CA2568742A1 - Substituted thiazoleacetic as crth2 ligands - Google Patents
Substituted thiazoleacetic as crth2 ligands Download PDFInfo
- Publication number
- CA2568742A1 CA2568742A1 CA002568742A CA2568742A CA2568742A1 CA 2568742 A1 CA2568742 A1 CA 2568742A1 CA 002568742 A CA002568742 A CA 002568742A CA 2568742 A CA2568742 A CA 2568742A CA 2568742 A1 CA2568742 A1 CA 2568742A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- compound
- hydrogen
- alkyl
- ring
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003446 ligand Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 71
- 239000001257 hydrogen Substances 0.000 claims abstract description 71
- -1 N-piperidinyl Chemical group 0.000 claims abstract description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 125000001424 substituent group Chemical group 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
- 201000010099 disease Diseases 0.000 claims abstract description 23
- 102000009389 Prostaglandin D receptors Human genes 0.000 claims abstract description 22
- 108050000258 Prostaglandin D receptors Proteins 0.000 claims abstract description 22
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 208000006673 asthma Diseases 0.000 claims abstract description 9
- 230000000694 effects Effects 0.000 claims abstract description 9
- 206010039083 rhinitis Diseases 0.000 claims abstract description 9
- 208000028004 allergic respiratory disease Diseases 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 230000000172 allergic effect Effects 0.000 claims abstract description 6
- 208000010668 atopic eczema Diseases 0.000 claims abstract description 6
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 4
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims abstract description 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 37
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 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 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000001246 bromo group Chemical group Br* 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000006413 ring segment Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- 208000002197 Ehlers-Danlos syndrome Diseases 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 201000001981 dermatomyositis Diseases 0.000 claims description 4
- 201000002491 encephalomyelitis Diseases 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 208000002574 reactive arthritis Diseases 0.000 claims description 4
- 201000000306 sarcoidosis Diseases 0.000 claims description 4
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 4
- VIVMXCOHKFWMFI-UHFFFAOYSA-N 2-[2-[1-(4-chlorophenyl)-2-phenylethyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(CC=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=NC=1C1=CC=C(F)C=C1 VIVMXCOHKFWMFI-UHFFFAOYSA-N 0.000 claims description 3
- PMKHRUSPKPZZRI-UHFFFAOYSA-N 2-[2-[bis(4-fluorophenyl)methyl]-4-(3,4-difluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=NC=1C1=CC=C(F)C(F)=C1 PMKHRUSPKPZZRI-UHFFFAOYSA-N 0.000 claims description 3
- VRLVQIAKWWEZRU-UHFFFAOYSA-N 2-[2-[bis(4-fluorophenyl)methyl]-4-(3-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=NC=1C1=CC=CC(F)=C1 VRLVQIAKWWEZRU-UHFFFAOYSA-N 0.000 claims description 3
- QNEMKHXNYQDLAU-UHFFFAOYSA-N 2-[2-[bis(4-fluorophenyl)methyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=NC=1C1=CC=C(F)C=C1 QNEMKHXNYQDLAU-UHFFFAOYSA-N 0.000 claims description 3
- ZOTGQGLOXKIJDG-UHFFFAOYSA-N 2-[2-[bis(4-methoxyphenyl)methyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(OC)=CC=1)C1=NC(C=2C=CC(F)=CC=2)=C(CC(O)=O)S1 ZOTGQGLOXKIJDG-UHFFFAOYSA-N 0.000 claims description 3
- VZONOYMJTLNJGC-UHFFFAOYSA-N 2-[2-benzhydryl-4-(3,4-difluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C1=CC=C(F)C(F)=C1 VZONOYMJTLNJGC-UHFFFAOYSA-N 0.000 claims description 3
- PVJXZPBQSMAWDT-UHFFFAOYSA-N 2-[2-benzhydryl-4-(3-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C1=CC=CC(F)=C1 PVJXZPBQSMAWDT-UHFFFAOYSA-N 0.000 claims description 3
- HIEUVNLETVQMHD-UHFFFAOYSA-N 2-[2-benzhydryl-4-(4-chlorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 HIEUVNLETVQMHD-UHFFFAOYSA-N 0.000 claims description 3
- RQZPTTAHWVRWET-UHFFFAOYSA-N 2-[2-benzhydryl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C1=CC=C(F)C=C1 RQZPTTAHWVRWET-UHFFFAOYSA-N 0.000 claims description 3
- RSXKKNQRSFGEQT-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[(4-chlorophenyl)-phenylmethyl]-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=NC=1C1=CC=C(Cl)C=C1 RSXKKNQRSFGEQT-UHFFFAOYSA-N 0.000 claims description 3
- VOTMNFLWKCFMIN-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[(4-methoxyphenyl)-phenylmethyl]-1,3-thiazol-5-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC=CC=1)C1=NC(C=2C=CC(Cl)=CC=2)=C(CC(O)=O)S1 VOTMNFLWKCFMIN-UHFFFAOYSA-N 0.000 claims description 3
- FONANTIGBWSYGE-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-2-[(4-methoxyphenyl)-phenylmethyl]-1,3-thiazol-5-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC=CC=1)C1=NC(C=2C=CC(F)=CC=2)=C(CC(O)=O)S1 FONANTIGBWSYGE-UHFFFAOYSA-N 0.000 claims description 3
- 206010020751 Hypersensitivity Diseases 0.000 claims description 3
- 230000007815 allergy Effects 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- XCFLGUSGJLLMBZ-UHFFFAOYSA-N 2-[2-[(3,4-difluorophenyl)-phenylmethyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=C(F)C(F)=CC=2)=NC=1C1=CC=C(F)C=C1 XCFLGUSGJLLMBZ-UHFFFAOYSA-N 0.000 claims description 2
- RAJBDMPVCAZUIO-UHFFFAOYSA-N 2-[2-[(4-chlorophenyl)-phenylmethyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=NC=1C1=CC=C(F)C=C1 RAJBDMPVCAZUIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 206010065040 AIDS dementia complex Diseases 0.000 claims description 2
- 208000009304 Acute Kidney Injury Diseases 0.000 claims description 2
- 208000035939 Alveolitis allergic Diseases 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
- 206010003267 Arthritis reactive Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- KLYCPFXDDDMZNQ-UHFFFAOYSA-N Benzyne Chemical compound C1=CC#CC=C1 KLYCPFXDDDMZNQ-UHFFFAOYSA-N 0.000 claims description 2
- 206010006811 Bursitis Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- 206010010741 Conjunctivitis Diseases 0.000 claims description 2
- 206010011224 Cough Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 2
- 206010014950 Eosinophilia Diseases 0.000 claims description 2
- 208000027445 Farmer Lung Diseases 0.000 claims description 2
- 206010016228 Fasciitis Diseases 0.000 claims description 2
- 208000001640 Fibromyalgia Diseases 0.000 claims description 2
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 2
- 201000005569 Gout Diseases 0.000 claims description 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 2
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims description 2
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 208000009388 Job Syndrome Diseases 0.000 claims description 2
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims description 2
- 208000009829 Lewy Body Disease Diseases 0.000 claims description 2
- 201000002832 Lewy body dementia Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims description 2
- 201000002481 Myositis Diseases 0.000 claims description 2
- 206010065673 Nephritic syndrome Diseases 0.000 claims description 2
- 206010031264 Osteonecrosis Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 206010056332 Panencephalitis Diseases 0.000 claims description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
- 208000033464 Reiter syndrome Diseases 0.000 claims description 2
- 208000033626 Renal failure acute Diseases 0.000 claims description 2
- 206010063837 Reperfusion injury Diseases 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 206010040047 Sepsis Diseases 0.000 claims description 2
- 206010040070 Septic Shock Diseases 0.000 claims description 2
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 2
- 208000016247 Soft tissue disease Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 208000000491 Tendinopathy Diseases 0.000 claims description 2
- 206010043255 Tendonitis Diseases 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 201000004810 Vascular dementia Diseases 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 201000011040 acute kidney failure Diseases 0.000 claims description 2
- 208000012998 acute renal failure Diseases 0.000 claims description 2
- 208000026935 allergic disease Diseases 0.000 claims description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 201000008937 atopic dermatitis Diseases 0.000 claims description 2
- 206010006451 bronchitis Diseases 0.000 claims description 2
- 208000003295 carpal tunnel syndrome Diseases 0.000 claims description 2
- 208000025434 cerebellar degeneration Diseases 0.000 claims description 2
- 208000013116 chronic cough Diseases 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 208000020832 chronic kidney disease Diseases 0.000 claims description 2
- 208000022831 chronic renal failure syndrome Diseases 0.000 claims description 2
- 230000003210 demyelinating effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000022195 farmer lung disease Diseases 0.000 claims description 2
- 208000024908 graft versus host disease Diseases 0.000 claims description 2
- 206010051040 hyper-IgE syndrome Diseases 0.000 claims description 2
- 208000014674 injury Diseases 0.000 claims description 2
- 230000000302 ischemic effect Effects 0.000 claims description 2
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims description 2
- 201000010260 leiomyoma Diseases 0.000 claims description 2
- 210000004072 lung Anatomy 0.000 claims description 2
- 206010025135 lupus erythematosus Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002207 metabolite Substances 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 206010065579 multifocal motor neuropathy Diseases 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 208000020469 nerve plexus disease Diseases 0.000 claims description 2
- 201000006380 plexopathy Diseases 0.000 claims description 2
- 208000015768 polyposis Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 230000036303 septic shock Effects 0.000 claims description 2
- 201000004415 tendinitis Diseases 0.000 claims description 2
- 238000002054 transplantation Methods 0.000 claims description 2
- 230000008733 trauma Effects 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 17
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 9
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 3
- 208000027496 Behcet disease Diseases 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 76
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 54
- 125000000217 alkyl group Chemical group 0.000 description 36
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 238000009739 binding Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 230000027455 binding Effects 0.000 description 12
- IGOYRYSKKLREIH-UHFFFAOYSA-N 3-bromo-4-(4-chlorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CC(Br)C(=O)C1=CC=C(Cl)C=C1 IGOYRYSKKLREIH-UHFFFAOYSA-N 0.000 description 10
- 125000005647 linker group Chemical group 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- UKHILQXQALHBSK-UHFFFAOYSA-N 2-[2-[(2-bromophenyl)methyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound N=1C(C=2C=CC(F)=CC=2)=C(CC(=O)O)SC=1CC1=CC=CC=C1Br UKHILQXQALHBSK-UHFFFAOYSA-N 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000003556 assay Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- 238000000225 bioluminescence resonance energy transfer Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- CAZGDYWJCWEYTI-UHFFFAOYSA-N 3-bromo-4-(4-fluorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CC(Br)C(=O)C1=CC=C(F)C=C1 CAZGDYWJCWEYTI-UHFFFAOYSA-N 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- 229960004132 diethyl ether Drugs 0.000 description 4
- 210000003979 eosinophil Anatomy 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 125000000842 isoxazolyl group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 229940014800 succinic anhydride Drugs 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- CLCMSGXEVLGRNG-UHFFFAOYSA-N 2,2-diphenylethanimidamide Chemical compound C=1C=CC=CC=1C(C(=N)N)C1=CC=CC=C1 CLCMSGXEVLGRNG-UHFFFAOYSA-N 0.000 description 2
- NVMUWWIKRDQQQC-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-phenylpropanenitrile Chemical compound C1=CC(Cl)=CC=C1C(C#N)CC1=CC=CC=C1 NVMUWWIKRDQQQC-UHFFFAOYSA-N 0.000 description 2
- YWKJIFLIAFUORU-UHFFFAOYSA-N 2-(4-methoxyphenyl)-2-pyridin-2-ylethanethioamide Chemical compound C1=CC(OC)=CC=C1C(C(N)=S)C1=CC=CC=N1 YWKJIFLIAFUORU-UHFFFAOYSA-N 0.000 description 2
- QPBMRNIWGGHZFG-UHFFFAOYSA-N 2-[2-[(1-acetylpiperidin-4-yl)-phenylmethyl]-4-(4-chlorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound C1CN(C(=O)C)CCC1C(C=1C=CC=CC=1)C1=NC(C=2C=CC(Cl)=CC=2)=C(CC(O)=O)S1 QPBMRNIWGGHZFG-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
- WUYWHIAAQYQKPP-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(F)C=C1 WUYWHIAAQYQKPP-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 108091026890 Coding region Proteins 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 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
- 239000007995 HEPES buffer Substances 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
- 241001421711 Mithras Species 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
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 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
- 125000003342 alkenyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 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
- 229940125388 beta agonist Drugs 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000002299 complementary DNA Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000013604 expression vector Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000012634 fragment Substances 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
- 210000002443 helper t lymphocyte Anatomy 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 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
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- VWCMKZNONFEVOC-UHFFFAOYSA-N methyl 3-bromo-4-(4-fluorophenyl)-4-oxobutanoate Chemical compound COC(=O)CC(Br)C(=O)C1=CC=C(F)C=C1 VWCMKZNONFEVOC-UHFFFAOYSA-N 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
- 239000002687 nonaqueous vehicle Substances 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000000159 protein binding assay Methods 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 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
- 150000003557 thiazoles Chemical class 0.000 description 2
- 125000000335 thiazolyl 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- ROEQGIFOWRQYHD-UHFFFAOYSA-N (2-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC=C1B(O)O ROEQGIFOWRQYHD-UHFFFAOYSA-N 0.000 description 1
- IBTSWKLSEOGJGJ-UHFFFAOYSA-N (3-acetamidophenyl)boronic acid Chemical compound CC(=O)NC1=CC=CC(B(O)O)=C1 IBTSWKLSEOGJGJ-UHFFFAOYSA-N 0.000 description 1
- XDBHWPLGGBLUHH-UHFFFAOYSA-N (3-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C#N)=C1 XDBHWPLGGBLUHH-UHFFFAOYSA-N 0.000 description 1
- NLLGFYPSWCMUIV-UHFFFAOYSA-N (3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1 NLLGFYPSWCMUIV-UHFFFAOYSA-N 0.000 description 1
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 1
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-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
- 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
- KQNBRMUBPRGXSL-UHFFFAOYSA-N 1-(bromomethyl)-4-chlorobenzene Chemical compound ClC1=CC=C(CBr)C=C1 KQNBRMUBPRGXSL-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
- QSJFDBITYUEIBY-UHFFFAOYSA-N 1-acetyl-4-phenylpiperidine-4-carbothioamide;2-(1-acetylpiperidin-4-yl)-2-phenylethanethioamide Chemical compound C1CN(C(=O)C)CCC1(C(N)=S)C1=CC=CC=C1.C1CN(C(=O)C)CCC1C(C(N)=S)C1=CC=CC=C1 QSJFDBITYUEIBY-UHFFFAOYSA-N 0.000 description 1
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical compound BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-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
- 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
- LBHVAPBTHOCEEZ-UHFFFAOYSA-N 1-phenylcyclopropane-1-carbothioamide Chemical compound C=1C=CC=CC=1C1(C(=S)N)CC1 LBHVAPBTHOCEEZ-UHFFFAOYSA-N 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- JPKIYKWSYBYKIS-UHFFFAOYSA-N 2,2-bis(4-fluorophenyl)acetonitrile Chemical compound C1=CC(F)=CC=C1C(C#N)C1=CC=C(F)C=C1 JPKIYKWSYBYKIS-UHFFFAOYSA-N 0.000 description 1
- UIXOENLJOZWZRS-UHFFFAOYSA-N 2,2-bis(4-fluorophenyl)ethanethioamide Chemical compound C=1C=C(F)C=CC=1C(C(=S)N)C1=CC=C(F)C=C1 UIXOENLJOZWZRS-UHFFFAOYSA-N 0.000 description 1
- UYVKMNROFWNHHB-UHFFFAOYSA-N 2,2-bis(4-methoxyphenyl)acetonitrile Chemical compound C1=CC(OC)=CC=C1C(C#N)C1=CC=C(OC)C=C1 UYVKMNROFWNHHB-UHFFFAOYSA-N 0.000 description 1
- OHXOZNXAGAXELL-UHFFFAOYSA-N 2,2-bis(4-methoxyphenyl)ethanethioamide Chemical compound C1=CC(OC)=CC=C1C(C(N)=S)C1=CC=C(OC)C=C1 OHXOZNXAGAXELL-UHFFFAOYSA-N 0.000 description 1
- NEBPTMCRLHKPOB-UHFFFAOYSA-N 2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)C1=CC=CC=C1 NEBPTMCRLHKPOB-UHFFFAOYSA-N 0.000 description 1
- QMAWTTMRRXVHNI-UHFFFAOYSA-N 2,2-diphenylethanethioamide Chemical compound C=1C=CC=CC=1C(C(=S)N)C1=CC=CC=C1 QMAWTTMRRXVHNI-UHFFFAOYSA-N 0.000 description 1
- DRONDEZXOJEUGU-UHFFFAOYSA-N 2,3-diphenylpropanenitrile Chemical compound C=1C=CC=CC=1C(C#N)CC1=CC=CC=C1 DRONDEZXOJEUGU-UHFFFAOYSA-N 0.000 description 1
- GSFLUFCQJVKCFD-UHFFFAOYSA-N 2-(2-benzhydryl-4-phenyl-1,3-thiazol-5-yl)acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 GSFLUFCQJVKCFD-UHFFFAOYSA-N 0.000 description 1
- RITRBTUNNIPGOB-UHFFFAOYSA-N 2-(2-bromophenyl)ethanethioamide Chemical compound NC(=S)CC1=CC=CC=C1Br RITRBTUNNIPGOB-UHFFFAOYSA-N 0.000 description 1
- ADDCMRQCFSRMLB-UHFFFAOYSA-N 2-(2-phenoxyphenyl)ethanethioamide Chemical compound NC(=S)CC1=CC=CC=C1OC1=CC=CC=C1 ADDCMRQCFSRMLB-UHFFFAOYSA-N 0.000 description 1
- GUMQORYYHBWPGV-UHFFFAOYSA-N 2-(2-phenylphenyl)ethanethioamide Chemical compound NC(=S)CC1=CC=CC=C1C1=CC=CC=C1 GUMQORYYHBWPGV-UHFFFAOYSA-N 0.000 description 1
- SXWGHBHXXRZQEE-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-2-phenylacetonitrile Chemical compound C1=C(F)C(F)=CC=C1C(C#N)C1=CC=CC=C1 SXWGHBHXXRZQEE-UHFFFAOYSA-N 0.000 description 1
- NKWUBAHXXVBRHF-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-2-phenylethanethioamide Chemical compound C=1C=C(F)C(F)=CC=1C(C(=S)N)C1=CC=CC=C1 NKWUBAHXXVBRHF-UHFFFAOYSA-N 0.000 description 1
- WNIDSLWDGXYSST-UHFFFAOYSA-N 2-(3-chloropyridin-2-yl)-2-phenylethanethioamide Chemical compound N=1C=CC=C(Cl)C=1C(C(=S)N)C1=CC=CC=C1 WNIDSLWDGXYSST-UHFFFAOYSA-N 0.000 description 1
- OZTNTRFNRLHMKC-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-phenylacetonitrile Chemical compound C1=CC(Cl)=CC=C1C(C#N)C1=CC=CC=C1 OZTNTRFNRLHMKC-UHFFFAOYSA-N 0.000 description 1
- SKHXXKUGXMCJLZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-phenylethanethioamide Chemical compound C=1C=C(Cl)C=CC=1C(C(=S)N)C1=CC=CC=C1 SKHXXKUGXMCJLZ-UHFFFAOYSA-N 0.000 description 1
- PCHAVTZQQXNQPD-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-phenylpropanethioamide Chemical compound C=1C=C(Cl)C=CC=1C(C(=S)N)CC1=CC=CC=C1 PCHAVTZQQXNQPD-UHFFFAOYSA-N 0.000 description 1
- LRNPWSOSXVCRKG-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-phenylacetonitrile Chemical compound C1=CC(F)=CC=C1C(C#N)C1=CC=CC=C1 LRNPWSOSXVCRKG-UHFFFAOYSA-N 0.000 description 1
- YTKRSEAHNOYLEH-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-phenylethanethioamide Chemical compound C=1C=C(F)C=CC=1C(C(=S)N)C1=CC=CC=C1 YTKRSEAHNOYLEH-UHFFFAOYSA-N 0.000 description 1
- NMRODAMTCYVZAZ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-2-phenylacetonitrile Chemical compound C1=CC(OC)=CC=C1C(C#N)C1=CC=CC=C1 NMRODAMTCYVZAZ-UHFFFAOYSA-N 0.000 description 1
- CPMHOPCQCHUXAU-UHFFFAOYSA-N 2-(4-methoxyphenyl)-2-phenylethanethioamide Chemical compound C1=CC(OC)=CC=C1C(C(N)=S)C1=CC=CC=C1 CPMHOPCQCHUXAU-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
- WFMWMVKHLDVBAD-UHFFFAOYSA-N 2-[2-[(2-bromophenyl)methyl]-1,3-thiazol-5-yl]acetic acid Chemical compound S1C(CC(=O)O)=CN=C1CC1=CC=CC=C1Br WFMWMVKHLDVBAD-UHFFFAOYSA-N 0.000 description 1
- XWMQEKVCOFQUDX-UHFFFAOYSA-N 2-[2-[(cyclobutanecarbonylamino)-phenylmethyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(NC(=O)C2CCC2)C=2C=CC=CC=2)=NC=1C1=CC=C(F)C=C1 XWMQEKVCOFQUDX-UHFFFAOYSA-N 0.000 description 1
- ZKCOZROXSAQFQY-UHFFFAOYSA-N 2-[2-[[2-(1,3-benzodioxol-5-yl)phenyl]methyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(CC=2C(=CC=CC=2)C=2C=C3OCOC3=CC=2)=NC=1C1=CC=C(F)C=C1 ZKCOZROXSAQFQY-UHFFFAOYSA-N 0.000 description 1
- UCKNRBAHVSABBD-UHFFFAOYSA-N 2-[2-[[2-(3-acetamidophenyl)phenyl]methyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound CC(=O)NC1=CC=CC(C=2C(=CC=CC=2)CC=2SC(CC(O)=O)=C(N=2)C=2C=CC(F)=CC=2)=C1 UCKNRBAHVSABBD-UHFFFAOYSA-N 0.000 description 1
- SYRMYDRBDXUBHO-UHFFFAOYSA-N 2-[2-[[2-(3-cyanophenyl)phenyl]methyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound N=1C(C=2C=CC(F)=CC=2)=C(CC(=O)O)SC=1CC1=CC=CC=C1C1=CC=CC(C#N)=C1 SYRMYDRBDXUBHO-UHFFFAOYSA-N 0.000 description 1
- WCTIFYXNSJWYEP-UHFFFAOYSA-N 2-[2-[[2-(4-cyanophenyl)phenyl]methyl]-4-(4-fluorophenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound N=1C(C=2C=CC(F)=CC=2)=C(CC(=O)O)SC=1CC1=CC=CC=C1C1=CC=C(C#N)C=C1 WCTIFYXNSJWYEP-UHFFFAOYSA-N 0.000 description 1
- WDKJUWYFSCMORY-UHFFFAOYSA-N 2-[2-benzhydryl-4-(2,5-dimethoxyphenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound COC1=CC=C(OC)C(C2=C(SC(=N2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC(O)=O)=C1 WDKJUWYFSCMORY-UHFFFAOYSA-N 0.000 description 1
- GPPYWAGMOJZIGF-UHFFFAOYSA-N 2-[2-benzhydryl-4-(4-methoxyphenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=C(CC(O)=O)SC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 GPPYWAGMOJZIGF-UHFFFAOYSA-N 0.000 description 1
- AIXRYCLEZGOJML-UHFFFAOYSA-N 2-[2-benzhydryl-4-(5-chloro-2-methoxyphenyl)-1,3-thiazol-5-yl]acetic acid Chemical compound COC1=CC=C(Cl)C=C1C1=C(CC(O)=O)SC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 AIXRYCLEZGOJML-UHFFFAOYSA-N 0.000 description 1
- KWLSRKASVDOURW-UHFFFAOYSA-N 2-[2-benzhydryl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C1=CC=C(C(F)(F)F)C=C1 KWLSRKASVDOURW-UHFFFAOYSA-N 0.000 description 1
- SGEBFVPESSRQLS-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-(1,2-diphenylethyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(CC=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 SGEBFVPESSRQLS-UHFFFAOYSA-N 0.000 description 1
- FZLCAVSJFICPJL-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-(1-phenylcyclopropyl)-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C2(CC2)C=2C=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 FZLCAVSJFICPJL-UHFFFAOYSA-N 0.000 description 1
- HDVJQXALBFFODC-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-(1-phenylpropyl)-1,3-thiazol-5-yl]acetic acid Chemical compound C=1C=CC=CC=1C(CC)C(SC=1CC(O)=O)=NC=1C1=CC=C(Cl)C=C1 HDVJQXALBFFODC-UHFFFAOYSA-N 0.000 description 1
- XABTYDRBGWHHBM-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[(2-phenoxyphenyl)methyl]-1,3-thiazol-5-yl]acetic acid Chemical compound N=1C(C=2C=CC(Cl)=CC=2)=C(CC(=O)O)SC=1CC1=CC=CC=C1OC1=CC=CC=C1 XABTYDRBGWHHBM-UHFFFAOYSA-N 0.000 description 1
- XSEQEOCIQGGXMC-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[(2-phenylphenyl)methyl]-1,3-thiazol-5-yl]acetic acid Chemical compound N=1C(C=2C=CC(Cl)=CC=2)=C(CC(=O)O)SC=1CC1=CC=CC=C1C1=CC=CC=C1 XSEQEOCIQGGXMC-UHFFFAOYSA-N 0.000 description 1
- MUEYAAPTFVPHMH-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[(3,4-difluorophenyl)-phenylmethyl]-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=C(F)C(F)=CC=2)=NC=1C1=CC=C(Cl)C=C1 MUEYAAPTFVPHMH-UHFFFAOYSA-N 0.000 description 1
- YMPRFAGNYQRMNU-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[(3-chloropyridin-2-yl)-phenylmethyl]-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C(=CC=CN=2)Cl)=NC=1C1=CC=C(Cl)C=C1 YMPRFAGNYQRMNU-UHFFFAOYSA-N 0.000 description 1
- KFYBMRFCSOFQBV-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[(4-fluorophenyl)-phenylmethyl]-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC(F)=CC=2)=NC=1C1=CC=C(Cl)C=C1 KFYBMRFCSOFQBV-UHFFFAOYSA-N 0.000 description 1
- VQLQSPXLCMPBHR-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[(4-methoxyphenyl)-pyridin-2-ylmethyl]-1,3-thiazol-5-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(C=1N=CC=CC=1)C1=NC(C=2C=CC(Cl)=CC=2)=C(CC(O)=O)S1 VQLQSPXLCMPBHR-UHFFFAOYSA-N 0.000 description 1
- MXGOWUYGDYVRFT-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[cyclohexyl(phenyl)methyl]-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C2CCCCC2)C=2C=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 MXGOWUYGDYVRFT-UHFFFAOYSA-N 0.000 description 1
- FTDOLMWQXVZKCL-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[phenyl(pyridin-2-yl)methyl]-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2N=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 FTDOLMWQXVZKCL-UHFFFAOYSA-N 0.000 description 1
- JIEKMACRVQTPRC-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-phenyl-5-thiazolyl]acetic acid Chemical compound OC(=O)CC=1SC(C=2C=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 JIEKMACRVQTPRC-UHFFFAOYSA-N 0.000 description 1
- IIMVGFRDUDAYTR-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-2-[(4-hydroxyphenyl)-phenylmethyl]-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(C=2C=CC=CC=2)C=2C=CC(O)=CC=2)=NC=1C1=CC=C(F)C=C1 IIMVGFRDUDAYTR-UHFFFAOYSA-N 0.000 description 1
- WTUDTMJLHNSLRR-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-2-[(4-methoxyphenyl)-pyridin-2-ylmethyl]-1,3-thiazol-5-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(C=1N=CC=CC=1)C1=NC(C=2C=CC(F)=CC=2)=C(CC(O)=O)S1 WTUDTMJLHNSLRR-UHFFFAOYSA-N 0.000 description 1
- WVRKJDUKGPVBQD-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-2-[[2-(2-methoxyphenyl)phenyl]methyl]-1,3-thiazol-5-yl]acetic acid Chemical compound COC1=CC=CC=C1C1=CC=CC=C1CC1=NC(C=2C=CC(F)=CC=2)=C(CC(O)=O)S1 WVRKJDUKGPVBQD-UHFFFAOYSA-N 0.000 description 1
- INCUMSMAXDFYHJ-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-2-[[2-(4-methoxyphenyl)phenyl]methyl]-1,3-thiazol-5-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=CC=C1CC1=NC(C=2C=CC(F)=CC=2)=C(CC(O)=O)S1 INCUMSMAXDFYHJ-UHFFFAOYSA-N 0.000 description 1
- GLTDPYBJGLZZJF-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-2-[[2-[3-(trifluoromethoxy)phenyl]phenyl]methyl]-1,3-thiazol-5-yl]acetic acid Chemical compound N=1C(C=2C=CC(F)=CC=2)=C(CC(=O)O)SC=1CC1=CC=CC=C1C1=CC=CC(OC(F)(F)F)=C1 GLTDPYBJGLZZJF-UHFFFAOYSA-N 0.000 description 1
- UJIJQEZEVZTMNA-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-2-[phenyl-[[4-(trifluoromethyl)benzoyl]amino]methyl]-1,3-thiazol-5-yl]acetic acid Chemical compound OC(=O)CC=1SC(C(NC(=O)C=2C=CC(=CC=2)C(F)(F)F)C=2C=CC=CC=2)=NC=1C1=CC=C(F)C=C1 UJIJQEZEVZTMNA-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
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- FERWLVHFCWBVTA-UHFFFAOYSA-N 2-cyclobutyl-2-phenylethanethioamide Chemical compound C=1C=CC=CC=1C(C(=S)N)C1CCC1 FERWLVHFCWBVTA-UHFFFAOYSA-N 0.000 description 1
- SRVNJKXVPCWWOF-UHFFFAOYSA-N 2-cyclohexyl-2-phenylethanethioamide Chemical compound C=1C=CC=CC=1C(C(=S)N)C1CCCCC1 SRVNJKXVPCWWOF-UHFFFAOYSA-N 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- FOQYDURHXZVLFT-UHFFFAOYSA-N 2-phenyl-2-pyridin-2-ylethanethioamide Chemical compound C=1C=CC=NC=1C(C(=S)N)C1=CC=CC=C1 FOQYDURHXZVLFT-UHFFFAOYSA-N 0.000 description 1
- PJFJNIMKKAXGHG-UHFFFAOYSA-N 2-phenylbutanethioamide Chemical compound CCC(C(N)=S)C1=CC=CC=C1 PJFJNIMKKAXGHG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ABVFADOVAQKBBK-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-phenylpropanenitrile Chemical compound C1=CC(Cl)=CC=C1CC(C#N)C1=CC=CC=C1 ABVFADOVAQKBBK-UHFFFAOYSA-N 0.000 description 1
- WGBJLSAZTNIJDN-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-phenylpropanethioamide Chemical compound C=1C=CC=CC=1C(C(=S)N)CC1=CC=C(Cl)C=C1 WGBJLSAZTNIJDN-UHFFFAOYSA-N 0.000 description 1
- PUVJWIKKYDJWTP-UHFFFAOYSA-N 3-bromo-4-(3,4-difluorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CC(Br)C(=O)C1=CC=C(F)C(F)=C1 PUVJWIKKYDJWTP-UHFFFAOYSA-N 0.000 description 1
- QZGACLGBLNYAOK-UHFFFAOYSA-N 3-bromo-4-(3-fluorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CC(Br)C(=O)C1=CC=CC(F)=C1 QZGACLGBLNYAOK-UHFFFAOYSA-N 0.000 description 1
- VWFCNOXLOVFXKZ-UHFFFAOYSA-N 3-bromo-4-(4-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(C(=O)C(Br)CC(O)=O)C=C1 VWFCNOXLOVFXKZ-UHFFFAOYSA-N 0.000 description 1
- RWANHKFXQLOHLO-UHFFFAOYSA-N 3-bromo-4-oxo-4-[4-(trifluoromethyl)phenyl]butanoic acid Chemical compound OC(=O)CC(Br)C(=O)C1=CC=C(C(F)(F)F)C=C1 RWANHKFXQLOHLO-UHFFFAOYSA-N 0.000 description 1
- VPUHMOLSUUYGEJ-UHFFFAOYSA-N 3-bromo-4-oxo-4-phenylbutanoic acid Chemical compound OC(=O)CC(Br)C(=O)C1=CC=CC=C1 VPUHMOLSUUYGEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- HSFBDVDTGCGJBZ-UHFFFAOYSA-N 4-(2,5-dimethoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(OC)C(C(=O)CCC(O)=O)=C1 HSFBDVDTGCGJBZ-UHFFFAOYSA-N 0.000 description 1
- HHVYNFFVNGZSNG-UHFFFAOYSA-N 4-(3-fluorophenyl)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=CC(F)=C1 HHVYNFFVNGZSNG-UHFFFAOYSA-N 0.000 description 1
- UKOWUQIVWVDBGE-UHFFFAOYSA-N 4-(5-chloro-2-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)CCC(O)=O UKOWUQIVWVDBGE-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
- MXDIUFKCBZTRIM-UHFFFAOYSA-N 4-oxo-4-(4-phenoxyphenyl)butanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OC1=CC=CC=C1 MXDIUFKCBZTRIM-UHFFFAOYSA-N 0.000 description 1
- XBTRBFQQDDYMFC-UHFFFAOYSA-N 4-oxo-4-[4-(trifluoromethyl)phenyl]butanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(C(F)(F)F)C=C1 XBTRBFQQDDYMFC-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
- 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
- 241000416162 Astragalus gummifer Species 0.000 description 1
- QVEVANFPNXEOLO-UHFFFAOYSA-N B(O)O.C1C=2C(C(C=CC21)=O)=O Chemical compound B(O)O.C1C=2C(C(C=CC21)=O)=O QVEVANFPNXEOLO-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 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 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 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
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-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
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 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
- 102100037346 Substance-P receptor Human genes 0.000 description 1
- 102000003141 Tachykinin Human genes 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- UWDFWVLAHRQSKK-UHFFFAOYSA-N [3-(trifluoromethoxy)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(OC(F)(F)F)=C1 UWDFWVLAHRQSKK-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 125000000304 alkynyl group Chemical group 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
- 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
- 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
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 239000012131 assay buffer Substances 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
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 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
- 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
- WCTZPQWLFWZYJE-UHFFFAOYSA-N bis(4-fluorophenyl)methanol Chemical compound C=1C=C(F)C=CC=1C(O)C1=CC=C(F)C=C1 WCTZPQWLFWZYJE-UHFFFAOYSA-N 0.000 description 1
- ZODAOVNETBTTJX-UHFFFAOYSA-N bis(4-methoxyphenyl)methanol Chemical compound C1=CC(OC)=CC=C1C(O)C1=CC=C(OC)C=C1 ZODAOVNETBTTJX-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 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
- 125000002837 carbocyclic group 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
- 210000003169 central nervous system Anatomy 0.000 description 1
- 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 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002975 chemoattractant Substances 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
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 238000000975 co-precipitation Methods 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
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling 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
- 238000005859 coupling reaction 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
- 239000012043 crude product 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
- 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
- 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
- 235000019441 ethanol Nutrition 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 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
- 229960002679 fentiazac Drugs 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
- 239000000834 fixative Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- GYDFFFKCUNUZEL-UHFFFAOYSA-N fluorobenzoylpropionic acid Chemical compound OC(=O)CCC(=O)C1=CC=C(F)C(F)=C1 GYDFFFKCUNUZEL-UHFFFAOYSA-N 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
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 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
- 150000002460 imidazoles Chemical class 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
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 1
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-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
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 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
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium 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
- DTKMKZYEOXZPQZ-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=C[C-]=C1 DTKMKZYEOXZPQZ-UHFFFAOYSA-M 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- DYUOIGKJBBZBMU-UHFFFAOYSA-N methyl 2-[2-benzhydryl-4-(4-fluorophenyl)-1h-imidazol-5-yl]acetate Chemical compound COC(=O)CC=1NC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C1=CC=C(F)C=C1 DYUOIGKJBBZBMU-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 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
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum 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
- 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 239000002245 particle Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 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
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000036515 potency Effects 0.000 description 1
- 238000001556 precipitation Methods 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
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001525 receptor binding assay Methods 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
- 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
- 238000012163 sequencing technique Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium 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
- 239000011343 solid material Substances 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
- 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
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 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
- 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
- 125000004306 triazinyl group Chemical group 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
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-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
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- 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
- 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
- A61P19/06—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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Otolaryngology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0412198.4 | 2004-05-29 | ||
| GB0412198A GB0412198D0 (en) | 2004-05-29 | 2004-05-29 | Medicinal use of receptor ligands |
| GB0414194.1 | 2004-06-24 | ||
| GB0414194A GB0414194D0 (en) | 2004-06-24 | 2004-06-24 | Medicinal use of receptor ligands |
| GB0424016.4 | 2004-10-29 | ||
| GB0424016A GB0424016D0 (en) | 2004-10-29 | 2004-10-29 | Medicinal use of receptor ligands |
| PCT/EP2005/005882 WO2005116001A1 (en) | 2004-05-29 | 2005-05-30 | Substituted thiazoleacetic as crth2 ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2568742A1 true CA2568742A1 (en) | 2005-12-08 |
Family
ID=34968996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002568742A Abandoned CA2568742A1 (en) | 2004-05-29 | 2005-05-30 | Substituted thiazoleacetic as crth2 ligands |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20080119456A1 (enExample) |
| EP (1) | EP1758874A1 (enExample) |
| JP (1) | JP2008503447A (enExample) |
| KR (1) | KR20070044404A (enExample) |
| AU (1) | AU2005247610A1 (enExample) |
| BR (1) | BRPI0511671A (enExample) |
| CA (1) | CA2568742A1 (enExample) |
| CR (1) | CR8837A (enExample) |
| EA (1) | EA200602288A1 (enExample) |
| IL (1) | IL179693A0 (enExample) |
| MX (1) | MXPA06013924A (enExample) |
| NO (1) | NO20066049L (enExample) |
| WO (1) | WO2005116001A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0427381D0 (en) * | 2004-12-14 | 2005-01-19 | Novartis Ag | Organic compounds |
| UY30892A1 (es) * | 2007-02-07 | 2008-09-02 | Smithkline Beckman Corp | Inhibidores de la actividad akt |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| BRPI0907844B8 (pt) | 2008-02-22 | 2021-05-25 | Radius Health Inc | compostos e método para modular um receptor de andrógeno, processos de preparação e composição farmacêutica dos mesmos e seus usos |
| JP5535931B2 (ja) | 2008-10-27 | 2014-07-02 | 武田薬品工業株式会社 | 二環性化合物 |
| WO2010088331A1 (en) * | 2009-01-30 | 2010-08-05 | Glaxosmithkline Llc | Crystalline n-{(1-s)-2-amino-1-[(3-fluorophenyl)methyl]ethyl}-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride |
| EP2516416A1 (en) | 2009-12-23 | 2012-10-31 | Ironwood Pharmaceuticals, Inc. | Crth2 modulators |
| AU2011212813B2 (en) | 2010-02-04 | 2014-10-23 | Radius Health, Inc. | Selective androgen receptor modulators |
| SI2568806T1 (sl) | 2010-05-12 | 2016-09-30 | Radius Health, Inc. | Režimi zdravljenja |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| EP2621901B1 (en) | 2010-09-28 | 2015-07-29 | Radius Health, Inc | Selective androgen receptor modulators |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| CA2859284A1 (en) | 2011-12-16 | 2013-06-20 | Atopix Therapeutics Limited | Combination of a crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
| RS63311B1 (sr) | 2016-06-22 | 2022-07-29 | Ellipses Pharma Ltd | Ar+ metode lečenja raka dojke |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ID24390A (id) * | 1997-07-10 | 2000-07-13 | Janssen Pharmaceutica Nv | Turunan-turunan 6-azaurasil penghambat il-5 |
| HUP0004238A3 (en) * | 1997-11-28 | 2001-07-30 | Lg Chemical Ltd | Imidazole derivatives having an inhibitory activity for farnesyl transferase, process for preparation thereof and pharmaceutical compositions containing them |
| EP0987265A1 (en) * | 1998-09-18 | 2000-03-22 | Janssen Pharmaceutica N.V. | Interleukin-5 inhibiting 6-azauracil derivatives |
| EE200200057A (et) * | 1999-08-06 | 2003-04-15 | Janssen Pharmaceutica N.V. | Kasvutegurit IL-5 pärssiv asauratsiilderivaat, selle saamine ja kasutamine ravimi valmistamiseks ning seda sisaldav farmatseutiline kompositsioon |
| US7276526B2 (en) * | 2001-07-13 | 2007-10-02 | Bristol-Myers Squibb Pharma Company | Substituted thiazoles and oxazoles as corticotropin releasing hormone ligands |
| TW200307542A (en) * | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
-
2005
- 2005-05-30 BR BRPI0511671-6A patent/BRPI0511671A/pt not_active IP Right Cessation
- 2005-05-30 EP EP05748037A patent/EP1758874A1/en not_active Withdrawn
- 2005-05-30 EA EA200602288A patent/EA200602288A1/ru unknown
- 2005-05-30 MX MXPA06013924A patent/MXPA06013924A/es not_active Application Discontinuation
- 2005-05-30 KR KR1020067027509A patent/KR20070044404A/ko not_active Withdrawn
- 2005-05-30 CA CA002568742A patent/CA2568742A1/en not_active Abandoned
- 2005-05-30 JP JP2007513845A patent/JP2008503447A/ja not_active Withdrawn
- 2005-05-30 WO PCT/EP2005/005882 patent/WO2005116001A1/en not_active Ceased
- 2005-05-30 AU AU2005247610A patent/AU2005247610A1/en not_active Abandoned
- 2005-05-30 US US11/597,839 patent/US20080119456A1/en not_active Abandoned
-
2006
- 2006-11-29 IL IL179693A patent/IL179693A0/en unknown
- 2006-12-22 CR CR8837A patent/CR8837A/es unknown
- 2006-12-28 NO NO20066049A patent/NO20066049L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL179693A0 (en) | 2007-05-15 |
| MXPA06013924A (es) | 2007-07-18 |
| CR8837A (es) | 2008-03-18 |
| NO20066049L (no) | 2007-02-27 |
| EA200602288A1 (ru) | 2007-10-26 |
| EP1758874A1 (en) | 2007-03-07 |
| AU2005247610A1 (en) | 2005-12-08 |
| US20080119456A1 (en) | 2008-05-22 |
| JP2008503447A (ja) | 2008-02-07 |
| KR20070044404A (ko) | 2007-04-27 |
| WO2005116001A1 (en) | 2005-12-08 |
| BRPI0511671A (pt) | 2008-01-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1758571A1 (en) | Crth2 receptor ligands for therapeutic use | |
| JP6726226B2 (ja) | 複素環式アミンおよびその使用 | |
| US8022063B2 (en) | CRTH2 receptor ligands for medicinal uses | |
| KR100706735B1 (ko) | ｈＰＰＡＲ 알파 활성제로서 치환된 옥사졸 및 티아졸유도체 | |
| CA2568742A1 (en) | Substituted thiazoleacetic as crth2 ligands | |
| EP0091726B1 (en) | 5-substituted 1,2,4-oxadiazole derivatives, their preparation and pharmaceutical compositions containing them | |
| AU2007207055A1 (en) | Thiazoles as 11 beta-HSD1 inhibitors | |
| AU2003282754A1 (en) | Novel heterocyclic analogs of diphenylethylene compounds | |
| AU2005275279A1 (en) | Arylidenes for the treatment of estrogen related receptor-alpha mediated diseases | |
| US20080312220A1 (en) | Oxadiazole Derivatives with Crth2 Receptor Activity | |
| JP2004517100A (ja) | ｈＰＰＡＲアルファアゴニストとしての置換オキサゾールおよびチアゾール | |
| RU2268262C2 (ru) | Производные дигидронафталина и лекарственное средство, включающее указанные производные в качестве активного ингредиента | |
| WO2007062678A1 (en) | Phenoxyacetic acid derivatives as crth2 receptor ligands | |
| WO2007062797A1 (en) | Amino-substituted azo-heterocyclic compounds for treating inflammatory conditions | |
| EP0259085B1 (en) | 2-guanidino-4-arylthiazoles for treatment of peptic ulcers | |
| CA2214521A1 (en) | Quinoline derivatives as immunomodulators | |
| Kadam et al. | Evaluation of thiazole containing biaryl analogs as diacylglycerol acyltransferase 1 (DGAT1) inhibitors | |
| ZA200610597B (en) | Substituted thiazoleacetic as CRTH2 ligands | |
| JP2006515888A (ja) | アシルアミノチアゾール誘導体、その製造法およびベータ−アミロイドペプチド生成阻害剤としての用途 | |
| WO2007062677A1 (en) | Thiazolyl- and pyrimidinyl-acetic acids and their use as crth2 receptor ligands | |
| HK1107811A (en) | Substituted thiazoleacetic as crth2 ligands | |
| US3917593A (en) | N-alkenyl and N-alkynyl (2-quinolyl)thio-acetamides | |
| HK1107763B (en) | Crth2 receptor ligands for medicinal uses |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |