NO881531L - Acylderivater. - Google Patents
Acylderivater.Info
- Publication number
- NO881531L NO881531L NO881531A NO881531A NO881531L NO 881531 L NO881531 L NO 881531L NO 881531 A NO881531 A NO 881531A NO 881531 A NO881531 A NO 881531A NO 881531 L NO881531 L NO 881531L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- carboxylic acid
- oxo
- thia
- thio
- Prior art date
Links
- 125000002252 acyl group Chemical group 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 150000002148 esters Chemical class 0.000 claims abstract description 35
- 125000006239 protecting group Chemical group 0.000 claims abstract description 17
- 150000004677 hydrates Chemical class 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 76
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 76
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 75
- -1 2-carbamoyl-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl Chemical group 0.000 claims description 72
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 33
- 239000007858 starting material Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- SCNWTQPZTZMXBG-UHFFFAOYSA-N 2-methyloct-2-enoic acid Chemical compound CCCCCC=C(C)C(O)=O SCNWTQPZTZMXBG-UHFFFAOYSA-N 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 44
- 229910001868 water Inorganic materials 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- KBDRKWSAVPVXJR-UHFFFAOYSA-N methyl 7-methyl-5-sulfanylidene-1h-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate Chemical compound S=C1C=C(C)N2NC(C(=O)OC)=NC2=N1 KBDRKWSAVPVXJR-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- CUFLZUDASVUNOE-UHFFFAOYSA-N methyl 3,4-dihydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(O)=C1 CUFLZUDASVUNOE-UHFFFAOYSA-N 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- 229930186147 Cephalosporin Natural products 0.000 description 3
- VWLZORAIBBOGRK-UHFFFAOYSA-N FC(F)(F)C1=CC(S)=NC2=C(C(=O)OC)C=NN21 Chemical compound FC(F)(F)C1=CC(S)=NC2=C(C(=O)OC)C=NN21 VWLZORAIBBOGRK-UHFFFAOYSA-N 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229940124587 cephalosporin Drugs 0.000 description 3
- 150000001780 cephalosporins Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- KWMONYNIXXANLL-UHFFFAOYSA-N methyl 7-sulfanylidene-1,8,10,12-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),8,10-triene-11-carboxylate Chemical compound N12NC(C(=O)OC)=NC2=NC(=S)C2=C1CCC2 KWMONYNIXXANLL-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- UNGPSSXROBWAES-NSPYISDASA-N (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-oxoacetyl]amino]-3-[(11-carbamoyl-1,8,10,12-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraen-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N1)C(C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)CSC1=NC=2N(C3=C1CCC3)N=C(N2)C(N)=O)=O UNGPSSXROBWAES-NSPYISDASA-N 0.000 description 2
- ILAXVTBYXYKPKO-ADLMAVQZSA-N (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-oxoacetyl]amino]-3-[(11-carboxy-1,8,10,12-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraen-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)C(C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)CSC1=NC=2N(C3=C1CCC3)N=C(N=2)C(=O)O)=O ILAXVTBYXYKPKO-ADLMAVQZSA-N 0.000 description 2
- MFOJIZZXHHRTSM-RFAUZJTJSA-N (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-oxoacetyl]amino]-3-[[2-carboxy-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N1)C(C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)CSC1=NC=2N(C(=C1)C(F)(F)F)N=C(N2)C(=O)O)=O MFOJIZZXHHRTSM-RFAUZJTJSA-N 0.000 description 2
- ULEJWTQLAJJXCL-BMLIUANNSA-N (6r,7r)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-oxoacetyl]amino]-3-[(2-carbamoyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)CSC1=CC(=NC2=NC(=NN21)C(N)=O)C)C(O)=O)C(=O)C(=O)C1=CSC(N)=N1 ULEJWTQLAJJXCL-BMLIUANNSA-N 0.000 description 2
- NBFSZVVZILQJHG-QLJPJBMISA-N (6r,7r)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-oxoacetyl]amino]-3-[(2-carboxy-7-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)CSC=1C=C(N2N=C(N=C2N=1)C(O)=O)C)C(O)=O)C(=O)C(=O)C1=CSC(N)=N1 NBFSZVVZILQJHG-QLJPJBMISA-N 0.000 description 2
- HYTPOANVTXZINE-CWTRNNRKSA-N (6r,7r)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-oxoacetyl]amino]-3-[(3-carbamoyl-5-methylpyrazolo[1,5-a]pyrimidin-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)CSC1=CC(=NC2=C(C(N)=O)C=NN21)C)C(O)=O)C(=O)C(=O)C1=CSC(N)=N1 HYTPOANVTXZINE-CWTRNNRKSA-N 0.000 description 2
- AWVZYPRXSSDVCM-JDNHERCYSA-N (6r,7r)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-oxoacetyl]amino]-3-[[2-carbamoyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)CSC1=CC(=NC2=NC(=NN21)C(=O)N)C(F)(F)F)C(O)=O)C(=O)C(=O)C1=CSC(N)=N1 AWVZYPRXSSDVCM-JDNHERCYSA-N 0.000 description 2
- GQMBLYZBRLINDL-MEBBXXQBSA-N (6r,7r)-7-amino-3-[(3-carbamoyl-5-methylpyrazolo[1,5-a]pyrimidin-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C=1N2C(=O)[C@@H](N)[C@H]2SCC=1CSC1=CC(C)=NC2=C(C(N)=O)C=NN21 GQMBLYZBRLINDL-MEBBXXQBSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 2
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 2
- ZNPNOVHKCAAQCG-UHFFFAOYSA-N 2-chloro-1-methylpyridin-1-ium Chemical compound C[N+]1=CC=CC=C1Cl ZNPNOVHKCAAQCG-UHFFFAOYSA-N 0.000 description 2
- HPCOTNDGWUUBKI-UHFFFAOYSA-M 2-fluoro-1-methylpyridin-1-ium;chloride Chemical compound [Cl-].C[N+]1=CC=CC=C1F HPCOTNDGWUUBKI-UHFFFAOYSA-M 0.000 description 2
- WGXWEXNJRZMIPT-UHFFFAOYSA-N 3,4-dihydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=C(O)C(O)=C1 WGXWEXNJRZMIPT-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-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
- LHBFHEKLOFYNAM-UHFFFAOYSA-N 7-methyl-5-sulfanylidene-1h-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid Chemical compound CC1=CC(=S)N=C2N=C(C(O)=O)NN12 LHBFHEKLOFYNAM-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FOPPBRUPIHUFAH-UHFFFAOYSA-N FC(F)(F)C1=CC(S)=NC2=C(C(=O)N)C=NN21 Chemical compound FC(F)(F)C1=CC(S)=NC2=C(C(=O)N)C=NN21 FOPPBRUPIHUFAH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 2
- RDJCUOBLSZUWEJ-UHFFFAOYSA-N N1=C(C)C=C(S)N2N=C(C(N)=O)N=C21 Chemical compound N1=C(C)C=C(S)N2N=C(C(N)=O)N=C21 RDJCUOBLSZUWEJ-UHFFFAOYSA-N 0.000 description 2
- CQEOMHWLEVHTAU-UHFFFAOYSA-N N1=C(C)C=C(S)N2N=CC(C(O)=O)=C21 Chemical compound N1=C(C)C=C(S)N2N=CC(C(O)=O)=C21 CQEOMHWLEVHTAU-UHFFFAOYSA-N 0.000 description 2
- KHHXEAIGVICDBP-UHFFFAOYSA-N OC1=CC(C(F)(F)F)=NC2=C(C(=O)OC)C=NN21 Chemical compound OC1=CC(C(F)(F)F)=NC2=C(C(=O)OC)C=NN21 KHHXEAIGVICDBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
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- SIJYLNWLBGNWSS-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid Chemical compound N1=CC=CN2N=C(C(=O)O)N=C21 SIJYLNWLBGNWSS-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- NGLYRMQYRAWHDZ-UHFFFAOYSA-N azane 7-methyl-5-sulfanylidene-1H-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound N.CC1=CC(=S)N=C2N=C(C(N)=O)NN12 NGLYRMQYRAWHDZ-UHFFFAOYSA-N 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 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 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 1
- FJPMPRISHGPXID-UHFFFAOYSA-N ethyl 5-methyl-7-sulfanylidene-1h-pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound CCOC(=O)C1=CNN2C1=NC(C)=CC2=S FJPMPRISHGPXID-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 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
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960004393 lidocaine hydrochloride Drugs 0.000 description 1
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- GZZBZEHTYJVWNQ-UHFFFAOYSA-N methyl 3-[(2-oxocyclopentanecarbonyl)amino]-1h-1,2,4-triazole-5-carboxylate Chemical compound N1C(C(=O)OC)=NC(NC(=O)C2C(CCC2)=O)=N1 GZZBZEHTYJVWNQ-UHFFFAOYSA-N 0.000 description 1
- XHLLZJKLJBQTSK-UHFFFAOYSA-N methyl 5-chloro-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate Chemical compound N1=C(Cl)C=C(C(F)(F)F)N2N=C(C(=O)OC)N=C21 XHLLZJKLJBQTSK-UHFFFAOYSA-N 0.000 description 1
- OTLZIVZBNUAIPQ-UHFFFAOYSA-N methyl 5-chloro-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound FC(F)(F)C1=CC(Cl)=NC2=C(C(=O)OC)C=NN21 OTLZIVZBNUAIPQ-UHFFFAOYSA-N 0.000 description 1
- WZDKBSWAQJIUNN-UHFFFAOYSA-N methyl 5-oxo-7-(trifluoromethyl)-1h-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate Chemical compound O=C1C=C(C(F)(F)F)N2NC(C(=O)OC)=NC2=N1 WZDKBSWAQJIUNN-UHFFFAOYSA-N 0.000 description 1
- XZCIVGWFOVYKLG-UHFFFAOYSA-N methyl 5-oxo-7-(trifluoromethyl)-4H-pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound FC(F)(F)C1=CC(O)=NC2=C(C(=O)OC)C=NN21 XZCIVGWFOVYKLG-UHFFFAOYSA-N 0.000 description 1
- QXZAXBDUDWGNLY-UHFFFAOYSA-N methyl 7-chloro-1,8,10,12-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraene-11-carboxylate Chemical compound N12N=C(C(=O)OC)N=C2N=C(Cl)C2=C1CCC2 QXZAXBDUDWGNLY-UHFFFAOYSA-N 0.000 description 1
- HQSMMRNMSDPFFV-UHFFFAOYSA-N methyl 7-chloro-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate Chemical compound N1=C(C(F)(F)F)C=C(Cl)N2N=C(C(=O)OC)N=C21 HQSMMRNMSDPFFV-UHFFFAOYSA-N 0.000 description 1
- GXZVPANIYQASAS-UHFFFAOYSA-N methyl 7-chloro-5-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound ClC1=CC(C(F)(F)F)=NC2=C(C(=O)OC)C=NN21 GXZVPANIYQASAS-UHFFFAOYSA-N 0.000 description 1
- BRKSKQUXMCHWJN-UHFFFAOYSA-N methyl 7-methyl-5-oxo-4H-pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound OC1=NC=2N(C(=C1)C)N=CC2C(=O)OC BRKSKQUXMCHWJN-UHFFFAOYSA-N 0.000 description 1
- RVMLHVIXZPJRKD-UHFFFAOYSA-N methyl 7-oxo-1,8,10,12-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),9,11-triene-11-carboxylate Chemical compound OC1=NC=2N(C3=C1CCC3)N=C(N2)C(=O)OC RVMLHVIXZPJRKD-UHFFFAOYSA-N 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
- DPPZZROGXWQSPF-UHFFFAOYSA-N n'-(2-aminooxy-2-methylpropanoyl)-3,4-dihydroxybenzohydrazide;hydrochloride Chemical compound Cl.NOC(C)(C)C(=O)NNC(=O)C1=CC=C(O)C(O)=C1 DPPZZROGXWQSPF-UHFFFAOYSA-N 0.000 description 1
- PGVANYUBAZCUEF-UHFFFAOYSA-N n'-(2-aminooxy-2-methylpropanoyl)-3-chloro-4,5-dihydroxybenzohydrazide;hydrochloride Chemical compound Cl.NOC(C)(C)C(=O)NNC(=O)C1=CC(O)=C(O)C(Cl)=C1 PGVANYUBAZCUEF-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 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 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- WRVHPSSSTBDGRK-UHFFFAOYSA-N sodium;sulfane;hydrate Chemical compound O.[Na].S WRVHPSSSTBDGRK-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH140787 | 1987-04-10 | ||
| CH165787 | 1987-04-30 | ||
| CH241387 | 1987-06-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO881531D0 NO881531D0 (no) | 1988-04-08 |
| NO881531L true NO881531L (no) | 1988-10-11 |
Family
ID=27172951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO881531A NO881531L (no) | 1987-04-10 | 1988-04-08 | Acylderivater. |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0286145A3 (fi) |
| JP (1) | JPS63258479A (fi) |
| KR (1) | KR880012612A (fi) |
| AU (1) | AU604868B2 (fi) |
| DK (1) | DK179388A (fi) |
| FI (1) | FI881650A (fi) |
| HU (1) | HU201947B (fi) |
| IL (1) | IL85972A0 (fi) |
| MC (1) | MC1921A1 (fi) |
| NO (1) | NO881531L (fi) |
| NZ (1) | NZ224129A (fi) |
| PH (1) | PH25104A (fi) |
| PT (1) | PT87201A (fi) |
| YU (2) | YU70988A (fi) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI872879A (fi) * | 1986-07-21 | 1988-01-22 | Sankei Yakuhin Kk | --laktamfoerening, foerfarande foer dess framstaellning, denna innehaollande laekemedelskomposition foer behandling av sjukdom med bakterieinfektion samt mellanprodukter foer dess syntes. |
| NZ225383A (en) * | 1987-08-07 | 1990-03-27 | Sankei Yakuhin Kk | Cephalosporin derivatives and pharmaceutical compositions |
| US5077432A (en) * | 1990-01-22 | 1991-12-31 | E. R. Squibb & Sons, Inc. | Monobactam hydrazides containing catechol sulfonic acid groups |
| US5030724A (en) * | 1990-01-22 | 1991-07-09 | E. R. Squibb & Sons, Inc. | Monobactam hydrazides containing catechol sulfonic acid groups |
| EP0544166A3 (en) * | 1991-11-26 | 1993-11-03 | Hoffmann La Roche | Cephalosporinderivatives |
| US6488673B1 (en) | 1997-04-07 | 2002-12-03 | Broncus Technologies, Inc. | Method of increasing gas exchange of a lung |
| US7027869B2 (en) | 1998-01-07 | 2006-04-11 | Asthmatx, Inc. | Method for treating an asthma attack |
| US6273907B1 (en) | 1997-04-07 | 2001-08-14 | Broncus Technologies, Inc. | Bronchial stenter |
| US6200333B1 (en) | 1997-04-07 | 2001-03-13 | Broncus Technologies, Inc. | Bronchial stenter |
| US5972026A (en) | 1997-04-07 | 1999-10-26 | Broncus Technologies, Inc. | Bronchial stenter having diametrically adjustable electrodes |
| US7921855B2 (en) | 1998-01-07 | 2011-04-12 | Asthmatx, Inc. | Method for treating an asthma attack |
| US8181656B2 (en) | 1998-06-10 | 2012-05-22 | Asthmatx, Inc. | Methods for treating airways |
| US7198635B2 (en) | 2000-10-17 | 2007-04-03 | Asthmatx, Inc. | Modification of airways by application of energy |
| US8251070B2 (en) | 2000-03-27 | 2012-08-28 | Asthmatx, Inc. | Methods for treating airways |
| US7104987B2 (en) | 2000-10-17 | 2006-09-12 | Asthmatx, Inc. | Control system and process for application of energy to airway walls and other mediums |
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Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE150507T1 (de) * | 1983-12-29 | 1987-02-26 | Mochida Pharmaceutical Co., Ltd., Tokio/Tokyo | Cephalosporinverbindungen, verfahren zu ihrer herstellung und pharmazeutishe praeparate. |
| JPS61267583A (ja) * | 1985-01-21 | 1986-11-27 | Sankei Yakuhin Kk | 新規なβ−ラクタム抗生物質 |
| NZ215527A (en) * | 1985-04-01 | 1989-06-28 | Mochida Pharm Co Ltd | Cephalosporin derivatives and pharmaceutical compositions |
| FI872879A (fi) * | 1986-07-21 | 1988-01-22 | Sankei Yakuhin Kk | --laktamfoerening, foerfarande foer dess framstaellning, denna innehaollande laekemedelskomposition foer behandling av sjukdom med bakterieinfektion samt mellanprodukter foer dess syntes. |
| US4880798A (en) * | 1986-11-25 | 1989-11-14 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
-
1988
- 1988-03-07 MC MC881968A patent/MC1921A1/xx unknown
- 1988-03-30 DK DK179388A patent/DK179388A/da not_active Application Discontinuation
- 1988-04-04 IL IL85972A patent/IL85972A0/xx unknown
- 1988-04-06 HU HU881704A patent/HU201947B/hu not_active IP Right Cessation
- 1988-04-06 NZ NZ224129A patent/NZ224129A/xx unknown
- 1988-04-06 AU AU14309/88A patent/AU604868B2/en not_active Ceased
- 1988-04-06 PH PH36758A patent/PH25104A/en unknown
- 1988-04-08 YU YU00709/88A patent/YU70988A/xx unknown
- 1988-04-08 PT PT87201A patent/PT87201A/pt not_active Application Discontinuation
- 1988-04-08 FI FI881650A patent/FI881650A/fi not_active IP Right Cessation
- 1988-04-08 NO NO881531A patent/NO881531L/no unknown
- 1988-04-08 JP JP63085489A patent/JPS63258479A/ja active Pending
- 1988-04-09 KR KR1019880004078A patent/KR880012612A/ko not_active Application Discontinuation
- 1988-04-11 EP EP19880105733 patent/EP0286145A3/en not_active Withdrawn
-
1989
- 1989-06-16 YU YU01236/89A patent/YU123689A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU70988A (en) | 1989-12-31 |
| MC1921A1 (fr) | 1989-04-06 |
| FI881650A (fi) | 1988-10-11 |
| PT87201A (pt) | 1989-05-12 |
| FI881650A0 (fi) | 1988-04-08 |
| HU201947B (en) | 1991-01-28 |
| YU123689A (en) | 1991-06-30 |
| NZ224129A (en) | 1991-02-26 |
| PH25104A (en) | 1991-02-19 |
| AU604868B2 (en) | 1991-01-03 |
| AU1430988A (en) | 1988-10-13 |
| IL85972A0 (en) | 1988-09-30 |
| KR880012612A (ko) | 1988-11-28 |
| HUT46919A (en) | 1988-12-28 |
| NO881531D0 (no) | 1988-04-08 |
| DK179388A (da) | 1988-10-11 |
| EP0286145A2 (en) | 1988-10-12 |
| EP0286145A3 (en) | 1990-10-10 |
| DK179388D0 (da) | 1988-03-30 |
| JPS63258479A (ja) | 1988-10-25 |
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