HRP990105A2 - Process for preparing hydroxamic acids - Google Patents
Process for preparing hydroxamic acids Download PDFInfo
- Publication number
- HRP990105A2 HRP990105A2 HR60/081,365A HRP990105A HRP990105A2 HR P990105 A2 HRP990105 A2 HR P990105A2 HR P990105 A HRP990105 A HR P990105A HR P990105 A2 HRP990105 A2 HR P990105A2
- Authority
- HR
- Croatia
- Prior art keywords
- aryl
- heteroaryl
- alkyl
- alkoxy
- formula
- Prior art date
Links
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 68
- 125000001072 heteroaryl group Chemical group 0.000 claims description 63
- -1 silyl halide Chemical class 0.000 claims description 56
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 49
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 34
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 12
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical group C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 9
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 8
- 238000011065 in-situ storage Methods 0.000 claims description 7
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- 239000000243 solution Substances 0.000 description 92
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 50
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- 239000000203 mixture Substances 0.000 description 47
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 239000012267 brine Substances 0.000 description 14
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- 229940124761 MMP inhibitor Drugs 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 12
- 239000000284 extract Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- HGMRCAGQEDXAGL-UHFFFAOYSA-N 1-[(3-ethoxy-3-oxopropyl)-[4-(4-fluorophenoxy)phenyl]sulfonylamino]cyclopentane-1-carboxylic acid Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(CCC(=O)OCC)C1(C(O)=O)CCCC1 HGMRCAGQEDXAGL-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- YALNVAOWTJTOOW-UHFFFAOYSA-N 4-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]oxane-4-carboxylic acid Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)NC1(C(=O)O)CCOCC1 YALNVAOWTJTOOW-UHFFFAOYSA-N 0.000 description 7
- 102000002274 Matrix Metalloproteinases Human genes 0.000 description 7
- 108010000684 Matrix Metalloproteinases Proteins 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000002955 isolation Methods 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 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 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- DYWSVUBJGFTOQC-UHFFFAOYSA-N xi-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 0.000 description 5
- PDAYRCHIAPCRRD-UHFFFAOYSA-N 4-(4-fluorophenoxy)benzenesulfonyl chloride Chemical compound C1=CC(F)=CC=C1OC1=CC=C(S(Cl)(=O)=O)C=C1 PDAYRCHIAPCRRD-UHFFFAOYSA-N 0.000 description 4
- IYPWBBIATXCXBV-UHFFFAOYSA-N 4-(benzhydrylideneamino)oxane-4-carboxylic acid Chemical compound C1(=CC=CC=C1)C(=NC1(CCOCC1)C(=O)O)C1=CC=CC=C1 IYPWBBIATXCXBV-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- KHBRCHARZCVROM-UHFFFAOYSA-N benzyl 4-aminooxane-4-carboxylate Chemical compound C=1C=CC=CC=1COC(=O)C1(N)CCOCC1 KHBRCHARZCVROM-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
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- FMVJYQGSRWVMQV-UHFFFAOYSA-N ethyl propiolate Chemical compound CCOC(=O)C#C FMVJYQGSRWVMQV-UHFFFAOYSA-N 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- KFNIDRLZPBRDNJ-UHFFFAOYSA-N benzyl 2-(benzhydrylideneamino)acetate Chemical compound C=1C=CC=CC=1COC(=O)CN=C(C=1C=CC=CC=1)C1=CC=CC=C1 KFNIDRLZPBRDNJ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- ZCVWLNIALLKWDO-UHFFFAOYSA-N ethyl 3-[(1-carbonochloridoylcyclopentyl)-[4-(4-fluorophenoxy)phenyl]sulfonylamino]propanoate Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(CCC(=O)OCC)C1(C(Cl)=O)CCCC1 ZCVWLNIALLKWDO-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- FFUBAZZKSHAKEL-UHFFFAOYSA-N 1-[(3-ethoxy-3-oxoprop-1-enyl)-[4-(4-fluorophenoxy)phenyl]sulfonylamino]cyclopentane-1-carboxylic acid Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(C=CC(=O)OCC)C1(C(O)=O)CCCC1 FFUBAZZKSHAKEL-UHFFFAOYSA-N 0.000 description 2
- FOZVXADQAHVUSV-UHFFFAOYSA-N 1-bromo-2-(2-bromoethoxy)ethane Chemical compound BrCCOCCBr FOZVXADQAHVUSV-UHFFFAOYSA-N 0.000 description 2
- AWDNENNPRQAAFD-UHFFFAOYSA-N 3-[[4-(4-fluorophenoxy)phenyl]sulfonyl-[3-(hydroxycarbamoyl)-8-oxabicyclo[3.2.1]octan-3-yl]amino]propanoic acid Chemical compound C1C(O2)CCC2CC1(C(=O)NO)N(CCC(O)=O)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(F)C=C1 AWDNENNPRQAAFD-UHFFFAOYSA-N 0.000 description 2
- WARXYAHFCARUNH-UHFFFAOYSA-N 3-[[4-(4-fluorophenoxy)phenyl]sulfonyl-[4-(hydroxycarbamoyl)oxan-4-yl]amino]propanoic acid Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)N(CCC(O)=O)C1(C(=O)NO)CCOCC1 WARXYAHFCARUNH-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- IBIQISDZKLPUST-UHFFFAOYSA-N 4-[(3-ethoxy-3-oxoprop-1-enyl)-[4-(4-fluorophenoxy)phenyl]sulfonylamino]oxane-4-carboxylic acid Chemical compound C(C)OC(=O)C=CN(C1(CCOCC1)C(=O)O)S(=O)(=O)C1=CC=C(C=C1)OC1=CC=C(C=C1)F IBIQISDZKLPUST-UHFFFAOYSA-N 0.000 description 2
- ZBRHTUMWSDPCMI-UHFFFAOYSA-N 4-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-n-hydroxyoxane-4-carboxamide Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)NC1(C(=O)NO)CCOCC1 ZBRHTUMWSDPCMI-UHFFFAOYSA-N 0.000 description 2
- DPDPQQHHTHKSRN-UHFFFAOYSA-N 4-aminooxane-4-carboxylic acid Chemical compound OC(=O)C1(N)CCOCC1 DPDPQQHHTHKSRN-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- YCZZQSFWHFBKMU-OLQVQODUSA-N [(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]methanol Chemical compound OC[C@H]1CC[C@@H](CO)O1 YCZZQSFWHFBKMU-OLQVQODUSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 208000007474 aortic aneurysm Diseases 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 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
- DGAJCEPJSBFKMK-UHFFFAOYSA-N benzyl 4-(benzhydrylideneamino)oxane-4-carboxylate Chemical compound C1COCCC1(N=C(C=1C=CC=CC=1)C=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 DGAJCEPJSBFKMK-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000003771 matrix metalloproteinase inhibitor Substances 0.000 description 2
- 229940121386 matrix metalloproteinase inhibitor Drugs 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229940080818 propionamide Drugs 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
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- 208000020431 spinal cord injury Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 229940063683 taxotere Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- PPLMQFARLJLZAO-UHFFFAOYSA-N triethyl(iodo)silane Chemical compound CC[Si](I)(CC)CC PPLMQFARLJLZAO-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 230000006433 tumor necrosis factor production Effects 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/14—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- 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
- A61P37/08—Antiallergic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- 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
- C07D309/04—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8136598P | 1998-04-10 | 1998-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP990105A2 true HRP990105A2 (en) | 2000-02-29 |
Family
ID=22163686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR60/081,365A HRP990105A2 (en) | 1998-04-10 | 1999-04-09 | Process for preparing hydroxamic acids |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US6288246B1 (sh) |
| EP (1) | EP0949244A3 (sh) |
| JP (1) | JPH11343277A (sh) |
| KR (1) | KR100329902B1 (sh) |
| CN (1) | CN1232023A (sh) |
| AP (1) | AP1203A (sh) |
| AR (1) | AR018180A1 (sh) |
| AU (1) | AU747629B2 (sh) |
| BG (1) | BG64154B1 (sh) |
| BR (1) | BR9901089A (sh) |
| CA (1) | CA2268680A1 (sh) |
| CO (1) | CO5070713A1 (sh) |
| DZ (1) | DZ2757A1 (sh) |
| EA (1) | EA002777B1 (sh) |
| EG (1) | EG22263A (sh) |
| GT (1) | GT199900046A (sh) |
| HR (1) | HRP990105A2 (sh) |
| HU (1) | HUP9901041A3 (sh) |
| ID (1) | ID23337A (sh) |
| IL (1) | IL129328A0 (sh) |
| IN (1) | IN192342B (sh) |
| IS (1) | IS5019A (sh) |
| MA (1) | MA24831A1 (sh) |
| NO (1) | NO991672L (sh) |
| NZ (1) | NZ335104A (sh) |
| OA (1) | OA11031A (sh) |
| PA (1) | PA8469301A1 (sh) |
| PE (1) | PE20000418A1 (sh) |
| PL (1) | PL332450A1 (sh) |
| SG (1) | SG125880A1 (sh) |
| SK (1) | SK43699A3 (sh) |
| TN (1) | TNSN99052A1 (sh) |
| TR (1) | TR199900755A2 (sh) |
| TW (1) | TW448147B (sh) |
| UA (1) | UA57750C2 (sh) |
| UY (1) | UY25460A1 (sh) |
| YU (1) | YU18199A (sh) |
| ZA (1) | ZA992631B (sh) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9918684D0 (en) | 1999-08-09 | 1999-10-13 | Novartis Ag | Organic compounds |
| US6458822B2 (en) | 2000-03-13 | 2002-10-01 | Pfizer Inc. | 2-oxo-imidazolidine-4-carboxylic acid hydroxamide compounds that inhibit matrix metalloproteinases |
| GB0103303D0 (en) | 2001-02-09 | 2001-03-28 | Novartis Ag | Organic compounds |
| WO2004106319A1 (en) * | 2003-05-30 | 2004-12-09 | Pfizer Products Inc. | Crystal forms of 4-[4-(4-fluorophenoxy)benzenesulfonylamino]-tetrahydropyran-4-carboxylic acid hydroxyamide |
| RU2326862C2 (ru) * | 2003-08-29 | 2008-06-20 | Басф Акциенгезельшафт | Способ получения о-замещенных гидроксиламиновых соединений |
| EP3082995A4 (en) | 2013-12-18 | 2017-07-05 | Brita LP | Filter assembly for filter as you pour filtration |
| TW202237119A (zh) | 2020-12-10 | 2022-10-01 | 美商住友製藥腫瘤公司 | Ａｌｋ﹘５抑制劑和彼之用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA794723B (en) | 1978-09-11 | 1980-08-27 | Univ Miami | Anti-hypertensive agents |
| GB9000725D0 (en) | 1990-01-12 | 1990-03-14 | Pfizer Ltd | Therapeutic agents |
| US5552419A (en) * | 1993-01-06 | 1996-09-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
| US5863949A (en) | 1995-03-08 | 1999-01-26 | Pfizer Inc | Arylsulfonylamino hydroxamic acid derivatives |
| TR199900387T2 (xx) | 1996-08-23 | 1999-04-21 | Pfizer Inc. | Arils�lfonilamino hidroksamik asit t�revleri. |
| EA002594B1 (ru) | 1997-02-03 | 2002-06-27 | Пфайзер Продактс Инк. | Производные арилсульфониламиногидроксамовой кислоты |
| ATE217863T1 (de) | 1997-08-08 | 2002-06-15 | Pfizer Prod Inc | Arylsulfonylaminohydroxamsäurederivate |
| PT1003720E (pt) | 1997-08-08 | 2004-07-30 | Pfizer Prod Inc | Derivados de acido ariloxiarilsulfonilamino hidroxamico |
| PA8469401A1 (es) | 1998-04-10 | 2000-05-24 | Pfizer Prod Inc | Derivados biciclicos del acido hidroxamico |
-
1999
- 1999-03-19 PA PA19998469301A patent/PA8469301A1/es unknown
- 1999-03-25 GT GT199900046A patent/GT199900046A/es unknown
- 1999-03-26 EP EP99302343A patent/EP0949244A3/en not_active Withdrawn
- 1999-04-01 SK SK436-99A patent/SK43699A3/sk unknown
- 1999-04-01 OA OA9900074A patent/OA11031A/en unknown
- 1999-04-05 IL IL12932899A patent/IL129328A0/xx unknown
- 1999-04-06 IN IN512DE1999 patent/IN192342B/en unknown
- 1999-04-06 PE PE1999000278A patent/PE20000418A1/es not_active Application Discontinuation
- 1999-04-06 IS IS5019A patent/IS5019A/is unknown
- 1999-04-06 TW TW088105453A patent/TW448147B/zh active
- 1999-04-07 DZ DZ990058A patent/DZ2757A1/xx active
- 1999-04-07 MA MA25526A patent/MA24831A1/fr unknown
- 1999-04-07 UY UY25460A patent/UY25460A1/es not_active Application Discontinuation
- 1999-04-07 TN TNTNSN99052A patent/TNSN99052A1/fr unknown
- 1999-04-07 ID IDP990307D patent/ID23337A/id unknown
- 1999-04-07 US US09/287,508 patent/US6288246B1/en not_active Expired - Fee Related
- 1999-04-07 CN CN99104834A patent/CN1232023A/zh active Pending
- 1999-04-08 KR KR1019990012326A patent/KR100329902B1/ko not_active IP Right Cessation
- 1999-04-08 AR ARP990101598A patent/AR018180A1/es not_active Application Discontinuation
- 1999-04-08 EG EG37399A patent/EG22263A/xx active
- 1999-04-08 TR TR1999/00755A patent/TR199900755A2/xx unknown
- 1999-04-08 CA CA002268680A patent/CA2268680A1/en not_active Abandoned
- 1999-04-08 UA UA99041999A patent/UA57750C2/uk unknown
- 1999-04-08 AP APAP/P/1999/001503A patent/AP1203A/en active
- 1999-04-08 YU YU18199A patent/YU18199A/sh unknown
- 1999-04-08 SG SG1999001650A patent/SG125880A1/en unknown
- 1999-04-09 AU AU23690/99A patent/AU747629B2/en not_active Ceased
- 1999-04-09 CO CO99021089A patent/CO5070713A1/es unknown
- 1999-04-09 ZA ZA9902631A patent/ZA992631B/xx unknown
- 1999-04-09 EA EA199900284A patent/EA002777B1/ru not_active IP Right Cessation
- 1999-04-09 BR BR9901089-5A patent/BR9901089A/pt not_active IP Right Cessation
- 1999-04-09 NO NO991672A patent/NO991672L/no not_active Application Discontinuation
- 1999-04-09 HR HR60/081,365A patent/HRP990105A2/hr not_active Application Discontinuation
- 1999-04-09 NZ NZ335104A patent/NZ335104A/xx unknown
- 1999-04-09 JP JP11103156A patent/JPH11343277A/ja active Pending
- 1999-04-09 HU HU9901041A patent/HUP9901041A3/hu unknown
- 1999-04-09 BG BG103319A patent/BG64154B1/bg unknown
- 1999-04-09 PL PL99332450A patent/PL332450A1/xx not_active Application Discontinuation
Also Published As
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