JP2010501587A5 - - Google Patents
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- 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
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- -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
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| 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 |
| MX2011000173A (es) * | 2008-06-25 | 2011-06-20 | Array Biopharma Inc | Derivados de acido fenoxicroman-carboxilico 6-sustituido. |
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| US8383654B2 (en) | 2008-11-17 | 2013-02-26 | Panmira Pharmaceuticals, Llc | Heterocyclic antagonists of prostaglandin D2 receptors |
| CA2748099C (en) * | 2008-12-22 | 2017-02-28 | Array Biopharma Inc. | 7-phenoxychroman carboxylic acid derivatives |
| MA33128B1 (fr) | 2009-02-17 | 2012-03-01 | Chiesi Farma Spa | Derives de triazolopyridine utilises comme inhibiteurs de la p38 map kinase |
| SG178109A1 (en) | 2009-07-31 | 2012-03-29 | Panmira Pharmaceuticals Llc | Ophthalmic pharmaceutical compositions of dp2 receptor antagonists |
| KR20120047273A (ko) | 2009-08-05 | 2012-05-11 | 판미라 파마슈티칼스, 엘엘씨 | Ｄｐ2 길항제 및 이의 용도 |
| SG182398A1 (en) * | 2010-01-06 | 2012-08-30 | Panmira Pharmaceuticals Llc | Dp2 antagonist and uses thereof |
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| 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. |
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| US6469195B1 (en) * | 1998-11-04 | 2002-10-22 | Basf Aktiengesellschaft | 2-phenoxyphenylacetic acid derivatives, method and intermediate products for the production thereof, their use, and agents containing the same for combating fungicidal pests |
| 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 |
| EA011087B1 (ru) * | 2002-12-20 | 2008-12-30 | Эмджен Инк. | Соединения и фармацевтические композиции для лечения воспалительных заболеваний |
| 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 |
| CA2654784A1 (en) | 2006-06-09 | 2007-12-13 | Icos Corporation | Substituted phenylacetic acids as dp-2 antagonists |
| CN101553461A (zh) * | 2006-08-21 | 2009-10-07 | 阵列生物制药公司 | 4-取代的苯氧基苯基乙酸衍生物 |
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- 2007-08-21 US US12/438,112 patent/US8183289B2/en not_active Expired - Fee Related
- 2007-08-21 SI SI200731117T patent/SI2057115T1/sl unknown
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