IL179694A - Use of crth2 receptor ligands for the preparation of a pharmaceutical composition, some such ligands and pharmaceutical composition comprising the ligand - Google Patents
Use of crth2 receptor ligands for the preparation of a pharmaceutical composition, some such ligands and pharmaceutical composition comprising the ligandInfo
- Publication number
- IL179694A IL179694A IL179694A IL17969406A IL179694A IL 179694 A IL179694 A IL 179694A IL 179694 A IL179694 A IL 179694A IL 17969406 A IL17969406 A IL 17969406A IL 179694 A IL179694 A IL 179694A
- Authority
- IL
- Israel
- Prior art keywords
- bromo
- phenoxy
- carbonyl
- pyrazole
- acetic acid
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 239000003446 ligand Substances 0.000 title description 13
- 238000002360 preparation method Methods 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 158
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 148
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 90
- -1 chloro, bromo, iodo Chemical group 0.000 claims description 74
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 46
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 27
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 235000019260 propionic acid Nutrition 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 125000000335 thiazolyl group Chemical group 0.000 claims description 10
- 208000006673 asthma Diseases 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 206010039083 rhinitis Diseases 0.000 claims description 9
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 208000002197 Ehlers-Danlos syndrome Diseases 0.000 claims description 6
- 208000028004 allergic respiratory disease Diseases 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 201000001981 dermatomyositis Diseases 0.000 claims description 6
- 201000002491 encephalomyelitis Diseases 0.000 claims description 6
- 230000002757 inflammatory effect Effects 0.000 claims description 6
- 201000008482 osteoarthritis Diseases 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 208000002574 reactive arthritis Diseases 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 201000000306 sarcoidosis Diseases 0.000 claims description 6
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 230000000172 allergic effect Effects 0.000 claims description 5
- 208000010668 atopic eczema Diseases 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 4
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 4
- 206010020751 Hypersensitivity Diseases 0.000 claims description 4
- 230000007815 allergy Effects 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002720 diazolyl group Chemical group 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- QIQZFDHLXPAAIR-LBPRGKRZSA-N (2s)-2-[4-bromo-2-(1-phenylpyrazole-4-carbonyl)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 QIQZFDHLXPAAIR-LBPRGKRZSA-N 0.000 claims description 3
- BUNCEUVLTVTITF-UHFFFAOYSA-N 2-[4-bromo-2-(1-naphthalen-1-ylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C3=CC=CC=C3C=CC=2)N=C1 BUNCEUVLTVTITF-UHFFFAOYSA-N 0.000 claims description 3
- DMFOOUGJUFPBOG-UHFFFAOYSA-N 2-[4-bromo-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 DMFOOUGJUFPBOG-UHFFFAOYSA-N 0.000 claims description 3
- QIQZFDHLXPAAIR-UHFFFAOYSA-N 2-[4-bromo-2-(1-phenylpyrazole-4-carbonyl)phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 QIQZFDHLXPAAIR-UHFFFAOYSA-N 0.000 claims description 3
- FVFWAOFXTIHIKN-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,4-dibromophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC(Br)=CC=2)Br)N=C1 FVFWAOFXTIHIKN-UHFFFAOYSA-N 0.000 claims description 3
- UYBKPKQYTBHMHL-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,5-dichlorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=C(Cl)C=2)Cl)N=C1 UYBKPKQYTBHMHL-UHFFFAOYSA-N 0.000 claims description 3
- YVCFNRBEJVGESH-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-bromo-4-methylphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound BrC1=CC(C)=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 YVCFNRBEJVGESH-UHFFFAOYSA-N 0.000 claims description 3
- UEHKLYFBGNDQBL-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-ethoxyphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound CCOC1=CC=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 UEHKLYFBGNDQBL-UHFFFAOYSA-N 0.000 claims description 3
- DKMSWPXPOAAEEG-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-ethylphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound CCC1=CC=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 DKMSWPXPOAAEEG-UHFFFAOYSA-N 0.000 claims description 3
- UYBADZMRTPVYNZ-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-fluorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=CC=2)F)N=C1 UYBADZMRTPVYNZ-UHFFFAOYSA-N 0.000 claims description 3
- BFDKWNZBUIDXIV-UHFFFAOYSA-N 2-[4-bromo-2-[1-(4-chlorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=CC(Cl)=CC=2)N=C1 BFDKWNZBUIDXIV-UHFFFAOYSA-N 0.000 claims description 3
- HVJGLYFROPMIKZ-UHFFFAOYSA-N 2-[4-bromo-2-[2-[(4-chlorophenyl)methyl]-1,3-thiazol-4-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=CSC(CC=2C=CC(Cl)=CC=2)=N1 HVJGLYFROPMIKZ-UHFFFAOYSA-N 0.000 claims description 3
- 206010065040 AIDS dementia complex Diseases 0.000 claims description 3
- 208000009304 Acute Kidney Injury Diseases 0.000 claims description 3
- 208000035939 Alveolitis allergic Diseases 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
- 206010003267 Arthritis reactive Diseases 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 206010006811 Bursitis Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 206010010741 Conjunctivitis Diseases 0.000 claims description 3
- 206010011224 Cough Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
- 206010014950 Eosinophilia Diseases 0.000 claims description 3
- 208000027445 Farmer Lung Diseases 0.000 claims description 3
- 206010016228 Fasciitis Diseases 0.000 claims description 3
- 208000001640 Fibromyalgia Diseases 0.000 claims description 3
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 3
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
- 201000005569 Gout Diseases 0.000 claims description 3
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 3
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 208000009388 Job Syndrome Diseases 0.000 claims description 3
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims description 3
- 208000009829 Lewy Body Disease Diseases 0.000 claims description 3
- 201000002832 Lewy body dementia Diseases 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 3
- 201000002481 Myositis Diseases 0.000 claims description 3
- 206010065673 Nephritic syndrome Diseases 0.000 claims description 3
- 206010031264 Osteonecrosis Diseases 0.000 claims description 3
- 208000002193 Pain Diseases 0.000 claims description 3
- 206010056332 Panencephalitis Diseases 0.000 claims description 3
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 3
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 3
- 208000033464 Reiter syndrome Diseases 0.000 claims description 3
- 208000033626 Renal failure acute Diseases 0.000 claims description 3
- 206010063837 Reperfusion injury Diseases 0.000 claims description 3
- 206010039710 Scleroderma Diseases 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 206010040070 Septic Shock Diseases 0.000 claims description 3
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 3
- 208000016247 Soft tissue disease Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 208000000491 Tendinopathy Diseases 0.000 claims description 3
- 206010043255 Tendonitis Diseases 0.000 claims description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 201000004810 Vascular dementia Diseases 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 201000011040 acute kidney failure Diseases 0.000 claims description 3
- 208000012998 acute renal failure Diseases 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 206010006451 bronchitis Diseases 0.000 claims description 3
- 208000003295 carpal tunnel syndrome Diseases 0.000 claims description 3
- 208000025434 cerebellar degeneration Diseases 0.000 claims description 3
- 208000013116 chronic cough Diseases 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 208000020832 chronic kidney disease Diseases 0.000 claims description 3
- 208000022831 chronic renal failure syndrome Diseases 0.000 claims description 3
- 230000003210 demyelinating effect Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 208000022195 farmer lung disease Diseases 0.000 claims description 3
- 208000024908 graft versus host disease Diseases 0.000 claims description 3
- 206010051040 hyper-IgE syndrome Diseases 0.000 claims description 3
- 208000014674 injury Diseases 0.000 claims description 3
- 230000000302 ischemic effect Effects 0.000 claims description 3
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims description 3
- 201000010260 leiomyoma Diseases 0.000 claims description 3
- 210000004072 lung Anatomy 0.000 claims description 3
- 206010025135 lupus erythematosus Diseases 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- 206010065579 multifocal motor neuropathy Diseases 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 208000020469 nerve plexus disease Diseases 0.000 claims description 3
- 201000006380 plexopathy Diseases 0.000 claims description 3
- 208000015768 polyposis Diseases 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 230000036303 septic shock Effects 0.000 claims description 3
- 201000004415 tendinitis Diseases 0.000 claims description 3
- 238000002054 transplantation Methods 0.000 claims description 3
- 230000008733 trauma Effects 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- LSPQNLQIYOKMTN-UHFFFAOYSA-N 2-[2-[1-(2-bromophenyl)pyrazole-4-carbonyl]-4-ethylphenoxy]acetic acid Chemical compound CCC1=CC=C(OCC(O)=O)C(C(=O)C2=CN(N=C2)C=2C(=CC=CC=2)Br)=C1 LSPQNLQIYOKMTN-UHFFFAOYSA-N 0.000 claims description 2
- DTXMBWBTTBVOAE-UHFFFAOYSA-N 2-[4-bromo-2-(1-pyridin-2-ylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2N=CC=CC=2)N=C1 DTXMBWBTTBVOAE-UHFFFAOYSA-N 0.000 claims description 2
- GKJHYSSXTQZZKW-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,4-dimethylphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound CC1=CC(C)=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 GKJHYSSXTQZZKW-UHFFFAOYSA-N 0.000 claims description 2
- HBIZRZDCSVBMII-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,6-dichlorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=CC=2Cl)Cl)N=C1 HBIZRZDCSVBMII-UHFFFAOYSA-N 0.000 claims description 2
- AUZLWFVIFDXQCE-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-chlorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=CC=2)Cl)N=C1 AUZLWFVIFDXQCE-UHFFFAOYSA-N 0.000 claims description 2
- HYXYEMCQQAEHCZ-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-methylsulfanylphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound CSC1=CC=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 HYXYEMCQQAEHCZ-UHFFFAOYSA-N 0.000 claims description 2
- WHRYRALKFCAFQN-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-phenoxyphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N=C1 WHRYRALKFCAFQN-UHFFFAOYSA-N 0.000 claims description 2
- YTAHAXUTKQQUKM-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-phenoxyphenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N=C1 YTAHAXUTKQQUKM-UHFFFAOYSA-N 0.000 claims description 2
- GCBPFVHJPQPLKY-UHFFFAOYSA-N 2-[4-bromo-2-[1-(4-bromo-2-ethylphenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound CCC1=CC(Br)=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OC(C)C(O)=O)=C1 GCBPFVHJPQPLKY-UHFFFAOYSA-N 0.000 claims description 2
- BXBRRDYUSHNRHR-UHFFFAOYSA-N 2-[4-bromo-2-[3-[(4-fluorophenyl)methyl]-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(CC=2C=CC(F)=CC=2)=NO1 BXBRRDYUSHNRHR-UHFFFAOYSA-N 0.000 claims description 2
- PGKHSJWQTQODLJ-JTQLQIEISA-N (2s)-2-[4-bromo-2-[1-(2,6-dichlorophenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=CC=2Cl)Cl)N=C1 PGKHSJWQTQODLJ-JTQLQIEISA-N 0.000 claims 1
- YTAHAXUTKQQUKM-INIZCTEOSA-N (2s)-2-[4-bromo-2-[1-(2-phenoxyphenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=CC=2)OC=2C=CC=CC=2)N=C1 YTAHAXUTKQQUKM-INIZCTEOSA-N 0.000 claims 1
- AQNZKLWCJXMBRM-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,4,6-trichlorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC(Cl)=CC=2Cl)Cl)N=C1 AQNZKLWCJXMBRM-UHFFFAOYSA-N 0.000 claims 1
- LNKFHOQVEVTLKK-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,4,6-trichlorophenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC(Cl)=CC=2Cl)Cl)N=C1 LNKFHOQVEVTLKK-UHFFFAOYSA-N 0.000 claims 1
- KCUBSRLDNLOFHO-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,4-dichlorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC(Cl)=CC=2)Cl)N=C1 KCUBSRLDNLOFHO-UHFFFAOYSA-N 0.000 claims 1
- PGKHSJWQTQODLJ-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,6-dichlorophenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=CC=2Cl)Cl)N=C1 PGKHSJWQTQODLJ-UHFFFAOYSA-N 0.000 claims 1
- DRAVAXYLOCYCFL-UHFFFAOYSA-N 2-[4-bromo-2-[1-(4-chloro-2-methylphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound CC1=CC(Cl)=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 DRAVAXYLOCYCFL-UHFFFAOYSA-N 0.000 claims 1
- DOFQQQGQFQTAIH-UHFFFAOYSA-N 2-[4-bromo-2-[1-(4-chloro-2-methylphenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC(Cl)=CC=2)C)N=C1 DOFQQQGQFQTAIH-UHFFFAOYSA-N 0.000 claims 1
- PYKNTERJCDTNGU-UHFFFAOYSA-N 2-[4-bromo-2-[1-[2-(trifluoromethyl)phenyl]pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=CC=2)C(F)(F)F)N=C1 PYKNTERJCDTNGU-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 230000001363 autoimmune Effects 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
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 157
- 238000005160 1H NMR spectroscopy Methods 0.000 description 102
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 57
- PCEZXSJBHMOQFT-UHFFFAOYSA-N 6-bromo-4-oxochromene-3-carbaldehyde Chemical compound O1C=C(C=O)C(=O)C2=CC(Br)=CC=C21 PCEZXSJBHMOQFT-UHFFFAOYSA-N 0.000 description 51
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 44
- 238000005481 NMR spectroscopy Methods 0.000 description 41
- YGDGZDGRCWHDOU-UHFFFAOYSA-N methyl 4-[[5-chloro-4-(2-hydroxyphenyl)thiophen-2-yl]sulfonylamino]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=CC(C=2C(=CC=CC=2)O)=C(Cl)S1 YGDGZDGRCWHDOU-UHFFFAOYSA-N 0.000 description 41
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- FJYDBKPPGRZSOZ-UHFFFAOYSA-N methyl 5-bromo-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(Br)=CC=C1O FJYDBKPPGRZSOZ-UHFFFAOYSA-N 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 102000009389 Prostaglandin D receptors Human genes 0.000 description 23
- 108050000258 Prostaglandin D receptors Proteins 0.000 description 23
- 238000000034 method Methods 0.000 description 22
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 21
- 239000012074 organic phase Substances 0.000 description 21
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 17
- 210000004027 cell Anatomy 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- 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 15
- 239000007787 solid Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- DQSRVWNGCNSDNE-UHFFFAOYSA-N 3-(pyridin-3-ylamino)propyl 4-[[3-(5-fluoro-2-hydroxyphenyl)phenyl]sulfonylamino]-2-hydroxybenzoate Chemical compound OC1=CC=C(F)C=C1C1=CC=CC(S(=O)(=O)NC=2C=C(O)C(C(=O)OCCCNC=3C=NC=CC=3)=CC=2)=C1 DQSRVWNGCNSDNE-UHFFFAOYSA-N 0.000 description 11
- AAVABVUXRLAMAZ-UHFFFAOYSA-N ethyl 2-[4-bromo-2-(2-bromoacetyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(Br)C=C1C(=O)CBr AAVABVUXRLAMAZ-UHFFFAOYSA-N 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 238000003818 flash chromatography Methods 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 125000005647 linker group Chemical group 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- 238000009739 binding Methods 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 230000027455 binding Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- QSRRZKPKHJHIRB-UHFFFAOYSA-N methyl 4-[(2,5-dichloro-4-methylthiophen-3-yl)sulfonylamino]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=C(Cl)SC(Cl)=C1C QSRRZKPKHJHIRB-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 238000003556 assay Methods 0.000 description 7
- 238000005191 phase separation Methods 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- 238000000225 bioluminescence resonance energy transfer Methods 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- PVCONXMDUZOPJH-UHFFFAOYSA-N 5-bromo-2-hydroxybenzonitrile Chemical compound OC1=CC=C(Br)C=C1C#N PVCONXMDUZOPJH-UHFFFAOYSA-N 0.000 description 5
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 5
- KBXJQIDNYQTMNP-UHFFFAOYSA-N ethyl 2-[4-bromo-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 KBXJQIDNYQTMNP-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- IDTWYHVEGJBGPT-UHFFFAOYSA-N (2,6-dichlorophenyl)hydrazine Chemical compound NNC1=C(Cl)C=CC=C1Cl IDTWYHVEGJBGPT-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 229910014455 Ca-Cb Inorganic materials 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 210000003979 eosinophil Anatomy 0.000 description 4
- JHPRXXGEIYCARL-UHFFFAOYSA-N ethyl 2-(4-bromo-2-prop-2-ynoylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(Br)C=C1C(=O)C#C JHPRXXGEIYCARL-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- PYFSLJVSCGXYAJ-UHFFFAOYSA-N methyl 2-hydroxy-4-[[3-(2-hydroxyphenyl)phenyl]sulfonylamino]benzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=CC=CC(C=2C(=CC=CC=2)O)=C1 PYFSLJVSCGXYAJ-UHFFFAOYSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- CKQVIJPMZIQDSK-UHFFFAOYSA-N (2,6-diethylphenyl)hydrazine Chemical compound CCC1=CC=CC(CC)=C1NN CKQVIJPMZIQDSK-UHFFFAOYSA-N 0.000 description 3
- ZWMQVBSLMQSMDH-UHFFFAOYSA-N (2-bromophenyl)hydrazine Chemical compound NNC1=CC=CC=C1Br ZWMQVBSLMQSMDH-UHFFFAOYSA-N 0.000 description 3
- GHGPIPTUDQZJJS-UHFFFAOYSA-N (2-chlorophenyl)hydrazine Chemical compound NNC1=CC=CC=C1Cl GHGPIPTUDQZJJS-UHFFFAOYSA-N 0.000 description 3
- GWJSCRPGAMICGI-UHFFFAOYSA-N (2-ethoxyphenyl)hydrazine Chemical compound CCOC1=CC=CC=C1NN GWJSCRPGAMICGI-UHFFFAOYSA-N 0.000 description 3
- JWKDEJOHJDJLFZ-UHFFFAOYSA-N (4-bromo-2-ethylphenyl)hydrazine Chemical compound CCC1=CC(Br)=CC=C1NN JWKDEJOHJDJLFZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 description 3
- JBDRQGWTNRIJRV-UHFFFAOYSA-N 6-nitro-4-oxochromene-3-carbaldehyde Chemical compound O1C=C(C=O)C(=O)C2=CC([N+](=O)[O-])=CC=C21 JBDRQGWTNRIJRV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 3
- QHGFILIGTMBUGQ-UHFFFAOYSA-N ethyl 2-(4-bromo-2-formylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(Br)C=C1C=O QHGFILIGTMBUGQ-UHFFFAOYSA-N 0.000 description 3
- UBHLFUZICRCXAE-WDZFZDKYSA-N ethyl 2-[4-bromo-2-[(z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(Br)C=C1\C=C/1C(=O)NC(=O)S\1 UBHLFUZICRCXAE-WDZFZDKYSA-N 0.000 description 3
- IPYSXGPKPGNUNX-UHFFFAOYSA-N ethyl 2-[[5-bromo-2-(2-ethoxy-2-oxoethoxy)phenyl]methylamino]acetate Chemical compound CCOC(=O)CNCC1=CC(Br)=CC=C1OCC(=O)OCC IPYSXGPKPGNUNX-UHFFFAOYSA-N 0.000 description 3
- MGZFVSUXQXCEHM-UHFFFAOYSA-N ethyl 2-phenoxyacetate Chemical compound CCOC(=O)COC1=CC=CC=C1 MGZFVSUXQXCEHM-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000842 isoxazolyl group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 3
- MULHANRBCQBHII-UHFFFAOYSA-N (2,4,6-trichlorophenyl)hydrazine Chemical compound NNC1=C(Cl)C=C(Cl)C=C1Cl MULHANRBCQBHII-UHFFFAOYSA-N 0.000 description 2
- IEJSVSLXZNRULR-UHFFFAOYSA-N (2,4-dibromophenyl)hydrazine Chemical compound NNC1=CC=C(Br)C=C1Br IEJSVSLXZNRULR-UHFFFAOYSA-N 0.000 description 2
- ZTPAUBJZUBGGEY-UHFFFAOYSA-N (2,4-dichlorophenyl)hydrazine Chemical compound NNC1=CC=C(Cl)C=C1Cl ZTPAUBJZUBGGEY-UHFFFAOYSA-N 0.000 description 2
- BDSHNNKBWNAZIM-UHFFFAOYSA-N (2,4-dimethylphenyl)hydrazine Chemical compound CC1=CC=C(NN)C(C)=C1 BDSHNNKBWNAZIM-UHFFFAOYSA-N 0.000 description 2
- LZKWWERBNXLGLI-UHFFFAOYSA-N (2,5-dichlorophenyl)hydrazine Chemical compound NNC1=CC(Cl)=CC=C1Cl LZKWWERBNXLGLI-UHFFFAOYSA-N 0.000 description 2
- DZFPIGYCQCPEQN-UHFFFAOYSA-N (2-bromo-4-methylphenyl)hydrazine;hydrochloride Chemical compound Cl.CC1=CC=C(NN)C(Br)=C1 DZFPIGYCQCPEQN-UHFFFAOYSA-N 0.000 description 2
- JHPOWXCLWLEKBY-UHFFFAOYSA-N (2-ethylphenyl)hydrazine Chemical compound CCC1=CC=CC=C1NN JHPOWXCLWLEKBY-UHFFFAOYSA-N 0.000 description 2
- DBJQHFUPMMKBSU-UHFFFAOYSA-N (4-bromo-2-chlorophenyl)hydrazine Chemical compound NNC1=CC=C(Br)C=C1Cl DBJQHFUPMMKBSU-UHFFFAOYSA-N 0.000 description 2
- YTWVOEWDYZBUNY-UHFFFAOYSA-N (4-chloro-2-methylphenyl)hydrazine Chemical compound CC1=CC(Cl)=CC=C1NN YTWVOEWDYZBUNY-UHFFFAOYSA-N 0.000 description 2
- MPZOVJOEZZCBKJ-UHFFFAOYSA-N (5-bromo-2-hydroxyphenyl)-(1-phenylpyrazol-4-yl)methanone Chemical compound OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 MPZOVJOEZZCBKJ-UHFFFAOYSA-N 0.000 description 2
- KKSRYULVYHVSLY-UHFFFAOYSA-N (5-bromo-2-hydroxyphenyl)-[1-(4-methoxyphenyl)pyrazol-4-yl]methanone Chemical compound C1=CC(OC)=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)O)=C1 KKSRYULVYHVSLY-UHFFFAOYSA-N 0.000 description 2
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical group O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 2
- LXKNAUOWEJWGTE-UHFFFAOYSA-N 2-(3-methoxyphenyl)acetonitrile Chemical compound COC1=CC=CC(CC#N)=C1 LXKNAUOWEJWGTE-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- TYGCTVWKTNQSLJ-UHFFFAOYSA-N 2-[4-bromo-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetonitrile Chemical compound BrC1=CC=C(OCC#N)C(C(=O)C2=CN(N=C2)C=2C=CC=CC=2)=C1 TYGCTVWKTNQSLJ-UHFFFAOYSA-N 0.000 description 2
- TUPDIHSNBTUGCL-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,6-diethylphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound CCC1=CC=CC(CC)=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 TUPDIHSNBTUGCL-UHFFFAOYSA-N 0.000 description 2
- ABJDYWHACJDHLM-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-bromophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=CC=2)Br)N=C1 ABJDYWHACJDHLM-UHFFFAOYSA-N 0.000 description 2
- QESPLVPINADVJP-UHFFFAOYSA-N 2-[4-bromo-2-[1-(3-chlorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=C(Cl)C=CC=2)N=C1 QESPLVPINADVJP-UHFFFAOYSA-N 0.000 description 2
- LSZGCUUCQQKNOA-UHFFFAOYSA-N 2-[4-bromo-2-[1-(4-bromophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=CC(Br)=CC=2)N=C1 LSZGCUUCQQKNOA-UHFFFAOYSA-N 0.000 description 2
- CLIVJKSOVQCFOU-UHFFFAOYSA-N 2-[4-bromo-2-[3-(1-phenylcyclopropyl)-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(C2(CC2)C=2C=CC=CC=2)=NO1 CLIVJKSOVQCFOU-UHFFFAOYSA-N 0.000 description 2
- CZTWFAWSRBQUQT-UHFFFAOYSA-N 2-[4-bromo-2-[3-(2,4-dichlorophenyl)-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(C=2C(=CC(Cl)=CC=2)Cl)=NO1 CZTWFAWSRBQUQT-UHFFFAOYSA-N 0.000 description 2
- MTFHDYKMXGXANV-UHFFFAOYSA-N 2-[4-chloro-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 MTFHDYKMXGXANV-UHFFFAOYSA-N 0.000 description 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- KRLKXOLFFQWKPZ-UHFFFAOYSA-N 4-(bromomethyl)pyridine Chemical compound BrCC1=CC=NC=C1 KRLKXOLFFQWKPZ-UHFFFAOYSA-N 0.000 description 2
- FSMYWBQIMDSGQP-UHFFFAOYSA-N 4-oxochromene-3-carbaldehyde Chemical compound C1=CC=C2C(=O)C(C=O)=COC2=C1 FSMYWBQIMDSGQP-UHFFFAOYSA-N 0.000 description 2
- XCKTXKYXKJJGBA-UHFFFAOYSA-N 6-ethyl-4-oxochromene-3-carbaldehyde Chemical compound O1C=C(C=O)C(=O)C2=CC(CC)=CC=C21 XCKTXKYXKJJGBA-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000009137 Behcet syndrome Diseases 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 108091026890 Coding region Proteins 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 102100023688 Eotaxin Human genes 0.000 description 2
- 101710139422 Eotaxin Proteins 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 208000035895 Guillain-Barré syndrome Diseases 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- WQZGKKKJIJFFOK-ZZWDRFIYSA-N L-glucose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-ZZWDRFIYSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 206010049567 Miller Fisher syndrome Diseases 0.000 description 2
- 241001421711 Mithras Species 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 2
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 101100221606 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) COS7 gene Proteins 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 2
- 239000012148 binding buffer Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000002299 complementary DNA Substances 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000010931 ester hydrolysis Methods 0.000 description 2
- NGJROWIAIGCUGO-UHFFFAOYSA-N ethyl 2-(2-acetyl-4-bromophenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(Br)C=C1C(C)=O NGJROWIAIGCUGO-UHFFFAOYSA-N 0.000 description 2
- JPOKVQOQCAYQNJ-UHFFFAOYSA-N ethyl 2-(4-bromo-2-carbamoylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(Br)C=C1C(N)=O JPOKVQOQCAYQNJ-UHFFFAOYSA-N 0.000 description 2
- WYDYPDHKJHGEBD-UHFFFAOYSA-N ethyl 2-[2-(2-bromoacetyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC=C1C(=O)CBr WYDYPDHKJHGEBD-UHFFFAOYSA-N 0.000 description 2
- LLTNRQKCWKFMCB-UHFFFAOYSA-N ethyl 2-[4-bromo-2-(1-pyridin-2-ylpyrazole-4-carbonyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2N=CC=CC=2)N=C1 LLTNRQKCWKFMCB-UHFFFAOYSA-N 0.000 description 2
- RUXXMTNPQLOKFK-UHFFFAOYSA-N ethyl 2-[4-bromo-2-(3-trimethylsilylprop-2-ynoyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(Br)C=C1C(=O)C#C[Si](C)(C)C RUXXMTNPQLOKFK-UHFFFAOYSA-N 0.000 description 2
- QBSXAFQKPMNEAA-UHFFFAOYSA-N ethyl 2-[4-fluoro-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(F)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 QBSXAFQKPMNEAA-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000013604 expression vector Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 210000002443 helper t lymphocyte Anatomy 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 239000007922 nasal spray Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000002687 nonaqueous vehicle Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 2
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- 238000000159 protein binding assay Methods 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 150000003556 thioamides Chemical class 0.000 description 2
- 238000001890 transfection Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 229960000281 trometamol Drugs 0.000 description 2
- CCHJMGDYNLOYKM-UHFFFAOYSA-N (2,6-dimethylphenyl)hydrazine Chemical compound CC1=CC=CC(C)=C1NN CCHJMGDYNLOYKM-UHFFFAOYSA-N 0.000 description 1
- ZPGVNHBXCQUDKE-UHFFFAOYSA-N (2-chloro-6-methylphenyl)hydrazine Chemical compound CC1=CC=CC(Cl)=C1NN ZPGVNHBXCQUDKE-UHFFFAOYSA-N 0.000 description 1
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 1
- PENWGQNPFRRVQI-UHFFFAOYSA-N (2-fluorophenyl)hydrazine Chemical compound NNC1=CC=CC=C1F PENWGQNPFRRVQI-UHFFFAOYSA-N 0.000 description 1
- WTRJNEICFURGNX-UHFFFAOYSA-N (2-hydroxyphenyl)-(1-phenylpyrazol-4-yl)methanone Chemical compound OC1=CC=CC=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 WTRJNEICFURGNX-UHFFFAOYSA-N 0.000 description 1
- SCZGZDLUGUYLRV-UHFFFAOYSA-N (2-methylphenyl)hydrazine Chemical compound CC1=CC=CC=C1NN SCZGZDLUGUYLRV-UHFFFAOYSA-N 0.000 description 1
- CUXIXAPJSZQSIB-UHFFFAOYSA-N (2-methylsulfanylphenyl)hydrazine Chemical compound CSC1=CC=CC=C1NN CUXIXAPJSZQSIB-UHFFFAOYSA-N 0.000 description 1
- NYMGSEDQLNNAEN-UHFFFAOYSA-N (2-phenoxyphenyl)hydrazine Chemical compound NNC1=CC=CC=C1OC1=CC=CC=C1 NYMGSEDQLNNAEN-UHFFFAOYSA-N 0.000 description 1
- YMJSQPNVQRHZDW-UHFFFAOYSA-N (3,4-dichlorophenyl)hydrazine Chemical compound NNC1=CC=C(Cl)C(Cl)=C1 YMJSQPNVQRHZDW-UHFFFAOYSA-N 0.000 description 1
- PESJTQQZJJTNOC-UHFFFAOYSA-N (3-bromophenyl)hydrazine Chemical compound NNC1=CC=CC(Br)=C1 PESJTQQZJJTNOC-UHFFFAOYSA-N 0.000 description 1
- MQBUGTTVELAUOS-UHFFFAOYSA-N (3-chloro-6-hydroxy-2-methylphenyl)-(1-phenylpyrazol-4-yl)methanone Chemical compound CC1=C(Cl)C=CC(O)=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 MQBUGTTVELAUOS-UHFFFAOYSA-N 0.000 description 1
- GFPJLZASIVURDY-UHFFFAOYSA-N (3-chlorophenyl)hydrazine Chemical compound NNC1=CC=CC(Cl)=C1 GFPJLZASIVURDY-UHFFFAOYSA-N 0.000 description 1
- OQANPHBRHBJGNZ-FYJGNVAPSA-N (3e)-6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid Chemical compound C1=CC(=O)C(C(=O)O)=C\C1=N\NC1=CC=C(S(=O)(=O)NC=2N=CC=CC=2)C=C1 OQANPHBRHBJGNZ-FYJGNVAPSA-N 0.000 description 1
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 1
- PVRSIFAEUCUJPK-UHFFFAOYSA-N (4-methoxyphenyl)hydrazine Chemical compound COC1=CC=C(NN)C=C1 PVRSIFAEUCUJPK-UHFFFAOYSA-N 0.000 description 1
- XQMSLSSJGOTTJO-UHFFFAOYSA-N (5-bromo-2-hydroxyphenyl)-(1-pyridin-2-ylpyrazol-4-yl)methanone Chemical compound OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2N=CC=CC=2)N=C1 XQMSLSSJGOTTJO-UHFFFAOYSA-N 0.000 description 1
- HEVRUKPQOSEFKD-UHFFFAOYSA-N (5-chloro-2-hydroxyphenyl)-(1-phenylpyrazol-4-yl)methanone Chemical compound OC1=CC=C(Cl)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 HEVRUKPQOSEFKD-UHFFFAOYSA-N 0.000 description 1
- LUIKVPFJGVQNCR-UHFFFAOYSA-N (5-fluoro-2-hydroxyphenyl)-(1-phenylpyrazol-4-yl)methanone Chemical compound OC1=CC=C(F)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 LUIKVPFJGVQNCR-UHFFFAOYSA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- 150000005071 1,2,4-oxadiazoles Chemical class 0.000 description 1
- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 1
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- 150000005072 1,3,4-oxadiazoles Chemical class 0.000 description 1
- QTZHNPVEFICUMY-UHFFFAOYSA-N 1,3-thiazol-1-ylidenemethanone Chemical class O=C=S1C=CN=C1 QTZHNPVEFICUMY-UHFFFAOYSA-N 0.000 description 1
- JYDHZOIDIWUHDB-UHFFFAOYSA-N 1-(4-phenylpiperidin-4-yl)ethanone;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(C(=O)C)CCNCC1 JYDHZOIDIWUHDB-UHFFFAOYSA-N 0.000 description 1
- HQCCNFFIOWYINW-UHFFFAOYSA-N 1-(5-bromo-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC(Br)=CC=C1O HQCCNFFIOWYINW-UHFFFAOYSA-N 0.000 description 1
- KQNBRMUBPRGXSL-UHFFFAOYSA-N 1-(bromomethyl)-4-chlorobenzene Chemical compound ClC1=CC=C(CBr)C=C1 KQNBRMUBPRGXSL-UHFFFAOYSA-N 0.000 description 1
- WZRKSPFYXUXINF-UHFFFAOYSA-N 1-(bromomethyl)-4-methylbenzene Chemical compound CC1=CC=C(CBr)C=C1 WZRKSPFYXUXINF-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
- QPKFVRWIISEVCW-UHFFFAOYSA-N 1-butane boronic acid Chemical compound CCCCB(O)O QPKFVRWIISEVCW-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- OAXSVEFCBLZGCA-UHFFFAOYSA-N 1-chloro-4-(isocyanatomethyl)benzene Chemical compound ClC1=CC=C(CN=C=O)C=C1 OAXSVEFCBLZGCA-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- ZHFURHRJUWYDKG-UHFFFAOYSA-N 1-phenylcyclopropane-1-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CC1 ZHFURHRJUWYDKG-UHFFFAOYSA-N 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- FUJSJWRORKKPAI-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1Cl FUJSJWRORKKPAI-UHFFFAOYSA-N 0.000 description 1
- VJARIBGMDPJLCL-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)acetonitrile Chemical compound ClC1=CC=C(CC#N)C(Cl)=C1 VJARIBGMDPJLCL-UHFFFAOYSA-N 0.000 description 1
- AOEJUUCUKRUCEF-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)acetonitrile Chemical compound ClC1=CC=CC(Cl)=C1CC#N AOEJUUCUKRUCEF-UHFFFAOYSA-N 0.000 description 1
- KKNGNQGKYUBBKL-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)acetamide Chemical compound NC(=O)CC1=CC=C(F)C=C1Cl KKNGNQGKYUBBKL-UHFFFAOYSA-N 0.000 description 1
- DWJKILXTMUGXOU-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetonitrile Chemical compound COC1=CC=CC=C1CC#N DWJKILXTMUGXOU-UHFFFAOYSA-N 0.000 description 1
- ASLSUMISAQDOOB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1OC ASLSUMISAQDOOB-UHFFFAOYSA-N 0.000 description 1
- OBMYMTSBABEPIB-UHFFFAOYSA-N 2-(3,5-difluorophenyl)acetonitrile Chemical compound FC1=CC(F)=CC(CC#N)=C1 OBMYMTSBABEPIB-UHFFFAOYSA-N 0.000 description 1
- UUNRWZQWCNTSCV-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)acetonitrile Chemical compound COC1=CC(CC#N)=CC(OC)=C1 UUNRWZQWCNTSCV-UHFFFAOYSA-N 0.000 description 1
- GTIKLPYCSAMPNG-UHFFFAOYSA-N 2-(3-chlorophenyl)acetonitrile Chemical compound ClC1=CC=CC(CC#N)=C1 GTIKLPYCSAMPNG-UHFFFAOYSA-N 0.000 description 1
- HPKKEDGOBIXMHS-UHFFFAOYSA-N 2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(N)=O)=C1 HPKKEDGOBIXMHS-UHFFFAOYSA-N 0.000 description 1
- QHCDYIRWTPEABF-UHFFFAOYSA-N 2-(4-chlorophenyl)ethanethioamide Chemical compound NC(=S)CC1=CC=C(Cl)C=C1 QHCDYIRWTPEABF-UHFFFAOYSA-N 0.000 description 1
- JHQBLYITVCBGTO-UHFFFAOYSA-N 2-(4-fluorophenyl)acetonitrile Chemical compound FC1=CC=C(CC#N)C=C1 JHQBLYITVCBGTO-UHFFFAOYSA-N 0.000 description 1
- OLKQIWCQICCYQS-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(CC(N)=O)C=C1 OLKQIWCQICCYQS-UHFFFAOYSA-N 0.000 description 1
- PACGLQCRGWFBJH-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1 PACGLQCRGWFBJH-UHFFFAOYSA-N 0.000 description 1
- RNHKXHKUKJXLAU-UHFFFAOYSA-N 2-(4-methylphenyl)acetonitrile Chemical compound CC1=CC=C(CC#N)C=C1 RNHKXHKUKJXLAU-UHFFFAOYSA-N 0.000 description 1
- SACJNJRXFCNGRM-UHFFFAOYSA-N 2-[2,4-dichloro-6-(1-phenylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=C(Cl)C=C(Cl)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 SACJNJRXFCNGRM-UHFFFAOYSA-N 0.000 description 1
- OVQOFAFHEQPFBG-UHFFFAOYSA-N 2-[2-(2-benzyl-1,3-oxazol-4-yl)-4-bromophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=COC(CC=2C=CC=CC=2)=N1 OVQOFAFHEQPFBG-UHFFFAOYSA-N 0.000 description 1
- QXDCZSJGEUSERL-UHFFFAOYSA-N 2-[2-(trifluoromethyl)phenyl]acetonitrile Chemical compound FC(F)(F)C1=CC=CC=C1CC#N QXDCZSJGEUSERL-UHFFFAOYSA-N 0.000 description 1
- DZHNLZAFXDFGSK-UHFFFAOYSA-N 2-[2-[1-(2,6-dichlorophenyl)pyrazole-4-carbonyl]-4-ethylphenoxy]acetic acid Chemical compound CCC1=CC=C(OCC(O)=O)C(C(=O)C2=CN(N=C2)C=2C(=CC=CC=2Cl)Cl)=C1 DZHNLZAFXDFGSK-UHFFFAOYSA-N 0.000 description 1
- MSBJLGNSRGUBFS-UHFFFAOYSA-N 2-[2-[1-(2-bromophenyl)pyrazole-4-carbonyl]-4-nitrophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CN(C=2C(=CC=CC=2)Br)N=C1 MSBJLGNSRGUBFS-UHFFFAOYSA-N 0.000 description 1
- QLCCLVILESTJNX-UHFFFAOYSA-N 2-[2-[1-(2-chlorophenyl)pyrazole-4-carbonyl]-4-nitrophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CN(C=2C(=CC=CC=2)Cl)N=C1 QLCCLVILESTJNX-UHFFFAOYSA-N 0.000 description 1
- JPWGKUYDBJKQPX-UHFFFAOYSA-N 2-[2-[1-(2-chlorophenyl)pyrazole-4-carbonyl]-4-propan-2-ylphenoxy]acetic acid Chemical compound CC(C)C1=CC=C(OCC(O)=O)C(C(=O)C2=CN(N=C2)C=2C(=CC=CC=2)Cl)=C1 JPWGKUYDBJKQPX-UHFFFAOYSA-N 0.000 description 1
- KWFYURNFMQCZCB-UHFFFAOYSA-N 2-[2-[3-[(4-acetamidophenyl)methyl]-1,2,4-oxadiazol-5-yl]-4-bromophenoxy]acetic acid Chemical compound C1=CC(NC(=O)C)=CC=C1CC1=NOC(C=2C(=CC=C(Br)C=2)OCC(O)=O)=N1 KWFYURNFMQCZCB-UHFFFAOYSA-N 0.000 description 1
- HUHGPYXAVBJSJV-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyethyl)-1,3,5-triazinan-1-yl]ethanol Chemical compound OCCN1CN(CCO)CN(CCO)C1 HUHGPYXAVBJSJV-UHFFFAOYSA-N 0.000 description 1
- YVBANBQEFCQYAS-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C=2C=CC(Cl)=CC=2)C=C1C(=O)C(=C1)C=NN1C1=CC=CC=C1 YVBANBQEFCQYAS-UHFFFAOYSA-N 0.000 description 1
- LYFCAROXYJTUQF-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]acetonitrile Chemical compound FC(F)(F)OC1=CC=C(CC#N)C=C1 LYFCAROXYJTUQF-UHFFFAOYSA-N 0.000 description 1
- BTJWNTQLKJTTGD-UHFFFAOYSA-N 2-[4-amino-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound NC1=CC=C(OCC(O)=O)C(C(=O)C2=CN(N=C2)C=2C=CC=CC=2)=C1 BTJWNTQLKJTTGD-UHFFFAOYSA-N 0.000 description 1
- FPUHOPCIQOLVJH-UHFFFAOYSA-N 2-[4-bromo-2-(1-hydroxy-3-trimethylsilylprop-2-ynyl)phenoxy]acetic acid Chemical compound C[Si](C)(C)C#CC(O)C1=CC(Br)=CC=C1OCC(O)=O FPUHOPCIQOLVJH-UHFFFAOYSA-N 0.000 description 1
- OJZJVPSLUFURNS-UHFFFAOYSA-N 2-[4-bromo-2-(2-phenyl-1,3-oxazol-4-yl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=COC(C=2C=CC=CC=2)=N1 OJZJVPSLUFURNS-UHFFFAOYSA-N 0.000 description 1
- SBVXCZJKJMXZOZ-UHFFFAOYSA-N 2-[4-bromo-2-(2-phenyl-1,3-thiazole-5-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN=C(C=2C=CC=CC=2)S1 SBVXCZJKJMXZOZ-UHFFFAOYSA-N 0.000 description 1
- AQSRSVWMSQIBHS-UHFFFAOYSA-N 2-[4-bromo-2-(3-phenyl-1,2,4-oxadiazol-5-yl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(C=2C=CC=CC=2)=NO1 AQSRSVWMSQIBHS-UHFFFAOYSA-N 0.000 description 1
- VTZWTDGVVKEGDF-UHFFFAOYSA-N 2-[4-bromo-2-(3-phenyl-1,2-oxazole-5-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CC(C=2C=CC=CC=2)=NO1 VTZWTDGVVKEGDF-UHFFFAOYSA-N 0.000 description 1
- ZEFYKISIVVUHEP-UHFFFAOYSA-N 2-[4-bromo-2-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(C=2N=CC=CC=2)=NO1 ZEFYKISIVVUHEP-UHFFFAOYSA-N 0.000 description 1
- RUJXLSBAHUZVSP-UHFFFAOYSA-N 2-[4-bromo-2-(5-phenyl-1,2,4-oxadiazol-3-yl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NOC(C=2C=CC=CC=2)=N1 RUJXLSBAHUZVSP-UHFFFAOYSA-N 0.000 description 1
- FFWUJZPKLMPXAT-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,4-dibromophenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC(Br)=CC=2)Br)N=C1 FFWUJZPKLMPXAT-UHFFFAOYSA-N 0.000 description 1
- YOLNLRRFMCSTMV-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,5-dichlorophenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC=C(Cl)C=2)Cl)N=C1 YOLNLRRFMCSTMV-UHFFFAOYSA-N 0.000 description 1
- XHEXJINGFJOKNM-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2,6-dimethylphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(C)=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 XHEXJINGFJOKNM-UHFFFAOYSA-N 0.000 description 1
- WZHZQVVRTOGXMH-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-chloro-6-methylphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(Cl)=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 WZHZQVVRTOGXMH-UHFFFAOYSA-N 0.000 description 1
- QOLHWJBHOYJVRQ-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-ethoxyphenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound CCOC1=CC=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OC(C)C(O)=O)=C1 QOLHWJBHOYJVRQ-UHFFFAOYSA-N 0.000 description 1
- XLQKTAXDTJSEIE-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-methoxyphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound COC1=CC=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 XLQKTAXDTJSEIE-UHFFFAOYSA-N 0.000 description 1
- LUQJBKLQRDLIIG-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-methoxyphenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound COC1=CC=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OC(C)C(O)=O)=C1 LUQJBKLQRDLIIG-UHFFFAOYSA-N 0.000 description 1
- BKBQMGQWNFRFSV-UHFFFAOYSA-N 2-[4-bromo-2-[1-(2-propan-2-ylphenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound CC(C)C1=CC=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OC(C)C(O)=O)=C1 BKBQMGQWNFRFSV-UHFFFAOYSA-N 0.000 description 1
- KFAFGRPITMCCBO-UHFFFAOYSA-N 2-[4-bromo-2-[1-(3,4-dichlorophenyl)pyrazole-4-carbonyl]phenoxy]propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=C(Cl)C(Cl)=CC=2)N=C1 KFAFGRPITMCCBO-UHFFFAOYSA-N 0.000 description 1
- IJDZLNQGKXRXSO-UHFFFAOYSA-N 2-[4-bromo-2-[1-(3-bromophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=C(Br)C=CC=2)N=C1 IJDZLNQGKXRXSO-UHFFFAOYSA-N 0.000 description 1
- YOBMCDVFDDJFFV-UHFFFAOYSA-N 2-[4-bromo-2-[1-(4-bromo-2-chlorophenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C(=CC(Br)=CC=2)Cl)N=C1 YOBMCDVFDDJFFV-UHFFFAOYSA-N 0.000 description 1
- ABALWRHCXZMMAL-UHFFFAOYSA-N 2-[4-bromo-2-[1-(4-bromo-2-ethylphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound CCC1=CC(Br)=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 ABALWRHCXZMMAL-UHFFFAOYSA-N 0.000 description 1
- IPDACYXTBUWPEL-UHFFFAOYSA-N 2-[4-bromo-2-[1-(4-methoxyphenyl)pyrazole-4-carbonyl]phenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1N1N=CC(C(=O)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 IPDACYXTBUWPEL-UHFFFAOYSA-N 0.000 description 1
- MQTGZSWMTLJIII-UHFFFAOYSA-N 2-[4-bromo-2-[2-(3-methoxyphenyl)-1,3-oxazol-4-yl]phenoxy]acetic acid Chemical compound COC1=CC=CC(C=2OC=C(N=2)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 MQTGZSWMTLJIII-UHFFFAOYSA-N 0.000 description 1
- XALOSPXQUWAQJT-UHFFFAOYSA-N 2-[4-bromo-2-[2-(4-methoxyphenyl)-1,3-oxazol-4-yl]phenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C(=CC=C(Br)C=2)OCC(O)=O)=CO1 XALOSPXQUWAQJT-UHFFFAOYSA-N 0.000 description 1
- PRANLZFTMNLYCJ-UHFFFAOYSA-N 2-[4-bromo-2-[2-[(2-chloro-4-fluorophenyl)methyl]-1,3-oxazol-4-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=COC(CC=2C(=CC(F)=CC=2)Cl)=N1 PRANLZFTMNLYCJ-UHFFFAOYSA-N 0.000 description 1
- GAAZVLGIBFBCCI-UHFFFAOYSA-N 2-[4-bromo-2-[2-[(3-methoxyphenyl)methyl]-1,3-oxazol-4-yl]phenoxy]acetic acid Chemical compound COC1=CC=CC(CC=2OC=C(N=2)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 GAAZVLGIBFBCCI-UHFFFAOYSA-N 0.000 description 1
- KCMKSFDEQZVZNF-UHFFFAOYSA-N 2-[4-bromo-2-[3-(2-chlorophenyl)-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(C=2C(=CC=CC=2)Cl)=NO1 KCMKSFDEQZVZNF-UHFFFAOYSA-N 0.000 description 1
- KYUDOTPHZGPXTB-UHFFFAOYSA-N 2-[4-bromo-2-[3-(2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound COC1=CC=CC=C1C1=NOC(C=2C(=CC=C(Br)C=2)OCC(O)=O)=N1 KYUDOTPHZGPXTB-UHFFFAOYSA-N 0.000 description 1
- FGDSMBLWOIPCGC-UHFFFAOYSA-N 2-[4-bromo-2-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(C=2C=C(Cl)C=CC=2)=NO1 FGDSMBLWOIPCGC-UHFFFAOYSA-N 0.000 description 1
- GAZYTDIYPUCQRP-UHFFFAOYSA-N 2-[4-bromo-2-[3-(3-methoxyphenyl)-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound COC1=CC=CC(C=2N=C(ON=2)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 GAZYTDIYPUCQRP-UHFFFAOYSA-N 0.000 description 1
- ZVAVUDKJOCDNFX-UHFFFAOYSA-N 2-[4-bromo-2-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(C=2C=CC(Cl)=CC=2)=NO1 ZVAVUDKJOCDNFX-UHFFFAOYSA-N 0.000 description 1
- IEYUEAWAOCCAKN-UHFFFAOYSA-N 2-[4-bromo-2-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(C=2C=CC(F)=CC=2)=NO1 IEYUEAWAOCCAKN-UHFFFAOYSA-N 0.000 description 1
- CIBDGZPSIJRAOC-UHFFFAOYSA-N 2-[4-bromo-2-[3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=NOC(C=2C(=CC=C(Br)C=2)OCC(O)=O)=N1 CIBDGZPSIJRAOC-UHFFFAOYSA-N 0.000 description 1
- LNQFETNHOMQXMD-UHFFFAOYSA-N 2-[4-bromo-2-[3-[(2,6-dichlorophenyl)methyl]-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(CC=2C(=CC=CC=2Cl)Cl)=NO1 LNQFETNHOMQXMD-UHFFFAOYSA-N 0.000 description 1
- FIZOOZWMMCCCCE-UHFFFAOYSA-N 2-[4-bromo-2-[3-[(2-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(CC=2C(=CC=CC=2)Cl)=NO1 FIZOOZWMMCCCCE-UHFFFAOYSA-N 0.000 description 1
- GIOZHSJQDSUABO-UHFFFAOYSA-N 2-[4-bromo-2-[3-[(2-methoxyphenyl)methyl]-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound COC1=CC=CC=C1CC1=NOC(C=2C(=CC=C(Br)C=2)OCC(O)=O)=N1 GIOZHSJQDSUABO-UHFFFAOYSA-N 0.000 description 1
- WLGXCONFCBPPQM-UHFFFAOYSA-N 2-[4-bromo-2-[3-[(3,4-dimethoxyphenyl)methyl]-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NOC(C=2C(=CC=C(Br)C=2)OCC(O)=O)=N1 WLGXCONFCBPPQM-UHFFFAOYSA-N 0.000 description 1
- ITLLWKVWBUOKSM-UHFFFAOYSA-N 2-[4-bromo-2-[3-[(3-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(CC=2C=C(Cl)C=CC=2)=NO1 ITLLWKVWBUOKSM-UHFFFAOYSA-N 0.000 description 1
- MTAVRJZCXSKPEN-UHFFFAOYSA-N 2-[4-bromo-2-[3-[(3-methoxyphenyl)methyl]-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound COC1=CC=CC(CC=2N=C(ON=2)C=2C(=CC=C(Br)C=2)OCC(O)=O)=C1 MTAVRJZCXSKPEN-UHFFFAOYSA-N 0.000 description 1
- LPFQOHWKXHMMHH-UHFFFAOYSA-N 2-[4-bromo-2-[3-[(4-methoxyphenyl)methyl]-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1CC1=NOC(C=2C(=CC=C(Br)C=2)OCC(O)=O)=N1 LPFQOHWKXHMMHH-UHFFFAOYSA-N 0.000 description 1
- IZBKYALIEFDOHO-UHFFFAOYSA-N 2-[4-bromo-2-[3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(C=2C=CC(OC(F)(F)F)=CC=2)=NO1 IZBKYALIEFDOHO-UHFFFAOYSA-N 0.000 description 1
- XLLSBNCHZWZMBM-UHFFFAOYSA-N 2-[4-bromo-2-[3-[[2-(trifluoromethyl)phenyl]methyl]-1,2,4-oxadiazol-5-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NC(CC=2C(=CC=CC=2)C(F)(F)F)=NO1 XLLSBNCHZWZMBM-UHFFFAOYSA-N 0.000 description 1
- XPDOFTHHYUBGFM-UHFFFAOYSA-N 2-[4-bromo-2-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1C1=NOC(C=2C=C(Cl)C=CC=2)=N1 XPDOFTHHYUBGFM-UHFFFAOYSA-N 0.000 description 1
- UKANISIXORMXEY-UHFFFAOYSA-N 2-[4-bromo-2-[5-[4-(4-methoxyphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenoxy]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=2ON=C(N=2)C=2C(=CC=C(Br)C=2)OCC(O)=O)C=C1 UKANISIXORMXEY-UHFFFAOYSA-N 0.000 description 1
- PTRORACINFTMMN-UHFFFAOYSA-N 2-[4-bromo-2-[[2,4-dioxo-3-(pyridin-4-ylmethyl)-1,3-thiazolidin-5-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1CC1C(=O)N(CC=2C=CN=CC=2)C(=O)S1 PTRORACINFTMMN-UHFFFAOYSA-N 0.000 description 1
- LGECCCSZSFXRNV-UHFFFAOYSA-N 2-[4-bromo-2-[[3-[(2-chlorophenyl)methyl]-5-methyl-2,4-dioxo-1,3-thiazolidin-5-yl]methyl]phenoxy]acetic acid Chemical compound S1C(=O)N(CC=2C(=CC=CC=2)Cl)C(=O)C1(C)CC1=CC(Br)=CC=C1OCC(O)=O LGECCCSZSFXRNV-UHFFFAOYSA-N 0.000 description 1
- BELIANUZLQOQQN-UHFFFAOYSA-N 2-[4-bromo-2-[[3-[(4-chlorophenyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1CC1C(=O)N(CC=2C=CC(Cl)=CC=2)C(=O)S1 BELIANUZLQOQQN-UHFFFAOYSA-N 0.000 description 1
- QDDILWDVBLTEMI-UHFFFAOYSA-N 2-[4-chloro-3-methyl-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound CC1=C(Cl)C=CC(OCC(O)=O)=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 QDDILWDVBLTEMI-UHFFFAOYSA-N 0.000 description 1
- KVBPTPLNSFDVHJ-UHFFFAOYSA-N 2-[4-ethoxy-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound CCOC1=CC=C(OCC(O)=O)C(C(=O)C2=CN(N=C2)C=2C=CC=CC=2)=C1 KVBPTPLNSFDVHJ-UHFFFAOYSA-N 0.000 description 1
- GNHNTUNNFVREOV-UHFFFAOYSA-N 2-[4-fluoro-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(F)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 GNHNTUNNFVREOV-UHFFFAOYSA-N 0.000 description 1
- HODPNPWIMWTWCD-UHFFFAOYSA-N 2-[4-methyl-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound CC1=CC=C(OCC(O)=O)C(C(=O)C2=CN(N=C2)C=2C=CC=CC=2)=C1 HODPNPWIMWTWCD-UHFFFAOYSA-N 0.000 description 1
- AZWQUUTUJJOAIZ-UHFFFAOYSA-N 2-[4-nitro-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 AZWQUUTUJJOAIZ-UHFFFAOYSA-N 0.000 description 1
- GBCOHXIVTPCPMJ-UHFFFAOYSA-N 2-[4-phenyl-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(C=2C=CC=CC=2)C=C1C(=O)C(=C1)C=NN1C1=CC=CC=C1 GBCOHXIVTPCPMJ-UHFFFAOYSA-N 0.000 description 1
- FLAYZKKEOIAALB-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1 FLAYZKKEOIAALB-UHFFFAOYSA-N 0.000 description 1
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
- HINFZKWHKTZDQX-UHFFFAOYSA-N 2-hydrazinylbenzonitrile Chemical compound NNC1=CC=CC=C1C#N HINFZKWHKTZDQX-UHFFFAOYSA-N 0.000 description 1
- FSTPMFASNVISBU-UHFFFAOYSA-N 2-methoxybenzonitrile Chemical compound COC1=CC=CC=C1C#N FSTPMFASNVISBU-UHFFFAOYSA-N 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- JBSZOMKCYSPCTR-UHFFFAOYSA-N 3,5-bis(trifluoromethoxy)benzonitrile Chemical compound FC(F)(F)OC1=CC(OC(F)(F)F)=CC(C#N)=C1 JBSZOMKCYSPCTR-UHFFFAOYSA-N 0.000 description 1
- OGOBINRVCUWLGN-UHFFFAOYSA-N 3-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=CC(C#N)=C1 OGOBINRVCUWLGN-UHFFFAOYSA-N 0.000 description 1
- UTKYKRNUXMMADC-UHFFFAOYSA-N 3-amino-3-oxo-2-(2-phenylphenoxy)propanoic acid Chemical class NC(=O)C(C(O)=O)OC1=CC=CC=C1C1=CC=CC=C1 UTKYKRNUXMMADC-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- WBUOVKBZJOIOAE-UHFFFAOYSA-N 3-chlorobenzonitrile Chemical compound ClC1=CC=CC(C#N)=C1 WBUOVKBZJOIOAE-UHFFFAOYSA-N 0.000 description 1
- VKPLPDIMEREJJF-UHFFFAOYSA-N 3-methoxybenzamide Chemical compound COC1=CC=CC(C(N)=O)=C1 VKPLPDIMEREJJF-UHFFFAOYSA-N 0.000 description 1
- KLXSUMLEPNAZFK-UHFFFAOYSA-N 3-methoxybenzonitrile Chemical compound COC1=CC=CC(C#N)=C1 KLXSUMLEPNAZFK-UHFFFAOYSA-N 0.000 description 1
- DRNJIKRLQJRKMM-UHFFFAOYSA-N 4-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=C(C#N)C=C1 DRNJIKRLQJRKMM-UHFFFAOYSA-N 0.000 description 1
- BLNVISNJTIRAHF-UHFFFAOYSA-N 4-chlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C=C1 BLNVISNJTIRAHF-UHFFFAOYSA-N 0.000 description 1
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 1
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 description 1
- YKFAFWKDOSYQIP-UHFFFAOYSA-N 4-ethylbenzamide Chemical compound CCC1=CC=C(C(N)=O)C=C1 YKFAFWKDOSYQIP-UHFFFAOYSA-N 0.000 description 1
- AEKVBBNGWBBYLL-UHFFFAOYSA-N 4-fluorobenzonitrile Chemical compound FC1=CC=C(C#N)C=C1 AEKVBBNGWBBYLL-UHFFFAOYSA-N 0.000 description 1
- GUCPYIYFQVTFSI-UHFFFAOYSA-N 4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1 GUCPYIYFQVTFSI-UHFFFAOYSA-N 0.000 description 1
- XDJAAZYHCCRJOK-UHFFFAOYSA-N 4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1 XDJAAZYHCCRJOK-UHFFFAOYSA-N 0.000 description 1
- FRRYMYQANNFABF-UHFFFAOYSA-N 4-oxo-6-propan-2-ylchromene-3-carbaldehyde Chemical compound O1C=C(C=O)C(=O)C2=CC(C(C)C)=CC=C21 FRRYMYQANNFABF-UHFFFAOYSA-N 0.000 description 1
- LWZMEMOPULJQIN-UHFFFAOYSA-N 4-oxo-7-(4-phenylphenyl)chromene-3-carbaldehyde Chemical compound C=1C=C2C(=O)C(C=O)=COC2=CC=1C(C=C1)=CC=C1C1=CC=CC=C1 LWZMEMOPULJQIN-UHFFFAOYSA-N 0.000 description 1
- UYHCIOZMFCLUDP-UHFFFAOYSA-N 4-phenoxybenzonitrile Chemical compound C1=CC(C#N)=CC=C1OC1=CC=CC=C1 UYHCIOZMFCLUDP-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- MKKSTJKBKNCMRV-UHFFFAOYSA-N 5-bromo-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Br)C=C1C=O MKKSTJKBKNCMRV-UHFFFAOYSA-N 0.000 description 1
- MRMOPHYFXXZTFN-UHFFFAOYSA-N 5-bromo-2-hydroxybenzamide Chemical compound NC(=O)C1=CC(Br)=CC=C1O MRMOPHYFXXZTFN-UHFFFAOYSA-N 0.000 description 1
- NOYHUALJWSACLP-UHFFFAOYSA-N 6-ethoxy-4-oxochromene-3-carbaldehyde Chemical compound O1C=C(C=O)C(=O)C2=CC(OCC)=CC=C21 NOYHUALJWSACLP-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
- 235000019489 Almond oil Nutrition 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
- 229910014585 C2-Ce Inorganic materials 0.000 description 1
- 208000020446 Cardiac disease Diseases 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- 108020004705 Codon Proteins 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- 108091006027 G proteins Proteins 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 101000632319 Homo sapiens Septin-7 Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 108060001084 Luciferase Proteins 0.000 description 1
- 239000005089 Luciferase Substances 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 1
- 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 1
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 1
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 description 1
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
- 101000702488 Rattus norvegicus High affinity cationic amino acid transporter 1 Proteins 0.000 description 1
- 108010052090 Renilla Luciferases Proteins 0.000 description 1
- 102100027981 Septin-7 Human genes 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- 102100037346 Substance-P receptor Human genes 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 102000003141 Tachykinin Human genes 0.000 description 1
- 210000004241 Th2 cell Anatomy 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- DNOYOQWVIBGWPG-UHFFFAOYSA-N [2-(trifluoromethoxy)phenyl]hydrazine Chemical compound NNC1=CC=CC=C1OC(F)(F)F DNOYOQWVIBGWPG-UHFFFAOYSA-N 0.000 description 1
- JSWQDLBFVSTSIW-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=CC=C1C(F)(F)F JSWQDLBFVSTSIW-UHFFFAOYSA-N 0.000 description 1
- RSESUCWJKLHXEZ-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=CC(C(F)(F)F)=C1 RSESUCWJKLHXEZ-UHFFFAOYSA-N 0.000 description 1
- GWFWCTYACJWQKP-UHFFFAOYSA-N [4-(trifluoromethoxy)phenyl]hydrazine Chemical compound NNC1=CC=C(OC(F)(F)F)C=C1 GWFWCTYACJWQKP-UHFFFAOYSA-N 0.000 description 1
- DBNLGTYGKCMLLR-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=C(C(F)(F)F)C=C1 DBNLGTYGKCMLLR-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 150000001543 aryl boronic acids Chemical class 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- 239000012131 assay buffer Substances 0.000 description 1
- AXLOCHLTNQDFFS-BESJYZOMSA-N azastene Chemical class C([C@H]1[C@@H]2CC[C@@]([C@]2(CC[C@@H]1[C@@]1(C)C2)C)(O)C)C=C1C(C)(C)C1=C2C=NO1 AXLOCHLTNQDFFS-BESJYZOMSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 210000003651 basophil Anatomy 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 229940125388 beta agonist Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000020411 cell activation Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002975 chemoattractant Substances 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 229960003260 chlorhexidine Drugs 0.000 description 1
- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 229940111134 coxibs Drugs 0.000 description 1
- 229960000265 cromoglicic acid Drugs 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013211 curve analysis Methods 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical class C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000002988 disease modifying antirheumatic drug Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- WKTFAPPNWGMLNE-UHFFFAOYSA-N ethyl 2-[2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 WKTFAPPNWGMLNE-UHFFFAOYSA-N 0.000 description 1
- TYUKZDYENIVMRA-UHFFFAOYSA-N ethyl 2-[4-bromo-2-(1-hydroxy-3-trimethylsilylprop-2-ynyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(Br)C=C1C(O)C#C[Si](C)(C)C TYUKZDYENIVMRA-UHFFFAOYSA-N 0.000 description 1
- OMYVREZHODJAIK-UHFFFAOYSA-N ethyl 2-[4-bromo-2-[1-(4-methoxyphenyl)pyrazole-4-carbonyl]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(Br)C=C1C(=O)C1=CN(C=2C=CC(OC)=CC=2)N=C1 OMYVREZHODJAIK-UHFFFAOYSA-N 0.000 description 1
- CYVHPUYRQVVRQD-UHFFFAOYSA-N ethyl 2-[4-nitro-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CN(C=2C=CC=CC=2)N=C1 CYVHPUYRQVVRQD-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 108020001507 fusion proteins Proteins 0.000 description 1
- 102000037865 fusion proteins Human genes 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 229960002518 gentamicin Drugs 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229940076085 gold Drugs 0.000 description 1
- 210000000224 granular leucocyte Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 229960003943 hypromellose Drugs 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- OEXHQOGQTVQTAT-JRNQLAHRSA-N ipratropium Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 OEXHQOGQTVQTAT-JRNQLAHRSA-N 0.000 description 1
- 229960001888 ipratropium Drugs 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
- 238000005304 joining Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229940065725 leukotriene receptor antagonists for obstructive airway diseases Drugs 0.000 description 1
- 239000003199 leukotriene receptor blocking agent Substances 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 238000013332 literature search Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical class [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 235000012254 magnesium hydroxide Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- JAVRNIFMYIJXIE-UHFFFAOYSA-N methyl 2-chlorobenzoate Chemical compound COC(=O)C1=CC=CC=C1Cl JAVRNIFMYIJXIE-UHFFFAOYSA-N 0.000 description 1
- XRDRKVPNHIWTBX-UHFFFAOYSA-N methyl 3-chlorobenzoate Chemical compound COC(=O)C1=CC=CC(Cl)=C1 XRDRKVPNHIWTBX-UHFFFAOYSA-N 0.000 description 1
- YJOVQAHQGZBWIU-UHFFFAOYSA-N methyl 4-(4-methoxyphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OC)C=C1 YJOVQAHQGZBWIU-UHFFFAOYSA-N 0.000 description 1
- LXNFVVDCCWUUKC-UHFFFAOYSA-N methyl 4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1 LXNFVVDCCWUUKC-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000007758 minimum essential medium Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- KZPIGDPAEMMVKL-UHFFFAOYSA-N n-[2-(2h-tetrazol-5-ylmethoxy)phenyl]benzamide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1OCC=1N=NNN=1 KZPIGDPAEMMVKL-UHFFFAOYSA-N 0.000 description 1
- SPAOQNOLRMENDZ-UHFFFAOYSA-N n-[4-(cyanomethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(CC#N)C=C1 SPAOQNOLRMENDZ-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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 229960004398 nedocromil Drugs 0.000 description 1
- RQTOOFIXOKYGAN-UHFFFAOYSA-N nedocromil Chemical compound CCN1C(C(O)=O)=CC(=O)C2=C1C(CCC)=C1OC(C(O)=O)=CC(=O)C1=C2 RQTOOFIXOKYGAN-UHFFFAOYSA-N 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 description 1
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940096826 phenylmercuric acetate Drugs 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000036515 potency Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical compound NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 108091008146 restriction endonucleases Proteins 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 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
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 229960001940 sulfasalazine Drugs 0.000 description 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 108060008037 tachykinin Proteins 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
- 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
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
-
- 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
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
-
- 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
-
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/34—Oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
- Otolaryngology (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0412198A GB0412198D0 (en) | 2004-05-29 | 2004-05-29 | Medicinal use of receptor ligands |
| GB0414196A GB0414196D0 (en) | 2004-06-24 | 2004-06-24 | Medicinal use of receptor ligands |
| GB0424018A GB0424018D0 (en) | 2004-10-29 | 2004-10-29 | Medicinal use of receptor ligands |
| PCT/EP2005/005884 WO2005115382A1 (en) | 2004-05-29 | 2005-05-30 | Crth2 receptor ligands for medicinal uses |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL179694A0 IL179694A0 (en) | 2008-03-20 |
| IL179694A true IL179694A (en) | 2012-09-24 |
Family
ID=34993084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL179694A IL179694A (en) | 2004-05-29 | 2006-11-29 | Use of crth2 receptor ligands for the preparation of a pharmaceutical composition, some such ligands and pharmaceutical composition comprising the ligand |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US8022063B2 (enExample) |
| EP (2) | EP2336113A1 (enExample) |
| JP (1) | JP2008500991A (enExample) |
| KR (1) | KR20070045153A (enExample) |
| AU (1) | AU2005247110B2 (enExample) |
| BR (1) | BRPI0511676A (enExample) |
| CA (1) | CA2568766A1 (enExample) |
| CR (1) | CR8838A (enExample) |
| EA (1) | EA014729B1 (enExample) |
| IL (1) | IL179694A (enExample) |
| MX (1) | MXPA06013912A (enExample) |
| NO (1) | NO20066048L (enExample) |
| NZ (1) | NZ551810A (enExample) |
| WO (1) | WO2005115382A1 (enExample) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0301010D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SA04250253B1 (ar) | 2003-08-21 | 2009-11-10 | استرازينيكا ايه بي | احماض فينوكسي اسيتيك مستبدلة باعتبارها مركبات صيدلانية لعلاج الامراض التنفسية مثل الربو ومرض الانسداد الرئوي المزمن |
| GB0415320D0 (en) | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
| GB0418830D0 (en) | 2004-08-24 | 2004-09-22 | Astrazeneca Ab | Novel compounds |
| GB0422057D0 (en) * | 2004-10-05 | 2004-11-03 | Astrazeneca Ab | Novel compounds |
| ATE517085T1 (de) * | 2004-11-23 | 2011-08-15 | Astrazeneca Ab | Zur behandlung von atemwegserkrankungen geeignete phenoxyessigsäurederivate |
| CA2622000C (en) * | 2005-09-30 | 2014-01-21 | Argenta Discovery Limited | Quinolines and their therapeutic use |
| TW200745003A (en) | 2005-10-06 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| US8148572B2 (en) | 2005-10-06 | 2012-04-03 | Astrazeneca Ab | Compounds |
| WO2007062678A1 (en) * | 2005-11-29 | 2007-06-07 | 7Tm Pharma A/S | Phenoxyacetic acid derivatives as crth2 receptor ligands |
| GB0524428D0 (en) * | 2005-11-30 | 2006-01-11 | 7Tm Pharma As | Medicinal use of receptor ligands |
| KR101470659B1 (ko) | 2006-09-07 | 2014-12-08 | 액테리온 파마슈티칼 리미티드 | 면역조절제로서 피리딘-4-일 유도체 |
| US8288554B2 (en) | 2006-09-08 | 2012-10-16 | Actelion Pharmaceuticals Ltd. | Pyridin-3-yl derivatives as immunomodulating agents |
| EP2069318B1 (en) | 2006-09-21 | 2012-09-12 | Actelion Pharmaceuticals Ltd. | Phenyl derivatives and their use as immunomodulators |
| WO2008049864A1 (en) * | 2006-10-25 | 2008-05-02 | Neurosearch A/S | Oxadiazole and thiadiazole compounds and their use as nicotinic acetylcholine receptor modulators |
| ES2383239T3 (es) | 2006-12-14 | 2012-06-19 | Astellas Pharma Inc. | Compuestos de ácidos policíclicos útiles como antagonistas de CRTH2 y como agentes antialérgicos |
| MX2009009597A (es) | 2007-03-16 | 2009-09-16 | Actelion Pharmaceuticals Ltd | Derivados de amino-piridina como agonistas del receptor s1p1/edg1. |
| UA100983C2 (ru) | 2007-07-05 | 2013-02-25 | Астразенека Аб | Бифенилоксипропановая кислота как модулятор crth2 и интермедиаты |
| CN102648198B (zh) | 2007-08-17 | 2015-04-01 | 埃科特莱茵药品有限公司 | 作为s1p1/edg1受体调节剂的吡啶衍生物 |
| MX2010003614A (es) | 2007-10-04 | 2010-04-21 | Merck Serono Sa | Compuestos de diarilo oxadiazol. |
| CA2696863C (en) * | 2007-10-04 | 2016-10-18 | Anna Quattropani | Oxadiazole derivatives |
| BRPI0818804A2 (pt) | 2007-11-01 | 2015-04-22 | Actelion Pharmaceuticals Ltd | Composto derivado de pirimidina, composição farmacêutica que o compreende e uso desse composto. |
| EP2327693B9 (en) | 2007-12-14 | 2012-10-24 | Pulmagen Therapeutics (Asthma) Limited | Indoles and their therapeutic use |
| WO2009082398A1 (en) * | 2007-12-21 | 2009-07-02 | University Of Notre Dame Du Lac | Antibacterial compounds and methods of using same |
| EP2262782B1 (en) | 2008-03-07 | 2012-07-04 | Actelion Pharmaceuticals Ltd. | Novel aminomethyl benzene derivatives |
| CN104965068B (zh) | 2008-05-09 | 2017-12-08 | 希森美康株式会社 | 血液分析装置,血液分析方法及溶血剂 |
| US8138208B2 (en) * | 2008-07-15 | 2012-03-20 | Hoffmann-La Roche Inc. | Aminotetrahydroindazoloacetic acids |
| ES2378755T3 (es) * | 2008-07-15 | 2012-04-17 | F. Hoffmann-La Roche Ag | �?cidos aminotetrahidroindazoloacéticos |
| JP2012501975A (ja) * | 2008-09-08 | 2012-01-26 | メルク カナダ インコーポレイテッド | ステアロイルコエンザイムAδ−9デサチュラーゼの阻害剤としての芳香族複素環化合物 |
| JPWO2010074244A1 (ja) * | 2008-12-25 | 2012-06-21 | 大正製薬株式会社 | イソキノリン誘導体 |
| AU2010212970A1 (en) | 2009-02-12 | 2011-08-18 | Merck Serono S.A. | Phenoxy acetic acid derivatives |
| AR077413A1 (es) | 2009-07-16 | 2011-08-24 | Actelion Pharmaceuticals Ltd | Derivados piridin-4-ilo |
| WO2011079007A1 (en) * | 2009-12-23 | 2011-06-30 | Ironwood Pharmaceuticals, Inc. | Crth2 modulators |
| CN103119024A (zh) | 2010-06-23 | 2013-05-22 | 大正制药株式会社 | 异喹啉衍生物 |
| EP2590944B1 (en) | 2010-07-05 | 2015-09-30 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| ES2544086T3 (es) | 2011-01-19 | 2015-08-27 | Actelion Pharmaceuticals Ltd. | Derivados de 2-metoxi-piridin-4-ilo |
| WO2012154967A1 (en) * | 2011-05-12 | 2012-11-15 | Proteostasis Therapeutics, Inc. | Proteostasis regulators |
| CA2843383A1 (en) | 2011-07-29 | 2013-02-07 | Taisho Pharmaceutical Co., Ltd. | Amidine compound or salt thereof |
| WO2013088109A1 (en) | 2011-12-16 | 2013-06-20 | Oxagen Limited | Combination of crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
| ES2624379T3 (es) | 2011-12-21 | 2017-07-14 | Idorsia Pharmaceuticals Ltd | Derivados de heterociclilo y su uso como moduladores del receptor de prostaglandina D2 |
| US9169270B2 (en) | 2012-07-05 | 2015-10-27 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin D2 receptor modulators |
| TWI695831B (zh) | 2014-09-13 | 2020-06-11 | 香港商南北兄弟藥業投資有限公司 | Crth2拮抗劑化合物及其用途 |
| EP3197888A4 (en) | 2014-09-25 | 2018-03-14 | University of Notre Dame du Lac | Non-beta lactam antibiotics |
| US10385043B2 (en) | 2015-05-20 | 2019-08-20 | Idorsia Pharmaceuticals Ltd | Crystalline form of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol |
| US11168062B2 (en) | 2016-09-12 | 2021-11-09 | University Of Notre Dame Du Lac | Compounds for the treatment of Clostridium difficile infection |
| TWI805601B (zh) | 2017-08-11 | 2023-06-21 | 南韓商愛茉莉太平洋股份有限公司 | 醫藥組成物及抑制其形成結晶的方法 |
| US11247987B2 (en) | 2017-10-06 | 2022-02-15 | Forma Therapeutics, Inc. | Inhibiting ubiquitin specific peptidase 30 |
| KR20200143376A (ko) | 2018-03-13 | 2020-12-23 | 샤이어 휴먼 지네틱 테라피즈 인크. | 혈장 칼리크레인 억제제로서의 치환된 이미다조피리딘 및 이의 용도 |
| KR102518632B1 (ko) | 2018-04-18 | 2023-04-06 | (주)아모레퍼시픽 | (r)-n-[1-(3,5-다이플루오로-4-메테인설폰일아미노-페닐)-에틸]-3-(2-프로필-6-트라이플루오로메틸-피리딘-3-일)-아크릴아마이드를 함유하는 약학 조성물 |
| IL278291B2 (en) | 2018-05-17 | 2023-10-01 | Forma Therapeutics Inc | Fused bicyclic compounds useful as ubiquitin-specific peptidase 30 inhibitors |
| LT3860989T (lt) | 2018-10-05 | 2023-06-12 | Forma Therapeutics, Inc. | Sulieti pirolinai, kurie veikia kaip ubikvitinui specifinės proteazės 30 (ups30) inhibitoriai |
| US11787796B2 (en) | 2019-09-18 | 2023-10-17 | Takeda Pharmaceutical Company Limited | Plasma Kallikrein inhibitors and uses thereof |
| CN114667289B (zh) | 2019-09-18 | 2025-08-26 | 武田药品工业有限公司 | 杂芳基血浆激肽释放酶抑制剂 |
| JPWO2022138700A1 (enExample) * | 2020-12-23 | 2022-06-30 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2104932A1 (en) * | 1970-09-08 | 1972-04-28 | Ferlux | O-hydroxyphenyl pyrazoles - hypocholesterolemics anti inflammatories analgesics etc |
| CA2150483C (en) * | 1992-12-17 | 1999-09-14 | Pfizer Limited | Pyrazoles and pyrazolopyrimidines |
| AU9002798A (en) | 1997-09-19 | 1999-04-12 | Ono Pharmaceutical Co. Ltd. | Fused or nonfused benzene compounds |
| US6291514B1 (en) * | 1998-02-09 | 2001-09-18 | 3-Dimensional Pharmaceuticals, Inc. | Heteroaryl amidines, methylamidines and guanidines, preparation thereof, and use thereof as protease inhibitors |
| IL139169A0 (en) * | 1998-05-05 | 2001-11-25 | Hoffmann La Roche | Pyrazole derivatives as p-38 map kinase inhibitors |
| US6316466B1 (en) * | 1998-05-05 | 2001-11-13 | Syntex (U.S.A.) Llc | Pyrazole derivatives P-38 MAP kinase inhibitors |
| US6376527B1 (en) * | 1998-05-05 | 2002-04-23 | Syntex (U.S.A.) Llc | Pyrazole derivatives-p38 map kinase inhibitors |
| IL153565A0 (en) * | 2000-06-20 | 2003-07-06 | Atherogenics Inc | 1,3-bis-(substituted-phenyl)-2-propen-1-ones and their use to treat vcam-1 mediated disorders |
| DE60128475T2 (de) * | 2000-07-25 | 2008-02-07 | Merck & Co., Inc. | N-substituierte indole mit anwendung in der behandlung von diabetes |
| RU2312101C2 (ru) * | 2001-12-18 | 2007-12-10 | Ф.Хоффманн-Ля Рош Аг | Цис-имидазолины в качестве ингибиторов mdm2 |
| SE0200411D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| SE0200356D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| JPWO2003097042A1 (ja) | 2002-05-16 | 2005-09-15 | 塩野義製薬株式会社 | Pgd2受容体拮抗剤 |
| US7534897B2 (en) | 2002-05-16 | 2009-05-19 | Shionogi & Co., Ltd. | Indole arylsulfonaimide compounds exhibiting PGD 2 receptor antagonism |
| GB2388540A (en) | 2002-05-17 | 2003-11-19 | Bayer Ag | New use of Ramatroban |
| TW200307542A (en) | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
| SE0201635D0 (sv) | 2002-05-30 | 2002-05-30 | Astrazeneca Ab | Novel compounds |
| DK1537078T3 (da) * | 2002-08-29 | 2010-08-02 | Merck Sharp & Dohme | Indoler med anti-diabetisk aktivitet |
| SE0301010D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| SA04250253B1 (ar) * | 2003-08-21 | 2009-11-10 | استرازينيكا ايه بي | احماض فينوكسي اسيتيك مستبدلة باعتبارها مركبات صيدلانية لعلاج الامراض التنفسية مثل الربو ومرض الانسداد الرئوي المزمن |
| WO2007062678A1 (en) * | 2005-11-29 | 2007-06-07 | 7Tm Pharma A/S | Phenoxyacetic acid derivatives as crth2 receptor ligands |
-
2005
- 2005-05-30 EP EP10177122A patent/EP2336113A1/en not_active Withdrawn
- 2005-05-30 WO PCT/EP2005/005884 patent/WO2005115382A1/en not_active Ceased
- 2005-05-30 CA CA002568766A patent/CA2568766A1/en not_active Abandoned
- 2005-05-30 MX MXPA06013912A patent/MXPA06013912A/es not_active Application Discontinuation
- 2005-05-30 EP EP05770220A patent/EP1758579A1/en not_active Withdrawn
- 2005-05-30 KR KR1020067027504A patent/KR20070045153A/ko not_active Ceased
- 2005-05-30 US US11/597,873 patent/US8022063B2/en not_active Expired - Fee Related
- 2005-05-30 BR BRPI0511676-7A patent/BRPI0511676A/pt not_active IP Right Cessation
- 2005-05-30 AU AU2005247110A patent/AU2005247110B2/en not_active Ceased
- 2005-05-30 NZ NZ551810A patent/NZ551810A/en unknown
- 2005-05-30 EA EA200602290A patent/EA014729B1/ru not_active IP Right Cessation
- 2005-05-30 JP JP2007513846A patent/JP2008500991A/ja not_active Ceased
-
2006
- 2006-11-29 IL IL179694A patent/IL179694A/en not_active IP Right Cessation
- 2006-12-22 CR CR8838A patent/CR8838A/es not_active Application Discontinuation
- 2006-12-28 NO NO20066048A patent/NO20066048L/no not_active Application Discontinuation
-
2011
- 2011-06-02 US US13/151,317 patent/US20110269763A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US8022063B2 (en) | 2011-09-20 |
| EP2336113A1 (en) | 2011-06-22 |
| NO20066048L (no) | 2007-02-27 |
| CR8838A (es) | 2009-01-12 |
| HK1107763A1 (en) | 2008-04-18 |
| US20090099189A1 (en) | 2009-04-16 |
| AU2005247110B2 (en) | 2010-08-26 |
| JP2008500991A (ja) | 2008-01-17 |
| AU2005247110A1 (en) | 2005-12-08 |
| EA200602290A1 (ru) | 2007-06-29 |
| IL179694A0 (en) | 2008-03-20 |
| WO2005115382A1 (en) | 2005-12-08 |
| NZ551810A (en) | 2010-09-30 |
| EA014729B1 (ru) | 2011-02-28 |
| CA2568766A1 (en) | 2005-12-08 |
| US20110269763A1 (en) | 2011-11-03 |
| EP1758579A1 (en) | 2007-03-07 |
| BRPI0511676A (pt) | 2008-01-08 |
| KR20070045153A (ko) | 2007-05-02 |
| MXPA06013912A (es) | 2007-07-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IL179694A (en) | Use of crth2 receptor ligands for the preparation of a pharmaceutical composition, some such ligands and pharmaceutical composition comprising the ligand | |
| US9447058B2 (en) | Substituted 1,3-thiazoles as heat shock transcription factor 1 activators | |
| RU2382770C2 (ru) | Производные тетрагидрокарбазолов, способ их получения и фармацевтические композиции, содержащие их | |
| WO1999046232A1 (en) | Carboxylic acid derivatives and drugs containing the same as the active ingredient | |
| TW200539854A (en) | Compounds, pharmaceutical compositions and methods for use in treating metabolic disorders | |
| JP2001354671A (ja) | ペルオキシソーム増殖剤応答性受容体δの活性化剤 | |
| CN101466687A (zh) | 过氧化物酶体增殖剂激活受体δ的激活剂 | |
| US20080312220A1 (en) | Oxadiazole Derivatives with Crth2 Receptor Activity | |
| WO2005116001A1 (en) | Substituted thiazoleacetic as crth2 ligands | |
| CN1980664B (zh) | 用于医学用途的crth2受体配体 | |
| TWI320710B (en) | Acylaminothiazole derivatives, their preparation and their therapeutic use | |
| JP2013538808A (ja) | Dgat1阻害剤としての複素環式化合物 | |
| HK1107763B (en) | Crth2 receptor ligands for medicinal uses | |
| JPWO2007004733A1 (ja) | ペルオキシソーム増殖剤活性化受容体δの活性化剤 | |
| HK1107811A (en) | Substituted thiazoleacetic as crth2 ligands | |
| JP2005206515A (ja) | 5員環化合物 | |
| JPWO2001014352A1 (ja) | 置換ベンジルチアゾリジン−2,4−ジオン誘導体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| MM9K | Patent not in force due to non-payment of renewal fees |