KR20090127183A - 퀴놀린 유도체, 및 이를 포함하는 셀렉틴 억제용 제약 조성물 - Google Patents
퀴놀린 유도체, 및 이를 포함하는 셀렉틴 억제용 제약 조성물 Download PDFInfo
- Publication number
- KR20090127183A KR20090127183A KR1020097022659A KR20097022659A KR20090127183A KR 20090127183 A KR20090127183 A KR 20090127183A KR 1020097022659 A KR1020097022659 A KR 1020097022659A KR 20097022659 A KR20097022659 A KR 20097022659A KR 20090127183 A KR20090127183 A KR 20090127183A
- Authority
- KR
- South Korea
- Prior art keywords
- carboxylic acid
- hydroxy
- cyclopropyl
- quinoline
- group
- 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.)
- Withdrawn
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- 102000003800 Selectins Human genes 0.000 title claims abstract description 24
- 108090000184 Selectins Proteins 0.000 title claims abstract description 24
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 230000002401 inhibitory effect Effects 0.000 title description 4
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 266
- 150000001875 compounds Chemical class 0.000 claims abstract description 251
- 230000001404 mediated effect Effects 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 119
- -1 hydrate Chemical class 0.000 claims description 103
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 102
- 125000001072 heteroaryl group Chemical group 0.000 claims description 74
- 150000003839 salts Chemical class 0.000 claims description 65
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 62
- 150000002148 esters Chemical class 0.000 claims description 59
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 43
- 125000000304 alkynyl group Chemical group 0.000 claims description 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 41
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 238000011282 treatment Methods 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 23
- 150000004677 hydrates Chemical class 0.000 claims description 22
- 241000124008 Mammalia Species 0.000 claims description 18
- 150000001721 carbon Chemical group 0.000 claims description 18
- 208000035475 disorder Diseases 0.000 claims description 18
- 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
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 208000014674 injury Diseases 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- 230000003834 intracellular effect Effects 0.000 claims description 7
- 210000000056 organ Anatomy 0.000 claims description 7
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 6
- 206010027476 Metastases Diseases 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 230000009401 metastasis Effects 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- 206010002388 Angina unstable Diseases 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 208000003807 Graves Disease Diseases 0.000 claims description 5
- 208000015023 Graves' disease Diseases 0.000 claims description 5
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 208000032759 Hemolytic-Uremic Syndrome Diseases 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 5
- 208000007536 Thrombosis Diseases 0.000 claims description 5
- 208000007814 Unstable Angina Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 208000007565 gingivitis Diseases 0.000 claims description 5
- 210000003714 granulocyte Anatomy 0.000 claims description 5
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 5
- 230000000302 ischemic effect Effects 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 210000000440 neutrophil Anatomy 0.000 claims description 5
- 201000001245 periodontitis Diseases 0.000 claims description 5
- 208000007056 sickle cell anemia Diseases 0.000 claims description 5
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 5
- 208000027930 type IV hypersensitivity disease Diseases 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 4
- 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 4
- 108090000695 Cytokines Proteins 0.000 claims description 4
- 102000004127 Cytokines Human genes 0.000 claims description 4
- 206010051055 Deep vein thrombosis Diseases 0.000 claims description 4
- 206010014561 Emphysema Diseases 0.000 claims description 4
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 4
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims description 4
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 206010035664 Pneumonia Diseases 0.000 claims description 4
- 206010048591 Post thrombotic syndrome Diseases 0.000 claims description 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 208000032109 Transient ischaemic attack Diseases 0.000 claims description 4
- 206010052779 Transplant rejections Diseases 0.000 claims description 4
- 206010053613 Type IV hypersensitivity reaction Diseases 0.000 claims description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
- 206010047249 Venous thrombosis Diseases 0.000 claims description 4
- 208000027418 Wounds and injury Diseases 0.000 claims description 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 235000009508 confectionery Nutrition 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 238000001631 haemodialysis Methods 0.000 claims description 4
- 230000000322 hemodialysis Effects 0.000 claims description 4
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 4
- 208000010125 myocardial infarction Diseases 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 230000010410 reperfusion Effects 0.000 claims description 4
- 208000037803 restenosis Diseases 0.000 claims description 4
- 208000017520 skin disease Diseases 0.000 claims description 4
- 230000001988 toxicity Effects 0.000 claims description 4
- 231100000419 toxicity Toxicity 0.000 claims description 4
- 201000010875 transient cerebral ischemia Diseases 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- 230000005951 type IV hypersensitivity Effects 0.000 claims description 4
- 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 3
- 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 3
- UJSGGWGSBUIARQ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6,8-dimethylquinoline-4-carboxylic acid Chemical class 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 3
- 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 3
- 206010003178 Arterial thrombosis Diseases 0.000 claims description 3
- 206010048768 Dermatosis Diseases 0.000 claims description 3
- 230000007214 atherothrombosis Effects 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- PEIUJELXZAADQK-UHFFFAOYSA-N 2-(1-benzylcyclopropyl)-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(CC=2C=CC=CC=2)CC1 PEIUJELXZAADQK-UHFFFAOYSA-N 0.000 claims description 2
- HVZPZCUDANLJKA-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-3-(morpholine-4-carbonyloxy)-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic acid Chemical class C=1C=C(Cl)C=CC=1CC1=NC2=C3CCCCC3=CC=C2C(C(=O)O)=C1OC(=O)N1CCOCC1 HVZPZCUDANLJKA-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- FUHSQIQHVOBKIJ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-7,8-dimethylquinoline-4-carboxylic acid Chemical class N=1C2=C(C)C(C)=CC=C2C(C(O)=O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 FUHSQIQHVOBKIJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- IFQLLHTYMVUKBN-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-phenyl-6-(trifluoromethyl)quinoline-4-carboxylic acid Chemical class C1=C(C(F)(F)F)C=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC(Cl)=CC=3)=NC2=C1C1=CC=CC=C1 IFQLLHTYMVUKBN-UHFFFAOYSA-N 0.000 claims description 2
- AOSPHMYVAFMXLB-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-phenylquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC(Cl)=CC=3)=NC2=C1C1=CC=CC=C1 AOSPHMYVAFMXLB-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- XAFZGDJJCFQQPF-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)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(Cl)=CC=3)=NC2=C1C=1C=CSC=1 XAFZGDJJCFQQPF-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- QODXCZMKVRXXDD-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-8-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=C(C(O)(C(F)(F)F)C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 QODXCZMKVRXXDD-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
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- BKICHBVPINNNHC-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)ethyl]-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=1C(C)C1=CC=C(Cl)C=C1 BKICHBVPINNNHC-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- MFNPLSQDVZJJAG-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-6-methoxyquinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(OC)=CC=C2N=C1C1(C=2C=CC(F)=CC=2)CC1 MFNPLSQDVZJJAG-UHFFFAOYSA-N 0.000 claims description 2
- CQVVFEIRAFOBNR-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic acid Chemical class 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 2
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- 210000004881 tumor cell Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 208000004043 venous thromboembolism Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 210000004269 weibel-palade body Anatomy 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- LCPVHNNFHPWFCI-UHFFFAOYSA-M zinc;ethylbenzene;bromide Chemical compound Br[Zn+].C[CH-]C1=CC=CC=C1 LCPVHNNFHPWFCI-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
- C07D221/12—Phenanthridines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Vascular Medicine (AREA)
- Oncology (AREA)
- Transplantation (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92120307P | 2007-03-30 | 2007-03-30 | |
| US60/921,203 | 2007-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20090127183A true KR20090127183A (ko) | 2009-12-09 |
Family
ID=39730664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020097022659A Withdrawn KR20090127183A (ko) | 2007-03-30 | 2008-03-28 | 퀴놀린 유도체, 및 이를 포함하는 셀렉틴 억제용 제약 조성물 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20080255192A1 (enExample) |
| EP (1) | EP2134692A2 (enExample) |
| JP (1) | JP2010523499A (enExample) |
| KR (1) | KR20090127183A (enExample) |
| CN (1) | CN101646652A (enExample) |
| AU (1) | AU2008232683A1 (enExample) |
| BR (1) | BRPI0809509A2 (enExample) |
| CA (1) | CA2681757A1 (enExample) |
| MX (1) | MX2009010384A (enExample) |
| WO (1) | WO2008121817A2 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007516237A (ja) * | 2003-11-10 | 2007-06-21 | ワイス | セレクチン阻害のための方法および組成物 |
| US11021427B2 (en) | 2018-04-19 | 2021-06-01 | The Scripps Research Institute | Pd(II)-catalyzed enantioselective C—H arylation of free carboxylic acids |
| JP7129394B2 (ja) * | 2019-10-16 | 2022-09-01 | 信越化学工業株式会社 | 2-(1,2,2-トリメチル-3-シクロペンテニル)-2-オキソエチル=カルボキシレート化合物及びヒドロキシメチル=1,2,2-トリメチル-3-シクロペンテニル=ケトンの製造方法、並びにハロメチル=(1,2,2-トリメチル-3-シクロペンテニル)=ケトン化合物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5843707A (en) * | 1992-10-23 | 1998-12-01 | Genetics Institute, Inc. | Nucleic acid encoding a novel P-selectin ligand protein |
| JP2007516237A (ja) * | 2003-11-10 | 2007-06-21 | ワイス | セレクチン阻害のための方法および組成物 |
| EP1682511A2 (en) * | 2003-11-10 | 2006-07-26 | Wyeth | Methods and compositions for selectin inhibition |
| TW200738639A (en) * | 2005-10-05 | 2007-10-16 | Wyeth Corp | Process for the synthesis of compounds for selectin inhibition |
-
2008
- 2008-03-28 WO PCT/US2008/058654 patent/WO2008121817A2/en not_active Ceased
- 2008-03-28 BR BRPI0809509-4A patent/BRPI0809509A2/pt not_active Application Discontinuation
- 2008-03-28 EP EP08799715A patent/EP2134692A2/en not_active Withdrawn
- 2008-03-28 CN CN200880010474A patent/CN101646652A/zh active Pending
- 2008-03-28 JP JP2010501256A patent/JP2010523499A/ja not_active Withdrawn
- 2008-03-28 US US12/058,326 patent/US20080255192A1/en not_active Abandoned
- 2008-03-28 CA CA002681757A patent/CA2681757A1/en not_active Abandoned
- 2008-03-28 AU AU2008232683A patent/AU2008232683A1/en not_active Abandoned
- 2008-03-28 KR KR1020097022659A patent/KR20090127183A/ko not_active Withdrawn
- 2008-03-28 MX MX2009010384A patent/MX2009010384A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2008232683A1 (en) | 2008-10-09 |
| WO2008121817A3 (en) | 2009-02-12 |
| MX2009010384A (es) | 2009-10-16 |
| US20080255192A1 (en) | 2008-10-16 |
| CN101646652A (zh) | 2010-02-10 |
| JP2010523499A (ja) | 2010-07-15 |
| WO2008121817A2 (en) | 2008-10-09 |
| BRPI0809509A2 (pt) | 2014-09-16 |
| EP2134692A2 (en) | 2009-12-23 |
| CA2681757A1 (en) | 2008-10-09 |
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Patent event date: 20091029 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |