MX2009001876A - Derivados de acido fenoxifenilacetico 4-sustituidos. - Google Patents
Derivados de acido fenoxifenilacetico 4-sustituidos.Info
- Publication number
- MX2009001876A MX2009001876A MX2009001876A MX2009001876A MX2009001876A MX 2009001876 A MX2009001876 A MX 2009001876A MX 2009001876 A MX2009001876 A MX 2009001876A MX 2009001876 A MX2009001876 A MX 2009001876A MX 2009001876 A MX2009001876 A MX 2009001876A
- Authority
- MX
- Mexico
- Prior art keywords
- formula
- compound
- methyl
- group
- alkyl
- Prior art date
Links
- -1 4-substituted phenoxyphenylacetic acid Chemical class 0.000 title claims description 180
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 208000026278 immune system disease Diseases 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 80
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 229910052731 fluorine Inorganic materials 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 230000004075 alteration Effects 0.000 claims description 11
- 230000008878 coupling Effects 0.000 claims description 11
- 238000010168 coupling process Methods 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 8
- 229910052703 rhodium Inorganic materials 0.000 claims description 8
- 229910052701 rubidium Inorganic materials 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
- 108010016626 Dipeptides Proteins 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 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 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=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
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 201000004624 Dermatitis Diseases 0.000 claims description 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 3
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 3
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 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
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 206010009900 Colitis ulcerative 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
- 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
- 206010040047 Sepsis Diseases 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 208000036142 Viral infection Diseases 0.000 claims description 2
- 230000004761 fibrosis Effects 0.000 claims description 2
- 238000011010 flushing procedure Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
- 230000009385 viral infection Effects 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 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 206010052568 Urticaria chronic Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 201000005547 chronic conjunctivitis Diseases 0.000 claims 1
- 208000037976 chronic inflammation Diseases 0.000 claims 1
- 208000024376 chronic urticaria Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000001900 immune effect Effects 0.000 claims 1
- 239000007943 implant Substances 0.000 claims 1
- 230000004968 inflammatory condition Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 101150034985 Ptgdr2 gene Proteins 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 290
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 193
- 238000006243 chemical reaction Methods 0.000 description 124
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 115
- 235000019439 ethyl acetate Nutrition 0.000 description 105
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 77
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 72
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 62
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 56
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
- 238000005481 NMR spectroscopy Methods 0.000 description 51
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
- 239000000741 silica gel Substances 0.000 description 43
- 229910002027 silica gel Inorganic materials 0.000 description 43
- 229910001868 water Inorganic materials 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 39
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 36
- 239000000243 solution Substances 0.000 description 36
- 239000012044 organic layer Substances 0.000 description 35
- 239000010410 layer Substances 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 33
- 238000003756 stirring Methods 0.000 description 33
- 239000007787 solid Substances 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 28
- 235000019341 magnesium sulphate Nutrition 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
- 239000012267 brine Substances 0.000 description 26
- 238000004587 chromatography analysis Methods 0.000 description 26
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
- 229910000027 potassium carbonate Inorganic materials 0.000 description 24
- 239000000463 material Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 239000002253 acid Substances 0.000 description 20
- 239000003921 oil Substances 0.000 description 19
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 229910000029 sodium carbonate Inorganic materials 0.000 description 18
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 15
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- 239000013058 crude material Substances 0.000 description 13
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 13
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 10
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 10
- ACIMQXSSGMWVKG-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)ethanamine Chemical compound NCCC1=C(Cl)C=CC=C1Cl ACIMQXSSGMWVKG-UHFFFAOYSA-N 0.000 description 9
- 101150041968 CDC13 gene Proteins 0.000 description 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 8
- 206010007559 Cardiac failure congestive Diseases 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- SRXFXCKTIGELTI-UHFFFAOYSA-N 2-(4-chlorophenyl)ethanamine Chemical compound NCCC1=CC=C(Cl)C=C1 SRXFXCKTIGELTI-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 7
- 102100038312 Transcription factor Dp-2 Human genes 0.000 description 7
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 7
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 7
- IWXJBVIYCDMWHX-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-4-hydroxybenzamide Chemical compound C1=CC(O)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1 IWXJBVIYCDMWHX-UHFFFAOYSA-N 0.000 description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- KQFYNURGIZFXQL-UHFFFAOYSA-N tert-butyl 2-(3-cyano-4-fluorophenyl)acetate Chemical compound CC(C)(C)OC(=O)CC1=CC=C(F)C(C#N)=C1 KQFYNURGIZFXQL-UHFFFAOYSA-N 0.000 description 7
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 4
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 4
- 150000008046 alkali metal hydrides Chemical class 0.000 description 4
- 208000026935 allergic disease Diseases 0.000 description 4
- 125000006242 amine protecting group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- ANVVKEIGMQVMCI-UHFFFAOYSA-N tert-butyl 2-(3-cyano-4-fluorophenyl)propanoate Chemical compound CC(C)(C)OC(=O)C(C)C1=CC=C(F)C(C#N)=C1 ANVVKEIGMQVMCI-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- OTKFCIVOVKCFHR-UHFFFAOYSA-N (Methylsulfinyl)(methylthio)methane Chemical compound CSCS(C)=O OTKFCIVOVKCFHR-UHFFFAOYSA-N 0.000 description 3
- ZQQHAKWFOCNXKF-UHFFFAOYSA-N 3,4-dichloro-n-(4-hydroxyphenyl)benzamide Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 ZQQHAKWFOCNXKF-UHFFFAOYSA-N 0.000 description 3
- FAHZIKXYYRGSHF-UHFFFAOYSA-N 3-bromo-4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1Br FAHZIKXYYRGSHF-UHFFFAOYSA-N 0.000 description 3
- IFGFGFZDNZQMHM-UHFFFAOYSA-N 4-[2-cyano-4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]phenoxy]benzoic acid Chemical compound N#CC1=CC(CC(=O)OC(C)(C)C)=CC=C1OC1=CC=C(C(O)=O)C=C1 IFGFGFZDNZQMHM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000004820 halides Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- PEKKAWAYFODGNL-UHFFFAOYSA-N methyl 2-[4-hydroxy-3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]acetate Chemical compound COC(=O)CC1=CC=C(O)C(CNC(=O)OC(C)(C)C)=C1 PEKKAWAYFODGNL-UHFFFAOYSA-N 0.000 description 3
- RXFDIHKNMYKAHO-UHFFFAOYSA-N methyl 4-[2-cyano-4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]phenoxy]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OC1=CC=C(CC(=O)OC(C)(C)C)C=C1C#N RXFDIHKNMYKAHO-UHFFFAOYSA-N 0.000 description 3
- 229940095102 methyl benzoate Drugs 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 210000003491 skin Anatomy 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- IYTUKSIOQKTZEG-UHFFFAOYSA-N (3-chloro-4-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(O)C(Cl)=C1 IYTUKSIOQKTZEG-UHFFFAOYSA-N 0.000 description 2
- VHJKDOLGYMULOP-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)ethanamine Chemical group NCCC1=CC=C(Cl)C=C1Cl VHJKDOLGYMULOP-UHFFFAOYSA-N 0.000 description 2
- CKLFJWXRWIQYOC-UHFFFAOYSA-N 2-(4-fluorophenyl)ethanamine Chemical compound NCCC1=CC=C(F)C=C1 CKLFJWXRWIQYOC-UHFFFAOYSA-N 0.000 description 2
- DVXKDINRFXUASI-UHFFFAOYSA-N 2-[3-(aminomethyl)-4-hydroxyphenyl]acetic acid Chemical compound NCC1=CC(CC(O)=O)=CC=C1O DVXKDINRFXUASI-UHFFFAOYSA-N 0.000 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- YRQAAFWOILTMJQ-UHFFFAOYSA-N 2-[4-hydroxy-3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]acetic acid Chemical compound CC(C)(C)OC(=O)NCC1=CC(CC(O)=O)=CC=C1O YRQAAFWOILTMJQ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- IWLGXPWQZDOMSB-UHFFFAOYSA-N 4-chloro-3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC=C1Cl IWLGXPWQZDOMSB-UHFFFAOYSA-N 0.000 description 2
- ZGVXLIVLKUJBEP-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)ethyl]-3-nitrobenzamide Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C(=O)NCCC=2C=CC(Cl)=CC=2)=C1 ZGVXLIVLKUJBEP-UHFFFAOYSA-N 0.000 description 2
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
- 239000007821 HATU Substances 0.000 description 2
- 208000031886 HIV Infections Diseases 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- MNSGOOCAMMSKGI-UHFFFAOYSA-N N-(hydroxymethyl)phthalimide Chemical compound C1=CC=C2C(=O)N(CO)C(=O)C2=C1 MNSGOOCAMMSKGI-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VXHKUEKHNVGRTP-UHFFFAOYSA-N [1-(4-chlorophenyl)cyclopropyl]methanamine Chemical compound C=1C=C(Cl)C=CC=1C1(CN)CC1 VXHKUEKHNVGRTP-UHFFFAOYSA-N 0.000 description 2
- 230000009285 allergic inflammation Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 208000026106 cerebrovascular disease Diseases 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- QNRXKJPXIIVERP-UHFFFAOYSA-N ethyl 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-(trifluoromethyl)phenyl]acetate Chemical compound FC(F)(F)C1=CC(CC(=O)OCC)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 QNRXKJPXIIVERP-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 210000005095 gastrointestinal system Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 230000009610 hypersensitivity Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- ACBFEXJHCINJDS-UHFFFAOYSA-N methyl 2-(3-chloro-4-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C(Cl)=C1 ACBFEXJHCINJDS-UHFFFAOYSA-N 0.000 description 2
- AXONPFSLAZILIE-UHFFFAOYSA-N methyl 2-(3-fluoro-4-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C(F)=C1 AXONPFSLAZILIE-UHFFFAOYSA-N 0.000 description 2
- JJJSFAGPWHEUBT-UHFFFAOYSA-N methyl 2-(4-hydroxy-3-methoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C(OC)=C1 JJJSFAGPWHEUBT-UHFFFAOYSA-N 0.000 description 2
- XGDZEDRBLVIUMX-UHFFFAOYSA-N methyl 2-(4-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C=C1 XGDZEDRBLVIUMX-UHFFFAOYSA-N 0.000 description 2
- CNFDDRUWBFPDCS-UHFFFAOYSA-N methyl 2-[4-(4-aminophenoxy)-3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]acetate Chemical compound CC(C)(C)OC(=O)NCC1=CC(CC(=O)OC)=CC=C1OC1=CC=C(N)C=C1 CNFDDRUWBFPDCS-UHFFFAOYSA-N 0.000 description 2
- AYIBMTKOTXNBQP-UHFFFAOYSA-N methyl 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-methoxyphenyl]acetate Chemical compound COC1=CC(CC(=O)OC)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 AYIBMTKOTXNBQP-UHFFFAOYSA-N 0.000 description 2
- BILVBEGHSLIQSQ-UHFFFAOYSA-N methyl 4-[2-(aminomethyl)-4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]phenoxy]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OC1=CC=C(CC(=O)OC(C)(C)C)C=C1CN BILVBEGHSLIQSQ-UHFFFAOYSA-N 0.000 description 2
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- OPMBTSSEEJYFFM-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-2-fluoro-4-hydroxybenzamide Chemical compound FC1=CC(O)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1Cl OPMBTSSEEJYFFM-UHFFFAOYSA-N 0.000 description 2
- HZEUZMZISXEXPD-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-4-[4-formyl-2-(trifluoromethyl)phenoxy]benzamide Chemical compound FC(F)(F)C1=CC(C=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 HZEUZMZISXEXPD-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- 229940117803 phenethylamine Drugs 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VCHUSRRAQBUQBM-UHFFFAOYSA-N tert-butyl 2-(3-cyano-4-fluorophenyl)-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)C1=CC=C(F)C(C#N)=C1 VCHUSRRAQBUQBM-UHFFFAOYSA-N 0.000 description 2
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RREAHDRLAPCGEM-UHFFFAOYSA-N (2-chloro-2-phenylethyl) carbamate Chemical compound NC(=O)OCC(Cl)C1=CC=CC=C1 RREAHDRLAPCGEM-UHFFFAOYSA-N 0.000 description 1
- FEMCYPYMYXYDRS-UHFFFAOYSA-N (2Z)-2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-cyanophenyl]-2-diazoacetic acid Chemical compound OC(=O)C(=[N+]=[N-])c1ccc(Oc2ccc(cc2)C(=O)NCCc2ccc(Cl)cc2)c(c1)C#N FEMCYPYMYXYDRS-UHFFFAOYSA-N 0.000 description 1
- XMBSMMCPKFDGEO-ZETCQYMHSA-N (2s)-2-amino-5-[[amino-(2-methoxyethylamino)methylidene]amino]pentanoic acid Chemical compound COCCNC(=N)NCCC[C@H](N)C(O)=O XMBSMMCPKFDGEO-ZETCQYMHSA-N 0.000 description 1
- HZFFUMBZBGETES-UHFFFAOYSA-N (3-methylsulfonylphenyl)boronic acid Chemical compound CS(=O)(=O)C1=CC=CC(B(O)O)=C1 HZFFUMBZBGETES-UHFFFAOYSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- VDUKDQTYMWUSAC-UHFFFAOYSA-N (4-methylsulfonylphenyl)boronic acid Chemical compound CS(=O)(=O)C1=CC=C(B(O)O)C=C1 VDUKDQTYMWUSAC-UHFFFAOYSA-N 0.000 description 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 1
- FJQOAYUXVCSSQR-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound [Cl-].C1=CC=C2CC([NH3+])CCC2=C1 FJQOAYUXVCSSQR-UHFFFAOYSA-N 0.000 description 1
- UQTQBRJXTQDWHY-UHFFFAOYSA-N 1-(4-chlorophenyl)cyclopropan-1-amine;hydrochloride Chemical compound Cl.C=1C=C(Cl)C=CC=1C1(N)CC1 UQTQBRJXTQDWHY-UHFFFAOYSA-N 0.000 description 1
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 description 1
- MQPUAVYKVIHUJP-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)ethanamine Chemical compound NCCC1=CC=C(Cl)C(Cl)=C1 MQPUAVYKVIHUJP-UHFFFAOYSA-N 0.000 description 1
- NRHVNPYOTNGECT-UHFFFAOYSA-N 2-(3-chlorophenyl)ethanamine Chemical compound NCCC1=CC=CC(Cl)=C1 NRHVNPYOTNGECT-UHFFFAOYSA-N 0.000 description 1
- OASMBRFGIWZUJS-UHFFFAOYSA-N 2-(3-cyano-4-fluorophenyl)-2-methylpropanoic acid Chemical compound CC(C)(C(O)=O)c1ccc(F)c(c1)C#N OASMBRFGIWZUJS-UHFFFAOYSA-N 0.000 description 1
- YRFBZAHYMOSSGX-UHFFFAOYSA-N 2-(3-fluoro-4-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(O)C(F)=C1 YRFBZAHYMOSSGX-UHFFFAOYSA-N 0.000 description 1
- AUCVZEYHEFAWHO-UHFFFAOYSA-N 2-(3-fluorophenyl)ethanamine Chemical compound NCCC1=CC=CC(F)=C1 AUCVZEYHEFAWHO-UHFFFAOYSA-N 0.000 description 1
- WJBMRZAHTUFBGE-UHFFFAOYSA-N 2-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC(CCN)=C1 WJBMRZAHTUFBGE-UHFFFAOYSA-N 0.000 description 1
- VQLXPSANRSPTEZ-UHFFFAOYSA-N 2-(4-chlorophenyl)cyclopropan-1-amine Chemical compound NC1CC1C1=CC=C(Cl)C=C1 VQLXPSANRSPTEZ-UHFFFAOYSA-N 0.000 description 1
- WKCZSFRAGKIIKN-UHFFFAOYSA-N 2-(4-tert-butylphenyl)ethanamine Chemical compound CC(C)(C)C1=CC=C(CCN)C=C1 WKCZSFRAGKIIKN-UHFFFAOYSA-N 0.000 description 1
- XAEAUZAGDOXYIE-UHFFFAOYSA-N 2-[(4-fluorophenyl)sulfonylamino]acetic acid Chemical compound OC(=O)CNS(=O)(=O)C1=CC=C(F)C=C1 XAEAUZAGDOXYIE-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 1
- BTLGYCIABRKJDN-UHFFFAOYSA-N 2-[3-[(1,3-dioxoisoindol-2-yl)methyl]-4-hydroxyphenyl]acetic acid Chemical compound OC(=O)CC1=CC=C(O)C(CN2C(C3=CC=CC=C3C2=O)=O)=C1 BTLGYCIABRKJDN-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- VTZIRTMGGWHWOQ-UHFFFAOYSA-N 2-[3-bromo-4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]phenyl]acetic acid Chemical compound BrC1=CC(CC(=O)O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 VTZIRTMGGWHWOQ-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 1
- KXBDPKQUQFFCDS-UHFFFAOYSA-N 2-[3-cyano-4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]phenyl]acetic acid Chemical compound N#CC1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 KXBDPKQUQFFCDS-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- VNAQQDFAFUNPSQ-UHFFFAOYSA-N 2-[3-cyano-4-[4-[2-(2,4-dichlorophenyl)ethylcarbamoyl]phenoxy]phenyl]propanoic acid Chemical compound N#CC1=CC(C(C(O)=O)C)=CC=C1OC1=CC=C(C(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)C=C1 VNAQQDFAFUNPSQ-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 1
- HZKIFJONYKLHSP-UHFFFAOYSA-N 2-[4-(4-benzamidophenoxy)-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=C1 HZKIFJONYKLHSP-UHFFFAOYSA-N 0.000 description 1
- HMFOBPNVAAAACP-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]ethanamine Chemical compound NCCC1=CC=C(C(F)(F)F)C=C1 HMFOBPNVAAAACP-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 1
- QPHAZZJNYDEVHL-UHFFFAOYSA-N 2-amino-1-(4-chlorophenyl)ethanol Chemical compound NCC(O)C1=CC=C(Cl)C=C1 QPHAZZJNYDEVHL-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- NXWTWYULZRDBSA-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1F NXWTWYULZRDBSA-UHFFFAOYSA-N 0.000 description 1
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 1
- 125000004918 2-methyl-2-pentyl group Chemical group CC(C)(CCC)* 0.000 description 1
- 125000004922 2-methyl-3-pentyl group Chemical group CC(C)C(CC)* 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- AELCINSCMGFISI-UHFFFAOYSA-N 2-phenylcyclopropan-1-amine Chemical compound NC1CC1C1=CC=CC=C1 AELCINSCMGFISI-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- RPQWXGVZELKOEU-UHFFFAOYSA-N 3,4-difluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1F RPQWXGVZELKOEU-UHFFFAOYSA-N 0.000 description 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- YSSRLOJIPKHGCY-UHFFFAOYSA-N 3-amino-n-cyclohexyl-3-sulfanylidenepropanamide Chemical compound NC(=S)CC(=O)NC1CCCCC1 YSSRLOJIPKHGCY-UHFFFAOYSA-N 0.000 description 1
- YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 1
- WHIHIKVIWVIIER-UHFFFAOYSA-N 3-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1 WHIHIKVIWVIIER-UHFFFAOYSA-N 0.000 description 1
- LVVBPBKJOBKDKL-UHFFFAOYSA-N 3-cyclopropyl-4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1C1CC1 LVVBPBKJOBKDKL-UHFFFAOYSA-N 0.000 description 1
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 1
- 125000004919 3-methyl-2-pentyl group Chemical group CC(C(C)*)CC 0.000 description 1
- 125000004921 3-methyl-3-pentyl group Chemical group CC(CC)(CC)* 0.000 description 1
- HPUYBHMZERINQZ-UHFFFAOYSA-N 4-(2-bromo-4-formylphenoxy)-n-[2-(4-chlorophenyl)ethyl]benzamide Chemical compound C1=CC(Cl)=CC=C1CCNC(=O)C(C=C1)=CC=C1OC1=CC=C(C=O)C=C1Br HPUYBHMZERINQZ-UHFFFAOYSA-N 0.000 description 1
- PHCOGGYLWBWYJW-UHFFFAOYSA-N 4-[2-(methanesulfonamidomethyl)-4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]phenoxy]benzoic acid Chemical compound CS(=O)(=O)NCC1=CC(CC(=O)OC(C)(C)C)=CC=C1OC1=CC=C(C(O)=O)C=C1 PHCOGGYLWBWYJW-UHFFFAOYSA-N 0.000 description 1
- SJCDLUQYMCNMCJ-JLPGSUDCSA-N 4-[2-bromo-4-[(z)-2-methylsulfanyl-2-methylsulfinylethenyl]phenoxy]-n-[2-(4-chlorophenyl)ethyl]benzamide Chemical compound BrC1=CC(/C=C(/SC)S(C)=O)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 SJCDLUQYMCNMCJ-JLPGSUDCSA-N 0.000 description 1
- ACMJJQYSPUPMPN-UHFFFAOYSA-N 4-chloro-3-fluoroaniline Chemical compound NC1=CC=C(Cl)C(F)=C1 ACMJJQYSPUPMPN-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- NNHYTIOMCJAWLM-UHFFFAOYSA-N 4-fluoro-3,5-dimethylbenzaldehyde Chemical group CC1=CC(C=O)=CC(C)=C1F NNHYTIOMCJAWLM-UHFFFAOYSA-N 0.000 description 1
- BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical compound FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 description 1
- LTPVSOCPYWDIFU-UHFFFAOYSA-N 4-methoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1 LTPVSOCPYWDIFU-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- VKJXAQYPOTYDLO-UHFFFAOYSA-N 4-methylphenethylamine Chemical compound CC1=CC=C(CCN)C=C1 VKJXAQYPOTYDLO-UHFFFAOYSA-N 0.000 description 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
- ZCIFWRHIEBXBOY-UHFFFAOYSA-N 6-aminonicotinic acid Chemical compound NC1=CC=C(C(O)=O)C=N1 ZCIFWRHIEBXBOY-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 208000027496 Behcet disease Diseases 0.000 description 1
- 208000009137 Behcet syndrome Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- DHNYKWBWHRTGCN-UHFFFAOYSA-N C(C1=CC=CC=C1)NC(CC1=CC=C(OC2=CC(=C(C=C2)CC(=O)O)CNS(=O)(=O)C)C=C1)=O Chemical compound C(C1=CC=CC=C1)NC(CC1=CC=C(OC2=CC(=C(C=C2)CC(=O)O)CNS(=O)(=O)C)C=C1)=O DHNYKWBWHRTGCN-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010007556 Cardiac failure acute Diseases 0.000 description 1
- 208000031229 Cardiomyopathies Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- YHFMWEMRABAJBW-UHFFFAOYSA-N ClC1=CC=C(C=C1)CCNC(=O)C1=CC=C(OC2=CC(=C(C=C2)CC(=O)O)C2CC2)C=C1 Chemical compound ClC1=CC=C(C=C1)CCNC(=O)C1=CC=C(OC2=CC(=C(C=C2)CC(=O)O)C2CC2)C=C1 YHFMWEMRABAJBW-UHFFFAOYSA-N 0.000 description 1
- 108091026890 Coding region Proteins 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 description 1
- 206010056489 Coronary artery restenosis Diseases 0.000 description 1
- 206010011091 Coronary artery thrombosis Diseases 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- 101710155962 Diuretic hormone 2 Proteins 0.000 description 1
- 208000004232 Enteritis Diseases 0.000 description 1
- 208000010228 Erectile Dysfunction Diseases 0.000 description 1
- OHUJBUIPCLPWAC-UHFFFAOYSA-N FC1=C(C=O)C=CC=C1C1CC1 Chemical compound FC1=C(C=O)C=CC=C1C1CC1 OHUJBUIPCLPWAC-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000004262 Food Hypersensitivity Diseases 0.000 description 1
- 108010076288 Formyl peptide receptors Proteins 0.000 description 1
- 102000011652 Formyl peptide receptors Human genes 0.000 description 1
- 208000007882 Gastritis Diseases 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 208000003807 Graves Disease Diseases 0.000 description 1
- 208000015023 Graves' disease Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000666385 Homo sapiens Transcription factor Dp-2 Proteins 0.000 description 1
- 101000979190 Homo sapiens Transcription factor MafB Proteins 0.000 description 1
- 241000701806 Human papillomavirus Species 0.000 description 1
- 206010048643 Hypereosinophilic syndrome Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010033078 Otitis media Diseases 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 210000004241 Th2 cell Anatomy 0.000 description 1
- 102100023234 Transcription factor MafB Human genes 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 208000030886 Traumatic Brain injury Diseases 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 206010057469 Vascular stenosis Diseases 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 208000002205 allergic conjunctivitis Diseases 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 238000010976 amide bond formation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000024998 atopic conjunctivitis Diseases 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 239000012148 binding buffer Substances 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000010322 bone marrow transplantation Methods 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000003679 cervix uteri Anatomy 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 208000018631 connective tissue disease Diseases 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 208000002528 coronary thrombosis Diseases 0.000 description 1
- 208000004921 cutaneous lupus erythematosus Diseases 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- 230000003831 deregulation Effects 0.000 description 1
- KJOZJSGOIJQCGA-UHFFFAOYSA-N dichloromethane;2,2,2-trifluoroacetic acid Chemical compound ClCCl.OC(=O)C(F)(F)F KJOZJSGOIJQCGA-UHFFFAOYSA-N 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004520 electroporation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- FBMWURVKVTYTGV-UHFFFAOYSA-N ethyl 2-[3-bromo-4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]phenyl]acetate Chemical compound BrC1=CC(CC(=O)OCC)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 FBMWURVKVTYTGV-UHFFFAOYSA-N 0.000 description 1
- CCGDOYRQIVEDFF-UHFFFAOYSA-N ethyl 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-(3-methylsulfonylphenyl)phenyl]acetate Chemical compound C=1C=CC(S(C)(=O)=O)=CC=1C1=CC(CC(=O)OCC)=CC=C1OC(C=C1)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1 CCGDOYRQIVEDFF-UHFFFAOYSA-N 0.000 description 1
- JCVCJTKNUPNAFS-UHFFFAOYSA-N ethyl 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-cyclopropylphenyl]acetate Chemical compound C1CC1C1=CC(CC(=O)OCC)=CC=C1OC(C=C1)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1 JCVCJTKNUPNAFS-UHFFFAOYSA-N 0.000 description 1
- QLPIUTFPYORSAD-UHFFFAOYSA-N ethyl 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-ethylphenyl]acetate Chemical compound CCC1=CC(CC(=O)OCC)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 QLPIUTFPYORSAD-UHFFFAOYSA-N 0.000 description 1
- NOEUBUKJDLHLJI-UHFFFAOYSA-N ethyl 2-[4-[4-[2-(4-chlorophenyl)ethylcarbamoyl]phenoxy]-3-methylphenyl]acetate Chemical compound CC1=CC(CC(=O)OCC)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC(Cl)=CC=2)C=C1 NOEUBUKJDLHLJI-UHFFFAOYSA-N 0.000 description 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000020932 food allergy Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 102000055674 human TFDP2 Human genes 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 208000009326 ileitis Diseases 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- APNSGVMLAYLYCT-UHFFFAOYSA-N isobutyl nitrite Chemical compound CC(C)CON=O APNSGVMLAYLYCT-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- QHDRKFYEGYYIIK-UHFFFAOYSA-N isovaleronitrile Chemical compound CC(C)CC#N QHDRKFYEGYYIIK-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000000867 larynx Anatomy 0.000 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004324 lymphatic system Anatomy 0.000 description 1
- VFZXMEQGIIWBFJ-UHFFFAOYSA-M magnesium;cyclopropane;bromide Chemical compound [Mg+2].[Br-].C1C[CH-]1 VFZXMEQGIIWBFJ-UHFFFAOYSA-M 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VERIKVNJTDANJM-UHFFFAOYSA-N methyl 2-[3-(aminomethyl)-4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]phenyl]acetate Chemical compound NCC1=CC(CC(=O)OC)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 VERIKVNJTDANJM-UHFFFAOYSA-N 0.000 description 1
- SOOMXLSZICEUGL-UHFFFAOYSA-N methyl 2-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-4-(4-nitrophenoxy)phenyl]acetate Chemical compound CC(C)(C)OC(=O)NCC1=CC(CC(=O)OC)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 SOOMXLSZICEUGL-UHFFFAOYSA-N 0.000 description 1
- FBXVOLJFARBFAX-UHFFFAOYSA-N methyl 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]acetate Chemical compound CC(C)(C)OC(=O)NCC1=CC(CC(=O)OC)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 FBXVOLJFARBFAX-UHFFFAOYSA-N 0.000 description 1
- HWOSAPSPFDPFFO-UHFFFAOYSA-N methyl 2-[4-[4-[(3,4-dichlorobenzoyl)amino]phenoxy]-3-[[(4-fluorophenyl)sulfonylamino]methyl]phenyl]acetate Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)NCC1=CC(CC(=O)OC)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 HWOSAPSPFDPFFO-UHFFFAOYSA-N 0.000 description 1
- PYUKSRKHDDSDBG-UHFFFAOYSA-N methyl 4-[2-(methanesulfonamidomethyl)-4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]phenoxy]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OC1=CC=C(CC(=O)OC(C)(C)C)C=C1CNS(C)(=O)=O PYUKSRKHDDSDBG-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000006362 methylene amino carbonyl group Chemical group [H]N(C([*:2])=O)C([H])([H])[*:1] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
- ZFCCVDNNIAHGFR-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-4-hydroxybenzamide Chemical compound C1=CC(O)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1Cl ZFCCVDNNIAHGFR-UHFFFAOYSA-N 0.000 description 1
- WEJYSDAJEGETML-IMRQLAEWSA-N n-[2-(4-chlorophenyl)ethyl]-4-[2-cyclopropyl-4-[(z)-2-methylsulfanyl-2-methylsulfinylethenyl]phenoxy]benzamide Chemical compound C1CC1C1=CC(/C=C(/SC)S(C)=O)=CC=C1OC(C=C1)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1 WEJYSDAJEGETML-IMRQLAEWSA-N 0.000 description 1
- DDZYQYGLQIBSJF-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-4-iodobenzamide Chemical compound C1=CC(Cl)=CC=C1CCNC(=O)C1=CC=C(I)C=C1 DDZYQYGLQIBSJF-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 201000003631 narcolepsy Diseases 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 208000011851 neurological alteration Diseases 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000001185 psoriatic effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PSAYJRPASWETSH-UHFFFAOYSA-N pyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CC=N1 PSAYJRPASWETSH-UHFFFAOYSA-N 0.000 description 1
- CDRNYKLYADJTMN-UHFFFAOYSA-N pyridine-3-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CN=C1 CDRNYKLYADJTMN-UHFFFAOYSA-N 0.000 description 1
- VIVPWOMJFLICOZ-UHFFFAOYSA-N pyridine-3-sulfonyl chloride;hydrochloride Chemical compound Cl.ClS(=O)(=O)C1=CC=CN=C1 VIVPWOMJFLICOZ-UHFFFAOYSA-N 0.000 description 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 201000002859 sleep apnea Diseases 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 208000022925 sleep disturbance Diseases 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- NNGDLOYUAYPSNM-UHFFFAOYSA-N tert-butyl 2-(4-hydroxyphenyl)acetate Chemical compound CC(C)(C)OC(=O)CC1=CC=C(O)C=C1 NNGDLOYUAYPSNM-UHFFFAOYSA-N 0.000 description 1
- RUJWZCJYYWOFCZ-UHFFFAOYSA-N tert-butyl 2-[3-cyano-4-[4-(2-phenylethylcarbamoyl)phenoxy]phenyl]acetate Chemical compound N#CC1=CC(CC(=O)OC(C)(C)C)=CC=C1OC1=CC=C(C(=O)NCCC=2C=CC=CC=2)C=C1 RUJWZCJYYWOFCZ-UHFFFAOYSA-N 0.000 description 1
- WVSCCEDTTKTXQR-UHFFFAOYSA-N tert-butyl 2-[3-cyano-4-[4-[2-(2,4-dichlorophenyl)ethylcarbamoyl]-3-fluorophenoxy]phenyl]acetate Chemical compound N#CC1=CC(CC(=O)OC(C)(C)C)=CC=C1OC(C=C1F)=CC=C1C(=O)NCCC1=CC=C(Cl)C=C1Cl WVSCCEDTTKTXQR-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
- 210000001550 testis Anatomy 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 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
- 238000002054 transplantation Methods 0.000 description 1
- 230000009529 traumatic brain injury Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- QXXJGZQLPDQOPF-UHFFFAOYSA-M zinc;benzene;iodide Chemical compound I[Zn+].C1=CC=[C-]C=C1 QXXJGZQLPDQOPF-UHFFFAOYSA-M 0.000 description 1
- NMLXKNNXODLJIN-UHFFFAOYSA-M zinc;carbanide;chloride Chemical compound [CH3-].[Zn+]Cl NMLXKNNXODLJIN-UHFFFAOYSA-M 0.000 description 1
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
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/10—Sulfides; Sulfoxides; Sulfones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/75—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/87—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/04—Diamides of sulfuric acids
- C07C307/06—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to acyclic carbon atoms
-
- 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
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C311/06—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- C07D213/02—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
- C07D213/04—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
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- C07D213/02—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
- C07D213/04—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- C07D213/02—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
- C07D213/04—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- 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
- C07D233/42—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
-
- 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
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Neurosurgery (AREA)
- Virology (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Ophthalmology & Optometry (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Molecular Biology (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US83901806P | 2006-08-21 | 2006-08-21 | |
US85138506P | 2006-10-13 | 2006-10-13 | |
PCT/US2007/076378 WO2008024746A1 (en) | 2006-08-21 | 2007-08-21 | 4-substituted phenoxyphenylacetic acid derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
MX2009001876A true MX2009001876A (es) | 2009-03-06 |
Family
ID=38904570
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
MX2009001876A MX2009001876A (es) | 2006-08-21 | 2007-08-21 | Derivados de acido fenoxifenilacetico 4-sustituidos. |
Country Status (25)
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
-
2007
- 2007-08-21 RS RS20120563A patent/RS52627B/en unknown
- 2007-08-21 SG SG2011057858A patent/SG174069A1/en unknown
- 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
- 2007-08-21 PL PL07814294T patent/PL2057115T3/pl unknown
- 2007-08-21 WO PCT/US2007/076378 patent/WO2008024746A1/en active Application Filing
- 2007-08-21 CN CNA200780039235XA patent/CN101553461A/zh active Pending
- 2007-08-21 ES ES07814294T patent/ES2396715T3/es active Active
- 2007-08-21 RU RU2009110183/04A patent/RU2463292C2/ru not_active IP Right Cessation
- 2007-08-21 US US12/438,112 patent/US8183289B2/en not_active Expired - Fee Related
- 2007-08-21 MX MX2009001876A patent/MX2009001876A/es active IP Right Grant
- 2007-08-21 MY MYPI20090706A patent/MY149934A/en unknown
- 2007-08-21 UA UAA200902429A patent/UA96459C2/uk unknown
- 2007-08-21 DK DK07814294.0T patent/DK2057115T3/da active
- 2007-08-21 EP EP07814294A patent/EP2057115B9/en active Active
- 2007-08-21 AU AU2007286829A patent/AU2007286829B2/en not_active Ceased
- 2007-08-21 JP JP2009525728A patent/JP5582634B2/ja not_active Expired - Fee Related
- 2007-08-21 NZ NZ575507A patent/NZ575507A/en not_active IP Right Cessation
- 2007-08-21 PT PT78142940T patent/PT2057115E/pt unknown
- 2007-08-21 SI SI200731117T patent/SI2057115T1/sl unknown
- 2007-08-21 KR KR1020097005733A patent/KR101397352B1/ko not_active IP Right Cessation
- 2007-08-21 TW TW096130898A patent/TWI409247B/zh 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
-
2013
- 2013-01-03 HR HRP20130004TT patent/HRP20130004T8/hr unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8492437B2 (en) | 4-substituted phenoxyphenylacetic acid derivatives | |
CA2511214C (en) | Asthma and allergic inflammation modulators | |
JP4330341B2 (ja) | カンナビノイドレセプターリガンド | |
US7795471B2 (en) | Process for trans-4-amino-1-cyclohexanecarboxylic acid derivatives | |
SK281184B6 (sk) | Substituovaný sulfónamid, farmaceutická kompozícia na jeho báze a spôsob jeho prípravy | |
AU5650299A (en) | Benzene derivatives and medicinal use thereof | |
WO2004098584A1 (en) | Peptide deformylase inhibitors | |
JP2000007647A (ja) | スルホンアミド誘導体、アシル化剤及びアシル化方法 | |
JPH03190854A (ja) | インダン誘導体の製法及びその合成中間体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FG | Grant or registration |