NO324635B1 - Benzotiazolderivater, fremstilling av disse, anvendelse av slike for fremstilling av medikamenter for behandling av sykdom samt medikament inneholdende slike forbindelser - Google Patents
Benzotiazolderivater, fremstilling av disse, anvendelse av slike for fremstilling av medikamenter for behandling av sykdom samt medikament inneholdende slike forbindelser Download PDFInfo
- Publication number
- NO324635B1 NO324635B1 NO20025978A NO20025978A NO324635B1 NO 324635 B1 NO324635 B1 NO 324635B1 NO 20025978 A NO20025978 A NO 20025978A NO 20025978 A NO20025978 A NO 20025978A NO 324635 B1 NO324635 B1 NO 324635B1
- Authority
- NO
- Norway
- Prior art keywords
- methoxy
- benzothiazol
- benzamide
- methyl
- phenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 282
- 239000003814 drug Substances 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 229940079593 drug Drugs 0.000 title claims description 9
- 201000010099 disease Diseases 0.000 title description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims description 57
- -1 azepan-1-yl Chemical group 0.000 claims description 46
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 45
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 36
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- KYPGODAIYIMXKT-UHFFFAOYSA-N 4-fluoro-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(F)=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 KYPGODAIYIMXKT-UHFFFAOYSA-N 0.000 claims description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 206010021143 Hypoxia Diseases 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 230000007954 hypoxia Effects 0.000 claims description 10
- 208000028867 ischemia Diseases 0.000 claims description 10
- 206010020751 Hypersensitivity Diseases 0.000 claims description 9
- 208000018737 Parkinson disease Diseases 0.000 claims description 9
- 208000006673 asthma Diseases 0.000 claims description 9
- 230000004112 neuroprotection Effects 0.000 claims description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 8
- 208000006011 Stroke Diseases 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 8
- 230000036407 pain Effects 0.000 claims description 8
- 201000000980 schizophrenia Diseases 0.000 claims description 8
- 201000009032 substance abuse Diseases 0.000 claims description 8
- 231100000736 substance abuse Toxicity 0.000 claims description 8
- 208000011117 substance-related disease Diseases 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 208000004756 Respiratory Insufficiency Diseases 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 201000004193 respiratory failure Diseases 0.000 claims description 7
- 125000005605 benzo group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- VEHWZDFLDCERBM-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4-(methylaminomethyl)benzamide Chemical compound C1=CC(CNC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 VEHWZDFLDCERBM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- QWMBZRZDPAXYTF-UHFFFAOYSA-N 4-(hydroxymethyl)-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CO)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 QWMBZRZDPAXYTF-UHFFFAOYSA-N 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- UHUICRMEVKTTGT-UHFFFAOYSA-N n-(4-methoxy-7-thiomorpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC=CC=3)=NC=2C(OC)=CC=C1N1CCSCC1 UHUICRMEVKTTGT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
- KRVYMJBQDLNWEL-UHFFFAOYSA-N 4-[(2-methoxyethylamino)methyl]-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=CC(CNCCOC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(C=3C=CC=CC=3)=C2S1 KRVYMJBQDLNWEL-UHFFFAOYSA-N 0.000 claims description 4
- QEHJOXFNOQYDIG-UHFFFAOYSA-N 4-[(4-hydroxypiperidin-1-yl)methyl]-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN4CCC(O)CC4)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 QEHJOXFNOQYDIG-UHFFFAOYSA-N 0.000 claims description 4
- JDIPCXLCIPCFMU-UHFFFAOYSA-N 4-[2-(dimethylamino)ethylsulfanylmethyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CSCCN(C)C)=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 JDIPCXLCIPCFMU-UHFFFAOYSA-N 0.000 claims description 4
- MEUOPNIKWUHUCN-QFIPXVFZSA-N 4-[[(3s)-3-(dimethylamino)pyrrolidin-1-yl]methyl]-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN4C[C@H](CC4)N(C)C)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 MEUOPNIKWUHUCN-QFIPXVFZSA-N 0.000 claims description 4
- JAKPDYWRJCAIOR-UHFFFAOYSA-N 4-[[2-ethoxyethyl(ethyl)amino]methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=CC(CN(CC)CCOCC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 JAKPDYWRJCAIOR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- JARKJCRZRAPTDZ-UHFFFAOYSA-N methyl 2-[(4-fluorobenzoyl)amino]-4-methoxy-1,3-benzothiazole-7-carboxylate Chemical compound S1C=2C(C(=O)OC)=CC=C(OC)C=2N=C1NC(=O)C1=CC=C(F)C=C1 JARKJCRZRAPTDZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 4
- KEJUVOFMRNLHJQ-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 KEJUVOFMRNLHJQ-UHFFFAOYSA-N 0.000 claims description 4
- NYTAXFRCDRSVFS-UHFFFAOYSA-N n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)-4-[(pyridin-4-ylmethylamino)methyl]benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CNCC=4C=CN=CC=4)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 NYTAXFRCDRSVFS-UHFFFAOYSA-N 0.000 claims description 4
- KJQLKXGPBVTCPP-UHFFFAOYSA-N n-[4-methoxy-7-[2-(6-methylpyridin-3-yl)-1,3-thiazol-4-yl]-1,3-benzothiazol-2-yl]-2-methyl-4-pyrrolidin-1-ylbenzamide Chemical compound C1=2SC(NC(=O)C=3C(=CC(=CC=3)N3CCCC3)C)=NC=2C(OC)=CC=C1C(N=1)=CSC=1C1=CC=C(C)N=C1 KJQLKXGPBVTCPP-UHFFFAOYSA-N 0.000 claims description 4
- JXWFTVZYGPPHPK-UHFFFAOYSA-N n-[7-(2-amino-1,3-thiazol-4-yl)-4-methoxy-1,3-benzothiazol-2-yl]-4-fluorobenzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(F)=CC=3)=NC=2C(OC)=CC=C1C1=CSC(N)=N1 JXWFTVZYGPPHPK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 3
- VFPNTXSBUIMXPE-UHFFFAOYSA-N 3-[(2-methoxyethylamino)methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound COCCNCC1=CC=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 VFPNTXSBUIMXPE-UHFFFAOYSA-N 0.000 claims description 3
- GGVGEZXMJXRCEU-UHFFFAOYSA-N 3-[[2-methoxyethyl(methyl)amino]methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound COCCN(C)CC1=CC=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 GGVGEZXMJXRCEU-UHFFFAOYSA-N 0.000 claims description 3
- BWALCOILYZRIII-UHFFFAOYSA-N 4-(2-methoxyethoxymethyl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=CC(COCCOC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 BWALCOILYZRIII-UHFFFAOYSA-N 0.000 claims description 3
- YTOSWUCZMFQXPJ-UHFFFAOYSA-N 4-(aminomethyl)-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 YTOSWUCZMFQXPJ-UHFFFAOYSA-N 0.000 claims description 3
- PBKWNISRGRRYNU-UHFFFAOYSA-N 4-(methoxymethyl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=CC(COC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 PBKWNISRGRRYNU-UHFFFAOYSA-N 0.000 claims description 3
- GUQXEIKVQCXRQL-UHFFFAOYSA-N 4-[[2-ethoxyethyl(methyl)amino]methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=CC(CN(C)CCOCC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 GUQXEIKVQCXRQL-UHFFFAOYSA-N 0.000 claims description 3
- UEUGIJULIDQKSX-UHFFFAOYSA-N 4-[[2-methoxyethyl(methyl)amino]methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=CC(CN(C)CCOC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 UEUGIJULIDQKSX-UHFFFAOYSA-N 0.000 claims description 3
- WLSJBSMKWNWGPI-UHFFFAOYSA-N 4-[[2-methoxyethyl(methyl)amino]methyl]-n-(4-methoxy-7-thiophen-2-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=CC(CN(C)CCOC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(C=3SC=CC=3)=C2S1 WLSJBSMKWNWGPI-UHFFFAOYSA-N 0.000 claims description 3
- KZSGKUSHDIJKAH-UHFFFAOYSA-N 4-[[2-methoxyethyl(methyl)amino]methyl]-n-[4-methoxy-7-(2-pyridin-2-yl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-yl]benzamide Chemical compound C1=CC(CN(C)CCOC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(C=3N=C(SC=3)C=3N=CC=CC=3)=C2S1 KZSGKUSHDIJKAH-UHFFFAOYSA-N 0.000 claims description 3
- NPTVJEMEOINUKA-UHFFFAOYSA-N 4-[[2-methoxyethyl(methyl)amino]methyl]-n-[4-methoxy-7-[2-(6-methylpyridin-3-yl)-1,3-thiazol-4-yl]-1,3-benzothiazol-2-yl]benzamide Chemical compound C1=CC(CN(C)CCOC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(C=3N=C(SC=3)C=3C=NC(C)=CC=3)=C2S1 NPTVJEMEOINUKA-UHFFFAOYSA-N 0.000 claims description 3
- LDJJYROTZMTMIN-UHFFFAOYSA-N 4-chloro-3-[(2-methoxyethylamino)methyl]-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=C(Cl)C(CNCCOC)=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=C1 LDJJYROTZMTMIN-UHFFFAOYSA-N 0.000 claims description 3
- MKKPOTULIHKQAY-UHFFFAOYSA-N 4-chloro-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-methyl-3-pyrrolidin-1-ylbenzamide Chemical compound C1=2SC(NC(=O)C=3C(=C(N4CCCC4)C(Cl)=CC=3)C)=NC=2C(OC)=CC=C1N1CCOCC1 MKKPOTULIHKQAY-UHFFFAOYSA-N 0.000 claims description 3
- XFNHDSINBXOVKV-UHFFFAOYSA-N 4-fluoro-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(F)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 XFNHDSINBXOVKV-UHFFFAOYSA-N 0.000 claims description 3
- JQKBYRBSVQPASR-UHFFFAOYSA-N 4-fluoro-n-(4-methoxy-7-thiophen-2-yl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(F)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CS1 JQKBYRBSVQPASR-UHFFFAOYSA-N 0.000 claims description 3
- ZQXSTQFCHLFWFB-UHFFFAOYSA-N 4-fluoro-n-[4-methoxy-7-[2-(6-methylpyridin-3-yl)-1,3-thiazol-4-yl]-1,3-benzothiazol-2-yl]benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(F)=CC=3)=NC=2C(OC)=CC=C1C(N=1)=CSC=1C1=CC=C(C)N=C1 ZQXSTQFCHLFWFB-UHFFFAOYSA-N 0.000 claims description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 3
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- MWUUSBWKKMKSDN-UHFFFAOYSA-N methyl n-[[4-[(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)carbamoyl]phenyl]methyl]-n-methylcarbamate Chemical compound C1=CC(CN(C)C(=O)OC)=CC=C1C(=O)NC1=NC2=C(OC)C=CC(N3CCOCC3)=C2S1 MWUUSBWKKMKSDN-UHFFFAOYSA-N 0.000 claims description 3
- GJAAOLKLYVTDTK-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-methyl-3-pyrrolidin-1-ylbenzamide Chemical compound C1=2SC(NC(=O)C=3C(=C(N4CCCC4)C=CC=3)C)=NC=2C(OC)=CC=C1N1CCOCC1 GJAAOLKLYVTDTK-UHFFFAOYSA-N 0.000 claims description 3
- YYPCSESDMWDOFG-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4-(trifluoromethyl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(=CC=3)C(F)(F)F)=NC=2C(OC)=CC=C1N1CCOCC1 YYPCSESDMWDOFG-UHFFFAOYSA-N 0.000 claims description 3
- ZWNDFSJRYITZEO-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4-[(2-methylimidazol-1-yl)methyl]benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN4C(=NC=C4)C)=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 ZWNDFSJRYITZEO-UHFFFAOYSA-N 0.000 claims description 3
- BRCDUYGLCKTGBB-UHFFFAOYSA-N n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-4-[(4-methylpiperazin-1-yl)methyl]benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN4CCN(C)CC4)=CC=3)=NC=2C(OC)=CC=C1N1CCOCC1 BRCDUYGLCKTGBB-UHFFFAOYSA-N 0.000 claims description 3
- OCUSKKKYPLDSAK-UHFFFAOYSA-N n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)-4-[(2-methylsulfanylethylamino)methyl]benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CNCCSC)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 OCUSKKKYPLDSAK-UHFFFAOYSA-N 0.000 claims description 3
- UCMBQXLDTHGFHS-UHFFFAOYSA-N n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)-4-[(pyridin-3-ylmethylamino)methyl]benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CNCC=4C=NC=CC=4)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 UCMBQXLDTHGFHS-UHFFFAOYSA-N 0.000 claims description 3
- NZBIKEZYGQOFQF-UHFFFAOYSA-N n-[4-methoxy-7-(2-pyridin-2-yl-1,3-thiazol-4-yl)-1,3-benzothiazol-2-yl]-2-methyl-4-pyrrolidin-1-ylbenzamide Chemical compound C1=2SC(NC(=O)C=3C(=CC(=CC=3)N3CCCC3)C)=NC=2C(OC)=CC=C1C(N=1)=CSC=1C1=CC=CC=N1 NZBIKEZYGQOFQF-UHFFFAOYSA-N 0.000 claims description 3
- 150000003536 tetrazoles Chemical class 0.000 claims description 3
- LHRIKPIZVNNGRU-UHFFFAOYSA-N 4-(1,4-diazepan-1-yl)-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)-2-methylbenzamide Chemical compound C1=2SC(NC(=O)C=3C(=CC(=CC=3)N3CCNCCC3)C)=NC=2C(OC)=CC=C1C1=CC=CC=C1 LHRIKPIZVNNGRU-UHFFFAOYSA-N 0.000 claims description 2
- DAUHNBJOXXBWQV-UHFFFAOYSA-N 4-(imidazol-1-ylmethyl)-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)benzamide Chemical compound C1=2SC(NC(=O)C=3C=CC(CN4C=NC=C4)=CC=3)=NC=2C(OC)=CC=C1C1=CC=CC=C1 DAUHNBJOXXBWQV-UHFFFAOYSA-N 0.000 claims description 2
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- 238000011176 pooling Methods 0.000 description 1
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- 108020001213 potassium channel Proteins 0.000 description 1
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- 235000011009 potassium phosphates Nutrition 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
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- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
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- 238000000159 protein binding assay Methods 0.000 description 1
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- 108090000623 proteins and genes Proteins 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
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- 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
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- WDPWEXWMQDRXAL-UHFFFAOYSA-N tert-butyl 1,4-diazepane-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCNCC1 WDPWEXWMQDRXAL-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
- NFFJWTUJJBBGBI-UHFFFAOYSA-N tert-butyl n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)carbamate Chemical compound C1=2SC(NC(=O)OC(C)(C)C)=NC=2C(OC)=CC=C1C1=CC=CC=C1 NFFJWTUJJBBGBI-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- KQNRAJPEEFHXHR-UHFFFAOYSA-N trimethyl-(2-methylpyridin-4-yl)stannane Chemical compound CC1=CC([Sn](C)(C)C)=CC=N1 KQNRAJPEEFHXHR-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
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