JP2015517515A5 - - Google Patents
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- JP2015517515A5 JP2015517515A5 JP2015512073A JP2015512073A JP2015517515A5 JP 2015517515 A5 JP2015517515 A5 JP 2015517515A5 JP 2015512073 A JP2015512073 A JP 2015512073A JP 2015512073 A JP2015512073 A JP 2015512073A JP 2015517515 A5 JP2015517515 A5 JP 2015517515A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- dioxin
- carboxylic acid
- benzo
- dicyclohexyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 208000010378 Pulmonary Embolism Diseases 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 208000007536 Thrombosis Diseases 0.000 claims description 5
- 206010000891 acute myocardial infarction Diseases 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- 206010008088 Cerebral artery embolism Diseases 0.000 claims description 4
- 206010008092 Cerebral artery thrombosis Diseases 0.000 claims description 4
- 206010011091 Coronary artery thrombosis Diseases 0.000 claims description 4
- 206010051055 Deep vein thrombosis Diseases 0.000 claims description 4
- 206010014513 Embolism arterial Diseases 0.000 claims description 4
- 206010014522 Embolism venous Diseases 0.000 claims description 4
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 4
- 206010063544 Renal embolism Diseases 0.000 claims description 4
- 201000007023 Thrombotic Thrombocytopenic Purpura Diseases 0.000 claims description 4
- 206010047249 Venous thrombosis Diseases 0.000 claims description 4
- 230000033115 angiogenesis Effects 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 208000002528 coronary thrombosis Diseases 0.000 claims description 4
- 208000009190 disseminated intravascular coagulation Diseases 0.000 claims description 4
- 201000010849 intracranial embolism Diseases 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 208000037803 restenosis Diseases 0.000 claims description 4
- 230000001052 transient effect Effects 0.000 claims description 4
- 208000004043 venous thromboembolism Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 208000004454 Hyperalgesia Diseases 0.000 claims description 3
- 208000035154 Hyperesthesia Diseases 0.000 claims description 3
- 208000032382 Ischaemic stroke Diseases 0.000 claims description 3
- 208000001435 Thromboembolism Diseases 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 230000002490 cerebral effect Effects 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 201000011461 pre-eclampsia Diseases 0.000 claims description 3
- 238000001356 surgical procedure Methods 0.000 claims description 3
- 201000005060 thrombophlebitis Diseases 0.000 claims description 3
- 230000002792 vascular Effects 0.000 claims description 3
- 101001038037 Homo sapiens Lysophosphatidic acid receptor 5 Proteins 0.000 claims description 2
- 206010065390 Inflammatory pain Diseases 0.000 claims description 2
- 210000004351 coronary vessel Anatomy 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 41
- 125000001424 substituent group Chemical group 0.000 claims 26
- 229910052757 nitrogen Inorganic materials 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 15
- 229910052731 fluorine Inorganic materials 0.000 claims 14
- 239000011737 fluorine Substances 0.000 claims 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 13
- 125000005842 heteroatom Chemical group 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 150000001924 cycloalkanes Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 230000009467 reduction Effects 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- KDKJWPODDXVGNR-UHFFFAOYSA-N 6-bromo-4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(Br)C=C2C1(C1CCCCC1)C1CCCCC1 KDKJWPODDXVGNR-UHFFFAOYSA-N 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 238000007887 coronary angioplasty Methods 0.000 claims 2
- 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 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- CGKINPBJKARFLP-UHFFFAOYSA-N 1,1-dicyclohexyl-7,8,9,10-tetrahydrobenzo[f][1,3]benzodioxine-3-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C3CCCCC3=C2C1(C1CCCCC1)C1CCCCC1 CGKINPBJKARFLP-UHFFFAOYSA-N 0.000 claims 1
- LWZJFTCOUTZELF-UHFFFAOYSA-N 1,1-dicyclohexylbenzo[f][1,3]benzodioxine-3-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C3C=CC=CC3=C2C1(C1CCCCC1)C1CCCCC1 LWZJFTCOUTZELF-UHFFFAOYSA-N 0.000 claims 1
- YUCIBCCPUGNTDT-UHFFFAOYSA-N 10-benzyl-4,4-dicyclohexylbenzo[g][1,3]benzodioxine-2-carboxylic acid Chemical compound C12=CC=CC=C2C=C2C(C3CCCCC3)(C3CCCCC3)OC(C(=O)O)OC2=C1CC1=CC=CC=C1 YUCIBCCPUGNTDT-UHFFFAOYSA-N 0.000 claims 1
- WKCGQNXDJFNFQP-UHFFFAOYSA-N 3-(6-chloro-4,4-dicyclohexyl-1,3-benzodioxin-2-yl)-2h-1,2,4-oxadiazol-5-one Chemical compound C12=CC(Cl)=CC=C2OC(C=2NOC(=O)N=2)OC1(C1CCCCC1)C1CCCCC1 WKCGQNXDJFNFQP-UHFFFAOYSA-N 0.000 claims 1
- WAXRDOOISKVDOT-UHFFFAOYSA-N 4,4-di(cycloheptyl)-6-(trifluoromethoxy)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(OC(F)(F)F)C=C2C1(C1CCCCCC1)C1CCCCCC1 WAXRDOOISKVDOT-UHFFFAOYSA-N 0.000 claims 1
- MBUCGUYVKGSEHA-UHFFFAOYSA-N 4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=CC=C2C1(C1CCCCC1)C1CCCCC1 MBUCGUYVKGSEHA-UHFFFAOYSA-N 0.000 claims 1
- JOJGLFXLBYZKGB-UHFFFAOYSA-N 4,4-dicyclohexyl-5,7-difluoro-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC(F)=CC(F)=C2C1(C1CCCCC1)C1CCCCC1 JOJGLFXLBYZKGB-UHFFFAOYSA-N 0.000 claims 1
- YBMFWFCVTOAMTR-UHFFFAOYSA-N 4,4-dicyclohexyl-5,7-dimethoxy-1,3-benzodioxine-2-carboxylic acid Chemical compound C=1C(OC)=CC(OC)=C2C=1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 YBMFWFCVTOAMTR-UHFFFAOYSA-N 0.000 claims 1
- PVUPGOUGVPNXRU-UHFFFAOYSA-N 4,4-dicyclohexyl-5-ethoxy-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=2C(OCC)=CC=CC=2OC(C(O)=O)OC1(C1CCCCC1)C1CCCCC1 PVUPGOUGVPNXRU-UHFFFAOYSA-N 0.000 claims 1
- QDVMDMANAAENOD-UHFFFAOYSA-N 4,4-dicyclohexyl-5-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=2C(C)=CC=CC=2OC(C(O)=O)OC1(C1CCCCC1)C1CCCCC1 QDVMDMANAAENOD-UHFFFAOYSA-N 0.000 claims 1
- LMYZHOYELPVYPT-UHFFFAOYSA-N 4,4-dicyclohexyl-6-(3-methoxyphenoxy)-1,3-benzodioxine-2-carboxylic acid Chemical compound COC1=CC=CC(OC=2C=C3C(C4CCCCC4)(C4CCCCC4)OC(OC3=CC=2)C(O)=O)=C1 LMYZHOYELPVYPT-UHFFFAOYSA-N 0.000 claims 1
- OJZKUQVZXKOGDE-UHFFFAOYSA-N 4,4-dicyclohexyl-6-(trifluoromethoxy)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(OC(F)(F)F)C=C2C1(C1CCCCC1)C1CCCCC1 OJZKUQVZXKOGDE-UHFFFAOYSA-N 0.000 claims 1
- ZOLCCSWVSQMFBG-UHFFFAOYSA-N 4,4-dicyclohexyl-6-(trifluoromethyl)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(C(F)(F)F)C=C2C1(C1CCCCC1)C1CCCCC1 ZOLCCSWVSQMFBG-UHFFFAOYSA-N 0.000 claims 1
- JUGCDSDJNBWLJX-UHFFFAOYSA-N 4,4-dicyclohexyl-6-fluoro-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(F)C=C2C1(C1CCCCC1)C1CCCCC1 JUGCDSDJNBWLJX-UHFFFAOYSA-N 0.000 claims 1
- UNPSUVUWCYRLAV-UHFFFAOYSA-N 4,4-dicyclohexyl-6-iodo-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(I)C=C2C1(C1CCCCC1)C1CCCCC1 UNPSUVUWCYRLAV-UHFFFAOYSA-N 0.000 claims 1
- APFALXFHUMONES-UHFFFAOYSA-N 4,4-dicyclohexyl-6-methoxy-1,3-benzodioxine-2-carboxylic acid Chemical compound C12=CC(OC)=CC=C2OC(C(O)=O)OC1(C1CCCCC1)C1CCCCC1 APFALXFHUMONES-UHFFFAOYSA-N 0.000 claims 1
- DCMVRCLSDLQDJL-UHFFFAOYSA-N 4,4-dicyclohexyl-6-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C12=CC(C)=CC=C2OC(C(O)=O)OC1(C1CCCCC1)C1CCCCC1 DCMVRCLSDLQDJL-UHFFFAOYSA-N 0.000 claims 1
- UYEBYMXVPXATKI-UHFFFAOYSA-N 4,4-dicyclohexyl-6-phenyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(C=3C=CC=CC=3)C=C2C1(C1CCCCC1)C1CCCCC1 UYEBYMXVPXATKI-UHFFFAOYSA-N 0.000 claims 1
- VUGKJOIJENCQHI-UHFFFAOYSA-N 4,4-dicyclohexyl-6-pyridin-3-yloxy-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=C2C(C3CCCCC3)(C3CCCCC3)OC(C(=O)O)OC2=CC=C1OC1=CC=CN=C1 VUGKJOIJENCQHI-UHFFFAOYSA-N 0.000 claims 1
- QAOMCUWIGZSPHK-UHFFFAOYSA-N 4,4-dicyclohexyl-6-pyridin-4-yl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(C=3C=CN=CC=3)C=C2C1(C1CCCCC1)C1CCCCC1 QAOMCUWIGZSPHK-UHFFFAOYSA-N 0.000 claims 1
- PQKIXWFIZHKPGF-UHFFFAOYSA-N 4,4-dicyclohexyl-6-pyrrolidin-1-ylsulfonyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(S(=O)(=O)N3CCCC3)C=C2C1(C1CCCCC1)C1CCCCC1 PQKIXWFIZHKPGF-UHFFFAOYSA-N 0.000 claims 1
- ZTMLYBVFVDTKGY-UHFFFAOYSA-N 4,4-dicyclohexyl-7-(diethylamino)-1,3-benzodioxine-2-carboxylic acid Chemical compound C=1C(N(CC)CC)=CC=C2C=1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 ZTMLYBVFVDTKGY-UHFFFAOYSA-N 0.000 claims 1
- ISFWOCTVLCBYSR-UHFFFAOYSA-N 4,4-dicyclohexyl-7-(dimethylamino)-1,3-benzodioxine-2-carboxylic acid Chemical compound C=1C(N(C)C)=CC=C2C=1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 ISFWOCTVLCBYSR-UHFFFAOYSA-N 0.000 claims 1
- ZYHRODKZKDHELH-UHFFFAOYSA-N 4,4-dicyclohexyl-7-methoxy-1,3-benzodioxine-2-carboxylic acid Chemical compound C=1C(OC)=CC=C2C=1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 ZYHRODKZKDHELH-UHFFFAOYSA-N 0.000 claims 1
- CBGGTXULLJKPGU-UHFFFAOYSA-N 4,4-dicyclohexyl-7-methoxy-5-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C=1C(OC)=CC(C)=C2C=1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 CBGGTXULLJKPGU-UHFFFAOYSA-N 0.000 claims 1
- ROUBXFAVLIQQFT-UHFFFAOYSA-N 4,4-dicyclohexyl-7-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C=1C(C)=CC=C2C=1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 ROUBXFAVLIQQFT-UHFFFAOYSA-N 0.000 claims 1
- VLPQUKUASDWSKS-UHFFFAOYSA-N 4,4-dicyclohexyl-7-morpholin-4-yl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC(N3CCOCC3)=CC=C2C1(C1CCCCC1)C1CCCCC1 VLPQUKUASDWSKS-UHFFFAOYSA-N 0.000 claims 1
- JQUBLGPIULPKCS-UHFFFAOYSA-N 4,4-dicyclohexyl-7-phenylmethoxy-1,3-benzodioxine-2-carboxylic acid Chemical compound C=1C=C2C(C3CCCCC3)(C3CCCCC3)OC(C(=O)O)OC2=CC=1OCC1=CC=CC=C1 JQUBLGPIULPKCS-UHFFFAOYSA-N 0.000 claims 1
- DBQKLTSTMBXCTA-UHFFFAOYSA-N 4,4-dicyclohexyl-7-pyrrol-1-yl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC(N3C=CC=C3)=CC=C2C1(C1CCCCC1)C1CCCCC1 DBQKLTSTMBXCTA-UHFFFAOYSA-N 0.000 claims 1
- WYEOQDHXVWKTDD-UHFFFAOYSA-N 4,4-dicyclohexyl-8-(trifluoromethoxy)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=C(OC(F)(F)F)C=CC=C2C1(C1CCCCC1)C1CCCCC1 WYEOQDHXVWKTDD-UHFFFAOYSA-N 0.000 claims 1
- NTAQXGSXPPBJFK-UHFFFAOYSA-N 4,4-dicyclohexyl-8-fluoro-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=C(F)C=CC=C2C1(C1CCCCC1)C1CCCCC1 NTAQXGSXPPBJFK-UHFFFAOYSA-N 0.000 claims 1
- IXDXBIUPFXTVBB-UHFFFAOYSA-N 4,4-dicyclohexyl-8-methoxy-1,3-benzodioxine-2-carboxylic acid Chemical compound COC1=CC=CC2=C1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 IXDXBIUPFXTVBB-UHFFFAOYSA-N 0.000 claims 1
- YFKGJAVKSKZPSC-UHFFFAOYSA-N 4,4-dicyclohexyl-8-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound CC1=CC=CC2=C1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 YFKGJAVKSKZPSC-UHFFFAOYSA-N 0.000 claims 1
- CNOGCZUOGVSHQT-UHFFFAOYSA-N 4,4-dicyclohexylbenzo[g][1,3]benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC3=CC=CC=C3C=C2C1(C1CCCCC1)C1CCCCC1 CNOGCZUOGVSHQT-UHFFFAOYSA-N 0.000 claims 1
- FXMWJGVQPHEEHB-UHFFFAOYSA-N 4,4-dicyclohexylbenzo[h][1,3]benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC(C2=CC=CC=C2C=C2)=C2C1(C1CCCCC1)C1CCCCC1 FXMWJGVQPHEEHB-UHFFFAOYSA-N 0.000 claims 1
- DZTYTOKNBZNHIB-UHFFFAOYSA-N 5-(6-chloro-4,4-dicyclohexyl-1,3-benzodioxin-2-yl)-2h-tetrazole Chemical compound C12=CC(Cl)=CC=C2OC(C2=NNN=N2)OC1(C1CCCCC1)C1CCCCC1 DZTYTOKNBZNHIB-UHFFFAOYSA-N 0.000 claims 1
- DHKAHPFOIXOWHE-UHFFFAOYSA-N 5-(6-chloro-4,4-dicyclohexyl-1,3-benzodioxin-2-yl)-3h-1,3,4-oxadiazol-2-one Chemical compound C12=CC(Cl)=CC=C2OC(C=2OC(=O)NN=2)OC1(C1CCCCC1)C1CCCCC1 DHKAHPFOIXOWHE-UHFFFAOYSA-N 0.000 claims 1
- QIFNMQAHOULZJM-UHFFFAOYSA-N 6,8-dichloro-4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=C(Cl)C=C(Cl)C=C2C1(C1CCCCC1)C1CCCCC1 QIFNMQAHOULZJM-UHFFFAOYSA-N 0.000 claims 1
- NRWJQWMWMQRUNW-UHFFFAOYSA-N 6-(3-chlorophenoxy)-4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=C2C(C3CCCCC3)(C3CCCCC3)OC(C(=O)O)OC2=CC=C1OC1=CC=CC(Cl)=C1 NRWJQWMWMQRUNW-UHFFFAOYSA-N 0.000 claims 1
- SMIDBSMNWLETBS-UHFFFAOYSA-N 6-(4-chlorobenzoyl)-4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(C(=O)C=3C=CC(Cl)=CC=3)C=C2C1(C1CCCCC1)C1CCCCC1 SMIDBSMNWLETBS-UHFFFAOYSA-N 0.000 claims 1
- TWDRWHNYDGJARY-UHFFFAOYSA-N 6-(4-chlorophenoxy)-4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=C2C(C3CCCCC3)(C3CCCCC3)OC(C(=O)O)OC2=CC=C1OC1=CC=C(Cl)C=C1 TWDRWHNYDGJARY-UHFFFAOYSA-N 0.000 claims 1
- MEVCCTSZUVOZOO-UHFFFAOYSA-N 6-bromo-4,4-di(cycloheptyl)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(Br)C=C2C1(C1CCCCCC1)C1CCCCCC1 MEVCCTSZUVOZOO-UHFFFAOYSA-N 0.000 claims 1
- JLDUWYSFYXJSOJ-UHFFFAOYSA-N 6-chloro-4,4-di(cycloheptyl)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(Cl)C=C2C1(C1CCCCCC1)C1CCCCCC1 JLDUWYSFYXJSOJ-UHFFFAOYSA-N 0.000 claims 1
- MIJGJCGTZZGABX-UHFFFAOYSA-N 6-chloro-4,4-di(cycloheptyl)-7-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=2C=C(Cl)C(C)=CC=2OC(C(O)=O)OC1(C1CCCCCC1)C1CCCCCC1 MIJGJCGTZZGABX-UHFFFAOYSA-N 0.000 claims 1
- PSQPVSZHYMTKTM-UHFFFAOYSA-N 6-chloro-4,4-di(cyclooctyl)-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(Cl)C=C2C1(C1CCCCCCC1)C1CCCCCCC1 PSQPVSZHYMTKTM-UHFFFAOYSA-N 0.000 claims 1
- WETJKOLTAUGJRY-UHFFFAOYSA-N 6-chloro-4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(Cl)C=C2C1(C1CCCCC1)C1CCCCC1 WETJKOLTAUGJRY-UHFFFAOYSA-N 0.000 claims 1
- KOLNJYAVUKRGBP-UHFFFAOYSA-N 6-chloro-4,4-dicyclohexyl-2-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C)(C(O)=O)OC2=CC=C(Cl)C=C2C1(C1CCCCC1)C1CCCCC1 KOLNJYAVUKRGBP-UHFFFAOYSA-N 0.000 claims 1
- UNRMFSCCXVRPDR-UHFFFAOYSA-N 6-chloro-4,4-dicyclohexyl-5-fluoro-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC=C(Cl)C(F)=C2C1(C1CCCCC1)C1CCCCC1 UNRMFSCCXVRPDR-UHFFFAOYSA-N 0.000 claims 1
- NQYVUFAEKZROKZ-UHFFFAOYSA-N 6-chloro-4,4-dicyclohexyl-7-fluoro-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC(F)=C(Cl)C=C2C1(C1CCCCC1)C1CCCCC1 NQYVUFAEKZROKZ-UHFFFAOYSA-N 0.000 claims 1
- WYYPLKWWWOBYMJ-UHFFFAOYSA-N 6-chloro-4,4-dicyclohexyl-7-methoxy-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=2C=C(Cl)C(OC)=CC=2OC(C(O)=O)OC1(C1CCCCC1)C1CCCCC1 WYYPLKWWWOBYMJ-UHFFFAOYSA-N 0.000 claims 1
- KFAZMQCVANACCG-UHFFFAOYSA-N 6-chloro-4,4-dicyclohexyl-7-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound C1=2C=C(Cl)C(C)=CC=2OC(C(O)=O)OC1(C1CCCCC1)C1CCCCC1 KFAZMQCVANACCG-UHFFFAOYSA-N 0.000 claims 1
- ASNFHHPDFMGXNJ-UHFFFAOYSA-N 6-chloro-4,4-dicyclohexyl-8-fluoro-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=C(F)C=C(Cl)C=C2C1(C1CCCCC1)C1CCCCC1 ASNFHHPDFMGXNJ-UHFFFAOYSA-N 0.000 claims 1
- XKEPFFWGTPYHNI-UHFFFAOYSA-N 6-chloro-4,4-dicyclohexyl-8-methyl-1,3-benzodioxine-2-carboxylic acid Chemical compound CC1=CC(Cl)=CC2=C1OC(C(O)=O)OC2(C1CCCCC1)C1CCCCC1 XKEPFFWGTPYHNI-UHFFFAOYSA-N 0.000 claims 1
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- CSBYNSJIKIGCGU-UHFFFAOYSA-N 7-chloro-4,4-dicyclohexyl-1,3-benzodioxine-2-carboxylic acid Chemical compound O1C(C(=O)O)OC2=CC(Cl)=CC=C2C1(C1CCCCC1)C1CCCCC1 CSBYNSJIKIGCGU-UHFFFAOYSA-N 0.000 claims 1
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| PCT/EP2013/060172 WO2013171318A1 (en) | 2012-05-18 | 2013-05-16 | Benzo[1,3]dioxine derivatives and their use as lpar5 antagonists |
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| US20200215085A1 (en) * | 2017-07-19 | 2020-07-09 | Uti Limited Partnership | Method to Abate Acute Airway Hypersensitivity and Asthma Attacks |
| KR20250140741A (ko) | 2024-03-19 | 2025-09-26 | 경북대학교 산학협력단 | 알룰로스를 포함하는 혈전 예방 또는 개선용 조성물 및 이의 이용 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4056540A (en) | 1974-01-01 | 1977-11-01 | Bristol-Myers Company | 4-Phenyl-1,3-benzodioxans |
| US4056450A (en) | 1975-06-30 | 1977-11-01 | M & T Chemicals Inc. | Continuous detinning system |
| FR2424914A2 (fr) * | 1978-05-03 | 1979-11-30 | Roussel Uclaf | Nouveaux derives de (1-3) benzodioxine, un procede pour leur preparation et leur application comme medicaments |
| SE445553B (sv) * | 1978-05-03 | 1986-06-30 | Roussel Uclaf | /4h/-1,3-bensodioxan-2-karboxylsyraderivat |
| GB8310407D0 (en) * | 1982-05-12 | 1983-05-25 | Ici Plc | 1 3 - dioxan -5- ylalkenoic acids |
| FR2704857B1 (fr) * | 1993-05-07 | 1995-06-23 | Adir | Nouvelles benzodioxines substituées, leur procédé de préparation et les compositions pharmaceutiques les contenant. |
| EP1636585B2 (en) | 2003-05-20 | 2012-06-13 | Bayer HealthCare LLC | Diaryl ureas with kinase inhibiting activity |
| CN101124226A (zh) * | 2004-05-07 | 2008-02-13 | 记忆药物公司 | 1h-吲唑、苯并噻唑、1,2-苯并异噁唑、1,2-苯并异噻唑和色酮以及它们的制备和用途 |
| WO2010042600A2 (en) * | 2008-10-08 | 2010-04-15 | The Uab Research Foundation | Photo-activatable therapeutic agents and methods of using |
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2013
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