ES2823180T3 - Compuestos bicíclicos sustituidos con heteroarilo - Google Patents

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Publication number

ES2823180T3

ES2823180T3 ES17742925T ES17742925T ES2823180T3 ES 2823180 T3 ES2823180 T3 ES 2823180T3 ES 17742925 T ES17742925 T ES 17742925T ES 17742925 T ES17742925 T ES 17742925T ES 2823180 T3 ES2823180 T3 ES 2823180T3

Authority

ES

Spain

Prior art keywords

methoxy

methylquinoxalin

oxy

thiazol

fluoro

Prior art date

2016-07-14

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 125000002619 bicyclic group Chemical group 0.000 title description 3
• 125000001072 heteroaryl group Chemical group 0.000 title description 2
• -1 -CHFC (CH3) 3 Chemical group 0.000 claims abstract description 1210
• 150000001875 compounds Chemical class 0.000 claims abstract description 183
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 91
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 77
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 66
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 59
• 150000003839 salts Chemical class 0.000 claims abstract description 58
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 35
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 31
• 239000012453 solvate Substances 0.000 claims abstract description 29
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 28
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 23
• 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 20
• 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 17
• 125000001424 substituent group Chemical group 0.000 claims abstract description 16
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 15
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 12
• 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 11
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
• 125000006393 methylpyrimidinyl group Chemical group 0.000 claims abstract description 10
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 9
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 9
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims abstract description 6
• 125000001041 indolyl group Chemical group 0.000 claims abstract description 6
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 5
• 125000001786 isothiazolyl group Chemical group 0.000 claims abstract description 5
• 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract description 5
• 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 5
• 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 5
• 125000001113 thiadiazolyl group Chemical group 0.000 claims abstract description 5
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 5
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims abstract description 4
• 125000002541 furyl group Chemical group 0.000 claims abstract description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 3
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract 8
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 4
• 235000019256 formaldehyde Nutrition 0.000 claims abstract 3
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract 2
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims abstract 2
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 2
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 461
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 236
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 179
• 238000000034 method Methods 0.000 claims description 135
• 125000005605 benzo group Chemical group 0.000 claims description 89
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 44
• 208000035475 disorder Diseases 0.000 claims description 43
• 230000009424 thromboembolic effect Effects 0.000 claims description 38
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 36
• LCWOVPKDGRAZIW-UHFFFAOYSA-N (2-methylpyrimidin-5-yl) carbamate Chemical compound CC1=NC=C(OC(N)=O)C=N1 LCWOVPKDGRAZIW-UHFFFAOYSA-N 0.000 claims description 33
• RTLYCOOENXHEGT-UHFFFAOYSA-N [2-(2-hydroxyethoxy)pyrimidin-5-yl] carbamate Chemical compound C(N)(OC=1C=NC(=NC=1)OCCO)=O RTLYCOOENXHEGT-UHFFFAOYSA-N 0.000 claims description 22
• 208000007536 Thrombosis Diseases 0.000 claims description 21
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 18
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 17
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 16
• 210000004369 blood Anatomy 0.000 claims description 15
• 239000008280 blood Substances 0.000 claims description 15
• GNIZXLMMVASJLJ-RXMQYKEDSA-N C[C@H](COC1=NC=C(C=N1)OC(=O)N)O Chemical compound C[C@H](COC1=NC=C(C=N1)OC(=O)N)O GNIZXLMMVASJLJ-RXMQYKEDSA-N 0.000 claims description 14
• 206010047249 Venous thrombosis Diseases 0.000 claims description 14
• VZUDLUHFNNHDPL-UHFFFAOYSA-N 2-(difluoromethoxy)-5-(5-methoxy-1-benzofuran-2-yl)-7-methylquinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1OC2=C(C=1)C=C(C=C2)OC)C)F VZUDLUHFNNHDPL-UHFFFAOYSA-N 0.000 claims description 13
• YMPSVHWJOSXVPF-UHFFFAOYSA-N C1=C(C=NC(=N1)CO)OC(=O)N Chemical compound C1=C(C=NC(=N1)CO)OC(=O)N YMPSVHWJOSXVPF-UHFFFAOYSA-N 0.000 claims description 13
• PJOHNOKNXIXPRS-UHFFFAOYSA-N C1=CC(=NC=C1OC(=O)N)CCO Chemical compound C1=CC(=NC=C1OC(=O)N)CCO PJOHNOKNXIXPRS-UHFFFAOYSA-N 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 11
• 201000001320 Atherosclerosis Diseases 0.000 claims description 11
• COELPOHKYHPEIG-UHFFFAOYSA-N C1=C(C=NC(=N1)CCO)OC(=O)N Chemical compound C1=C(C=NC(=N1)CCO)OC(=O)N COELPOHKYHPEIG-UHFFFAOYSA-N 0.000 claims description 11
• GACBMGWBJLNWDG-UHFFFAOYSA-N C1=CC2=C(C=C1OC(=O)N)OC(=O)N2 Chemical compound C1=CC2=C(C=C1OC(=O)N)OC(=O)N2 GACBMGWBJLNWDG-UHFFFAOYSA-N 0.000 claims description 11
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
• 208000006011 Stroke Diseases 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 11
• KNNWVLSYORLMPB-UHFFFAOYSA-N C1=CN=C(C=C1OC(=O)N)OCCO Chemical compound C1=CN=C(C=C1OC(=O)N)OCCO KNNWVLSYORLMPB-UHFFFAOYSA-N 0.000 claims description 10
• XMAXLKXNGADYEX-UHFFFAOYSA-N CC(C)(C1=NC=C(C=C1)OC(=O)N)O Chemical compound CC(C)(C1=NC=C(C=C1)OC(=O)N)O XMAXLKXNGADYEX-UHFFFAOYSA-N 0.000 claims description 10
• DKTZBMXOKZKJFQ-LURJTMIESA-N C[C@@H](CNC(=O)C1=NC=C(C=C1)OC(=O)N)O Chemical compound C[C@@H](CNC(=O)C1=NC=C(C=C1)OC(=O)N)O DKTZBMXOKZKJFQ-LURJTMIESA-N 0.000 claims description 10
• 229920006358 Fluon Polymers 0.000 claims description 10
• GNIZXLMMVASJLJ-YFKPBYRVSA-N [2-[(2S)-2-hydroxypropoxy]pyrimidin-5-yl] carbamate Chemical compound C(N)(OC=1C=NC(=NC=1)OC[C@H](C)O)=O GNIZXLMMVASJLJ-YFKPBYRVSA-N 0.000 claims description 10
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 10
• 238000011282 treatment Methods 0.000 claims description 10
• 206010003658 Atrial Fibrillation Diseases 0.000 claims description 9
• SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 claims description 9
• RBDFFVABHQYUOR-UHFFFAOYSA-N C1=CC(=NC=C1OC(=O)N)OCC(CO)(F)F Chemical compound C1=CC(=NC=C1OC(=O)N)OCC(CO)(F)F RBDFFVABHQYUOR-UHFFFAOYSA-N 0.000 claims description 8
• WKMRXIZBNPLDCC-UHFFFAOYSA-N C1=CN=C(C=C1OC(=O)N)CCO Chemical compound C1=CN=C(C=C1OC(=O)N)CCO WKMRXIZBNPLDCC-UHFFFAOYSA-N 0.000 claims description 8
• GYZGQHZXJSFHPN-UHFFFAOYSA-N CC(C)(CNC(=O)C1=NC=C(C=C1)OC(=O)N)O Chemical compound CC(C)(CNC(=O)C1=NC=C(C=C1)OC(=O)N)O GYZGQHZXJSFHPN-UHFFFAOYSA-N 0.000 claims description 8
• LXEXAZVRZKMFRC-YFKPBYRVSA-N C[C@@H](CO)OC1=NC=C(C=N1)OC(=O)N Chemical compound C[C@@H](CO)OC1=NC=C(C=N1)OC(=O)N LXEXAZVRZKMFRC-YFKPBYRVSA-N 0.000 claims description 8
• LXEXAZVRZKMFRC-RXMQYKEDSA-N C[C@H](CO)OC1=NC=C(C=N1)OC(=O)N Chemical compound C[C@H](CO)OC1=NC=C(C=N1)OC(=O)N LXEXAZVRZKMFRC-RXMQYKEDSA-N 0.000 claims description 8
• JXUGUEVVOLXOBB-UHFFFAOYSA-N [6-(hydroxymethyl)pyridin-3-yl] carbamate Chemical compound C(N)(OC=1C=NC(=CC=1)CO)=O JXUGUEVVOLXOBB-UHFFFAOYSA-N 0.000 claims description 8
• 239000007943 implant Substances 0.000 claims description 8
• LOGAFLFGWNBIIG-UHFFFAOYSA-N pyridin-3-ylcarbamic acid Chemical compound OC(=O)NC1=CC=CN=C1 LOGAFLFGWNBIIG-UHFFFAOYSA-N 0.000 claims description 8
• IROCPMLJWPOPMS-UHFFFAOYSA-N C1=CC(=NC=C1OC(=O)N)OCCO Chemical compound C1=CC(=NC=C1OC(=O)N)OCCO IROCPMLJWPOPMS-UHFFFAOYSA-N 0.000 claims description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
• CXHPQVVLUDCPBU-UHFFFAOYSA-N 1-[6-methoxy-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-4-yl]-2,2-dimethylpropan-1-ol Chemical compound COCC1=NC2=CC(C)=CC(C3=NC4=C(C=C(OC)C=C4S3)C(O)C(C)(C)C)=C2N=C1 CXHPQVVLUDCPBU-UHFFFAOYSA-N 0.000 claims description 6
• KRYHAUGWRXUQOS-UHFFFAOYSA-N 2,2,2-trifluoro-1-[6-methoxy-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-benzothiazol-4-yl]ethanol Chemical compound FC(C(O)C1=CC(=CC2=C1N=C(S2)C1=C2N=CC(=NC2=CC(=C1)C)OC)OC)(F)F KRYHAUGWRXUQOS-UHFFFAOYSA-N 0.000 claims description 6
• MJLLJHYSFSLEFU-UHFFFAOYSA-N 2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-[1,3]thiazolo[5,4-b]pyridine Chemical compound COCC1=NC2=CC(=CC(=C2N=C1)C=1SC2=NC=CC=C2N=1)C MJLLJHYSFSLEFU-UHFFFAOYSA-N 0.000 claims description 6
• KJZARQVQYKUZKS-UHFFFAOYSA-N 2-[7-chloro-2-(methoxymethyl)quinoxalin-5-yl]-6-methoxy-1,3-benzothiazole Chemical compound ClC1=CC(=C2N=CC(=NC2=C1)COC)C=1SC2=C(N=1)C=CC(=C2)OC KJZARQVQYKUZKS-UHFFFAOYSA-N 0.000 claims description 6
• SNCWQSZTWKYWCN-UHFFFAOYSA-N 6-methoxy-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-1,3-benzothiazole Chemical compound COC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)OC)C(=C1)C SNCWQSZTWKYWCN-UHFFFAOYSA-N 0.000 claims description 6
• IYHIVPRFSQFPGP-UHFFFAOYSA-N C1=C(C=NC(=N1)C(=O)NCCO)OC(=O)N Chemical compound C1=C(C=NC(=N1)C(=O)NCCO)OC(=O)N IYHIVPRFSQFPGP-UHFFFAOYSA-N 0.000 claims description 6
• PXXBHADULQHZBJ-ZETCQYMHSA-N C1CN(C[C@H]1O)C(=O)C2=NC=C(C=C2)OC(=O)N Chemical compound C1CN(C[C@H]1O)C(=O)C2=NC=C(C=C2)OC(=O)N PXXBHADULQHZBJ-ZETCQYMHSA-N 0.000 claims description 6
• BMENTPYSRIATSM-UHFFFAOYSA-N CC(C)(CC1=NC=C(C=C1)OC(=O)N)O Chemical compound CC(C)(CC1=NC=C(C=C1)OC(=O)N)O BMENTPYSRIATSM-UHFFFAOYSA-N 0.000 claims description 6
• OQNGAFGMXAXQGN-UHFFFAOYSA-N CC(C)(CCOC1=NC=C(C=N1)OC(=O)N)O Chemical compound CC(C)(CCOC1=NC=C(C=N1)OC(=O)N)O OQNGAFGMXAXQGN-UHFFFAOYSA-N 0.000 claims description 6
• JGOSSFAZNDPMOV-UHFFFAOYSA-N CC(C)(CCOC1=NC=CC(=C1)OC(=O)N)O Chemical compound CC(C)(CCOC1=NC=CC(=C1)OC(=O)N)O JGOSSFAZNDPMOV-UHFFFAOYSA-N 0.000 claims description 6
• CAMWOUPSKSFZKR-UHFFFAOYSA-N CNC(=O)C1=NC=CC(=C1)OC(=O)N Chemical compound CNC(=O)C1=NC=CC(=C1)OC(=O)N CAMWOUPSKSFZKR-UHFFFAOYSA-N 0.000 claims description 6
• IZDNQDSCNDIFGS-UHFFFAOYSA-N COCC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C(=CC(=C2)O)C)C Chemical compound COCC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C(=CC(=C2)O)C)C IZDNQDSCNDIFGS-UHFFFAOYSA-N 0.000 claims description 6
• DKTZBMXOKZKJFQ-ZCFIWIBFSA-N C[C@H](CNC(=O)C1=NC=C(C=C1)OC(=O)N)O Chemical compound C[C@H](CNC(=O)C1=NC=C(C=C1)OC(=O)N)O DKTZBMXOKZKJFQ-ZCFIWIBFSA-N 0.000 claims description 6
• 206010051055 Deep vein thrombosis Diseases 0.000 claims description 6
• UUQQHBWPGGEPJN-UHFFFAOYSA-N [2-(hydroxymethyl)pyridin-4-yl] carbamate Chemical compound OCC1=NC=CC(=C1)OC(N)=O UUQQHBWPGGEPJN-UHFFFAOYSA-N 0.000 claims description 6
• WWVWHVBFWYMTPS-UHFFFAOYSA-N [6-methoxy-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-benzothiazol-4-yl]-(oxan-4-yl)methanol Chemical compound COC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)OC)C(=C1)C(O)C1CCOCC1 WWVWHVBFWYMTPS-UHFFFAOYSA-N 0.000 claims description 6
• ATERRYQPFJWLIZ-UHFFFAOYSA-N [6-methoxy-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-4-yl]-phenylmethanol Chemical compound COC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)COC)C(=C1)C(O)C1=CC=CC=C1 ATERRYQPFJWLIZ-UHFFFAOYSA-N 0.000 claims description 6
• JRXRRWFXWZCQQP-UHFFFAOYSA-N [6-methoxy-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-5-methyl-1,3-benzothiazol-4-yl]methanol Chemical compound COC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)COC)C(=C1C)CO JRXRRWFXWZCQQP-UHFFFAOYSA-N 0.000 claims description 6
• HLIJYKKGWDBBDX-UHFFFAOYSA-N propan-2-yl n-pyridin-3-ylcarbamate Chemical compound CC(C)OC(=O)NC1=CC=CN=C1 HLIJYKKGWDBBDX-UHFFFAOYSA-N 0.000 claims description 6
• 229940124597 therapeutic agent Drugs 0.000 claims description 6
• 238000002560 therapeutic procedure Methods 0.000 claims description 6
• TYQRFIDTNPHBPD-UHFFFAOYSA-N (2-methoxypyrimidin-5-yl) carbamate Chemical compound COC1=NC=C(OC(N)=O)C=N1 TYQRFIDTNPHBPD-UHFFFAOYSA-N 0.000 claims description 5
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 5
• 206010002388 Angina unstable Diseases 0.000 claims description 5
• PXXBHADULQHZBJ-SSDOTTSWSA-N C1CN(C[C@@H]1O)C(=O)C2=NC=C(C=C2)OC(=O)N Chemical compound C1CN(C[C@@H]1O)C(=O)C2=NC=C(C=C2)OC(=O)N PXXBHADULQHZBJ-SSDOTTSWSA-N 0.000 claims description 5
• 206010008088 Cerebral artery embolism Diseases 0.000 claims description 5
• 206010008092 Cerebral artery thrombosis Diseases 0.000 claims description 5
• 206010011091 Coronary artery thrombosis Diseases 0.000 claims description 5
• 206010014513 Embolism arterial Diseases 0.000 claims description 5
• 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 5
• 206010037379 Pulmonary embolism and thrombosis Diseases 0.000 claims description 5
• 206010063544 Renal embolism Diseases 0.000 claims description 5
• 208000032109 Transient ischaemic attack Diseases 0.000 claims description 5
• 208000007814 Unstable Angina Diseases 0.000 claims description 5
• 239000002253 acid Substances 0.000 claims description 5
• 208000002528 coronary thrombosis Diseases 0.000 claims description 5
• 230000002526 effect on cardiovascular system Effects 0.000 claims description 5
• 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 5
• 201000010849 intracranial embolism Diseases 0.000 claims description 5
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
• 208000010125 myocardial infarction Diseases 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 201000005060 thrombophlebitis Diseases 0.000 claims description 5
• 201000010875 transient cerebral ischemia Diseases 0.000 claims description 5
• DFYIFGSROHDOHI-UHFFFAOYSA-N (6-methoxypyridin-3-yl) carbamate Chemical compound C(N)(OC=1C=NC(=CC=1)OC)=O DFYIFGSROHDOHI-UHFFFAOYSA-N 0.000 claims description 4
• UHSTVDOASDPYHU-UHFFFAOYSA-N 1-[2-(2-ethoxy-7-methylquinoxalin-5-yl)-6-methoxy-1,3-benzothiazol-4-yl]-2,2-dimethylpropan-1-ol Chemical compound CCOc1cnc2c(cc(C)cc2n1)-c1nc2c(cc(OC)cc2s1)C(O)C(C)(C)C UHSTVDOASDPYHU-UHFFFAOYSA-N 0.000 claims description 4
• RNNSGFHLSBJDSV-UHFFFAOYSA-N 1-[5-methoxy-2-(2-methoxy-7-methylquinoxalin-5-yl)-[1,3]thiazolo[5,4-b]pyridin-7-yl]-2,2-dimethylpropan-1-ol Chemical compound COC1=CC(=C2C(=N1)SC(=N2)C1=C2N=CC(=NC2=CC(=C1)C)OC)C(C(C)(C)C)O RNNSGFHLSBJDSV-UHFFFAOYSA-N 0.000 claims description 4
• XHCQTXIDKNPMMM-UHFFFAOYSA-N 1-[6-methoxy-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-benzothiazol-4-yl]-2,2-dimethylpropan-1-ol Chemical compound COC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)OC)C(=C1)C(C(C)(C)C)O XHCQTXIDKNPMMM-UHFFFAOYSA-N 0.000 claims description 4
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• UQTZDJGIVSCUEZ-UHFFFAOYSA-N N-[2-[[4-chloro-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-6-yl]oxy]ethyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCOC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)COC)C(=C1)Cl UQTZDJGIVSCUEZ-UHFFFAOYSA-N 0.000 claims description 3
• HQMLEVUTJHHDFN-UHFFFAOYSA-N N-[2-[[4-chloro-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-benzothiazol-6-yl]oxy]ethyl]benzenesulfonamide Chemical compound ClC1=C(C(=CC2=C1N=C(S2)C1=C2N=CC(=NC2=CC(=C1)C)OC)OCCNS(=O)(=O)C1=CC=CC=C1)F HQMLEVUTJHHDFN-UHFFFAOYSA-N 0.000 claims description 3
• XSYGGKOYQPWJRI-UHFFFAOYSA-N N-[2-[[4-cyano-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-6-yl]oxy]ethyl]-4-fluorobenzenesulfonamide Chemical compound COCc1cnc2c(cc(C)cc2n1)-c1nc2c(cc(OCCNS(=O)(=O)c3ccc(F)cc3)cc2s1)C#N XSYGGKOYQPWJRI-UHFFFAOYSA-N 0.000 claims description 3
• IAMRVLGUGHVGNH-UHFFFAOYSA-N N-[[2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-7-yl]methyl]benzenesulfonamide Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC=C2CNS(=O)(=O)C1=CC=CC=C1)C)F IAMRVLGUGHVGNH-UHFFFAOYSA-N 0.000 claims description 3
• SOZOESGACJISOJ-UHFFFAOYSA-N NC(OC(C=N1)=CC=C1F)=O Chemical compound NC(OC(C=N1)=CC=C1F)=O SOZOESGACJISOJ-UHFFFAOYSA-N 0.000 claims description 3
• WOIAGWGOFAKNSX-UHFFFAOYSA-N [1-(hydroxymethyl)cyclobutyl]-[6-methoxy-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-benzothiazol-4-yl]methanol Chemical compound OCC1(CCC1)C(O)C1=CC(=CC2=C1N=C(S2)C1=C2N=CC(=NC2=CC(=C1)C)OC)OC WOIAGWGOFAKNSX-UHFFFAOYSA-N 0.000 claims description 3
• LPDVWWLDLORJFT-UHFFFAOYSA-N [2-(6-chloro-3-methoxyquinolin-8-yl)-6-methoxy-1,3-benzothiazol-4-yl]-[1-(trifluoromethyl)cyclobutyl]methanol Chemical compound ClC=1C=C2C=C(C=NC2=C(C=1)C=1SC2=C(N=1)C(=CC(=C2)OC)C(O)C1(CCC1)C(F)(F)F)OC LPDVWWLDLORJFT-UHFFFAOYSA-N 0.000 claims description 3
• OCWMCGIWAPTAJB-UHFFFAOYSA-N [2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-7-yl] carbamate Chemical compound C(N)(OC1=CC=CC=2N=C(SC=21)C1=C2N=CC(=NC2=CC(=C1)C)OC(F)F)=O OCWMCGIWAPTAJB-UHFFFAOYSA-N 0.000 claims description 3
• URWGXUISDITIRF-UHFFFAOYSA-N [2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-7-yl]methanol Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC=C2CO)C)F URWGXUISDITIRF-UHFFFAOYSA-N 0.000 claims description 3
• QACDFZALQPTSND-UHFFFAOYSA-N [3-methoxy-8-(5-methoxy-7-methyl-[1,3]thiazolo[5,4-b]pyridin-2-yl)quinoxalin-6-yl]methanol Chemical compound COC=1C=NC2=C(C=C(C=C2N=1)CO)C=1SC2=NC(=CC(=C2N=1)C)OC QACDFZALQPTSND-UHFFFAOYSA-N 0.000 claims description 3
• ARUBCJJYOAPSFG-UHFFFAOYSA-N [3-methoxy-8-(6-methoxy-4,5-dimethyl-1,3-benzothiazol-2-yl)quinoxalin-6-yl]methanol Chemical compound COC=1C=NC2=C(C=C(C=C2N=1)CO)C=1SC2=C(N=1)C(=C(C(=C2)OC)C)C ARUBCJJYOAPSFG-UHFFFAOYSA-N 0.000 claims description 3
• ANDDXAHZMWSUES-UHFFFAOYSA-N [5-methoxy-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-[1,3]thiazolo[5,4-b]pyridin-7-yl]methanol Chemical compound COC1=CC(=C2C(=N1)SC(=N2)C1=C2N=CC(=NC2=CC(=C1)C)COC)CO ANDDXAHZMWSUES-UHFFFAOYSA-N 0.000 claims description 3
• XBHSWPYANMBACV-UHFFFAOYSA-N [6-methoxy-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-benzothiazol-4-yl]-(1,3-thiazol-2-yl)methanol Chemical compound COC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)OC)C(=C1)C(O)C=1SC=CN=1 XBHSWPYANMBACV-UHFFFAOYSA-N 0.000 claims description 3
• JBSDKNNGGPALHS-UHFFFAOYSA-N [6-methoxy-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-benzothiazol-4-yl]-(1-phenylcyclobutyl)methanol Chemical compound COC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)OC)C(=C1)C(O)C1(CCC1)C1=CC=CC=C1 JBSDKNNGGPALHS-UHFFFAOYSA-N 0.000 claims description 3
• FDUCXURCQXIIBP-UHFFFAOYSA-N [6-methoxy-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-benzothiazol-4-yl]-(2-propan-2-ylphenyl)methanol Chemical compound C(C)(C)C1=C(C=CC=C1)C(O)C1=CC(=CC2=C1N=C(S2)C1=C2N=CC(=NC2=CC(=C1)C)OC)OC FDUCXURCQXIIBP-UHFFFAOYSA-N 0.000 claims description 3
• BLCZGRMGPKKXJH-UHFFFAOYSA-N [6-methoxy-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-benzothiazol-4-yl]-[3-(trifluoromethyl)phenyl]methanol Chemical compound COC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)OC)C(=C1)C(O)C1=CC(=CC=C1)C(F)(F)F BLCZGRMGPKKXJH-UHFFFAOYSA-N 0.000 claims description 3
• MLQKBXPGHMMEBJ-UHFFFAOYSA-N [6-methoxy-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-benzothiazol-4-yl]-phenylmethanol Chemical compound COc1cc(C(O)c2ccccc2)c2nc(sc2c1)-c1cc(C)cc2nc(OC)cnc12 MLQKBXPGHMMEBJ-UHFFFAOYSA-N 0.000 claims description 3
• FNOFEMOUHIYJBR-UHFFFAOYSA-N [6-methoxy-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-benzothiazol-4-yl]methanol Chemical compound COC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)OC)C(=C1)CO FNOFEMOUHIYJBR-UHFFFAOYSA-N 0.000 claims description 3
• KJAZEUYGOIFECV-UHFFFAOYSA-N [6-methoxy-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-4-yl]-pyridin-2-ylmethanol Chemical compound COC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)COC)C(=C1)C(O)C1=NC=CC=C1 KJAZEUYGOIFECV-UHFFFAOYSA-N 0.000 claims description 3
• PQZXJLWEHVPZOO-UHFFFAOYSA-N [6-methoxy-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-4-yl]-pyridin-3-ylmethanol Chemical compound COC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)COC)C(=C1)C(O)C=1C=NC=CC=1 PQZXJLWEHVPZOO-UHFFFAOYSA-N 0.000 claims description 3
• JSXUJQYMNCWCMS-UHFFFAOYSA-N [6-methoxy-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-4-yl]methanol Chemical compound COC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)COC)C(=C1)CO JSXUJQYMNCWCMS-UHFFFAOYSA-N 0.000 claims description 3
• MNEPLPVWSMZAOG-UHFFFAOYSA-N [6-methoxy-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-5-yl]methanol Chemical compound COC1=CC2=C(N=C(S2)C2=C3N=CC(=NC3=CC(=C2)C)COC)C=C1CO MNEPLPVWSMZAOG-UHFFFAOYSA-N 0.000 claims description 3
• BFBWDUQLNDORJH-UHFFFAOYSA-N [8-(4-chloro-5-fluoro-6-methoxy-1,3-benzothiazol-2-yl)-3-methoxyquinoxalin-6-yl]methanol Chemical compound ClC1=C(C(=CC2=C1N=C(S2)C=1C=C(C=C2N=C(C=NC=12)OC)CO)OC)F BFBWDUQLNDORJH-UHFFFAOYSA-N 0.000 claims description 3
• BTFQOOOZKAYMBP-UHFFFAOYSA-N [8-(5-fluoro-6-methoxy-4-methyl-1,3-benzothiazol-2-yl)-3-methoxyquinoxalin-6-yl]methanol Chemical compound FC=1C(=CC2=C(N=C(S2)C=2C=C(C=C3N=C(C=NC=23)OC)CO)C=1C)OC BTFQOOOZKAYMBP-UHFFFAOYSA-N 0.000 claims description 3
• GXDWVVHGPQCTQS-UHFFFAOYSA-N [8-(6-fluoro-5-methoxy-1-benzofuran-2-yl)-3-methoxyquinoxalin-6-yl]methanol Chemical compound FC1=CC2=C(C=C(O2)C=2C=C(C=C3N=C(C=NC=23)OC)CO)C=C1OC GXDWVVHGPQCTQS-UHFFFAOYSA-N 0.000 claims description 3
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
• JBVJEOKIVVCQNP-UHFFFAOYSA-N butan-2-yl n-pyridin-3-ylcarbamate Chemical compound CCC(C)OC(=O)NC1=CC=CN=C1 JBVJEOKIVVCQNP-UHFFFAOYSA-N 0.000 claims description 3
• VXJUDXCDWVRBGI-UHFFFAOYSA-N cyclobutyl-[6-methoxy-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-4-yl]methanol Chemical compound C1(CCC1)C(O)C1=CC(=CC2=C1N=C(S2)C1=C2N=CC(=NC2=CC(=C1)C)COC)OC VXJUDXCDWVRBGI-UHFFFAOYSA-N 0.000 claims description 3
• LCGDNOWZLAWRQH-UHFFFAOYSA-N cyclohexyl-[6-methoxy-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-4-yl]methanol Chemical compound C1(CCCCC1)C(O)C1=CC(=CC2=C1N=C(S2)C1=C2N=CC(=NC2=CC(=C1)C)COC)OC LCGDNOWZLAWRQH-UHFFFAOYSA-N 0.000 claims description 3
• NHOCEBHBALZKNU-UHFFFAOYSA-N cyclopropyl-[6-methoxy-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-1,3-benzothiazol-4-yl]methanol Chemical compound COCc1cnc2c(cc(C)cc2n1)-c1nc2c(cc(OC)cc2s1)C(O)C1CC1 NHOCEBHBALZKNU-UHFFFAOYSA-N 0.000 claims description 3
• QCQAFAYKGTVDLH-UHFFFAOYSA-N cyclopropyl-[8-(5-fluoro-6-methoxy-4-methyl-1,3-benzothiazol-2-yl)-3-methoxyquinoxalin-6-yl]methanol Chemical compound C1(CC1)C(O)C=1C=C2N=C(C=NC2=C(C=1)C=1SC2=C(N=1)C(=C(C(=C2)OC)F)C)OC QCQAFAYKGTVDLH-UHFFFAOYSA-N 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• APHVGKYWHWFAQV-UHFFFAOYSA-N methyl 1-methylpyrrole-2-carboxylate Chemical compound COC(=O)C1=CC=CN1C APHVGKYWHWFAQV-UHFFFAOYSA-N 0.000 claims description 3
• GSIFCBFUEHODIM-UHFFFAOYSA-N methyl 2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-4-methyl-1,3-benzothiazole-6-carboxylate Chemical compound COCC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C(=CC(=C2)C(=O)OC)C)C GSIFCBFUEHODIM-UHFFFAOYSA-N 0.000 claims description 3
• ACGXMOTYRRTPPY-UHFFFAOYSA-N methyl 5-(1-benzofuran-2-yl)-7-methylquinoxaline-2-carboxylate Chemical compound O1C(=CC2=C1C=CC=C2)C1=C2N=CC(=NC2=CC(=C1)C)C(=O)OC ACGXMOTYRRTPPY-UHFFFAOYSA-N 0.000 claims description 3
• WNOGCTACLTZJDU-UHFFFAOYSA-N methyl 5-[6-[2-[(4-fluorophenyl)sulfonylamino]ethoxy]-4-methyl-1,3-benzothiazol-2-yl]-7-methylquinoxaline-2-carboxylate Chemical compound COC(=O)c1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc(OCCNS(=O)(=O)c3ccc(F)cc3)cc2s1 WNOGCTACLTZJDU-UHFFFAOYSA-N 0.000 claims description 3
• IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 3
• 238000011324 primary prophylaxis Methods 0.000 claims description 3
• GGLROGDZOZKZGW-UHFFFAOYSA-N propan-2-yl N-pyridazin-4-ylcarbamate Chemical compound N1=NC=C(C=C1)NC(OC(C)C)=O GGLROGDZOZKZGW-UHFFFAOYSA-N 0.000 claims description 3
• RZMOVEMVGHXIBW-UHFFFAOYSA-N propan-2-yl n-pyridin-4-ylcarbamate Chemical compound CC(C)OC(=O)NC1=CC=NC=C1 RZMOVEMVGHXIBW-UHFFFAOYSA-N 0.000 claims description 3
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 3
• JIOOILNNLPXUQT-UHFFFAOYSA-N (5-methyl-1,3,4-oxadiazol-2-yl) carbamate Chemical compound CC1=NN=C(OC(N)=O)O1 JIOOILNNLPXUQT-UHFFFAOYSA-N 0.000 claims description 2
• AWSUXLKFJUIGEI-UHFFFAOYSA-N (6-methylpyridin-3-yl) carbamate Chemical compound CC1=CC=C(OC(N)=O)C=N1 AWSUXLKFJUIGEI-UHFFFAOYSA-N 0.000 claims description 2
• WMKAQICNOMCGRO-UHFFFAOYSA-N 1-[6-methoxy-2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-5-methyl-1,3-benzothiazol-4-yl]-2,2-dimethylpropan-1-ol Chemical compound COCc1cnc2c(cc(C)cc2n1)-c1nc2c(C(O)C(C)(C)C)c(C)c(OC)cc2s1 WMKAQICNOMCGRO-UHFFFAOYSA-N 0.000 claims description 2
• KTJLBYAZHVLKDE-UHFFFAOYSA-N 1-[[2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-4,5-dimethyl-1,3-benzothiazol-6-yl]oxy]propan-2-ol Chemical compound COCC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C(=C(C(=C2)OCC(C)O)C)C)C KTJLBYAZHVLKDE-UHFFFAOYSA-N 0.000 claims description 2
• NDRUBTGOJIKPEZ-UHFFFAOYSA-N 1-[[4-chloro-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-benzothiazol-6-yl]oxy]propan-2-yl hydrogen carbonate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)c(F)c(OCC(C)OC(O)=O)cc2s1 NDRUBTGOJIKPEZ-UHFFFAOYSA-N 0.000 claims description 2
• HZVPCXKHAAAPLI-UHFFFAOYSA-N 1h-indol-5-ylcarbamic acid Chemical compound OC(=O)NC1=CC=C2NC=CC2=C1 HZVPCXKHAAAPLI-UHFFFAOYSA-N 0.000 claims description 2
• PBOAGYSGWIHKHA-UHFFFAOYSA-N 2,2,2-trifluoroethyl carbamate Chemical compound NC(=O)OCC(F)(F)F PBOAGYSGWIHKHA-UHFFFAOYSA-N 0.000 claims description 2
• ZPSFCQGDDJCFPE-UHFFFAOYSA-N 2-(2-methoxy-7-methylquinoxalin-5-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[d][1,3]thiazole Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)CCCCC2)C ZPSFCQGDDJCFPE-UHFFFAOYSA-N 0.000 claims description 2
• BEWWHFBQCSRYDI-UHFFFAOYSA-N 2-(difluoromethoxy)-5-(1H-indol-2-yl)-7-methylquinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1NC2=CC=CC=C2C=1)C)F BEWWHFBQCSRYDI-UHFFFAOYSA-N 0.000 claims description 2
• KDMZGYHROLTSCH-UHFFFAOYSA-N 2-(difluoromethoxy)-5-imidazo[1,2-a]pyridin-2-yl-7-methylquinoxaline Chemical compound CC1=CC(C2=CN3C=CC=CC3=N2)=C2N=CC(OC(F)F)=NC2=C1 KDMZGYHROLTSCH-UHFFFAOYSA-N 0.000 claims description 2
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• KDJPYAWCMNKXMV-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-4,5,6,7-tetrahydro-1,3-benzothiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)CCCC2)C)F KDJPYAWCMNKXMV-UHFFFAOYSA-N 0.000 claims description 2
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