JP2010501587A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010501587A5 JP2010501587A5 JP2009525728A JP2009525728A JP2010501587A5 JP 2010501587 A5 JP2010501587 A5 JP 2010501587A5 JP 2009525728 A JP2009525728 A JP 2009525728A JP 2009525728 A JP2009525728 A JP 2009525728A JP 2010501587 A5 JP2010501587 A5 JP 2010501587A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- phenoxy
- acetic acid
- methyl
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 1,2,3,4-tetrahydronaphthyl Chemical group 0.000 claims description 92
- 150000001875 compounds Chemical class 0.000 claims description 89
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 208000026278 immune system disease Diseases 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 108010016626 Dipeptides Chemical group 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 150000001413 amino acids Chemical group 0.000 claims description 4
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- LFLSATHZMYYIAQ-UHFFFAOYSA-N 4-flourobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(F)C=C1 LFLSATHZMYYIAQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 208000000094 Chronic Pain Diseases 0.000 claims description 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- 206010010741 Conjunctivitis Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 201000004624 Dermatitis Diseases 0.000 claims description 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 2
- 208000010201 Exanthema Diseases 0.000 claims description 2
- 206010016654 Fibrosis Diseases 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- 206010028735 Nasal congestion Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010037660 Pyrexia Diseases 0.000 claims description 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 2
- 206010040047 Sepsis Diseases 0.000 claims description 2
- 208000007536 Thrombosis Diseases 0.000 claims description 2
- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 206010052568 Urticaria chronic Diseases 0.000 claims description 2
- 208000036142 Viral infection Diseases 0.000 claims description 2
- 125000006383 alkylpyridyl group Chemical group 0.000 claims description 2
- 201000010105 allergic rhinitis Diseases 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 201000008937 atopic dermatitis Diseases 0.000 claims description 2
- 208000010668 atopic eczema Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 201000005547 chronic conjunctivitis Diseases 0.000 claims description 2
- 208000037976 chronic inflammation Diseases 0.000 claims description 2
- 208000024376 chronic urticaria Diseases 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 201000005884 exanthem Diseases 0.000 claims description 2
- 230000004761 fibrosis Effects 0.000 claims description 2
- 238000011010 flushing procedure Methods 0.000 claims description 2
- 150000004820 halides Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 2
- 230000004968 inflammatory condition Effects 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 206010037844 rash Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 230000009385 viral infection Effects 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 3
- SUVXKBPDKSACKX-UHFFFAOYSA-N 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 SUVXKBPDKSACKX-UHFFFAOYSA-N 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- XVQDYPCNGOHWRO-UHFFFAOYSA-N 2-[3-(acetamidomethyl)-4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]phenyl]acetic acid Chemical compound CC(=O)NCC1=CC(CC(O)=O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 XVQDYPCNGOHWRO-UHFFFAOYSA-N 0.000 claims 1
- UOKSQLHHEOQAPZ-UHFFFAOYSA-N 2-[3-(methanesulfonamidomethyl)-4-[4-(2-phenylethylcarbamoyl)phenoxy]phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC=CC=2)C=C1 UOKSQLHHEOQAPZ-UHFFFAOYSA-N 0.000 claims 1
- HCMUIRXYFFKCSZ-UHFFFAOYSA-N 2-[3-(methanesulfonamidomethyl)-4-[4-(naphthalen-2-ylcarbamoyl)phenoxy]phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NC=2C=C3C=CC=CC3=CC=2)C=C1 HCMUIRXYFFKCSZ-UHFFFAOYSA-N 0.000 claims 1
- FRJYUTCPJMAZSA-UHFFFAOYSA-N 2-[3-(methanesulfonamidomethyl)-4-[4-(phenylcarbamoyl)phenoxy]phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1 FRJYUTCPJMAZSA-UHFFFAOYSA-N 0.000 claims 1
- RJTWDVHVVUEUGD-UHFFFAOYSA-N 2-[3-(methanesulfonamidomethyl)-4-[4-(phenylmethoxycarbamoyl)phenoxy]phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NOCC=2C=CC=CC=2)C=C1 RJTWDVHVVUEUGD-UHFFFAOYSA-N 0.000 claims 1
- OZKQHSUPRRZQNJ-UHFFFAOYSA-N 2-[3-(methanesulfonamidomethyl)-4-[4-[2-[3-(trifluoromethyl)phenyl]ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=C(C=CC=2)C(F)(F)F)C=C1 OZKQHSUPRRZQNJ-UHFFFAOYSA-N 0.000 claims 1
- SZSFSDUCABQSLK-UHFFFAOYSA-N 2-[3-(methanesulfonamidomethyl)-4-[4-[2-oxo-2-(2-phenylethylamino)ethyl]phenoxy]phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC(C=C1)=CC=C1CC(=O)NCCC1=CC=CC=C1 SZSFSDUCABQSLK-UHFFFAOYSA-N 0.000 claims 1
- XOBGYGVFYXMLPS-UHFFFAOYSA-N 2-[3-(methanesulfonamidomethyl)-4-[4-[[3-(trifluoromethyl)phenyl]carbamoyl]phenoxy]phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NC=2C=C(C=CC=2)C(F)(F)F)C=C1 XOBGYGVFYXMLPS-UHFFFAOYSA-N 0.000 claims 1
- ZTOUDBPQHWAQKU-UHFFFAOYSA-N 2-[3-(methanesulfonamidomethyl)-4-[4-[[4-(trifluoromethyl)phenyl]carbamoyl]phenoxy]phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)C=C1 ZTOUDBPQHWAQKU-UHFFFAOYSA-N 0.000 claims 1
- ZCEDRLJHNKDRBJ-UHFFFAOYSA-N 2-[3-[(cyclohexanecarbonylamino)methyl]-4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]phenyl]acetic acid Chemical compound C1CCCCC1C(=O)NCC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 ZCEDRLJHNKDRBJ-UHFFFAOYSA-N 0.000 claims 1
- RLGVKZNWDLMRCZ-UHFFFAOYSA-N 2-[3-[[(6-aminopyridine-3-carbonyl)amino]methyl]-4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound C1=NC(N)=CC=C1C(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 RLGVKZNWDLMRCZ-UHFFFAOYSA-N 0.000 claims 1
- WHQIQLCTPHJMRM-UHFFFAOYSA-N 2-[3-bromo-4-[4-[2-(2,4-dichlorophenyl)ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound BrC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)C=C1 WHQIQLCTPHJMRM-UHFFFAOYSA-N 0.000 claims 1
- FPIWVZSIJRTVRS-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 FPIWVZSIJRTVRS-UHFFFAOYSA-N 0.000 claims 1
- WZDDSKHKSNYVSZ-UHFFFAOYSA-N 2-[3-cyano-4-[4-(1,2,3,4-tetrahydronaphthalen-2-ylcarbamoyl)phenoxy]phenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NC2CC3=CC=CC=C3CC2)C=C1 WZDDSKHKSNYVSZ-UHFFFAOYSA-N 0.000 claims 1
- BBHSEVSJFHURJU-UHFFFAOYSA-N 2-[3-cyano-4-[4-(2-phenylethylcarbamoyl)phenoxy]phenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC=CC=2)C=C1 BBHSEVSJFHURJU-UHFFFAOYSA-N 0.000 claims 1
- QPVWRFSVMBTLNG-UHFFFAOYSA-N 2-[3-cyano-4-[4-[(2-phenylcyclopropyl)carbamoyl]phenoxy]phenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NC2C(C2)C=2C=CC=CC=2)C=C1 QPVWRFSVMBTLNG-UHFFFAOYSA-N 0.000 claims 1
- KWCRHELWBLSJSW-UHFFFAOYSA-N 2-[3-cyano-4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]phenyl]propanoic acid Chemical compound N#CC1=CC(C(C(O)=O)C)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 KWCRHELWBLSJSW-UHFFFAOYSA-N 0.000 claims 1
- KJUDCCWJLHWIDB-UHFFFAOYSA-N 2-[3-cyano-4-[4-[(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)carbamoyl]phenoxy]phenyl]acetic acid Chemical compound C1CC2=CC(OC)=CC=C2CC1NC(=O)C(C=C1)=CC=C1OC1=CC=C(CC(O)=O)C=C1C#N KJUDCCWJLHWIDB-UHFFFAOYSA-N 0.000 claims 1
- LRSHPFBLIYGFMF-UHFFFAOYSA-N 2-[3-cyano-4-[4-[2-(2,4-dichlorophenyl)ethylcarbamoyl]-3-fluorophenoxy]phenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC(C=C1F)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1Cl LRSHPFBLIYGFMF-UHFFFAOYSA-N 0.000 claims 1
- GQWUXWGRBCQNGK-UHFFFAOYSA-N 2-[3-cyano-4-[4-[2-(2,4-dichlorophenyl)ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)C=C1 GQWUXWGRBCQNGK-UHFFFAOYSA-N 0.000 claims 1
- VBUAISCHCBVIEQ-UHFFFAOYSA-N 2-[3-cyano-4-[4-[2-(2,6-dichlorophenyl)ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C(=CC=CC=2Cl)Cl)C=C1 VBUAISCHCBVIEQ-UHFFFAOYSA-N 0.000 claims 1
- VLVMNNNLIJZNJT-UHFFFAOYSA-N 2-[3-cyano-4-[4-[2-(3,4-dichlorophenyl)ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=C(Cl)C(Cl)=CC=2)C=C1 VLVMNNNLIJZNJT-UHFFFAOYSA-N 0.000 claims 1
- HLCMSNAONPTSTC-UHFFFAOYSA-N 2-[3-cyano-4-[4-[2-(3-fluorophenyl)ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=C(F)C=CC=2)C=C1 HLCMSNAONPTSTC-UHFFFAOYSA-N 0.000 claims 1
- UMPPTBPWPCPZFQ-UHFFFAOYSA-N 2-[3-cyano-4-[4-[2-(3-methoxyphenyl)ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound COC1=CC=CC(CCNC(=O)C=2C=CC(OC=3C(=CC(CC(O)=O)=CC=3)C#N)=CC=2)=C1 UMPPTBPWPCPZFQ-UHFFFAOYSA-N 0.000 claims 1
- RCXKIHBEWQEVNI-UHFFFAOYSA-N 2-[3-cyano-4-[4-[2-(4-fluorophenyl)ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(F)=CC=2)C=C1 RCXKIHBEWQEVNI-UHFFFAOYSA-N 0.000 claims 1
- OQIFQHIGUKXNQT-UHFFFAOYSA-N 2-[3-cyano-4-[4-[2-(4-methoxyphenyl)ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound C1=CC(OC)=CC=C1CCNC(=O)C(C=C1)=CC=C1OC1=CC=C(CC(O)=O)C=C1C#N OQIFQHIGUKXNQT-UHFFFAOYSA-N 0.000 claims 1
- VNTMJVRXRDIATN-UHFFFAOYSA-N 2-[3-cyano-4-[4-[2-(4-methylphenyl)ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound C1=CC(C)=CC=C1CCNC(=O)C(C=C1)=CC=C1OC1=CC=C(CC(O)=O)C=C1C#N VNTMJVRXRDIATN-UHFFFAOYSA-N 0.000 claims 1
- JCFCADMRGFDULV-UHFFFAOYSA-N 2-[3-cyano-4-[4-[2-[4-(trifluoromethyl)phenyl]ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(=CC=2)C(F)(F)F)C=C1 JCFCADMRGFDULV-UHFFFAOYSA-N 0.000 claims 1
- PJPFNAJCEXEVPS-UHFFFAOYSA-N 2-[4-[4-(2-anilino-2-oxoethyl)phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC(C=C1)=CC=C1CC(=O)NC1=CC=CC=C1 PJPFNAJCEXEVPS-UHFFFAOYSA-N 0.000 claims 1
- HZWZALRGUIUJMY-UHFFFAOYSA-N 2-[4-[4-(benzylcarbamoyl)phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCC=2C=CC=CC=2)C=C1 HZWZALRGUIUJMY-UHFFFAOYSA-N 0.000 claims 1
- XESKULREWPZSAU-UHFFFAOYSA-N 2-[4-[4-[(2-chlorobenzoyl)amino]phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1Cl XESKULREWPZSAU-UHFFFAOYSA-N 0.000 claims 1
- WVFFCOFGRIUMDE-UHFFFAOYSA-N 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-(methanesulfonamidomethyl)phenyl]-2-methylpropanoic acid Chemical compound CS(=O)(=O)NCC1=CC(C(C)(C(O)=O)C)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 WVFFCOFGRIUMDE-UHFFFAOYSA-N 0.000 claims 1
- GCHRMDXBRYDDDO-UHFFFAOYSA-N 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-(methanesulfonamidomethyl)phenyl]propanoic acid Chemical compound CS(=O)(=O)NCC1=CC(C(C(O)=O)C)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 GCHRMDXBRYDDDO-UHFFFAOYSA-N 0.000 claims 1
- FAQRSMNNJBHVRN-UHFFFAOYSA-N 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-[(methoxycarbonylamino)methyl]phenyl]acetic acid Chemical compound COC(=O)NCC1=CC(CC(O)=O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 FAQRSMNNJBHVRN-UHFFFAOYSA-N 0.000 claims 1
- AZABPOZXQMDWKR-UHFFFAOYSA-N 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-[(pyridin-3-ylsulfonylamino)methyl]phenyl]acetic acid Chemical compound C=1C=CN=CC=1S(=O)(=O)NCC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 AZABPOZXQMDWKR-UHFFFAOYSA-N 0.000 claims 1
- XDHAIXLWGSULRW-UHFFFAOYSA-N 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-[(pyridine-2-carbonylamino)methyl]phenyl]acetic acid Chemical compound C=1C=CC=NC=1C(=O)NCC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 XDHAIXLWGSULRW-UHFFFAOYSA-N 0.000 claims 1
- FWKRDGRNQGJQPD-UHFFFAOYSA-N 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-[(pyridine-3-carbonylamino)methyl]phenyl]acetic acid Chemical compound C=1C=CN=CC=1C(=O)NCC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 FWKRDGRNQGJQPD-UHFFFAOYSA-N 0.000 claims 1
- QXADRHMZWVAIAX-UHFFFAOYSA-N 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-[(pyridine-4-carbonylamino)methyl]phenyl]acetic acid Chemical compound C=1C=NC=CC=1C(=O)NCC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 QXADRHMZWVAIAX-UHFFFAOYSA-N 0.000 claims 1
- PJSOQGUCKVZZQP-UHFFFAOYSA-N 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-[[(2,4-dichlorophenyl)sulfonylamino]methyl]phenyl]acetic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1S(=O)(=O)NCC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 PJSOQGUCKVZZQP-UHFFFAOYSA-N 0.000 claims 1
- KUBRZCJYRQMUCL-UHFFFAOYSA-N 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-[[(4-fluorobenzoyl)amino]methyl]phenyl]acetic acid Chemical compound C=1C=C(F)C=CC=1C(=O)NCC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 KUBRZCJYRQMUCL-UHFFFAOYSA-N 0.000 claims 1
- COJBRJBTCYULNW-UHFFFAOYSA-N 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-[[(4-fluorophenyl)sulfonylamino]methyl]phenyl]acetic acid Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)NCC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 COJBRJBTCYULNW-UHFFFAOYSA-N 0.000 claims 1
- QAALQOVJHJFBLM-UHFFFAOYSA-N 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-methoxyphenyl]acetic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 QAALQOVJHJFBLM-UHFFFAOYSA-N 0.000 claims 1
- QTDXYHSAWJVOEN-UHFFFAOYSA-N 2-[4-[4-[(3,4-dichlorophenyl)carbamoyl]phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NC=2C=C(Cl)C(Cl)=CC=2)C=C1 QTDXYHSAWJVOEN-UHFFFAOYSA-N 0.000 claims 1
- YIWGQUJEAHOECZ-UHFFFAOYSA-N 2-[4-[4-[(3,4-difluorobenzoyl)amino]phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(F)C(F)=C1 YIWGQUJEAHOECZ-UHFFFAOYSA-N 0.000 claims 1
- JDZOGRCMWAHPNM-UHFFFAOYSA-N 2-[4-[4-[(3-chloro-4-fluorophenyl)carbamoyl]phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NC=2C=C(Cl)C(F)=CC=2)C=C1 JDZOGRCMWAHPNM-UHFFFAOYSA-N 0.000 claims 1
- NJBIYKYKBCPLQX-UHFFFAOYSA-N 2-[4-[4-[(3-chlorobenzoyl)amino]phenoxy]-3-[[(4-fluorophenyl)sulfonylamino]methyl]phenyl]acetic acid Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)NCC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=CC(Cl)=C1 NJBIYKYKBCPLQX-UHFFFAOYSA-N 0.000 claims 1
- KUKXAEMVCOQUJW-UHFFFAOYSA-N 2-[4-[4-[(4-chloro-3-fluorophenyl)carbamoyl]phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NC=2C=C(F)C(Cl)=CC=2)C=C1 KUKXAEMVCOQUJW-UHFFFAOYSA-N 0.000 claims 1
- YFWSUBNOKZSEFJ-UHFFFAOYSA-N 2-[4-[4-[(4-chlorobenzoyl)amino]phenoxy]-3-[[(4-fluorophenyl)sulfonylamino]methyl]phenyl]acetic acid Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)NCC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 YFWSUBNOKZSEFJ-UHFFFAOYSA-N 0.000 claims 1
- DNLGOTSRLZRWNG-UHFFFAOYSA-N 2-[4-[4-[2-(3,4-dichlorophenyl)ethylcarbamoyl]phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=C(Cl)C(Cl)=CC=2)C=C1 DNLGOTSRLZRWNG-UHFFFAOYSA-N 0.000 claims 1
- HSDHWWKJICNYGR-UHFFFAOYSA-N 2-[4-[4-[2-(3-chlorophenyl)ethylcarbamoyl]phenoxy]-3-cyanophenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=C(Cl)C=CC=2)C=C1 HSDHWWKJICNYGR-UHFFFAOYSA-N 0.000 claims 1
- PEZZDBHHHAQANH-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3,5-dimethylphenyl]acetic acid Chemical compound CC1=CC(CC(O)=O)=CC(C)=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 PEZZDBHHHAQANH-UHFFFAOYSA-N 0.000 claims 1
- JQGGGOAUJRAVHN-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-(3-methylsulfonylphenyl)phenyl]acetic acid Chemical compound CS(=O)(=O)C1=CC=CC(C=2C(=CC=C(CC(O)=O)C=2)OC=2C=CC(=CC=2)C(=O)NCCC=2C=CC(Cl)=CC=2)=C1 JQGGGOAUJRAVHN-UHFFFAOYSA-N 0.000 claims 1
- RBZBIJCEGRHONG-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-(4-methylsulfonylphenyl)phenyl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 RBZBIJCEGRHONG-UHFFFAOYSA-N 0.000 claims 1
- ZIQBBKHRQARKRT-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 ZIQBBKHRQARKRT-UHFFFAOYSA-N 0.000 claims 1
- ITATWACUKAVEJQ-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-[(dimethylamino)methyl]phenyl]acetic acid Chemical compound CN(C)CC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 ITATWACUKAVEJQ-UHFFFAOYSA-N 0.000 claims 1
- MLVVDNLQYQWNBQ-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-[(pyridin-3-ylsulfonylamino)methyl]phenyl]acetic acid Chemical compound C=1C=CN=CC=1S(=O)(=O)NCC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1 MLVVDNLQYQWNBQ-UHFFFAOYSA-N 0.000 claims 1
- NBTFNOPLJJLIOL-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-[(pyridine-3-carbonylamino)methyl]phenyl]acetic acid Chemical compound C=1C=CN=CC=1C(=O)NCC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1 NBTFNOPLJJLIOL-UHFFFAOYSA-N 0.000 claims 1
- SOKCIIYFIOXWBN-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-[[(3-methylimidazol-4-yl)sulfonylamino]methyl]phenyl]acetic acid Chemical compound CN1C=NC=C1S(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 SOKCIIYFIOXWBN-UHFFFAOYSA-N 0.000 claims 1
- UFBCIHJJPVYQHL-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-[[[2-[(4-fluorophenyl)sulfonylamino]acetyl]amino]methyl]phenyl]acetic acid Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)NCC(=O)NCC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1 UFBCIHJJPVYQHL-UHFFFAOYSA-N 0.000 claims 1
- OHCMQGQCROEVKM-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-[[methyl(methylsulfonyl)amino]methyl]phenyl]acetic acid Chemical compound CS(=O)(=O)N(C)CC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 OHCMQGQCROEVKM-UHFFFAOYSA-N 0.000 claims 1
- VJNMQMFRRYSIRC-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-cyanophenyl]-2-fluoroacetic acid Chemical compound N#CC1=CC(C(F)C(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 VJNMQMFRRYSIRC-UHFFFAOYSA-N 0.000 claims 1
- XLLQSQSPCLWIEQ-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-cyanophenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 XLLQSQSPCLWIEQ-UHFFFAOYSA-N 0.000 claims 1
- KMNBLICUWBKLIH-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-cyanophenyl]propanoic acid Chemical compound N#CC1=CC(C(C(O)=O)C)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 KMNBLICUWBKLIH-UHFFFAOYSA-N 0.000 claims 1
- TXKOLAPCEKEYSJ-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-cyclopropylphenyl]acetic acid Chemical compound C1CC1C1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1 TXKOLAPCEKEYSJ-UHFFFAOYSA-N 0.000 claims 1
- IWZJHLCTTLLVPN-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-ethylphenyl]acetic acid Chemical compound CCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 IWZJHLCTTLLVPN-UHFFFAOYSA-N 0.000 claims 1
- GAYAWBNUMHZFRG-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-fluorophenyl]acetic acid Chemical compound FC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 GAYAWBNUMHZFRG-UHFFFAOYSA-N 0.000 claims 1
- UJPNEJNUMWNZDP-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-methoxyphenyl]acetic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 UJPNEJNUMWNZDP-UHFFFAOYSA-N 0.000 claims 1
- OVQBANWLFQETND-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-methylphenyl]acetic acid Chemical compound CC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 OVQBANWLFQETND-UHFFFAOYSA-N 0.000 claims 1
- AZHLDAIQQLBAOO-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-phenylphenyl]acetic acid Chemical compound C=1C=CC=CC=1C1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1 AZHLDAIQQLBAOO-UHFFFAOYSA-N 0.000 claims 1
- KFIDIFZVYZWNQI-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-thiophen-2-ylphenyl]acetic acid Chemical compound C=1C=CSC=1C1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1 KFIDIFZVYZWNQI-UHFFFAOYSA-N 0.000 claims 1
- AFVSFZGYEQJQTC-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 AFVSFZGYEQJQTC-UHFFFAOYSA-N 0.000 claims 1
- VXFWJJJIFUEHHS-UHFFFAOYSA-N 2-[4-[4-[2-(4-fluorophenyl)ethylcarbamoyl]phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(F)=CC=2)C=C1 VXFWJJJIFUEHHS-UHFFFAOYSA-N 0.000 claims 1
- JTMGLPCBVZGXQJ-UHFFFAOYSA-N 2-[4-[4-[2-(4-tert-butylphenyl)ethylcarbamoyl]phenoxy]-3-cyanophenyl]acetic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1CCNC(=O)C(C=C1)=CC=C1OC1=CC=C(CC(O)=O)C=C1C#N JTMGLPCBVZGXQJ-UHFFFAOYSA-N 0.000 claims 1
- PFHULMIUFRZOOK-UHFFFAOYSA-N 2-[4-[4-[2-(benzylamino)-2-oxoethyl]phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC(C=C1)=CC=C1CC(=O)NCC1=CC=CC=C1 PFHULMIUFRZOOK-UHFFFAOYSA-N 0.000 claims 1
- HCBAPJIHNLBCLZ-UHFFFAOYSA-N 2-[4-[4-[2-[(4-chlorophenyl)methylamino]-2-oxoethyl]phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC(C=C1)=CC=C1CC(=O)NCC1=CC=C(Cl)C=C1 HCBAPJIHNLBCLZ-UHFFFAOYSA-N 0.000 claims 1
- LGJGJLBKNKOLLS-UHFFFAOYSA-N 2-[4-[4-[2-[benzyl(methyl)amino]-2-oxoethyl]phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound C=1C=C(OC=2C(=CC(CC(O)=O)=CC=2)CNS(C)(=O)=O)C=CC=1CC(=O)N(C)CC1=CC=CC=C1 LGJGJLBKNKOLLS-UHFFFAOYSA-N 0.000 claims 1
- ZASJPPYCBQIBPO-UHFFFAOYSA-N 2-[4-[4-[[1-(4-chlorophenyl)cyclopropyl]carbamoyl]phenoxy]-3-cyanophenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NC2(CC2)C=2C=CC(Cl)=CC=2)C=C1 ZASJPPYCBQIBPO-UHFFFAOYSA-N 0.000 claims 1
- GNRRBHUAJFYMJW-UHFFFAOYSA-N 2-[4-[4-[[1-(4-chlorophenyl)cyclopropyl]methylcarbamoyl]phenoxy]-3-(methanesulfonamidomethyl)phenyl]acetic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(O)=O)=CC=C1OC1=CC=C(C(=O)NCC2(CC2)C=2C=CC(Cl)=CC=2)C=C1 GNRRBHUAJFYMJW-UHFFFAOYSA-N 0.000 claims 1
- RAFIMVXAGIMWSH-UHFFFAOYSA-N 2-[4-[4-[[1-(4-chlorophenyl)cyclopropyl]methylcarbamoyl]phenoxy]-3-cyanophenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCC2(CC2)C=2C=CC(Cl)=CC=2)C=C1 RAFIMVXAGIMWSH-UHFFFAOYSA-N 0.000 claims 1
- QMLDPSITGQRFIJ-UHFFFAOYSA-N 2-[4-[4-[[2-(4-chlorophenyl)-2-hydroxyethyl]carbamoyl]phenoxy]-3-cyanophenyl]acetic acid Chemical compound C=1C=C(Cl)C=CC=1C(O)CNC(=O)C(C=C1)=CC=C1OC1=CC=C(CC(O)=O)C=C1C#N QMLDPSITGQRFIJ-UHFFFAOYSA-N 0.000 claims 1
- MCNNHWUAJWKGNJ-UHFFFAOYSA-N 2-[4-[4-[[2-(4-chlorophenyl)cyclopropyl]carbamoyl]phenoxy]-3-cyanophenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NC2C(C2)C=2C=CC(Cl)=CC=2)C=C1 MCNNHWUAJWKGNJ-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
- 229960003966 nicotinamide Drugs 0.000 claims 1
- 235000005152 nicotinamide Nutrition 0.000 claims 1
- 239000011570 nicotinamide Substances 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 0 Cc1c(*)cc(C=O)cc1BrC Chemical compound Cc1c(*)cc(C=O)cc1BrC 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83901806P | 2006-08-21 | 2006-08-21 | |
| US60/839,018 | 2006-08-21 | ||
| US85138506P | 2006-10-13 | 2006-10-13 | |
| US60/851,385 | 2006-10-13 | ||
| PCT/US2007/076378 WO2008024746A1 (en) | 2006-08-21 | 2007-08-21 | 4-substituted phenoxyphenylacetic acid derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010501587A JP2010501587A (ja) | 2010-01-21 |
| JP2010501587A5 true JP2010501587A5 (show.php) | 2010-09-24 |
| JP5582634B2 JP5582634B2 (ja) | 2014-09-03 |
Family
ID=38904570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009525728A Expired - Fee Related JP5582634B2 (ja) | 2006-08-21 | 2007-08-21 | ４−置換フェノキシフェニル酢酸誘導体 |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US8183289B2 (show.php) |
| EP (1) | EP2057115B9 (show.php) |
| JP (1) | JP5582634B2 (show.php) |
| KR (1) | KR101397352B1 (show.php) |
| CN (1) | CN101553461A (show.php) |
| AU (1) | AU2007286829B2 (show.php) |
| BR (1) | BRPI0715617A2 (show.php) |
| CA (1) | CA2661164C (show.php) |
| CO (1) | CO6160224A2 (show.php) |
| DK (1) | DK2057115T3 (show.php) |
| ES (1) | ES2396715T3 (show.php) |
| HR (1) | HRP20130004T8 (show.php) |
| IL (1) | IL197135A (show.php) |
| MX (1) | MX2009001876A (show.php) |
| MY (1) | MY149934A (show.php) |
| NZ (1) | NZ575507A (show.php) |
| PL (1) | PL2057115T3 (show.php) |
| PT (1) | PT2057115E (show.php) |
| RS (1) | RS52627B (show.php) |
| RU (1) | RU2463292C2 (show.php) |
| SG (1) | SG174069A1 (show.php) |
| SI (1) | SI2057115T1 (show.php) |
| TW (1) | TWI409247B (show.php) |
| UA (1) | UA96459C2 (show.php) |
| WO (1) | WO2008024746A1 (show.php) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2661164C (en) * | 2006-08-21 | 2014-10-28 | Array Biopharma, Inc. | 4-substituted phenoxyphenylacetic acid derivatives |
| TW200900072A (en) * | 2007-03-22 | 2009-01-01 | Arete Therapeutics Inc | Soluble epoxide hydrolase inhibitors |
| WO2009061730A2 (en) * | 2007-11-05 | 2009-05-14 | Array Biopharma Inc. | 4-heteroaryl-substituted phenoxyphenylacetic acid |
| NZ587709A (en) | 2008-02-01 | 2012-06-29 | Panmira Pharmaceuticals Llc | N,n-disubstituted aminoalkylbiphenyl antagonists of prostaglandin d2 receptors |
| WO2009102893A2 (en) * | 2008-02-14 | 2009-08-20 | Amira Pharmaceuticals, Inc. | CYCLIC DIARYL ETHER COMPOUNDS AS ANTAGONISTS OF PROSTAGLANDIN D2 receptors |
| EP2245022A4 (en) | 2008-02-25 | 2012-02-22 | Panmira Pharmaceuticals Llc | ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS |
| US8426449B2 (en) | 2008-04-02 | 2013-04-23 | Panmira Pharmaceuticals, Llc | Aminoalkylphenyl antagonists of prostaglandin D2 receptors |
| HRP20140988T1 (hr) | 2008-06-25 | 2014-12-05 | Array Biopharma, Inc. | Derivati 6-supstituirane fenoksikromankarboksilne kiseline |
| EP2307362A4 (en) * | 2008-07-03 | 2012-05-09 | Panmira Pharmaceuticals Llc | ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS |
| GB2463788B (en) | 2008-09-29 | 2010-12-15 | Amira Pharmaceuticals Inc | Heteroaryl antagonists of prostaglandin D2 receptors |
| US8378107B2 (en) | 2008-10-01 | 2013-02-19 | Panmira Pharmaceuticals, Llc | Heteroaryl antagonists of prostaglandin D2 receptors |
| WO2010042652A2 (en) | 2008-10-08 | 2010-04-15 | Amira Pharmaceuticals, Inc. | Heteroalkyl biphenyl antagonists of prostaglandin d2 receptors |
| WO2010057118A2 (en) | 2008-11-17 | 2010-05-20 | Amira Pharmaceuticals, Inc. | Heterocyclic antagonists of prostaglandin d2 receptors |
| JP5575799B2 (ja) * | 2008-12-22 | 2014-08-20 | アレイ バイオファーマ、インコーポレイテッド | ７−フェノキシクロマンカルボン酸誘導体 |
| WO2010094956A1 (en) | 2009-02-17 | 2010-08-26 | Pulmagen Therapeutics (Inflammation) Limited. | Triazolopyridine derivatives as p38 map kinase inhibitors |
| WO2011014587A2 (en) | 2009-07-31 | 2011-02-03 | Amira Pharmaceuticals, Inc. | Ophthalmic pharmaceutical compositions of dp2 receptor antagonists |
| SG10201404662YA (en) | 2009-08-05 | 2014-10-30 | Panmira Pharmaceuticals Llc | Dp2 antagonist and uses thereof |
| EP2521713A4 (en) | 2010-01-06 | 2013-10-02 | Panmira Pharmaceuticals Llc | ANTAGONIST OF DP2 AND ITS USES |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| EP2526945A1 (en) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | New CRTH2 Antagonists |
| EP2548876A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists |
| EP2548863A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists. |
| CA2859284A1 (en) | 2011-12-16 | 2013-06-20 | Atopix Therapeutics Limited | Combination of a crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
| CN104016878B (zh) * | 2014-06-24 | 2015-06-10 | 中国药科大学 | 芳基乙酸类衍生物、其制备方法及其医药用途 |
| ES2991300T3 (es) | 2015-02-13 | 2024-12-03 | Inserm Institut Nat De La Sante Et De Larecherche Medicale | Antagonistas de PTGDR-1 y/o PTGDR-2 para prevenir y/o tratar lupus eritematoso sistémico |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002528529A (ja) * | 1998-11-04 | 2002-09-03 | ビーエーエスエフ アクチェンゲゼルシャフト | ２−フェノキシフェニル酢酸誘導体、その製造のための方法および中間体、その使用、ならびにそれを含む有害真菌防除用組成物 |
| JP2001072653A (ja) * | 1999-07-01 | 2001-03-21 | Taisho Pharmaceut Co Ltd | アミノ安息香酸誘導体 |
| GB0015205D0 (en) * | 2000-06-21 | 2000-08-09 | Karobio Ab | Bioisosteric thyroid receptor ligands and method |
| JP2002193800A (ja) * | 2000-12-22 | 2002-07-10 | Taisho Pharmaceut Co Ltd | Ｖｅｇｆ受容体拮抗剤 |
| TW200408393A (en) | 2002-10-03 | 2004-06-01 | Ono Pharmaceutical Co | Antagonist of lysophosphatidine acid receptor |
| ES2401079T3 (es) * | 2002-12-20 | 2013-04-16 | Amgen Inc. | Moduladores del asma y de la inflamación alérgica |
| US7557143B2 (en) * | 2003-04-18 | 2009-07-07 | Bristol-Myers Squibb Company | Thyroid receptor ligands |
| GB0415320D0 (en) | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
| KR100927563B1 (ko) * | 2004-08-06 | 2009-11-23 | 오쓰까 세이야꾸 가부시키가이샤 | 방향족 화합물 |
| AU2007256597A1 (en) | 2006-06-09 | 2007-12-13 | Icos Corporation | Substituted phenyl acetic acids as DP-2 antagonists |
| CA2661164C (en) * | 2006-08-21 | 2014-10-28 | Array Biopharma, Inc. | 4-substituted phenoxyphenylacetic acid derivatives |
-
2007
- 2007-08-21 CA CA2661164A patent/CA2661164C/en not_active Expired - Fee Related
- 2007-08-21 RS RS20120563A patent/RS52627B/sr unknown
- 2007-08-21 US US12/438,112 patent/US8183289B2/en not_active Expired - Fee Related
- 2007-08-21 TW TW096130898A patent/TWI409247B/zh not_active IP Right Cessation
- 2007-08-21 WO PCT/US2007/076378 patent/WO2008024746A1/en not_active Ceased
- 2007-08-21 HR HRP20130004TT patent/HRP20130004T8/hr unknown
- 2007-08-21 UA UAA200902429A patent/UA96459C2/uk unknown
- 2007-08-21 SI SI200731117T patent/SI2057115T1/sl unknown
- 2007-08-21 NZ NZ575507A patent/NZ575507A/en not_active IP Right Cessation
- 2007-08-21 PL PL07814294T patent/PL2057115T3/pl unknown
- 2007-08-21 MY MYPI20090706A patent/MY149934A/en unknown
- 2007-08-21 JP JP2009525728A patent/JP5582634B2/ja not_active Expired - Fee Related
- 2007-08-21 MX MX2009001876A patent/MX2009001876A/es active IP Right Grant
- 2007-08-21 ES ES07814294T patent/ES2396715T3/es active Active
- 2007-08-21 SG SG2011057858A patent/SG174069A1/en unknown
- 2007-08-21 KR KR1020097005733A patent/KR101397352B1/ko not_active Expired - Fee Related
- 2007-08-21 DK DK07814294.0T patent/DK2057115T3/da active
- 2007-08-21 RU RU2009110183/04A patent/RU2463292C2/ru not_active IP Right Cessation
- 2007-08-21 CN CNA200780039235XA patent/CN101553461A/zh active Pending
- 2007-08-21 EP EP07814294A patent/EP2057115B9/en active Active
- 2007-08-21 AU AU2007286829A patent/AU2007286829B2/en not_active Ceased
- 2007-08-21 PT PT78142940T patent/PT2057115E/pt unknown
- 2007-08-21 BR BRPI0715617-0A2A patent/BRPI0715617A2/pt not_active IP Right Cessation
-
2009
- 2009-02-19 IL IL197135A patent/IL197135A/en active IP Right Grant
- 2009-03-12 CO CO09025722A patent/CO6160224A2/es unknown
-
2012
- 2012-04-17 US US13/448,689 patent/US8492437B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010501587A5 (show.php) | ||
| IL197135A (en) | The phenoxyphenylacetic acid derivatives are preserved in position 4, preparations containing them, their uses and methods for preparing them | |
| EP0686625B1 (en) | Anthranilic acid derivative | |
| JP5085659B2 (ja) | Ｌ−ｃｐｔ１阻害剤として有用なインダゾール誘導体 | |
| JP5498786B2 (ja) | 新規なマロン酸スルホンアミド誘導体およびその医薬用途 | |
| JP2015517981A5 (show.php) | ||
| JPH10500697A (ja) | タチキニン ｎｋ▲下３▼ 受容体アンタゴニストとしてのキノリン誘導体 | |
| JP2004525951A5 (show.php) | ||
| JPWO1997017329A1 (ja) | 血小板由来成長因子受容体自己リン酸化を阻害するキノリン誘導体ならびにキナゾリン誘導体およびそれらを含有する薬学的組成物 | |
| EP1302463A1 (en) | Medicine comprising dicyanopyridine derivative | |
| JP2002516314A5 (show.php) | ||
| JPH09509654A (ja) | サイクリックａｍｐホスホジエステラーゼおよびｔｎｆ阻害剤としての置換芳香族化合物 | |
| HRP20181076T1 (hr) | Pirazolski derivati kao modulatori kalcijevih kanala aktiviranih oslobađanjem kalcija | |
| JP2004504301A5 (show.php) | ||
| JP2007519692A5 (show.php) | ||
| JP2003535900A (ja) | ベンズアミド誘導体の治療薬としての使用 | |
| WO2001025190A1 (en) | Novel diarylamide derivatives and use thereof as medicines | |
| HRP20100284T1 (hr) | Derivati piperazinila korisni u liječenju bolesti posredovanih receptorom gpr38 | |
| US20070276011A1 (en) | Plasminogen Activator Inhibitor-1 Inhibitor | |
| TW200800200A (en) | Medicinal drug | |
| JP2005514432A5 (show.php) | ||
| CN109053630A (zh) | 一种苯并噻唑类衍生物及其用途 | |
| JP2008542365A5 (show.php) | ||
| JP2008524157A5 (show.php) | ||
| CA2666975A1 (en) | Aminopyrazole derivatives, process for the preparation thereof, and composition for preventing or treating ischemic diseases containing the same |