ZA200403817B - Nicotin-or isonicotin benzothiazole derivatives. - Google Patents
Nicotin-or isonicotin benzothiazole derivatives. Download PDFInfo
- Publication number
- ZA200403817B ZA200403817B ZA200403817A ZA200403817A ZA200403817B ZA 200403817 B ZA200403817 B ZA 200403817B ZA 200403817 A ZA200403817 A ZA 200403817A ZA 200403817 A ZA200403817 A ZA 200403817A ZA 200403817 B ZA200403817 B ZA 200403817B
- Authority
- ZA
- South Africa
- Prior art keywords
- methoxy
- morpholin
- benzothiazol
- isonicotinamide
- lower alkyl
- Prior art date
Links
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 99
- 150000001875 compounds Chemical class 0.000 claims description 96
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 52
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 26
- 229960005305 adenosine Drugs 0.000 claims description 26
- 102000005962 receptors Human genes 0.000 claims description 20
- 108020003175 receptors Proteins 0.000 claims description 20
- 125000002757 morpholinyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- -1 2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 102000009346 Adenosine receptors Human genes 0.000 claims description 10
- 108050000203 Adenosine receptors Proteins 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- RSHMVQKIEWQRTJ-UHFFFAOYSA-N 2-(ethylsulfanylmethyl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(CSCC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 RSHMVQKIEWQRTJ-UHFFFAOYSA-N 0.000 claims description 3
- KSLAGBYXABBALP-UHFFFAOYSA-N 2-[[2-ethoxyethyl(methyl)amino]methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(CN(C)CCOCC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 KSLAGBYXABBALP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- XCHHOJRIRJXGQD-UHFFFAOYSA-N 2-(2-acetamidoethoxy)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(OCCNC(C)=O)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 XCHHOJRIRJXGQD-UHFFFAOYSA-N 0.000 claims description 2
- RJLSZHMXFSHJJT-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(OCCOC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 RJLSZHMXFSHJJT-UHFFFAOYSA-N 0.000 claims description 2
- WGMKRKOGHXJXCO-UHFFFAOYSA-N 2-(2-methoxyethylamino)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(NCCOC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 WGMKRKOGHXJXCO-UHFFFAOYSA-N 0.000 claims description 2
- PCBJQMVIOAKHJF-UHFFFAOYSA-N 2-(cyclobutylamino)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(NC4CCC4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 PCBJQMVIOAKHJF-UHFFFAOYSA-N 0.000 claims description 2
- DNUVZCKBCOGORZ-UHFFFAOYSA-N 2-(cyclohexylamino)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(NC4CCCCC4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 DNUVZCKBCOGORZ-UHFFFAOYSA-N 0.000 claims description 2
- JAAPTLQUSORIAN-UHFFFAOYSA-N 2-(cyclopentylamino)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(NC4CCCC4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 JAAPTLQUSORIAN-UHFFFAOYSA-N 0.000 claims description 2
- VEILEBRJPHQWOB-UHFFFAOYSA-N 2-[(2-ethoxyethylamino)methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(CNCCOCC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 VEILEBRJPHQWOB-UHFFFAOYSA-N 0.000 claims description 2
- WDVFFFLRXJFWGH-UHFFFAOYSA-N 2-[(2-methoxyethylamino)methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(CNCCOC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 WDVFFFLRXJFWGH-UHFFFAOYSA-N 0.000 claims description 2
- BWLQSVMVFXBEHO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(OCCN(C)C)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 BWLQSVMVFXBEHO-UHFFFAOYSA-N 0.000 claims description 2
- HBPHIDSVWBVRQS-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl-methylamino]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(N=CC=3)N(C)CCN(C)C)=NC=2C(OC)=CC=C1N1CCOCC1 HBPHIDSVWBVRQS-UHFFFAOYSA-N 0.000 claims description 2
- AQHFPFUOJNCPFA-UHFFFAOYSA-N 2-[2-(dimethylamino)ethylamino]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(NCCN(C)C)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 AQHFPFUOJNCPFA-UHFFFAOYSA-N 0.000 claims description 2
- RDVZMZZMSRYHLO-UHFFFAOYSA-N 2-[ethyl(2-methoxyethyl)amino]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(N(CCOC)CC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 RDVZMZZMSRYHLO-UHFFFAOYSA-N 0.000 claims description 2
- DXPSECUWSVOHTB-UHFFFAOYSA-N 2-[ethyl(2-pyridin-2-ylethyl)amino]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C=1C(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=CC=NC=1N(CC)CCC1=CC=CC=N1 DXPSECUWSVOHTB-UHFFFAOYSA-N 0.000 claims description 2
- WCRPCPFIVAGQPW-UHFFFAOYSA-N 2-cyclohexyloxy-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(OC4CCCCC4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 WCRPCPFIVAGQPW-UHFFFAOYSA-N 0.000 claims description 2
- RXQWZQXEBKNYOD-UHFFFAOYSA-N 2-cyclopentyloxy-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(OC4CCCC4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 RXQWZQXEBKNYOD-UHFFFAOYSA-N 0.000 claims description 2
- AFQQDYZOHHNITG-UHFFFAOYSA-N 2-ethoxy-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(OCC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 AFQQDYZOHHNITG-UHFFFAOYSA-N 0.000 claims description 2
- XBPHTDCSBQTQBS-UHFFFAOYSA-N 2-methoxy-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(OC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 XBPHTDCSBQTQBS-UHFFFAOYSA-N 0.000 claims description 2
- YBANBTKLQXVHPG-UHFFFAOYSA-N N-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-3-(2-phenylethylamino)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C(=CN=CC=3)NCCC=3C=CC=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 YBANBTKLQXVHPG-UHFFFAOYSA-N 0.000 claims description 2
- FPCGEIHJHHPPJH-UHFFFAOYSA-N methyl n-[[4-[(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)carbamoyl]pyridin-2-yl]methyl]-n-methylcarbamate Chemical compound C1=NC(CN(C)C(=O)OC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 FPCGEIHJHHPPJH-UHFFFAOYSA-N 0.000 claims description 2
- CWOGTLLZZKUORR-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(2-morpholin-4-ylethoxy)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(OCCN4CCOCC4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 CWOGTLLZZKUORR-UHFFFAOYSA-N 0.000 claims description 2
- HHNQGFSESIBKSM-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(2-morpholin-4-ylethylamino)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(NCCN4CCOCC4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 HHNQGFSESIBKSM-UHFFFAOYSA-N 0.000 claims description 2
- GIOJFUUVQQOXJP-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(2-piperidin-1-ylethylamino)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(NCCN4CCCCC4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 GIOJFUUVQQOXJP-UHFFFAOYSA-N 0.000 claims description 2
- DOMKQCYRLNJGDM-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(methylaminomethyl)pyridine-4-carboxamide Chemical compound C1=NC(CNC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 DOMKQCYRLNJGDM-UHFFFAOYSA-N 0.000 claims description 2
- YDPCICJNBIOKRF-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(propylamino)pyridine-4-carboxamide Chemical compound C1=NC(NCCC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 YDPCICJNBIOKRF-UHFFFAOYSA-N 0.000 claims description 2
- GQZKXXKRDZFSIY-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(pyridin-2-ylmethoxy)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(OCC=4N=CC=CC=4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 GQZKXXKRDZFSIY-UHFFFAOYSA-N 0.000 claims description 2
- AWIRDUMBYCIRNQ-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-[methyl(2-pyridin-2-ylethyl)amino]pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(N=CC=3)N(C)CCC=3N=CC=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 AWIRDUMBYCIRNQ-UHFFFAOYSA-N 0.000 claims description 2
- FRWXVNWAQDZHOT-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-phenylmethoxypyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(OCC=4C=CC=CC=4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 FRWXVNWAQDZHOT-UHFFFAOYSA-N 0.000 claims description 2
- QAEONFWSFXHNLR-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-propan-2-yloxypyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(OC(C)C)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 QAEONFWSFXHNLR-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 10
- 239000000126 substance Substances 0.000 claims 8
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- RSWGKTQCDDRCPI-UHFFFAOYSA-N 2-[(4-hydroxypiperidin-1-yl)methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(CN4CCC(O)CC4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 RSWGKTQCDDRCPI-UHFFFAOYSA-N 0.000 claims 2
- 241000282326 Felis catus Species 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 claims 1
- UNRUFUOEDVHIQW-UHFFFAOYSA-N 2-(2-acetamidoethylamino)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(NCCNC(C)=O)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 UNRUFUOEDVHIQW-UHFFFAOYSA-N 0.000 claims 1
- ABOMJTOUZZKPAX-UHFFFAOYSA-N 2-(3-hydroxypiperidin-1-yl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(N=CC=3)N3CC(O)CCC3)=NC=2C(OC)=CC=C1N1CCOCC1 ABOMJTOUZZKPAX-UHFFFAOYSA-N 0.000 claims 1
- KZGJMKPUSWSYIP-UHFFFAOYSA-N 2-(3-methoxyazetidin-1-yl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1C(OC)CN1C1=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=CC=N1 KZGJMKPUSWSYIP-UHFFFAOYSA-N 0.000 claims 1
- QSDLUKISELUXNA-UHFFFAOYSA-N 2-(4-ethyl-3-oxopiperazin-1-yl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1C(=O)N(CC)CCN1C1=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=CC=N1 QSDLUKISELUXNA-UHFFFAOYSA-N 0.000 claims 1
- BYMVNFILGCFAPF-UHFFFAOYSA-N 2-(methoxymethyl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(COC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 BYMVNFILGCFAPF-UHFFFAOYSA-N 0.000 claims 1
- ZPOWOMKKQRPAQN-IYBDPMFKSA-N 2-[(2r,6s)-2,6-dimethylmorpholin-4-yl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(N=CC=3)N3C[C@@H](C)O[C@@H](C)C3)=NC=2C(OC)=CC=C1N1CCOCC1 ZPOWOMKKQRPAQN-IYBDPMFKSA-N 0.000 claims 1
- VIQMYJLHYZEWPD-UHFFFAOYSA-N 2-[[butyl(methyl)amino]methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(CN(C)CCCC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 VIQMYJLHYZEWPD-UHFFFAOYSA-N 0.000 claims 1
- XJRYXDHXOKDVIH-UHFFFAOYSA-N 2-[cyclohexyl(methyl)amino]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(N=CC=3)N(C)C3CCCCC3)=NC=2C(OC)=CC=C1N1CCOCC1 XJRYXDHXOKDVIH-UHFFFAOYSA-N 0.000 claims 1
- BASIFJVIYXHTLP-UHFFFAOYSA-N 2-cyclohexyl-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(N=CC=3)C3CCCCC3)=NC=2C(OC)=CC=C1N1CCOCC1 BASIFJVIYXHTLP-UHFFFAOYSA-N 0.000 claims 1
- GWSRFTFDSCYSPL-UHFFFAOYSA-N 2-methoxy-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(OC)=CC(C(=O)NC=2SC3=C(C=4C=CC=CC=4)C=CC(OC)=C3N=2)=C1 GWSRFTFDSCYSPL-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- SPPDEDIFTZMQRN-UHFFFAOYSA-N 6-cyclohexyloxy-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-3-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=NC(OC4CCCCC4)=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 SPPDEDIFTZMQRN-UHFFFAOYSA-N 0.000 claims 1
- OOHKOTZCGMODAC-UHFFFAOYSA-N 6-methoxy-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 OOHKOTZCGMODAC-UHFFFAOYSA-N 0.000 claims 1
- 101100167365 Caenorhabditis elegans cha-1 gene Proteins 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- XIUFMLWNZWKJEE-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(2-pyridin-2-ylethylamino)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(NCCC=4N=CC=CC=4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 XIUFMLWNZWKJEE-UHFFFAOYSA-N 0.000 claims 1
- UVAAKZKOJHRNBI-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(3-methoxypiperidin-1-yl)pyridine-4-carboxamide Chemical compound C1C(OC)CCCN1C1=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=CC=N1 UVAAKZKOJHRNBI-UHFFFAOYSA-N 0.000 claims 1
- XIGWZKHKRHZZMP-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(4-methyl-3-oxopiperazin-1-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(N=CC=3)N3CC(=O)N(C)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 XIGWZKHKRHZZMP-UHFFFAOYSA-N 0.000 claims 1
- TULISNGCEHQTBD-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(morpholin-4-ylmethyl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(CN4CCOCC4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 TULISNGCEHQTBD-UHFFFAOYSA-N 0.000 claims 1
- RJPFSUZQERSIOL-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(oxan-4-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(N=CC=3)C3CCOCC3)=NC=2C(OC)=CC=C1N1CCOCC1 RJPFSUZQERSIOL-UHFFFAOYSA-N 0.000 claims 1
- CEBCFCSGECFPDC-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(piperidin-1-ylmethyl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(CN4CCCCC4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 CEBCFCSGECFPDC-UHFFFAOYSA-N 0.000 claims 1
- ZIHXHCPIFNQNMP-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(pyrrolidin-1-ylmethyl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(CN4CCCC4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 ZIHXHCPIFNQNMP-UHFFFAOYSA-N 0.000 claims 1
- SDFGXHOEHMTZKU-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-[(2-oxopyrrolidin-1-yl)methyl]pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(CN4C(CCC4)=O)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 SDFGXHOEHMTZKU-UHFFFAOYSA-N 0.000 claims 1
- QVXLDOWTNPFYPD-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-[(4-methoxypiperidin-1-yl)methyl]pyridine-4-carboxamide Chemical compound C1CC(OC)CCN1CC1=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=CC=N1 QVXLDOWTNPFYPD-UHFFFAOYSA-N 0.000 claims 1
- DMFSNBYIICHCJL-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-[methyl(2-phenylethyl)amino]pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(N=CC=3)N(C)CCC=3C=CC=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 DMFSNBYIICHCJL-UHFFFAOYSA-N 0.000 claims 1
- HAZDEBUOKRACDQ-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-[methyl(2-piperidin-1-ylethyl)amino]pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(N=CC=3)N(C)CCN3CCCCC3)=NC=2C(OC)=CC=C1N1CCOCC1 HAZDEBUOKRACDQ-UHFFFAOYSA-N 0.000 claims 1
- FJGAQBSCABWDCP-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-[methyl(propyl)amino]pyridine-4-carboxamide Chemical compound C1=NC(N(C)CCC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 FJGAQBSCABWDCP-UHFFFAOYSA-N 0.000 claims 1
- NDOINIKFTYEWQC-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-methylsulfanylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(SC)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 NDOINIKFTYEWQC-UHFFFAOYSA-N 0.000 claims 1
- QAFOZXJMYWTQAE-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-6-propan-2-yloxypyridine-3-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=NC(OC(C)C)=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 QAFOZXJMYWTQAE-UHFFFAOYSA-N 0.000 claims 1
- OGHSVUCZNCYALL-UHFFFAOYSA-N n-(4-methoxy-7-piperidin-1-yl-1,3-benzothiazol-2-yl)-2-(4-methylpiperazin-1-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(N=CC=3)N3CCN(C)CC3)=NC=2C(OC)=CC=C1N1CCCCC1 OGHSVUCZNCYALL-UHFFFAOYSA-N 0.000 claims 1
- ZUURGJSDUUDMRB-UHFFFAOYSA-N n-(4-methoxy-7-piperidin-1-yl-1,3-benzothiazol-2-yl)-3-methyl-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C(=C(N4CCOCC4)N=CC=3)C)=NC=2C(OC)=CC=C1N1CCCCC1 ZUURGJSDUUDMRB-UHFFFAOYSA-N 0.000 claims 1
- FRKMNMOPNVOBRO-UHFFFAOYSA-N n-(4-methoxy-7-piperidin-1-yl-1,3-benzothiazol-2-yl)-3-methyl-2-pyrrolidin-1-ylpyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C(=C(N4CCCC4)N=CC=3)C)=NC=2C(OC)=CC=C1N1CCCCC1 FRKMNMOPNVOBRO-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 6
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 5
- 206010021143 Hypoxia Diseases 0.000 description 5
- 230000007954 hypoxia Effects 0.000 description 5
- 208000011117 substance-related disease Diseases 0.000 description 5
- 208000024827 Alzheimer disease Diseases 0.000 description 4
- 102000030621 adenylate cyclase Human genes 0.000 description 4
- 108060000200 adenylate cyclase Proteins 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 239000001961 anticonvulsive agent Substances 0.000 description 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 208000014674 injury Diseases 0.000 description 4
- 208000028867 ischemia Diseases 0.000 description 4
- 230000001537 neural effect Effects 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- 208000018737 Parkinson disease Diseases 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 206010013663 drug dependence Diseases 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 201000000980 schizophrenia Diseases 0.000 description 3
- 230000008733 trauma Effects 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 2
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- 108090000312 Calcium Channels Proteins 0.000 description 2
- 102000003922 Calcium Channels Human genes 0.000 description 2
- 241000282465 Canis Species 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- 208000023105 Huntington disease Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 102000014384 Type C Phospholipases Human genes 0.000 description 2
- 108010079194 Type C Phospholipases Proteins 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 229940025084 amphetamine Drugs 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 239000000164 antipsychotic agent Substances 0.000 description 2
- 229940005529 antipsychotics Drugs 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 229930003827 cannabinoid Natural products 0.000 description 2
- 239000003557 cannabinoid Substances 0.000 description 2
- 229940065144 cannabinoids Drugs 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229960003920 cocaine Drugs 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 229960004756 ethanol Drugs 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229940035363 muscle relaxants Drugs 0.000 description 2
- 208000031225 myocardial ischemia Diseases 0.000 description 2
- 239000003158 myorelaxant agent Substances 0.000 description 2
- 210000002569 neuron Anatomy 0.000 description 2
- 230000004112 neuroprotection Effects 0.000 description 2
- 239000002858 neurotransmitter agent Substances 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- 229940005483 opioid analgesics Drugs 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- 230000035790 physiological processes and functions Effects 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000003379 purinergic P1 receptor agonist Substances 0.000 description 2
- 230000029058 respiratory gaseous exchange Effects 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 229940125723 sedative agent Drugs 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ORQSHDBLTKVMEJ-UHFFFAOYSA-N 2-(2-ethoxyethylamino)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(NCCOCC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 ORQSHDBLTKVMEJ-UHFFFAOYSA-N 0.000 description 1
- FOFSLOBBAFKKQU-UHFFFAOYSA-N 2-(benzylamino)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(NCC=4C=CC=CC=4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 FOFSLOBBAFKKQU-UHFFFAOYSA-N 0.000 description 1
- CFQYBPNCKQWKPB-UHFFFAOYSA-N 2-(butylaminomethyl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(CNCCCC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 CFQYBPNCKQWKPB-UHFFFAOYSA-N 0.000 description 1
- MFSQQXGGJFSYHT-UHFFFAOYSA-N 2-(diethylaminomethyl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(CN(CC)CC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 MFSQQXGGJFSYHT-UHFFFAOYSA-N 0.000 description 1
- GGGSSZGOJCMTAE-UHFFFAOYSA-N 2-[(cyclopropylmethylamino)methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(CNCC4CC4)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 GGGSSZGOJCMTAE-UHFFFAOYSA-N 0.000 description 1
- KTWMJWRPEVYYCK-UHFFFAOYSA-N 2-[2-methoxyethyl(methyl)amino]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(N(C)CCOC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 KTWMJWRPEVYYCK-UHFFFAOYSA-N 0.000 description 1
- MGHPVBURIJGKJK-UHFFFAOYSA-N 2-[benzyl(methyl)amino]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(N=CC=3)N(C)CC=3C=CC=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 MGHPVBURIJGKJK-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229940122614 Adenosine receptor agonist Drugs 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 208000007204 Brain death Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 102000000844 Cell Surface Receptors Human genes 0.000 description 1
- 108010001857 Cell Surface Receptors Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010013654 Drug abuse Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108091006027 G proteins Proteins 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 208000016285 Movement disease Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000009328 Perro Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102000004257 Potassium Channel Human genes 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 102100028255 Renin Human genes 0.000 description 1
- 108090000783 Renin Proteins 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- MMWCIQZXVOZEGG-HOZKJCLWSA-N [(1S,2R,3S,4S,5R,6S)-2,3,5-trihydroxy-4,6-diphosphonooxycyclohexyl] dihydrogen phosphate Chemical compound O[C@H]1[C@@H](O)[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](O)[C@H]1OP(O)(O)=O MMWCIQZXVOZEGG-HOZKJCLWSA-N 0.000 description 1
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001466 anti-adreneric effect Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 229940005530 anxiolytics Drugs 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000006931 brain damage Effects 0.000 description 1
- 231100000874 brain damage Toxicity 0.000 description 1
- 230000003925 brain function Effects 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229940045200 cardioprotective agent Drugs 0.000 description 1
- 239000012659 cardioprotective agent Substances 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 230000019522 cellular metabolic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003596 drug target Substances 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 230000037149 energy metabolism Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000003371 gabaergic effect Effects 0.000 description 1
- 230000024924 glomerular filtration Effects 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 210000005003 heart tissue Anatomy 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- GZQCMUZNSVVYSP-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-[2-(2-oxopyrrolidin-1-yl)ethoxy]pyridine-4-carboxamide Chemical compound C1=2SC(NC(=O)C=3C=C(OCCN4C(CCC4)=O)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 GZQCMUZNSVVYSP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000008062 neuronal firing Effects 0.000 description 1
- 239000004090 neuroprotective agent Substances 0.000 description 1
- 230000003957 neurotransmitter release Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 108020001213 potassium channel Proteins 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000008327 renal blood flow Effects 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 239000003169 respiratory stimulant agent Substances 0.000 description 1
- 229940066293 respiratory stimulants Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 201000009032 substance abuse Diseases 0.000 description 1
- 231100000736 substance abuse Toxicity 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- XOVMEVUHRJFFNT-UHFFFAOYSA-N tert-butyl 4-[[4-[(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)carbamoyl]pyridin-2-yl]methylamino]butanoate Chemical compound C1=2SC(NC(=O)C=3C=C(CNCCCC(=O)OC(C)(C)C)N=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 XOVMEVUHRJFFNT-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
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/14—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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01127312 | 2001-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200403817B true ZA200403817B (en) | 2005-05-23 |
Family
ID=8179263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200403817A ZA200403817B (en) | 2001-11-19 | 2004-05-18 | Nicotin-or isonicotin benzothiazole derivatives. |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US6620811B2 (es) |
| EP (1) | EP1448198B1 (es) |
| JP (1) | JP4226474B2 (es) |
| KR (1) | KR100577110B1 (es) |
| CN (1) | CN100546580C (es) |
| AR (1) | AR039367A1 (es) |
| AT (1) | ATE376831T1 (es) |
| AU (1) | AU2002351955B2 (es) |
| BR (1) | BR0214245A (es) |
| CA (1) | CA2467552C (es) |
| DE (1) | DE60223278T2 (es) |
| DK (1) | DK1448198T3 (es) |
| EA (1) | EA007502B1 (es) |
| EC (1) | ECSP045109A (es) |
| ES (1) | ES2294187T3 (es) |
| GT (1) | GT200200232A (es) |
| HR (1) | HRP20040396A2 (es) |
| HU (1) | HUP0402161A3 (es) |
| IL (2) | IL161623A0 (es) |
| JO (1) | JO2290B1 (es) |
| MA (1) | MA27083A1 (es) |
| MX (1) | MXPA04004684A (es) |
| MY (1) | MY126176A (es) |
| NO (1) | NO20042576L (es) |
| NZ (1) | NZ532802A (es) |
| PA (1) | PA8558001A1 (es) |
| PE (1) | PE20030713A1 (es) |
| PL (1) | PL369517A1 (es) |
| PT (1) | PT1448198E (es) |
| RS (1) | RS39904A (es) |
| RU (1) | RU2294933C2 (es) |
| SI (1) | SI1448198T1 (es) |
| TN (1) | TNSN04087A1 (es) |
| TW (1) | TW200407134A (es) |
| UA (1) | UA77462C2 (es) |
| UY (1) | UY27542A1 (es) |
| WO (1) | WO2003043636A1 (es) |
| ZA (1) | ZA200403817B (es) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU96502A (sh) * | 2000-06-21 | 2006-01-16 | F. Hoffmann-La Roche Ag. | Derivati benzotiazola |
| DK2266558T3 (en) * | 2001-06-07 | 2017-07-31 | Analgesic Neuropharmaceuticals Llc | TREATMENT OF NEUROPATHIC PAIN WITH RECEPTOR ANTAGONIST: N-METHYL-D-ASPARTATE (NMDA) |
| US6734179B2 (en) * | 2001-12-12 | 2004-05-11 | Hoffmann-La Roche Inc. | Benzothiazoles |
| US7390813B1 (en) | 2001-12-21 | 2008-06-24 | Xenon Pharmaceuticals Inc. | Pyridylpiperazines and aminonicotinamides and their use as therapeutic agents |
| US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
| US6872833B2 (en) | 2003-04-14 | 2005-03-29 | Hoffmann-La Roche Inc. | Adenosine receptor ligands |
| CA2533598C (en) * | 2003-07-23 | 2012-09-11 | Synta Pharmaceuticals, Corp. | Method for modulating calcium ion-release-activated calcium ion channels |
| AU2004261252C1 (en) | 2003-07-30 | 2009-09-17 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
| KR20060058132A (ko) | 2003-09-19 | 2006-05-29 | 에프. 호프만-라 로슈 아게 | 아데노신 수용체 리간드로서의 싸이아졸로피리딘 유도체 |
| EP1677791A4 (en) * | 2003-10-31 | 2007-08-15 | Takeda Pharmaceutical | NITROGENIC CONDENSED HETEROCYCLIC COMPOUNDS |
| AU2004309279B2 (en) | 2003-12-26 | 2010-07-15 | Kyowa Kirin Co., Ltd. | Thiazole derivative |
| CA2573198A1 (en) * | 2004-07-06 | 2006-02-09 | Xenon Pharmaceuticals Inc. | Nicotinamide derivatives and their use as therapeutic agents |
| EP1773795A1 (en) * | 2004-07-22 | 2007-04-18 | F.Hoffmann-La Roche Ag | Substituted benzothiazoles |
| KR100823799B1 (ko) * | 2004-07-22 | 2008-04-21 | 에프. 호프만-라 로슈 아게 | 벤조티아졸 유도체 |
| SG140605A1 (en) * | 2004-07-22 | 2008-03-28 | Hoffmann La Roche | Benzothiazole derivatives |
| MX2007003330A (es) † | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
| AR051094A1 (es) * | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| JP4958785B2 (ja) * | 2004-09-20 | 2012-06-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 複素環誘導体およびステアロイル−ＣｏＡデサチュラーゼインヒビターとしてのそれらの使用 |
| WO2006034441A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| CA2580844A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-coa desaturase |
| MX2007003329A (es) * | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y biciclicos y su uso como inhibidores de estearoil-coa-desaturasa (scd). |
| CN101084211A (zh) * | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为治疗剂的用途 |
| US7767677B2 (en) * | 2004-09-20 | 2010-08-03 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| US7919496B2 (en) | 2004-09-20 | 2011-04-05 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-CoA desaturase enzymes |
| DE602005008095D1 (de) * | 2004-11-05 | 2008-08-21 | Hoffmann La Roche | Verfahren zur herstellung von isonikotinsäurederivaten |
| AU2006223070B2 (en) * | 2005-03-14 | 2012-02-09 | High Point Pharmaceuticals, Llc | Benzazole derivatives, compositions, and methods of use as B-secretase inhibitors |
| EP2540296A1 (en) * | 2005-06-03 | 2013-01-02 | Xenon Pharmaceuticals Inc. | Arminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| CN101583593A (zh) * | 2006-11-13 | 2009-11-18 | 辉瑞产品公司 | 二芳基、二吡啶基和芳基-吡啶基衍生物及其用途 |
| WO2010126743A1 (en) | 2009-04-27 | 2010-11-04 | High Point Pharmaceuticals, Llc | SUBSTITUTED ISOQUINOLINE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE AS β-SECRETASE INHIBITORS |
| TWI548411B (zh) | 2009-04-28 | 2016-09-11 | Kyowa Hakko Kirin Co Ltd | Exercise disorder treatment |
| UA110097C2 (uk) | 2009-09-02 | 2015-11-25 | Терапевтичний агент для лікування розладів настрою | |
| UA113383C2 (xx) | 2009-09-02 | 2017-01-25 | Терапевтичний агент для лікування тривожних розладів | |
| US8450354B2 (en) * | 2010-03-23 | 2013-05-28 | High Point Pharmaceuticals, Llc | Substituted imidazo[1,2-b]pyridazine derivatives, pharmaceutical compositions, and methods of use as β-secretase inhibitors |
| JP5248585B2 (ja) * | 2010-12-15 | 2013-07-31 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 治療薬としてのニコチンアミド誘導体およびそれらの使用 |
| DE102011005232A1 (de) | 2011-03-08 | 2012-09-13 | AristoCon GmbH & Co. KG | Adenosin und seine Derivate zur Verwendung in der Schmerztherapie |
| PT2903968T (pt) | 2012-10-02 | 2017-03-13 | Gilead Sciences Inc | Inibidores de desmetilases de histonas |
| WO2020103930A1 (zh) * | 2018-11-22 | 2020-05-28 | 上海科技大学 | 噻唑并环类化合物、其制备方法、中间体和应用 |
| DE102019110904B4 (de) * | 2019-04-26 | 2022-01-20 | Helmholtz-Zentrum Dresden - Rossendorf E. V. | N-(4-methoxy-7-morpholinobenzo[d]thiazol-2-yl)-acetamid-Derivate und deren Verwendung |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3374550D1 (en) | 1982-12-21 | 1987-12-23 | Johnsen Jorgensen Plastics Ltd | Dispensing container |
| FI91859C (fi) | 1987-06-17 | 1994-08-25 | Eisai Co Ltd | Analogiamenetelmä antiallergisena aineena aktiivisen bentsotiatsolijohdannaisen valmistamiseksi |
| IL90337A0 (en) * | 1988-05-24 | 1989-12-15 | Pfizer | Aromatic and heterocyclic carboxamide derivatives as antineoplastic agents |
| YU96502A (sh) * | 2000-06-21 | 2006-01-16 | F. Hoffmann-La Roche Ag. | Derivati benzotiazola |
-
2002
- 2002-11-05 US US10/288,100 patent/US6620811B2/en not_active Expired - Lifetime
- 2002-11-11 WO PCT/EP2002/012562 patent/WO2003043636A1/en not_active Ceased
- 2002-11-11 DE DE60223278T patent/DE60223278T2/de not_active Expired - Lifetime
- 2002-11-11 CA CA2467552A patent/CA2467552C/en not_active Expired - Fee Related
- 2002-11-11 AT AT02787632T patent/ATE376831T1/de active
- 2002-11-11 HR HR20040396A patent/HRP20040396A2/hr not_active Application Discontinuation
- 2002-11-11 RS YU39904A patent/RS39904A/sr unknown
- 2002-11-11 HU HU0402161A patent/HUP0402161A3/hu not_active Application Discontinuation
- 2002-11-11 IL IL16162302A patent/IL161623A0/xx unknown
- 2002-11-11 DK DK02787632T patent/DK1448198T3/da active
- 2002-11-11 ES ES02787632T patent/ES2294187T3/es not_active Expired - Lifetime
- 2002-11-11 SI SI200230637T patent/SI1448198T1/sl unknown
- 2002-11-11 NZ NZ532802A patent/NZ532802A/en unknown
- 2002-11-11 AU AU2002351955A patent/AU2002351955B2/en not_active Ceased
- 2002-11-11 CN CNB028228391A patent/CN100546580C/zh not_active Expired - Fee Related
- 2002-11-11 UA UA20040604552A patent/UA77462C2/uk unknown
- 2002-11-11 PL PL02369517A patent/PL369517A1/xx not_active Application Discontinuation
- 2002-11-11 BR BR0214245-7A patent/BR0214245A/pt not_active IP Right Cessation
- 2002-11-11 EP EP02787632A patent/EP1448198B1/en not_active Expired - Lifetime
- 2002-11-11 KR KR1020047007638A patent/KR100577110B1/ko not_active Expired - Fee Related
- 2002-11-11 JP JP2003545317A patent/JP4226474B2/ja not_active Expired - Fee Related
- 2002-11-11 EA EA200400598A patent/EA007502B1/ru not_active IP Right Cessation
- 2002-11-11 RU RU2004118425/04A patent/RU2294933C2/ru not_active IP Right Cessation
- 2002-11-11 MX MXPA04004684A patent/MXPA04004684A/es active IP Right Grant
- 2002-11-11 PT PT02787632T patent/PT1448198E/pt unknown
- 2002-11-14 PA PA20028558001A patent/PA8558001A1/es unknown
- 2002-11-14 TW TW091133371A patent/TW200407134A/zh unknown
- 2002-11-15 PE PE2002001104A patent/PE20030713A1/es not_active Application Discontinuation
- 2002-11-18 AR ARP020104416A patent/AR039367A1/es unknown
- 2002-11-18 UY UY27542A patent/UY27542A1/es not_active Application Discontinuation
- 2002-11-18 MY MYPI20024303A patent/MY126176A/en unknown
- 2002-11-18 JO JO2002114A patent/JO2290B1/en active
- 2002-11-18 GT GT200200232A patent/GT200200232A/es unknown
-
2004
- 2004-04-26 IL IL161623A patent/IL161623A/en not_active IP Right Cessation
- 2004-05-17 EC EC2004005109A patent/ECSP045109A/es unknown
- 2004-05-18 MA MA27681A patent/MA27083A1/fr unknown
- 2004-05-18 TN TNP2004000087A patent/TNSN04087A1/en unknown
- 2004-05-18 ZA ZA200403817A patent/ZA200403817B/en unknown
- 2004-06-18 NO NO20042576A patent/NO20042576L/no not_active Application Discontinuation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200403817B (en) | Nicotin-or isonicotin benzothiazole derivatives. | |
| EP1450796B1 (en) | Benzothiazole derivatives | |
| US6713499B2 (en) | 7-Amino-benzothiazole derivatives | |
| AU2002366194B8 (en) | Pyridone Substituted Benzothiazole Derivatives | |
| AU2005247567B2 (en) | 4-hydroxy-4-methyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide | |
| CA2468311C (en) | Benzothiazole derivatives | |
| AU2005263500B2 (en) | Benzothiazole derivatives | |
| EP1636223B1 (en) | Benzothiazole derivatives as adenosine receptor ligands | |
| CA2527174C (en) | Benzothiazole derivatives and use thereof in the treatment of diseases related to the adenosine a2a receptor | |
| AU2005263499B2 (en) | Substituted benzothiazoles |