JP2017520538A - 新規キノリン誘導体及び神経変性疾患におけるそれらの使用 - Google Patents
新規キノリン誘導体及び神経変性疾患におけるそれらの使用 Download PDFInfo
- Publication number
- JP2017520538A JP2017520538A JP2016571149A JP2016571149A JP2017520538A JP 2017520538 A JP2017520538 A JP 2017520538A JP 2016571149 A JP2016571149 A JP 2016571149A JP 2016571149 A JP2016571149 A JP 2016571149A JP 2017520538 A JP2017520538 A JP 2017520538A
- Authority
- JP
- Japan
- Prior art keywords
- quinoline
- carboxylic acid
- amide
- cyclohexylmethyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims abstract description 10
- 208000015122 neurodegenerative disease Diseases 0.000 title description 5
- 230000004770 neurodegeneration Effects 0.000 title description 4
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- 101710189965 P2X purinoceptor 7 Proteins 0.000 claims abstract description 59
- 102100037602 P2X purinoceptor 7 Human genes 0.000 claims abstract description 58
- 238000011282 treatment Methods 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims description 387
- 238000000034 method Methods 0.000 claims description 176
- -1 —SR Chemical group 0.000 claims description 100
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 85
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 78
- 150000003839 salts Chemical class 0.000 claims description 77
- 229910052757 nitrogen Inorganic materials 0.000 claims description 61
- 201000010099 disease Diseases 0.000 claims description 42
- 125000005842 heteroatom Chemical group 0.000 claims description 42
- 229910052760 oxygen Inorganic materials 0.000 claims description 41
- 229910052717 sulfur Inorganic materials 0.000 claims description 41
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 39
- 239000011593 sulfur Substances 0.000 claims description 39
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 38
- 239000001301 oxygen Substances 0.000 claims description 38
- 229920006395 saturated elastomer Polymers 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 208000035475 disorder Diseases 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000001931 aliphatic group Chemical group 0.000 claims description 26
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 26
- 229910005965 SO 2 Inorganic materials 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000004429 atom Chemical group 0.000 claims description 20
- 230000000694 effects Effects 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 239000012472 biological sample Substances 0.000 claims description 8
- 201000006417 multiple sclerosis Diseases 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 7
- 201000008482 osteoarthritis Diseases 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 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 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 208000010125 myocardial infarction Diseases 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 230000009529 traumatic brain injury Effects 0.000 claims description 5
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010020751 Hypersensitivity Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 206010046851 Uveitis Diseases 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 125000002393 azetidinyl group Chemical group 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000003566 oxetanyl group Chemical group 0.000 claims description 3
- HDDHLRKCWLHXTN-OPILKIMUSA-N 6-chloro-n-[[(1s,3s)-1-hydroxy-3-methylcyclohexyl]methyl]-2-(3-hydroxy-3-methylpyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound C1[C@@H](C)CCC[C@@]1(O)CNC(=O)C1=C(Cl)C=CC2=NC(N3CC(C)(O)CC3)=CC=C12 HDDHLRKCWLHXTN-OPILKIMUSA-N 0.000 claims description 2
- BAHOQKHEWZJWME-WNSKOXEYSA-N 6-chloro-n-[[(1s,3s)-1-hydroxy-3-methylcyclohexyl]methyl]-2-(4-hydroxypiperidin-1-yl)quinoline-5-carboxamide Chemical compound C1[C@@H](C)CCC[C@@]1(O)CNC(=O)C1=C(Cl)C=CC2=NC(N3CCC(O)CC3)=CC=C12 BAHOQKHEWZJWME-WNSKOXEYSA-N 0.000 claims description 2
- GTFTZKPCYSYNOU-KIMHZCHSSA-N 6-chloro-n-[[(1s,3s)-1-hydroxy-3-methylcyclohexyl]methyl]-2-[(3r)-3-hydroxypyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound C1[C@@H](C)CCC[C@@]1(O)CNC(=O)C1=C(Cl)C=CC2=NC(N3C[C@H](O)CC3)=CC=C12 GTFTZKPCYSYNOU-KIMHZCHSSA-N 0.000 claims description 2
- GTFTZKPCYSYNOU-DFFLPILJSA-N 6-chloro-n-[[(1s,3s)-1-hydroxy-3-methylcyclohexyl]methyl]-2-[(3s)-3-hydroxypyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound C1[C@@H](C)CCC[C@@]1(O)CNC(=O)C1=C(Cl)C=CC2=NC(N3C[C@@H](O)CC3)=CC=C12 GTFTZKPCYSYNOU-DFFLPILJSA-N 0.000 claims description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
- 208000030814 Eating disease Diseases 0.000 claims description 2
- 208000034347 Faecal incontinence Diseases 0.000 claims description 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 2
- 206010026749 Mania Diseases 0.000 claims description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
- 206010046543 Urinary incontinence Diseases 0.000 claims description 2
- 208000026935 allergic disease Diseases 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 235000014632 disordered eating Nutrition 0.000 claims description 2
- 206010014599 encephalitis Diseases 0.000 claims description 2
- 230000009610 hypersensitivity Effects 0.000 claims description 2
- 208000036273 reactive airway disease Diseases 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 66
- 239000005557 antagonist Substances 0.000 abstract description 22
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 197
- 238000005481 NMR spectroscopy Methods 0.000 description 152
- 235000002639 sodium chloride Nutrition 0.000 description 77
- 239000003112 inhibitor Substances 0.000 description 43
- 229960005419 nitrogen Drugs 0.000 description 41
- 210000004027 cell Anatomy 0.000 description 39
- PDSSIVPBNXANSW-UHFFFAOYSA-N 2,6-dichloro-N-[(4,4-difluorocyclohexyl)methyl]quinoline-5-carboxamide Chemical compound ClC1=NC=2C=CC(=C(C=2C=C1)C(=O)NCC1CCC(CC1)(F)F)Cl PDSSIVPBNXANSW-UHFFFAOYSA-N 0.000 description 32
- 239000003814 drug Substances 0.000 description 29
- 239000000543 intermediate Substances 0.000 description 29
- 239000000243 solution Substances 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 23
- KVOTTZFPYQAYRW-ADLMAVQZSA-N 2,6-dichloro-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)Cl KVOTTZFPYQAYRW-ADLMAVQZSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- 239000004480 active ingredient Substances 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 125000001424 substituent group Chemical group 0.000 description 22
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- 208000002193 Pain Diseases 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 18
- 229940079593 drug Drugs 0.000 description 17
- 208000004296 neuralgia Diseases 0.000 description 17
- 208000024891 symptom Diseases 0.000 description 15
- CODLYTZBFZTYDB-UHFFFAOYSA-N 2,6-dichloro-N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]quinoline-5-carboxamide Chemical compound ClC1=NC=2C=CC(=C(C=2C=C1)C(=O)NCC1(CCC(CC1)(F)F)O)Cl CODLYTZBFZTYDB-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- CHHZYPZBIZZLFC-UHFFFAOYSA-N 2,6-dichloro-N-[(3,3-difluoro-1-hydroxycyclohexyl)methyl]quinoline-5-carboxamide Chemical compound ClC1=NC=2C=CC(=C(C=2C=C1)C(=O)NCC1(CC(CCC1)(F)F)O)Cl CHHZYPZBIZZLFC-UHFFFAOYSA-N 0.000 description 13
- KVOTTZFPYQAYRW-VOJFVSQTSA-N 2,6-dichloro-n-[[(1s,3s)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound C1[C@@H](C)CCC[C@@]1(O)CNC(=O)C1=C(Cl)C=CC2=NC(Cl)=CC=C12 KVOTTZFPYQAYRW-VOJFVSQTSA-N 0.000 description 13
- 230000036407 pain Effects 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 0 CN1CC(*)(*)C1 Chemical compound CN1CC(*)(*)C1 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 12
- 239000003826 tablet Substances 0.000 description 12
- 230000001225 therapeutic effect Effects 0.000 description 12
- 238000013459 approach Methods 0.000 description 11
- 239000002552 dosage form Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- XAAFYIOYLLPWMM-UHFFFAOYSA-N (4,4-difluorocyclohexyl)methanamine Chemical compound NCC1CCC(F)(F)CC1 XAAFYIOYLLPWMM-UHFFFAOYSA-N 0.000 description 10
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 238000000338 in vitro Methods 0.000 description 10
- 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 9
- 239000002775 capsule Substances 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 239000008101 lactose Substances 0.000 description 9
- 229940044551 receptor antagonist Drugs 0.000 description 9
- 239000002464 receptor antagonist Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- QIKNJIYYNGDZBR-UHFFFAOYSA-N 2,6-dichloro-N-[(4,4-difluoro-1-hydroxy-3-methylcyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(C(CC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)Cl)C)F QIKNJIYYNGDZBR-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 8
- 229910000024 caesium carbonate Inorganic materials 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- AVAWMINJNRAQFS-UHFFFAOYSA-N n,n-dimethylpyrrolidin-3-amine Chemical compound CN(C)C1CCNC1 AVAWMINJNRAQFS-UHFFFAOYSA-N 0.000 description 8
- OLFORMXISVHWRF-UHFFFAOYSA-N 2,6-dichloro-N-[(3,3-difluorocyclohexyl)methyl]quinoline-5-carboxamide Chemical compound ClC1=NC=2C=CC(=C(C=2C=C1)C(=O)NCC1CC(CCC1)(F)F)Cl OLFORMXISVHWRF-UHFFFAOYSA-N 0.000 description 7
- KVOTTZFPYQAYRW-UHFFFAOYSA-N 2,6-dichloro-n-[(1-hydroxy-3-methylcyclohexyl)methyl]quinoline-5-carboxamide Chemical compound C1C(C)CCCC1(O)CNC(=O)C1=C(Cl)C=CC2=NC(Cl)=CC=C12 KVOTTZFPYQAYRW-UHFFFAOYSA-N 0.000 description 7
- 102000004127 Cytokines Human genes 0.000 description 7
- 108090000695 Cytokines Proteins 0.000 description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 230000003042 antagnostic effect Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229910052805 deuterium Inorganic materials 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 230000003993 interaction Effects 0.000 description 7
- 239000002207 metabolite Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- XJHLPXOKKUNOQM-UHFFFAOYSA-N 2,6-dichloro-N-[[1-hydroxy-3-(trifluoromethyl)cyclohexyl]methyl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C(F)(F)F)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)Cl XJHLPXOKKUNOQM-UHFFFAOYSA-N 0.000 description 6
- DXYPZGNOLQPKSH-XVTZWQNCSA-N 6-chloro-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)N(C)C DXYPZGNOLQPKSH-XVTZWQNCSA-N 0.000 description 6
- TYVVUDSQBIAFBI-ZCCHDVMBSA-N 6-chloro-2-[(3S)-3-fluoropyrrolidin-1-yl]-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)F TYVVUDSQBIAFBI-ZCCHDVMBSA-N 0.000 description 6
- TUWDEXLFNQHRNR-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]-2-[3-(dimethylamino)cyclopentyl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1CC(CC1)N(C)C)F TUWDEXLFNQHRNR-UHFFFAOYSA-N 0.000 description 6
- KZDNPPJTLMCCDD-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(3-hydroxycyclopentyl)quinoline-5-carboxamide Chemical compound OC1CCC(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 KZDNPPJTLMCCDD-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- 102000002274 Matrix Metalloproteinases Human genes 0.000 description 6
- 108010000684 Matrix Metalloproteinases Proteins 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000002159 abnormal effect Effects 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 239000000556 agonist Substances 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000003937 drug carrier Substances 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 231100000252 nontoxic Toxicity 0.000 description 6
- 230000003000 nontoxic effect Effects 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- LZHJFZLHEGJWAU-UHFFFAOYSA-N quinoline-5-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=N1 LZHJFZLHEGJWAU-UHFFFAOYSA-N 0.000 description 6
- 239000007909 solid dosage form Substances 0.000 description 6
- IPHQKPMANJGZOB-UHFFFAOYSA-N 2,6-dichloroquinoline-5-carboxylic acid Chemical compound ClC1=CC=C2C(C(=O)O)=C(Cl)C=CC2=N1 IPHQKPMANJGZOB-UHFFFAOYSA-N 0.000 description 5
- CDDGNGVFPQRJJM-UHFFFAOYSA-N 3-fluoropyrrolidine Chemical compound FC1CCNC1 CDDGNGVFPQRJJM-UHFFFAOYSA-N 0.000 description 5
- TYVVUDSQBIAFBI-HVPFBLEYSA-N 6-chloro-2-[(3S)-3-fluoropyrrolidin-1-yl]-N-[(1-hydroxy-3-methylcyclohexyl)methyl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)F TYVVUDSQBIAFBI-HVPFBLEYSA-N 0.000 description 5
- JWYYLBNLUIBSIN-KZUDCZAMSA-N 6-chloro-N-[(3,3-difluorocyclohexyl)methyl]-2-[(3S)-3-fluoropyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)F)F JWYYLBNLUIBSIN-KZUDCZAMSA-N 0.000 description 5
- ITYHKFRRLPBRIT-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]-2-(3-oxocyclopentyl)quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1CC(CC1)=O)F ITYHKFRRLPBRIT-UHFFFAOYSA-N 0.000 description 5
- SUPUIFPUWMWANZ-MRXNPFEDSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[(3R)-3-(2-hydroxyethyl)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound OCC[C@H]1CCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 SUPUIFPUWMWANZ-MRXNPFEDSA-N 0.000 description 5
- GOZKOBXNHZQLCA-NYHFZMIOSA-N 6-chloro-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]-2-pyrrolidin-1-ylquinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CCCC1 GOZKOBXNHZQLCA-NYHFZMIOSA-N 0.000 description 5
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 5
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 5
- 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 5
- 102000015696 Interleukins Human genes 0.000 description 5
- 108010063738 Interleukins Proteins 0.000 description 5
- 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 5
- 241001465754 Metazoa Species 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 5
- 206010029240 Neuritis Diseases 0.000 description 5
- 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 5
- 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 5
- 206010040070 Septic Shock Diseases 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 230000001154 acute effect Effects 0.000 description 5
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 229940111134 coxibs Drugs 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 150000002617 leukotrienes Chemical class 0.000 description 5
- 229960000485 methotrexate Drugs 0.000 description 5
- 208000021722 neuropathic pain Diseases 0.000 description 5
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 230000004783 oxidative metabolism Effects 0.000 description 5
- 239000006187 pill Substances 0.000 description 5
- 238000002953 preparative HPLC Methods 0.000 description 5
- 230000000069 prophylactic effect Effects 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 229960002052 salbutamol Drugs 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 208000020431 spinal cord injury Diseases 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- CDDGNGVFPQRJJM-SCSAIBSYSA-N (3r)-3-fluoropyrrolidine Chemical compound F[C@@H]1CCNC1 CDDGNGVFPQRJJM-SCSAIBSYSA-N 0.000 description 4
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- MMSNEKOTSJRTRI-LLVKDONJSA-N 1-[(2r)-4-[5-[(4-fluorophenyl)methyl]thiophen-2-yl]but-3-yn-2-yl]-1-hydroxyurea Chemical compound S1C(C#C[C@@H](C)N(O)C(N)=O)=CC=C1CC1=CC=C(F)C=C1 MMSNEKOTSJRTRI-LLVKDONJSA-N 0.000 description 4
- OTWVFHZMWFGHSJ-UHFFFAOYSA-N 1-fluoropyrrolidine Chemical compound FN1CCCC1 OTWVFHZMWFGHSJ-UHFFFAOYSA-N 0.000 description 4
- FBCMQTVRVFURRH-UHFFFAOYSA-N 2,6-dichloro-N-[(3-cyclopropyl-1-hydroxycyclohexyl)methyl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C1CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)Cl FBCMQTVRVFURRH-UHFFFAOYSA-N 0.000 description 4
- QYRKRMYEUVBGGV-UHFFFAOYSA-N 2-(azetidin-1-yl)-6-chloro-N-[(3,3-difluoro-1-hydroxycyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CCC1)F QYRKRMYEUVBGGV-UHFFFAOYSA-N 0.000 description 4
- HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 4
- QOCVJGKPXKYAFO-UHFFFAOYSA-N 6-chloro-2-(3,3-difluoropyrrolidin-1-yl)quinoline-5-carboxylic acid Chemical compound ClC1=C(C=2C=CC(=NC=2C=C1)N1CC(CC1)(F)F)C(=O)O QOCVJGKPXKYAFO-UHFFFAOYSA-N 0.000 description 4
- TYVVUDSQBIAFBI-NSPSVTOZSA-N 6-chloro-2-(3-fluoropyrrolidin-1-yl)-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)F TYVVUDSQBIAFBI-NSPSVTOZSA-N 0.000 description 4
- LJKPLYHODNXCAL-UHFFFAOYSA-N 6-chloro-2-(cyclopenten-1-yl)-N-[(4,4-difluorocyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1=CCCC1)F LJKPLYHODNXCAL-UHFFFAOYSA-N 0.000 description 4
- TYVVUDSQBIAFBI-DOQJBMMISA-N 6-chloro-2-[(3R)-3-fluoropyrrolidin-1-yl]-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)F TYVVUDSQBIAFBI-DOQJBMMISA-N 0.000 description 4
- YUUZNBBYSFHHNS-SZQRVLIRSA-N 6-chloro-N-[(3,3-difluoro-1-hydroxycyclohexyl)methyl]-2-[(3S)-3-fluoropyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)F)F YUUZNBBYSFHHNS-SZQRVLIRSA-N 0.000 description 4
- WNBUCJAZSKUNSB-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(1-propan-2-ylpiperidin-4-yl)quinoline-5-carboxamide Chemical compound CC(C)N1CCC(CC1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 WNBUCJAZSKUNSB-UHFFFAOYSA-N 0.000 description 4
- URUMEZPYGTVCGV-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(3-hydroxypropyl)quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)CCCO)F URUMEZPYGTVCGV-UHFFFAOYSA-N 0.000 description 4
- AWFVIBSNEOOFBA-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(3-methoxypropoxy)quinoline-5-carboxamide Chemical compound COCCCOC1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 AWFVIBSNEOOFBA-UHFFFAOYSA-N 0.000 description 4
- MJYZLNZIWTZNKG-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(3-oxocyclopentyl)quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1CC(CC1)=O)F MJYZLNZIWTZNKG-UHFFFAOYSA-N 0.000 description 4
- NVTVMPNFPIZDHL-OAHLLOKOSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[(3R)-3-(hydroxymethyl)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound OC[C@@H]1CCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 NVTVMPNFPIZDHL-OAHLLOKOSA-N 0.000 description 4
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 4
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 4
- 208000023275 Autoimmune disease Diseases 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 4
- 102100027995 Collagenase 3 Human genes 0.000 description 4
- 108090000379 Fibroblast growth factor 2 Proteins 0.000 description 4
- 102000003974 Fibroblast growth factor 2 Human genes 0.000 description 4
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 4
- 208000019695 Migraine disease Diseases 0.000 description 4
- 208000019022 Mood disease Diseases 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 108010003541 Platelet Activating Factor Proteins 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 102100030416 Stromelysin-1 Human genes 0.000 description 4
- 102100028848 Stromelysin-2 Human genes 0.000 description 4
- 102100028847 Stromelysin-3 Human genes 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- 229960004436 budesonide Drugs 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000004113 cell culture Methods 0.000 description 4
- 210000003169 central nervous system Anatomy 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- MWQFEJPKXXQVRT-UHFFFAOYSA-N ethyl 1-[6-chloro-5-[(4,4-difluorocyclohexyl)methylcarbamoyl]quinolin-2-yl]piperidine-3-carboxylate Chemical compound CCOC(=O)C1CCCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 MWQFEJPKXXQVRT-UHFFFAOYSA-N 0.000 description 4
- CXNBZZMNUCSOHQ-UHFFFAOYSA-N ethyl 3-[[6-chloro-5-[(4,4-difluorocyclohexyl)methylcarbamoyl]quinolin-2-yl]amino]propanoate Chemical compound CCOC(=O)CCNC1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 CXNBZZMNUCSOHQ-UHFFFAOYSA-N 0.000 description 4
- 230000029142 excretion Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 230000001976 improved effect Effects 0.000 description 4
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 4
- 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 4
- 239000003701 inert diluent Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 206010027599 migraine Diseases 0.000 description 4
- 238000012544 monitoring process Methods 0.000 description 4
- 239000000346 nonvolatile oil Substances 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- 229960002657 orciprenaline Drugs 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- 208000033808 peripheral neuropathy Diseases 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 230000019491 signal transduction Effects 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- 238000011200 topical administration Methods 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 3
- CDDGNGVFPQRJJM-BYPYZUCNSA-N (3s)-3-fluoropyrrolidine Chemical compound F[C@H]1CCNC1 CDDGNGVFPQRJJM-BYPYZUCNSA-N 0.000 description 3
- AVAWMINJNRAQFS-LURJTMIESA-N (3s)-n,n-dimethylpyrrolidin-3-amine Chemical compound CN(C)[C@H]1CCNC1 AVAWMINJNRAQFS-LURJTMIESA-N 0.000 description 3
- YEYGMIWYLPSSKZ-UHFFFAOYSA-N 1-[6-chloro-5-[(4,4-difluorocyclohexyl)methylcarbamoyl]quinolin-2-yl]piperidine-3-carboxylic acid Chemical compound OC(=O)C1CCCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 YEYGMIWYLPSSKZ-UHFFFAOYSA-N 0.000 description 3
- BLXKBIQXWILCIT-UHFFFAOYSA-N 1-pyrrolidin-1-ium-3-ylpyrrolidin-1-ium;dichloride Chemical compound [Cl-].[Cl-].C1CCC[NH+]1C1C[NH2+]CC1 BLXKBIQXWILCIT-UHFFFAOYSA-N 0.000 description 3
- HABNIXAHSGYFJJ-FCDCVOMCSA-N 2-(2-amino-2-methyl-3-propan-2-ylpyrrolidin-1-yl)-6-chloro-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C(C(CC1)C(C)C)(N)C HABNIXAHSGYFJJ-FCDCVOMCSA-N 0.000 description 3
- GVOAOLOLWKOACQ-QDBJOMPGSA-N 2-(2-amino-3-cyclopropyl-2-methylpyrrolidin-1-yl)-6-chloro-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C(C(CC1)C1CC1)(N)C GVOAOLOLWKOACQ-QDBJOMPGSA-N 0.000 description 3
- GVOAOLOLWKOACQ-BLWCKECESA-N 2-(2-amino-3-cyclopropyl-2-methylpyrrolidin-1-yl)-6-chloro-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C(C(CC1)C1CC1)(N)C GVOAOLOLWKOACQ-BLWCKECESA-N 0.000 description 3
- VNIJWYBUENCFKQ-LERXBOGZSA-N 2-(2-amino-3-ethyl-2-methylpyrrolidin-1-yl)-6-chloro-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C(C(CC1)CC)(N)C VNIJWYBUENCFKQ-LERXBOGZSA-N 0.000 description 3
- VNIJWYBUENCFKQ-GXYJLNOBSA-N 2-(2-amino-3-ethyl-2-methylpyrrolidin-1-yl)-6-chloro-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C(C(CC1)CC)(N)C VNIJWYBUENCFKQ-GXYJLNOBSA-N 0.000 description 3
- GQSMJJYHSMJGFQ-UHFFFAOYSA-N 2-(3-acetamidopyrrolidin-1-yl)-6-chloro-N-[(4,4-difluorocyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)NC(C)=O)F GQSMJJYHSMJGFQ-UHFFFAOYSA-N 0.000 description 3
- IGYLYHVBMXRVSM-UHFFFAOYSA-N 2-(3-aminopyrrolidin-1-yl)-6-chloro-N-[(3,3-difluoro-1-hydroxycyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N)F IGYLYHVBMXRVSM-UHFFFAOYSA-N 0.000 description 3
- XSQOLOPTGSZRSW-UHFFFAOYSA-N 2-(azetidin-1-yl)-6-chloro-N-[(4,4-difluorocyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(F)CCC(CNC(=O)C2=C3C=CC(=NC3=CC=C2Cl)N2CCC2)CC1 XSQOLOPTGSZRSW-UHFFFAOYSA-N 0.000 description 3
- KVTUSMPNLUCCQO-UHFFFAOYSA-N 3,3-difluoropyrrolidine Chemical compound FC1(F)CCNC1 KVTUSMPNLUCCQO-UHFFFAOYSA-N 0.000 description 3
- OJAMZHLAZVLFER-UHFFFAOYSA-N 3-[[6-chloro-5-[(4,4-difluorocyclohexyl)methylcarbamoyl]quinolin-2-yl]amino]propanoic acid Chemical compound ClC=1C(=C2C=CC(=NC2=CC=1)NCCC(=O)O)C(NCC1CCC(CC1)(F)F)=O OJAMZHLAZVLFER-UHFFFAOYSA-N 0.000 description 3
- UGNWAMIMUVOFRH-UHFFFAOYSA-N 5-bromo-2,6-dichloroquinoline Chemical compound BrC1=C(Cl)C=CC2=NC(Cl)=CC=C21 UGNWAMIMUVOFRH-UHFFFAOYSA-N 0.000 description 3
- HYTXCSOYULSRSZ-UHFFFAOYSA-N 6-chloro-2-(3,3-difluoroazetidin-1-yl)-N-[(3,3-difluoro-1-hydroxycyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(C1)(F)F)F HYTXCSOYULSRSZ-UHFFFAOYSA-N 0.000 description 3
- BLZPNPLNGPYEGR-QKKBWIMNSA-N 6-chloro-2-(3,3-difluoropyrrolidin-1-yl)-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)(F)F BLZPNPLNGPYEGR-QKKBWIMNSA-N 0.000 description 3
- DXYPZGNOLQPKSH-SRGWNRLKSA-N 6-chloro-2-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)N(C)C DXYPZGNOLQPKSH-SRGWNRLKSA-N 0.000 description 3
- TYVVUDSQBIAFBI-KIMHZCHSSA-N 6-chloro-2-[(3R)-3-fluoropyrrolidin-1-yl]-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)F TYVVUDSQBIAFBI-KIMHZCHSSA-N 0.000 description 3
- DXYPZGNOLQPKSH-COYMHYPVSA-N 6-chloro-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N-[(1-hydroxy-3-methylcyclohexyl)methyl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)N(C)C DXYPZGNOLQPKSH-COYMHYPVSA-N 0.000 description 3
- GWCODOMKHGKHPI-UHFFFAOYSA-N 6-chloro-2-[3-(dimethylamino)cyclopentyl]-N-[(1-hydroxy-3-methylcyclohexyl)methyl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1CC(CC1)N(C)C GWCODOMKHGKHPI-UHFFFAOYSA-N 0.000 description 3
- DXYPZGNOLQPKSH-UHFFFAOYSA-N 6-chloro-2-[3-(dimethylamino)pyrrolidin-1-yl]-N-[(1-hydroxy-3-methylcyclohexyl)methyl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N(C)C DXYPZGNOLQPKSH-UHFFFAOYSA-N 0.000 description 3
- GGSJICQYKATLGM-CILRCCJJSA-N 6-chloro-2-[4-fluoro-2-(hydroxymethyl)pyrrolidin-1-yl]-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C(CC(C1)F)CO GGSJICQYKATLGM-CILRCCJJSA-N 0.000 description 3
- UEAZGIGNKMYPQQ-UHFFFAOYSA-N 6-chloro-2-cyclohexyl-N-[(4,4-difluorocyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(F)CCC(CNC(=O)C2=C3C=CC(=NC3=CC=C2Cl)C2CCCCC2)CC1 UEAZGIGNKMYPQQ-UHFFFAOYSA-N 0.000 description 3
- KMZJAZMJHPDDPI-UHFFFAOYSA-N 6-chloro-2-cyclopentyl-N-[(4,4-difluorocyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(F)CCC(CNC(=O)C2=C3C=CC(=NC3=CC=C2Cl)C2CCCC2)CC1 KMZJAZMJHPDDPI-UHFFFAOYSA-N 0.000 description 3
- YUUZNBBYSFHHNS-UHFFFAOYSA-N 6-chloro-N-[(3,3-difluoro-1-hydroxycyclohexyl)methyl]-2-(3-fluoropyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)F)F YUUZNBBYSFHHNS-UHFFFAOYSA-N 0.000 description 3
- PHNSLYJCOJNXGZ-UHFFFAOYSA-N 6-chloro-N-[(3,3-difluoro-1-hydroxycyclohexyl)methyl]-2-(3-pyrrolidin-1-ylpyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N1CCCC1)F PHNSLYJCOJNXGZ-UHFFFAOYSA-N 0.000 description 3
- JWYYLBNLUIBSIN-ARLHGKGLSA-N 6-chloro-N-[(3,3-difluorocyclohexyl)methyl]-2-[(3R)-3-fluoropyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)F)F JWYYLBNLUIBSIN-ARLHGKGLSA-N 0.000 description 3
- JDUIZBHPNSGERA-UHFFFAOYSA-N 6-chloro-N-[(3,3-difluorocyclohexyl)methyl]-2-[3-(2-hydroxyethyl)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound OCCC1CCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCCC(F)(F)C3)=C2C=C1 JDUIZBHPNSGERA-UHFFFAOYSA-N 0.000 description 3
- WCPRJMOSCPBMJT-CYBMUJFWSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]-2-[(3R)-3-fluoropyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)F)F WCPRJMOSCPBMJT-CYBMUJFWSA-N 0.000 description 3
- WCPRJMOSCPBMJT-ZDUSSCGKSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]-2-[(3S)-3-fluoropyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)F)F WCPRJMOSCPBMJT-ZDUSSCGKSA-N 0.000 description 3
- SJFYRKGHFBLSIK-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(1-methylpiperidin-4-yl)quinoline-5-carboxamide Chemical compound CN1CCC(CC1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 SJFYRKGHFBLSIK-UHFFFAOYSA-N 0.000 description 3
- HUAZFHPHEHPLDF-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(3-hydroxyprop-1-ynyl)quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C#CCO)F HUAZFHPHEHPLDF-UHFFFAOYSA-N 0.000 description 3
- WLACJKQBEMZCGS-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(3-hydroxypyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound OC1CCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 WLACJKQBEMZCGS-UHFFFAOYSA-N 0.000 description 3
- KMYWWFWOAKEBGZ-FZCLLLDFSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[(2S)-2-ethyl-3-(hydroxymethyl)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound CC[C@H]1C(CO)CCN1c1ccc2c(C(=O)NCC3CCC(F)(F)CC3)c(Cl)ccc2n1 KMYWWFWOAKEBGZ-FZCLLLDFSA-N 0.000 description 3
- PYQGFKNDEHIFLC-CQSZACIVSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[(3R)-3-fluoropyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)F)F PYQGFKNDEHIFLC-CQSZACIVSA-N 0.000 description 3
- PUYAVUFSDFVGJW-INIZCTEOSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound CN(C)[C@H]1CCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 PUYAVUFSDFVGJW-INIZCTEOSA-N 0.000 description 3
- NLFBIMBOEPGOFW-HNNXBMFYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[(3S)-3-(methylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound CN[C@H]1CCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 NLFBIMBOEPGOFW-HNNXBMFYSA-N 0.000 description 3
- DQCNGLPIMYXNBG-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[4-fluoro-2-(hydroxymethyl)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C(CC(C1)F)CO)F DQCNGLPIMYXNBG-UHFFFAOYSA-N 0.000 description 3
- NRDZOWINXSSAGN-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[[3-(dimethylamino)-3-oxopropyl]amino]quinoline-5-carboxamide Chemical compound CN(C)C(=O)CCNC1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 NRDZOWINXSSAGN-UHFFFAOYSA-N 0.000 description 3
- HHXTWKFPIWNRQA-FNHSPDNWSA-N 6-chloro-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]-2-(3-hydroxy-2-methylpyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C(C(CC1)O)C HHXTWKFPIWNRQA-FNHSPDNWSA-N 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
- 208000020925 Bipolar disease Diseases 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 3
- 102100031111 Disintegrin and metalloproteinase domain-containing protein 17 Human genes 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 208000001640 Fibromyalgia Diseases 0.000 description 3
- 206010019233 Headaches Diseases 0.000 description 3
- 108060003951 Immunoglobulin Proteins 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- 206010065390 Inflammatory pain Diseases 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 3
- HABNIXAHSGYFJJ-VTGPFZJWSA-N O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C(C(CC1)C(C)C)(N)C Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C(C(CC1)C(C)C)(N)C HABNIXAHSGYFJJ-VTGPFZJWSA-N 0.000 description 3
- 208000001132 Osteoporosis Diseases 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229930012538 Paclitaxel Natural products 0.000 description 3
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 3
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 206010036376 Postherpetic Neuralgia Diseases 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 206010043269 Tension headache Diseases 0.000 description 3
- 208000008548 Tension-Type Headache Diseases 0.000 description 3
- 229960001138 acetylsalicylic acid Drugs 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000048 adrenergic agonist Substances 0.000 description 3
- 235000010443 alginic acid Nutrition 0.000 description 3
- 229920000615 alginic acid Polymers 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000004419 alkynylene group Chemical group 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
- 239000000935 antidepressant agent Substances 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 208000010668 atopic eczema Diseases 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 235000019437 butane-1,3-diol Nutrition 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 229960000590 celecoxib Drugs 0.000 description 3
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940110456 cocoa butter Drugs 0.000 description 3
- 235000019868 cocoa butter Nutrition 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 125000004431 deuterium atom Chemical group 0.000 description 3
- 229960001259 diclofenac Drugs 0.000 description 3
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 3
- 208000037765 diseases and disorders Diseases 0.000 description 3
- 239000012154 double-distilled water Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000002158 endotoxin Substances 0.000 description 3
- 239000003623 enhancer Substances 0.000 description 3
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 229960002848 formoterol Drugs 0.000 description 3
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 231100000869 headache Toxicity 0.000 description 3
- 229960001340 histamine Drugs 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 102000018358 immunoglobulin Human genes 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 3
- 229960000991 ketoprofen Drugs 0.000 description 3
- VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 229920006008 lipopolysaccharide Polymers 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 230000036651 mood Effects 0.000 description 3
- 229960002009 naproxen Drugs 0.000 description 3
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 3
- 210000005036 nerve Anatomy 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 125000000160 oxazolidinyl group Chemical group 0.000 description 3
- 229960001592 paclitaxel Drugs 0.000 description 3
- 229960005489 paracetamol Drugs 0.000 description 3
- 230000001575 pathological effect Effects 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 229960004622 raloxifene Drugs 0.000 description 3
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 229960000371 rofecoxib Drugs 0.000 description 3
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 3
- UHSKFQJFRQCDBE-UHFFFAOYSA-N ropinirole Chemical compound CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 UHSKFQJFRQCDBE-UHFFFAOYSA-N 0.000 description 3
- 229960004017 salmeterol Drugs 0.000 description 3
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 3
- 230000036303 septic shock Effects 0.000 description 3
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 3
- 229960002073 sertraline Drugs 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 229960003329 sulfinpyrazone Drugs 0.000 description 3
- MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 3
- 229960000195 terbutaline Drugs 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 208000004371 toothache Diseases 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 229960002004 valdecoxib Drugs 0.000 description 3
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- ZEYYDOLCHFETHQ-JOCHJYFZSA-N (2r)-2-cyclopentyl-2-[4-(quinolin-2-ylmethoxy)phenyl]acetic acid Chemical compound C1([C@@H](C(=O)O)C=2C=CC(OCC=3N=C4C=CC=CC4=CC=3)=CC=2)CCCC1 ZEYYDOLCHFETHQ-JOCHJYFZSA-N 0.000 description 2
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 description 2
- AVAWMINJNRAQFS-ZCFIWIBFSA-N (3r)-n,n-dimethylpyrrolidin-3-amine Chemical compound CN(C)[C@@H]1CCNC1 AVAWMINJNRAQFS-ZCFIWIBFSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- RPMVELKOENZIBB-UHFFFAOYSA-N 1,2-dimethylpyrrolidin-3-amine Chemical compound CC1C(N)CCN1C RPMVELKOENZIBB-UHFFFAOYSA-N 0.000 description 2
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 2
- JKNXMPSMAZUQMJ-UHFFFAOYSA-N 1-ethyl-2-methylpyrrolidine Chemical compound CCN1CCCC1C JKNXMPSMAZUQMJ-UHFFFAOYSA-N 0.000 description 2
- VSWPGAIWKHPTKX-UHFFFAOYSA-N 1-methyl-10-[2-(4-methyl-1-piperazinyl)-1-oxoethyl]-5H-thieno[3,4-b][1,5]benzodiazepin-4-one Chemical compound C1CN(C)CCN1CC(=O)N1C2=CC=CC=C2NC(=O)C2=CSC(C)=C21 VSWPGAIWKHPTKX-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- FCVPXRLVKIHPID-UHFFFAOYSA-N 2,6-di(cyclohexen-1-yl)-N-[(4,4-difluorocyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(F)CCC(CNC(=O)c2c(ccc3nc(ccc23)C2=CCCCC2)C2=CCCCC2)CC1 FCVPXRLVKIHPID-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- YGWFCQYETHJKNX-UHFFFAOYSA-N 2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1h-imidazol-3-ium;chloride Chemical compound [Cl-].CC1=CC(C(C)(C)C)=CC(C)=C1CC1=NCC[NH2+]1 YGWFCQYETHJKNX-UHFFFAOYSA-N 0.000 description 2
- JIRGUUPYPCFZOR-UHFFFAOYSA-N 2-[3-(azetidin-1-yl)cyclopentyl]-6-chloro-N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1CC(CC1)N1CCC1)F JIRGUUPYPCFZOR-UHFFFAOYSA-N 0.000 description 2
- IXGBYMAUBXEHCB-UHFFFAOYSA-N 2-[3-(azetidin-1-yl)cyclopentyl]-6-chloro-N-[(4,4-difluorocyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1CC(CC1)N1CCC1)F IXGBYMAUBXEHCB-UHFFFAOYSA-N 0.000 description 2
- VKUYLANQOAKALN-UHFFFAOYSA-N 2-[benzyl-(4-methoxyphenyl)sulfonylamino]-n-hydroxy-4-methylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(CC(C)C)C(=O)NO)CC1=CC=CC=C1 VKUYLANQOAKALN-UHFFFAOYSA-N 0.000 description 2
- XTDKZSUYCXHXJM-UHFFFAOYSA-N 2-methoxyoxane Chemical compound COC1CCCCO1 XTDKZSUYCXHXJM-UHFFFAOYSA-N 0.000 description 2
- ZGZMKFFPYZEFCM-UHFFFAOYSA-N 2-methyl-2-propylpyrrolidin-1-amine Chemical compound CC1(N(CCC1)N)CCC ZGZMKFFPYZEFCM-UHFFFAOYSA-N 0.000 description 2
- XFLSUQGAZBASBN-UHFFFAOYSA-N 2-methylpyrrolidin-1-amine Chemical compound CC1CCCN1N XFLSUQGAZBASBN-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- AWJJLYZBWRIBCZ-UGTJMOTHSA-N 3'-O-(4-Benzoyl)benzoyl ATP Chemical compound O([C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=2N=CN=C(C=2N=C1)N)C(=O)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 AWJJLYZBWRIBCZ-UGTJMOTHSA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- BIAVGWDGIJKWRM-FQEVSTJZSA-N 3-hydroxy-2-phenyl-n-[(1s)-1-phenylpropyl]quinoline-4-carboxamide Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(O)C=1C1=CC=CC=C1 BIAVGWDGIJKWRM-FQEVSTJZSA-N 0.000 description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- MBLJFKQACMILLC-UHFFFAOYSA-N 4-[[3-[[4-[2-(4-hydroxyphenyl)propan-2-yl]phenoxy]methyl]phenyl]methoxy]benzenecarboximidamide Chemical compound C=1C=C(OCC=2C=C(COC=3C=CC(=CC=3)C(N)=N)C=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 MBLJFKQACMILLC-UHFFFAOYSA-N 0.000 description 2
- 102000004023 5-Lipoxygenase-Activating Proteins Human genes 0.000 description 2
- 108090000411 5-Lipoxygenase-Activating Proteins Proteins 0.000 description 2
- WWAUGFBTZQZNLN-UHFFFAOYSA-N 6-chloro-2-(3,6-dihydro-2H-pyran-4-yl)quinoline-5-carboxylic acid Chemical compound ClC1=C(C=2C=CC(=NC=2C=C1)C=1CCOCC=1)C(=O)O WWAUGFBTZQZNLN-UHFFFAOYSA-N 0.000 description 2
- HQKKNVIJKBGTIA-UHFFFAOYSA-N 6-chloro-2-(3-fluoropyrrolidin-1-yl)quinoline-5-carboxylic acid Chemical compound ClC1=C(C=2C=CC(=NC=2C=C1)N1CC(CC1)F)C(=O)O HQKKNVIJKBGTIA-UHFFFAOYSA-N 0.000 description 2
- KIDKIWDNMCSDIJ-WNSKOXEYSA-N 6-chloro-2-(cyclopenten-1-yl)-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1=CCCC1 KIDKIWDNMCSDIJ-WNSKOXEYSA-N 0.000 description 2
- DXYPZGNOLQPKSH-HOZJOUCCSA-N 6-chloro-2-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)N(C)C DXYPZGNOLQPKSH-HOZJOUCCSA-N 0.000 description 2
- DXYPZGNOLQPKSH-UAVUOLJFSA-N 6-chloro-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)N(C)C DXYPZGNOLQPKSH-UAVUOLJFSA-N 0.000 description 2
- TYVVUDSQBIAFBI-DFFLPILJSA-N 6-chloro-2-[(3S)-3-fluoropyrrolidin-1-yl]-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)F TYVVUDSQBIAFBI-DFFLPILJSA-N 0.000 description 2
- DBTLYCXOIBYMIB-UHFFFAOYSA-N 6-chloro-2-[3-(1-hydroxyethyl)pyrrolidin-1-yl]quinoline-5-carboxylic acid Chemical compound ClC1=C(C=2C=CC(=NC=2C=C1)N1CC(CC1)C(C)O)C(=O)O DBTLYCXOIBYMIB-UHFFFAOYSA-N 0.000 description 2
- ZKFSZWBFBQMIDV-UHFFFAOYSA-N 6-chloro-2-[3-(diethylamino)pyrrolidin-1-yl]-N-[(3,3-difluoro-1-hydroxycyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N(CC)CC)F ZKFSZWBFBQMIDV-UHFFFAOYSA-N 0.000 description 2
- DXYPZGNOLQPKSH-DZNFTPFFSA-N 6-chloro-2-[3-(dimethylamino)pyrrolidin-1-yl]-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N(C)C DXYPZGNOLQPKSH-DZNFTPFFSA-N 0.000 description 2
- VHJMPCGVUPMYFF-UHFFFAOYSA-N 6-chloro-2-[3-(dimethylamino)pyrrolidin-1-yl]-N-[[1-hydroxy-3-(trifluoromethyl)cyclohexyl]methyl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C(F)(F)F)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N(C)C VHJMPCGVUPMYFF-UHFFFAOYSA-N 0.000 description 2
- DROACAZYEHUJRQ-UHFFFAOYSA-N 6-chloro-2-cyclopentylquinoline-5-carboxylic acid Chemical compound ClC1=C(C=2C=CC(=NC=2C=C1)C1CCCC1)C(=O)O DROACAZYEHUJRQ-UHFFFAOYSA-N 0.000 description 2
- UDDJHJQIEGSWNI-UHFFFAOYSA-N 6-chloro-N-[(1-hydroxy-3-methylcyclohexyl)methyl]-2-(3-oxocyclopenten-1-yl)quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1=CC(CC1)=O UDDJHJQIEGSWNI-UHFFFAOYSA-N 0.000 description 2
- ZBGLMKJQBKZBIV-UHFFFAOYSA-N 6-chloro-N-[(1-hydroxy-3-methylcyclohexyl)methyl]-2-(3-oxocyclopentyl)quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1CC(CC1)=O ZBGLMKJQBKZBIV-UHFFFAOYSA-N 0.000 description 2
- FRNCVZBYBCYMMN-UHFFFAOYSA-N 6-chloro-N-[(1-hydroxy-3-methylcyclohexyl)methyl]-2-(3-pyrrolidin-1-ylpyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N1CCCC1 FRNCVZBYBCYMMN-UHFFFAOYSA-N 0.000 description 2
- WYWXVRPONGIPBX-UHFFFAOYSA-N 6-chloro-N-[(3,3-difluoro-1-hydroxycyclohexyl)methyl]-2-(3,3-difluoropyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)(F)F)F WYWXVRPONGIPBX-UHFFFAOYSA-N 0.000 description 2
- YUUZNBBYSFHHNS-CRIUFTBBSA-N 6-chloro-N-[(3,3-difluoro-1-hydroxycyclohexyl)methyl]-2-[(3R)-3-fluoropyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)F)F YUUZNBBYSFHHNS-CRIUFTBBSA-N 0.000 description 2
- GZMIZTLJWWAOER-UHFFFAOYSA-N 6-chloro-N-[(3,3-difluoro-1-hydroxycyclohexyl)methyl]-2-[3-(dimethylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N(C)C)F GZMIZTLJWWAOER-UHFFFAOYSA-N 0.000 description 2
- JWYYLBNLUIBSIN-UHFFFAOYSA-N 6-chloro-N-[(3,3-difluorocyclohexyl)methyl]-2-(3-fluoropyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)F)F JWYYLBNLUIBSIN-UHFFFAOYSA-N 0.000 description 2
- HGGIFHQUEAQGQN-UHFFFAOYSA-N 6-chloro-N-[(3,3-difluorocyclohexyl)methyl]-2-(3-pyrrolidin-1-ylpyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N1CCCC1)F HGGIFHQUEAQGQN-UHFFFAOYSA-N 0.000 description 2
- HIJHUAGJROKSAA-UHFFFAOYSA-N 6-chloro-N-[(3,3-difluorocyclohexyl)methyl]-2-[3-(hydroxymethyl)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound OCC1CCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCCC(F)(F)C3)=C2C=C1 HIJHUAGJROKSAA-UHFFFAOYSA-N 0.000 description 2
- PVHXWOIFGTVYHS-UHFFFAOYSA-N 6-chloro-N-[(3-cyclopropyl-1-hydroxycyclohexyl)methyl]-2-[3-(dimethylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C1CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N(C)C PVHXWOIFGTVYHS-UHFFFAOYSA-N 0.000 description 2
- GSCRERPRNPOCLN-YZGUTLMUSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxy-3-methylcyclohexyl)methyl]-2-[(3R)-3-fluoropyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(C(CC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)F)C)F GSCRERPRNPOCLN-YZGUTLMUSA-N 0.000 description 2
- GSCRERPRNPOCLN-GJGORFQUSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxy-3-methylcyclohexyl)methyl]-2-[(3S)-3-fluoropyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(C(CC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)F)C)F GSCRERPRNPOCLN-GJGORFQUSA-N 0.000 description 2
- NWYACHXMGWYMFH-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]-2-(3,3-difluoropyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)(F)F)F NWYACHXMGWYMFH-UHFFFAOYSA-N 0.000 description 2
- NNPXFCQMJMHWDZ-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]-2-(3-methoxypropoxy)quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)OCCCOC)F NNPXFCQMJMHWDZ-UHFFFAOYSA-N 0.000 description 2
- RGVVUTQLYFPTNW-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]-2-(3-pyrrolidin-1-ylpyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N1CCCC1)F RGVVUTQLYFPTNW-UHFFFAOYSA-N 0.000 description 2
- ZSMWSNOOFULQSA-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]-2-[3-(dimethylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N(C)C)F ZSMWSNOOFULQSA-UHFFFAOYSA-N 0.000 description 2
- IXYWADHVFIZWQP-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(1-propan-2-yl-3,6-dihydro-2H-pyridin-4-yl)quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C=1CCN(CC=1)C(C)C)F IXYWADHVFIZWQP-UHFFFAOYSA-N 0.000 description 2
- LKOLPIPFWSTMAO-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(2-hydroxyethylamino)quinoline-5-carboxamide Chemical compound OCCNC1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 LKOLPIPFWSTMAO-UHFFFAOYSA-N 0.000 description 2
- VITAFGZXCYTNKU-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(2-methoxyethoxy)quinoline-5-carboxamide Chemical compound COCCOC1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 VITAFGZXCYTNKU-UHFFFAOYSA-N 0.000 description 2
- FSZBWUFOVGIKHN-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(2-methoxyethylamino)quinoline-5-carboxamide Chemical compound COCCNC1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 FSZBWUFOVGIKHN-UHFFFAOYSA-N 0.000 description 2
- VFXGFTOLRYPLON-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(3-hydroxypropylamino)quinoline-5-carboxamide Chemical compound OCCCNC1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 VFXGFTOLRYPLON-UHFFFAOYSA-N 0.000 description 2
- WPHHNUFPOWHRGY-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(3-methoxypropylamino)quinoline-5-carboxamide Chemical compound COCCCNC1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 WPHHNUFPOWHRGY-UHFFFAOYSA-N 0.000 description 2
- NYUOUSPLMMYXFY-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(3-oxocyclopenten-1-yl)quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1=CC(CC1)=O)F NYUOUSPLMMYXFY-UHFFFAOYSA-N 0.000 description 2
- GKHPCHCVFIILLJ-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(3-pyrrolidin-1-ylcyclopentyl)quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1CC(CC1)N1CCCC1)F GKHPCHCVFIILLJ-UHFFFAOYSA-N 0.000 description 2
- MHCGQGRAJAZFLU-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(3-pyrrolidin-1-ylpyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound FC1(F)CCC(CNC(=O)C2=C3C=CC(=NC3=CC=C2Cl)N2CCC(C2)N2CCCC2)CC1 MHCGQGRAJAZFLU-UHFFFAOYSA-N 0.000 description 2
- VDXLZCRZRZAHMA-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(oxan-4-yl)quinoline-5-carboxamide Chemical compound FC1(F)CCC(CNC(=O)C2=C3C=CC(=NC3=CC=C2Cl)C2CCOCC2)CC1 VDXLZCRZRZAHMA-UHFFFAOYSA-N 0.000 description 2
- KMYWWFWOAKEBGZ-OTOKDRCRSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[(2R)-2-ethyl-3-(hydroxymethyl)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound CC[C@@H]1C(CO)CCN1c1ccc2c(C(=O)NCC3CCC(F)(F)CC3)c(Cl)ccc2n1 KMYWWFWOAKEBGZ-OTOKDRCRSA-N 0.000 description 2
- PUYAVUFSDFVGJW-MRXNPFEDSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound CN(C)[C@@H]1CCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 PUYAVUFSDFVGJW-MRXNPFEDSA-N 0.000 description 2
- NLFBIMBOEPGOFW-OAHLLOKOSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[(3R)-3-(methylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound CN[C@@H]1CCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 NLFBIMBOEPGOFW-OAHLLOKOSA-N 0.000 description 2
- SUPUIFPUWMWANZ-INIZCTEOSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[(3S)-3-(2-hydroxyethyl)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound OCC[C@@H]1CCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 SUPUIFPUWMWANZ-INIZCTEOSA-N 0.000 description 2
- NVTVMPNFPIZDHL-HNNXBMFYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[(3S)-3-(hydroxymethyl)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound OC[C@H]1CCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 NVTVMPNFPIZDHL-HNNXBMFYSA-N 0.000 description 2
- PYQGFKNDEHIFLC-AWEZNQCLSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[(3S)-3-fluoropyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)F)F PYQGFKNDEHIFLC-AWEZNQCLSA-N 0.000 description 2
- MHHCXJKUKZNQTR-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[3-(difluoromethyl)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)C(F)F)F MHHCXJKUKZNQTR-UHFFFAOYSA-N 0.000 description 2
- NLFBIMBOEPGOFW-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-[3-(methylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound CNC1CCN(C1)C1=NC2=CC=C(Cl)C(C(=O)NCC3CCC(F)(F)CC3)=C2C=C1 NLFBIMBOEPGOFW-UHFFFAOYSA-N 0.000 description 2
- TUWPGNUFYSLYGW-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-piperidin-4-ylquinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1CCNCC1)F TUWPGNUFYSLYGW-UHFFFAOYSA-N 0.000 description 2
- HHXTWKFPIWNRQA-XDSHLONASA-N 6-chloro-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]-2-[(2S)-3-hydroxy-2-methylpyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1[C@H](C(CC1)O)C HHXTWKFPIWNRQA-XDSHLONASA-N 0.000 description 2
- XWVNNGZGEXVXFB-RYUVBPIJSA-N 6-chloro-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]-2-[(3R)-3-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)C(C)(C)O XWVNNGZGEXVXFB-RYUVBPIJSA-N 0.000 description 2
- XWVNNGZGEXVXFB-LEHBWIKQSA-N 6-chloro-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]-2-[(3S)-3-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)C(C)(C)O XWVNNGZGEXVXFB-LEHBWIKQSA-N 0.000 description 2
- GOZKOBXNHZQLCA-IVZQSRNASA-N 6-chloro-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]-2-pyrrolidin-1-ylquinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CCCC1 GOZKOBXNHZQLCA-IVZQSRNASA-N 0.000 description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 2
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 108091007505 ADAM17 Proteins 0.000 description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- 102100028116 Amine oxidase [flavin-containing] B Human genes 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 229940127398 Angiotensin 2 Receptor Antagonists Drugs 0.000 description 2
- 102100030988 Angiotensin-converting enzyme Human genes 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 102100022718 Atypical chemokine receptor 2 Human genes 0.000 description 2
- MBUVEWMHONZEQD-UHFFFAOYSA-N Azeptin Chemical compound C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 MBUVEWMHONZEQD-UHFFFAOYSA-N 0.000 description 2
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 2
- 102100025074 C-C chemokine receptor-like 2 Human genes 0.000 description 2
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229940127291 Calcium channel antagonist Drugs 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 102000005600 Cathepsins Human genes 0.000 description 2
- 108010084457 Cathepsins Proteins 0.000 description 2
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 description 2
- 208000000094 Chronic Pain Diseases 0.000 description 2
- LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 108060005980 Collagenase Proteins 0.000 description 2
- 102000029816 Collagenase Human genes 0.000 description 2
- 108050005238 Collagenase 3 Proteins 0.000 description 2
- 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 2
- 208000011231 Crohn disease Diseases 0.000 description 2
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 description 2
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000018233 Fibroblast Growth Factor Human genes 0.000 description 2
- 108050007372 Fibroblast Growth Factor Proteins 0.000 description 2
- 108010026132 Gelatinases Proteins 0.000 description 2
- 102000013382 Gelatinases Human genes 0.000 description 2
- 206010018364 Glomerulonephritis Diseases 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
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 208000035895 Guillain-Barré syndrome Diseases 0.000 description 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 2
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 101000768078 Homo sapiens Amine oxidase [flavin-containing] B Proteins 0.000 description 2
- 101000678892 Homo sapiens Atypical chemokine receptor 2 Proteins 0.000 description 2
- 101001125071 Homo sapiens Neuromedin-K receptor Proteins 0.000 description 2
- 101001098175 Homo sapiens P2X purinoceptor 7 Proteins 0.000 description 2
- 101000988419 Homo sapiens cAMP-specific 3',5'-cyclic phosphodiesterase 4D Proteins 0.000 description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
- 101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 description 2
- 102000014429 Insulin-like growth factor Human genes 0.000 description 2
- 108010008212 Integrin alpha4beta1 Proteins 0.000 description 2
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- 239000005411 L01XE02 - Gefitinib Substances 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 101150014058 MMP1 gene Proteins 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 108010076497 Matrix Metalloproteinase 10 Proteins 0.000 description 2
- 108010076502 Matrix Metalloproteinase 11 Proteins 0.000 description 2
- 108010076503 Matrix Metalloproteinase 13 Proteins 0.000 description 2
- 102000000422 Matrix Metalloproteinase 3 Human genes 0.000 description 2
- 108010016160 Matrix Metalloproteinase 3 Proteins 0.000 description 2
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 description 2
- 206010049567 Miller Fisher syndrome Diseases 0.000 description 2
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 description 2
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 2
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 2
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 2
- DJDFFEBSKJCGHC-UHFFFAOYSA-N Naphazoline Chemical compound Cl.C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 DJDFFEBSKJCGHC-UHFFFAOYSA-N 0.000 description 2
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 description 2
- 208000036110 Neuroinflammatory disease Diseases 0.000 description 2
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 description 2
- 102100029409 Neuromedin-K receptor Human genes 0.000 description 2
- 108030001564 Neutrophil collagenases Proteins 0.000 description 2
- 102000056189 Neutrophil collagenases Human genes 0.000 description 2
- 102000006538 Nitric Oxide Synthase Type I Human genes 0.000 description 2
- 108010008858 Nitric Oxide Synthase Type I Proteins 0.000 description 2
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 2
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 2
- 239000004264 Petrolatum Substances 0.000 description 2
- 208000004983 Phantom Limb Diseases 0.000 description 2
- 206010056238 Phantom pain Diseases 0.000 description 2
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 108091000080 Phosphotransferase Proteins 0.000 description 2
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 2
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 2
- 108010029485 Protein Isoforms Proteins 0.000 description 2
- 102000001708 Protein Isoforms Human genes 0.000 description 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
- 101100545004 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YSP2 gene Proteins 0.000 description 2
- 206010040047 Sepsis Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- 101710108790 Stromelysin-1 Proteins 0.000 description 2
- 101710108792 Stromelysin-2 Proteins 0.000 description 2
- 108050005271 Stromelysin-3 Proteins 0.000 description 2
- 102100037346 Substance-P receptor Human genes 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000150 Sympathomimetic Substances 0.000 description 2
- 102000003141 Tachykinin Human genes 0.000 description 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 102000002689 Toll-like receptor Human genes 0.000 description 2
- 108020000411 Toll-like receptor Proteins 0.000 description 2
- 108010009583 Transforming Growth Factors Proteins 0.000 description 2
- 102000009618 Transforming Growth Factors Human genes 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- 229940122598 Tryptase inhibitor Drugs 0.000 description 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 description 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 2
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 2
- YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 description 2
- NZDMRJGAFPUTMZ-UHFFFAOYSA-N [1-(3,4-dihydroxyphenyl)-1-hydroxybutan-2-yl]azanium;chloride Chemical compound [Cl-].CCC([NH3+])C(O)C1=CC=C(O)C(O)=C1 NZDMRJGAFPUTMZ-UHFFFAOYSA-N 0.000 description 2
- 229960004150 aciclovir Drugs 0.000 description 2
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
- 208000005298 acute pain Diseases 0.000 description 2
- 229940126157 adrenergic receptor agonist Drugs 0.000 description 2
- 229940009456 adriamycin Drugs 0.000 description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
- 108010003059 aggrecanase Proteins 0.000 description 2
- 229940072056 alginate Drugs 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 229960003459 allopurinol Drugs 0.000 description 2
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- PECIYKGSSMCNHN-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=NC=N[C]21.O=C1N(C)C(=O)N(C)C2=NC=N[C]21 PECIYKGSSMCNHN-UHFFFAOYSA-N 0.000 description 2
- 229960003556 aminophylline Drugs 0.000 description 2
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 2
- 229960000836 amitriptyline Drugs 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000007131 anti Alzheimer effect Effects 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 230000000340 anti-metabolite Effects 0.000 description 2
- 229940035678 anti-parkinson drug Drugs 0.000 description 2
- 230000000692 anti-sense effect Effects 0.000 description 2
- 229960002708 antigout preparations Drugs 0.000 description 2
- 229940100197 antimetabolite Drugs 0.000 description 2
- 239000002256 antimetabolite Substances 0.000 description 2
- 239000003080 antimitotic agent Substances 0.000 description 2
- 229940127218 antiplatelet drug Drugs 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- GXDALQBWZGODGZ-UHFFFAOYSA-N astemizole Chemical compound C1=CC(OC)=CC=C1CCN1CCC(NC=2N(C3=CC=CC=C3N=2)CC=2C=CC(F)=CC=2)CC1 GXDALQBWZGODGZ-UHFFFAOYSA-N 0.000 description 2
- 210000001130 astrocyte Anatomy 0.000 description 2
- AUJRCFUBUPVWSZ-XTZHGVARSA-M auranofin Chemical compound CCP(CC)(CC)=[Au]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O AUJRCFUBUPVWSZ-XTZHGVARSA-M 0.000 description 2
- 229960005207 auranofin Drugs 0.000 description 2
- 229960001671 azapropazone Drugs 0.000 description 2
- WOIIIUDZSOLAIW-NSHDSACASA-N azapropazone Chemical compound C1=C(C)C=C2N3C(=O)[C@H](CC=C)C(=O)N3C(N(C)C)=NC2=C1 WOIIIUDZSOLAIW-NSHDSACASA-N 0.000 description 2
- 229960004574 azelastine Drugs 0.000 description 2
- HGQULGDOROIPJN-UHFFFAOYSA-N azetidin-1-ium;chloride Chemical compound Cl.C1CNC1 HGQULGDOROIPJN-UHFFFAOYSA-N 0.000 description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229950000210 beclometasone dipropionate Drugs 0.000 description 2
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 2
- 229960002529 benzbromarone Drugs 0.000 description 2
- WHQCHUCQKNIQEC-UHFFFAOYSA-N benzbromarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(Br)=C(O)C(Br)=C1 WHQCHUCQKNIQEC-UHFFFAOYSA-N 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 2
- 229920002988 biodegradable polymer Polymers 0.000 description 2
- 239000004621 biodegradable polymer Substances 0.000 description 2
- 238000001574 biopsy Methods 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 206010006451 bronchitis Diseases 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 102100029170 cAMP-specific 3',5'-cyclic phosphodiesterase 4D Human genes 0.000 description 2
- 235000001465 calcium Nutrition 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000000480 calcium channel blocker Substances 0.000 description 2
- 235000017663 capsaicin Nutrition 0.000 description 2
- 229960002504 capsaicin Drugs 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000002327 cardiovascular agent Substances 0.000 description 2
- 229940125692 cardiovascular agent Drugs 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 229960003115 certolizumab pegol Drugs 0.000 description 2
- 229960001803 cetirizine Drugs 0.000 description 2
- 229960003291 chlorphenamine Drugs 0.000 description 2
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 2
- 229960003728 ciclesonide Drugs 0.000 description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
- 229960004316 cisplatin Drugs 0.000 description 2
- 229960001338 colchicine Drugs 0.000 description 2
- 229960002424 collagenase Drugs 0.000 description 2
- 108700004333 collagenase 1 Proteins 0.000 description 2
- 208000010247 contact dermatitis Diseases 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000003246 corticosteroid Substances 0.000 description 2
- 229960001334 corticosteroids Drugs 0.000 description 2
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 2
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 2
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 2
- 229960001271 desloratadine Drugs 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
- 229940043264 dodecyl sulfate Drugs 0.000 description 2
- 229960003530 donepezil Drugs 0.000 description 2
- 229940052760 dopamine agonists Drugs 0.000 description 2
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 2
- 239000000221 dopamine uptake inhibitor Substances 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 229950004203 droloxifene Drugs 0.000 description 2
- 239000003602 elastase inhibitor Substances 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000002702 enteric coating Substances 0.000 description 2
- 238000009505 enteric coating Methods 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 229960001433 erlotinib Drugs 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- SBVYURPQULDJTI-UHFFFAOYSA-N ethyl n-[amino-[4-[[3-[[4-[2-(4-hydroxyphenyl)propan-2-yl]phenoxy]methyl]phenyl]methoxy]phenyl]methylidene]carbamate Chemical compound C1=CC(C(=N)NC(=O)OCC)=CC=C1OCC1=CC=CC(COC=2C=CC(=CC=2)C(C)(C)C=2C=CC(O)=CC=2)=C1 SBVYURPQULDJTI-UHFFFAOYSA-N 0.000 description 2
- 229960000745 ethylnorepinephrine hydrochloride Drugs 0.000 description 2
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 2
- 229960005420 etoposide Drugs 0.000 description 2
- 239000003889 eye drop Substances 0.000 description 2
- 229940012356 eye drops Drugs 0.000 description 2
- 229960004396 famciclovir Drugs 0.000 description 2
- GGXKWVWZWMLJEH-UHFFFAOYSA-N famcyclovir Chemical compound N1=C(N)N=C2N(CCC(COC(=O)C)COC(C)=O)C=NC2=C1 GGXKWVWZWMLJEH-UHFFFAOYSA-N 0.000 description 2
- 229960001419 fenoprofen Drugs 0.000 description 2
- 229960003592 fexofenadine Drugs 0.000 description 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 2
- 229940125753 fibrate Drugs 0.000 description 2
- 229940126864 fibroblast growth factor Drugs 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 229960002390 flurbiprofen Drugs 0.000 description 2
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 2
- 229960000289 fluticasone propionate Drugs 0.000 description 2
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 229960002870 gabapentin Drugs 0.000 description 2
- 230000002178 gastroprotective effect Effects 0.000 description 2
- 229960002584 gefitinib Drugs 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000001415 gene therapy Methods 0.000 description 2
- 238000010914 gene-directed enzyme pro-drug therapy Methods 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 230000002068 genetic effect Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 239000003102 growth factor Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- 125000004475 heteroaralkyl group Chemical group 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 description 2
- 229960004171 hydroxychloroquine Drugs 0.000 description 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 2
- 229960001680 ibuprofen Drugs 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000007972 injectable composition Substances 0.000 description 2
- 229940102223 injectable solution Drugs 0.000 description 2
- 229940102213 injectable suspension Drugs 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229960001361 ipratropium bromide Drugs 0.000 description 2
- KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 125000005438 isoindazolyl group Chemical group 0.000 description 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 229960001317 isoprenaline Drugs 0.000 description 2
- 230000005445 isotope effect Effects 0.000 description 2
- 229960000681 leflunomide Drugs 0.000 description 2
- GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 description 2
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 description 2
- 239000008297 liquid dosage form Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229960003088 loratadine Drugs 0.000 description 2
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 229960002373 loxoprofen Drugs 0.000 description 2
- BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical compound O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229960003464 mefenamic acid Drugs 0.000 description 2
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 2
- 229960001929 meloxicam Drugs 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 229960001952 metrifonate Drugs 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229960002744 mometasone furoate Drugs 0.000 description 2
- WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 description 2
- 229960005127 montelukast Drugs 0.000 description 2
- XHOADYKJSBCVBJ-UHFFFAOYSA-N n,n-diethylpyrrolidin-3-amine Chemical compound CCN(CC)C1CCNC1 XHOADYKJSBCVBJ-UHFFFAOYSA-N 0.000 description 2
- RVXKHAITGKBBAC-SFHVURJKSA-N n-[(1s)-2-cyclohexyl-1-pyridin-2-ylethyl]-5-methyl-1,3-benzoxazol-2-amine Chemical compound C([C@H](NC=1OC2=CC=C(C=C2N=1)C)C=1N=CC=CC=1)C1CCCCC1 RVXKHAITGKBBAC-SFHVURJKSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- OHLXXFUDMGUKCG-UHFFFAOYSA-N n-methylpyrrolidin-1-amine Chemical compound CNN1CCCC1 OHLXXFUDMGUKCG-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229960004760 naphazoline hydrochloride Drugs 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 239000007922 nasal spray Substances 0.000 description 2
- 210000000653 nervous system Anatomy 0.000 description 2
- 230000003959 neuroinflammation Effects 0.000 description 2
- 201000001119 neuropathy Diseases 0.000 description 2
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- 231100000344 non-irritating Toxicity 0.000 description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 229950010666 ontazolast Drugs 0.000 description 2
- 239000003605 opacifier Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229960001609 oxitropium bromide Drugs 0.000 description 2
- LCELQERNWLBPSY-KHSTUMNDSA-M oxitropium bromide Chemical compound [Br-].C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)CC)=CC=CC=C1 LCELQERNWLBPSY-KHSTUMNDSA-M 0.000 description 2
- 229960005162 oxymetazoline hydrochloride Drugs 0.000 description 2
- BEEDODBODQVSIM-UHFFFAOYSA-N oxymetazoline hydrochloride Chemical compound Cl.CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC1=NCCN1 BEEDODBODQVSIM-UHFFFAOYSA-N 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 229960001639 penicillamine Drugs 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229940066842 petrolatum Drugs 0.000 description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 229960001802 phenylephrine Drugs 0.000 description 2
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 2
- 208000024335 physical disease Diseases 0.000 description 2
- 229960002702 piroxicam Drugs 0.000 description 2
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 2
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 description 2
- 229960005205 prednisolone Drugs 0.000 description 2
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 2
- 229960004618 prednisone Drugs 0.000 description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
- 229960001233 pregabalin Drugs 0.000 description 2
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229960003081 probenecid Drugs 0.000 description 2
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229960003910 promethazine Drugs 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- 229960000786 propylhexedrine Drugs 0.000 description 2
- JCRIVQIOJSSCQD-UHFFFAOYSA-N propylhexedrine Chemical compound CNC(C)CC1CCCCC1 JCRIVQIOJSSCQD-UHFFFAOYSA-N 0.000 description 2
- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 229960003908 pseudoephedrine Drugs 0.000 description 2
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- UAFUIWDKLIXSAZ-UHFFFAOYSA-N pyrrolidin-1-ium dichloride Chemical compound Cl.N1CCCC1.N1CCCC1.Cl UAFUIWDKLIXSAZ-UHFFFAOYSA-N 0.000 description 2
- NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 2
- QOTUIIJRVXKSJU-UHFFFAOYSA-N pyrrolidin-3-ylmethanol Chemical compound OCC1CCNC1 QOTUIIJRVXKSJU-UHFFFAOYSA-N 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 2
- RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 description 2
- 229960000245 rasagiline Drugs 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 210000000664 rectum Anatomy 0.000 description 2
- 208000023504 respiratory system disease Diseases 0.000 description 2
- WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 210000003491 skin Anatomy 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 108091007196 stromelysin Proteins 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 229960000894 sulindac Drugs 0.000 description 2
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 108060008037 tachykinin Proteins 0.000 description 2
- 229960001685 tacrine Drugs 0.000 description 2
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 2
- 229950011332 talnetant Drugs 0.000 description 2
- 229940000238 tasmar Drugs 0.000 description 2
- 229940063683 taxotere Drugs 0.000 description 2
- 229950004351 telenzepine Drugs 0.000 description 2
- 229960002871 tenoxicam Drugs 0.000 description 2
- WZWYJBNHTWCXIM-UHFFFAOYSA-N tenoxicam Chemical compound O=C1C=2SC=CC=2S(=O)(=O)N(C)C1=C(O)NC1=CC=CC=N1 WZWYJBNHTWCXIM-UHFFFAOYSA-N 0.000 description 2
- XYKWNRUXCOIMFZ-UHFFFAOYSA-N tepoxalin Chemical compound C1=CC(OC)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(CCC(=O)N(C)O)=N1 XYKWNRUXCOIMFZ-UHFFFAOYSA-N 0.000 description 2
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 2
- QHWRELFCMUTGRQ-UHFFFAOYSA-N tert-butyl 4-[6-chloro-5-[(4,4-difluorocyclohexyl)methylcarbamoyl]quinolin-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCC(=CC1)C1=NC2=CC=C(C(=C2C=C1)C(NCC1CCC(CC1)(F)F)=O)Cl QHWRELFCMUTGRQ-UHFFFAOYSA-N 0.000 description 2
- HAOYADMXLLCLFN-UHFFFAOYSA-N tert-butyl 4-[6-chloro-5-[(4,4-difluorocyclohexyl)methylcarbamoyl]quinolin-2-yl]piperidine-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)C1=NC2=CC=C(C(=C2C=C1)C(NCC1CCC(CC1)(F)F)=O)Cl HAOYADMXLLCLFN-UHFFFAOYSA-N 0.000 description 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 2
- 229940021790 tetrahydrozoline hydrochloride Drugs 0.000 description 2
- BJORNXNYWNIWEY-UHFFFAOYSA-N tetrahydrozoline hydrochloride Chemical compound Cl.N1CCN=C1C1C2=CC=CC=C2CCC1 BJORNXNYWNIWEY-UHFFFAOYSA-N 0.000 description 2
- 229960000278 theophylline Drugs 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 229960000257 tiotropium bromide Drugs 0.000 description 2
- MIQPIUSUKVNLNT-UHFFFAOYSA-N tolcapone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 MIQPIUSUKVNLNT-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 230000014616 translation Effects 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- 229960002117 triamcinolone acetonide Drugs 0.000 description 2
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 2
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 2
- 206010044652 trigeminal neuralgia Diseases 0.000 description 2
- 229910052722 tritium Inorganic materials 0.000 description 2
- 239000002750 tryptase inhibitor Substances 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 102000003298 tumor necrosis factor receptor Human genes 0.000 description 2
- 239000005526 vasoconstrictor agent Substances 0.000 description 2
- 229960003048 vinblastine Drugs 0.000 description 2
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 2
- 229960004528 vincristine Drugs 0.000 description 2
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 2
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 2
- 239000003064 xanthine oxidase inhibitor Substances 0.000 description 2
- 229960001095 xylometazoline hydrochloride Drugs 0.000 description 2
- 229960004764 zafirlukast Drugs 0.000 description 2
- 229960002555 zidovudine Drugs 0.000 description 2
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 2
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- DCTWOTGISQSTGL-LWOQYNTDSA-N (1R)-1-pyrrolidin-3-ylethanol Chemical compound N1CC(CC1)[C@@H](C)O DCTWOTGISQSTGL-LWOQYNTDSA-N 0.000 description 1
- DCTWOTGISQSTGL-ZBHICJROSA-N (1S)-1-pyrrolidin-3-ylethanol Chemical compound N1CC(CC1)[C@H](C)O DCTWOTGISQSTGL-ZBHICJROSA-N 0.000 description 1
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical class CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 description 1
- SVTFHAMUELUZFY-YFKPBYRVSA-N (2s)-piperidine-1,2-dicarboxamide Chemical compound NC(=O)[C@@H]1CCCCN1C(N)=O SVTFHAMUELUZFY-YFKPBYRVSA-N 0.000 description 1
- LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 description 1
- NGZYRKGJWYJGRS-RXMQYKEDSA-N (3r)-n-methylpyrrolidin-3-amine Chemical compound CN[C@@H]1CCNC1 NGZYRKGJWYJGRS-RXMQYKEDSA-N 0.000 description 1
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 1
- NGZYRKGJWYJGRS-YFKPBYRVSA-N (3s)-n-methylpyrrolidin-3-amine Chemical compound CN[C@H]1CCNC1 NGZYRKGJWYJGRS-YFKPBYRVSA-N 0.000 description 1
- SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 description 1
- QUPFKBITVLIQNA-KPKJPENVSA-N (5e)-2-sulfanylidene-5-[[5-[3-(trifluoromethyl)phenyl]furan-2-yl]methylidene]-1,3-thiazolidin-4-one Chemical compound FC(F)(F)C1=CC=CC(C=2OC(\C=C\3C(NC(=S)S/3)=O)=CC=2)=C1 QUPFKBITVLIQNA-KPKJPENVSA-N 0.000 description 1
- HMLGSIZOMSVISS-ONJSNURVSA-N (7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2,2-dimethylpropanoyloxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@@H]1C(N2C(=C(C=C)CSC21)C(O)=O)=O)C(=O)\C(=N/OCOC(=O)C(C)(C)C)C1=CSC(N)=N1 HMLGSIZOMSVISS-ONJSNURVSA-N 0.000 description 1
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 description 1
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 1
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 1
- NDAUXUAQIAJITI-LBPRGKRZSA-N (R)-salbutamol Chemical compound CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-LBPRGKRZSA-N 0.000 description 1
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VWIGHVNBZXTEFC-UHFFFAOYSA-N 1,2-difluoropyrrolidine Chemical compound FC1CCCN1F VWIGHVNBZXTEFC-UHFFFAOYSA-N 0.000 description 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 description 1
- DKMFBWQBDIGMHM-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-(4-methyl-1-piperidinyl)-1-butanone Chemical compound C1CC(C)CCN1CCCC(=O)C1=CC=C(F)C=C1 DKMFBWQBDIGMHM-UHFFFAOYSA-N 0.000 description 1
- OUYGJLYGNZMCDL-UHFFFAOYSA-N 1-(aminomethyl)-4,4-difluoro-3-methylcyclohexan-1-ol Chemical compound NCC1(CC(C(CC1)(F)F)C)O OUYGJLYGNZMCDL-UHFFFAOYSA-N 0.000 description 1
- LNDWOMYYGAOBQJ-UHFFFAOYSA-N 1-(methylamino)-3-(trifluoromethyl)cyclohexan-1-ol hydrochloride Chemical compound Cl.CNC1(O)CCCC(C1)C(F)(F)F LNDWOMYYGAOBQJ-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-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
- OLZHFFKRBCZHHT-SNVBAGLBSA-N 1-[(2r)-4-[5-(4-fluorophenoxy)furan-2-yl]but-3-yn-2-yl]-1-hydroxyurea Chemical compound O1C(C#C[C@@H](C)N(O)C(N)=O)=CC=C1OC1=CC=C(F)C=C1 OLZHFFKRBCZHHT-SNVBAGLBSA-N 0.000 description 1
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- SQMVRFXDBRYXFQ-UHFFFAOYSA-N 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2h-pyridine Chemical compound C1N(C)CCC(B2OC(C)(C)C(C)(C)O2)=C1 SQMVRFXDBRYXFQ-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- PDNHLCRMUIGNBV-UHFFFAOYSA-N 1-pyridin-2-ylethanamine Chemical compound CC(N)C1=CC=CC=N1 PDNHLCRMUIGNBV-UHFFFAOYSA-N 0.000 description 1
- YZWOOJYMNIAFFG-UHFFFAOYSA-N 1-pyrrolidin-1-ylpyrrolidine dihydrochloride Chemical compound Cl.Cl.C1CCN(C1)N1CCCC1 YZWOOJYMNIAFFG-UHFFFAOYSA-N 0.000 description 1
- DCTWOTGISQSTGL-UHFFFAOYSA-N 1-pyrrolidin-3-ylethanol Chemical compound CC(O)C1CCNC1 DCTWOTGISQSTGL-UHFFFAOYSA-N 0.000 description 1
- ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
- 125000005955 1H-indazolyl group Chemical group 0.000 description 1
- QEYQSYAGLRIYBE-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1,2-benzodiazepine Chemical class C1CCNNC2=CC=CC=C21 QEYQSYAGLRIYBE-UHFFFAOYSA-N 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- LPDFGLZUUCLXGM-UHFFFAOYSA-N 2,6-dichloroquinoline Chemical compound N1=C(Cl)C=CC2=CC(Cl)=CC=C21 LPDFGLZUUCLXGM-UHFFFAOYSA-N 0.000 description 1
- UCLMFWLVRUXGHD-UHFFFAOYSA-N 2,6-dichloroquinoline-5-carboxylic acid Chemical compound OC(=O)c1c(Cl)ccc2nc(Cl)ccc12.OC(=O)c1c(Cl)ccc2nc(Cl)ccc12 UCLMFWLVRUXGHD-UHFFFAOYSA-N 0.000 description 1
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 1
- JFTZVYKESKQING-UHFFFAOYSA-N 2-(cyclopenten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CCCC1 JFTZVYKESKQING-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QVNZBDLTUKCPGJ-UHFFFAOYSA-N 2-[3-amino-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-2-oxopyrrolidin-1-yl]-n-hydroxy-4-methylpentanamide Chemical compound O=C1N(C(CC(C)C)C(=O)NO)CCC1(N)C(C=C1)=CC=C1OCC1=CC(C)=NC2=CC=CC=C12 QVNZBDLTUKCPGJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- WAVYAFBQOXCGSZ-UHFFFAOYSA-N 2-fluoropyrimidine Chemical compound FC1=NC=CC=N1 WAVYAFBQOXCGSZ-UHFFFAOYSA-N 0.000 description 1
- VHBSECWYEFJRNV-UHFFFAOYSA-N 2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1O.OC(=O)C1=CC=CC=C1O VHBSECWYEFJRNV-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- NKRLLPCWCPIQPL-UHFFFAOYSA-N 2-pyrrolidin-3-ylethanol Chemical compound OCCC1CCNC1 NKRLLPCWCPIQPL-UHFFFAOYSA-N 0.000 description 1
- CUZBTJHHZNGHGR-UHFFFAOYSA-N 3,3-difluoro-N-methylcyclohexan-1-amine hydrochloride Chemical compound Cl.CNC1CCCC(F)(F)C1 CUZBTJHHZNGHGR-UHFFFAOYSA-N 0.000 description 1
- QUHVRXKSQHIZNV-UHFFFAOYSA-N 3,3-difluoroazetidine Chemical compound FC1(F)CNC1 QUHVRXKSQHIZNV-UHFFFAOYSA-N 0.000 description 1
- CDBAEFXTCRKJPZ-UHFFFAOYSA-N 3,3-difluoroazetidine;hydron;chloride Chemical compound Cl.FC1(F)CNC1 CDBAEFXTCRKJPZ-UHFFFAOYSA-N 0.000 description 1
- NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 1
- HDBQZGJWHMCXIL-UHFFFAOYSA-N 3,7-dihydropurine-2-thione Chemical compound SC1=NC=C2NC=NC2=N1 HDBQZGJWHMCXIL-UHFFFAOYSA-N 0.000 description 1
- KLYIIIVFEGRMJI-UHFFFAOYSA-N 3-(difluoromethyl)pyrrolidine;hydrochloride Chemical compound Cl.FC(F)C1CCNC1 KLYIIIVFEGRMJI-UHFFFAOYSA-N 0.000 description 1
- FEBOTPHFXYHVPL-UHFFFAOYSA-N 3-[1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidinyl]-1H-benzimidazol-2-one Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 FEBOTPHFXYHVPL-UHFFFAOYSA-N 0.000 description 1
- ULMFXAMQUGLVGA-LJQANCHMSA-N 3-[[2-methoxy-4-[(2-methylphenyl)sulfonylcarbamoyl]phenyl]methyl]-1-methyl-n-[(2r)-4,4,4-trifluoro-2-methylbutyl]indole-5-carboxamide Chemical compound C=1C=C(CC=2C3=CC(=CC=C3N(C)C=2)C(=O)NC[C@H](C)CC(F)(F)F)C(OC)=CC=1C(=O)NS(=O)(=O)C1=CC=CC=C1C ULMFXAMQUGLVGA-LJQANCHMSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
- XJCNATSGGOEQKO-UHFFFAOYSA-N 3-cyclopropyl-1-(methylamino)cyclohexan-1-ol hydrochloride Chemical compound Cl.CNC1(O)CCCC(C1)C1CC1 XJCNATSGGOEQKO-UHFFFAOYSA-N 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- JDFDHBSESGTDAL-UHFFFAOYSA-N 3-methoxypropan-1-ol Chemical compound COCCCO JDFDHBSESGTDAL-UHFFFAOYSA-N 0.000 description 1
- ADCVWDDVMLCLMH-UHFFFAOYSA-N 3-methyl-1-(methylamino)cyclohexan-1-ol Chemical compound OC1(CC(CCC1)C)NC ADCVWDDVMLCLMH-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
- PMXMIIMHBWHSKN-UHFFFAOYSA-N 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCC(O)C4=NC=3C)=NOC2=C1 PMXMIIMHBWHSKN-UHFFFAOYSA-N 0.000 description 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
- NRELFSVKUAIWGY-UHFFFAOYSA-N 4,4-difluoro-1-(methylamino)cyclohexan-1-ol hydrochloride Chemical compound Cl.CNC1(O)CCC(F)(F)CC1 NRELFSVKUAIWGY-UHFFFAOYSA-N 0.000 description 1
- RRXLFPYSNXCKBR-UHFFFAOYSA-N 4,4-difluoro-3-methyl-1-(methylamino)cyclohexan-1-ol hydrochloride Chemical compound Cl.CNC1(O)CCC(F)(F)C(C)C1 RRXLFPYSNXCKBR-UHFFFAOYSA-N 0.000 description 1
- TYNLGDBUJLVSMA-UHFFFAOYSA-N 4,5-diacetyloxy-9,10-dioxo-2-anthracenecarboxylic acid Chemical compound O=C1C2=CC(C(O)=O)=CC(OC(C)=O)=C2C(=O)C2=C1C=CC=C2OC(=O)C TYNLGDBUJLVSMA-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- SGOOQMRIPALTEL-UHFFFAOYSA-N 4-hydroxy-N,1-dimethyl-2-oxo-N-phenyl-3-quinolinecarboxamide Chemical group OC=1C2=CC=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC=CC=C1 SGOOQMRIPALTEL-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- LSLYOANBFKQKPT-DIFFPNOSSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]benzene-1,3-diol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(O)C=C(O)C=1)C1=CC=C(O)C=C1 LSLYOANBFKQKPT-DIFFPNOSSA-N 0.000 description 1
- UXNOTUIKWHKAFU-UHFFFAOYSA-N 6-chloro-2-(1,2,3,6-tetrahydropyridin-4-yl)quinoline-5-carboxylic acid Chemical compound ClC1=C(C=2C=CC(=NC=2C=C1)C=1CCNCC=1)C(=O)O UXNOTUIKWHKAFU-UHFFFAOYSA-N 0.000 description 1
- KBPLZZUCEILJRX-UHFFFAOYSA-N 6-chloro-2-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)quinoline-5-carboxylic acid Chemical compound CN1CCC(=CC1)C1=NC2=CC=C(Cl)C(C(O)=O)=C2C=C1 KBPLZZUCEILJRX-UHFFFAOYSA-N 0.000 description 1
- UOSDYMSGPMHIGS-UHFFFAOYSA-N 6-chloro-2-(1-propan-2-yl-3,6-dihydro-2H-pyridin-4-yl)quinoline-5-carboxylic acid Chemical compound CC(C)N1CCC(=CC1)c1ccc2c(C(O)=O)c(Cl)ccc2n1 UOSDYMSGPMHIGS-UHFFFAOYSA-N 0.000 description 1
- MPBNLSLKBHPNFA-UHFFFAOYSA-N 6-chloro-2-(3,3-difluoroazetidin-1-yl)quinoline-5-carboxylic acid Chemical compound ClC1=C(C=2C=CC(=NC=2C=C1)N1CC(C1)(F)F)C(=O)O MPBNLSLKBHPNFA-UHFFFAOYSA-N 0.000 description 1
- VIZGGGOYILTTHS-UHFFFAOYSA-N 6-chloro-2-(3-oxocyclopenten-1-yl)quinoline-5-carboxylic acid Chemical compound ClC1=C(C=2C=CC(=NC=2C=C1)C1=CC(CC1)=O)C(=O)O VIZGGGOYILTTHS-UHFFFAOYSA-N 0.000 description 1
- PKNVLCJNNMHDFX-UHFFFAOYSA-N 6-chloro-2-(cyclohexen-1-yl)-N-[(4,4-difluorocyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1=CCCCC1)F PKNVLCJNNMHDFX-UHFFFAOYSA-N 0.000 description 1
- KIDKIWDNMCSDIJ-IQMFZBJNSA-N 6-chloro-2-(cyclopenten-1-yl)-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1=CCCC1 KIDKIWDNMCSDIJ-IQMFZBJNSA-N 0.000 description 1
- GXHJCRXINGGWFN-UHFFFAOYSA-N 6-chloro-2-(cyclopenten-1-yl)quinoline-5-carboxylic acid Chemical compound ClC1=C(C=2C=CC(=NC=2C=C1)C1=CCCC1)C(=O)O GXHJCRXINGGWFN-UHFFFAOYSA-N 0.000 description 1
- VHJMPCGVUPMYFF-IOXSGPKDSA-N 6-chloro-2-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]-N-[[1-hydroxy-3-(trifluoromethyl)cyclohexyl]methyl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C(F)(F)F)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)N(C)C VHJMPCGVUPMYFF-IOXSGPKDSA-N 0.000 description 1
- GHHFULZHVCJCKL-YZGUTLMUSA-N 6-chloro-2-[(3R)-3-fluoropyrrolidin-1-yl]-N-[[1-hydroxy-3-(trifluoromethyl)cyclohexyl]methyl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C(F)(F)F)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)F GHHFULZHVCJCKL-YZGUTLMUSA-N 0.000 description 1
- VHJMPCGVUPMYFF-PMFMOCITSA-N 6-chloro-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N-[[1-hydroxy-3-(trifluoromethyl)cyclohexyl]methyl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C(F)(F)F)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)N(C)C VHJMPCGVUPMYFF-PMFMOCITSA-N 0.000 description 1
- GHHFULZHVCJCKL-GJGORFQUSA-N 6-chloro-2-[(3S)-3-fluoropyrrolidin-1-yl]-N-[[1-hydroxy-3-(trifluoromethyl)cyclohexyl]methyl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C(F)(F)F)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)F GHHFULZHVCJCKL-GJGORFQUSA-N 0.000 description 1
- DYBRAOZDZPISET-UHFFFAOYSA-N 6-chloro-2-[3-(2-hydroxyethyl)pyrrolidin-1-yl]quinoline-5-carboxylic acid Chemical compound ClC1=C(C=2C=CC(=NC=2C=C1)N1CC(CC1)CCO)C(=O)O DYBRAOZDZPISET-UHFFFAOYSA-N 0.000 description 1
- NQVNLUPHRFCBBI-UHFFFAOYSA-N 6-chloro-2-[3-(diethylamino)pyrrolidin-1-yl]-N-[(4,4-difluoro-1-hydroxy-3-methylcyclohexyl)methyl]quinoline-5-carboxamide Chemical compound FC1(C(CC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N(CC)CC)C)F NQVNLUPHRFCBBI-UHFFFAOYSA-N 0.000 description 1
- DSWCAMSVSWRCIH-MRKPZEEPSA-N 6-chloro-2-[3-(diethylamino)pyrrolidin-1-yl]-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N(CC)CC DSWCAMSVSWRCIH-MRKPZEEPSA-N 0.000 description 1
- DSWCAMSVSWRCIH-RXBAOPJQSA-N 6-chloro-2-[3-(diethylamino)pyrrolidin-1-yl]-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N(CC)CC DSWCAMSVSWRCIH-RXBAOPJQSA-N 0.000 description 1
- DXYPZGNOLQPKSH-NGQILDDCSA-N 6-chloro-2-[3-(dimethylamino)pyrrolidin-1-yl]-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N(C)C DXYPZGNOLQPKSH-NGQILDDCSA-N 0.000 description 1
- KQONAXQIHSEYGY-IQMFZBJNSA-N 6-chloro-2-cyclopentyl-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1CCCC1 KQONAXQIHSEYGY-IQMFZBJNSA-N 0.000 description 1
- KQONAXQIHSEYGY-WNSKOXEYSA-N 6-chloro-2-cyclopentyl-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]quinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1CCCC1 KQONAXQIHSEYGY-WNSKOXEYSA-N 0.000 description 1
- GZMIZTLJWWAOER-JGHKVMFLSA-N 6-chloro-N-[(3,3-difluoro-1-hydroxycyclohexyl)methyl]-2-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CC(CCC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)N(C)C)F GZMIZTLJWWAOER-JGHKVMFLSA-N 0.000 description 1
- PVHXWOIFGTVYHS-HOYUBGIKSA-N 6-chloro-N-[(3-cyclopropyl-1-hydroxycyclohexyl)methyl]-2-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C1CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)N(C)C PVHXWOIFGTVYHS-HOYUBGIKSA-N 0.000 description 1
- PVHXWOIFGTVYHS-XWJIAHPJSA-N 6-chloro-N-[(3-cyclopropyl-1-hydroxycyclohexyl)methyl]-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound OC1(CC(CCC1)C1CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)N(C)C PVHXWOIFGTVYHS-XWJIAHPJSA-N 0.000 description 1
- TUTNTVCMFVPCJZ-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxy-3-methylcyclohexyl)methyl]-2-(3-pyrrolidin-1-ylpyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound FC1(C(CC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N1CCCC1)C)F TUTNTVCMFVPCJZ-UHFFFAOYSA-N 0.000 description 1
- BUMAFNUWOOMJSA-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxy-3-methylcyclohexyl)methyl]-2-[3-(dimethylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(C(CC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N(C)C)C)F BUMAFNUWOOMJSA-UHFFFAOYSA-N 0.000 description 1
- VMCZCYNHHOPGDR-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]-2-(3-oxocyclopenten-1-yl)quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C1=CC(CC1)=O)F VMCZCYNHHOPGDR-UHFFFAOYSA-N 0.000 description 1
- ZSMWSNOOFULQSA-OAHLLOKOSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]-2-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@@H](CC1)N(C)C)F ZSMWSNOOFULQSA-OAHLLOKOSA-N 0.000 description 1
- ZSMWSNOOFULQSA-HNNXBMFYSA-N 6-chloro-N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1C[C@H](CC1)N(C)C)F ZSMWSNOOFULQSA-HNNXBMFYSA-N 0.000 description 1
- INQAZFZQTBGTOP-UHFFFAOYSA-N 6-chloro-N-[(4,4-difluorocyclohexyl)methyl]-2-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)quinoline-5-carboxamide Chemical compound FC1(CCC(CC1)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)C=1CCN(CC=1)C)F INQAZFZQTBGTOP-UHFFFAOYSA-N 0.000 description 1
- FRNCVZBYBCYMMN-MRKPZEEPSA-N 6-chloro-N-[[(1R,3R)-1-hydroxy-3-methylcyclohexyl]methyl]-2-(3-pyrrolidin-1-ylpyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound O[C@]1(C[C@@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N1CCCC1 FRNCVZBYBCYMMN-MRKPZEEPSA-N 0.000 description 1
- WYWXVRPONGIPBX-IBGZPJMESA-N 6-chloro-N-[[(1S)-3,3-difluoro-1-hydroxycyclohexyl]methyl]-2-(3,3-difluoropyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound FC1(C[C@](CCC1)(O)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)(F)F)F WYWXVRPONGIPBX-IBGZPJMESA-N 0.000 description 1
- FRNCVZBYBCYMMN-RXBAOPJQSA-N 6-chloro-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]-2-(3-pyrrolidin-1-ylpyrrolidin-1-yl)quinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)N1CCCC1 FRNCVZBYBCYMMN-RXBAOPJQSA-N 0.000 description 1
- PQBSYWYWWMMFKG-HRXGFSSHSA-N 6-chloro-N-[[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl]-2-[3-(hydroxymethyl)pyrrolidin-1-yl]quinoline-5-carboxamide Chemical compound O[C@@]1(C[C@H](CCC1)C)CNC(=O)C=1C=2C=CC(=NC=2C=CC=1Cl)N1CC(CC1)CO PQBSYWYWWMMFKG-HRXGFSSHSA-N 0.000 description 1
- 102100031126 6-phosphogluconolactonase Human genes 0.000 description 1
- 108010029731 6-phosphogluconolactonase Proteins 0.000 description 1
- IXJCHVMUTFCRBH-SDUHDBOFSA-N 7-[(1r,2s,3e,5z)-10-(4-acetyl-3-hydroxy-2-propylphenoxy)-1-hydroxy-1-[3-(trifluoromethyl)phenyl]deca-3,5-dien-2-yl]sulfanyl-4-oxochromene-2-carboxylic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCC\C=C/C=C/[C@@H]([C@H](O)C=1C=C(C=CC=1)C(F)(F)F)SC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 IXJCHVMUTFCRBH-SDUHDBOFSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 239000005541 ACE inhibitor Substances 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 208000017194 Affective disease Diseases 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 208000008811 Agoraphobia Diseases 0.000 description 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 description 1
- 229940124810 Alzheimer's drug Drugs 0.000 description 1
- 108010029748 Angiostat Proteins 0.000 description 1
- 102400000068 Angiostatin Human genes 0.000 description 1
- 108010079709 Angiostatins Proteins 0.000 description 1
- 102100033367 Appetite-regulating hormone Human genes 0.000 description 1
- 101710111255 Appetite-regulating hormone Proteins 0.000 description 1
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 description 1
- BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 description 1
- 206010003399 Arthropod bite Diseases 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- 102100022005 B-lymphocyte antigen CD20 Human genes 0.000 description 1
- 102000036365 BRCA1 Human genes 0.000 description 1
- 108700020463 BRCA1 Proteins 0.000 description 1
- 101150072950 BRCA1 gene Proteins 0.000 description 1
- 102000052609 BRCA2 Human genes 0.000 description 1
- 108700020462 BRCA2 Proteins 0.000 description 1
- 208000008035 Back Pain Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- CYGODHVAJQTCBG-UHFFFAOYSA-N Bifeprunox Chemical compound C=12OC(=O)NC2=CC=CC=1N(CC1)CCN1CC(C=1)=CC=CC=1C1=CC=CC=C1 CYGODHVAJQTCBG-UHFFFAOYSA-N 0.000 description 1
- MNIPYSSQXLZQLJ-UHFFFAOYSA-N Biofenac Chemical compound OC(=O)COC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl MNIPYSSQXLZQLJ-UHFFFAOYSA-N 0.000 description 1
- 206010069632 Bladder dysfunction Diseases 0.000 description 1
- 108010006654 Bleomycin Proteins 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 101150008921 Brca2 gene Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010068065 Burning mouth syndrome Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 102100031172 C-C chemokine receptor type 1 Human genes 0.000 description 1
- 101710149814 C-C chemokine receptor type 1 Proteins 0.000 description 1
- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 description 1
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 description 1
- 102100037853 C-C chemokine receptor type 4 Human genes 0.000 description 1
- 101710149863 C-C chemokine receptor type 4 Proteins 0.000 description 1
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 description 1
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 description 1
- 102100036301 C-C chemokine receptor type 7 Human genes 0.000 description 1
- 102100036305 C-C chemokine receptor type 8 Human genes 0.000 description 1
- 102100036166 C-X-C chemokine receptor type 1 Human genes 0.000 description 1
- 102100028989 C-X-C chemokine receptor type 2 Human genes 0.000 description 1
- 102100028990 C-X-C chemokine receptor type 3 Human genes 0.000 description 1
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 description 1
- 102100031658 C-X-C chemokine receptor type 5 Human genes 0.000 description 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 1
- BUMAFNUWOOMJSA-IOXSGPKDSA-N CC(CC(CNC(c1c(ccc(N(CC2)C[C@@H]2N(C)C)n2)c2ccc1Cl)=O)(CC1)O)C1(F)F Chemical compound CC(CC(CNC(c1c(ccc(N(CC2)C[C@@H]2N(C)C)n2)c2ccc1Cl)=O)(CC1)O)C1(F)F BUMAFNUWOOMJSA-IOXSGPKDSA-N 0.000 description 1
- CHCCBPDEADMNCI-UHFFFAOYSA-N CC(CC1)=CC1=O Chemical compound CC(CC1)=CC1=O CHCCBPDEADMNCI-UHFFFAOYSA-N 0.000 description 1
- BLZPNPLNGPYEGR-UHFFFAOYSA-N CC(CCC1)CC1(CNC(c1c(ccc(N(CC2)CC2(F)F)n2)c2ccc1Cl)=O)O Chemical compound CC(CCC1)CC1(CNC(c1c(ccc(N(CC2)CC2(F)F)n2)c2ccc1Cl)=O)O BLZPNPLNGPYEGR-UHFFFAOYSA-N 0.000 description 1
- FXRQIWHJOPKGHM-UHFFFAOYSA-N CN(C)C(CC1)CC1C(CCc1c2C(NCC(CC3)CCC3(F)F)=O)=Nc1ccc2Cl Chemical compound CN(C)C(CC1)CC1C(CCc1c2C(NCC(CC3)CCC3(F)F)=O)=Nc1ccc2Cl FXRQIWHJOPKGHM-UHFFFAOYSA-N 0.000 description 1
- QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 description 1
- 108090000835 CX3C Chemokine Receptor 1 Proteins 0.000 description 1
- 102100039196 CX3C chemokine receptor 1 Human genes 0.000 description 1
- HCXBYIHIMJUDJQ-YUMQZZPRSA-N C[C@@H](CCC1)C[C@@]1(CN)O Chemical compound C[C@@H](CCC1)C[C@@]1(CN)O HCXBYIHIMJUDJQ-YUMQZZPRSA-N 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 206010063094 Cerebral malaria Diseases 0.000 description 1
- 206010008334 Cervicobrachial syndrome Diseases 0.000 description 1
- 102000009410 Chemokine receptor Human genes 0.000 description 1
- 108050000299 Chemokine receptor Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 1
- UDKCHVLMFQVBAA-UHFFFAOYSA-M Choline salicylate Chemical compound C[N+](C)(C)CCO.OC1=CC=CC=C1C([O-])=O UDKCHVLMFQVBAA-UHFFFAOYSA-M 0.000 description 1
- VWFCHDSQECPREK-LURJTMIESA-N Cidofovir Chemical compound NC=1C=CN(C[C@@H](CO)OCP(O)(O)=O)C(=O)N=1 VWFCHDSQECPREK-LURJTMIESA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- QTGFMZNURBBYMN-UHFFFAOYSA-N Cl.FC1(C(C(CCC1)NC)O)F Chemical compound Cl.FC1(C(C(CCC1)NC)O)F QTGFMZNURBBYMN-UHFFFAOYSA-N 0.000 description 1
- 208000006561 Cluster Headache Diseases 0.000 description 1
- 102100031162 Collagen alpha-1(XVIII) chain Human genes 0.000 description 1
- HVXBOLULGPECHP-WAYWQWQTSA-N Combretastatin A4 Chemical compound C1=C(O)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-WAYWQWQTSA-N 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 208000028006 Corneal injury Diseases 0.000 description 1
- ITRJWOMZKQRYTA-RFZYENFJSA-N Cortisone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O ITRJWOMZKQRYTA-RFZYENFJSA-N 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 102000008130 Cyclic AMP-Dependent Protein Kinases Human genes 0.000 description 1
- 108010049894 Cyclic AMP-Dependent Protein Kinases Proteins 0.000 description 1
- 102000016736 Cyclin Human genes 0.000 description 1
- 108050006400 Cyclin Proteins 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 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
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 1
- 102000000311 Cytosine Deaminase Human genes 0.000 description 1
- 108010080611 Cytosine Deaminase Proteins 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- 108010092160 Dactinomycin Proteins 0.000 description 1
- VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012434 Dermatitis allergic Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 101100189582 Dictyostelium discoideum pdeD gene Proteins 0.000 description 1
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 1
- XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 108010079505 Endostatins Proteins 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- 102400001368 Epidermal growth factor Human genes 0.000 description 1
- 101800003838 Epidermal growth factor Proteins 0.000 description 1
- 206010014989 Epidermolysis bullosa Diseases 0.000 description 1
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- 108010008165 Etanercept Proteins 0.000 description 1
- 229940124226 Farnesyltransferase inhibitor Drugs 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 108090000386 Fibroblast Growth Factor 1 Proteins 0.000 description 1
- 102100031706 Fibroblast growth factor 1 Human genes 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 102000011652 Formyl peptide receptors Human genes 0.000 description 1
- 108010076288 Formyl peptide receptors Proteins 0.000 description 1
- VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 208000014540 Functional gastrointestinal disease Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 208000011688 Generalised anxiety disease Diseases 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 208000021965 Glossopharyngeal Nerve disease Diseases 0.000 description 1
- 108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical compound [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 description 1
- BLCLNMBMMGCOAS-URPVMXJPSA-N Goserelin Chemical compound C([C@@H](C(=O)N[C@H](COC(C)(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 BLCLNMBMMGCOAS-URPVMXJPSA-N 0.000 description 1
- 108010069236 Goserelin Proteins 0.000 description 1
- 108010051696 Growth Hormone Proteins 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 108090000100 Hepatocyte Growth Factor Proteins 0.000 description 1
- 102100021866 Hepatocyte growth factor Human genes 0.000 description 1
- 102000003834 Histamine H1 Receptors Human genes 0.000 description 1
- 108090000110 Histamine H1 Receptors Proteins 0.000 description 1
- 101000798902 Homo sapiens Atypical chemokine receptor 4 Proteins 0.000 description 1
- 101000897405 Homo sapiens B-lymphocyte antigen CD20 Proteins 0.000 description 1
- 101000777558 Homo sapiens C-C chemokine receptor type 10 Proteins 0.000 description 1
- 101000716068 Homo sapiens C-C chemokine receptor type 6 Proteins 0.000 description 1
- 101000716065 Homo sapiens C-C chemokine receptor type 7 Proteins 0.000 description 1
- 101000716063 Homo sapiens C-C chemokine receptor type 8 Proteins 0.000 description 1
- 101000716070 Homo sapiens C-C chemokine receptor type 9 Proteins 0.000 description 1
- 101000947174 Homo sapiens C-X-C chemokine receptor type 1 Proteins 0.000 description 1
- 101000916050 Homo sapiens C-X-C chemokine receptor type 3 Proteins 0.000 description 1
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 description 1
- 101000922405 Homo sapiens C-X-C chemokine receptor type 5 Proteins 0.000 description 1
- 101001033249 Homo sapiens Interleukin-1 beta Proteins 0.000 description 1
- 101000904173 Homo sapiens Progonadoliberin-1 Proteins 0.000 description 1
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 1
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-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
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- 108010047852 Integrin alphaVbeta3 Chemical group 0.000 description 1
- 206010049949 Intercostal neuralgia Diseases 0.000 description 1
- 102000000589 Interleukin-1 Human genes 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 108090000193 Interleukin-1 beta Proteins 0.000 description 1
- 102000003777 Interleukin-1 beta Human genes 0.000 description 1
- 102000051628 Interleukin-1 receptor antagonist Human genes 0.000 description 1
- 108700021006 Interleukin-1 receptor antagonist Proteins 0.000 description 1
- 102000000588 Interleukin-2 Human genes 0.000 description 1
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- 102000004388 Interleukin-4 Human genes 0.000 description 1
- 108090000978 Interleukin-4 Proteins 0.000 description 1
- 108010018951 Interleukin-8B Receptors Proteins 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 241000764238 Isis Species 0.000 description 1
- 108010044467 Isoenzymes Proteins 0.000 description 1
- PJAAESPGJOSQGZ-DZGBDDFRSA-N Isovelleral Chemical compound O=CC1=C[C@@H]2CC(C)(C)C[C@@H]2[C@@]2(C)C[C@]21C=O PJAAESPGJOSQGZ-DZGBDDFRSA-N 0.000 description 1
- 101150069380 JAK3 gene Proteins 0.000 description 1
- 108010055717 JNK Mitogen-Activated Protein Kinases Proteins 0.000 description 1
- 102000019145 JUN kinase activity proteins Human genes 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
- 108010092694 L-Selectin Proteins 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 102100033467 L-selectin Human genes 0.000 description 1
- 239000005551 L01XE03 - Erlotinib Substances 0.000 description 1
- YFIZRWPXUYFCSN-UHFFFAOYSA-N LY293111 Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(O)=O)C(CCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1C1=CC=C(F)C=C1 YFIZRWPXUYFCSN-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 108010000817 Leuprolide Proteins 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- 102000004086 Ligand-Gated Ion Channels Human genes 0.000 description 1
- 108090000543 Ligand-Gated Ion Channels Proteins 0.000 description 1
- 208000008930 Low Back Pain Diseases 0.000 description 1
- 229940124041 Luteinizing hormone releasing hormone (LHRH) antagonist Drugs 0.000 description 1
- 108091054455 MAP kinase family Proteins 0.000 description 1
- 102000043136 MAP kinase family Human genes 0.000 description 1
- 108700041567 MDR Genes Proteins 0.000 description 1
- 102100027998 Macrophage metalloelastase Human genes 0.000 description 1
- 101710187853 Macrophage metalloelastase Proteins 0.000 description 1
- MQHWFIOJQSCFNM-UHFFFAOYSA-L Magnesium salicylate Chemical compound [Mg+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O MQHWFIOJQSCFNM-UHFFFAOYSA-L 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 108010015302 Matrix metalloproteinase-9 Proteins 0.000 description 1
- 102100030412 Matrix metalloproteinase-9 Human genes 0.000 description 1
- SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 description 1
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- PVLJETXTTWAYEW-UHFFFAOYSA-N Mizolastine Chemical compound N=1C=CC(=O)NC=1N(C)C(CC1)CCN1C1=NC2=CC=CC=C2N1CC1=CC=C(F)C=C1 PVLJETXTTWAYEW-UHFFFAOYSA-N 0.000 description 1
- 208000002472 Morton Neuroma Diseases 0.000 description 1
- 208000020059 Morton neuralgia Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 206010028289 Muscle atrophy Diseases 0.000 description 1
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 description 1
- 206010029113 Neovascularisation Diseases 0.000 description 1
- 102100030411 Neutrophil collagenase Human genes 0.000 description 1
- 101710118230 Neutrophil collagenase Proteins 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 102000011779 Nitric Oxide Synthase Type II Human genes 0.000 description 1
- 108010076864 Nitric Oxide Synthase Type II Proteins 0.000 description 1
- 102000004459 Nitroreductase Human genes 0.000 description 1
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 1
- KVBJTKFQCHOTDP-UHFFFAOYSA-N OC(CC1)CC1c(cc1)nc(cc2)c1c(C(NCC(CC1)(CCC1(F)F)O)=O)c2Cl Chemical compound OC(CC1)CC1c(cc1)nc(cc2)c1c(C(NCC(CC1)(CCC1(F)F)O)=O)c2Cl KVBJTKFQCHOTDP-UHFFFAOYSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 206010068106 Occipital neuralgia Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 101150098694 PDE5A gene Proteins 0.000 description 1
- 238000012879 PET imaging Methods 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 206010033664 Panic attack Diseases 0.000 description 1
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 1
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 description 1
- RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 description 1
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical compound CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- 206010034912 Phobia Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- 108010039918 Polylysine Proteins 0.000 description 1
- 206010036105 Polyneuropathy Diseases 0.000 description 1
- 229920001710 Polyorthoester Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 102100024028 Progonadoliberin-1 Human genes 0.000 description 1
- ZGUGWUXLJSTTMA-UHFFFAOYSA-N Promazinum Chemical compound C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZGUGWUXLJSTTMA-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- RBQOQRRFDPXAGN-UHFFFAOYSA-N Propentofylline Chemical compound CN1C(=O)N(CCCCC(C)=O)C(=O)C2=C1N=CN2CCC RBQOQRRFDPXAGN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 108050000258 Prostaglandin D receptors Proteins 0.000 description 1
- 102100024218 Prostaglandin D2 receptor 2 Human genes 0.000 description 1
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 1
- 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 1
- 102000007327 Protamines Human genes 0.000 description 1
- 108010007568 Protamines Proteins 0.000 description 1
- 108091008611 Protein Kinase B Proteins 0.000 description 1
- 108090000315 Protein Kinase C Proteins 0.000 description 1
- 102000003923 Protein Kinase C Human genes 0.000 description 1
- 102000005765 Proto-Oncogene Proteins c-akt Human genes 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 102000000033 Purinergic Receptors Human genes 0.000 description 1
- 108010080192 Purinergic Receptors Proteins 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 1
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 description 1
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 208000008765 Sciatica Diseases 0.000 description 1
- 206010039705 Scleritis Diseases 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 229940121742 Serine/threonine kinase inhibitor Drugs 0.000 description 1
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
- 201000010001 Silicosis Diseases 0.000 description 1
- 206010040744 Sinus headache Diseases 0.000 description 1
- 208000004078 Snake Bites Diseases 0.000 description 1
- 206010041250 Social phobia Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 102100038803 Somatotropin Human genes 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 208000003589 Spider Bites Diseases 0.000 description 1
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 description 1
- 208000011962 Substance-induced mood disease Diseases 0.000 description 1
- 231100000395 Substance-induced mood disorder Toxicity 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 description 1
- 206010042674 Swelling Diseases 0.000 description 1
- 230000017274 T cell anergy Effects 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 229940126422 TRPV1 antagonist Drugs 0.000 description 1
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 description 1
- GFBKORZTTCHDGY-UWVJOHFNSA-N Thiothixene Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2\C1=C\CCN1CCN(C)CC1 GFBKORZTTCHDGY-UWVJOHFNSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 102000006601 Thymidine Kinase Human genes 0.000 description 1
- 108020004440 Thymidine kinase Proteins 0.000 description 1
- IVTVGDXNLFLDRM-HNNXBMFYSA-N Tomudex Chemical compound C=1C=C2NC(C)=NC(=O)C2=CC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)S1 IVTVGDXNLFLDRM-HNNXBMFYSA-N 0.000 description 1
- 206010044248 Toxic shock syndrome Diseases 0.000 description 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
- RZOXEODOFNEZRS-UHFFFAOYSA-N Tramazoline hydrochloride Chemical compound [Cl-].N1CCN=C1[NH2+]C1=CC=CC2=C1CCCC2 RZOXEODOFNEZRS-UHFFFAOYSA-N 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 102000004887 Transforming Growth Factor beta Human genes 0.000 description 1
- 108090001012 Transforming Growth Factor beta Proteins 0.000 description 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 102000004504 Urokinase Plasminogen Activator Receptors Human genes 0.000 description 1
- 108010042352 Urokinase Plasminogen Activator Receptors Proteins 0.000 description 1
- HDOVUKNUBWVHOX-QMMMGPOBSA-N Valacyclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 HDOVUKNUBWVHOX-QMMMGPOBSA-N 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 206010046996 Varicose vein Diseases 0.000 description 1
- 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 1
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 1
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 1
- 229940122803 Vinca alkaloid Drugs 0.000 description 1
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- QOTUIIJRVXKSJU-RXMQYKEDSA-N [(3r)-pyrrolidin-3-yl]methanol Chemical compound OC[C@@H]1CCNC1 QOTUIIJRVXKSJU-RXMQYKEDSA-N 0.000 description 1
- QOTUIIJRVXKSJU-YFKPBYRVSA-N [(3s)-pyrrolidin-3-yl]methanol Chemical compound OC[C@H]1CCNC1 QOTUIIJRVXKSJU-YFKPBYRVSA-N 0.000 description 1
- ZVCFRJGVHLVXJW-UHFFFAOYSA-N [1,3]oxazolo[4,5-b]pyridine [1,3]thiazolo[4,5-b]pyridine Chemical compound S1C=NC2=C1C=CC=N2.O2C=NC1=C2C=CC=N1 ZVCFRJGVHLVXJW-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 229960004420 aceclofenac Drugs 0.000 description 1
- 229960004892 acemetacin Drugs 0.000 description 1
- FSQKKOOTNAMONP-UHFFFAOYSA-N acemetacin Chemical compound CC1=C(CC(=O)OCC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 FSQKKOOTNAMONP-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229960002964 adalimumab Drugs 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000003470 adrenal cortex hormone Substances 0.000 description 1
- 239000000533 adrenergic alpha-1 receptor agonist Substances 0.000 description 1
- 239000000384 adrenergic alpha-2 receptor agonist Substances 0.000 description 1
- 239000000808 adrenergic beta-agonist Substances 0.000 description 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 229960002478 aldosterone Drugs 0.000 description 1
- 229940062527 alendronate Drugs 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 208000030961 allergic reaction Diseases 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 229960003805 amantadine Drugs 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 229960003036 amisulpride Drugs 0.000 description 1
- NTJOBXMMWNYJFB-UHFFFAOYSA-N amisulpride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC NTJOBXMMWNYJFB-UHFFFAOYSA-N 0.000 description 1
- 229960001220 amsacrine Drugs 0.000 description 1
- XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 229960004238 anakinra Drugs 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 229960002932 anastrozole Drugs 0.000 description 1
- YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 1
- 239000004037 angiogenesis inhibitor Substances 0.000 description 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229940045799 anthracyclines and related substance Drugs 0.000 description 1
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002280 anti-androgenic effect Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 229940046836 anti-estrogen Drugs 0.000 description 1
- 230000001833 anti-estrogenic effect Effects 0.000 description 1
- 230000003432 anti-folate effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000003302 anti-idiotype Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003262 anti-osteoporosis Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000002137 anti-vascular effect Effects 0.000 description 1
- 239000000051 antiandrogen Substances 0.000 description 1
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 229940127074 antifolate Drugs 0.000 description 1
- 239000002255 antigout agent Substances 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
- 239000003972 antineoplastic antibiotic Substances 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 208000007474 aortic aneurysm Diseases 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 229960004372 aripiprazole Drugs 0.000 description 1
- 239000003886 aromatase inhibitor Substances 0.000 description 1
- 229940046844 aromatase inhibitors Drugs 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- FZCSTZYAHCUGEM-UHFFFAOYSA-N aspergillomarasmine B Natural products OC(=O)CNC(C(O)=O)CNC(C(O)=O)CC(O)=O FZCSTZYAHCUGEM-UHFFFAOYSA-N 0.000 description 1
- 239000012131 assay buffer Substances 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
- 229960002170 azathioprine Drugs 0.000 description 1
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229960004168 balsalazide Drugs 0.000 description 1
- IPOKCKJONYRRHP-FMQUCBEESA-N balsalazide Chemical compound C1=CC(C(=O)NCCC(=O)O)=CC=C1\N=N\C1=CC=C(O)C(C(O)=O)=C1 IPOKCKJONYRRHP-FMQUCBEESA-N 0.000 description 1
- 229960003060 bambuterol Drugs 0.000 description 1
- ANZXOIAKUNOVQU-UHFFFAOYSA-N bambuterol Chemical compound CN(C)C(=O)OC1=CC(OC(=O)N(C)C)=CC(C(O)CNC(C)(C)C)=C1 ANZXOIAKUNOVQU-UHFFFAOYSA-N 0.000 description 1
- 229940092705 beclomethasone Drugs 0.000 description 1
- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960002507 benperidol Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- 229960002537 betamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
- 229960000397 bevacizumab Drugs 0.000 description 1
- 229960000997 bicalutamide Drugs 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 229950009087 bifeprunox Drugs 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 208000028683 bipolar I disease Diseases 0.000 description 1
- 208000022257 bipolar II disease Diseases 0.000 description 1
- 229960000585 bitolterol mesylate Drugs 0.000 description 1
- HODFCFXCOMKRCG-UHFFFAOYSA-N bitolterol mesylate Chemical compound CS([O-])(=O)=O.C1=CC(C)=CC=C1C(=O)OC1=CC=C(C(O)C[NH2+]C(C)(C)C)C=C1OC(=O)C1=CC=C(C)C=C1 HODFCFXCOMKRCG-UHFFFAOYSA-N 0.000 description 1
- 229960001561 bleomycin Drugs 0.000 description 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 230000004097 bone metabolism Effects 0.000 description 1
- 208000019664 bone resorption disease Diseases 0.000 description 1
- BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical compound B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 description 1
- 201000007637 bowel dysfunction Diseases 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 229960003655 bromfenac Drugs 0.000 description 1
- ZBPLOVFIXSTCRZ-UHFFFAOYSA-N bromfenac Chemical compound NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1 ZBPLOVFIXSTCRZ-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 1
- 229960001058 bupropion Drugs 0.000 description 1
- 229960002092 busulfan Drugs 0.000 description 1
- 102100029175 cGMP-specific 3',5'-cyclic phosphodiesterase Human genes 0.000 description 1
- LWQQLNNNIPYSNX-UROSTWAQSA-N calcipotriol Chemical compound C1([C@H](O)/C=C/[C@@H](C)[C@@H]2[C@]3(CCCC(/[C@@H]3CC2)=C\C=C\2C([C@@H](O)C[C@H](O)C/2)=C)C)CC1 LWQQLNNNIPYSNX-UROSTWAQSA-N 0.000 description 1
- 229960002882 calcipotriol Drugs 0.000 description 1
- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
- 229940127093 camptothecin Drugs 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 229950002826 canertinib Drugs 0.000 description 1
- 239000003554 cannabinoid 1 receptor agonist Substances 0.000 description 1
- 229960000623 carbamazepine Drugs 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000004623 carbolinyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 229960003184 carprofen Drugs 0.000 description 1
- IVUMCTKHWDRRMH-UHFFFAOYSA-N carprofen Chemical compound C1=CC(Cl)=C[C]2C3=CC=C(C(C(O)=O)C)C=C3N=C21 IVUMCTKHWDRRMH-UHFFFAOYSA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 230000004700 cellular uptake Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 229940081733 cetearyl alcohol Drugs 0.000 description 1
- 229960005395 cetuximab Drugs 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 230000035606 childbirth Effects 0.000 description 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
- 229960004630 chlorambucil Drugs 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960002688 choline salicylate Drugs 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 229960000724 cidofovir Drugs 0.000 description 1
- 229950010851 cimicoxib Drugs 0.000 description 1
- KYXDNECMRLFQMZ-UHFFFAOYSA-N cimicoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=C(Cl)N=CN1C1=CC=C(S(N)(=O)=O)C=C1 KYXDNECMRLFQMZ-UHFFFAOYSA-N 0.000 description 1
- NJMYODHXAKYRHW-DVZOWYKESA-N cis-flupenthixol Chemical compound C1CN(CCO)CCN1CC\C=C\1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C2/1 NJMYODHXAKYRHW-DVZOWYKESA-N 0.000 description 1
- 229960001653 citalopram Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229960001117 clenbuterol Drugs 0.000 description 1
- STJMRWALKKWQGH-UHFFFAOYSA-N clenbuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 STJMRWALKKWQGH-UHFFFAOYSA-N 0.000 description 1
- 229960004170 clozapine Drugs 0.000 description 1
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 1
- 208000018912 cluster headache syndrome Diseases 0.000 description 1
- 238000002288 cocrystallisation Methods 0.000 description 1
- 230000037410 cognitive enhancement Effects 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 229960005537 combretastatin A-4 Drugs 0.000 description 1
- HVXBOLULGPECHP-UHFFFAOYSA-N combretastatin A4 Natural products C1=C(O)C(OC)=CC=C1C=CC1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-UHFFFAOYSA-N 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 229960003290 cortisone acetate Drugs 0.000 description 1
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 208000012790 cranial neuralgia Diseases 0.000 description 1
- 229960000265 cromoglicic acid Drugs 0.000 description 1
- 230000009260 cross reactivity Effects 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- XZWQKJXJNKYMAP-UHFFFAOYSA-N cyclohexen-1-ylboronic acid Chemical compound OB(O)C1=CCCCC1 XZWQKJXJNKYMAP-UHFFFAOYSA-N 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
- 239000003260 cyclooxygenase 1 inhibitor Substances 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 229960003843 cyproterone Drugs 0.000 description 1
- DUSHUSLJJMDGTE-ZJPMUUANSA-N cyproterone Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DUSHUSLJJMDGTE-ZJPMUUANSA-N 0.000 description 1
- 230000010250 cytokine signaling pathway Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- 229960000640 dactinomycin Drugs 0.000 description 1
- XUDOZULIAWNMIU-UHFFFAOYSA-N delta-hexenoic acid Chemical compound OC(=O)CCCC=C XUDOZULIAWNMIU-UHFFFAOYSA-N 0.000 description 1
- 210000004443 dendritic cell Anatomy 0.000 description 1
- 239000011903 deuterated solvents Substances 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 1
- 229960004590 diacerein Drugs 0.000 description 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 229960002656 didanosine Drugs 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 229960000616 diflunisal Drugs 0.000 description 1
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 229940120889 dipyrone Drugs 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 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
- 238000009826 distribution Methods 0.000 description 1
- 229960002311 dithranol Drugs 0.000 description 1
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 1
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 229960003722 doxycycline Drugs 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 229960000394 droperidol Drugs 0.000 description 1
- RMEDXOLNCUSCGS-UHFFFAOYSA-N droperidol Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CC=C(N2C(NC3=CC=CC=C32)=O)CC1 RMEDXOLNCUSCGS-UHFFFAOYSA-N 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 229960002866 duloxetine Drugs 0.000 description 1
- 206010013990 dysuria Diseases 0.000 description 1
- 239000003221 ear drop Substances 0.000 description 1
- 229940047652 ear drops Drugs 0.000 description 1
- 229960003804 efavirenz Drugs 0.000 description 1
- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000008387 emulsifying waxe Substances 0.000 description 1
- 239000006274 endogenous ligand Substances 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940095399 enema Drugs 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 229940116977 epidermal growth factor Drugs 0.000 description 1
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 1
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 1
- 229960001904 epirubicin Drugs 0.000 description 1
- WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 description 1
- 229960004341 escitalopram Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000328 estrogen antagonist Substances 0.000 description 1
- 102000015694 estrogen receptors Human genes 0.000 description 1
- 108010038795 estrogen receptors Proteins 0.000 description 1
- 229950001288 etalocib Drugs 0.000 description 1
- 229960000403 etanercept Drugs 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
- XIWBSOUNZWSFKU-UHFFFAOYSA-N ethyl piperidine-3-carboxylate Chemical compound CCOC(=O)C1CCCNC1 XIWBSOUNZWSFKU-UHFFFAOYSA-N 0.000 description 1
- YJJCBPAEWVURMJ-UHFFFAOYSA-N ethyl propanoate;hydrochloride Chemical compound Cl.CCOC(=O)CC YJJCBPAEWVURMJ-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 229960005293 etodolac Drugs 0.000 description 1
- XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-UHFFFAOYSA-N 0.000 description 1
- 230000005713 exacerbation Effects 0.000 description 1
- 229960000255 exemestane Drugs 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 229960001395 fenbufen Drugs 0.000 description 1
- ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 description 1
- 229960001022 fenoterol Drugs 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 1
- 229960004039 finasteride Drugs 0.000 description 1
- SYWHXTATXSMDSB-GSLJADNHSA-N fludrocortisone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O SYWHXTATXSMDSB-GSLJADNHSA-N 0.000 description 1
- 229960000676 flunisolide Drugs 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229960003336 fluorocortisol acetate Drugs 0.000 description 1
- 229940124307 fluoroquinolone Drugs 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 229960002464 fluoxetine Drugs 0.000 description 1
- 229960002419 flupentixol Drugs 0.000 description 1
- 229960002690 fluphenazine Drugs 0.000 description 1
- 229960002074 flutamide Drugs 0.000 description 1
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000004052 folic acid antagonist Substances 0.000 description 1
- 229960002258 fulvestrant Drugs 0.000 description 1
- 230000005714 functional activity Effects 0.000 description 1
- 238000002825 functional assay Methods 0.000 description 1
- 229960002963 ganciclovir Drugs 0.000 description 1
- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960005277 gemcitabine Drugs 0.000 description 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
- 208000029364 generalized anxiety disease Diseases 0.000 description 1
- 230000009395 genetic defect Effects 0.000 description 1
- 201000005442 glossopharyngeal neuralgia Diseases 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 229940015042 glycopyrrolate Drugs 0.000 description 1
- XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 description 1
- 229960002913 goserelin Drugs 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 239000003324 growth hormone secretagogue Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229960003878 haloperidol Drugs 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000003862 health status Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 229940125697 hormonal agent Drugs 0.000 description 1
- 102000053195 human P2RX7 Human genes 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229960000908 idarubicin Drugs 0.000 description 1
- 238000005417 image-selected in vivo spectroscopy Methods 0.000 description 1
- 239000012216 imaging agent Substances 0.000 description 1
- 229960003685 imatinib mesylate Drugs 0.000 description 1
- YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- 210000002865 immune cell Anatomy 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000005847 immunogenicity Effects 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 238000009169 immunotherapy Methods 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 229960001936 indinavir Drugs 0.000 description 1
- CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 1
- 125000004926 indolenyl group Chemical group 0.000 description 1
- 229960000598 infliximab Drugs 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 108091006086 inhibitor proteins Proteins 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000012739 integrated shape imaging system Methods 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 229940028885 interleukin-4 Drugs 0.000 description 1
- 208000028774 intestinal disease Diseases 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000007919 intrasynovial administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229950000831 iralukast Drugs 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229960004752 ketorolac Drugs 0.000 description 1
- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229940043355 kinase inhibitor Drugs 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 208000037805 labour Diseases 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 229940099584 lactobionate Drugs 0.000 description 1
- JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 229960001627 lamivudine Drugs 0.000 description 1
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 1
- GXESHMAMLJKROZ-IAPPQJPRSA-N lasofoxifene Chemical compound C1([C@@H]2[C@@H](C3=CC=C(C=C3CC2)O)C=2C=CC(OCCN3CCCC3)=CC=2)=CC=CC=C1 GXESHMAMLJKROZ-IAPPQJPRSA-N 0.000 description 1
- 229960002367 lasofoxifene Drugs 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229960003881 letrozole Drugs 0.000 description 1
- HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
- OTZRAYGBFWZKMX-JUDRUQEKSA-N leukotriene E4 Chemical compound CCCCCC=CCC=C\C=C\C=C\[C@@H](SC[C@H](N)C(O)=O)[C@@H](O)CCCC(O)=O OTZRAYGBFWZKMX-JUDRUQEKSA-N 0.000 description 1
- GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 description 1
- 229960004338 leuprorelin Drugs 0.000 description 1
- 229960001120 levocabastine Drugs 0.000 description 1
- ZCGOMHNNNFPNMX-KYTRFIICSA-N levocabastine Chemical compound C1([C@@]2(C(O)=O)CCN(C[C@H]2C)[C@@H]2CC[C@@](CC2)(C#N)C=2C=CC(F)=CC=2)=CC=CC=C1 ZCGOMHNNNFPNMX-KYTRFIICSA-N 0.000 description 1
- 229950008204 levosalbutamol Drugs 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229960001078 lithium Drugs 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960002202 lornoxicam Drugs 0.000 description 1
- OXROWJKCGCOJDO-JLHYYAGUSA-N lornoxicam Chemical compound O=C1C=2SC(Cl)=CC=2S(=O)(=O)N(C)\C1=C(\O)NC1=CC=CC=N1 OXROWJKCGCOJDO-JLHYYAGUSA-N 0.000 description 1
- KHPKQFYUPIUARC-UHFFFAOYSA-N lumiracoxib Chemical compound OC(=O)CC1=CC(C)=CC=C1NC1=C(F)C=CC=C1Cl KHPKQFYUPIUARC-UHFFFAOYSA-N 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- 229940072082 magnesium salicylate Drugs 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- OCSMOTCMPXTDND-OUAUKWLOSA-N marimastat Chemical compound CNC(=O)[C@H](C(C)(C)C)NC(=O)[C@H](CC(C)C)[C@H](O)C(=O)NO OCSMOTCMPXTDND-OUAUKWLOSA-N 0.000 description 1
- 229950008959 marimastat Drugs 0.000 description 1
- 229950001257 masilukast Drugs 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
- 229960004961 mechlorethamine Drugs 0.000 description 1
- 229960003803 meclofenamic acid Drugs 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 229960004296 megestrol acetate Drugs 0.000 description 1
- RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 description 1
- 229960001861 melperone Drugs 0.000 description 1
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
- 229960001924 melphalan Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000005906 menstruation Effects 0.000 description 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- SLVMESMUVMCQIY-UHFFFAOYSA-N mesoridazine Chemical compound CN1CCCCC1CCN1C2=CC(S(C)=O)=CC=C2SC2=CC=CC=C21 SLVMESMUVMCQIY-UHFFFAOYSA-N 0.000 description 1
- 229960000300 mesoridazine Drugs 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 239000003475 metalloproteinase inhibitor Substances 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 229940042053 methotrimeprazine Drugs 0.000 description 1
- VRQVVMDWGGWHTJ-CQSZACIVSA-N methotrimeprazine Chemical compound C1=CC=C2N(C[C@H](C)CN(C)C)C3=CC(OC)=CC=C3SC2=C1 VRQVVMDWGGWHTJ-CQSZACIVSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 229960004584 methylprednisolone Drugs 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 229960000282 metronidazole Drugs 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 210000000274 microglia Anatomy 0.000 description 1
- 230000003228 microsomal effect Effects 0.000 description 1
- 229940042472 mineral oil Drugs 0.000 description 1
- 229940101972 mirapex Drugs 0.000 description 1
- RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 description 1
- 229960001785 mirtazapine Drugs 0.000 description 1
- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 1
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 description 1
- 229960004857 mitomycin Drugs 0.000 description 1
- 229960001144 mizolastine Drugs 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 239000000472 muscarinic agonist Substances 0.000 description 1
- 210000003098 myoblast Anatomy 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- YBCBOXOAJAQPQU-UHFFFAOYSA-N n-(2-cyclohexyloxy-3-nitrophenyl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC([N+]([O-])=O)=C1OC1CCCCC1 YBCBOXOAJAQPQU-UHFFFAOYSA-N 0.000 description 1
- KTXBOOWDLPUROC-UHFFFAOYSA-N n-[2-(pyridine-3-carbonylamino)propyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(C)CNC(=O)C1=CC=CN=C1 KTXBOOWDLPUROC-UHFFFAOYSA-N 0.000 description 1
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 1
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
- NGZYRKGJWYJGRS-UHFFFAOYSA-N n-methylpyrrolidin-3-amine Chemical compound CNC1CCNC1 NGZYRKGJWYJGRS-UHFFFAOYSA-N 0.000 description 1
- 229960004270 nabumetone Drugs 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- AZKDTTQQTKDXLH-UHFFFAOYSA-N napthalene-2-carbonitrile Natural products C1=CC=CC2=CC(C#N)=CC=C21 AZKDTTQQTKDXLH-UHFFFAOYSA-N 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 229960002259 nedocromil sodium Drugs 0.000 description 1
- 230000017095 negative regulation of cell growth Effects 0.000 description 1
- 229960000884 nelfinavir Drugs 0.000 description 1
- QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 description 1
- 210000004498 neuroglial cell Anatomy 0.000 description 1
- 201000009985 neuronitis Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 230000004112 neuroprotection Effects 0.000 description 1
- 229960000689 nevirapine Drugs 0.000 description 1
- 229950009737 nicaraven Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960002653 nilutamide Drugs 0.000 description 1
- XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 description 1
- 229960000965 nimesulide Drugs 0.000 description 1
- HYWYRSMBCFDLJT-UHFFFAOYSA-N nimesulide Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1=CC=CC=C1 HYWYRSMBCFDLJT-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000002840 nitric oxide donor Substances 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 108020001162 nitroreductase Proteins 0.000 description 1
- OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical compound NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 1
- 230000001777 nootropic effect Effects 0.000 description 1
- 229960001158 nortriptyline Drugs 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000007523 nucleic acids Chemical group 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 0.000 description 1
- 229960005017 olanzapine Drugs 0.000 description 1
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 210000004248 oligodendroglia Anatomy 0.000 description 1
- 229960004110 olsalazine Drugs 0.000 description 1
- QQBDLJCYGRGAKP-FOCLMDBBSA-N olsalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=C(C(O)=CC=2)C(O)=O)=C1 QQBDLJCYGRGAKP-FOCLMDBBSA-N 0.000 description 1
- 229960000470 omalizumab Drugs 0.000 description 1
- SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical compound N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 description 1
- 229960000381 omeprazole Drugs 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000000668 oral spray Substances 0.000 description 1
- 229940041678 oral spray Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 description 1
- 229960003752 oseltamivir Drugs 0.000 description 1
- 229940053544 other antidepressants in atc Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- QNNHQVPFZIFNFK-UHFFFAOYSA-N oxazolo[4,5-b]pyridine Chemical compound C1=CC=C2OC=NC2=N1 QNNHQVPFZIFNFK-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 229960000649 oxyphenbutazone Drugs 0.000 description 1
- HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 description 1
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 description 1
- 210000003254 palate Anatomy 0.000 description 1
- 229960001057 paliperidone Drugs 0.000 description 1
- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229960004662 parecoxib Drugs 0.000 description 1
- TZRHLKRLEZJVIJ-UHFFFAOYSA-N parecoxib Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 TZRHLKRLEZJVIJ-UHFFFAOYSA-N 0.000 description 1
- 229960002296 paroxetine Drugs 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000013610 patient sample Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 208000028169 periodontal disease Diseases 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 210000002856 peripheral neuron Anatomy 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 229960000762 perphenazine Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- YKGCCFHSXQHWIG-UHFFFAOYSA-N phenothiazin-3-one Chemical compound C1=CC=C2SC3=CC(=O)C=CC3=NC2=C1 YKGCCFHSXQHWIG-UHFFFAOYSA-N 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004932 phenoxathinyl group Chemical group 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229950009195 phenylpropanol Drugs 0.000 description 1
- 229960000395 phenylpropanolamine Drugs 0.000 description 1
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 1
- 229960002036 phenytoin Drugs 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 125000005545 phthalimidyl group Chemical group 0.000 description 1
- 229960003634 pimozide Drugs 0.000 description 1
- YVUQSNJEYSNKRX-UHFFFAOYSA-N pimozide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 YVUQSNJEYSNKRX-UHFFFAOYSA-N 0.000 description 1
- XIMBESZRBTVIOD-UHFFFAOYSA-N piperidine-2-carboxamide Chemical compound NC(=O)C1CCCCN1 XIMBESZRBTVIOD-UHFFFAOYSA-N 0.000 description 1
- RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 1
- 229960004633 pirenzepine Drugs 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229960003171 plicamycin Drugs 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 208000019629 polyneuritis Diseases 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 229960003089 pramipexole Drugs 0.000 description 1
- 229960004583 pranlukast Drugs 0.000 description 1
- UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 229960002288 procaterol Drugs 0.000 description 1
- FKNXQNWAXFXVNW-BLLLJJGKSA-N procaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)[C@@H](NC(C)C)CC FKNXQNWAXFXVNW-BLLLJJGKSA-N 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229960003111 prochlorperazine Drugs 0.000 description 1
- WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 229940095055 progestogen systemic hormonal contraceptives Drugs 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- HVVNJUAVDAZWCB-UHFFFAOYSA-N prolinol Chemical compound OCC1CCCN1 HVVNJUAVDAZWCB-UHFFFAOYSA-N 0.000 description 1
- 229960003598 promazine Drugs 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 229960002934 propentofylline Drugs 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 229950008679 protamine sulfate Drugs 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 229940126409 proton pump inhibitor Drugs 0.000 description 1
- 239000000612 proton pump inhibitor Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 201000003651 pulmonary sarcoidosis Diseases 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- HAMAGKWXRRTWCJ-UHFFFAOYSA-N pyrido[2,3-b][1,4]oxazin-3-one Chemical compound C1=CN=C2OC(=O)C=NC2=C1 HAMAGKWXRRTWCJ-UHFFFAOYSA-N 0.000 description 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229960004431 quetiapine Drugs 0.000 description 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- WDXARTMCIRVMAE-UHFFFAOYSA-N quinoline-2-carbonitrile Chemical class C1=CC=CC2=NC(C#N)=CC=C21 WDXARTMCIRVMAE-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 229960004432 raltitrexed Drugs 0.000 description 1
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229940100618 rectal suppository Drugs 0.000 description 1
- 239000006215 rectal suppository Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000022983 regulation of cell cycle Effects 0.000 description 1
- 229940116176 remicade Drugs 0.000 description 1
- 229940113775 requip Drugs 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
- 229960000888 rimantadine Drugs 0.000 description 1
- 229960001534 risperidone Drugs 0.000 description 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
- 229960000311 ritonavir Drugs 0.000 description 1
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 1
- 229960004641 rituximab Drugs 0.000 description 1
- 229960004136 rivastigmine Drugs 0.000 description 1
- 229960001879 ropinirole Drugs 0.000 description 1
- 229960003522 roquinimex Drugs 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 229960000953 salsalate Drugs 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000003118 sandwich ELISA Methods 0.000 description 1
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 description 1
- 229960001852 saquinavir Drugs 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
- 229960002646 scopolamine Drugs 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229960003946 selegiline Drugs 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229960002930 sirolimus Drugs 0.000 description 1
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 1
- 229940084026 sodium valproate Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 201000001716 specific phobia Diseases 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960001203 stavudine Drugs 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 description 1
- 229960002211 sulfapyridine Drugs 0.000 description 1
- 229960001940 sulfasalazine Drugs 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
- 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
- 229960005349 sulfur Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000008093 supporting effect Effects 0.000 description 1
- 229960004492 suprofen Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229940127230 sympathomimetic drug Drugs 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229960001967 tacrolimus Drugs 0.000 description 1
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960001674 tegafur Drugs 0.000 description 1
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 description 1
- 229960003676 tenidap Drugs 0.000 description 1
- LXIKEPCNDFVJKC-QXMHVHEDSA-N tenidap Chemical compound C12=CC(Cl)=CC=C2N(C(=O)N)C(=O)\C1=C(/O)C1=CC=CS1 LXIKEPCNDFVJKC-QXMHVHEDSA-N 0.000 description 1
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
- 229960001278 teniposide Drugs 0.000 description 1
- 229960000351 terfenadine Drugs 0.000 description 1
- XTDXZSGSIMLARD-UHFFFAOYSA-N tert-butyl 2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC=CC=C1 XTDXZSGSIMLARD-UHFFFAOYSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229960003433 thalidomide Drugs 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
- WTBJIFNMKOKRJX-UHFFFAOYSA-N thiomorpholine-3-carboxamide Chemical compound NC(=O)C1CSCCN1 WTBJIFNMKOKRJX-UHFFFAOYSA-N 0.000 description 1
- 229960002784 thioridazine Drugs 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- MIMJSJSRRDZIPW-UHFFFAOYSA-N tilmacoxib Chemical compound C=1C=C(S(N)(=O)=O)C(F)=CC=1C=1OC(C)=NC=1C1CCCCC1 MIMJSJSRRDZIPW-UHFFFAOYSA-N 0.000 description 1
- 229960005013 tiotixene Drugs 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- 229960001017 tolmetin Drugs 0.000 description 1
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- 229960000303 topotecan Drugs 0.000 description 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
- 229960005026 toremifene Drugs 0.000 description 1
- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 229960001262 tramazoline Drugs 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011820 transgenic animal model Methods 0.000 description 1
- 230000009495 transient activation Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 229960000575 trastuzumab Drugs 0.000 description 1
- PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 1
- 229960003991 trazodone Drugs 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 229960005294 triamcinolone Drugs 0.000 description 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229960002324 trifluoperazine Drugs 0.000 description 1
- ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
- 229960002341 trifluperidol Drugs 0.000 description 1
- GPMXUUPHFNMNDH-UHFFFAOYSA-N trifluperidol Chemical compound C1CC(O)(C=2C=C(C=CC=2)C(F)(F)F)CCN1CCCC(=O)C1=CC=C(F)C=C1 GPMXUUPHFNMNDH-UHFFFAOYSA-N 0.000 description 1
- 229960003904 triflupromazine Drugs 0.000 description 1
- XSCGXQMFQXDFCW-UHFFFAOYSA-N triflupromazine Chemical compound C1=C(C(F)(F)F)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 XSCGXQMFQXDFCW-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 239000002447 tumor necrosis factor alpha converting enzyme inhibitor Substances 0.000 description 1
- 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 description 1
- 239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 description 1
- 108010072415 tumor necrosis factor precursor Proteins 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 208000014001 urinary system disease Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
- 229940093257 valacyclovir Drugs 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 208000027185 varicose disease Diseases 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000002525 vasculotropin inhibitor Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
- 229960004688 venlafaxine Drugs 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 208000009935 visceral pain Diseases 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229960000523 zalcitabine Drugs 0.000 description 1
- ARAIBEBZBOPLMB-UFGQHTETSA-N zanamivir Chemical compound CC(=O)N[C@@H]1[C@@H](N=C(N)N)C=C(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO ARAIBEBZBOPLMB-UFGQHTETSA-N 0.000 description 1
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
- 229960005332 zileuton Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229960000607 ziprasidone Drugs 0.000 description 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1
- WFPIAZLQTJBIFN-DVZOWYKESA-N zuclopenthixol Chemical compound C1CN(CCO)CCN1CC\C=C\1C2=CC(Cl)=CC=C2SC2=CC=CC=C2/1 WFPIAZLQTJBIFN-DVZOWYKESA-N 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
-
- 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
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- 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
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
本願は2014年6月5日に出願した米国仮出願第62/008,012の利益を主張し、その内容は参照によりその全体が本明細書に援用される。
本発明はP2X7のアンタゴニストとして有用なキノリン化合物に関する。本発明はまた、本発明の化合物を含有する薬学的に許容される組成物、及び様々な障害の治療における当該組成物の使用方法を提供する。
P2X7受容体は、プリン受容体ファミリーに属するリガンド依存性イオンチャネルである。当該受容体は免疫及び神経系に関連する多くの細胞型で発現される。神経系では、P2X7はミクログリア、オリゴデンドロサイト及びアストロサイトに発現される。その内在性リガンドATPでのP2X7受容体チャネルの簡単な活性化は、単球及びマクロファージからの炎症性サイトカインIL1−βのプロセシング及び放出を含むいくつかの下流の事象につながる。P2X7活性化は星状細胞でのグルタミン酸放出/吸収の調節において重要な役割も果たす。
現在、本発明の化合物、及びその薬学的に許容される組成物は、P2X7のアンタゴニストとして有効であることが見出された。そのような化合物は一般式I
、又はその薬学的に許容される塩を有する。
1.本発明の化合物の一般的な説明
特定の実施形態において、本発明はP2X7のアンタゴニストを提供する。幾つかの実施形態において、そのような化合物は本明細書中に記載の式の化合物、又はその薬学的に許容される塩を含み、ここで、各変数は本明細書中に定義され又は記載されるとおりである。
本発明の化合物は一般に上述のものを含み、本明細書中に開示されるクラス、サブクラス及び種によりさらに例示される。本明細書で使用されるときに、以下の定義は別段の断りがない限り適用されるであろう。本発明の目的で、化学元素は周期律表CASバージョン, Handbook of Chemistry and Physics, 75th Ed.によって特定される。さらに、有機化学の一般原理は“Organic Chemistry”, Thomas Sorrell, University Science Books, Sausalito:1999及び“March’s Advanced Organic Chemistry”, 5th Ed., Ed.:Smith, M.B.及びMarch, J., John Wiley & Sons, New York:2001に記載されており、その全内容をここに参照により取り込む。
−F、−Cl、−Br、−I、重水素、
−OH、保護ヒドロキシ、アルコキシ、オキソ、チオオキソ、
−NO2、−CN、CF3、N3、
−NH2、保護アミノ、−NHアルキル、−NHアルケニル、−NHアルキニル、−NHシクロアルキル、−NH−アリール、−NH−ヘテロアリール、−NH−複素環、−ジアルキルアミノ、−ジアリールアミノ、−ジヘテロアリールアミノ、
−O−アルキル、−O−アルケニル、−O−アルキニル、−O−シクロアルキル、−O−アリール、−O−ヘテロアリール、−O−複素環、
−C(O)−アルキル、−C(O)−アルケニル、−C(O)−アルキニル、−C(O)−カルボサイクリル(carbocyclyl)、−C(O)−アリール、−C(O)−ヘテロアリール、−C(O)−ヘテロサイクリル、
−CONH2、−CONH−アルキル、−CONH−アルケニル、−CONH−アルキニル、−CONH−カルボサイクリル、−CONH−アリール、−CONH−ヘテロアリール、−CONH−ヘテロサイクリル、
−OCO2−アルキル、−OCO2−アルケニル、−OCO2−アルキニル、−OCO2−カルボサイクリル、−OCO2−アリール、−OCO2−ヘテロアリール、−OCO2−ヘテロサイクリル、−OCONH2、−OCONH−アルキル、−OCONH−アルケニル、−OCONH−アルキニル、−OCONH−カルボサイクリル、−OCONH−アリール、−OCONH−ヘテロアリール、−OCONH−ヘテロサイクリル、
−NHC(O)−アルキル、−NHC(O)−アルケニル、−NHC(O)−アルキニル、−NHC(O)−カルボサイクリル、−NHC(O)−アリール、−NHC(O)−ヘテロアリール、−NHC(O)−ヘテロサイクリル、−NHCO2−アルキル、−NHCO2−アルケニル、−NHCO2−アルキニル、−NHCO2−カルボサイクリル、−NHCO2−アリール、−NHCO2−ヘテロアリール、−NHCO2−ヘテロサイクリル、−NHC(O)NH2、−NHC(O)NH−アルキル、−NHC(O)NH−アルケニル、−NHC(O)NH−アルケニル、−NHC(O)NH−カルボサイクリル、−NHC(O)NH−アリール、−NHC(O)NH−ヘテロアリール、−NHC(O)NH−ヘテロサイクリル、NHC(S)NH2、−NHC(S)NH−アルキル、−NHC(S)NH−アルケニル、−NHC(S)NH−アルキニル、−NHC(S)NH−カルボサイクリル、−NHC(S)NH−アリール、−NHC(S)NH−ヘテロアリール、−NHC(S)NH−ヘテロサイクリル、−NHC(NH)NH2、−NHC(NH)NH−アルキル、−NHC(NH)NH−アルケニル、−NHC(NH)NH−アルケニル、−NHC(NH)NH−カルボサイクリル、−NHC(NH)NH−アリール、−NHC(NH)NH−ヘテロアリール、−NHC(NH)NH−ヘテロサイクリル、−NHC(NH)−アルキル、−NHC(NH)−アルケニル、−NHC(NH)−アルケニル、−NHC(NH)−カルボサイクリル、−NHC(NH)−アリール、−NHC(NH)−ヘテロアリール、−NHC(NH)−ヘテロサイクリル、
−C(NH)NH−アルキル、−C(NH)NH−アルケニル、−C(NH)NH−アルキニル、−C(NH)NH−カルボサイクリル、−C(NH)NH−アリール、−C(NH)NH−ヘテロアリール、−C(NH)NH−ヘテロサイクリル、
−S(O)−アルキル、−S(O)−アルケニル、−S(O)−アルキニル、−S(O)−カルボサイクリル、−S(O)−アリール、−S(O)−ヘテロアリール、−S(O)−ヘテロサイクリル−SO2NH2、−SO2NH−アルキル、−SO2NH−アルケニル、−SO2NH−アルキニル、−SO2NH−カルボサイクリル、−SO2NH−アリール、−SO2NH−ヘテロアリール、−SO2NH−ヘテロサイクリル、
−NHSO2−アルキル、−NHSO2−アルケニル、−NHSO2−アルキニル、−NHSO2−カルボサイクリル、−NHSO2−アリール、−NHSO2−ヘテロアリール、−NHSO2−ヘテロサイクリル、
−CH2NH2、−CH2SO2CH3、
−モノ−、ジ−、又はトリ−アルキルシリル、
−アルキル、−アルケニル、−アルキニル、−アリール、−アリールアルキル、−ヘテロアリール、−ヘテロアリールアルキル、−ヘテロシクロアルキル、−シクロアルキル、−炭素環、−複素環、ポリアルコキシアルキル、ポリアルコキシ、−メトキシメトキシ、−メトキシエトキシ、−SH、−S−アルキル、−S−アルケニル、−S−アルキニル、−S−カルボサイクリル、−S−アリール、−S−ヘテロアリール、−S−ヘテロサイクリル、又はメチルチオメチル、
が挙げられる。
1つの態様によると、本発明は、式I
R1は、水素、C1-6脂肪族、C5-10アリール、3〜8員の飽和又は部分不飽和の炭素環、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する3〜7員の複素環、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する5〜6員の単環式ヘテロアリール環、縮合7〜10員二環式飽和、部分不飽和環、アリール、又はヘテロアリール環であり;その各々はRAの1〜5個によって場合により置換されていてよく;あるいはR1は−OR、−SR、−CN、−NO2、−SO2R、−SOR、−C(O)R、−CO2R、−C(O)N(R)2、−NRC(O)R、−NRC(O)N(R)2、−NRSO2R、又は−N(R)2であり;
各RAは独立して、−R、ハロゲン、−ハロアルキル、−ヒドロキシアルキル、−OR、−SR、−CN、−NO2、−SO2R、−SOR、−C(O)R、−CO2R、−C(O)N(R)2、−NRC(O)R、−NRC(O)N(R)2、−NRSO2R、又は−N(R)2であり;
ここで、R1が1個の窒素がキノリン環に結合している1〜4個の窒素を有する3〜7員の複素環である場合、RAは、−R、ハロゲン、−ハロアルキル、−ヒドロキシアルキル、−SR、−CN、−NO2、−SO2R、−SOR、−C(O)R、−CO2R、−C(O)N(R)2、−NRC(O)R、−NRC(O)N(R)2、−NRSO2R、又は−N(R)2であり;
ここで、R1が1個の窒素がキノリン環に結合している1〜4個の窒素を有する3〜7員の複素環であり、かつRAが−ORである場合、少なくとも1つのR2はハロゲンであり;
Zは、O、S、SO2、SO、C(O)、CO2、C(O)N(R)、NRC(O)、NRC(O)N(R)、NRSO2、又はN(R)であり;
環Aは、3〜8員の飽和又は部分不飽和の炭素環、又は、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する3〜7員の複素環であり;
各R2は独立して、−R、ハロゲン、−ハロアルキル、−OR、−SR、−CN、−NO2、−SO2R、−SOR、−C(O)R、−CO2R、−C(O)N(R)2、−NRC(O)R、−NRC(O)N(R)2、−NRSO2R、又は−N(R)2であり;あるいは同じ原子上の2つのR2基は、それらが結合している原子と一緒になって、C3-10アリール、3〜8員の飽和又は部分不飽和の炭素環、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する3〜7員の複素環、又は、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する5〜6員の単環式ヘテロアリール環を形成し;その各々は場合により置換されていてよく;
各Rは独立して、水素、C1-6脂肪族、C3-10アリール、3〜8員の飽和又は部分不飽和の炭素環、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する3〜7員の複素環、又は、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する5〜6員の単環式ヘテロアリール環であり;その各々は場合により置換されていてよく;あるいは
同じ原子上の2つのR基は、それらが結合している原子と一緒になって、C3-10アリール、3〜8員の飽和又は部分不飽和の炭素環、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する3〜7員の複素環、又は、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する5〜6員の単環式ヘテロアリール環を形成し;その各々は場合により置換されていてよく;
mは0、1、又は2であり;かつ
nは1、2、3、4、又は5であり;
ここで、RA又はR2の少なくとも1つはハロゲン又はハロアルキルであり、あるいは少なくとも1つのR2は−ORであり;そして
ここで、以下の化合物:
6−クロロ−N−{[(1S,3S)−1−ヒドロキシ−3−メチルシクロヘキシル]メチル}−2−[(3S)−3−ヒドロキシピロリジン−1−イル]キノリン−5−カルボキサミド;
6−クロロ−N−{[(1S,3S)−1−ヒドロキシ−3−メチルシクロヘキシル]メチル}−2−[(3R)−3−ヒドロキシピロリジン−1−イル]キノリン−5−カルボキサミド;
6−クロロ−N−{[(1S,3S)−1−ヒドロキシ−3−メチルシクロヘキシル]メチル}−2−(4−ヒドロキシピペリジン−1−イル]キノリン−5−カルボキサミド;及び
6−クロロ−N−{[(1S,3S)−1−ヒドロキシ−3−メチルシクロヘキシル]メチル}−2−(3−ヒドロキシ−3−メチルピロリジン−1−イル]キノリン−5−カルボキサミド、
を除く)
の化合物、又はその薬学的に許容される塩を提供する。
の化合物、又はその薬学的に許容される塩を提供する。
の化合物、又はその薬学的に許容される塩を提供する。
の化合物、又はその薬学的に許容される塩を提供する。
の化合物、又はその薬学的に許容される塩を提供する。
薬学的に許容される組成物
別の実施形態によれば、本発明は、本発明の化合物又はその薬学的に許容される誘導体及び薬学的に許容される担体、アジュバント又はビヒクルを含む組成物を提供する。本発明の組成物における化合物の量は、生体試料又は患者において、P2X7を測定可能に調節するのに有効であるような量である。特定の実施形態において、本発明の組成物における化合物の量は、生体試料又は患者において、P2X7を測定可能に調節するのに有効であるような量である。特定の実施形態において、本発明の組成物は、そのような組成物を必要とする患者に投与するように製剤される。
特定の実施形態において、本発明は、患者又は生体試料において積極的にP2X7に拮抗するための方法であって、本発明に係る化合物を当該患者に投与し、又は当該生体試料と接触させるステップを含む、方法を提供する。
(i)医学腫瘍学で使用される抗増殖/抗腫瘍薬又はそれらの組み合わせ、例えばアルキル化剤(例えばシスプラチン、カルボプラチン、シクロホスファミド、ナイトロジェンマスタード、メルファラン、クロラムブシル、ブスルファン又はニトロソウレア);代謝拮抗物質(例えば抗葉酸剤、例えば5−フルオロウラシル又はテガフールなどのフルオロピリミジン、ラルチトレキセド、メトトレキサート、シトシンアラビノシド、ヒドロキシウレア、ゲムシタビンあるいはパクリタキセル);抗腫瘍抗生物質(例えばアントラサイクリン、例えばアドリアマイシン、ブレオマイシン、ドキソルビシン、ダウノマイシン、エピルビシン、イダルビシン、マイトマイシンC、ダクチノマイシン又はミトラマイシン);抗有糸分裂剤(例えばビンカアルカロイド、例えばビンクリスチン、ビンブラスチン、ビンデシン又はビノレルビン、あるいはタキソイド、例えばタキソール又はタキソテール);あるいはトポイソメラーゼ阻害剤(例えばエピポドフィロトキシン、例えばエトポシド、テニポシド、アムサクリン、トポテカン又はカンプトテシン);(ii)細胞増殖抑制剤、例えば抗エストロゲン(例えばタモキシフェン、トレミフェン、ラロキシフェン、ドロロキシフェン又はヨードキシフェン(iodoxyfene))、エストロゲン受容体下方制御因子(例えばフルベストラント)、抗アンドロゲン剤(例えばビカルタミド、フルタミド、ニルタミド又は酢酸シプロテロン)、LHRHアンタゴニスト又はLHRHアゴニスト(例えばゴセレリン、リュープロレリン又はブセレリン)、プロゲストゲン(例えば酢酸メゲストロール)、アロマターゼ阻害剤(例えばアナストロゾール、レトロゾール、ボラゾール又はエキセメスタンなど)又は5α−レダクターゼの阻害剤、例えばフィナステリド;(iii)がん細胞の浸潤を阻害する薬剤(例えばマリマスタットのようなメタロプロテイナーゼ阻害剤又はウロキナーゼプラスミノーゲン活性化因子受容体機能の阻害剤);(iv)増殖因子機能の阻害剤、例えば:増殖因子抗体(例えば抗erbb2抗体トラスツズマブ、又は抗erbb1抗体セツキシマブ[C225])、ファルネシルトランスフェラーゼ阻害剤、チロシンキナーゼ阻害剤又はセリン/スレオニンキナーゼ阻害剤、上皮成長因子ファミリーの阻害剤(例えばEGFRファミリーチロシンキナーゼ阻害剤、例えばN−(3−クロロ−4−フルオロフェニル)−7−メトキシ−6−(3−モルホリノプロポキシ)キナゾリン−4−アミン(ゲフィチニブ、AZD1839)、N−(3−エチニルフェニル)−6,7−ビス(2−メトキシエトキシ)キナゾリン−4−アミン(エルロチニブ、OSI−774)又は6−アクリルアミド−N−(3−クロロ−4−フルオロフェニル)−7−(3−モルホリノプロポキシ)キナゾリン−4−アミン(CI−1033))、血小板由来増殖因子ファミリーの阻害剤、又は肝細胞増殖因子ファミリーの阻害剤;(v)抗血管新生剤、例えば血管内皮増殖因子の作用を阻害するもの(例えば抗血管内皮細胞増殖因子抗体ベバシズマブ、リノマイド、インテグリンαvβ3機能の阻害剤又はアンギオスタチン);(vi)血管損傷剤、例えばコンブレタスタチンA4;(vii)アンチセンス治療に用いられる薬剤、例えば上記に列挙した標的に向けられるもの、例えばISIS2503、抗rasアンチセンス;(viii)遺伝子治療アプローチに用いられる薬剤、例えば異常な遺伝子、例えば異常なp53又は異常なBRCA1もしくはBRCA2を置換するアプローチ、GDEPT(遺伝子指向性酵素プロドラッグ治療)アプローチ、例えばシトシンデアミナーゼ、チミジンキナーゼ又は細菌ニトロレダクターゼ酵素を使用するもの、ならびに、化学療法又は放射線療法に対する患者の耐性を増加させるアプローチ、例えば多剤耐性遺伝子治療;あるいは、(ix)免疫療法アプローチに用いられる薬剤、例えば患者腫瘍細胞の免疫原性を増加させるエクスビボ(ex−vivo)及びインビボ(in−vivo)アプローチ、例えばサイトカイン、例えばインターロイキン2、インターロイキン4又は顆粒球−マクロファージコロニー刺激因子でのトランスフェクション、トランスフェクトされた免疫細胞を用いてT細胞アネルギーを減少させるアプローチ、例えばサイトカイントランスフェクト樹状細胞を用いるアプローチ、サイトカイントランスフェクト腫瘍細胞ラインを用いるアプローチ、及び抗イディオタイプ抗体を用いるアプローチ、が挙げられる。
以下の実施例に示されるように、特定の例示的な実施形態において、化合物は、以下の一般的手順に従って調製される。一般的な方法が、本発明の特定の化合物の合成を記載しているが、以下の一般的な方法及び当業者に知られている他の方法は、本明細書中に記載されるとおりの、これらの各化合物の全ての化合物及びサブクラス及び種に適用することができることは理解されるであろう。
作動時間:6.5分
流速:1.0mL/分
勾配:4.5分で5〜95%B、波長254及び215nM
カラム:Waters Sunfire C18、3.0x50mm、3.5um+veモード
マススキャン:100〜900Da
表題化合物を実施例126に記載された手順に従って、6−クロロ−2−シクロペント−1−エニル−キノリン−5−カルボン酸((1S,3S)−1−ヒドロキシ−3−メチル−シクロヘキシルメチル)−アミドを使用して合成した。1H NMR(400 MHz, DMSO-d6):δ 8.59(t, J = 6.03 Hz, 1H), 8.10(d, J = 8.81 Hz, 1H), 7.95(d, J = 9.23 Hz, 1H), 7.75(d, J = 8.81 Hz, 1H), 7.59(d, J = 8.81 Hz, 1H), 3.37-3.39(m, 1H), 3.29-3.30(m, 2H), 2.06-2.08(m, 2H), 1.67-1.87(m, 7H), 1.54-1.65(m, 4H), 1.12-1.47(m, 1H), 1.23-1.32(m, 3H), 1.02-1.08(m, 1H), 0.83-0.85(m, 3H)。m/z:401.2 [M + H] +
IL−1β放出アッセイ:ATPによるP2X7の活性化は、プロIL−1βの活性IL−1βへの変換に続くCa2+の流入を生じる細胞の速やかな一時的活性化をもたらす。P2X7化合物の機能的活性を、サンドイッチELISAにより検出した、THP−1細胞の培養培地中での成熟IL−1βの放出によって測定した。細胞を完全増殖培地(RPMI 1640+10%HI−FCS+2mM L−グルタミン+1x PS)中で維持した。3日毎に、細胞密度が50万細胞/mlを超えないように、細胞を1/3から1/4に希釈することによって、培地を更新した(播種細胞密度@1x105/ml)。THP−1細胞を100gで3分間の遠心分離によって50mlのフラスコから回収した。細胞を0.5μMのPMAを添加した培地中で2x105細胞/mlに再懸濁し、インキュベートした。細胞を洗浄し、10ng/mlのLPSで補足した培地中で1.5x105細胞/mlに再懸濁し、そして細胞を4時間37℃、5%CO2でプライミングした。予備希釈した試験化合物の20μLの添加後、ブランク、標準及び対照試薬、細胞をさらに20分間37℃でインキュベートし、0.8mMのBzATPで30分間刺激した。細胞を遠心分離し、上清を回収し、そして成熟IL−1βの存在を製造者の指示に従ってデュアルヒトIL−1βキットを使用して検出した。テトラヒドロベンゾジアゼピン(tetrahydrobenzodiazepine)アナログは、P2X7受容体の活性化によって放出される炎症誘発性サイトカインIL−1βのレベルによって測定されたように細胞中のP2X7の活性を効果的に調節した。
アゴニスト誘導性の孔形成を、ヒトP2X7受容体でトランスフェクトしたHEK293においてYO PRO蛍光染料の細胞取り込みを測定することによって決定した。ヒトP2X7を過剰発現するHEK293細胞をT75 cmフラスコから細胞を剥離するHQTase試薬を使用して回収した。回収した細胞を1200rpmで5分間室温で遠心分離する。細胞の生存率をトリパンブルー染色によって決定し、そして細胞を384W BDポリリシンコーティングプレート中に50μlの容積で10,000細胞/ウェルで播種し、一晩37℃でインキュベートする。一晩のインキュベーション後、培地を35μl/ウェルのアッセイ緩衝液(5mMのKCl、0.1mMのCaCl2、5mMグルコース、125mMのNaClを含む10mMのHEPES緩衝液pH7.4)で交換した。化合物の段階希釈をBravo液体ハンドリング装置を使用して行い、そして化合物を10点について3つの希釈で2.5μMから始める細胞アッセイプレートにBravoを使用して添加した。陽性対照阻害剤化合物をカラム23に添加した。プレートをプレートシェイカー上で10秒間ゆっくりと振とうし。細胞を20分間室温で化合物とインキュベートした。インキュベーション期間後に、BzATP(10μM)とともにYO PRO染料(1μM)を10μl/ウェルで細胞に添加した。プレートを1000rpmで5秒間遠心分離し、室温で30分間インキュベートした。細胞中へのYO PRO染料の取り込みをEnvision蛍光プレートリーダー装置(パーキンエルマー(Perkin Elmer))を使用して測定した。
E >1μM;
D 500〜999nM;
C 101〜500nM;
B 10〜100nM;
A <10nM。
医薬製剤
(A)注射バイアル:本発明に係る活性成分100g及びリン酸水素二ナトリウム5gの3lの二回蒸留した水中の溶液を、2N塩酸を用いてpH6.5に調節し、無菌ろ過し、注射バイアル中に移し、無菌状態で凍結乾燥し、そして無菌条件下でシールする。各注射バイアルは5mgの活性成分を含む。
Claims (20)
- 式I
R1は、水素、C1-6脂肪族、C5-10アリール、3〜8員の飽和又は部分不飽和の炭素環、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する3〜7員の複素環、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する5〜6員の単環式ヘテロアリール環、縮合7〜10員二環式飽和、部分不飽和環、アリール、又はヘテロアリール環であり;その各々はRAの1〜5個で場合により置換されていてよく;あるいはR1は−OR、−SR、−CN、−NO2、−SO2R、−SOR、−C(O)R、−CO2R、−C(O)N(R)2、−NRC(O)R、−NRC(O)N(R)2、−NRSO2R、又は−N(R)2であり;
各RAは独立して、−R、ハロゲン、−ハロアルキル、−ヒドロキシアルキル、−OR、−SR、−CN、−NO2、−SO2R、−SOR、−C(O)R、−CO2R、−C(O)N(R)2、−NRC(O)R、−NRC(O)N(R)2、−NRSO2R、又は−N(R)2であり;
ここで、R1が1個の窒素がキノリン環に結合している1〜4個の窒素を有する3〜7員の複素環である場合、RAは−R、ハロゲン、−ハロアルキル、−ヒドロキシアルキル、−SR、−CN、−NO2、−SO2R、−SOR、−C(O)R、−CO2R、−C(O)N(R)2、−NRC(O)R、−NRC(O)N(R)2、−NRSO2R、又は−N(R)2であり;
ここで、R1が1個の窒素がキノリン環に結合している1〜4個の窒素を有する3〜7員の複素環であり、かつRAが−ORである場合、少なくとも1つのR2はハロゲンであり;
Zは、O、S、SO2、SO、C(O)、CO2、C(O)N(R)、NRC(O)、NRC(O)N(R)、NRSO2、又はN(R)であり;
環Aは、3〜8員の飽和又は部分不飽和の炭素環、又は、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する3〜7員の複素環であり;
各R2は独立して、−R、ハロゲン、−ハロアルキル、−OR、−SR、−CN、−NO2、−SO2R、−SOR、−C(O)R、−CO2R、−C(O)N(R)2、−NRC(O)R、−NRC(O)N(R)2、−NRSO2R、又は−N(R)2であり;あるいは同じ原子上の2つのR2基は、それらが結合している原子と一緒になって、C3-10アリール、3〜8員の飽和又は部分不飽和の炭素環、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する3〜7員の複素環、又は、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する5〜6員の単環式ヘテロアリール環を形成し;その各々は場合により置換されていてよく;
各Rは独立して、水素、C1-6脂肪族、C3-10アリール、3〜8員の飽和又は部分不飽和の炭素環、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する3〜7員の複素環、又は、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する5〜6員の単環式ヘテロアリール環であり;その各々は場合により置換されていてよく;あるいは
同じ原子上の2つのR基は、それらが結合している原子と一緒になって、C3-10アリール、3〜8員の飽和又は部分不飽和の炭素環、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する3〜7員の複素環、又は、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する5〜6員の単環式ヘテロアリール環を形成し;その各々は場合により置換されていてよく;
mは0、1、又は2であり;かつ
nは1、2、3、4、又は5であり;
ここで、RA又はR2の少なくとも1つはハロゲン又はハロアルキルであり、あるいは少なくとも1つのR2が−ORであり;そして
ここで、以下の化合物:
6−クロロ−N−{[(1S,3S)−1−ヒドロキシ−3−メチルシクロヘキシル]メチル}−2−[(3S)−3−ヒドロキシピロリジン−1−イル]キノリン−5−カルボキサミド;
6−クロロ−N−{[(1S,3S)−1−ヒドロキシ−3−メチルシクロヘキシル]メチル}−2−[(3R)−3−ヒドロキシピロリジン−1−イル]キノリン−5−カルボキサミド;
6−クロロ−N−{[(1S,3S)−1−ヒドロキシ−3−メチルシクロヘキシル]メチル}−2−(4−ヒドロキシピペリジン−1−イル]キノリン−5−カルボキサミド;及び
6−クロロ−N−{[(1S,3S)−1−ヒドロキシ−3−メチルシクロヘキシル]メチル}−2−(3−ヒドロキシ−3−メチルピロリジン−1−イル]キノリン−5−カルボキサミド、
を除く)
の化合物、又はその薬学的に許容される塩。 - RA又はR2の少なくとも1つがFであり、あるいはR2の少なくとも1つがOHである、請求項1に記載の化合物。
- R1が水素である、請求項1に記載の化合物。
- R1がC5-10アリール、3〜8員の飽和又は部分不飽和の炭素環、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する3〜7員の複素環、窒素、酸素、もしくは硫黄から独立して選ばれる1〜4個のヘテロ原子を有する5〜6員の単環式ヘテロアリール環、縮合7〜10員二環式飽和、部分不飽和環、アリール、又はヘテロアリール環であり;その各々はRAの1〜5個で場合により置換されていてよい、請求項1に記載の化合物。
- R1が−OR、−SR、−SO2R、−SOR、−NRC(O)R、−NRC(O)N(R)2、−NRSO2R、又は−N(R)2である、請求項1に記載の化合物。
- ZがC(O)N(R)である、請求項1に記載の化合物。
- 環Aが、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、モルホリニル、テトラヒドロピラニル、ピペラジニル、ピペリジニル、ピロリジニル、ピロリニル、2H−ピロリル、ピロリル、テトラヒドロフラニル、オキセタニル、又はアゼチジニルである、請求項1に記載の化合物。
- 環Aが、シクロヘキシル又はシクロヘプチルである、請求項1に記載の化合物。
- 各R2が独立してHである、請求項1に記載の化合物。
- 各R2が独立して、メチル、F、CF3、又はOHである、請求項1に記載の化合物。
- 表1から選ばれる請求項1に記載の化合物。
- 請求項1に記載の化合物、及び薬学的に許容されるアジュバント、担体、又はビヒクルを含有する、医薬組成物。
- 対象又は生体試料中におけるP2X7活性を調節するための方法であって、請求項1に記載の化合物又はその生理学的に許容される塩を、当該対象に投与し、又は当該生体試料に接触させるステップを含む、方法。
- P2X7媒介疾患又は障害の治療を必要とする対象の当該疾患又は障害を治療するための方法であって、当該対象に請求項1に記載の化合物を投与するステップを含む、方法。
- 前記疾患又は障害が、パーキンソン病、多発性硬化症(MS);アルツハイマー病、外傷性脳損傷、脳炎;うつ病躁病(depression mania)、双極性疾患、不安症、統合失調症、摂食障害、睡眠障害、認知障害;てんかん、発作性疾患;尿失禁、排尿困難、直腸過敏症、便失禁、良性前立腺肥大症、炎症性腸疾患;アレルギー性鼻炎、喘息、反応性気道疾患、慢性閉塞性肺疾患;関節リウマチ、変形性関節症、心筋梗塞、ブドウ膜炎、アテローム性動脈硬化症;あるいは乾癬である、請求項17に記載の方法。
- 対象の多発性硬化症を治療するための方法であって、当該対象に請求項1に記載の化合物又はその生理学的に許容される塩を投与するステップを含む、方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201462008012P | 2014-06-05 | 2014-06-05 | |
US62/008,012 | 2014-06-05 | ||
PCT/US2015/034108 WO2015187905A1 (en) | 2014-06-05 | 2015-06-04 | Novel quinoline derivatives and their use in neurodegenerative diseases |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2017520538A true JP2017520538A (ja) | 2017-07-27 |
JP2017520538A5 JP2017520538A5 (ja) | 2018-05-31 |
JP6692759B2 JP6692759B2 (ja) | 2020-05-13 |
Family
ID=53385999
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016571149A Expired - Fee Related JP6692759B2 (ja) | 2014-06-05 | 2015-06-04 | 新規キノリン誘導体及び神経変性疾患におけるそれらの使用 |
Country Status (9)
Country | Link |
---|---|
US (2) | US9399623B2 (ja) |
EP (1) | EP3152192A1 (ja) |
JP (1) | JP6692759B2 (ja) |
CN (1) | CN106573907B (ja) |
AR (1) | AR100724A1 (ja) |
AU (1) | AU2015269598B2 (ja) |
CA (1) | CA2948888A1 (ja) |
IL (1) | IL249308B (ja) |
WO (1) | WO2015187905A1 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8563573B2 (en) | 2007-11-02 | 2013-10-22 | Vertex Pharmaceuticals Incorporated | Azaindole derivatives as CFTR modulators |
US8802868B2 (en) | 2010-03-25 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Solid forms of (R)-1(2,2-difluorobenzo[D][1,3]dioxo1-5-yl)-N-(1-(2,3-dihydroxypropyl-6-fluoro-2-(1-hydroxy-2-methylpropan2-yl)-1H-Indol-5-yl)-Cyclopropanecarboxamide |
EP3381899B1 (en) | 2010-04-22 | 2021-01-06 | Vertex Pharmaceuticals Incorporated | Intermediate compound for process of producing cycloalkylcarboxamido-indole compounds |
RS57476B9 (sr) | 2014-04-15 | 2021-10-29 | Vertex Pharma | Farmaceutske kompozicije za lečenje bolesti posredovanih transmembranskim regulatorom provodljivosti cistične fibroze |
WO2015187905A1 (en) * | 2014-06-05 | 2015-12-10 | Merck Patent Gmbh | Novel quinoline derivatives and their use in neurodegenerative diseases |
TWI764999B (zh) * | 2017-03-13 | 2022-05-21 | 日商拉夸里亞創藥股份有限公司 | 作為p2x7受體拮抗劑之四氫喹啉衍生物 |
MX2021003158A (es) | 2018-09-18 | 2021-07-16 | Nikang Therapeutics Inc | Derivados de anillo tricíclico condensado como inhibidores de la fosfatasa de homología a src 2. |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005528363A (ja) * | 2002-03-25 | 2005-09-22 | アストラゼネカ・アクチエボラーグ | 新規アダマンタン誘導体 |
JP2006526617A (ja) * | 2003-06-02 | 2006-11-24 | アストラゼネカ・アクチエボラーグ | 新規p2x7受容体アンタゴニストおよびその用途 |
JP2007500187A (ja) * | 2003-07-28 | 2007-01-11 | アストラゼネカ・アクチエボラーグ | キノリン誘導体および治療におけるその使用 |
WO2008013494A1 (en) * | 2006-07-27 | 2008-01-31 | Astrazeneca Ab | Quinoline derivatives as p2x7 receptor antagonist and their use in the treatment of rheumatoid arthritis, osteoarthritis, copd and ibd |
JP2008521894A (ja) * | 2004-11-30 | 2008-06-26 | アストラゼネカ・アクチエボラーグ | 新規化合物 |
JP2010520875A (ja) * | 2007-03-09 | 2010-06-17 | レノビス, インコーポレイテッド | P2x7調節因子としてのビシクロヘテロアリール化合物およびその使用 |
JP2010522227A (ja) * | 2007-03-22 | 2010-07-01 | アストラゼネカ・アクチエボラーグ | 炎症性疾患の処置のためのキノリン誘導体 |
JP2011505356A (ja) * | 2007-11-30 | 2011-02-24 | アストラゼネカ・アクチエボラーグ | P2x7受容体アンタゴニストとして作用するキノリン誘導体 |
JP2011518226A (ja) * | 2008-04-22 | 2011-06-23 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | キノリン若しくはイソキノリン置換p2x7アンタゴニスト |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1307193A1 (en) | 2000-07-27 | 2003-05-07 | Affymax Research Institute | Agonists of follicle stimulating hormone activity |
WO2015187905A1 (en) * | 2014-06-05 | 2015-12-10 | Merck Patent Gmbh | Novel quinoline derivatives and their use in neurodegenerative diseases |
-
2015
- 2015-06-04 WO PCT/US2015/034108 patent/WO2015187905A1/en active Application Filing
- 2015-06-04 JP JP2016571149A patent/JP6692759B2/ja not_active Expired - Fee Related
- 2015-06-04 CA CA2948888A patent/CA2948888A1/en not_active Abandoned
- 2015-06-04 US US14/730,351 patent/US9399623B2/en active Active
- 2015-06-04 AU AU2015269598A patent/AU2015269598B2/en not_active Ceased
- 2015-06-04 AR ARP150101761A patent/AR100724A1/es unknown
- 2015-06-04 CN CN201580041824.6A patent/CN106573907B/zh not_active Expired - Fee Related
- 2015-06-04 EP EP15728739.2A patent/EP3152192A1/en not_active Withdrawn
-
2016
- 2016-06-21 US US15/188,301 patent/US20160296509A1/en not_active Abandoned
- 2016-11-30 IL IL249308A patent/IL249308B/en active IP Right Grant
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005528363A (ja) * | 2002-03-25 | 2005-09-22 | アストラゼネカ・アクチエボラーグ | 新規アダマンタン誘導体 |
JP2006526617A (ja) * | 2003-06-02 | 2006-11-24 | アストラゼネカ・アクチエボラーグ | 新規p2x7受容体アンタゴニストおよびその用途 |
JP2007500187A (ja) * | 2003-07-28 | 2007-01-11 | アストラゼネカ・アクチエボラーグ | キノリン誘導体および治療におけるその使用 |
JP2008521894A (ja) * | 2004-11-30 | 2008-06-26 | アストラゼネカ・アクチエボラーグ | 新規化合物 |
WO2008013494A1 (en) * | 2006-07-27 | 2008-01-31 | Astrazeneca Ab | Quinoline derivatives as p2x7 receptor antagonist and their use in the treatment of rheumatoid arthritis, osteoarthritis, copd and ibd |
JP2010520875A (ja) * | 2007-03-09 | 2010-06-17 | レノビス, インコーポレイテッド | P2x7調節因子としてのビシクロヘテロアリール化合物およびその使用 |
JP2010522227A (ja) * | 2007-03-22 | 2010-07-01 | アストラゼネカ・アクチエボラーグ | 炎症性疾患の処置のためのキノリン誘導体 |
JP2011505356A (ja) * | 2007-11-30 | 2011-02-24 | アストラゼネカ・アクチエボラーグ | P2x7受容体アンタゴニストとして作用するキノリン誘導体 |
JP2011518226A (ja) * | 2008-04-22 | 2011-06-23 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | キノリン若しくはイソキノリン置換p2x7アンタゴニスト |
Non-Patent Citations (1)
Title |
---|
JOURNAL OF MEDICINAL CHEMISTRY, vol. Vol.52(10), JPN6018045433, 2009, pages 3123 - 3141, ISSN: 0004134364 * |
Also Published As
Publication number | Publication date |
---|---|
AR100724A1 (es) | 2016-10-26 |
AU2015269598A1 (en) | 2016-11-24 |
IL249308A0 (en) | 2017-02-28 |
US20150353497A1 (en) | 2015-12-10 |
US9399623B2 (en) | 2016-07-26 |
IL249308B (en) | 2020-02-27 |
US20160296509A1 (en) | 2016-10-13 |
EP3152192A1 (en) | 2017-04-12 |
JP6692759B2 (ja) | 2020-05-13 |
AU2015269598B2 (en) | 2019-11-14 |
WO2015187905A1 (en) | 2015-12-10 |
CN106573907A (zh) | 2017-04-19 |
CN106573907B (zh) | 2020-09-08 |
CA2948888A1 (en) | 2015-12-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6692759B2 (ja) | 新規キノリン誘導体及び神経変性疾患におけるそれらの使用 | |
ES2944573T3 (es) | Antagonistas de TLR7/8 y usos de los mismos | |
JP6571756B2 (ja) | 神経変性疾患に適応可能なインドリジン誘導体 | |
US10836750B1 (en) | TLR7/8 antagonists and uses thereof | |
US10676433B2 (en) | Indole derivatives and their use in neurodegenerative diseases |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180412 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180412 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20181115 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20181120 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20190220 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190520 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20191015 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200213 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20200225 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20200317 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20200415 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6692759 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
LAPS | Cancellation because of no payment of annual fees |