SU1503682A3 - Способ получени енольных производных оксикамов - Google Patents
Способ получени енольных производных оксикамов Download PDFInfo
- Publication number
- SU1503682A3 SU1503682A3 SU843829753A SU3829753A SU1503682A3 SU 1503682 A3 SU1503682 A3 SU 1503682A3 SU 843829753 A SU843829753 A SU 843829753A SU 3829753 A SU3829753 A SU 3829753A SU 1503682 A3 SU1503682 A3 SU 1503682A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mmol
- methyl
- pyridyl
- multiplet
- found
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 52
- 150000002085 enols Chemical class 0.000 title claims abstract description 4
- -1 6-methyl-2-pyridyl Chemical group 0.000 claims abstract description 49
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims abstract description 3
- 125000000129 anionic group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 239000003960 organic solvent Substances 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 abstract description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 123
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 87
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
- 239000000047 product Substances 0.000 description 48
- 239000003921 oil Substances 0.000 description 45
- 238000005481 NMR spectroscopy Methods 0.000 description 36
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- 239000013078 crystal Substances 0.000 description 33
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 29
- 229960002702 piroxicam Drugs 0.000 description 28
- 238000010992 reflux Methods 0.000 description 27
- 239000007787 solid Substances 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- 239000000203 mixture Substances 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 19
- 229910000027 potassium carbonate Inorganic materials 0.000 description 18
- 239000006260 foam Substances 0.000 description 17
- 238000001953 recrystallisation Methods 0.000 description 17
- 239000010410 layer Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 239000000284 extract Substances 0.000 description 14
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- 239000003480 eluent Substances 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 11
- 235000009518 sodium iodide Nutrition 0.000 description 10
- 239000012267 brine Substances 0.000 description 9
- 238000002329 infrared spectrum Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 101710178747 Phosphatidate cytidylyltransferase 1 Proteins 0.000 description 8
- 102100031075 Serine/threonine-protein kinase Chk2 Human genes 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
- 238000011097 chromatography purification Methods 0.000 description 6
- 239000012264 purified product Substances 0.000 description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 4
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 241000208202 Linaceae Species 0.000 description 3
- 235000004431 Linum usitatissimum Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 101100476979 Rhodobacter capsulatus sdsA gene Proteins 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- BOXZXICVMMSYPE-UHFFFAOYSA-N chloromethyl benzoate Chemical compound ClCOC(=O)C1=CC=CC=C1 BOXZXICVMMSYPE-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229940050176 methyl chloride Drugs 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- CGKKDGMMKSOGLM-UHFFFAOYSA-N 1-chloroethyl acetate Chemical compound CC(Cl)OC(C)=O CGKKDGMMKSOGLM-UHFFFAOYSA-N 0.000 description 2
- ONZWFHWHTYZZLM-UHFFFAOYSA-N 1-chloroethyl cyclohexyl carbonate Chemical compound CC(Cl)OC(=O)OC1CCCCC1 ONZWFHWHTYZZLM-UHFFFAOYSA-N 0.000 description 2
- MIGZEIZMIDGNJM-UHFFFAOYSA-N 1-chloroethyl decyl carbonate Chemical compound CCCCCCCCCCOC(=O)OC(C)Cl MIGZEIZMIDGNJM-UHFFFAOYSA-N 0.000 description 2
- YQDLLPYWECJXLT-UHFFFAOYSA-N 1-chloroethyl hexyl carbonate Chemical compound CCCCCCOC(=O)OC(C)Cl YQDLLPYWECJXLT-UHFFFAOYSA-N 0.000 description 2
- OJWNPIWPCSJFLP-UHFFFAOYSA-N 1-chloroethyl hydrogen carbonate Chemical compound CC(Cl)OC(O)=O OJWNPIWPCSJFLP-UHFFFAOYSA-N 0.000 description 2
- CERXDWLUWLFFEK-UHFFFAOYSA-N 1-chloroethyl methyl carbonate Chemical compound COC(=O)OC(C)Cl CERXDWLUWLFFEK-UHFFFAOYSA-N 0.000 description 2
- IXMVJDKNCLOWPR-UHFFFAOYSA-N 1-chloroethyl propanoate Chemical compound CCC(=O)OC(C)Cl IXMVJDKNCLOWPR-UHFFFAOYSA-N 0.000 description 2
- CLMSHAWYULIVFQ-UHFFFAOYSA-N 3-bromo-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(Br)OC(=O)C2=C1 CLMSHAWYULIVFQ-UHFFFAOYSA-N 0.000 description 2
- DARWLDOSIAZDME-UHFFFAOYSA-N 3-chlorobutan-2-yl hydrogen carbonate Chemical compound CC(Cl)C(C)OC(O)=O DARWLDOSIAZDME-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- LHOFEKWWYLEOFE-UHFFFAOYSA-N CC(C(C1=CC=CC=C1)OC(=O)O)Cl Chemical compound CC(C(C1=CC=CC=C1)OC(=O)O)Cl LHOFEKWWYLEOFE-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 101100319896 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CIN5 gene Proteins 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- JUBQFNSRJOLWED-UHFFFAOYSA-N chloromethyl heptanoate Chemical compound CCCCCCC(=O)OCCl JUBQFNSRJOLWED-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 2
- 239000008241 heterogeneous mixture Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- VLSOCPMSUWUYRU-UHFFFAOYSA-N (3-chloro-2-methylbutan-2-yl) hydrogen carbonate Chemical compound CC(Cl)C(C)(C)OC(O)=O VLSOCPMSUWUYRU-UHFFFAOYSA-N 0.000 description 1
- OBQPKGCVMCIETH-UHFFFAOYSA-N 1-chloro-1-(1-chloroethoxy)ethane Chemical compound CC(Cl)OC(C)Cl OBQPKGCVMCIETH-UHFFFAOYSA-N 0.000 description 1
- ATXWGWHZGZFBHI-UHFFFAOYSA-N 1-chloroethyl benzoate Chemical compound CC(Cl)OC(=O)C1=CC=CC=C1 ATXWGWHZGZFBHI-UHFFFAOYSA-N 0.000 description 1
- RBJBURJVGINATA-UHFFFAOYSA-N 1-chloroethyl hexanoate Chemical compound CCCCCC(=O)OC(C)Cl RBJBURJVGINATA-UHFFFAOYSA-N 0.000 description 1
- UWPISDYPHIOHLE-UHFFFAOYSA-N 1-chloroethyl octyl carbonate Chemical compound CCCCCCCCOC(=O)OC(C)Cl UWPISDYPHIOHLE-UHFFFAOYSA-N 0.000 description 1
- WSMINTWDWKPQQQ-UHFFFAOYSA-N 1-chloroethyl propyl carbonate Chemical compound CCCOC(=O)OC(C)Cl WSMINTWDWKPQQQ-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- UDCXNLDCQOXJNC-UHFFFAOYSA-N 2-n,4-n,1,3-tetraphenyl-1,3,2,4-diazadiphosphetidine-2,4-diamine Chemical compound C=1C=CC=CC=1NP(N1C=2C=CC=CC=2)N(C=2C=CC=CC=2)P1NC1=CC=CC=C1 UDCXNLDCQOXJNC-UHFFFAOYSA-N 0.000 description 1
- FHYFLMZUZUUPDY-UHFFFAOYSA-N 2h-thiazine-3-carboxamide Chemical compound NC(=O)C1=CC=CSN1 FHYFLMZUZUUPDY-UHFFFAOYSA-N 0.000 description 1
- LFJJGHGXHXXDFT-UHFFFAOYSA-N 3-bromooxolan-2-one Chemical compound BrC1CCOC1=O LFJJGHGXHXXDFT-UHFFFAOYSA-N 0.000 description 1
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- FRPHFZCDPYBUAU-UHFFFAOYSA-N Bromocresolgreen Chemical compound CC1=C(Br)C(O)=C(Br)C=C1C1(C=2C(=C(Br)C(O)=C(Br)C=2)C)C2=CC=CC=C2S(=O)(=O)O1 FRPHFZCDPYBUAU-UHFFFAOYSA-N 0.000 description 1
- XHOFNQOWNCKFFG-UHFFFAOYSA-N CCCCCCC(CCl)C(O)=O Chemical compound CCCCCCC(CCl)C(O)=O XHOFNQOWNCKFFG-UHFFFAOYSA-N 0.000 description 1
- LLPXDUIGNBMBSD-UHFFFAOYSA-N CN1C(=C(C2=CC=CC=C2S1)OC)C(=O)NC3=CC=CC=N3 Chemical compound CN1C(=C(C2=CC=CC=C2S1)OC)C(=O)NC3=CC=CC=N3 LLPXDUIGNBMBSD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
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- 206010067482 No adverse event Diseases 0.000 description 1
- 101100302210 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) RNR1 gene Proteins 0.000 description 1
- IUHFWCGCSVTMPG-UHFFFAOYSA-N [C].[C] Chemical group [C].[C] IUHFWCGCSVTMPG-UHFFFAOYSA-N 0.000 description 1
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- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
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- PJGJQVRXEUVAFT-UHFFFAOYSA-N chloroiodomethane Chemical compound ClCI PJGJQVRXEUVAFT-UHFFFAOYSA-N 0.000 description 1
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- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- JRCUJOMLYAQHDP-UHFFFAOYSA-N chloromethyl octanoate Chemical compound CCCCCCCC(=O)OCCl JRCUJOMLYAQHDP-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
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- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- ZUBZATZOEPUUQF-UHFFFAOYSA-N isopropylhexane Natural products CCCCCCC(C)C ZUBZATZOEPUUQF-UHFFFAOYSA-N 0.000 description 1
- 229950002252 isoxicam Drugs 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56390283A | 1983-12-21 | 1983-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1503682A3 true SU1503682A3 (ru) | 1989-08-23 |
Family
ID=24252352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU843829753A SU1503682A3 (ru) | 1983-12-21 | 1984-12-20 | Способ получени енольных производных оксикамов |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPH0246036B2 (OSRAM) |
| CS (1) | CS248726B2 (OSRAM) |
| IN (1) | IN162323B (OSRAM) |
| SU (1) | SU1503682A3 (OSRAM) |
| ZA (1) | ZA849926B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2544853C1 (ru) * | 2013-12-18 | 2015-03-20 | Открытое Акционерное Общество "Международная Научно-Технологическая Корпорация" | N-ГЕТАРИЛЗАМЕЩЕННЫЕ 4-ГИДРОКСИ-1-МЕТИЛ-2,2-ДИОКСО-1H-2λ6,1-БЕНЗОТИАЗИН-3-КАРБОКСАМИДЫ, ПРОЯВЛЯЮЩИЕ АНАЛЬГЕТИЧЕСКУЮ АКТИВНОСТЬ |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU199833B (en) * | 1986-05-16 | 1990-03-28 | Pfizer | Process for producing benzothiazine dioxide derivatives |
| WO1989003682A1 (en) * | 1987-10-26 | 1989-05-05 | Pfizer Inc. | Benzothiazine dioxide derivatives |
| JP5378221B2 (ja) * | 2006-10-11 | 2013-12-25 | テックフィールズ バイオケム カンパニー リミテッド | 非常に高い皮膚浸透率を有するオキシカム及び関連化合物の正荷電水溶性プロドラッグ |
-
1984
- 1984-10-26 IN IN831/DEL/84A patent/IN162323B/en unknown
- 1984-12-19 CS CS1000284A patent/CS248726B2/cs unknown
- 1984-12-20 SU SU843829753A patent/SU1503682A3/ru active
- 1984-12-20 ZA ZA849926A patent/ZA849926B/xx unknown
- 1984-12-21 JP JP27058684A patent/JPH0246036B2/ja not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| Патен-Р US № 3892740, кл. 260/243, 1974. Патент US № 4180662, кл. С 07 D 513/04, 1981. Патент US № 4309427, кл. С 07 D 279/02, 1982. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2544853C1 (ru) * | 2013-12-18 | 2015-03-20 | Открытое Акционерное Общество "Международная Научно-Технологическая Корпорация" | N-ГЕТАРИЛЗАМЕЩЕННЫЕ 4-ГИДРОКСИ-1-МЕТИЛ-2,2-ДИОКСО-1H-2λ6,1-БЕНЗОТИАЗИН-3-КАРБОКСАМИДЫ, ПРОЯВЛЯЮЩИЕ АНАЛЬГЕТИЧЕСКУЮ АКТИВНОСТЬ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0246036B2 (ja) | 1990-10-12 |
| ZA849926B (en) | 1986-08-27 |
| IN162323B (OSRAM) | 1988-04-30 |
| CS248726B2 (cs) | 1987-02-12 |
| JPS60156688A (ja) | 1985-08-16 |
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