SK1362000A3 - Aryloxyarylsulfonylamino hydroxamic acid derivatives - Google Patents

Aryloxyarylsulfonylamino hydroxamic acid derivatives Download PDF

Info

Publication number: SK1362000A3
Authority: SK; Slovakia
Prior art keywords: compound; amino; fluorophenoxy; compound according; benzenesulfonyl
Prior art date: 1997-08-08

Application number

SK136-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Ralph Pelton Robinson

Original Assignee

Pfizer Prod Inc

Priority date (The priority date 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 date listed.)

1997-08-08

Filing date

1998-07-21

Publication date

2000-10-09

1998-07-21 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2000-10-09 Publication of SK1362000A3 publication Critical patent/SK1362000A3/sk

Links

239000002253 acid Substances 0.000 title description 21
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 description 3
150000001875 compounds Chemical class 0.000 claims abstract description 73
150000003839 salts Chemical class 0.000 claims abstract description 35
-1 trifluoromethoxy, difluoromethoxy Chemical group 0.000 claims abstract description 32
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
239000001257 hydrogen Substances 0.000 claims abstract description 25
150000002431 hydrogen Chemical class 0.000 claims abstract description 14
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 11
229910052799 carbon Inorganic materials 0.000 claims abstract description 10
125000001424 substituent group Chemical group 0.000 claims abstract description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 3
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims abstract description 3
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 11
108010076503 Matrix Metalloproteinase 13 Proteins 0.000 claims description 10
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 10
238000000034 method Methods 0.000 claims description 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
206010028980 Neoplasm Diseases 0.000 claims description 6
206010003246 arthritis Diseases 0.000 claims description 6
230000005764 inhibitory process Effects 0.000 claims description 6
235000019260 propionic acid Nutrition 0.000 claims description 6
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 6
201000011510 cancer Diseases 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
230000000694 effects Effects 0.000 claims description 5
VHHGUBHZBLPTKL-UHFFFAOYSA-N Cp-471358 Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(CCC(O)=O)C1(C(=O)NO)CCCC1 VHHGUBHZBLPTKL-UHFFFAOYSA-N 0.000 claims description 4
LLMCVPDKPNDQCK-UHFFFAOYSA-N ethyl 3-[[4-(4-fluorophenoxy)phenyl]sulfonyl-[1-(hydroxycarbamoyl)cyclopentyl]amino]propanoate Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(CCC(=O)OCC)C1(C(=O)NO)CCCC1 LLMCVPDKPNDQCK-UHFFFAOYSA-N 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
NMDUJEUWNLCXSB-UHFFFAOYSA-N 3-[[4-(4-fluorophenoxy)phenyl]sulfonyl-[1-(hydroxyamino)-2-methyl-1-oxopropan-2-yl]amino]propanoic acid Chemical compound C1=CC(S(=O)(=O)N(CCC(O)=O)C(C)(C)C(=O)NO)=CC=C1OC1=CC=C(F)C=C1 NMDUJEUWNLCXSB-UHFFFAOYSA-N 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 2
102000011722 Matrix Metalloproteinase 13 Human genes 0.000 claims 4
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
102100027995 Collagenase 3 Human genes 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
239000003112 inhibitor Substances 0.000 description 13
239000000203 mixture Substances 0.000 description 13
102000029816 Collagenase Human genes 0.000 description 12
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
229960002424 collagenase Drugs 0.000 description 12
239000002585 base Substances 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
102000004190 Enzymes Human genes 0.000 description 7
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102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 7
108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
239000012267 brine Substances 0.000 description 7
229940088598 enzyme Drugs 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000000758 substrate Substances 0.000 description 7
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001447 alkali salts Chemical class 0.000 description 6
238000003556 assay Methods 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
231100000252 nontoxic Toxicity 0.000 description 6
230000003000 nontoxic effect Effects 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000000651 prodrug Substances 0.000 description 6
229940002612 prodrug Drugs 0.000 description 6
108060008682 Tumor Necrosis Factor Proteins 0.000 description 5
208000025865 Ulcer Diseases 0.000 description 5
239000002798 polar solvent Substances 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
102000003390 tumor necrosis factor Human genes 0.000 description 5
230000036269 ulceration Effects 0.000 description 5
108050005238 Collagenase 3 Proteins 0.000 description 4
101000577887 Homo sapiens Collagenase 3 Proteins 0.000 description 4
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 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
102000004142 Trypsin Human genes 0.000 description 4
108090000631 Trypsin Proteins 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
125000000539 amino acid group Chemical group 0.000 description 4
150000007514 bases Chemical class 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
208000028169 periodontal disease Diseases 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
239000012588 trypsin Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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201000001320 Atherosclerosis Diseases 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
206010053177 Epidermolysis Diseases 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
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230000033115 angiogenesis Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
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239000007943 implant Substances 0.000 description 3
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
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208000037803 restenosis Diseases 0.000 description 3
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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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
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
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CUQBVKOADUOKPT-UHFFFAOYSA-N benzyl 1-[(3-ethoxy-3-oxopropyl)-[4-(4-fluorophenoxy)phenyl]sulfonylamino]cyclopentane-1-carboxylate Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(CCC(=O)OCC)C1(C(=O)OCC=2C=CC=CC=2)CCCC1 CUQBVKOADUOKPT-UHFFFAOYSA-N 0.000 description 2
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ICKPCMLGESBARJ-UHFFFAOYSA-N benzyl 1-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]cyclopentane-1-carboxylate Chemical compound C1=CC(F)=CC=C1OC1=CC=C(S(=O)(=O)NC2(CCCC2)C(=O)OCC=2C=CC=CC=2)C=C1 ICKPCMLGESBARJ-UHFFFAOYSA-N 0.000 description 2
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
230000024279 bone resorption Effects 0.000 description 2
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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 2
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentane carboxylic acid Natural products OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
229910052805 deuterium Inorganic materials 0.000 description 2
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QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
229960002591 hydroxyproline Drugs 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
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230000009545 invasion Effects 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
208000002780 macular degeneration Diseases 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
208000027202 mammary Paget disease Diseases 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229960003194 meglumine Drugs 0.000 description 1
238000002844 melting Methods 0.000 description 1
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239000012528 membrane Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
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229940098779 methanesulfonic acid Drugs 0.000 description 1
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125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical compound ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
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239000007800 oxidant agent Substances 0.000 description 1
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239000000312 peanut oil Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001184 polypeptide Chemical group 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000002265 prevention Effects 0.000 description 1
108090000765 processed proteins & peptides Chemical group 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
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239000000523 sample Substances 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 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
229960001790 sodium citrate Drugs 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
108091007196 stromelysin Proteins 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
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239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
KTJOZDBANQOLHP-UHFFFAOYSA-N tert-butyl-(3-iodopropoxy)-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCCI KTJOZDBANQOLHP-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
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DRDCQJADRSJFFD-UHFFFAOYSA-N tris-hydroxymethyl-methyl-ammonium Chemical class OC[N+](C)(CO)CO DRDCQJADRSJFFD-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000002753 trypsin inhibitor Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
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239000011592 zinc chloride Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- 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
- A61P19/00—Drugs for skeletal disorders
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/14—Nitrogen atoms not forming part of a nitro radical

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Surgery (AREA)
Immunology (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)
Hydrogenated Pyridines (AREA)
Pyrane Compounds (AREA)

SK136-2000A 1997-08-08 1998-07-21 Aryloxyarylsulfonylamino hydroxamic acid derivatives SK1362000A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5520797P	1997-08-08	1997-08-08
PCT/IB1998/001113 WO1999007675A1 (fr)	1997-08-08	1998-07-21	Derives de l'acide aryloxyarylsulfonylamino hydroxamique

Publications (1)

Publication Number	Publication Date
SK1362000A3 true SK1362000A3 (en)	2000-10-09

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ID=21996358

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK136-2000A SK1362000A3 (en)	1997-08-08	1998-07-21	Aryloxyarylsulfonylamino hydroxamic acid derivatives

Country Status (42)

Country	Link
US (1)	US6214872B1 (fr)
EP (1)	EP1003720B1 (fr)
JP (1)	JP3448275B2 (fr)
KR (1)	KR100372138B1 (fr)
CN (1)	CN1171866C (fr)
AP (1)	AP1220A (fr)
AR (1)	AR015419A1 (fr)
AT (1)	ATE263147T1 (fr)
AU (1)	AU730248B2 (fr)
BG (1)	BG104118A (fr)
BR (1)	BR9811868A (fr)
CA (1)	CA2299355C (fr)
CO (1)	CO4960658A1 (fr)
DE (1)	DE69822839T2 (fr)
DK (1)	DK1003720T3 (fr)
DZ (1)	DZ2581A1 (fr)
EA (1)	EA002490B1 (fr)
ES (1)	ES2216293T3 (fr)
GT (1)	GT199800124A (fr)
HR (1)	HRP980438B1 (fr)
HU (1)	HUP0002960A3 (fr)
ID (1)	ID23668A (fr)
IL (1)	IL134300A (fr)
IS (1)	IS5340A (fr)
MA (1)	MA26530A1 (fr)
MY (1)	MY120235A (fr)
NO (1)	NO313189B1 (fr)
NZ (1)	NZ502309A (fr)
OA (1)	OA11284A (fr)
PA (1)	PA8456801A1 (fr)
PE (1)	PE110899A1 (fr)
PL (1)	PL338633A1 (fr)
PT (1)	PT1003720E (fr)
SK (1)	SK1362000A3 (fr)
TN (1)	TNSN98150A1 (fr)
TR (1)	TR200000368T2 (fr)
TW (1)	TW426662B (fr)
UA (1)	UA61963C2 (fr)
UY (2)	UY25131A1 (fr)
WO (1)	WO1999007675A1 (fr)
YU (1)	YU1900A (fr)
ZA (1)	ZA987126B (fr)

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1998
- 1998-07-21 US US09/380,163 patent/US6214872B1/en not_active Expired - Fee Related
- 1998-07-21 CA CA002299355A patent/CA2299355C/fr not_active Expired - Fee Related
- 1998-07-21 EA EA200000096A patent/EA002490B1/ru not_active IP Right Cessation
- 1998-07-21 KR KR10-2000-7001303A patent/KR100372138B1/ko not_active Expired - Fee Related
- 1998-07-21 IL IL13430098A patent/IL134300A/en not_active IP Right Cessation
- 1998-07-21 AU AU81253/98A patent/AU730248B2/en not_active Ceased
- 1998-07-21 JP JP2000506179A patent/JP3448275B2/ja not_active Expired - Fee Related
- 1998-07-21 AT AT98930987T patent/ATE263147T1/de not_active IP Right Cessation
- 1998-07-21 WO PCT/IB1998/001113 patent/WO1999007675A1/fr not_active Ceased
- 1998-07-21 SK SK136-2000A patent/SK1362000A3/sk unknown
- 1998-07-21 YU YU1900A patent/YU1900A/sh unknown
- 1998-07-21 ID IDW20000232A patent/ID23668A/id unknown
- 1998-07-21 UA UA2000020651A patent/UA61963C2/uk unknown
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- 1998-07-21 DE DE69822839T patent/DE69822839T2/de not_active Expired - Fee Related
- 1998-07-21 CN CNB988078961A patent/CN1171866C/zh not_active Expired - Fee Related
- 1998-07-21 BR BR9811868-4A patent/BR9811868A/pt not_active Application Discontinuation
- 1998-07-21 PL PL98338633A patent/PL338633A1/xx unknown
- 1998-07-21 ES ES98930987T patent/ES2216293T3/es not_active Expired - Lifetime
- 1998-07-21 EP EP98930987A patent/EP1003720B1/fr not_active Expired - Lifetime
- 1998-07-21 PT PT98930987T patent/PT1003720E/pt unknown
- 1998-07-21 DK DK98930987T patent/DK1003720T3/da active
- 1998-07-21 TR TR2000/00368T patent/TR200000368T2/xx unknown
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- 1998-08-04 PE PE1998000696A patent/PE110899A1/es not_active Application Discontinuation
- 1998-08-05 DZ DZ980191A patent/DZ2581A1/fr active
- 1998-08-05 TW TW087112896A patent/TW426662B/zh not_active IP Right Cessation
- 1998-08-05 PA PA19988456801A patent/PA8456801A1/es unknown
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- 1998-08-07 HR HR980438A patent/HRP980438B1/xx not_active IP Right Cessation
- 1998-08-07 MA MA25207A patent/MA26530A1/fr unknown
- 1998-08-07 AR ARP980103929A patent/AR015419A1/es unknown
- 1998-08-07 ZA ZA9807126A patent/ZA987126B/xx unknown
- 1998-08-07 TN TNTNSN98150A patent/TNSN98150A1/fr unknown
- 1998-08-07 GT GT199800124A patent/GT199800124A/es unknown
- 1998-08-10 UY UY25131A patent/UY25131A1/es not_active IP Right Cessation
2000
- 2000-01-14 IS IS5340A patent/IS5340A/is unknown
- 2000-02-01 BG BG104118A patent/BG104118A/bg unknown
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- 2000-02-07 NO NO20000604A patent/NO313189B1/no not_active IP Right Cessation
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Also Published As

Publication number	Publication date
KR100372138B1 (ko)	2003-02-14
DZ2581A1 (fr)	2003-02-22
EP1003720B1 (fr)	2004-03-31
NZ502309A (en)	2002-02-01
CA2299355C (fr)	2005-09-27
PA8456801A1 (es)	2000-05-24
HUP0002960A3 (en)	2001-12-28
HRP980438A2 (en)	1999-12-31
NO20000604L (no)	2000-02-07
HRP980438B1 (en)	2003-04-30
CO4960658A1 (es)	2000-09-25
CN1171866C (zh)	2004-10-20
CA2299355A1 (fr)	1999-02-18
AU8125398A (en)	1999-03-01
IL134300A (en)	2004-07-25
UA61963C2 (en)	2003-12-15
OA11284A (en)	2003-07-30
US6214872B1 (en)	2001-04-10
YU1900A (sh)	2002-08-12
MY120235A (en)	2005-09-30
UY26098A1 (es)	2001-12-28
DE69822839D1 (de)	2004-05-06
GT199800124A (es)	2000-01-29
AU730248B2 (en)	2001-03-01
BR9811868A (pt)	2000-08-15
AR015419A1 (es)	2001-05-02
IS5340A (is)	2000-01-14
TR200000368T2 (tr)	2000-07-21
KR20010022707A (ko)	2001-03-26
PE110899A1 (es)	1999-11-12
NO313189B1 (no)	2002-08-26
HK1029575A1 (en)	2001-04-06
JP2001512713A (ja)	2001-08-28
DE69822839T2 (de)	2004-08-19
JP3448275B2 (ja)	2003-09-22
UY25131A1 (es)	2000-12-29
MA26530A1 (fr)	2004-12-20
ID23668A (id)	2000-05-11
TW426662B (en)	2001-03-21
AP9801313A0 (en)	1998-09-30
AP1220A (en)	2003-10-24
PL338633A1 (en)	2000-11-06
CN1265646A (zh)	2000-09-06
BG104118A (bg)	2000-09-29
EA002490B1 (ru)	2002-06-27
ZA987126B (en)	2000-02-07
PT1003720E (pt)	2004-07-30
IL134300A0 (en)	2001-04-30
HUP0002960A2 (hu)	2001-07-30
TNSN98150A1 (fr)	2005-03-15
EP1003720A1 (fr)	2000-05-31
DK1003720T3 (da)	2004-05-10
NO20000604D0 (no)	2000-02-07
ATE263147T1 (de)	2004-04-15
EA200000096A1 (ru)	2000-10-30
WO1999007675A1 (fr)	1999-02-18
ES2216293T3 (es)	2004-10-16

Publication	Publication Date	Title
SK1362000A3 (en)	2000-10-09	Aryloxyarylsulfonylamino hydroxamic acid derivatives
AP733A (en)	1999-02-12	Arylsulfonylamino hydroxamic acid derivatives.
AP826A (en)	2000-04-28	Arysulfonylamino hydroxamic acid derivatives.
CA2268484C (fr)	2006-02-07	Derives d'acide hydroxamique aryloxyarylsulfonylamino de cyclobutyle
DE69912379T2 (de)	2004-05-06	Antithrombosemittel
WO1998034915A1 (fr)	1998-08-13	Derives du n-hxdroxy-beta-sulfonyl-propionamide et leur utilisation comme inhibiteurs des metalloproteases matrices
EP0895988B1 (fr)	2002-05-22	Dérivés de l'acide arylsulfonamino-hydroxamique
US6300337B1 (en)	2001-10-09	Acetamide derivative and use thereof
IL314855A (en)	2024-10-01	Preparation method of nitrogen-containing heterocyclic compound
DE69907337T2 (de)	2004-02-26	Hydroxamsäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammenstellungen
CZ2000306A3 (cs)	2000-07-12	Deriváty aryloxyarylsulfonylaminohydroxamové kyseliny
EP1415984A1 (fr)	2004-05-06	Dérivés de l'acide aryloxyarylsulfonylaminohydroxamique
US6107337A (en)	2000-08-22	Arylsulfonylamino hydroxamic acid derivatives
MXPA00001349A (en)	2001-05-07	Aryloxyarylsulfonylamino hydroxamic acid derivatives
HK1029575B (en)	2005-04-01	Aryloxyarylsulfonylamino hydroxamic acid derivatives
MXPA99010152A (en)	2000-05-01	Hydroxyamide derivatives of 5-oxo-pirrolidine-2-carboxyl acid