CA1242199A - O-substituted pyruvic acid oximes, processes for the preparation thereof and pharmaceutical compositions which contain these new compounds - Google Patents
O-substituted pyruvic acid oximes, processes for the preparation thereof and pharmaceutical compositions which contain these new compoundsInfo
- Publication number
- CA1242199A CA1242199A CA000386602A CA386602A CA1242199A CA 1242199 A CA1242199 A CA 1242199A CA 000386602 A CA000386602 A CA 000386602A CA 386602 A CA386602 A CA 386602A CA 1242199 A CA1242199 A CA 1242199A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- propionic acid
- process according
- reacting
- radical
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 97
- -1 O-substituted pyruvic acid oximes Chemical class 0.000 title claims abstract description 78
- 150000001875 compounds Chemical class 0.000 title claims abstract description 49
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- MVGBKLTYYAYYGY-UHFFFAOYSA-N pyruvic oxime Chemical class ON=C(C)C(O)=O MVGBKLTYYAYYGY-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 150000002367 halogens Chemical class 0.000 claims abstract description 24
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 150000002825 nitriles Chemical class 0.000 claims abstract description 21
- 150000001408 amides Chemical class 0.000 claims abstract description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 7
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 59
- 239000002253 acid Substances 0.000 claims description 58
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 44
- 239000000126 substance Substances 0.000 claims description 41
- 229940107700 pyruvic acid Drugs 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- 159000000000 sodium salts Chemical class 0.000 claims description 17
- 229910052708 sodium Inorganic materials 0.000 claims description 13
- 239000011734 sodium Substances 0.000 claims description 13
- 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 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 9
- 235000019260 propionic acid Nutrition 0.000 claims description 8
- 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 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- JPDDKDFIXZXYRU-UHFFFAOYSA-N 2-(3-phenylprop-2-enoxyimino)propanoic acid Chemical compound OC(=O)C(C)=NOCC=CC1=CC=CC=C1 JPDDKDFIXZXYRU-UHFFFAOYSA-N 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 5
- UZTPLSIRHBWOAR-UHFFFAOYSA-N 2-(3-phenylprop-2-enoxyimino)acetic acid Chemical compound OC(=O)C=NOCC=CC1=CC=CC=C1 UZTPLSIRHBWOAR-UHFFFAOYSA-N 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- OCSNCNDDHOJMFL-UHFFFAOYSA-N 2-(3-phenylprop-2-enoxyimino)propanoyl chloride Chemical compound ClC(=O)C(C)=NOCC=CC1=CC=CC=C1 OCSNCNDDHOJMFL-UHFFFAOYSA-N 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 claims description 2
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 claims description 2
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 claims description 2
- JJFOBACUIRKUPN-UHFFFAOYSA-N 2-bromoethoxybenzene Chemical compound BrCCOC1=CC=CC=C1 JJFOBACUIRKUPN-UHFFFAOYSA-N 0.000 claims description 2
- JRQAAYVLPPGEHT-UHFFFAOYSA-N 2-bromoethylcyclohexane Chemical compound BrCCC1CCCCC1 JRQAAYVLPPGEHT-UHFFFAOYSA-N 0.000 claims description 2
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 claims description 2
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 claims description 2
- RKNCIBMWPVZEAJ-UHFFFAOYSA-N 3-bromoprop-1-ynylbenzene Chemical compound BrCC#CC1=CC=CC=C1 RKNCIBMWPVZEAJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 15
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 5
- 230000000875 corresponding effect Effects 0.000 claims 4
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical group F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 4
- DRDNQLXAKDEYGE-UHFFFAOYSA-N 1-(4-methylpiperazin-1-yl)-2-(3-phenylprop-2-enoxyimino)propan-1-one Chemical compound C1CN(C)CCN1C(=O)C(C)=NOCC=CC1=CC=CC=C1 DRDNQLXAKDEYGE-UHFFFAOYSA-N 0.000 claims 3
- GTIIVRSGHNDEJW-UHFFFAOYSA-N 2-(2-methoxyethoxyimino)propanoic acid Chemical compound COCCON=C(C)C(O)=O GTIIVRSGHNDEJW-UHFFFAOYSA-N 0.000 claims 3
- VGFHZNXCRQZUIO-UHFFFAOYSA-N 2-(2-phenylethoxyimino)propanoic acid Chemical compound OC(=O)C(C)=NOCCC1=CC=CC=C1 VGFHZNXCRQZUIO-UHFFFAOYSA-N 0.000 claims 3
- ZCPRJSWTOSONJW-UHFFFAOYSA-N 2-(3-phenylprop-2-enoxyimino)butanoic acid Chemical compound CCC(C(O)=O)=NOCC=CC1=CC=CC=C1 ZCPRJSWTOSONJW-UHFFFAOYSA-N 0.000 claims 3
- UIOZXSFWCLHTSH-UHFFFAOYSA-N 2-(3-phenylprop-2-ynoxyimino)propanoic acid Chemical compound OC(=O)C(C)=NOCC#CC1=CC=CC=C1 UIOZXSFWCLHTSH-UHFFFAOYSA-N 0.000 claims 3
- ZBXNLWHSYKEAOW-UHFFFAOYSA-N 2-[2-(4-methylphenyl)ethoxyimino]propanoic acid Chemical compound OC(=O)C(C)=NOCCC1=CC=C(C)C=C1 ZBXNLWHSYKEAOW-UHFFFAOYSA-N 0.000 claims 3
- AOUNSDSNIRMVKG-UHFFFAOYSA-N 2-[3-(2-chlorophenyl)prop-2-enoxyimino]propanoic acid Chemical compound OC(=O)C(C)=NOCC=CC1=CC=CC=C1Cl AOUNSDSNIRMVKG-UHFFFAOYSA-N 0.000 claims 3
- XUVMWWUFBKAHBB-UHFFFAOYSA-N 2-[3-(3-methoxyphenyl)prop-2-enoxyimino]propanoic acid Chemical compound COC1=CC=CC(C=CCON=C(C)C(O)=O)=C1 XUVMWWUFBKAHBB-UHFFFAOYSA-N 0.000 claims 3
- KKZWJAXYFYLGEK-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)prop-2-enoxyimino]propanoic acid Chemical compound OC(=O)C(C)=NOCC=CC1=CC=C(Cl)C=C1 KKZWJAXYFYLGEK-UHFFFAOYSA-N 0.000 claims 3
- DRQWXHYOGVWMME-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)prop-2-enoxyimino]propanoic acid Chemical compound OC(=O)C(C)=NOCC=CC1=CC=C(F)C=C1 DRQWXHYOGVWMME-UHFFFAOYSA-N 0.000 claims 3
- LIORZEAWUGRSFJ-UHFFFAOYSA-N 2-[3-(5-chloro-2-methylphenyl)prop-2-enoxyimino]propanoic acid Chemical compound OC(=O)C(C)=NOCC=CC1=CC(Cl)=CC=C1C LIORZEAWUGRSFJ-UHFFFAOYSA-N 0.000 claims 3
- IULABMPKCHEALD-UHFFFAOYSA-N 2-[3-[3-(trifluoromethyl)phenyl]prop-2-enoxyimino]propanoic acid Chemical compound OC(=O)C(C)=NOCC=CC1=CC=CC(C(F)(F)F)=C1 IULABMPKCHEALD-UHFFFAOYSA-N 0.000 claims 3
- RCEWIDZTXSWHHQ-UHFFFAOYSA-N 2-hexoxyiminopropanoic acid Chemical compound CCCCCCON=C(C)C(O)=O RCEWIDZTXSWHHQ-UHFFFAOYSA-N 0.000 claims 3
- CSSAHPITKXSYKR-UHFFFAOYSA-N 2-octoxyiminopropanoic acid Chemical compound CCCCCCCCON=C(C)C(O)=O CSSAHPITKXSYKR-UHFFFAOYSA-N 0.000 claims 3
- JAAHPDNUNOYERT-UHFFFAOYSA-N 3-fluoro-2-(3-phenylprop-2-enoxyimino)propanoic acid Chemical compound OC(=O)C(CF)=NOCC=CC1=CC=CC=C1 JAAHPDNUNOYERT-UHFFFAOYSA-N 0.000 claims 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 3
- OKIBIDWYXSYAHQ-UHFFFAOYSA-N 2-[3-(3-chlorophenyl)prop-2-enoxyimino]propanoic acid Chemical compound OC(=O)C(C)=NOCC=CC1=CC=CC(Cl)=C1 OKIBIDWYXSYAHQ-UHFFFAOYSA-N 0.000 claims 2
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 2
- 208000001280 Prediabetic State Diseases 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims 2
- 238000007911 parenteral administration Methods 0.000 claims 2
- 201000009104 prediabetes syndrome Diseases 0.000 claims 2
- KAIQZWJOGNRLOG-UHFFFAOYSA-M sodium;2-(2-cyclohexylethoxyimino)propanoate Chemical compound [Na+].[O-]C(=O)C(C)=NOCCC1CCCCC1 KAIQZWJOGNRLOG-UHFFFAOYSA-M 0.000 claims 2
- IAZCKSJRRRXZEY-UHFFFAOYSA-N 1-(2-bromoethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCBr)C=C1 IAZCKSJRRRXZEY-UHFFFAOYSA-N 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 claims 1
- XMZQWZJMTBCUFT-UHFFFAOYSA-N 3-bromopropylbenzene Chemical compound BrCCCC1=CC=CC=C1 XMZQWZJMTBCUFT-UHFFFAOYSA-N 0.000 claims 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- YEXRRCHQJDSEJI-UHFFFAOYSA-M sodium;3-fluoro-2-oxopropanoate Chemical compound [Na+].[O-]C(=O)C(=O)CF YEXRRCHQJDSEJI-UHFFFAOYSA-M 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000008103 glucose Substances 0.000 description 10
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 101150065749 Churc1 gene Proteins 0.000 description 6
- 102100038239 Protein Churchill Human genes 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 150000002443 hydroxylamines Chemical class 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- 102000005548 Hexokinase Human genes 0.000 description 3
- 108700040460 Hexokinases Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 230000002218 hypoglycaemic effect Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- GPPUPQFYDYLTIY-UHFFFAOYSA-N 2-oxooctanoic acid Chemical compound CCCCCCC(=O)C(O)=O GPPUPQFYDYLTIY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 description 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3036281.3 | 1980-09-26 | ||
| DE19803036281 DE3036281A1 (de) | 1980-09-26 | 1980-09-26 | 0-substituierte brenztraubensaeureoxime, verfahren zu ihrer herstellung, ihre verwendung sowie arzneimittel, die diese verbindungen enthalten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1242199A true CA1242199A (en) | 1988-09-20 |
Family
ID=6112892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000386602A Expired CA1242199A (en) | 1980-09-26 | 1981-09-24 | O-substituted pyruvic acid oximes, processes for the preparation thereof and pharmaceutical compositions which contain these new compounds |
Country Status (14)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3208330A1 (de) * | 1982-03-09 | 1983-09-15 | Basf Ag, 6700 Ludwigshafen | Alpha-oximinoessigsaeurederivate, ihre herstellung und ihre verwendung zur herstellung von fungizid wirksamen verbindungen |
| US4584014A (en) * | 1984-07-02 | 1986-04-22 | Rohm And Haas Company | Ethylideneaminooxyacetic acids and esters |
| WO1986000522A1 (en) * | 1984-07-17 | 1986-01-30 | Boehringer Mannheim Gmbh | UTILIZATION OF alpha-CETOCARBONIC ACID HYDRAZONES AND OXINES FOR TREATING CARDIAC OR CIRCULATORY DISEASES |
| DE3528753A1 (de) * | 1985-08-10 | 1987-02-19 | Bayer Ag | Substituierte pyrazolin-5-one |
| US4740524A (en) * | 1986-05-16 | 1988-04-26 | Rohm And Haas Company | Alpha-halopyruvate oxime |
| DE3838310A1 (de) * | 1988-11-11 | 1990-05-23 | Basf Ag | Hydroxylaminderivate |
| AU620974B2 (en) * | 1989-03-31 | 1992-02-27 | Sumitomo Chemical Company, Limited | Pyrazole oxime derivatives, production of same and method of controlling extremely harmful pests |
| JPH03190141A (ja) * | 1989-12-12 | 1991-08-20 | Samsung Electron Devices Co Ltd | 平板ディスプレー用薄膜トランジスタ及びその製造方法 |
| DE4204206A1 (de) * | 1992-02-13 | 1993-08-19 | Basf Ag | Mischungen aus optisch aktiven cyclohexenonoximethern, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide |
| US5393921A (en) * | 1993-07-07 | 1995-02-28 | The Gillette Company | Process for synthesizing O-substituted oxime compounds and conversion to the corresponding O-substituted hydroxylamine |
| ES2083324B1 (es) * | 1993-11-12 | 1996-12-16 | Univ Cordoba | Procedimiento de obtencion de nitrilos a partir de alfa-cetoacidos. |
| US5594400A (en) * | 1995-01-03 | 1997-01-14 | Siemens Stromberg-Carlson | Reed relay |
| US5570072A (en) * | 1995-01-03 | 1996-10-29 | Siemens Stromberg-Carlson | Method of establishing a relay contact arrangement |
| EP2380854A3 (en) | 2004-04-22 | 2012-07-04 | Siemens Industry, Inc. | Filtration apparatus comprising a membrane bioreactor and a treatment vessel for digesting organic materials |
| US7563363B2 (en) | 2005-10-05 | 2009-07-21 | Siemens Water Technologies Corp. | System for treating wastewater |
| US7455765B2 (en) | 2006-01-25 | 2008-11-25 | Siemens Water Technologies Corp. | Wastewater treatment system and method |
| CN112812035B (zh) * | 2021-02-01 | 2022-07-12 | 闽江学院 | 一种氟代乙醛-氧-芳基肟类化合物及其合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2470083A (en) * | 1946-04-03 | 1949-05-17 | Walter H Hartung | Ethers of oximino acid chlorides |
| US3104258A (en) | 1958-09-25 | 1963-09-17 | Fmc Corp | Novel synthesis of amino acids |
| CH511662A (de) | 1970-07-16 | 1971-08-31 | Fischer Ag Georg | Schnellwechseleinrichtung für Aufspannvorrichtung an Drehmaschinen |
| BE791214A (fr) * | 1972-05-08 | 1973-05-10 | Glaxo Lab Ltd | Procede de preparation d'isomeres de derives d'acide hydroxyiminoacetique etherifie purs |
| US4060686A (en) | 1973-12-21 | 1977-11-29 | Janice Bradshaw | Cephalosporins having a 7-(carboxy substituted α-etherified oximinoarylacetamido) group |
| US4052194A (en) | 1974-01-24 | 1977-10-04 | Merrill Wilcox | Oxime abscission agents |
| JPS606354B2 (ja) | 1976-03-30 | 1985-02-18 | 藤沢薬品工業株式会社 | ジ置換アルコキシベンゼン誘導体およびその塩類 |
| DE2739380A1 (de) | 1977-09-01 | 1979-03-08 | Boehringer Mannheim Gmbh | N-substituierte 2-hydrazono-propionsaeure-derivate, verfahren zur herstellung derselben und arzneimittel, die diese enthalten |
| DE2837863A1 (de) | 1978-09-04 | 1980-03-13 | Ciba Geigy Ag | Oxim-derivate zum schutz von pflanzenkulturen |
| DE3031842A1 (de) | 1980-08-23 | 1982-04-08 | Boehringer Mannheim Gmbh, 6800 Mannheim | N-substituierte brenztraubensaeurehydrazone, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
-
1980
- 1980-09-26 DE DE19803036281 patent/DE3036281A1/de not_active Withdrawn
-
1981
- 1981-09-08 US US06/300,076 patent/US4425360A/en not_active Expired - Fee Related
- 1981-09-19 AT AT81107441T patent/ATE10622T1/de not_active IP Right Cessation
- 1981-09-19 DE DE8181107441T patent/DE3167634D1/de not_active Expired
- 1981-09-19 EP EP81107441A patent/EP0048911B1/de not_active Expired
- 1981-09-21 HU HU812726A patent/HU184967B/hu not_active IP Right Cessation
- 1981-09-21 IL IL63894A patent/IL63894A0/xx not_active IP Right Cessation
- 1981-09-21 ES ES505672A patent/ES8205762A1/es not_active Expired
- 1981-09-21 CS CS816933A patent/CS228907B2/cs unknown
- 1981-09-21 SU SU813336185A patent/SU1279526A1/ru active
- 1981-09-23 DD DD81233511A patent/DD201781A5/de not_active IP Right Cessation
- 1981-09-24 CA CA000386602A patent/CA1242199A/en not_active Expired
- 1981-09-25 JP JP56150828A patent/JPS5798250A/ja active Granted
-
1982
- 1982-06-08 SU SU823449247A patent/SU1217252A3/ru active
-
1987
- 1987-11-24 SG SG1024/87A patent/SG102487G/en unknown
-
1991
- 1991-11-28 HK HK948/91A patent/HK94891A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES505672A0 (es) | 1982-08-16 |
| JPS5798250A (en) | 1982-06-18 |
| SU1279526A3 (ru) | 1986-12-23 |
| DE3036281A1 (de) | 1982-05-13 |
| ES8205762A1 (es) | 1982-08-16 |
| SU1279526A1 (ru) | 1986-12-23 |
| ATE10622T1 (de) | 1984-12-15 |
| EP0048911A3 (en) | 1982-09-29 |
| EP0048911B1 (de) | 1984-12-05 |
| SG102487G (en) | 1989-01-27 |
| EP0048911A2 (de) | 1982-04-07 |
| IL63894A0 (en) | 1981-12-31 |
| HU184967B (en) | 1984-11-28 |
| JPH0226625B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-06-12 |
| HK94891A (en) | 1991-12-06 |
| DD201781A5 (de) | 1983-08-10 |
| US4425360A (en) | 1984-01-10 |
| SU1217252A3 (ru) | 1986-03-07 |
| DE3167634D1 (en) | 1985-01-17 |
| CS228907B2 (en) | 1984-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |