JP2018529744A5 - - Google Patents
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- JP2018529744A5 JP2018529744A5 JP2018517526A JP2018517526A JP2018529744A5 JP 2018529744 A5 JP2018529744 A5 JP 2018529744A5 JP 2018517526 A JP2018517526 A JP 2018517526A JP 2018517526 A JP2018517526 A JP 2018517526A JP 2018529744 A5 JP2018529744 A5 JP 2018529744A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- alkyl
- pyrazole
- cyclopropyl
- carboxylic acid
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 49
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 32
- 125000001424 substituent group Chemical group 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000002619 bicyclic group Chemical group 0.000 claims 12
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims 10
- 125000002098 pyridazinyl group Chemical group 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 10
- 125000001425 triazolyl group Chemical group 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- -1 6-methyl-5,6-dihydro-4H-cyclopentapyrazol-1-yl Chemical group 0.000 claims 6
- 125000002883 imidazolyl group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims 4
- 208000009304 Acute Kidney Injury Diseases 0.000 claims 3
- 208000033626 Renal failure acute Diseases 0.000 claims 3
- 201000011040 acute kidney failure Diseases 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- LGKNCSVHCNCJQG-UHFFFAOYSA-N 1-azaspiro[4.5]decane Chemical compound C1CCNC21CCCCC2 LGKNCSVHCNCJQG-UHFFFAOYSA-N 0.000 claims 2
- YXDVRIQBOMUBEQ-UHFFFAOYSA-N 2-oxa-8-azaspiro[5.5]undecane Chemical compound C1CCNCC21COCCC2 YXDVRIQBOMUBEQ-UHFFFAOYSA-N 0.000 claims 2
- HVFHYYCWZWCTMW-UHFFFAOYSA-N 4-azaspiro[2.5]octane Chemical compound C1CC11NCCCC1 HVFHYYCWZWCTMW-UHFFFAOYSA-N 0.000 claims 2
- FTGUMOQCPJEKOR-UHFFFAOYSA-N 6-oxa-9-azaspiro[4.5]decane Chemical compound C1CCCC21OCCNC2 FTGUMOQCPJEKOR-UHFFFAOYSA-N 0.000 claims 2
- JFNPSSKPSOKMJH-UHFFFAOYSA-N 7-azaspiro[4.5]decane Chemical compound C1CCCC21CNCCC2 JFNPSSKPSOKMJH-UHFFFAOYSA-N 0.000 claims 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- BLVUWLUVHINCRB-IRSIHTCSSA-N C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1[C@@H](CCC1)COCC)C(=O)O Chemical compound C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1[C@@H](CCC1)COCC)C(=O)O BLVUWLUVHINCRB-IRSIHTCSSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 208000024412 Friedreich ataxia Diseases 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 208000032376 Lung infection Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- XTRAFXAEDBHOTR-UHFFFAOYSA-N 1-[3-[3-(azepane-1-carbonyl)cyclohexen-1-yl]phenyl]-5-cyclopropylpyrazole-4-carboxylic acid Chemical compound N1(CCCCCC1)C(=O)C1CCCC(=C1)C1=CC(=CC=C1)N1N=CC(=C1C1CC1)C(=O)O XTRAFXAEDBHOTR-UHFFFAOYSA-N 0.000 claims 1
- FJVNIRYRIYZUJL-NJQOZVNVSA-N 5-[(1R,2R)-2-(1-methyltriazol-4-yl)cyclopropyl]-1-[3-[1-(1-phenylethyl)piperidin-3-yl]phenyl]pyrazole-4-carboxylic acid Chemical compound CN1N=NC(=C1)[C@H]1[C@@H](C1)C1=C(C=NN1C1=CC(=CC=C1)C1CN(CCC1)C(C)C1=CC=CC=C1)C(=O)O FJVNIRYRIYZUJL-NJQOZVNVSA-N 0.000 claims 1
- IXLVUUFUDRJUSL-RPBOFIJWSA-N 5-[[4-(3-acetamidophenyl)phenyl]methyl]-n-[(1s,2r)-2-phenylcyclopropyl]-1,3-oxazole-4-carboxamide Chemical compound CC(=O)NC1=CC=CC(C=2C=CC(CC3=C(N=CO3)C(=O)N[C@@H]3[C@H](C3)C=3C=CC=CC=3)=CC=2)=C1 IXLVUUFUDRJUSL-RPBOFIJWSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- ZPAXNFARPRVNNR-UHFFFAOYSA-N C(C)(C)(C)OC(=O)N1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O Chemical compound C(C)(C)(C)OC(=O)N1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O ZPAXNFARPRVNNR-UHFFFAOYSA-N 0.000 claims 1
- HCXUSVGZPVNDOZ-IPNZSQQUSA-N C(C)(C)(C)OC(=O)N1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1[C@H]1[C@@H](C1)C=1N=NN(C=1)C)C(=O)O Chemical compound C(C)(C)(C)OC(=O)N1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1[C@H]1[C@@H](C1)C=1N=NN(C=1)C)C(=O)O HCXUSVGZPVNDOZ-IPNZSQQUSA-N 0.000 claims 1
- BBOYBMOHXVYOQO-JHRSTNGLSA-N C(C1=CC=CC=C1)(=O)N1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1[C@H]1[C@@H](C1)C=1N=NN(C=1)C)C(=O)O Chemical compound C(C1=CC=CC=C1)(=O)N1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1[C@H]1[C@@H](C1)C=1N=NN(C=1)C)C(=O)O BBOYBMOHXVYOQO-JHRSTNGLSA-N 0.000 claims 1
- MEDSBFJBCIOQLG-UHFFFAOYSA-N C(CCC)C1C(CCC1)N(C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O)C Chemical compound C(CCC)C1C(CCC1)N(C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O)C MEDSBFJBCIOQLG-UHFFFAOYSA-N 0.000 claims 1
- TWQAVSOTCNJNPI-VCJXRDTASA-N C(CCC)C1CCC2=C1N(N=C2)[C@@H]1C[C@@H](CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O Chemical compound C(CCC)C1CCC2=C1N(N=C2)[C@@H]1C[C@@H](CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O TWQAVSOTCNJNPI-VCJXRDTASA-N 0.000 claims 1
- FDJILTHMPFRQLP-UHFFFAOYSA-N C(CCC)C1N(CCC1)C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1C(C1)C=1N=NN(C=1)C)C(=O)O Chemical compound C(CCC)C1N(CCC1)C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1C(C1)C=1N=NN(C=1)C)C(=O)O FDJILTHMPFRQLP-UHFFFAOYSA-N 0.000 claims 1
- UHBPMQISVQNVGD-UHFFFAOYSA-N C(CCC)C1N(CCC1)C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O Chemical compound C(CCC)C1N(CCC1)C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O UHBPMQISVQNVGD-UHFFFAOYSA-N 0.000 claims 1
- BHLAIZTUPSCZIY-UHFFFAOYSA-N C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CC1)N1N=CC=2C(CCCC1=2)=O)C(=O)O Chemical compound C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CC1)N1N=CC=2C(CCCC1=2)=O)C(=O)O BHLAIZTUPSCZIY-UHFFFAOYSA-N 0.000 claims 1
- USSQBFRLEKLNDG-UHFFFAOYSA-N C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1C(CCC1)(C)C)C(=O)O Chemical compound C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1C(CCC1)(C)C)C(=O)O USSQBFRLEKLNDG-UHFFFAOYSA-N 0.000 claims 1
- JBTWWYSZUSGGSN-UHFFFAOYSA-N C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1C(CCC1)C1CC1)C(=O)O Chemical compound C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1C(CCC1)C1CC1)C(=O)O JBTWWYSZUSGGSN-UHFFFAOYSA-N 0.000 claims 1
- WHGOYWJNESEHSK-UHFFFAOYSA-N C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1C(CCC1)CCC(C)C)C(=O)O Chemical compound C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1C(CCC1)CCC(C)C)C(=O)O WHGOYWJNESEHSK-UHFFFAOYSA-N 0.000 claims 1
- BDQZIUZHYGGIBI-UHFFFAOYSA-N C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1C(CCCC1)CCC)C(=O)O Chemical compound C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1C(CCCC1)CCC)C(=O)O BDQZIUZHYGGIBI-UHFFFAOYSA-N 0.000 claims 1
- YMMIPFNSMPECNL-UHFFFAOYSA-N C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1CC(CC1)C)C(=O)O Chemical compound C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1CC(CC1)C)C(=O)O YMMIPFNSMPECNL-UHFFFAOYSA-N 0.000 claims 1
- KFMAODZLDUERIC-UHFFFAOYSA-N C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1CCCCC1)C(=O)O Chemical compound C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(=O)N1CCCCC1)C(=O)O KFMAODZLDUERIC-UHFFFAOYSA-N 0.000 claims 1
- YNOQXOCLOKUMBJ-UHFFFAOYSA-N C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(N(C)C)=O)C(=O)O Chemical compound C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(N(C)C)=O)C(=O)O YNOQXOCLOKUMBJ-UHFFFAOYSA-N 0.000 claims 1
- SGKYDFFYFCZKOA-UHFFFAOYSA-N C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(N(C1C(CCCC1)CCC)C)=O)C(=O)O Chemical compound C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)C(N(C1C(CCCC1)CCC)C)=O)C(=O)O SGKYDFFYFCZKOA-UHFFFAOYSA-N 0.000 claims 1
- NJMKUBOTLNVCOM-UHFFFAOYSA-N C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)N1N=CC2=C1C(CC2)CCC)C(=O)O Chemical compound C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)N1N=CC2=C1C(CC2)CCC)C(=O)O NJMKUBOTLNVCOM-UHFFFAOYSA-N 0.000 claims 1
- RXFJSUFPIXZSOI-UHFFFAOYSA-N C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)N1N=CC=2CCCCC1=2)C(=O)O Chemical compound C1(CC1)C1=C(C=NN1C1=CC(=CC=C1)C1CC(CCC1)N1N=CC=2CCCCC1=2)C(=O)O RXFJSUFPIXZSOI-UHFFFAOYSA-N 0.000 claims 1
- NRFUDPGDMRYSAV-UHFFFAOYSA-N C1(CCC1)C1N(CCC1)C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O Chemical compound C1(CCC1)C1N(CCC1)C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O NRFUDPGDMRYSAV-UHFFFAOYSA-N 0.000 claims 1
- JUYLFSGIOZQLCJ-MXNGKVSJSA-N C1(CCCCC1)CC(=O)N1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1[C@H]1[C@@H](C1)C=1N=NN(C=1)C)C(=O)O Chemical compound C1(CCCCC1)CC(=O)N1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1[C@H]1[C@@H](C1)C=1N=NN(C=1)C)C(=O)O JUYLFSGIOZQLCJ-MXNGKVSJSA-N 0.000 claims 1
- IXVSSVHQMCWHCA-LYWQJQBASA-N C1(CCCCC1)CCC1CN(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1[C@H]1[C@@H](C1)C=1N=NN(C=1)C)C(=O)O Chemical compound C1(CCCCC1)CCC1CN(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1[C@H]1[C@@H](C1)C=1N=NN(C=1)C)C(=O)O IXVSSVHQMCWHCA-LYWQJQBASA-N 0.000 claims 1
- IXVSSVHQMCWHCA-FTBPSBKWSA-N C1(CCCCC1)CC[C@H]1CN(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1[C@H]1[C@@H](C1)C=1N=NN(C=1)C)C(=O)O Chemical compound C1(CCCCC1)CC[C@H]1CN(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1[C@H]1[C@@H](C1)C=1N=NN(C=1)C)C(=O)O IXVSSVHQMCWHCA-FTBPSBKWSA-N 0.000 claims 1
- IADJVLAWGPGNCJ-UHFFFAOYSA-N C1(CCCCC1)CN1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O Chemical compound C1(CCCCC1)CN1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O IADJVLAWGPGNCJ-UHFFFAOYSA-N 0.000 claims 1
- WBPOOOYATOSZSM-UHFFFAOYSA-N C1(CCCCC1)N(C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O)C Chemical compound C1(CCCCC1)N(C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O)C WBPOOOYATOSZSM-UHFFFAOYSA-N 0.000 claims 1
- WSOYZFTZHFKPSW-UHFFFAOYSA-N C1CCCC11CN(CCC1)C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O Chemical compound C1CCCC11CN(CCC1)C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O WSOYZFTZHFKPSW-UHFFFAOYSA-N 0.000 claims 1
- RVSCUMQTTMXEBD-QENMJEOYSA-N CN1N=NC(=C1)[C@H]1[C@@H](C1)C1=C(C=NN1C1=CC(=CC=C1)C1CN(CCC1)S(=O)(=O)C1=CC=CC=C1)C(=O)O Chemical compound CN1N=NC(=C1)[C@H]1[C@@H](C1)C1=C(C=NN1C1=CC(=CC=C1)C1CN(CCC1)S(=O)(=O)C1=CC=CC=C1)C(=O)O RVSCUMQTTMXEBD-QENMJEOYSA-N 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 206010072082 Environmental exposure Diseases 0.000 claims 1
- 206010073306 Exposure to radiation Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010019799 Hepatitis viral Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010062016 Immunosuppression Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- PNBDMYXQXUTMES-UHFFFAOYSA-N N1(CCCC11CCCCC1)C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O Chemical compound N1(CCCC11CCCCC1)C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O PNBDMYXQXUTMES-UHFFFAOYSA-N 0.000 claims 1
- IHYPHZWLSBZRCB-UHFFFAOYSA-N N1(CCCCCC1)C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O Chemical compound N1(CCCCCC1)C(=O)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O IHYPHZWLSBZRCB-UHFFFAOYSA-N 0.000 claims 1
- VCZUEFBCMVWXNK-UHFFFAOYSA-N N1(N=CC2=C1CCC2)C1CC(CC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O Chemical compound N1(N=CC2=C1CCC2)C1CC(CC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O VCZUEFBCMVWXNK-UHFFFAOYSA-N 0.000 claims 1
- QOLJFEMPDFFVBE-UHFFFAOYSA-N N1(N=CC2=C1CCCCC2)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O Chemical compound N1(N=CC2=C1CCCCC2)C1CC(CCC1)C=1C=C(C=CC=1)N1N=CC(=C1C1CC1)C(=O)O QOLJFEMPDFFVBE-UHFFFAOYSA-N 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims 1
- 206010062237 Renal impairment Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 241000282485 Vulpes vulpes Species 0.000 claims 1
- 208000024716 acute asthma Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 102000015395 alpha 1-Antitrypsin Human genes 0.000 claims 1
- 108010050122 alpha 1-Antitrypsin Proteins 0.000 claims 1
- 229940024142 alpha 1-antitrypsin Drugs 0.000 claims 1
- 208000008445 altitude sickness Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000023819 chronic asthma Diseases 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 230000007882 cirrhosis Effects 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 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 1
- 230000007850 degeneration Effects 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000003511 endothelial effect Effects 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 230000001506 immunosuppresive effect Effects 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 230000008518 non respiratory effect Effects 0.000 claims 1
- 229960005489 paracetamol Drugs 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 201000011461 pre-eclampsia Diseases 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
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| PCT/IB2016/055997 WO2017060855A1 (en) | 2015-10-06 | 2016-10-06 | Arylcyclohexyl pyrazoles as nrf2 regulators |
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| LT3307739T (lt) | 2015-06-15 | 2021-03-10 | Glaxosmithkline Intellectual Property Development Limited | Nrf2 reguliatoriai |
| WO2016203401A1 (en) | 2015-06-15 | 2016-12-22 | Glaxosmithkline Intellectual Property Development Limited | Nrf2 regulators |
| US10364256B2 (en) | 2015-10-06 | 2019-07-30 | Glaxosmithkline Intellectual Property Development Limited | Biaryl pyrazoles as NRF2 regulators |
| JP2020500918A (ja) * | 2016-12-12 | 2020-01-16 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | Ｎｒｆ２レギュレーターとしてのｎ−アリールピラゾール |
| JP2020500919A (ja) * | 2016-12-12 | 2020-01-16 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | Ｎｒｆ２レギュレーターとしての３−カルボン酸ピロール |
| EP3833662B1 (en) | 2018-08-20 | 2024-01-17 | Janssen Pharmaceutica NV | Inhibitors of keap1-nrf2 protein-protein interaction |
| MX2021006527A (es) | 2018-12-05 | 2021-07-21 | Scohia Pharma Inc | Compuesto macrociclico y su uso. |
| AU2020283361B2 (en) | 2019-05-31 | 2025-11-27 | Ube Corporation | Benzotriazole derivative |
| WO2024015761A2 (en) * | 2022-07-11 | 2024-01-18 | Rutgers, The State University Of New Jersey | Gαlpha12 inhibitors and methods using same |
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| GB2064336B (en) | 1979-12-06 | 1984-03-14 | Glaxo Group Ltd | Device for dispensing medicaments |
| DE3274065D1 (de) | 1981-07-08 | 1986-12-11 | Draco Ab | Powder inhalator |
| DK172541B1 (da) | 1982-10-08 | 1998-12-07 | Glaxo Group Ltd | Apparat til administrering af medikamenter til patienter og en medikamentpakning til brug i apparatet |
| GB2169265B (en) | 1982-10-08 | 1987-08-12 | Glaxo Group Ltd | Pack for medicament |
| US4778054A (en) | 1982-10-08 | 1988-10-18 | Glaxo Group Limited | Pack for administering medicaments to patients |
| DE3682457D1 (de) | 1985-07-30 | 1991-12-19 | Glaxo Group Ltd | Geraet zur verabreichung von medikamenten an patienten. |
| US6536427B2 (en) | 1990-03-02 | 2003-03-25 | Glaxo Group Limited | Inhalation device |
| SK280968B6 (sk) | 1990-03-02 | 2000-10-09 | Glaxo Group Limited | Balenie medikamentu na použite v inhalačnom prístroji |
| GB9004781D0 (en) | 1990-03-02 | 1990-04-25 | Glaxo Group Ltd | Device |
| GB9700226D0 (en) | 1997-01-08 | 1997-02-26 | Glaxo Group Ltd | Inhalation device |
| GB0201677D0 (en) | 2002-01-25 | 2002-03-13 | Glaxo Group Ltd | Medicament dispenser |
| JP2006522130A (ja) * | 2003-04-03 | 2006-09-28 | メルク エンド カムパニー インコーポレーテッド | ナトリウムチャンネル遮断薬としてのビアリール置換ピラゾール |
| GB0317374D0 (en) | 2003-07-24 | 2003-08-27 | Glaxo Group Ltd | Medicament dispenser |
| DK1730676T3 (da) | 2004-02-16 | 2013-11-04 | Glaxo Group Ltd | Tælleenhed til anvendelse med en medikamentfordeler |
| GB0418278D0 (en) | 2004-08-16 | 2004-09-15 | Glaxo Group Ltd | Medicament dispenser |
| GB0515584D0 (en) | 2005-07-28 | 2005-09-07 | Glaxo Group Ltd | Medicament dispenser |
| AR058289A1 (es) | 2005-12-12 | 2008-01-30 | Glaxo Group Ltd | Colector para ser usado en dispensador de medicamento |
| KR20100059952A (ko) * | 2007-09-06 | 2010-06-04 | 머크 샤프 앤드 돔 코포레이션 | 가용성 구아닐레이트 사이클라제 활성제 |
| CN102414194A (zh) * | 2009-02-26 | 2012-04-11 | 默沙东公司 | 可溶性鸟苷酸环化酶激活剂 |
| SG11201604611SA (en) * | 2013-12-18 | 2016-07-28 | Glaxosmithkline Ip Dev Ltd | Nrf2 regulators |
| TW201625586A (zh) * | 2014-07-02 | 2016-07-16 | 諾華公司 | 環己烯－１－基－吡啶－２－基－１ｈ－吡唑－４－羧酸衍生物及其作為可溶性鳥苷酸環化酶活化劑之用途 |
| TW201625601A (zh) | 2014-07-02 | 2016-07-16 | 諾華公司 | 噻吩－２－基－吡啶－２－基－１ｈ－吡唑－４－羧酸衍生物及其作為可溶性鳥苷酸環化酶活化劑之用途 |
| LT3307739T (lt) * | 2015-06-15 | 2021-03-10 | Glaxosmithkline Intellectual Property Development Limited | Nrf2 reguliatoriai |
| WO2016203401A1 (en) * | 2015-06-15 | 2016-12-22 | Glaxosmithkline Intellectual Property Development Limited | Nrf2 regulators |
| CA2988373A1 (en) * | 2015-06-15 | 2016-12-22 | Glaxosmithkline Intellectual Property Development Limited | Nrf2 regulators |
| US10364256B2 (en) * | 2015-10-06 | 2019-07-30 | Glaxosmithkline Intellectual Property Development Limited | Biaryl pyrazoles as NRF2 regulators |
-
2016
- 2016-10-06 US US15/765,377 patent/US10351530B2/en not_active Expired - Fee Related
- 2016-10-06 WO PCT/IB2016/055997 patent/WO2017060855A1/en not_active Ceased
- 2016-10-06 JP JP2018517526A patent/JP2018529744A/ja active Pending
- 2016-10-06 EP EP16784575.9A patent/EP3371167A1/en not_active Withdrawn
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