-QGZVFWFLSA-N 0.000 claims description 3
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- IJTYSLYIVHBKTB-HNNXBMFYSA-N n-[(6s)-6-(dimethylamino)-4-methoxy-5,6,7,8-tetrahydronaphthalen-1-yl]-1-(3-nitrophenyl)methanesulfonamide Chemical compound C([C@H](CCC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)CC1=CC=CC([N+]([O-])=O)=C1 IJTYSLYIVHBKTB-HNNXBMFYSA-N 0.000 claims description 3
- WYZUHEXIXKHCEJ-HNNXBMFYSA-N n-[(6s)-6-(dimethylamino)-4-methoxy-5,6,7,8-tetrahydronaphthalen-1-yl]-1-benzofuran-2-sulfonamide Chemical compound C1C[C@H](N(C)C)CC2=C1C(NS(=O)(=O)C=1OC3=CC=CC=C3C=1)=CC=C2OC WYZUHEXIXKHCEJ-HNNXBMFYSA-N 0.000 claims description 3
- QEGCXFVWLWKXIH-LBPRGKRZSA-N n-[(6s)-6-(dimethylamino)-4-methoxy-5,6,7,8-tetrahydronaphthalen-1-yl]-2,4,6-trifluorobenzenesulfonamide Chemical compound C([C@H](CCC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=C(F)C=C(F)C=C1F QEGCXFVWLWKXIH-LBPRGKRZSA-N 0.000 claims description 3
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- ASMPOQAFIUHWNS-CQSZACIVSA-N n-[(3r)-3-(dimethylamino)-5-methoxy-3,4-dihydro-2h-chromen-8-yl]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound O1C[C@H](N(C)C)CC2=C1C(NS(=O)(=O)C=1C=C3CCC(=O)NC3=CC=1)=CC=C2OC ASMPOQAFIUHWNS-CQSZACIVSA-N 0.000 claims 1
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- BDBHRIWMEFTKOQ-ZDUSSCGKSA-N n-[(6s)-6-(dimethylamino)-4-methoxy-5,6,7,8-tetrahydronaphthalen-1-yl]-2-(trifluoromethyl)benzenesulfonamide Chemical compound C([C@H](CCC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=CC=CC=C1C(F)(F)F BDBHRIWMEFTKOQ-ZDUSSCGKSA-N 0.000 claims 1
- WBJRNRAGAWZOMR-ZDUSSCGKSA-N n-[(6s)-6-(dimethylamino)-4-methoxy-5,6,7,8-tetrahydronaphthalen-1-yl]-2-fluoro-5-(trifluoromethyl)benzenesulfonamide Chemical compound C([C@H](CCC=12)N(C)C)C=1C(OC)=CC=C2NS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1F WBJRNRAGAWZOMR-ZDUSSCGKSA-N 0.000 claims 1
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Classifications
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- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
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- C07C311/44—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
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- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
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- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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- 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
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- C07D417/14—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 three or more hetero rings
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- Pharmacology & Pharmacy (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| PCT/SE2006/000593 WO2006126939A1 (en) | 2005-05-23 | 2006-05-22 | Novel 8-sulfonylamino-3 aminosubstituted chroman or tetrahydronaphtalene derivatives modulating the 5ht6 receptor |
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| US7754148B2 (en) | 2006-12-27 | 2010-07-13 | Progentech Limited | Instrument for cassette for sample preparation |
| US8299267B2 (en) | 2007-09-24 | 2012-10-30 | Comentis, Inc. | (3-hydroxy-4-amino-butan-2-yl) -3- (2-thiazol-2-yl-pyrrolidine-1-carbonyl) benzamide derivatives and related compounds as beta-secretase inhibitors for treating |
| AU2008331920A1 (en) | 2007-12-04 | 2009-06-11 | Merck Sharp & Dohme Corp. | Tryptamine sulfonamides as 5-HT6 antagonists |
| EP2116546A1 (en) | 2008-05-09 | 2009-11-11 | Laboratorios Del. Dr. Esteve, S.A. | Substituted N-phenyl-2,3-dihydroimidazo[2,1-b]thiazole-5-sulfonamide derivatives as 5-HT6 ligands |
| EP2116547A1 (en) | 2008-05-09 | 2009-11-11 | Laboratorios Del. Dr. Esteve, S.A. | Substituted N-imidazo(2, 1-b) thiazole-5-sulfonamide derivatives as 5-TH6 ligands |
| WO2011106384A1 (en) | 2010-02-23 | 2011-09-01 | Genturadx, Inc. | Apparatus and methods for integrated sample preparation, reaction and detection |
| US9248422B2 (en) | 2010-02-23 | 2016-02-02 | Luminex Corporation | Apparatus and methods for integrated sample preparation, reaction and detection |
| US20130109672A1 (en) | 2010-04-29 | 2013-05-02 | The United States Of America,As Represented By The Secretary, Department Of Health And Human Service | Activators of human pyruvate kinase |
| JP5641436B2 (ja) * | 2011-03-28 | 2014-12-17 | 国立大学法人 鹿児島大学 | 抗hiv薬 |
| US9840482B2 (en) | 2014-04-19 | 2017-12-12 | Sunshine Lake Pharma Co., Ltd. | Sulfonamide derivatives and pharmaceutical applications thereof |
| CA2957566C (en) | 2014-08-12 | 2023-08-01 | Daniel Paul Becker | Indoline sulfonamide inhibitors of dape and ndm-1 and use of the same |
| HUE067314T2 (hu) | 2017-09-22 | 2024-10-28 | Jubilant Epipad LLC | Heterociklusos vegyületek mint PAD gátlók |
| KR102782563B1 (ko) | 2017-10-18 | 2025-03-14 | 주빌런트 에피파드 엘엘씨 | Pad 억제제로서의 이미다조-피리딘 화합물 |
| KR20200085836A (ko) | 2017-11-06 | 2020-07-15 | 주빌런트 프로델 엘엘씨 | Pd1/pd-l1 활성화 억제제로서의 피리미딘 유도체 |
| BR112020010322A2 (pt) | 2017-11-24 | 2020-11-17 | Jubilant Episcribe Llc | composto da fórmula i; composto da fórmula ia; composto da fórmula ib; processo de preparação de compostos da fórmula i; composição farmacêutica; método para o tratamento e/ou prevenção de várias doenças; uso dos compostos; método para o tratamento de câncer; e método para o tratamento e/ou prevenção de uma afecção mediada por prmt5 ou um distúrbio proliferativo ou câncer |
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| DE2752659A1 (de) * | 1976-12-07 | 1978-06-08 | Sandoz Ag | Neue tetralinderivate, ihre herstellung und verwendung |
| CH637363A5 (en) * | 1977-11-24 | 1983-07-29 | Sandoz Ag | Process for preparing novel 2-aminotetralins |
| PL338016A1 (en) * | 1997-07-11 | 2000-09-25 | Smithkline Beecham Plc | Novel chemical compounds |
| JP2005505586A (ja) * | 2001-10-04 | 2005-02-24 | ワイス | 5−ヒドロキシトリプタミン−6リガンドとしてのクロマン誘導体 |
| NZ589649A (en) * | 2004-10-14 | 2012-04-27 | Abbott Gmbh & Co Kg | Arylsulfonylmethyl or arylsulfonamide substituted aromatic compounds suitable for treating disorders that respond to modulation of the dopamine d3 receptor |
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| AR054363A1 (es) | 2007-06-20 |
| IL187099A0 (en) | 2008-02-09 |
| EP1888517A1 (en) | 2008-02-20 |
| NO20076638L (no) | 2007-12-21 |
| KR20080016810A (ko) | 2008-02-22 |
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| WO2006126939A8 (en) | 2007-06-07 |
| CA2609747A1 (en) | 2006-11-30 |
| US20090030038A1 (en) | 2009-01-29 |
| TW200716529A (en) | 2007-05-01 |
| WO2006126939A1 (en) | 2006-11-30 |
| JP2008545686A (ja) | 2008-12-18 |
| BRPI0610119A2 (pt) | 2012-09-18 |
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