HRP20040396A2 - Nicotin -or isonicotin benzothiazole derivatives - Google Patents
Nicotin -or isonicotin benzothiazole derivativesInfo
- Publication number
- HRP20040396A2 HRP20040396A2 HR20040396A HRP20040396A HRP20040396A2 HR P20040396 A2 HRP20040396 A2 HR P20040396A2 HR 20040396 A HR20040396 A HR 20040396A HR P20040396 A HRP20040396 A HR P20040396A HR P20040396 A2 HRP20040396 A2 HR P20040396A2
- Authority
- HR
- Croatia
- Prior art keywords
- methoxy
- morpholin
- benzothiazol
- isonicotinamide
- alkyl
- Prior art date
Links
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 title description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 202
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- -1 2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl Chemical group 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 125000002757 morpholinyl group Chemical group 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000003386 piperidinyl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 14
- 102000009346 Adenosine receptors Human genes 0.000 claims description 13
- 108050000203 Adenosine receptors Proteins 0.000 claims description 12
- 125000001246 bromo group Chemical group Br* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 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 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 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 5
- 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 description 5
- 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 5
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 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 4
- 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 description 4
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- JJPIFGNANDULQU-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-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=C1N1CCOCC1 JJPIFGNANDULQU-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 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 3
- 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 description 3
- 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 claims description 3
- 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 3
- WCZSVYXPXYUNLY-UHFFFAOYSA-N 2-(4-acetylpiperazin-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)N3CCN(CC3)C(C)=O)=NC=2C(OC)=CC=C1N1CCOCC1 WCZSVYXPXYUNLY-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- WZOVMGAIOWLVKE-UHFFFAOYSA-N 2-(azetidin-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)N3CCC3)=NC=2C(OC)=CC=C1N1CCOCC1 WZOVMGAIOWLVKE-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 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 claims description 3
- 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 3
- 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 3
- 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 3
- 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 claims description 3
- ULEOBGBTSNNQTQ-UHFFFAOYSA-N 2-(ethylaminomethyl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(CNCC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 ULEOBGBTSNNQTQ-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 3
- 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 claims description 3
- 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 3
- 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 3
- 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 3
- 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 claims description 3
- 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 claims description 3
- 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 description 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- NQEJPBTWUQYSFU-UHFFFAOYSA-N 2-ethylsulfanyl-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(SCC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 NQEJPBTWUQYSFU-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- HGQREKBSTLMXFH-UHFFFAOYSA-N 6-(2-methoxyethoxy)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-3-carboxamide Chemical compound C1=NC(OCCOC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 HGQREKBSTLMXFH-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 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 3
- 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 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 3
- 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 3
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- 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]
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- 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
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- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01127312 | 2001-11-19 | ||
PCT/EP2002/012562 WO2003043636A1 (en) | 2001-11-19 | 2002-11-11 | Nicotin-or isonicotin benzothiazole derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20040396A2 true HRP20040396A2 (en) | 2005-04-30 |
Family
ID=8179263
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20040396A HRP20040396A2 (en) | 2001-11-19 | 2004-05-05 | Nicotin -or isonicotin benzothiazole derivatives |
Country Status (38)
Country | Link |
---|---|
US (1) | US6620811B2 (ru) |
EP (1) | EP1448198B1 (ru) |
JP (1) | JP4226474B2 (ru) |
KR (1) | KR100577110B1 (ru) |
CN (1) | CN100546580C (ru) |
AR (1) | AR039367A1 (ru) |
AT (1) | ATE376831T1 (ru) |
AU (1) | AU2002351955B2 (ru) |
BR (1) | BR0214245A (ru) |
CA (1) | CA2467552C (ru) |
DE (1) | DE60223278T2 (ru) |
DK (1) | DK1448198T3 (ru) |
EA (1) | EA007502B1 (ru) |
EC (1) | ECSP045109A (ru) |
ES (1) | ES2294187T3 (ru) |
GT (1) | GT200200232A (ru) |
HR (1) | HRP20040396A2 (ru) |
HU (1) | HUP0402161A3 (ru) |
IL (2) | IL161623A0 (ru) |
JO (1) | JO2290B1 (ru) |
MA (1) | MA27083A1 (ru) |
MX (1) | MXPA04004684A (ru) |
MY (1) | MY126176A (ru) |
NO (1) | NO20042576L (ru) |
NZ (1) | NZ532802A (ru) |
PA (1) | PA8558001A1 (ru) |
PE (1) | PE20030713A1 (ru) |
PL (1) | PL369517A1 (ru) |
PT (1) | PT1448198E (ru) |
RS (1) | RS39904A (ru) |
RU (1) | RU2294933C2 (ru) |
SI (1) | SI1448198T1 (ru) |
TN (1) | TNSN04087A1 (ru) |
TW (1) | TW200407134A (ru) |
UA (1) | UA77462C2 (ru) |
UY (1) | UY27542A1 (ru) |
WO (1) | WO2003043636A1 (ru) |
ZA (1) | ZA200403817B (ru) |
Families Citing this family (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1303272B1 (en) * | 2000-06-21 | 2008-02-13 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives for the treatment of alzheimer's disease and parkinson's disease |
US8309570B2 (en) * | 2001-06-07 | 2012-11-13 | Analgesic Neuropharmaceuticals, Llc | Treatment of central neuropathic pain |
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 |
PL1651232T3 (pl) * | 2003-07-23 | 2011-05-31 | Synta Pharmaceuticals Corp | Związki do zastosowań związanych z zapaleniami i odpornością |
ES2375134T3 (es) | 2003-07-30 | 2012-02-27 | Xenon Pharmaceuticals Inc. | Derivados de piperazina y su uso como agentes terapéuticos. |
BRPI0414266A (pt) * | 2003-09-19 | 2006-11-07 | Hoffmann La Roche | derivados de tiazolopiridina como ligandos receptores da adenosina |
CA2543707A1 (en) | 2003-10-31 | 2005-05-19 | Takeda Pharmaceutical Company Limited | Nitrogen-containing fused heterocyclic compounds |
SI1700856T1 (sl) | 2003-12-26 | 2016-02-29 | Kyowa Hakko Kirin Co., Ltd., | Tiazolni derivat |
ATE537830T1 (de) * | 2004-07-06 | 2012-01-15 | Xenon Pharmaceuticals Inc | Nicotinamid derivate und ihre verwendung als therapeutika |
ATE457986T1 (de) * | 2004-07-22 | 2010-03-15 | Hoffmann La Roche | Benzothiazolderivate |
KR100823799B1 (ko) * | 2004-07-22 | 2008-04-21 | 에프. 호프만-라 로슈 아게 | 벤조티아졸 유도체 |
MX2007000635A (es) * | 2004-07-22 | 2007-03-07 | Hoffmann La Roche | Benzotiazoles sustituidos. |
MX2007003318A (es) | 2004-09-20 | 2007-05-18 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
JP5094398B2 (ja) * | 2004-09-20 | 2012-12-12 | 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 | 複素環式誘導体およびステアロイル−CoAデサチュラーゼのメディエータとしてのそれらの使用 |
WO2006034312A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Bicyclic heterocyclic derivatives and their use as inhibitors of stearoyl-coa-desaturase (scd) |
CA2580857A1 (en) * | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
TW200626138A (en) * | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
WO2006034341A2 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
WO2006034441A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
EP2316457A1 (en) * | 2004-09-20 | 2011-05-04 | Xenon Pharmaceuticals Inc. | Pyridine derivatives for inhibiting human stearoyl-coa-desaturase |
WO2006034440A2 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
US7459563B2 (en) * | 2004-11-05 | 2008-12-02 | Hoffmann-La Roche Inc. | Process for the preparation of isonicotinic acid derivatives |
EP2457901A1 (en) * | 2005-03-14 | 2012-05-30 | High Point Pharmaceuticals, LLC | Benzazole derivatives, compositions, and methods of use as B-secretase inhibitors |
AU2006343359A1 (en) * | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
KR20090064478A (ko) * | 2006-11-13 | 2009-06-18 | 화이자 프로덕츠 인크. | 디아릴, 디피리디닐 및 아릴-피리디닐 유도체, 및 이들의 용도 |
CA2758961A1 (en) | 2009-04-27 | 2010-11-04 | High Point Pharmaceuticals, Llc | Substituted isoquinoline derivatives, pharmaceutical compositions, and methods of use as .beta.-secretase inhibitors |
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 | |
CA2792339A1 (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 |
NZ706635A (en) * | 2012-10-02 | 2018-08-31 | Gilead Sciences Inc | Inhibitors of histone demethylases |
CN111205244B (zh) * | 2018-11-22 | 2023-08-18 | 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 |
---|---|---|---|---|
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 |
EP1303272B1 (en) * | 2000-06-21 | 2008-02-13 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives for the treatment of alzheimer's disease and parkinson's disease |
-
2002
- 2002-11-05 US US10/288,100 patent/US6620811B2/en not_active Expired - Lifetime
- 2002-11-11 KR KR1020047007638A patent/KR100577110B1/ko not_active IP Right Cessation
- 2002-11-11 RS YU39904A patent/RS39904A/sr unknown
- 2002-11-11 UA UA20040604552A patent/UA77462C2/uk unknown
- 2002-11-11 DK DK02787632T patent/DK1448198T3/da active
- 2002-11-11 EA EA200400598A patent/EA007502B1/ru not_active IP Right Cessation
- 2002-11-11 JP JP2003545317A patent/JP4226474B2/ja not_active Expired - Fee Related
- 2002-11-11 DE DE60223278T patent/DE60223278T2/de not_active Expired - Lifetime
- 2002-11-11 WO PCT/EP2002/012562 patent/WO2003043636A1/en active IP Right Grant
- 2002-11-11 CA CA2467552A patent/CA2467552C/en not_active Expired - Fee Related
- 2002-11-11 PT PT02787632T patent/PT1448198E/pt unknown
- 2002-11-11 HU HU0402161A patent/HUP0402161A3/hu not_active Application Discontinuation
- 2002-11-11 ES ES02787632T patent/ES2294187T3/es not_active Expired - Lifetime
- 2002-11-11 CN CNB028228391A patent/CN100546580C/zh not_active Expired - Fee Related
- 2002-11-11 NZ NZ532802A patent/NZ532802A/en unknown
- 2002-11-11 EP EP02787632A patent/EP1448198B1/en not_active Expired - Lifetime
- 2002-11-11 PL PL02369517A patent/PL369517A1/xx not_active Application Discontinuation
- 2002-11-11 SI SI200230637T patent/SI1448198T1/sl unknown
- 2002-11-11 MX MXPA04004684A patent/MXPA04004684A/es active IP Right Grant
- 2002-11-11 AT AT02787632T patent/ATE376831T1/de active
- 2002-11-11 IL IL16162302A patent/IL161623A0/xx unknown
- 2002-11-11 RU RU2004118425/04A patent/RU2294933C2/ru not_active IP Right Cessation
- 2002-11-11 AU AU2002351955A patent/AU2002351955B2/en not_active Ceased
- 2002-11-11 BR BR0214245-7A patent/BR0214245A/pt not_active IP Right Cessation
- 2002-11-14 TW TW091133371A patent/TW200407134A/zh unknown
- 2002-11-14 PA PA20028558001A patent/PA8558001A1/es unknown
- 2002-11-15 PE PE2002001104A patent/PE20030713A1/es not_active Application Discontinuation
- 2002-11-18 GT GT200200232A patent/GT200200232A/es unknown
- 2002-11-18 UY UY27542A patent/UY27542A1/es not_active Application Discontinuation
- 2002-11-18 AR ARP020104416A patent/AR039367A1/es unknown
- 2002-11-18 MY MYPI20024303A patent/MY126176A/en unknown
- 2002-11-18 JO JO2002114A patent/JO2290B1/en active
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2004
- 2004-04-26 IL IL161623A patent/IL161623A/en not_active IP Right Cessation
- 2004-05-05 HR HR20040396A patent/HRP20040396A2/hr not_active Application Discontinuation
- 2004-05-17 EC EC2004005109A patent/ECSP045109A/es unknown
- 2004-05-18 MA MA27681A patent/MA27083A1/fr unknown
- 2004-05-18 ZA ZA200403817A patent/ZA200403817B/en unknown
- 2004-05-18 TN TNP2004000087A patent/TNSN04087A1/en unknown
- 2004-06-18 NO NO20042576A patent/NO20042576L/no not_active Application Discontinuation
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