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 (Direct) | 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 (Direct) |
| EP (1) | EP2057115B9 (Direct) |
| JP (1) | JP5582634B2 (Direct) |
| KR (1) | KR101397352B1 (Direct) |
| CN (1) | CN101553461A (Direct) |
| AU (1) | AU2007286829B2 (Direct) |
| BR (1) | BRPI0715617A2 (Direct) |
| CA (1) | CA2661164C (Direct) |
| CO (1) | CO6160224A2 (Direct) |
| DK (1) | DK2057115T3 (Direct) |
| ES (1) | ES2396715T3 (Direct) |
| HR (1) | HRP20130004T8 (Direct) |
| IL (1) | IL197135A (Direct) |
| MX (1) | MX2009001876A (Direct) |
| MY (1) | MY149934A (Direct) |
| NZ (1) | NZ575507A (Direct) |
| PL (1) | PL2057115T3 (Direct) |
| PT (1) | PT2057115E (Direct) |
| RS (1) | RS52627B (Direct) |
| RU (1) | RU2463292C2 (Direct) |
| SG (1) | SG174069A1 (Direct) |
| SI (1) | SI2057115T1 (Direct) |
| TW (1) | TWI409247B (Direct) |
| UA (1) | UA96459C2 (Direct) |
| WO (1) | WO2008024746A1 (Direct) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2057115E (pt) * | 2006-08-21 | 2012-12-26 | Array Biopharma Inc | Derivados de ácido fenoxifenilacético substituídos na posição |
| WO2008116145A2 (en) * | 2007-03-22 | 2008-09-25 | Arete Therapeutics, Inc. | Soluble epoxide hydrolase inhibitors |
| WO2009061730A2 (en) * | 2007-11-05 | 2009-05-14 | Array Biopharma Inc. | 4-heteroaryl-substituted phenoxyphenylacetic acid |
| EP2257524B1 (en) | 2008-02-01 | 2016-01-06 | Brickell Biotech, Inc. | 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 |
| US8497381B2 (en) | 2008-02-25 | 2013-07-30 | 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 |
| EP2826774B1 (en) * | 2008-06-25 | 2016-05-25 | Array Biopharma, Inc. | Intermediates for 6-substituted phenoxychroman carboxylic acid derivatives |
| CA2729292C (en) | 2008-07-03 | 2013-09-03 | Amira Pharmaceuticals, Inc. | Phenoxyphenyl sulfide, sulfinyl and sulfonyl antagonists of prostaglandin d2 receptors |
| GB2463788B (en) | 2008-09-29 | 2010-12-15 | Amira Pharmaceuticals Inc | Heteroaryl antagonists of prostaglandin D2 receptors |
| WO2010039977A2 (en) | 2008-10-01 | 2010-04-08 | Amira Pharmaceuticals, Inc. | Heteroaryl antagonists of prostaglandin d2 receptors |
| US8524748B2 (en) | 2008-10-08 | 2013-09-03 | Panmira Pharmaceuticals, Llc | Heteroalkyl biphenyl antagonists of prostaglandin D2 receptors |
| US8383654B2 (en) | 2008-11-17 | 2013-02-26 | Panmira Pharmaceuticals, Llc | Heterocyclic antagonists of prostaglandin D2 receptors |
| EP2379535B1 (en) | 2008-12-22 | 2016-06-15 | Array Biopharma Inc. | 7-phenoxychroman carboxylic acid derivatives |
| EA201190119A1 (ru) | 2009-02-17 | 2012-05-30 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | ПРОИЗВОДНЫЕ ТРИАЗОЛОПИРИДИНА В КАЧЕСТВЕ ИНГИБИТОРОВ МАР-КИНАЗЫ p38 |
| SG178109A1 (en) | 2009-07-31 | 2012-03-29 | Panmira Pharmaceuticals Llc | Ophthalmic pharmaceutical compositions of dp2 receptor antagonists |
| CN102596902A (zh) | 2009-08-05 | 2012-07-18 | 潘米拉制药公司 | Dp2拮抗剂及其用途 |
| WO2011085033A2 (en) * | 2010-01-06 | 2011-07-14 | Amira Pharmaceuticals, Inc. | Dp2 antagonist and uses thereof |
| 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 |
| EP2548863A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists. |
| EP2548876A1 (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 |
| EP4420734A3 (en) | 2015-02-13 | 2024-11-06 | Institut National de la Santé et de la Recherche Médicale | Ptgdr-1 and/or ptgdr-2 antagonists for preventing and/or treating systemic lupus erythematosus |
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 |
| WO2004031118A1 (ja) * | 2002-10-03 | 2004-04-15 | Ono Pharmaceutical Co., Ltd. | Ｌｐａ受容体拮抗剤 |
| CA2511214C (en) * | 2002-12-20 | 2012-12-18 | Tularik, Inc. | Asthma and allergic inflammation modulators |
| 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 |
| RU2416608C2 (ru) * | 2004-08-06 | 2011-04-20 | Оцука Фармасьютикал Ко., Лтд. | Ароматическое соединение |
| JP2009539880A (ja) | 2006-06-09 | 2009-11-19 | アイコス コーポレイション | Ｄｐ−２アンタゴニストとしての置換フェニル酢酸 |
| PT2057115E (pt) * | 2006-08-21 | 2012-12-26 | Array Biopharma Inc | Derivados de ácido fenoxifenilacético substituídos na posição |
-
2007
- 2007-08-21 PT PT78142940T patent/PT2057115E/pt unknown
- 2007-08-21 WO PCT/US2007/076378 patent/WO2008024746A1/en not_active Ceased
- 2007-08-21 UA UAA200902429A patent/UA96459C2/uk unknown
- 2007-08-21 HR HRP20130004TT patent/HRP20130004T8/hr unknown
- 2007-08-21 CN CNA200780039235XA patent/CN101553461A/zh active Pending
- 2007-08-21 ES ES07814294T patent/ES2396715T3/es active Active
- 2007-08-21 SI SI200731117T patent/SI2057115T1/sl unknown
- 2007-08-21 PL PL07814294T patent/PL2057115T3/pl unknown
- 2007-08-21 RS RS20120563A patent/RS52627B/sr unknown
- 2007-08-21 TW TW096130898A patent/TWI409247B/zh not_active IP Right Cessation
- 2007-08-21 JP JP2009525728A patent/JP5582634B2/ja not_active Expired - Fee Related
- 2007-08-21 US US12/438,112 patent/US8183289B2/en not_active Expired - Fee Related
- 2007-08-21 MY MYPI20090706A patent/MY149934A/en unknown
- 2007-08-21 NZ NZ575507A patent/NZ575507A/en not_active IP Right Cessation
- 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 AU AU2007286829A patent/AU2007286829B2/en not_active Ceased
- 2007-08-21 MX MX2009001876A patent/MX2009001876A/es active IP Right Grant
- 2007-08-21 EP EP07814294A patent/EP2057115B9/en active Active
- 2007-08-21 CA CA2661164A patent/CA2661164C/en not_active Expired - Fee Related
- 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 (Direct) | ||
| 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 (Direct) | ||
| 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 (Direct) | ||
| EP1302463A1 (en) | Medicine comprising dicyanopyridine derivative | |
| JP2002516314A5 (Direct) | ||
| 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 | |
| SI2509955T1 (en) | Pyrazole derivatives as calcium channel modulators activated by the release of calcium | |
| JP2004504301A5 (Direct) | ||
| JP2007519692A5 (Direct) | ||
| 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 (Direct) | ||
| AU616014B2 (en) | Butenoic or propenoic acid derivative | |
| JP2008542365A5 (Direct) | ||
| CA2666975A1 (en) | Aminopyrazole derivatives, process for the preparation thereof, and composition for preventing or treating ischemic diseases containing the same | |
| JP2009517368A5 (Direct) | ||
| CA2626402A1 (en) | Potassium channel inhibitors |