ES2823180T3 - Compuestos bicíclicos sustituidos con heteroarilo - Google Patents
Compuestos bicíclicos sustituidos con heteroarilo Download PDFInfo
- 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
- 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.)
- Active
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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
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- 229940124597 therapeutic agent Drugs 0.000 claims description 6
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- 230000002526 effect on cardiovascular system Effects 0.000 claims description 5
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
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- 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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- 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
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- 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
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- 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
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- 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
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- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000021331 vascular occlusion disease Diseases 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 108010047303 von Willebrand Factor Proteins 0.000 description 1
- 102100036537 von Willebrand factor Human genes 0.000 description 1
- 229960001134 von willebrand factor Drugs 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662362113P | 2016-07-14 | 2016-07-14 | |
| PCT/US2017/041878 WO2018013774A1 (en) | 2016-07-14 | 2017-07-13 | Bicyclic heteroaryl substituted compounds |
Publications (1)
| Publication Number | Publication Date |
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| ES2823180T3 true ES2823180T3 (es) | 2021-05-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES17742925T Active ES2823180T3 (es) | 2016-07-14 | 2017-07-13 | Compuestos bicíclicos sustituidos con heteroarilo |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US20190292176A1 (enExample) |
| EP (1) | EP3484878B1 (enExample) |
| JP (1) | JP7058256B2 (enExample) |
| KR (1) | KR102460385B1 (enExample) |
| CN (1) | CN109689647B (enExample) |
| ES (1) | ES2823180T3 (enExample) |
| WO (1) | WO2018013774A1 (enExample) |
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| CN109689642B (zh) * | 2016-07-14 | 2022-04-12 | 百时美施贵宝公司 | 经单环杂芳基取代的化合物 |
| US10730868B2 (en) | 2016-07-14 | 2020-08-04 | Bristol-Myers Squibb Company | Bicyclic heteroaryl substituted compounds |
| EP3484894B1 (en) * | 2016-07-14 | 2020-08-19 | Bristol-Myers Squibb Company | Tricyclic heteroaryl-substituted quinoline and azaquinoline compounds as par4 inhibitors |
| CN109836360B (zh) * | 2019-03-19 | 2021-08-13 | 南京恩泰医药科技有限公司 | 一种甲苯磺酸依度沙班中间体的制备方法及中间体化合物 |
| CN113024475B (zh) * | 2019-12-25 | 2022-08-09 | 宁夏大学 | 一种喹喔啉酮类化合物的合成方法 |
| CN111440146B (zh) * | 2020-05-15 | 2022-10-21 | 中国药科大学 | 一种具有par4拮抗活性的苯并三嗪类化合物及其应用 |
| JP7753950B2 (ja) * | 2022-03-30 | 2025-10-15 | 三菱ケミカル株式会社 | 環状亜硫酸エステルの製造方法 |
| EP4561983B1 (en) | 2022-07-28 | 2026-07-08 | Bayer Aktiengesellschaft | Process for preparation of 2-chloro-3-fluoro-4-alkoxy-anilines and 2-fluoro-3-chlorophenol |
| CN118164924A (zh) * | 2022-12-11 | 2024-06-11 | 沈阳中化农药化工研发有限公司 | 一种酰胺类化合物及其应用 |
| WO2024131948A1 (zh) * | 2022-12-22 | 2024-06-27 | 人福医药集团股份公司 | 制备p2x3抑制剂的方法 |
| CN115925588A (zh) * | 2022-12-26 | 2023-04-07 | 诚达药业股份有限公司 | 一种脂肪族亚磺酸钠盐的制备方法 |
| AR131541A1 (es) | 2023-01-07 | 2025-04-09 | Syngenta Crop Protection Ag | Compuestos de carboxamida novedosos |
| WO2025032129A1 (en) | 2023-08-08 | 2025-02-13 | Syngenta Crop Protection Ag | Novel aminoindane and aminotetraline compounds |
| US11976055B1 (en) | 2023-08-24 | 2024-05-07 | King Faisal University | 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-3-ol as an antitumor and antimicrobial compound |
| US11986461B1 (en) | 2023-08-24 | 2024-05-21 | King Faisal University | 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol as an antitumor and antimicrobial compound |
| US11964959B1 (en) | 2023-09-05 | 2024-04-23 | King Faisal University | 3-(4,5-Diphenyl-2-(pyridin-3-yl)-1H-imidazol-1-yl)-N,N-dimethylpopan-1-amine as an antimicrobial compound |
| WO2025109114A1 (en) | 2023-11-24 | 2025-05-30 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| US11952361B1 (en) | 2023-12-26 | 2024-04-09 | King Faisal University | 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl) pyridin-3-ol as an antitumor and antimicrobial compound |
| WO2025149637A1 (en) | 2024-01-12 | 2025-07-17 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| PY2501648A (es) | 2024-01-12 | 2025-10-31 | Syngenta Crop Protection Ag | Nuevos compuestos de carboxamida |
| WO2026008750A1 (en) | 2024-07-05 | 2026-01-08 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
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| CA1164459A (en) * | 1980-11-11 | 1984-03-27 | Yung-Hsiung Yang | Process for preparing (imidazo¬1,2-a|pyridine- 2-yl)-carbostyril or -3,4-dihydrocarbostyryl derivatives |
| YU136287A (en) * | 1986-07-25 | 1990-06-30 | Boehringer Kg | Process for preparing new 1,4 benzodiazepines |
| TW279162B (enExample) * | 1991-09-26 | 1996-06-21 | Mitsubishi Chem Corp | |
| JP2928079B2 (ja) | 1994-02-14 | 1999-07-28 | 永信薬品工業股▲ふん▼有限公司 | １−（置換ベンジル）−３−（置換アリール）縮合ピラゾール類、その製造法及びその用途 |
| US6166041A (en) | 1995-10-11 | 2000-12-26 | Euro-Celtique, S.A. | 2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma |
| DE69723863T2 (de) * | 1996-11-06 | 2004-04-15 | Darwin Discovery Ltd., Slough | Chinoline und deren therapeutische verwendung |
| US6313126B1 (en) * | 1999-01-07 | 2001-11-06 | American Home Products Corp | Arylpiperazinyl-cyclohexyl indole derivatives for the treatment of depression |
| US6387942B2 (en) | 2000-06-19 | 2002-05-14 | Yung Shin Pharmaceutical Ind. Co. Ltd | Method of treating disorders related to protease-activated receptors-induced cell activation |
| EP1348701A1 (en) | 2002-03-28 | 2003-10-01 | Warner-Lambert Company LLC | (2,4-disubstituted-thiazol-5-yl) amine compounds as PDE7 inhibitors |
| BRPI0413234A (pt) | 2003-08-01 | 2006-10-03 | Genelabs Tech Inc | derivados de imidazola bicìclica contra flaviviridae |
| US20050272784A1 (en) | 2004-05-07 | 2005-12-08 | Xiaobing Li | Inhibitors of bacterial Type III protein secretion systems |
| RU2007107177A (ru) | 2004-07-28 | 2008-09-10 | Айрм Ллк (Bm) | Соединения и композиции, как модуляторы ядерных рецепторов стероидных гормонов |
| CN101103026A (zh) | 2005-01-14 | 2008-01-09 | 健亚生物科技公司 | 用于治疗病毒感染的吲哚衍生物 |
| US20080015193A1 (en) | 2006-06-20 | 2008-01-17 | Mendoza Jose S | Certain azoles exhibiting ATP-utilizing enzyme inhibitory activity, compositions, and uses thereof |
| BRPI0713946A2 (pt) | 2006-06-29 | 2012-12-04 | Hoffmann La Roche | compostos, composições farmacêuticas que os compreendem, método para o tratamento terapêutico e/ou profilático de enfermidades que são moduladas por agonistas de fxr, e uso dos compostos |
| WO2008073451A2 (en) | 2006-12-11 | 2008-06-19 | Sirtris Pharmaceuticals, Inc. | Benzoimidazole derivatives as sirtuin (sir) modulating compounds |
| WO2009073497A2 (en) | 2007-11-30 | 2009-06-11 | Smithkline Beecham Corporation | Prolyl hydroxylase inhibitors |
| AU2009243006B2 (en) | 2008-05-01 | 2013-03-21 | Sirtris Pharmaceuticals, Inc. | Quinolines and related analogs as sirtuin modulators |
| AU2009248774B2 (en) | 2008-05-23 | 2012-05-31 | Novartis Ag | Derivatives of quinolines and quinoxalines as protein tyrosine kinase inhibitors |
| MX2011000837A (es) | 2008-07-23 | 2011-04-05 | Vertex Pharma | Inhibidores de pirazolpiridina cinasa triciclica. |
| EP2348018A4 (en) | 2008-09-25 | 2012-04-25 | Kyorin Seiyaku Kk | HETEROCYCLIC BIARYL DERIVATIVE AND PDE INHIBITOR CONTAINING ACTIVE SUBSTANCE |
| WO2012154888A1 (en) | 2011-05-09 | 2012-11-15 | Proteostasis Therapeutics, Inc. | Compounds for treating protein folding disorders |
| WO2013130660A1 (en) | 2012-02-28 | 2013-09-06 | Amgen Inc. | Amides as pim inhibitors |
| KR20150003766A (ko) | 2012-04-26 | 2015-01-09 | 브리스톨-마이어스 스큅 컴퍼니 | 혈소판 응집을 치료하기 위한 프로테아제 활성화 수용체 4 (par4) 억제제로서의 이미다조티아디아졸 및 이미다조피리다진 유도체 |
| SG11201406759YA (en) | 2012-04-26 | 2014-11-27 | Bristol Myers Squibb Co | Imidazothiadiazole derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation |
| ES2640916T3 (es) * | 2012-04-26 | 2017-11-07 | Bristol-Myers Squibb Company | Derivados de imidazotiadiazol e imidazopirazina como inhibidores del receptor 4 activados por proteasa (PAR4) para tratar agregación plaquetaria |
| US9617279B1 (en) | 2014-06-24 | 2017-04-11 | Bristol-Myers Squibb Company | Imidazooxadiazole compounds |
| US9598419B1 (en) | 2014-06-24 | 2017-03-21 | Universite De Montreal | Imidazotriazine and imidazodiazine compounds |
| US10238638B2 (en) | 2015-02-26 | 2019-03-26 | Universite De Montreal | Benzothiazole and benzothiophene compounds |
| EP3262053B1 (en) | 2015-02-26 | 2022-10-05 | Université de Montréal | Imidazothiadiazole compounds as par4-inhibitors |
| US20180148429A1 (en) | 2015-05-13 | 2018-05-31 | Selvita S.A. | Substituted quinoxaline derivatives |
| EP3328839A1 (en) | 2015-07-30 | 2018-06-06 | Bristol-Myers Squibb Company | Aryl substituted bicyclic heteroaryl compounds |
| EP3484894B1 (en) | 2016-07-14 | 2020-08-19 | Bristol-Myers Squibb Company | Tricyclic heteroaryl-substituted quinoline and azaquinoline compounds as par4 inhibitors |
| CN109689642B (zh) | 2016-07-14 | 2022-04-12 | 百时美施贵宝公司 | 经单环杂芳基取代的化合物 |
| US10730868B2 (en) | 2016-07-14 | 2020-08-04 | Bristol-Myers Squibb Company | Bicyclic heteroaryl substituted compounds |
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2017
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2020
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Also Published As
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| US20190292176A1 (en) | 2019-09-26 |
| JP2019528247A (ja) | 2019-10-10 |
| CN109689647A (zh) | 2019-04-26 |
| WO2018013774A1 (en) | 2018-01-18 |
| JP7058256B2 (ja) | 2022-04-21 |
| US12060347B2 (en) | 2024-08-13 |
| KR20190027385A (ko) | 2019-03-14 |
| EP3484878B1 (en) | 2020-08-19 |
| CN109689647B (zh) | 2023-01-20 |
| EP3484878A1 (en) | 2019-05-22 |
| US20210163465A1 (en) | 2021-06-03 |
| KR102460385B1 (ko) | 2022-10-27 |
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