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
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- 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
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Classifications
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- 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)
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- Bioinformatics & Cheminformatics (AREA)
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- Pharmacology & Pharmacy (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01127312 | 2001-11-19 |
Publications (1)
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| ZA200403817B true ZA200403817B (en) | 2005-05-23 |
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| ZA200403817A ZA200403817B (en) | 2001-11-19 | 2004-05-18 | Nicotin-or isonicotin benzothiazole derivatives. |
Country Status (38)
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| EP (1) | EP1448198B1 (ko) |
| JP (1) | JP4226474B2 (ko) |
| KR (1) | KR100577110B1 (ko) |
| CN (1) | CN100546580C (ko) |
| AR (1) | AR039367A1 (ko) |
| AT (1) | ATE376831T1 (ko) |
| AU (1) | AU2002351955B2 (ko) |
| BR (1) | BR0214245A (ko) |
| CA (1) | CA2467552C (ko) |
| DE (1) | DE60223278T2 (ko) |
| DK (1) | DK1448198T3 (ko) |
| EA (1) | EA007502B1 (ko) |
| EC (1) | ECSP045109A (ko) |
| ES (1) | ES2294187T3 (ko) |
| GT (1) | GT200200232A (ko) |
| HR (1) | HRP20040396A2 (ko) |
| HU (1) | HUP0402161A3 (ko) |
| IL (2) | IL161623A0 (ko) |
| JO (1) | JO2290B1 (ko) |
| MA (1) | MA27083A1 (ko) |
| MX (1) | MXPA04004684A (ko) |
| MY (1) | MY126176A (ko) |
| NO (1) | NO20042576L (ko) |
| NZ (1) | NZ532802A (ko) |
| PA (1) | PA8558001A1 (ko) |
| PE (1) | PE20030713A1 (ko) |
| PL (1) | PL369517A1 (ko) |
| PT (1) | PT1448198E (ko) |
| RS (1) | RS39904A (ko) |
| RU (1) | RU2294933C2 (ko) |
| SI (1) | SI1448198T1 (ko) |
| TN (1) | TNSN04087A1 (ko) |
| TW (1) | TW200407134A (ko) |
| UA (1) | UA77462C2 (ko) |
| UY (1) | UY27542A1 (ko) |
| WO (1) | WO2003043636A1 (ko) |
| ZA (1) | ZA200403817B (ko) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CZ2003182A3 (cs) * | 2000-06-21 | 2003-06-18 | F. Hoffmann-La Roche Ag | Deriváty benzothiazolu |
| ES2357808T3 (es) * | 2001-06-07 | 2011-04-29 | Christine Dr. Sang | Tratamiento del dolor neuropático con antagonistas del receptor de n-metil-d-aspartato (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 |
| AU2004259347B2 (en) * | 2003-07-23 | 2011-02-24 | Synta Pharmaceuticals, Corp. | Method for modulating calcium ion-release-activated calcium ion channels |
| WO2005011655A2 (en) | 2003-07-30 | 2005-02-10 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
| JP2007505851A (ja) * | 2003-09-19 | 2007-03-15 | エフ．ホフマン−ラ ロシュ アーゲー | アデノシン受容体リガンドとしてのチアゾピリジン誘導体 |
| EP1677791A4 (en) * | 2003-10-31 | 2007-08-15 | Takeda Pharmaceutical | NITROGENIC CONDENSED HETEROCYCLIC COMPOUNDS |
| HUE025659T2 (en) | 2003-12-26 | 2016-04-28 | Kyowa Hakko Kirin Co Ltd | Thiazole derivatives |
| CN1997371A (zh) * | 2004-07-06 | 2007-07-11 | 泽农医药公司 | 烟酰胺衍生物及其作为治疗剂的用途 |
| JP5202946B2 (ja) * | 2004-07-22 | 2013-06-05 | エフ．ホフマン−ラ ロシュ アーゲー | ベンゾチアゾール誘導体 |
| KR100823799B1 (ko) * | 2004-07-22 | 2008-04-21 | 에프. 호프만-라 로슈 아게 | 벤조티아졸 유도체 |
| JP2008506735A (ja) | 2004-07-22 | 2008-03-06 | エフ．ホフマン−ラ ロシュ アーゲー | 置換されているベンゾチアゾール類 |
| CA2580787A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
| EP1799668A1 (en) * | 2004-09-20 | 2007-06-27 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-coa desaturase |
| AR051294A1 (es) * | 2004-09-20 | 2007-01-03 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| US7592343B2 (en) * | 2004-09-20 | 2009-09-22 | Xenon Pharmaceuticals Inc. | Pyridazine-piperazine compounds and their use as stearoyl-CoA desaturase inhibitors |
| BRPI0515488A (pt) * | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados de heterocìclicos e seu uso como agentes terapêuticos |
| WO2006034341A2 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
| JP4958786B2 (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治療薬としてのそれらの使用 |
| US8071603B2 (en) * | 2004-09-20 | 2011-12-06 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| US20080167321A1 (en) * | 2004-09-20 | 2008-07-10 | Xenon Pharmaceuticals Inc. | Pyridine Derivatives For Inhibiting Human Stearoyl-Coa-Desaturase |
| WO2006048172A1 (en) * | 2004-11-05 | 2006-05-11 | F. Hoffmann-La Roche Ag | Process for preparation of isonicotinic acid derivatives |
| JP5066514B2 (ja) * | 2005-03-14 | 2012-11-07 | ハイ ポイント ファーマシューティカルズ，エルエルシー | ベンズアゾール誘導体、組成物及びβ−セクレターゼ阻害剤としての使用方法 |
| BRPI0611187A2 (pt) * | 2005-06-03 | 2010-08-24 | Xenon Pharmaceuticals Inc | derivados aminotiazàis como inibidores da estearoil-coa desaturase humana |
| WO2008059335A1 (en) * | 2006-11-13 | 2008-05-22 | Pfizer Products Inc. | Diaryl, dipyridinyl and aryl-pyridinyl derivatives and uses thereof |
| JP2012525389A (ja) | 2009-04-27 | 2012-10-22 | ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー | 置換イソキノリン誘導体、医薬組成物、及びβ−セクレターゼ阻害剤としての使用方法 |
| TWI548411B (zh) | 2009-04-28 | 2016-09-11 | Kyowa Hakko Kirin Co Ltd | Exercise disorder treatment |
| UA113383C2 (xx) | 2009-09-02 | 2017-01-25 | Терапевтичний агент для лікування тривожних розладів | |
| UA110097C2 (uk) | 2009-09-02 | 2015-11-25 | Терапевтичний агент для лікування розладів настрою | |
| WO2011119465A1 (en) * | 2010-03-23 | 2011-09-29 | High Point Pharmaceuticals, Llc | Substituted imidazo[1,2-b]pyridazine derivatives, pharmaceutical compositions, and methods of use as beta-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 |
| PL2903968T3 (pl) | 2012-10-02 | 2017-05-31 | Gilead Sciences, Inc. | Inhibitory demetylaz histonowych |
| 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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0113219B1 (en) | 1982-12-21 | 1987-11-19 | Johnsen & Jorgensen (Plastics) Limited | Dispensing container |
| FI91859C (fi) | 1987-06-17 | 1994-08-25 | Eisai Co Ltd | Analogiamenetelmä antiallergisena aineena aktiivisen bentsotiatsolijohdannaisen valmistamiseksi |
| CZ2003182A3 (cs) * | 2000-06-21 | 2003-06-18 | F. Hoffmann-La Roche Ag | Deriváty benzothiazolu |
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