JP5582634B2 - 4−置換フェノキシフェニル酢酸誘導体 - Google Patents
4−置換フェノキシフェニル酢酸誘導体 Download PDFInfo
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- JP5582634B2 JP5582634B2 JP2009525728A JP2009525728A JP5582634B2 JP 5582634 B2 JP5582634 B2 JP 5582634B2 JP 2009525728 A JP2009525728 A JP 2009525728A JP 2009525728 A JP2009525728 A JP 2009525728A JP 5582634 B2 JP5582634 B2 JP 5582634B2
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- Prior art keywords
- phenoxy
- phenyl
- acetic acid
- methyl
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- -1 4-substituted phenoxyphenylacetic acid Chemical class 0.000 title claims description 188
- 150000001875 compounds Chemical class 0.000 claims description 155
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 91
- 238000000034 method Methods 0.000 claims description 85
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- 229910052731 fluorine Inorganic materials 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 125000001624 naphthyl group Chemical group 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 13
- 208000026278 immune system disease Diseases 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 12
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 10
- 238000010168 coupling process Methods 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 5
- 201000004624 Dermatitis Diseases 0.000 claims description 5
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 150000004820 halides Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 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 description 4
- 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 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 206010052779 Transplant rejections Diseases 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims description 4
- 208000010668 atopic eczema Diseases 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 206010016654 Fibrosis Diseases 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 206010028735 Nasal congestion Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000002193 Pain Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010037660 Pyrexia Diseases 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 208000036142 Viral infection Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 230000004761 fibrosis Effects 0.000 claims description 3
- 238000011010 flushing procedure Methods 0.000 claims description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 206010037844 rash Diseases 0.000 claims description 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 3
- 230000009385 viral infection Effects 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- KOPBLCRYUWVVTH-UHFFFAOYSA-N tert-butyl 2-[3-cyano-4-[4-[2-(2,4-dichlorophenyl)ethylcarbamoyl]phenoxy]phenyl]propanoate Chemical compound N#CC1=CC(C(C(=O)OC(C)(C)C)C)=CC=C1OC1=CC=C(C(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)C=C1 KOPBLCRYUWVVTH-UHFFFAOYSA-N 0.000 description 1
- MHAZTZGOPAHKRH-UHFFFAOYSA-N tert-butyl 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-[(pyridine-3-carbonylamino)methyl]phenyl]acetate Chemical compound C=1C=CN=CC=1C(=O)NCC1=CC(CC(=O)OC(C)(C)C)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 MHAZTZGOPAHKRH-UHFFFAOYSA-N 0.000 description 1
- HPYCJYBGQDKOQZ-UHFFFAOYSA-N tert-butyl 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-cyanophenyl]-2-diazoacetate Chemical compound N#CC1=CC(C(=[N+]=[N-])C(=O)OC(C)(C)C)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 HPYCJYBGQDKOQZ-UHFFFAOYSA-N 0.000 description 1
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- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C—CHEMISTRY; METALLURGY
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- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- C—CHEMISTRY; METALLURGY
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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US83901806P | 2006-08-21 | 2006-08-21 | |
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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 |
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JP2010501587A JP2010501587A (ja) | 2010-01-21 |
JP2010501587A5 JP2010501587A5 (US07132539-20061107-C00040.png) | 2010-09-24 |
JP5582634B2 true JP5582634B2 (ja) | 2014-09-03 |
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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 |
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RS52627B (en) * | 2006-08-21 | 2013-06-28 | Array Biopharma Inc. | 4-SUBSTITUTED Phenoxyphenylsulfuric acid derivatives |
TW200900072A (en) * | 2007-03-22 | 2009-01-01 | Arete Therapeutics Inc | Soluble epoxide hydrolase inhibitors |
US8362056B2 (en) * | 2007-11-05 | 2013-01-29 | Array Biopharma Inc. | 4-heteroaryl-substituted phenoxyphenylacetic acid derivatives |
KR101235961B1 (ko) | 2008-02-01 | 2013-02-21 | 판미라 파마슈티칼스, 엘엘씨 | 프로스타글란딘 d2 수용체의 n,n-이치환 아미노알킬비페닐 길항제 |
EP2257536A4 (en) * | 2008-02-14 | 2011-03-23 | Amira Pharmaceuticals Inc | CYCLIC DIARYL ETHERS 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 |
AU2009262274B2 (en) | 2008-06-25 | 2013-08-01 | Array Biopharma Inc. | 6-substituted phenoxychroman carboxylic acid derivatives |
US20110144160A1 (en) | 2008-07-03 | 2011-06-16 | Amira Pharmaceuticals, Inc. | 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 |
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 |
CA2748099C (en) * | 2008-12-22 | 2017-02-28 | Array Biopharma Inc. | 7-phenoxychroman carboxylic acid derivatives |
BRPI1005327A2 (pt) | 2009-02-17 | 2019-09-24 | Chiesi Farm Spa | derivados de triazolopiridina como inibidores de p38 map quinase |
KR20120038544A (ko) | 2009-07-31 | 2012-04-23 | 판미라 파마슈티칼스, 엘엘씨 | Dp2 수용체 길항제의 안과용 약학 조성물 |
MX2012001542A (es) | 2009-08-05 | 2012-06-19 | Panmira Pharmaceuticals Llc | Antagonista dp2 y usos del mismo. |
US9688624B2 (en) | 2010-01-06 | 2017-06-27 | Brickell Biotech, 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 |
AU2012351342A1 (en) | 2011-12-16 | 2014-07-24 | Atopix Therapeutics Limited | Combination of 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 |
EP3256121B1 (en) | 2015-02-13 | 2024-08-07 | INSERM - 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 |
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EP1127046A1 (de) * | 1998-11-04 | 2001-08-29 | Basf Aktiengesellschaft | 2-phenoxyphenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung, ihre verwendung und sie enthaltende mittel zur bekämpfung von schadpilzen |
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 |
NZ541234A (en) * | 2002-12-20 | 2008-06-30 | Amgen 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 |
WO2007143745A2 (en) | 2006-06-09 | 2007-12-13 | Icos Corporation | Substituted phenyl acetic acids as dp-2 antagonists |
RS52627B (en) * | 2006-08-21 | 2013-06-28 | Array Biopharma Inc. | 4-SUBSTITUTED Phenoxyphenylsulfuric acid derivatives |
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