CA2141214A1 - Hydroxamic acid derivatives and their use as anti-inflammatory compounds - Google Patents
Hydroxamic acid derivatives and their use as anti-inflammatory compoundsInfo
- Publication number
- CA2141214A1 CA2141214A1 CA002141214A CA2141214A CA2141214A1 CA 2141214 A1 CA2141214 A1 CA 2141214A1 CA 002141214 A CA002141214 A CA 002141214A CA 2141214 A CA2141214 A CA 2141214A CA 2141214 A1 CA2141214 A1 CA 2141214A1
- Authority
- CA
- Canada
- Prior art keywords
- enyl
- methylprop
- phenyl
- cyanophenoxy
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 102
- 239000002253 acid Substances 0.000 title claims abstract description 48
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title abstract description 5
- 230000003110 anti-inflammatory effect Effects 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 22
- 102000003820 Lipoxygenases Human genes 0.000 claims abstract description 10
- 108090000128 Lipoxygenases Proteins 0.000 claims abstract description 10
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims abstract description 9
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims abstract description 9
- 230000037353 metabolic pathway Effects 0.000 claims abstract description 9
- 239000003112 inhibitor Substances 0.000 claims abstract description 7
- 230000001404 mediated effect Effects 0.000 claims abstract description 5
- 238000013160 medical therapy Methods 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 238000011282 treatment Methods 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims description 55
- 239000012453 solvate Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- -1 (E)-1-{3-[3-(4-cyanophenoxy)phenyl]-1(S)-methylprop-2-enyl}-1-hydroxyurea Chemical compound 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 238000011321 prophylaxis Methods 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 239000004615 ingredient Substances 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- GYIBHQYKZQRMCE-DUXPYHPUSA-N 1-[(e)-3-[3-(4-cyanophenoxy)phenyl]prop-2-enyl]-1-hydroxyurea Chemical compound NC(=O)N(O)C\C=C\C1=CC=CC(OC=2C=CC(=CC=2)C#N)=C1 GYIBHQYKZQRMCE-DUXPYHPUSA-N 0.000 claims description 2
- IRUNSIONMWMUDR-ZHACJKMWSA-N 1-[(e)-4-(2-cyano-3-phenoxyphenyl)but-3-en-2-yl]-1-hydroxyurea Chemical compound NC(=O)N(O)C(C)\C=C\C1=CC=CC(OC=2C=CC=CC=2)=C1C#N IRUNSIONMWMUDR-ZHACJKMWSA-N 0.000 claims description 2
- XOHOMZCMHBRTFN-GORDUTHDSA-N 1-[(e)-4-[2-cyano-5-(4-cyanophenoxy)phenyl]but-3-en-2-yl]-1-hydroxyurea Chemical compound C1=C(C#N)C(/C=C/C(C)N(O)C(N)=O)=CC(OC=2C=CC(=CC=2)C#N)=C1 XOHOMZCMHBRTFN-GORDUTHDSA-N 0.000 claims description 2
- MZNSQHCCOZZULH-NSCUHMNNSA-N 1-[(e)-4-[4-cyano-3-(4-fluorophenoxy)phenyl]but-3-en-2-yl]-1-hydroxyurea Chemical compound NC(=O)N(O)C(C)\C=C\C1=CC=C(C#N)C(OC=2C=CC(F)=CC=2)=C1 MZNSQHCCOZZULH-NSCUHMNNSA-N 0.000 claims description 2
- BJERONYTRXGCNL-VOTSOKGWSA-N 1-hydroxy-1-[(e)-4-[3-(4-methylsulfonylphenoxy)phenyl]but-3-en-2-yl]urea Chemical compound NC(=O)N(O)C(C)\C=C\C1=CC=CC(OC=2C=CC(=CC=2)S(C)(=O)=O)=C1 BJERONYTRXGCNL-VOTSOKGWSA-N 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- UXRLAGGKUZEKSK-VOTSOKGWSA-N n-[(e)-4-[3-(4-cyanophenoxy)phenyl]but-3-en-2-yl]-n-hydroxyacetamide Chemical compound CC(=O)N(O)C(C)\C=C\C1=CC=CC(OC=2C=CC(=CC=2)C#N)=C1 UXRLAGGKUZEKSK-VOTSOKGWSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 12
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- TXLPREYNNCJXKJ-AATRIKPKSA-N 1-[(e)-4-[3-(4-cyanophenoxy)phenyl]but-3-en-2-yl]-1-hydroxyurea Chemical compound NC(=O)N(O)C(C)\C=C\C1=CC=CC(OC=2C=CC(=CC=2)C#N)=C1 TXLPREYNNCJXKJ-AATRIKPKSA-N 0.000 claims 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
- UXRLAGGKUZEKSK-UZYOAWRESA-N n-[(e,2s)-4-[3-(4-cyanophenoxy)phenyl]but-3-en-2-yl]-n-hydroxyacetamide Chemical compound CC(=O)N(O)[C@@H](C)\C=C\C1=CC=CC(OC=2C=CC(=CC=2)C#N)=C1 UXRLAGGKUZEKSK-UZYOAWRESA-N 0.000 claims 2
- IBUMSVYHJPONCX-OQHXTRMZSA-N 1-[(E,2R)-4-[2-cyano-3-(4-cyanophenoxy)phenyl]but-3-en-2-yl]-1-hydroxyurea Chemical compound C(#N)C1=CC=C(OC=2C(=C(C=CC2)/C=C/[C@@H](C)N(C(=O)N)O)C#N)C=C1 IBUMSVYHJPONCX-OQHXTRMZSA-N 0.000 claims 1
- TXLPREYNNCJXKJ-URWSZGRFSA-N 1-[(E,2R)-4-[3-(4-cyanophenoxy)phenyl]but-3-en-2-yl]-1-hydroxyurea Chemical compound C(#N)C1=CC=C(OC=2C=C(C=CC2)/C=C/[C@@H](C)N(C(=O)N)O)C=C1 TXLPREYNNCJXKJ-URWSZGRFSA-N 0.000 claims 1
- KYMUUIMLFIYBIO-BQYQJAHWSA-N 1-[(e)-4-(2-cyano-5-phenoxyphenyl)but-3-en-2-yl]-1-hydroxyurea Chemical compound C1=C(C#N)C(/C=C/C(C)N(O)C(N)=O)=CC(OC=2C=CC=CC=2)=C1 KYMUUIMLFIYBIO-BQYQJAHWSA-N 0.000 claims 1
- MWZIKCDZYVMUQC-BQYQJAHWSA-N 1-[(e)-4-(4-cyano-3-phenoxyphenyl)but-3-en-2-yl]-1-hydroxyurea Chemical compound NC(=O)N(O)C(C)\C=C\C1=CC=C(C#N)C(OC=2C=CC=CC=2)=C1 MWZIKCDZYVMUQC-BQYQJAHWSA-N 0.000 claims 1
- IBUMSVYHJPONCX-VMPITWQZSA-N 1-[(e)-4-[2-cyano-3-(4-cyanophenoxy)phenyl]but-3-en-2-yl]-1-hydroxyurea Chemical compound NC(=O)N(O)C(C)\C=C\C1=CC=CC(OC=2C=CC(=CC=2)C#N)=C1C#N IBUMSVYHJPONCX-VMPITWQZSA-N 0.000 claims 1
- JSASFCKDSBYTPF-AATRIKPKSA-N 1-[(e)-4-[2-cyano-3-(4-fluorophenoxy)phenyl]but-3-en-2-yl]-1-hydroxyurea Chemical compound NC(=O)N(O)C(C)\C=C\C1=CC=CC(OC=2C=CC(F)=CC=2)=C1C#N JSASFCKDSBYTPF-AATRIKPKSA-N 0.000 claims 1
- ADKISVGOCSVEIB-NSCUHMNNSA-N 1-[(e)-4-[2-cyano-5-(4-fluorophenoxy)phenyl]but-3-en-2-yl]-1-hydroxyurea Chemical compound C1=C(C#N)C(/C=C/C(C)N(O)C(N)=O)=CC(OC=2C=CC(F)=CC=2)=C1 ADKISVGOCSVEIB-NSCUHMNNSA-N 0.000 claims 1
- MXBSQWJPXRYAGO-GFUIURDCSA-N 4-[3-[(e,3s)-3-(hydroxyamino)but-1-enyl]phenoxy]benzonitrile Chemical compound ON[C@@H](C)\C=C\C1=CC=CC(OC=2C=CC(=CC=2)C#N)=C1 MXBSQWJPXRYAGO-GFUIURDCSA-N 0.000 claims 1
- JAEFTQFGBFZWMP-DHQBOWJTSA-N C1(=CC=C(C=C1)S(=O)(=O)[O-])C.C(#N)C1=CC=C(OC=2C=C(C=CC2)/C=C/[C@@H](C)[NH2+]O)C=C1 Chemical compound C1(=CC=C(C=C1)S(=O)(=O)[O-])C.C(#N)C1=CC=C(OC=2C=C(C=CC2)/C=C/[C@@H](C)[NH2+]O)C=C1 JAEFTQFGBFZWMP-DHQBOWJTSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- JAEFTQFGBFZWMP-IPZCTEOASA-N [(e)-4-[3-(4-cyanophenoxy)phenyl]but-3-en-2-yl]-hydroxyazanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.O[NH2+]C(C)\C=C\C1=CC=CC(OC=2C=CC(=CC=2)C#N)=C1 JAEFTQFGBFZWMP-IPZCTEOASA-N 0.000 claims 1
- JAEFTQFGBFZWMP-YFYMOGAWSA-N [(e,2s)-4-[3-(4-cyanophenoxy)phenyl]but-3-en-2-yl]-hydroxyazanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.O[NH2+][C@@H](C)\C=C\C1=CC=CC(OC=2C=CC(=CC=2)C#N)=C1 JAEFTQFGBFZWMP-YFYMOGAWSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- UXRLAGGKUZEKSK-PSKZRQQASA-N n-[(e,2r)-4-[3-(4-cyanophenoxy)phenyl]but-3-en-2-yl]-n-hydroxyacetamide Chemical compound CC(=O)N(O)[C@H](C)\C=C\C1=CC=CC(OC=2C=CC(=CC=2)C#N)=C1 UXRLAGGKUZEKSK-PSKZRQQASA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 239000000203 mixture Substances 0.000 description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 40
- 239000000047 product Substances 0.000 description 40
- 239000004480 active ingredient Substances 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 229910001868 water Inorganic materials 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 23
- 238000009472 formulation Methods 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- 239000000843 powder Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 241000282320 Panthera leo Species 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 238000004452 microanalysis Methods 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- 208000010668 atopic eczema Diseases 0.000 description 7
- 210000001772 blood platelet Anatomy 0.000 description 7
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000000172 allergic effect Effects 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 230000000699 topical effect Effects 0.000 description 6
- 206010027654 Allergic conditions Diseases 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 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 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- 229940080313 sodium starch Drugs 0.000 description 5
- 230000003033 spasmogenic effect Effects 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 4
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 229940069328 povidone Drugs 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 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
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 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 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
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- 239000003963 antioxidant agent Substances 0.000 description 3
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- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 230000004663 cell proliferation Effects 0.000 description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000013355 food flavoring agent Nutrition 0.000 description 3
- 150000005826 halohydrocarbons Chemical class 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000002685 pulmonary effect Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 210000002460 smooth muscle Anatomy 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 2
- FICQFRCPSFCFBY-UHFFFAOYSA-N 2-[bis(methylsulfanyl)methylidene]propanedinitrile Chemical compound CSC(SC)=C(C#N)C#N FICQFRCPSFCFBY-UHFFFAOYSA-N 0.000 description 2
- HIYAVKIYRIFSCZ-CYEMHPAKSA-N 5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid Chemical compound O=C([C@@H](C)[C@H]1O[C@@]2([C@@H](C[C@H]1C)C)O[C@@H]([C@@H](CC2)C)CC=1OC2=CC=C(C(=C2N=1)C(O)=O)NC)C1=CC=CN1 HIYAVKIYRIFSCZ-CYEMHPAKSA-N 0.000 description 2
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229940122204 Cyclooxygenase inhibitor Drugs 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Nutrition Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929215921A GB9215921D0 (en) | 1992-07-27 | 1992-07-27 | Anti-inflammatory compounds |
| GB9215921.9 | 1992-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2141214A1 true CA2141214A1 (en) | 1994-02-03 |
Family
ID=10719360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002141214A Abandoned CA2141214A1 (en) | 1992-07-27 | 1993-07-27 | Hydroxamic acid derivatives and their use as anti-inflammatory compounds |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0652864A1 (forum.php) |
| JP (1) | JPH07509462A (forum.php) |
| AU (1) | AU672810B2 (forum.php) |
| CA (1) | CA2141214A1 (forum.php) |
| GB (1) | GB9215921D0 (forum.php) |
| IL (1) | IL106472A0 (forum.php) |
| MX (1) | MX9304503A (forum.php) |
| TW (1) | TW246670B (forum.php) |
| WO (1) | WO1994002448A1 (forum.php) |
| ZA (1) | ZA935378B (forum.php) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2802547B2 (ja) * | 1993-11-26 | 1998-09-24 | ファイザー・インク． | 抗炎症剤としてのイソキサゾリン化合物 |
| US5696141A (en) * | 1994-03-09 | 1997-12-09 | Pfizer Inc. | Isoxazoline compounds as 5-lipoxygenase inhibitors |
| JP3322885B2 (ja) * | 1995-02-02 | 2002-09-09 | 日研化学株式会社 | Ｎ−ヒドロキシウレア誘導体 |
| JP2000504723A (ja) | 1996-02-13 | 2000-04-18 | ジー．ディー．サール アンド カンパニー | シクロオキシゲナーゼ―２阻害剤および５―リポキシゲナーゼ阻害剤投与の免疫抑制効果 |
| PT880363E (pt) | 1996-02-13 | 2002-12-31 | Searle & Co | Combinacoes com efeitos imunossupressores cntendo um inibidor da ciclooxigenase-2 e um inibidor da hidrolase do leucotrieno a4 |
| DE69733338T2 (de) | 1996-02-13 | 2006-03-16 | G.D. Searle & Co., Chicago | Zubereitungen, enthaltend einen cyclooxygenase-2-inhibitor und einen leukotrien-b4-rezeptor-antagonisten |
| DK0912184T3 (da) * | 1996-06-25 | 2002-11-25 | Cephalon Inc | Anvendelse af K-252a-derivat til behandlingen af perifere eller centrale nervelidelser og cytokinoverproduktion |
| AU758870B2 (en) * | 1997-07-31 | 2003-04-03 | Abbott Laboratories | Reverse hydroxamate inhibitors of matrix metalloproteinases |
| US6294573B1 (en) | 1997-08-06 | 2001-09-25 | Abbott Laboratories | Reverse hydroxamate inhibitors of matrix metalloproteinases |
| US6235786B1 (en) | 1997-08-06 | 2001-05-22 | Abbott Laboratories | Reverse hydroxamate inhibitors of matrix metalloproteinases |
| US6288261B1 (en) | 1998-12-18 | 2001-09-11 | Abbott Laboratories | Inhibitors of matrix metalloproteinases |
| WO2000044712A1 (en) * | 1999-01-27 | 2000-08-03 | Abbott Laboratories | N-hydroxyformamide derivatives as inhibitors of matrix metalloproteinases |
| SE0103325D0 (sv) | 2001-10-04 | 2001-10-04 | Astrazeneca Ab | Novel compounds |
| TW200946105A (en) | 2008-02-07 | 2009-11-16 | Kyorin Seiyaku Kk | Therapeutic agent or preventive agent for inflammatory bowel disease containing amino alcohol derivative as active ingredient |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0196184B1 (en) * | 1985-03-16 | 1992-09-16 | The Wellcome Foundation Limited | Aryl derivatives |
| PL154186B1 (en) * | 1987-07-15 | 1991-07-31 | Wellcome Found | Method for manufacturing arylic derivatives of the hydroxamic acid |
| ATE144247T1 (de) * | 1990-07-25 | 1996-11-15 | Abbott Lab | Acetylenderivate mit lipoxygenase inhibitorischer wirkung |
| JPH06256285A (ja) * | 1990-12-11 | 1994-09-13 | Pfizer Pharmaceut Co Ltd | ヒドロキサム酸誘導体およびその用途 |
-
1992
- 1992-07-27 GB GB929215921A patent/GB9215921D0/en active Pending
-
1993
- 1993-07-26 TW TW082105933A patent/TW246670B/zh active
- 1993-07-26 ZA ZA935378A patent/ZA935378B/xx unknown
- 1993-07-26 MX MX9304503A patent/MX9304503A/es unknown
- 1993-07-26 IL IL106472A patent/IL106472A0/xx unknown
- 1993-07-27 JP JP6504325A patent/JPH07509462A/ja active Pending
- 1993-07-27 AU AU47170/93A patent/AU672810B2/en not_active Ceased
- 1993-07-27 EP EP93917925A patent/EP0652864A1/en not_active Withdrawn
- 1993-07-27 WO PCT/GB1993/001585 patent/WO1994002448A1/en not_active Application Discontinuation
- 1993-07-27 CA CA002141214A patent/CA2141214A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| TW246670B (forum.php) | 1995-05-01 |
| JPH07509462A (ja) | 1995-10-19 |
| IL106472A0 (en) | 1993-11-15 |
| EP0652864A1 (en) | 1995-05-17 |
| GB9215921D0 (en) | 1992-09-09 |
| WO1994002448A1 (en) | 1994-02-03 |
| AU672810B2 (en) | 1996-10-17 |
| MX9304503A (es) | 1994-04-29 |
| ZA935378B (en) | 1995-01-26 |
| AU4717093A (en) | 1994-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |