ZA200504720B - Novel aminobenzophenone compounds - Google Patents
Novel aminobenzophenone compounds Download PDFInfo
- Publication number
- ZA200504720B ZA200504720B ZA200504720A ZA200504720A ZA200504720B ZA 200504720 B ZA200504720 B ZA 200504720B ZA 200504720 A ZA200504720 A ZA 200504720A ZA 200504720 A ZA200504720 A ZA 200504720A ZA 200504720 B ZA200504720 B ZA 200504720B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- phenyl
- chloro
- fluoro
- carbamoyloxy
- Prior art date
Links
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 title description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 213
- -1 hydroxy, mercapto Chemical group 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 19
- 125000003282 alkyl amino group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([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
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 9
- 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 claims 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 4
- 108010003541 Platelet Activating Factor Proteins 0.000 claims 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 claims 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 claims 2
- SQVNITZYWXMWOG-UHFFFAOYSA-N 2-cyclohexyl-1-(2-methylquinolin-4-yl)-3-(1,3-thiazol-2-yl)guanidine Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(=NC1CCCCC1)NC1=NC=CS1 SQVNITZYWXMWOG-UHFFFAOYSA-N 0.000 claims 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 claims 2
- UGUBQKZSNQWWEV-UHFFFAOYSA-N 4-oxo-4-phenylmethoxybutanoic acid Chemical compound OC(=O)CCC(=O)OCC1=CC=CC=C1 UGUBQKZSNQWWEV-UHFFFAOYSA-N 0.000 claims 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims 2
- 206010012442 Dermatitis contact Diseases 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 229930003316 Vitamin D Natural products 0.000 claims 2
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims 2
- 206010000496 acne Diseases 0.000 claims 2
- 239000000464 adrenergic agent Substances 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 230000007815 allergy Effects 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 230000001387 anti-histamine Effects 0.000 claims 2
- 229940125715 antihistaminic agent Drugs 0.000 claims 2
- 239000000739 antihistaminic agent Substances 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 208000010247 contact dermatitis Diseases 0.000 claims 2
- 229940111134 coxibs Drugs 0.000 claims 2
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims 2
- 229940067594 flufenamate Drugs 0.000 claims 2
- LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 claims 2
- 239000003862 glucocorticoid Substances 0.000 claims 2
- 150000002343 gold Chemical class 0.000 claims 2
- 229960000905 indomethacin Drugs 0.000 claims 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 2
- 229960002009 naproxen Drugs 0.000 claims 2
- 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 claims 2
- 229960001639 penicillamine Drugs 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 150000003873 salicylate salts Chemical class 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- 210000002966 serum Anatomy 0.000 claims 2
- 201000005671 spondyloarthropathy Diseases 0.000 claims 2
- 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 claims 2
- 229940037128 systemic glucocorticoids Drugs 0.000 claims 2
- 229950006828 timegadine Drugs 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- 235000019166 vitamin D Nutrition 0.000 claims 2
- 239000011710 vitamin D Substances 0.000 claims 2
- 150000003710 vitamin D derivatives Chemical class 0.000 claims 2
- 229940046008 vitamin d Drugs 0.000 claims 2
- FHOAKXBXYSJBGX-YFKPBYRVSA-N (2s)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](CO)C(O)=O FHOAKXBXYSJBGX-YFKPBYRVSA-N 0.000 claims 1
- UAFXQPZHSYFSEA-UHFFFAOYSA-N 1-[(4-bromo-2-methylphenyl)-[3-chloro-4-(2-methylbenzoyl)phenyl]carbamoyl]oxyethyl 2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]acetate Chemical compound C=1C=C(Br)C=C(C)C=1N(C(=O)OC(C)OC(=O)COCCOCCOCCOC)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C UAFXQPZHSYFSEA-UHFFFAOYSA-N 0.000 claims 1
- KMKOVDIUQJVPNA-GHZUAHJPSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl (2s)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound C=1C=C(F)C=C(C)C=1N(C(=O)OC(OC(=O)[C@H](CO)NC(=O)OC(C)(C)C)C)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C KMKOVDIUQJVPNA-GHZUAHJPSA-N 0.000 claims 1
- GKHAJIQWJCVOPJ-UHFFFAOYSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl 2,2-dimethylpropanoate Chemical compound C=1C=C(F)C=C(C)C=1N(C(=O)OC(C)OC(=O)C(C)(C)C)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C GKHAJIQWJCVOPJ-UHFFFAOYSA-N 0.000 claims 1
- QETOLPPCQBWJME-UHFFFAOYSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl 2-hydroxy-2-methylpropanoate Chemical compound C=1C=C(F)C=C(C)C=1N(C(=O)OC(C)OC(=O)C(C)(C)O)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C QETOLPPCQBWJME-UHFFFAOYSA-N 0.000 claims 1
- KEWGQCYPMPQZTC-UHFFFAOYSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl 2-hydroxy-2-phenylacetate Chemical compound C=1C=C(C(=O)C=2C(=CC=CC=2)C)C(Cl)=CC=1N(C=1C(=CC(F)=CC=1)C)C(=O)OC(C)OC(=O)C(O)C1=CC=CC=C1 KEWGQCYPMPQZTC-UHFFFAOYSA-N 0.000 claims 1
- IMKZPLAIYNRLCG-UHFFFAOYSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl 2-methylpropanoate Chemical compound C=1C=C(F)C=C(C)C=1N(C(=O)OC(C)OC(=O)C(C)C)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C IMKZPLAIYNRLCG-UHFFFAOYSA-N 0.000 claims 1
- CFGKGZAFERKDOI-UHFFFAOYSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl 3-methoxypropanoate Chemical compound C=1C=C(F)C=C(C)C=1N(C(=O)OC(C)OC(=O)CCOC)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C CFGKGZAFERKDOI-UHFFFAOYSA-N 0.000 claims 1
- VXZWJFPXJURZFM-UHFFFAOYSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl cyclobutanecarboxylate Chemical compound C=1C=C(C(=O)C=2C(=CC=CC=2)C)C(Cl)=CC=1N(C=1C(=CC(F)=CC=1)C)C(=O)OC(C)OC(=O)C1CCC1 VXZWJFPXJURZFM-UHFFFAOYSA-N 0.000 claims 1
- FMSFSLQDXOTPOG-UHFFFAOYSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl decanoate Chemical compound C=1C=C(F)C=C(C)C=1N(C(=O)OC(C)OC(=O)CCCCCCCCC)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C FMSFSLQDXOTPOG-UHFFFAOYSA-N 0.000 claims 1
- UDUQTKGDVVZPSZ-UHFFFAOYSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl pentanoate Chemical compound C=1C=C(F)C=C(C)C=1N(C(=O)OC(C)OC(=O)CCCC)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C UDUQTKGDVVZPSZ-UHFFFAOYSA-N 0.000 claims 1
- WXQWNGMERPOYRS-UHFFFAOYSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl prop-2-enoate Chemical compound C=1C=C(F)C=C(C)C=1N(C(=O)OC(OC(=O)C=C)C)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C WXQWNGMERPOYRS-UHFFFAOYSA-N 0.000 claims 1
- AHYDTSIFNGJZID-UHFFFAOYSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl propanoate Chemical compound C=1C=C(F)C=C(C)C=1N(C(=O)OC(C)OC(=O)CC)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C AHYDTSIFNGJZID-UHFFFAOYSA-N 0.000 claims 1
- LVQYYGIPKMZCSJ-UHFFFAOYSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl pyridine-2-carboxylate Chemical compound C=1C=CC=NC=1C(=O)OC(C)OC(=O)N(C=1C(=CC(F)=CC=1)C)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C LVQYYGIPKMZCSJ-UHFFFAOYSA-N 0.000 claims 1
- BMMOGHYATYWENA-UHFFFAOYSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC(C)OC(=O)N(C=1C(=CC(F)=CC=1)C)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C BMMOGHYATYWENA-UHFFFAOYSA-N 0.000 claims 1
- WQDUTJMSUQTWLS-UHFFFAOYSA-N 1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl pyridine-4-carboxylate Chemical compound C=1C=NC=CC=1C(=O)OC(C)OC(=O)N(C=1C(=CC(F)=CC=1)C)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C WQDUTJMSUQTWLS-UHFFFAOYSA-N 0.000 claims 1
- LAMGMPZPVYQVHY-UHFFFAOYSA-N 1-[[3-chloro-4-(4-chloro-2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl butanoate Chemical compound C=1C=C(F)C=C(C)C=1N(C(=O)OC(C)OC(=O)CCC)C(C=C1Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1C LAMGMPZPVYQVHY-UHFFFAOYSA-N 0.000 claims 1
- MBYWXLCLTYNEPR-UHFFFAOYSA-N 1-o-benzyl 4-o-[1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl] butanedioate Chemical compound C=1C=C(C(=O)C=2C(=CC=CC=2)C)C(Cl)=CC=1N(C=1C(=CC(F)=CC=1)C)C(=O)OC(C)OC(=O)CCC(=O)OCC1=CC=CC=C1 MBYWXLCLTYNEPR-UHFFFAOYSA-N 0.000 claims 1
- BCGLNCAVZDQPGE-UHFFFAOYSA-N 2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]acetic acid Chemical compound COCCOCCOCCOCC(O)=O BCGLNCAVZDQPGE-UHFFFAOYSA-N 0.000 claims 1
- WTLNOANVTIKPEE-UHFFFAOYSA-N 2-acetyloxypropanoic acid Chemical compound OC(=O)C(C)OC(C)=O WTLNOANVTIKPEE-UHFFFAOYSA-N 0.000 claims 1
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 claims 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 claims 1
- HTNUUDFQRYBJPH-UHFFFAOYSA-N 3-methoxypropanehydrazide Chemical compound COCCC(=O)NN HTNUUDFQRYBJPH-UHFFFAOYSA-N 0.000 claims 1
- KTXVCRZUCZDEDN-UHFFFAOYSA-N 4-[1-[(4-bromo-2-methylphenyl)-[3-chloro-4-(2-methylbenzoyl)phenyl]carbamoyl]oxyethoxy]-4-oxobutanoic acid Chemical compound C=1C=C(Br)C=C(C)C=1N(C(=O)OC(OC(=O)CCC(O)=O)C)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C KTXVCRZUCZDEDN-UHFFFAOYSA-N 0.000 claims 1
- KZTAOEDVAMXQPV-UHFFFAOYSA-N 4-[1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethoxy]-4-oxobutanoic acid Chemical compound C=1C=C(F)C=C(C)C=1N(C(=O)OC(OC(=O)CCC(O)=O)C)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C KZTAOEDVAMXQPV-UHFFFAOYSA-N 0.000 claims 1
- VGRFOGOSWXXWHV-UHFFFAOYSA-N 4-o-[1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethyl] 1-o-ethyl butanedioate Chemical compound C=1C=C(F)C=C(C)C=1N(C(=O)OC(C)OC(=O)CCC(=O)OCC)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C VGRFOGOSWXXWHV-UHFFFAOYSA-N 0.000 claims 1
- VHJSUHLVCBWAJK-UHFFFAOYSA-N 4-o-[[(4-bromo-2-methylphenyl)-[3-chloro-4-(2-methylbenzoyl)phenyl]carbamoyl]oxymethyl] 1-o-methyl butanedioate Chemical compound C=1C=C(Br)C=C(C)C=1N(C(=O)OCOC(=O)CCC(=O)OC)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C VHJSUHLVCBWAJK-UHFFFAOYSA-N 0.000 claims 1
- RTAPDZBZLSXHQQ-UHFFFAOYSA-N 8-methyl-3,7-dihydropurine-2,6-dione Chemical class N1C(=O)NC(=O)C2=C1N=C(C)N2 RTAPDZBZLSXHQQ-UHFFFAOYSA-N 0.000 claims 1
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- GZLODLPTDPTWPQ-UHFFFAOYSA-N [[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxymethyl 2-methylpropanoate Chemical compound C=1C=C(F)C=C(C)C=1N(C(=O)OCOC(=O)C(C)C)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C GZLODLPTDPTWPQ-UHFFFAOYSA-N 0.000 claims 1
- JYMGHOPEGISIFN-UHFFFAOYSA-N [[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxymethyl 3,3-dimethylbutanoate Chemical compound CC1=CC=CC=C1C(=O)C1=CC=C(N(C(=O)OCOC(=O)CC(C)(C)C)C=2C(=CC(F)=CC=2)C)C=C1Cl JYMGHOPEGISIFN-UHFFFAOYSA-N 0.000 claims 1
- QHNKZYXTQRAMSQ-UHFFFAOYSA-N [[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxymethyl cyclopropanecarboxylate Chemical compound CC1=CC=CC=C1C(=O)C1=CC=C(N(C(=O)OCOC(=O)C2CC2)C=2C(=CC(F)=CC=2)C)C=C1Cl QHNKZYXTQRAMSQ-UHFFFAOYSA-N 0.000 claims 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- VNPNMYMREVUJEK-UHFFFAOYSA-M sodium;4-[1-[[3-chloro-4-(2-methylbenzoyl)phenyl]-(4-fluoro-2-methylphenyl)carbamoyl]oxyethoxy]-4-oxobutanoate Chemical compound [Na+].C=1C=C(F)C=C(C)C=1N(C(=O)OC(OC(=O)CCC([O-])=O)C)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C VNPNMYMREVUJEK-UHFFFAOYSA-M 0.000 claims 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 claims 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 claims 1
- 150000003751 zinc Chemical class 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 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 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 102000003810 Interleukin-18 Human genes 0.000 description 3
- 108090000171 Interleukin-18 Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000010956 selective crystallization Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- DPZHKLJPVMYFCU-UHFFFAOYSA-N 2-(5-bromopyridin-2-yl)acetonitrile Chemical compound BrC1=CC=C(CC#N)N=C1 DPZHKLJPVMYFCU-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 102000018594 Tumour necrosis factor Human genes 0.000 description 1
- 108050007852 Tumour necrosis factor Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000036576 dermal application Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- 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
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43479802P | 2002-12-20 | 2002-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200504720B true ZA200504720B (en) | 2006-08-30 |
Family
ID=32682109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200504720A ZA200504720B (en) | 2002-12-20 | 2005-06-09 | Novel aminobenzophenone compounds |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20060058380A1 (es) |
| EP (1) | EP1583735A2 (es) |
| JP (1) | JP2006510688A (es) |
| KR (1) | KR20050089056A (es) |
| CN (1) | CN1753861A (es) |
| AR (1) | AR042634A1 (es) |
| AU (1) | AU2003287917A1 (es) |
| BR (1) | BR0317445A (es) |
| CA (1) | CA2510711A1 (es) |
| IS (1) | IS7943A (es) |
| MX (1) | MXPA05006435A (es) |
| NO (1) | NO20053562L (es) |
| PL (1) | PL377377A1 (es) |
| RU (1) | RU2005122951A (es) |
| WO (1) | WO2004056762A2 (es) |
| ZA (1) | ZA200504720B (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4116671B2 (ja) * | 2004-06-28 | 2008-07-09 | インサイト コーポレイション | ケモカイン受容体の調節剤としての３−アミノシクロペンタンカルボキサミド |
| EP1763351B9 (en) * | 2004-06-28 | 2017-05-31 | Incyte Holdings Corporation | 3-aminocyclopentanecarboxamides as modulators of chemokine receptors |
| PL1828148T3 (pl) | 2004-12-13 | 2010-08-31 | Leo Pharma As | Triazol podstawiony związkami aminobenzofenonu |
| JP6925080B2 (ja) * | 2017-08-25 | 2021-08-25 | ▲広▼州市恒▲諾▼康医▲薬▼科技有限公司Ｇｕａｎｇｚｈｏｕ Ｈｅｎｏｖｃｏｍ Ｂｉｏｓｃｉｅｎｃｅ Ｃｏ．， Ｌｔｄ | 長時間作用型ラサギリンプロドラッグ、その製造方法および用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1535401A (en) * | 1977-07-28 | 1978-12-13 | Holliday & Co Ltd L | Nitrodiphenylamine carboxylic acid disperse dyes |
| GB9701453D0 (en) * | 1997-01-24 | 1997-03-12 | Leo Pharm Prod Ltd | Aminobenzophenones |
| KR20020022774A (ko) * | 1999-07-16 | 2002-03-27 | 룬딩 에른스트 | ＩＬ-1β 및 ＴＮＦ-α 억제제로서의 아미노벤조페논 |
| US6897236B1 (en) * | 1999-07-16 | 2005-05-24 | Leo Pharmaceutical Products, Ltd. | Aminobenzophenones as inhibitors of IL-1β and TNF-α |
| JP2003505361A (ja) * | 1999-07-16 | 2003-02-12 | レオ・ファーマ・アクティーゼルスカブ | ＩＬ−１βおよびＴＮＦ−αの抑制剤としてのアミノベンゾフェノン |
| RU2260422C2 (ru) * | 1999-12-06 | 2005-09-20 | Лео Фарма А/С | АМИНОБЕНЗОФЕНОНЫ КАК ИНГИБИТОРЫ ИЛ-β И ТНФ-α |
| US20020165286A1 (en) * | 2000-12-08 | 2002-11-07 | Hanne Hedeman | Dermal anti-inflammatory composition |
| AU2002338286A1 (en) * | 2001-04-10 | 2002-10-28 | Leo Pharma A/S | Novel aminophenyl ketone derivatives |
| AU2002331310B2 (en) * | 2001-08-28 | 2008-07-17 | Leo Pharma A/S | Novel aminobenzoephenones |
-
2003
- 2003-12-19 RU RU2005122951/04A patent/RU2005122951A/ru not_active Application Discontinuation
- 2003-12-19 BR BR0317445-0A patent/BR0317445A/pt not_active Application Discontinuation
- 2003-12-19 US US10/539,602 patent/US20060058380A1/en not_active Abandoned
- 2003-12-19 PL PL377377A patent/PL377377A1/pl not_active Application Discontinuation
- 2003-12-19 AU AU2003287917A patent/AU2003287917A1/en not_active Abandoned
- 2003-12-19 AR ARP030104756A patent/AR042634A1/es unknown
- 2003-12-19 JP JP2004561082A patent/JP2006510688A/ja active Pending
- 2003-12-19 EP EP03779757A patent/EP1583735A2/en not_active Withdrawn
- 2003-12-19 KR KR1020057011330A patent/KR20050089056A/ko not_active Application Discontinuation
- 2003-12-19 CA CA002510711A patent/CA2510711A1/en not_active Abandoned
- 2003-12-19 CN CNA2003801098596A patent/CN1753861A/zh active Pending
- 2003-12-19 WO PCT/DK2003/000900 patent/WO2004056762A2/en not_active Application Discontinuation
- 2003-12-19 MX MXPA05006435A patent/MXPA05006435A/es unknown
-
2005
- 2005-06-09 ZA ZA200504720A patent/ZA200504720B/en unknown
- 2005-07-18 IS IS7943A patent/IS7943A/is unknown
- 2005-07-20 NO NO20053562A patent/NO20053562L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20053562L (no) | 2005-07-20 |
| BR0317445A (pt) | 2005-11-16 |
| US20060058380A1 (en) | 2006-03-16 |
| CA2510711A1 (en) | 2004-07-08 |
| CN1753861A (zh) | 2006-03-29 |
| AR042634A1 (es) | 2005-06-29 |
| KR20050089056A (ko) | 2005-09-07 |
| WO2004056762A2 (en) | 2004-07-08 |
| EP1583735A2 (en) | 2005-10-12 |
| JP2006510688A (ja) | 2006-03-30 |
| AU2003287917A1 (en) | 2004-07-14 |
| WO2004056762A3 (en) | 2004-08-12 |
| IS7943A (is) | 2005-07-18 |
| PL377377A1 (pl) | 2006-02-06 |
| RU2005122951A (ru) | 2006-01-27 |
| MXPA05006435A (es) | 2005-09-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6049931B2 (ja) | Ｐ２ｙ１２受容体のシクロプロピルモジュレーター | |
| ES2393230T3 (es) | Uso farmacéutico de amidas sustituidas | |
| EP2617714B1 (en) | Chemical derivatives of jasmonate, pharmaceutical compositions and methods of use thereof | |
| US20050267170A1 (en) | Substituted methyl aryl or heteroaryl amide compounds | |
| KR20150102069A (ko) | 치환된 스피로피리도[1,2-a]피라진 유도체 및 그의 HIV 인테그라제 저해제로서의 의약 용도 | |
| JP2017518959A5 (es) | ||
| KR20150013527A (ko) | 항염증 활성과 접합된 증진된 항인플루엔자제 | |
| RU2010149611A (ru) | Ациламинозамещенные производные конденсированных циклопентанкарбоновых кислот и их применение в качестве фармацевтических средств | |
| JP2016506387A (ja) | Ｈｂｖ感染に対する抗ウイルス剤としての官能化ベンズアミド誘導体 | |
| KR20110055735A (ko) | 박테리아 감염 치료에 적용하기 위한 유기 화합물 | |
| EA011167B1 (ru) | Производные сульфонамида для лечения заболеваний | |
| US11197864B2 (en) | Pro-drugs of riluzole and their method of use for the treatment of amyotrophic lateral sclerosis | |
| ZA200504720B (en) | Novel aminobenzophenone compounds | |
| US20150216830A1 (en) | 5-aminolevulinic acid derivatives, methods for their preparation and uses thereof | |
| US20160297789A1 (en) | Indanone derivatives, pharmaceutically acceptable salts or optical isomers thereof, preparation method for same, and pharmaceutical compositions containing same as active ingredient for preventing or treating viral diseases | |
| CA2958040C (en) | Process for preparing synthetic intermediates for preparing tetrahydroquinoline derivatives | |
| WO2007067817A1 (en) | Abca1 elevating compounds | |
| ES2642172T3 (es) | Compuestos derivados de ciclohexeno sustituidos con biarilo o biarilo heterocíclico como inhibidores de CETP | |
| CN113767104B (zh) | 双功能化合物及其使用方法 | |
| WO2002059074A1 (fr) | Analogue de benzylamine | |
| JP2011503030A (ja) | 神経因性疼痛に活性な薬物 | |
| KR100764885B1 (ko) | 포스포디에스테라제 ｉｖ 억제 활성을 갖는 약제의 제조에유용한 화합물 | |
| JP2005500400A (ja) | 新規アミノベンゾフェノン | |
| TW201414707A (zh) | ３，５，ｎ－三羥烷醯胺及其衍生物、其之製造方法與用途 | |
| US20220324862A1 (en) | Pyridopyrimidinone compounds |