JP2010523499A5 - - Google Patents

Info

Publication number

JP2010523499A5

JP2010523499A5 JP2010501256A JP2010501256A JP2010523499A5 JP 2010523499 A5 JP2010523499 A5 JP 2010523499A5 JP 2010501256 A JP2010501256 A JP 2010501256A JP 2010501256 A JP2010501256 A JP 2010501256A JP 2010523499 A5 JP2010523499 A5 JP 2010523499A5

Authority

JP

Japan

Prior art keywords

carboxylic acid

group

hydroxy

cyclopropyl

quinoline

Prior art date

2008-03-28

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.)

Withdrawn

Links

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• 150000001875 compounds Chemical class 0.000 claims description 312
• 125000000217 alkyl group Chemical group 0.000 claims description 156
• -1 wherein R 9 Chemical compound 0.000 claims description 142
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 128
• 150000003839 salts Chemical class 0.000 claims description 112
• 150000002148 esters Chemical class 0.000 claims description 102
• 239000000203 mixture Substances 0.000 claims description 95
• 125000003118 aryl group Chemical group 0.000 claims description 83
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 70
• 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 67
• 125000000304 alkynyl group Chemical group 0.000 claims description 56
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 51
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 47
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 44
• 125000001072 heteroaryl group Chemical group 0.000 claims description 39
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 34
• 201000010099 disease Diseases 0.000 claims description 28
• 102000003800 Selectins Human genes 0.000 claims description 27
• 108090000184 Selectins Proteins 0.000 claims description 27
• 125000003342 alkenyl group Chemical group 0.000 claims description 27
• 150000001721 carbon Chemical group 0.000 claims description 27
• 229910052799 carbon Inorganic materials 0.000 claims description 27
• 125000004432 carbon atom Chemical group C* 0.000 claims description 23
• 208000035475 disorder Diseases 0.000 claims description 23
• 241000124008 Mammalia Species 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 19
• VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 claims description 19
• 238000011282 treatment Methods 0.000 claims description 19
• 239000002253 acid Substances 0.000 claims description 16
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
• 208000011580 syndromic disease Diseases 0.000 claims description 16
• 125000001188 haloalkyl group Chemical group 0.000 claims description 14
• AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 claims description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 210000004027 cell Anatomy 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 230000001404 mediated effect Effects 0.000 claims description 13
• 210000000265 leukocyte Anatomy 0.000 claims description 12
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 210000000056 organ Anatomy 0.000 claims description 9
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
• 208000023275 Autoimmune disease Diseases 0.000 claims description 8
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 8
• 206010027476 Metastases Diseases 0.000 claims description 8
• 201000004681 Psoriasis Diseases 0.000 claims description 8
• 230000000694 effects Effects 0.000 claims description 8
• 150000004677 hydrates Chemical class 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
• 206010002388 Angina unstable Diseases 0.000 claims description 7
• 208000023328 Basedow disease Diseases 0.000 claims description 7
• 206010051055 Deep vein thrombosis Diseases 0.000 claims description 7
• 208000015023 Graves' disease Diseases 0.000 claims description 7
• 206010019280 Heart failures Diseases 0.000 claims description 7
• 206010028980 Neoplasm Diseases 0.000 claims description 7
• 208000018262 Peripheral vascular disease Diseases 0.000 claims description 7
• 206010048591 Post thrombotic syndrome Diseases 0.000 claims description 7
• 208000007536 Thrombosis Diseases 0.000 claims description 7
• 208000032109 Transient ischaemic attack Diseases 0.000 claims description 7
• 208000007814 Unstable Angina Diseases 0.000 claims description 7
• 206010047249 Venous thrombosis Diseases 0.000 claims description 7
• 201000011510 cancer Diseases 0.000 claims description 7
• 208000007565 gingivitis Diseases 0.000 claims description 7
• 210000003714 granulocyte Anatomy 0.000 claims description 7
• 238000001631 haemodialysis Methods 0.000 claims description 7
• 230000000322 hemodialysis Effects 0.000 claims description 7
• 208000014674 injury Diseases 0.000 claims description 7
• 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 7
• 230000009401 metastasis Effects 0.000 claims description 7
• 201000006417 multiple sclerosis Diseases 0.000 claims description 7
• 201000001245 periodontitis Diseases 0.000 claims description 7
• 208000007056 sickle cell anemia Diseases 0.000 claims description 7
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 7
• 206010043778 thyroiditis Diseases 0.000 claims description 7
• 201000010875 transient cerebral ischemia Diseases 0.000 claims description 7
• 208000027930 type IV hypersensitivity disease Diseases 0.000 claims description 7
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
• 201000001320 Atherosclerosis Diseases 0.000 claims description 6
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 6
• 208000011231 Crohn disease Diseases 0.000 claims description 6
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 6
• 108090000695 Cytokines Proteins 0.000 claims description 6
• 102000004127 Cytokines Human genes 0.000 claims description 6
• 206010014561 Emphysema Diseases 0.000 claims description 6
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 6
• 208000032759 Hemolytic-Uremic Syndrome Diseases 0.000 claims description 6
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 6
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
• 206010051606 Necrotising colitis Diseases 0.000 claims description 6
• 206010058105 Neutrophilic dermatosis Diseases 0.000 claims description 6
• 206010035664 Pneumonia Diseases 0.000 claims description 6
• 208000003782 Raynaud disease Diseases 0.000 claims description 6
• 208000012322 Raynaud phenomenon Diseases 0.000 claims description 6
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 6
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 6
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 6
• 235000009508 confectionery Nutrition 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 6
• 208000028867 ischemia Diseases 0.000 claims description 6
• 208000010125 myocardial infarction Diseases 0.000 claims description 6
• 208000004995 necrotizing enterocolitis Diseases 0.000 claims description 6
• 201000006195 perinatal necrotizing enterocolitis Diseases 0.000 claims description 6
• 208000037803 restenosis Diseases 0.000 claims description 6
• 230000008733 trauma Effects 0.000 claims description 6
• PPHSJAKBSFBRHC-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3,6-dihydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(O)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 PPHSJAKBSFBRHC-UHFFFAOYSA-N 0.000 claims description 5
• UJSGGWGSBUIARQ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6,8-dimethylquinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(C)=CC(C)=C2N=C1C1(C=2C=CC(Cl)=CC=2)CC1 UJSGGWGSBUIARQ-UHFFFAOYSA-N 0.000 claims description 5
• 206010003178 Arterial thrombosis Diseases 0.000 claims description 5
• 230000007214 atherothrombosis Effects 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 208000037890 multiple organ injury Diseases 0.000 claims description 5
• 201000008482 osteoarthritis Diseases 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 230000002265 prevention Effects 0.000 claims description 5
• 230000001988 toxicity Effects 0.000 claims description 5
• 231100000419 toxicity Toxicity 0.000 claims description 5
• QCGSEAKBCHBTKS-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6,8-bis(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=C(C(F)(F)F)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 QCGSEAKBCHBTKS-UHFFFAOYSA-N 0.000 claims description 4
• VZFQHPLEOOFYOH-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 VZFQHPLEOOFYOH-UHFFFAOYSA-N 0.000 claims description 4
• 206010039705 Scleritis Diseases 0.000 claims description 4
• 206010052779 Transplant rejections Diseases 0.000 claims description 4
• 230000010410 reperfusion Effects 0.000 claims description 4
• 208000024891 symptom Diseases 0.000 claims description 4
• BHRSRGUVJGTOBA-UHFFFAOYSA-N 2-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(C(F)(F)F)=NC2=C1 BHRSRGUVJGTOBA-UHFFFAOYSA-N 0.000 claims description 3
• JGSWEULRSNETKL-UHFFFAOYSA-N 2-[1-(2-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C(=CC=CC=2)Cl)CC1 JGSWEULRSNETKL-UHFFFAOYSA-N 0.000 claims description 3
• RZKOUEJUNBPRAT-UHFFFAOYSA-N 2-[1-(3-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=C(Cl)C=CC=2)CC1 RZKOUEJUNBPRAT-UHFFFAOYSA-N 0.000 claims description 3
• GCNAFZVEBJYFGK-UHFFFAOYSA-N 2-[1-(4-bromophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Br)=CC=2)CC1 GCNAFZVEBJYFGK-UHFFFAOYSA-N 0.000 claims description 3
• MLVASRCEOCFBAD-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclobutyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CCC1 MLVASRCEOCFBAD-UHFFFAOYSA-N 0.000 claims description 3
• SSRSFFBJNGTART-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6-(trifluoromethoxy)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(OC(F)(F)F)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 SSRSFFBJNGTART-UHFFFAOYSA-N 0.000 claims description 3
• ZDMKJBNVEQUZJB-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(C(F)(F)F)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 ZDMKJBNVEQUZJB-UHFFFAOYSA-N 0.000 claims description 3
• OFXKYYRRMSAALR-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6-methyl-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(C)=CC(C(F)(F)F)=C2N=C1C1(C=2C=CC(Cl)=CC=2)CC1 OFXKYYRRMSAALR-UHFFFAOYSA-N 0.000 claims description 3
• IRGQKCRMKVVJIZ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6-methylquinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(C)=CC=C2N=C1C1(C=2C=CC(Cl)=CC=2)CC1 IRGQKCRMKVVJIZ-UHFFFAOYSA-N 0.000 claims description 3
• LVACEZHKXJVGAN-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6-phenyl-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound C1=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC(Cl)=CC=3)=NC2=C(C(F)(F)F)C=C1C1=CC=CC=C1 LVACEZHKXJVGAN-UHFFFAOYSA-N 0.000 claims description 3
• DPVQYMWEZYNTPN-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6-propan-2-ylquinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(C(C)C)=CC=C2N=C1C1(C=2C=CC(Cl)=CC=2)CC1 DPVQYMWEZYNTPN-UHFFFAOYSA-N 0.000 claims description 3
• PFIBJPOPGOFTTQ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic acid Chemical compound N=1C2=C3CCCCC3=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 PFIBJPOPGOFTTQ-UHFFFAOYSA-N 0.000 claims description 3
• CVBBIOBLWGAMGU-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-7-methylquinoline-4-carboxylic acid Chemical compound N=1C2=CC(C)=CC=C2C(C(O)=O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 CVBBIOBLWGAMGU-UHFFFAOYSA-N 0.000 claims description 3
• NTWQKNZXCYEXEU-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethoxy)quinoline-4-carboxylic acid Chemical compound N=1C2=C(OC(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 NTWQKNZXCYEXEU-UHFFFAOYSA-N 0.000 claims description 3
• RACDNEQBIMTJPQ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 RACDNEQBIMTJPQ-UHFFFAOYSA-N 0.000 claims description 3
• DSNCNEJAJMSDCP-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-methyl-6-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N1=C2C(C)=CC(C(F)(F)F)=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(Cl)=CC=2)CC1 DSNCNEJAJMSDCP-UHFFFAOYSA-N 0.000 claims description 3
• IVYQOEVAWKULEU-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-methylquinoline-4-carboxylic acid Chemical compound N1=C2C(C)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(Cl)=CC=2)CC1 IVYQOEVAWKULEU-UHFFFAOYSA-N 0.000 claims description 3
• KQGVNGRQALHSRT-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-propan-2-ylquinoline-4-carboxylic acid Chemical compound N1=C2C(C(C)C)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(Cl)=CC=2)CC1 KQGVNGRQALHSRT-UHFFFAOYSA-N 0.000 claims description 3
• HFFQHHJHEKTNOD-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxyquinoline-4,8-dicarboxylic acid Chemical compound N1=C2C(C(=O)O)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(Cl)=CC=2)CC1 HFFQHHJHEKTNOD-UHFFFAOYSA-N 0.000 claims description 3
• IWVVLMAAJRPMKY-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-6-ethyl-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(CC)=CC(C(F)(F)F)=C2N=C1C1(C=2C=CC(Cl)=CC=2)CC1 IWVVLMAAJRPMKY-UHFFFAOYSA-N 0.000 claims description 3
• URDILIYTWGPYKJ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-6-fluoro-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(F)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 URDILIYTWGPYKJ-UHFFFAOYSA-N 0.000 claims description 3
• RYHAEGXAXZNHAF-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-7-ethyl-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC(CC)=CC=C2C(C(O)=O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 RYHAEGXAXZNHAF-UHFFFAOYSA-N 0.000 claims description 3
• XWNWOISRVSYKKL-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-8-cyclopropyl-3-hydroxyquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC(Cl)=CC=3)=NC2=C1C1CC1 XWNWOISRVSYKKL-UHFFFAOYSA-N 0.000 claims description 3
• SADKPEGBHCTYOJ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-8-ethyl-3-hydroxy-6-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N1=C2C(CC)=CC(C(F)(F)F)=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(Cl)=CC=2)CC1 SADKPEGBHCTYOJ-UHFFFAOYSA-N 0.000 claims description 3
• ULTHLRANTPUCEP-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-8-ethyl-3-hydroxyquinoline-4-carboxylic acid Chemical compound N1=C2C(CC)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(Cl)=CC=2)CC1 ULTHLRANTPUCEP-UHFFFAOYSA-N 0.000 claims description 3
• GHNXHPIDYMKKOI-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-6,8-dimethylquinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(C)=CC(C)=C2N=C1C1(C=2C=CC(F)=CC=2)CC1 GHNXHPIDYMKKOI-UHFFFAOYSA-N 0.000 claims description 3
• CQVVFEIRAFOBNR-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic acid Chemical compound N=1C2=C3CCCCC3=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(F)=CC=2)CC1 CQVVFEIRAFOBNR-UHFFFAOYSA-N 0.000 claims description 3
• XXXBUGUDABVJAQ-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-7,8-dimethylquinoline-4-carboxylic acid Chemical compound N=1C2=C(C)C(C)=CC=C2C(C(O)=O)=C(O)C=1C1(C=2C=CC(F)=CC=2)CC1 XXXBUGUDABVJAQ-UHFFFAOYSA-N 0.000 claims description 3
• MINNPGUXARJKMX-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(F)=CC=2)CC1 MINNPGUXARJKMX-UHFFFAOYSA-N 0.000 claims description 3
• VEWHRKWTVOQXGW-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-8-methylquinoline-4-carboxylic acid Chemical compound N1=C2C(C)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(F)=CC=2)CC1 VEWHRKWTVOQXGW-UHFFFAOYSA-N 0.000 claims description 3
• YVRANBPIBKYHJI-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-8-phenylquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC(F)=CC=3)=NC2=C1C1=CC=CC=C1 YVRANBPIBKYHJI-UHFFFAOYSA-N 0.000 claims description 3
• AUBXSTRGUCAKQJ-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-8-propan-2-ylquinoline-4-carboxylic acid Chemical compound N1=C2C(C(C)C)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(F)=CC=2)CC1 AUBXSTRGUCAKQJ-UHFFFAOYSA-N 0.000 claims description 3
• OXXAEHOANATEMJ-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-8-thiophen-3-ylquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC(F)=CC=3)=NC2=C1C=1C=CSC=1 OXXAEHOANATEMJ-UHFFFAOYSA-N 0.000 claims description 3
• XFZAQDNDHUIIJG-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)propan-2-yl]-3-hydroxy-7,8-dimethylquinoline-4-carboxylic acid Chemical compound N=1C2=C(C)C(C)=CC=C2C(C(O)=O)=C(O)C=1C(C)(C)C1=CC=C(Cl)C=C1 XFZAQDNDHUIIJG-UHFFFAOYSA-N 0.000 claims description 3
• KAUONQSAQQAYOC-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)propan-2-yl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(O)=O)=C(O)C=1C(C)(C)C1=CC=C(Cl)C=C1 KAUONQSAQQAYOC-UHFFFAOYSA-N 0.000 claims description 3
• PAOZFKVRYUJFGX-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)propan-2-yl]-3-hydroxy-8-propan-2-ylquinoline-4-carboxylic acid Chemical compound N1=C2C(C(C)C)=CC=CC2=C(C(O)=O)C(O)=C1C(C)(C)C1=CC=C(Cl)C=C1 PAOZFKVRYUJFGX-UHFFFAOYSA-N 0.000 claims description 3
• RHFOZYDMSOPOTF-UHFFFAOYSA-N 3-hydroxy-2-(1-phenylcyclopropyl)-6-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(C(F)(F)F)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC=CC=2)CC1 RHFOZYDMSOPOTF-UHFFFAOYSA-N 0.000 claims description 3
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