JP2016513135A5 - - Google Patents
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- Publication number
- JP2016513135A5 JP2016513135A5 JP2015560105A JP2015560105A JP2016513135A5 JP 2016513135 A5 JP2016513135 A5 JP 2016513135A5 JP 2015560105 A JP2015560105 A JP 2015560105A JP 2015560105 A JP2015560105 A JP 2015560105A JP 2016513135 A5 JP2016513135 A5 JP 2016513135A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- methyl
- dihydro
- phenyl
- dibenzo
- 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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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 92
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 52
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 40
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 31
- 229910052739 hydrogen Inorganic materials 0.000 claims 31
- 239000001257 hydrogen Substances 0.000 claims 31
- -1 hydroxy, amino Chemical group 0.000 claims 31
- 125000003545 alkoxy group Chemical group 0.000 claims 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 29
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- 150000002431 hydrogen Chemical class 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 125000004452 carbocyclyl group Chemical group 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000002252 acyl group Chemical group 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- VTZDPQGGOUEESD-UHFFFAOYSA-N 4-hexynoic acid Chemical compound CC#CCCC(O)=O VTZDPQGGOUEESD-UHFFFAOYSA-N 0.000 claims 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 8
- 125000002947 alkylene group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000004323 oxepin-2-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C(*)O1 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 5
- ZAWLXPIBKBSORZ-JOCHJYFZSA-N 2-[(3s)-6-[[11-methyl-9-(3-methylsulfonylpropoxy)-6,7-dihydrobenzo[d][1]benzoxepin-4-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C1=CC=C2C=3C(C)=CC(OCCCS(C)(=O)=O)=CC=3CCOC2=C1COC1=CC=C([C@H](CC(O)=O)CO2)C2=C1 ZAWLXPIBKBSORZ-JOCHJYFZSA-N 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- 208000010444 Acidosis Diseases 0.000 claims 2
- 208000009304 Acute Kidney Injury Diseases 0.000 claims 2
- 206010003210 Arteriosclerosis Diseases 0.000 claims 2
- 208000036487 Arthropathies Diseases 0.000 claims 2
- 206010003694 Atrophy Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- 206010013700 Drug hypersensitivity Diseases 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000013016 Hypoglycemia Diseases 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000012659 Joint disease Diseases 0.000 claims 2
- 208000007976 Ketosis Diseases 0.000 claims 2
- 208000001344 Macular Edema Diseases 0.000 claims 2
- 206010025415 Macular oedema Diseases 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- 208000029725 Metabolic bone disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 206010030113 Oedema Diseases 0.000 claims 2
- 206010049088 Osteopenia Diseases 0.000 claims 2
- 208000033626 Renal failure acute Diseases 0.000 claims 2
- 208000007536 Thrombosis Diseases 0.000 claims 2
- 206010047571 Visual impairment Diseases 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 230000007950 acidosis Effects 0.000 claims 2
- 208000026545 acidosis disease Diseases 0.000 claims 2
- 201000011040 acute kidney failure Diseases 0.000 claims 2
- 208000012998 acute renal failure Diseases 0.000 claims 2
- 210000000577 adipose tissue Anatomy 0.000 claims 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 2
- 150000004303 annulenes Chemical class 0.000 claims 2
- 230000036528 appetite Effects 0.000 claims 2
- 235000019789 appetite Nutrition 0.000 claims 2
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 2
- 230000037444 atrophy Effects 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 208000028683 bipolar I disease Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 201000006549 dyspepsia Diseases 0.000 claims 2
- 230000008482 dysregulation Effects 0.000 claims 2
- 206010016256 fatigue Diseases 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 2
- 201000008980 hyperinsulinism Diseases 0.000 claims 2
- 230000002218 hypoglycaemic effect Effects 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 206010022498 insulinoma Diseases 0.000 claims 2
- 230000004140 ketosis Effects 0.000 claims 2
- 230000000512 lipotoxic effect Effects 0.000 claims 2
- 201000010230 macular retinal edema Diseases 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 208000021255 pancreatic insulinoma Diseases 0.000 claims 2
- 235000019260 propionic acid Nutrition 0.000 claims 2
- 208000017443 reproductive system disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- 208000029257 vision disease Diseases 0.000 claims 2
- 230000004393 visual impairment Effects 0.000 claims 2
- QWKFHQBHGGWTKX-IZZNHLLZSA-N (1R,2R)-2-[4-[[10-methyl-8-(3-methylsulfonylpropoxy)-6H-benzo[c]chromen-4-yl]methylamino]phenyl]cyclopropane-1-carboxylic acid Chemical compound CC1=CC(=CC=2COC3=C(C=CC=C3C=21)CNC1=CC=C(C=C1)[C@H]1[C@@H](C1)C(=O)O)OCCCS(=O)(=O)C QWKFHQBHGGWTKX-IZZNHLLZSA-N 0.000 claims 1
- ZXRZZQNOFMDGER-NOZRDPDXSA-N (1S,2S)-2-[4-[(3-methyl-5-morpholin-4-yl-4,6-diazatricyclo[9.4.0.02,7]pentadeca-1(11),2,4,6,12,14-hexaen-14-yl)methoxy]phenyl]cyclopropane-1-carboxylic acid Chemical compound CC1=C2C(=NC(=N1)N1CCOCC1)CCCC1=C2C=C(C=C1)COC1=CC=C(C=C1)[C@@H]1[C@H](C1)C(=O)O ZXRZZQNOFMDGER-NOZRDPDXSA-N 0.000 claims 1
- UZNIRXPXTOGJRM-IHLOFXLRSA-N (1S,2S)-2-[4-[[13-(3-ethylsulfonylpropoxy)-4-tricyclo[9.4.0.02,7]pentadeca-1(11),2(7),3,5,12,14-hexaenyl]methylamino]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(C)S(=O)(=O)CCCOC1=CC2=C(C3=C(CCC2)C=CC(=C3)CNC3=CC=C(C=C3)[C@@H]3[C@H](C3)C(=O)O)C=C1 UZNIRXPXTOGJRM-IHLOFXLRSA-N 0.000 claims 1
- BBOZFFRFDZWJKG-WDYNHAJCSA-N (1S,2S)-2-[4-[[13-(3-methylsulfonylpropoxy)-4-tricyclo[9.4.0.02,7]pentadeca-1(11),2(7),3,5,12,14-hexaenyl]methylamino]phenyl]cyclopropane-1-carboxylic acid Chemical compound CS(=O)(=O)CCCOC1=CC2=C(C3=C(CCC2)C=CC(=C3)CNC3=CC=C(C=C3)[C@@H]3[C@H](C3)C(=O)O)C=C1 BBOZFFRFDZWJKG-WDYNHAJCSA-N 0.000 claims 1
- XYGJZJFYTQZECR-PXJZQJOASA-N (1S,2S)-2-[4-[[5-ethyl-9-(3-methylsulfonylpropoxy)-6,7-dihydrobenzo[d][1]benzazepin-2-yl]methoxy]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(C)N1C2=C(C3=C(CC1)C=C(C=C3)OCCCS(=O)(=O)C)C=C(C=C2)COC2=CC=C(C=C2)[C@@H]2[C@H](C2)C(=O)O XYGJZJFYTQZECR-PXJZQJOASA-N 0.000 claims 1
- SRWGXOCQXSLXIY-VPUSJEBWSA-N (1S,2S)-2-[4-[[9-(2-ethoxyethoxy)-6,7-dihydrobenzo[d][1]benzoxepin-2-yl]methylamino]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(C)OCCOC1=CC2=C(C3=C(OCC2)C=CC(=C3)CNC3=CC=C(C=C3)[C@@H]3[C@H](C3)C(=O)O)C=C1 SRWGXOCQXSLXIY-VPUSJEBWSA-N 0.000 claims 1
- YLGDCKPEOLQJFT-FTJBHMTQSA-N (1S,2S)-2-[4-[[9-(3-ethylsulfonylpropoxy)-11-methyl-6,7-dihydrobenzo[d][1]benzoxepin-2-yl]methoxy]-2-fluorophenyl]cyclopropane-1-carboxylic acid Chemical compound C(C)S(=O)(=O)CCCOC1=CC2=C(C3=C(OCC2)C=CC(=C3)COC3=CC(=C(C=C3)[C@@H]3[C@H](C3)C(=O)O)F)C(=C1)C YLGDCKPEOLQJFT-FTJBHMTQSA-N 0.000 claims 1
- VLCZMSUIFYTVHK-VPUSJEBWSA-N (1S,2S)-2-[4-[[9-(3-methylsulfonylpropoxy)-6,7-dihydrobenzo[d][1]benzoxepin-2-yl]methoxy]phenyl]cyclopropane-1-carboxylic acid Chemical compound CS(=O)(=O)CCCOC1=CC2=C(C3=C(OCC2)C=CC(=C3)COC3=CC=C(C=C3)[C@@H]3[C@H](C3)C(=O)O)C=C1 VLCZMSUIFYTVHK-VPUSJEBWSA-N 0.000 claims 1
- VFBVSVRCAJBJKR-VPUSJEBWSA-N (1S,2S)-2-[4-[[9-(3-methylsulfonylpropoxy)-6,7-dihydrobenzo[d][1]benzoxepin-2-yl]methylamino]phenyl]cyclopropane-1-carboxylic acid Chemical compound CS(=O)(=O)CCCOC1=CC2=C(C3=C(OCC2)C=CC(=C3)CNC3=CC=C(C=C3)[C@@H]3[C@H](C3)C(=O)O)C=C1 VFBVSVRCAJBJKR-VPUSJEBWSA-N 0.000 claims 1
- FTNHPSKGTRCBES-RPBOFIJWSA-N (1s,2s)-2-[4-[[10-methyl-8-(3-methylsulfonylpropoxy)-6h-benzo[c]chromen-2-yl]methoxy]phenyl]cyclopropane-1-carboxylic acid Chemical compound C1=C2C=3C(C)=CC(OCCCS(C)(=O)=O)=CC=3COC2=CC=C1COC(C=C1)=CC=C1[C@H]1C[C@@H]1C(O)=O FTNHPSKGTRCBES-RPBOFIJWSA-N 0.000 claims 1
- RBCAFEQTCYGZJN-RPBOFIJWSA-N (1s,2s)-2-[4-[[10-methyl-8-(3-methylsulfonylpropoxy)-6h-benzo[c]chromen-2-yl]methylamino]phenyl]cyclopropane-1-carboxylic acid Chemical compound C1=C2C=3C(C)=CC(OCCCS(C)(=O)=O)=CC=3COC2=CC=C1CNC(C=C1)=CC=C1[C@H]1C[C@@H]1C(O)=O RBCAFEQTCYGZJN-RPBOFIJWSA-N 0.000 claims 1
- UAVADONVEHUQBW-FTJBHMTQSA-N (1s,2s)-2-[4-[[11-methyl-9-(3-methylsulfonylpropoxy)-6,7-dihydrobenzo[d][1]benzoxepin-2-yl]methoxy]phenyl]cyclopropane-1-carboxylic acid Chemical compound C1=C2C=3C(C)=CC(OCCCS(C)(=O)=O)=CC=3CCOC2=CC=C1COC(C=C1)=CC=C1[C@H]1C[C@@H]1C(O)=O UAVADONVEHUQBW-FTJBHMTQSA-N 0.000 claims 1
- RNUXLXCFOCANHO-IZLXSDGUSA-N (1s,2s)-2-[4-[[3-(2-ethoxyethoxy)-5,7-dihydrobenzo[d][2]benzoxepin-10-yl]methylamino]phenyl]cyclopropane-1-carboxylic acid Chemical compound C=1C(OCCOCC)=CC=C(C2=C3)C=1COCC2=CC=C3CNC(C=C1)=CC=C1[C@H]1C[C@@H]1C(O)=O RNUXLXCFOCANHO-IZLXSDGUSA-N 0.000 claims 1
- KBFHYWVNASLSDY-DGPALRBDSA-N (1s,2s)-2-[4-[[3-(3-ethylsulfonylpropoxy)-1-methyl-6,7-dihydro-5h-dibenzo[1,3-a:1',3'-d][7]annulen-10-yl]methoxy]phenyl]cyclopropane-1-carboxylic acid Chemical compound C=1C(OCCCS(=O)(=O)CC)=CC(C)=C(C2=C3)C=1CCCC2=CC=C3COC(C=C1)=CC=C1[C@H]1C[C@@H]1C(O)=O KBFHYWVNASLSDY-DGPALRBDSA-N 0.000 claims 1
- YPOMXZKYMWUDBI-IZLXSDGUSA-N (1s,2s)-2-[4-[[3-(3-methylsulfonylpropoxy)-5,7-dihydrobenzo[d][2]benzoxepin-10-yl]methylamino]phenyl]cyclopropane-1-carboxylic acid Chemical compound C=1C(OCCCS(=O)(=O)C)=CC=C(C2=C3)C=1COCC2=CC=C3CNC(C=C1)=CC=C1[C@H]1C[C@@H]1C(O)=O YPOMXZKYMWUDBI-IZLXSDGUSA-N 0.000 claims 1
- RSCJIQIRRUWLCA-SXOMAYOGSA-N (1s,2s)-2-[4-[[3-(3-methylsulfonylpropoxy)-6,7-dihydrobenzo[d][1]benzoxepin-10-yl]methylamino]phenyl]cyclopropane-1-carboxylic acid Chemical compound C=1C(OCCCS(=O)(=O)C)=CC=C(C2=C3)C=1OCCC2=CC=C3CNC(C=C1)=CC=C1[C@H]1C[C@@H]1C(O)=O RSCJIQIRRUWLCA-SXOMAYOGSA-N 0.000 claims 1
- YMTDLLHKQFSZBG-IAPPQJPRSA-N (1s,2s)-2-[4-[[5-methyl-7-(3-methylsulfonylpropoxy)-9,10-dihydrophenanthren-3-yl]methoxy]phenyl]cyclopropane-1-carboxylic acid Chemical compound C1=C2C=3C(C)=CC(OCCCS(C)(=O)=O)=CC=3CCC2=CC=C1COC(C=C1)=CC=C1[C@H]1C[C@@H]1C(O)=O YMTDLLHKQFSZBG-IAPPQJPRSA-N 0.000 claims 1
- JNHPWWJYPADQAM-RPBOFIJWSA-N (1s,2s)-2-[4-[[8-(2-ethoxyethoxy)-10-methyl-6h-benzo[c]chromen-2-yl]methylamino]phenyl]cyclopropane-1-carboxylic acid Chemical compound C=1C(OCCOCC)=CC(C)=C(C2=C3)C=1COC2=CC=C3CNC(C=C1)=CC=C1[C@H]1C[C@@H]1C(O)=O JNHPWWJYPADQAM-RPBOFIJWSA-N 0.000 claims 1
- YCUCEICXEVBLIV-SXOMAYOGSA-N (1s,2s)-2-[4-[[9-(3-ethylsulfonylpropoxy)-11-methyl-6,7-dihydrobenzo[d][1]benzoxepin-2-yl]methoxy]phenyl]cyclopropane-1-carboxylic acid Chemical compound C=1C(OCCCS(=O)(=O)CC)=CC(C)=C(C2=C3)C=1CCOC2=CC=C3COC(C=C1)=CC=C1[C@H]1C[C@@H]1C(O)=O YCUCEICXEVBLIV-SXOMAYOGSA-N 0.000 claims 1
- RKMRQTMCXUOJRM-SANMLTNESA-N (3S)-3-[4-[[13-(3-methylsulfonylpropoxy)-4-tricyclo[9.4.0.02,7]pentadeca-1(11),2(7),3,5,12,14-hexaenyl]methoxy]phenyl]hex-4-ynoic acid Chemical compound CS(=O)(=O)CCCOC1=CC2=C(C3=C(CCC2)C=CC(=C3)COC3=CC=C(C=C3)[C@H](CC(=O)O)C#CC)C=C1 RKMRQTMCXUOJRM-SANMLTNESA-N 0.000 claims 1
- LEWAITPXKDMFDL-SANMLTNESA-N (3S)-3-[4-[[13-(3-methylsulfonylpropoxy)-4-tricyclo[9.4.0.02,7]pentadeca-1(11),2(7),3,5,12,14-hexaenyl]methylamino]phenyl]hex-4-ynoic acid Chemical compound CS(=O)(=O)CCCOC1=CC2=C(C3=C(CCC2)C=CC(=C3)CNC3=CC=C(C=C3)[C@H](CC(=O)O)C#CC)C=C1 LEWAITPXKDMFDL-SANMLTNESA-N 0.000 claims 1
- LQBOJUSLNBXXFZ-MHZLTWQESA-N (3S)-3-[4-[[15-methyl-13-(3-methylsulfonylpropoxy)-4-tricyclo[9.4.0.02,7]pentadeca-1(11),2(7),3,5,12,14-hexaenyl]methoxy]phenyl]hex-4-ynoic acid Chemical compound CC1=CC(=CC2=C1C1=C(CCC2)C=CC(=C1)COC1=CC=C(C=C1)[C@H](CC(=O)O)C#CC)OCCCS(=O)(=O)C LQBOJUSLNBXXFZ-MHZLTWQESA-N 0.000 claims 1
- BQJPAPVGKLJRFA-LITSAYRRSA-N (3S)-3-[4-[[15-methyl-13-[(3R)-oxolan-3-yl]oxy-4-tricyclo[9.4.0.02,7]pentadeca-1(11),2(7),3,5,12,14-hexaenyl]methoxy]phenyl]hex-4-ynoic acid Chemical compound CC1=CC(=CC2=C1C1=C(CCC2)C=CC(=C1)COC1=CC=C(C=C1)[C@H](CC(=O)O)C#CC)O[C@H]1COCC1 BQJPAPVGKLJRFA-LITSAYRRSA-N 0.000 claims 1
- NZKPGFORNZSLOL-VWLOTQADSA-N (3S)-3-[4-[[3-methyl-5-(3-methylsulfonylpropoxy)-4,6-diazatricyclo[9.4.0.02,7]pentadeca-1(11),2,4,6,12,14-hexaen-14-yl]methoxy]phenyl]hex-4-ynoic acid Chemical compound CC1=C2C(=NC(=N1)OCCCS(=O)(=O)C)CCCC1=C2C=C(C=C1)COC1=CC=C(C=C1)[C@H](CC(=O)O)C#CC NZKPGFORNZSLOL-VWLOTQADSA-N 0.000 claims 1
- OSIVDCAGXJSMRC-SANMLTNESA-N (3S)-3-[4-[[5-(3-ethylsulfonylpropoxy)-6-azatricyclo[9.4.0.02,7]pentadeca-1(11),2(7),3,5,12,14-hexaen-14-yl]methoxy]phenyl]hex-4-ynoic acid Chemical compound C(C)S(=O)(=O)CCCOC1=CC=C2C(=N1)CCCC1=C2C=C(C=C1)COC1=CC=C(C=C1)[C@H](CC(=O)O)C#CC OSIVDCAGXJSMRC-SANMLTNESA-N 0.000 claims 1
- JXKPFSTWHVWGBY-VWLOTQADSA-N (3S)-3-[4-[[5-(3-methylsulfonylpropoxy)-6-azatricyclo[9.4.0.02,7]pentadeca-1(11),2(7),3,5,12,14-hexaen-14-yl]methoxy]phenyl]hex-4-ynoic acid Chemical compound CS(=O)(=O)CCCOC1=CC=C2C(=N1)CCCC1=C2C=C(C=C1)COC1=CC=C(C=C1)[C@H](CC(=O)O)C#CC JXKPFSTWHVWGBY-VWLOTQADSA-N 0.000 claims 1
- UAJIMIBESMZHGC-VWLOTQADSA-N (3S)-3-[4-[[6,6-dimethyl-9-(3-methylsulfonylpropoxy)-7H-benzo[d][1]benzoxepin-2-yl]methoxy]phenyl]hex-4-ynoic acid Chemical compound CC1(CC2=C(C3=C(O1)C=CC(=C3)COC3=CC=C(C=C3)[C@H](CC(=O)O)C#CC)C=CC(=C2)OCCCS(=O)(=O)C)C UAJIMIBESMZHGC-VWLOTQADSA-N 0.000 claims 1
- KYBSQIFXFHONSB-SANMLTNESA-N (3S)-3-[4-[[7-(2-ethoxyethoxy)-5-methyl-9,10-dihydrophenanthren-3-yl]methoxy]phenyl]hex-4-ynoic acid Chemical compound C(C)OCCOC1=CC(=C2C=3C=C(C=CC3CCC2=C1)COC1=CC=C(C=C1)[C@H](CC(=O)O)C#CC)C KYBSQIFXFHONSB-SANMLTNESA-N 0.000 claims 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims 1
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- DIZDRDQFMBSVFK-JOCHJYFZSA-N 2-[(3S)-6-[[3-(2-ethoxyethoxy)-5,7-dihydrobenzo[d][2]benzoxepin-10-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C(C)OCCOC1=CC2=C(C3=C(COC2)C=CC(=C3)COC2=CC3=C([C@@H](CO3)CC(=O)O)C=C2)C=C1 DIZDRDQFMBSVFK-JOCHJYFZSA-N 0.000 claims 1
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- NFNZPZSQYYAYQH-LJQANCHMSA-N 2-[(3S)-6-[[3-(3-methylsulfonylpropoxy)benzo[d][1,3]benzodioxepin-10-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound CS(=O)(=O)CCCOC1=CC2=C(C3=C(OCO2)C=CC(=C3)COC2=CC3=C([C@@H](CO3)CC(=O)O)C=C2)C=C1 NFNZPZSQYYAYQH-LJQANCHMSA-N 0.000 claims 1
- UABZXOHSISTHJY-HSZRJFAPSA-N 2-[(3S)-6-[[5-methyl-7-(3-methylsulfonylpropoxy)-9,10-dihydrophenanthren-3-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound CC1=C2C=3C=C(C=CC3CCC2=CC(=C1)OCCCS(=O)(=O)C)COC1=CC2=C([C@@H](CO2)CC(=O)O)C=C1 UABZXOHSISTHJY-HSZRJFAPSA-N 0.000 claims 1
- JEICBCVITKTKER-JOCHJYFZSA-N 2-[(3S)-6-[[6,6-dimethyl-9-(3-methylsulfonylpropoxy)-7H-benzo[d][1]benzoxepin-2-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound CC1(CC2=C(C3=C(O1)C=CC(=C3)COC3=CC1=C([C@@H](CO1)CC(=O)O)C=C3)C=CC(=C2)OCCCS(=O)(=O)C)C JEICBCVITKTKER-JOCHJYFZSA-N 0.000 claims 1
- FHALSIDSDYBJCO-HSZRJFAPSA-N 2-[(3S)-6-[[7-(2-ethoxyethoxy)-5-methyl-9,10-dihydrophenanthren-3-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound CCOCCOC1=CC(C)=C2C(CCC3=C2C=C(COC2=CC4=C(C=C2)[C@H](CC(O)=O)CO4)C=C3)=C1 FHALSIDSDYBJCO-HSZRJFAPSA-N 0.000 claims 1
- CHVDQJTUOOFUOS-JOCHJYFZSA-N 2-[(3s)-6-[[1-methyl-3-(3-methylsulfonylpropoxy)-5,7-dihydrobenzo[d][2]benzoxepin-10-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C1=C2C=3C(C)=CC(OCCCS(C)(=O)=O)=CC=3COCC2=CC=C1COC1=CC=C([C@H](CC(O)=O)CO2)C2=C1 CHVDQJTUOOFUOS-JOCHJYFZSA-N 0.000 claims 1
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- QGGXCKUJHCKJBI-XMMPIXPASA-N 2-[(3s)-6-[[1-methyl-3-(3-methylsulfonylpropoxy)-6,7-dihydro-5h-dibenzo[1,3-d:1',3'-g][7]annulen-10-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C1=C2C=3C(C)=CC(OCCCS(C)(=O)=O)=CC=3CCCC2=CC=C1COC1=CC=C([C@H](CC(O)=O)CO2)C2=C1 QGGXCKUJHCKJBI-XMMPIXPASA-N 0.000 claims 1
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- NRMMLXDUOGGYPX-JOCHJYFZSA-N 2-[(3s)-6-[[11-methyl-9-(3-methylsulfonylpropoxy)-6,7-dihydrobenzo[d][1]benzoxepin-2-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C1=C2C=3C(C)=CC(OCCCS(C)(=O)=O)=CC=3CCOC2=CC=C1COC1=CC=C([C@H](CC(O)=O)CO2)C2=C1 NRMMLXDUOGGYPX-JOCHJYFZSA-N 0.000 claims 1
- WXWPSTWLLGSKQG-XMMPIXPASA-N 2-[(3s)-6-[[3-(2-ethoxyethoxy)-1-methyl-6,7-dihydro-5h-dibenzo[1,3-a:1',3'-d][7]annulen-10-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C=1C(OCCOCC)=CC(C)=C(C2=C3)C=1CCCC2=CC=C3COC1=CC=C([C@H](CC(O)=O)CO2)C2=C1 WXWPSTWLLGSKQG-XMMPIXPASA-N 0.000 claims 1
- QWZFGUIHCGIENE-HSZRJFAPSA-N 2-[(3s)-6-[[3-(2-ethoxyethoxy)-6,7-dihydro-5h-dibenzo[3,1-d:3',1'-f][7]annulen-10-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C=1C(OCCOCC)=CC=C(C2=C3)C=1CCCC2=CC=C3COC1=CC=C([C@H](CC(O)=O)CO2)C2=C1 QWZFGUIHCGIENE-HSZRJFAPSA-N 0.000 claims 1
- QLUNPCXDMXTHMX-RUZDIDTESA-N 2-[(3s)-6-[[3-(3-ethylsulfonylpropoxy)-1-methyl-6,7-dihydro-5h-dibenzo[1,3-a:1',3'-d][7]annulen-10-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C=1C(OCCCS(=O)(=O)CC)=CC(C)=C(C2=C3)C=1CCCC2=CC=C3COC1=CC=C([C@H](CC(O)=O)CO2)C2=C1 QLUNPCXDMXTHMX-RUZDIDTESA-N 0.000 claims 1
- PSQDSVFJOIJRQM-HSZRJFAPSA-N 2-[(3s)-6-[[3-fluoro-9-(2-morpholin-4-ylethoxy)-6,7-dihydro-5h-dibenzo[4,3-b:3',1'-e][7]annulen-2-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C([C@H](C1=CC=2)CC(=O)O)OC1=CC=2OCC(C(=C1)F)=CC(C2=CC=3)=C1CCCC2=CC=3OCCN1CCOCC1 PSQDSVFJOIJRQM-HSZRJFAPSA-N 0.000 claims 1
- YGTIDXZAEKNOHN-OAQYLSRUSA-N 2-[(3s)-6-[[3-fluoro-9-(3-methylsulfonylpropoxy)-6,7-dihydro-5h-dibenzo[4,3-b:3',1'-e][7]annulen-2-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C=1C(OCCCS(=O)(=O)C)=CC=C(C2=C3)C=1CCCC2=CC(F)=C3COC1=CC=C([C@H](CC(O)=O)CO2)C2=C1 YGTIDXZAEKNOHN-OAQYLSRUSA-N 0.000 claims 1
- YQSHYBNOSHXHPS-HYBUGGRVSA-N 2-[(3s)-6-[[3-fluoro-9-[(3r)-oxolan-3-yl]oxy-6,7-dihydro-5h-dibenzo[3,4-a:3',1'-c][7]annulen-2-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C([C@H](C1=CC=2)CC(=O)O)OC1=CC=2OCC(C(=C1)F)=CC(C2=CC=3)=C1CCCC2=CC=3O[C@@H]1CCOC1 YQSHYBNOSHXHPS-HYBUGGRVSA-N 0.000 claims 1
- CXRACAVAWUNNHW-JOCHJYFZSA-N 2-[(3s)-6-[[5-methyl-7-(3-methylsulfonylpropoxy)-9,10-dihydrophenanthren-1-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C1=C2[C@H](CC(O)=O)COC2=CC(OCC2=C3CCC=4C=C(OCCCS(C)(=O)=O)C=C(C=4C3=CC=C2)C)=C1 CXRACAVAWUNNHW-JOCHJYFZSA-N 0.000 claims 1
- XDQMAUSWXNPZBT-HXUWFJFHSA-N 2-[(3s)-6-[[8-(2-ethoxyethoxy)-10-methyl-6h-benzo[c]chromen-2-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C1=C2[C@H](CC(O)=O)COC2=CC(OCC2=CC=C3OCC=4C(C3=C2)=C(C)C=C(C=4)OCCOCC)=C1 XDQMAUSWXNPZBT-HXUWFJFHSA-N 0.000 claims 1
- XXHAAHYYRJTNES-JOCHJYFZSA-N 2-[(3s)-6-[[9-(2-ethoxyethoxy)-11-methyl-6,7-dihydrobenzo[d][1]benzoxepin-2-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C=1C(OCCOCC)=CC(C)=C(C2=C3)C=1CCOC2=CC=C3COC1=CC=C([C@H](CC(O)=O)CO2)C2=C1 XXHAAHYYRJTNES-JOCHJYFZSA-N 0.000 claims 1
- MOAZPCNVWQGUFC-HSZRJFAPSA-N 2-[(3s)-6-[[9-(3-ethylsulfonylpropoxy)-11-methyl-6,7-dihydrobenzo[d][1]benzoxepin-2-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C=1C(OCCCS(=O)(=O)CC)=CC(C)=C(C2=C3)C=1CCOC2=CC=C3COC1=CC=C([C@H](CC(O)=O)CO2)C2=C1 MOAZPCNVWQGUFC-HSZRJFAPSA-N 0.000 claims 1
- SRJBVWQYRMQPSB-JOCHJYFZSA-N 2-[(3s)-6-[[9-(3-ethylsulfonylpropoxy)-3-fluoro-6,7-dihydro-5h-dibenzo[4,3-b:3',1'-e][7]annulen-2-yl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C=1C(OCCCS(=O)(=O)CC)=CC=C(C2=C3)C=1CCCC2=CC(F)=C3COC1=CC=C([C@H](CC(O)=O)CO2)C2=C1 SRJBVWQYRMQPSB-JOCHJYFZSA-N 0.000 claims 1
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| MX2018007844A (es) | 2015-12-22 | 2019-01-21 | Jiangsu Hengrui Medicine Co | Derivado de benzopiperidina, metodo de preparacion del mismo y su uso medico del mismo. |
| KR102538719B1 (ko) | 2016-12-08 | 2023-06-01 | 메르크 파텐트 게엠베하 | 중합가능한 화합물 및 액정 디스플레이에서 이의 용도 |
| CN108218824B (zh) * | 2016-12-09 | 2020-06-26 | 中国科学院大连化学物理研究所 | 二苯基并[b，d]氧杂环庚烷化合物及其制备和应用 |
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| JP6626524B2 (ja) | 2018-03-29 | 2019-12-25 | 日本碍子株式会社 | 電気加熱型触媒用担体 |
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| CN110105193B (zh) * | 2019-05-31 | 2022-03-22 | 杭州科耀医药科技有限公司 | 一种2-卤-5-溴苯甲酸的合成方法 |
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| JP3505189B2 (ja) | 1997-02-10 | 2004-03-08 | ファイザー・プロダクツ・インク | ２−アミノ−６−（２−置換−４−フェノキシ）−置換ピリジン |
| WO2001030764A1 (en) | 1999-10-22 | 2001-05-03 | Takeda Chemical Industries, Ltd. | 1-substituted phenyl-1-(1h-imidazol-4-yl) alcohols, process for producing the same and use thereof |
| AU2003277576A1 (en) * | 2002-11-08 | 2004-06-07 | Takeda Pharmaceutical Company Limited | Receptor function controlling agent |
| CN1735408A (zh) * | 2002-11-08 | 2006-02-15 | 武田药品工业株式会社 | 受体机能调节剂 |
| EP1630152A4 (en) * | 2003-05-30 | 2009-09-23 | Takeda Pharmaceutical | CONDENSED CYCLIC COMPOUND |
| WO2005051890A1 (en) * | 2003-11-19 | 2005-06-09 | Smithkline Beecham Corporation | Aminophenylcyclopropyl carboxylic acids and derivatives as agonists to gpr40 |
| JP4074616B2 (ja) * | 2003-12-25 | 2008-04-09 | 武田薬品工業株式会社 | ３−（４−ベンジルオキシフェニル）プロパン酸誘導体 |
| AU2004309271A1 (en) | 2003-12-25 | 2005-07-14 | Takeda Pharmaceutical Company Limited | 3-(4-benzyloxyphenyl)propanoic acid derivatives |
| JP5299810B2 (ja) * | 2004-02-27 | 2013-09-25 | アムジエン・インコーポレーテツド | 代謝疾患の治療に使用するための、化合物、薬学的組成物及び方法 |
| JP5084503B2 (ja) * | 2005-07-29 | 2012-11-28 | 武田薬品工業株式会社 | シクロプロパンカルボン酸化合物 |
| CA2646430A1 (en) * | 2006-03-14 | 2007-09-20 | Amgen Inc. | Bicyclic carboxylic acid derivatives useful for treating metabolic disorders |
| TW200815377A (en) | 2006-04-24 | 2008-04-01 | Astellas Pharma Inc | Oxadiazolidinedione compound |
| BRPI0713378A8 (pt) * | 2006-06-27 | 2018-01-02 | Takeda Pharmaceutical | composto, pró-droga, modulador da função do receptor gpr40, agente farmacêutico uso do composto, e, método de produção de uma forma opticamente ativa de um composto |
| CA2662305C (en) | 2006-09-07 | 2012-04-17 | Amgen Inc. | Heterocyclic gpr40 modulators |
| EP2139843B1 (en) * | 2007-04-16 | 2013-12-25 | Amgen, Inc | Substituted biphenyl phenoxy-, thiophenyl- and aminophenylpropanoic acid gpr40 modulators |
| PE20090595A1 (es) | 2007-08-15 | 2009-06-06 | Glaxo Group Ltd | Derivados de quinoliniloxipiperidina y pirrolidina como antagonistas del receptor h1 |
| CA2703217A1 (en) * | 2007-10-29 | 2009-05-07 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| EP2423176A4 (en) * | 2009-04-22 | 2012-11-07 | Astellas Pharma Inc | CARBOXYLIC ACID COMPOUND |
| WO2010143733A1 (en) | 2009-06-09 | 2010-12-16 | Takeda Pharmaceutical Company Limited | Novel fused cyclic compound and use thereof |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
-
2014
- 2014-02-28 EP EP14756272.2A patent/EP2963027B1/en active Active
- 2014-02-28 WO PCT/KR2014/001686 patent/WO2014133361A1/ko not_active Ceased
- 2014-02-28 AU AU2014221489A patent/AU2014221489B2/en not_active Ceased
- 2014-02-28 KR KR1020140024555A patent/KR101735787B1/ko not_active Expired - Fee Related
- 2014-02-28 JP JP2015560105A patent/JP6387023B2/ja not_active Expired - Fee Related
- 2014-02-28 CA CA2900348A patent/CA2900348C/en active Active
- 2014-02-28 US US14/771,049 patent/US9643946B2/en not_active Expired - Fee Related
- 2014-02-28 CN CN201711200963.6A patent/CN108017603B/zh not_active Expired - Fee Related
- 2014-02-28 ES ES14756272T patent/ES2709195T3/es active Active
- 2014-02-28 CN CN201480011110.6A patent/CN105209448B/zh not_active Expired - Fee Related
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