JP2010523499A5

JP2010523499A5 -

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Publication number: JP2010523499A5
Authority: JP; Japan
Prior art keywords: carboxylic acid; group; hydroxy; cyclopropyl; quinoline
Prior art date: 2008-03-28
Legal status : Withdrawn

Application number

JP2010501256A

Other languages

English (en)

Japanese (ja)

Other versions

JP2010523499A (ja

Filing date

2008-03-28

Publication date

2012-01-26

2008-03-28 Application filed filed Critical

2008-03-28 Priority claimed from PCT/US2008/058654 external-priority patent/WO2008121817A2/en

2010-07-15 Publication of JP2010523499A publication Critical patent/JP2010523499A/ja

2012-01-26 Publication of JP2010523499A5 publication Critical patent/JP2010523499A5/ja

Status Withdrawn legal-status Critical Current

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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
IOOAVNABRMYUPR-UHFFFAOYSA-N 3-hydroxy-2-(1-phenylcyclopropyl)-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=CC=2)CC1 IOOAVNABRMYUPR-UHFFFAOYSA-N 0.000 claims description 3
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JP2010501256A 2007-03-30 2008-03-28 セレクチンの阻害のための方法および組成物 Withdrawn JP2010523499A (ja)