NL8602446A - 2-oxo-1-(gesubstitueerd sulfonyl)aminocarbonylazetidinen. - Google Patents
2-oxo-1-(gesubstitueerd sulfonyl)aminocarbonylazetidinen. Download PDFInfo
- Publication number
- NL8602446A NL8602446A NL8602446A NL8602446A NL8602446A NL 8602446 A NL8602446 A NL 8602446A NL 8602446 A NL8602446 A NL 8602446A NL 8602446 A NL8602446 A NL 8602446A NL 8602446 A NL8602446 A NL 8602446A
- Authority
- NL
- Netherlands
- Prior art keywords
- oxo
- amino
- formula
- compound
- carbonyl
- Prior art date
Links
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical class O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 title description 2
- -1 2-phenylethenyl Chemical group 0.000 claims description 386
- 150000001875 compounds Chemical class 0.000 claims description 384
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 230000004913 activation Effects 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000006371 dihalo methyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 251
- 239000000243 solution Substances 0.000 description 201
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 171
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 162
- 239000000203 mixture Substances 0.000 description 141
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 135
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 133
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
- 238000003756 stirring Methods 0.000 description 111
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 105
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 83
- 239000000725 suspension Substances 0.000 description 75
- 125000006239 protecting group Chemical group 0.000 description 70
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
- 239000012038 nucleophile Substances 0.000 description 47
- 239000000047 product Substances 0.000 description 45
- 229940086542 triethylamine Drugs 0.000 description 45
- 239000002253 acid Substances 0.000 description 44
- 239000007787 solid Substances 0.000 description 42
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 36
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 36
- 239000002244 precipitate Substances 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000000706 filtrate Substances 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 238000010511 deprotection reaction Methods 0.000 description 29
- 238000001914 filtration Methods 0.000 description 29
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- 238000001816 cooling Methods 0.000 description 27
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 25
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 239000005457 ice water Substances 0.000 description 24
- 239000000463 material Substances 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 22
- 229920001577 copolymer Polymers 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 20
- MSPCIZMDDUQPGJ-UHFFFAOYSA-N N-methyl-N-(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)N(C)C(=O)C(F)(F)F MSPCIZMDDUQPGJ-UHFFFAOYSA-N 0.000 description 20
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 20
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 20
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
- 239000002585 base Substances 0.000 description 19
- 239000013078 crystal Substances 0.000 description 19
- 239000013058 crude material Substances 0.000 description 18
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- 239000003480 eluent Substances 0.000 description 16
- 239000012043 crude product Substances 0.000 description 15
- 230000007062 hydrolysis Effects 0.000 description 15
- 238000006460 hydrolysis reaction Methods 0.000 description 15
- 230000009467 reduction Effects 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 14
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 14
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- 150000002431 hydrogen Chemical class 0.000 description 11
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 11
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 10
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 9
- 239000006188 syrup Substances 0.000 description 9
- 235000020357 syrup Nutrition 0.000 description 9
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 8
- NDVMCQUOSYOQMZ-UHFFFAOYSA-N 2,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)C(C(N)=O)[Si](C)(C)C NDVMCQUOSYOQMZ-UHFFFAOYSA-N 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 238000004108 freeze drying Methods 0.000 description 8
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- DHIVBEZCBBHIPZ-UHFFFAOYSA-N 1-aminoimidazolidin-2-one Chemical compound NN1CCNC1=O DHIVBEZCBBHIPZ-UHFFFAOYSA-N 0.000 description 7
- TUJMNQZMSQDVAR-UHFFFAOYSA-N 4-oxo-5-phenylmethoxy-1h-pyridine-2-carboxylic acid Chemical compound N1C(C(=O)O)=CC(=O)C(OCC=2C=CC=CC=2)=C1 TUJMNQZMSQDVAR-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000003039 volatile agent Substances 0.000 description 7
- 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 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 238000006073 displacement reaction Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- GMYHFMYEZAGTBN-UHFFFAOYSA-N 5-hydroxy-4-oxo-1h-pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(=O)C(O)=CN1 GMYHFMYEZAGTBN-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 5
- 229910003446 platinum oxide Inorganic materials 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- ZGEXYNBHYVEWKT-UHFFFAOYSA-N 2-(hydroxymethyl)-5-phenylmethoxypyran-4-one Chemical compound O1C(CO)=CC(=O)C(OCC=2C=CC=CC=2)=C1 ZGEXYNBHYVEWKT-UHFFFAOYSA-N 0.000 description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- 229930182555 Penicillin Natural products 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 150000002429 hydrazines Chemical class 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 150000002960 penicillins Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 239000008259 solid foam Substances 0.000 description 4
- 125000000335 thiazolyl group Chemical group 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 3
- QRZDXXAAUDLHLS-UHFFFAOYSA-N 1-benzyl-2-(chloromethyl)-5-phenylmethoxypyridin-4-one Chemical compound C=1N(CC=2C=CC=CC=2)C(CCl)=CC(=O)C=1OCC1=CC=CC=C1 QRZDXXAAUDLHLS-UHFFFAOYSA-N 0.000 description 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- MWHFMAMJIYHCLW-UHFFFAOYSA-N 3-phenylmethoxypyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=C1OCC1=CC=CC=C1 MWHFMAMJIYHCLW-UHFFFAOYSA-N 0.000 description 3
- IWJLZADTSIIYBX-UHFFFAOYSA-N 5-(benzyloxy)-2-(hydroxymethyl)-1,4-dihydropyridin-4-one Chemical compound N1C(CO)=CC(=O)C(OCC=2C=CC=CC=2)=C1 IWJLZADTSIIYBX-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 101150052863 THY1 gene Proteins 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 150000001540 azides Chemical class 0.000 description 3
- LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- 230000009935 nitrosation Effects 0.000 description 3
- 238000007034 nitrosation reaction Methods 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 150000003952 β-lactams Chemical class 0.000 description 3
- PODSUMUEKRUDEI-UHFFFAOYSA-N 1-(2-aminoethyl)imidazolidin-2-one Chemical compound NCCN1CCNC1=O PODSUMUEKRUDEI-UHFFFAOYSA-N 0.000 description 2
- WILQNAKOSCMYFK-UHFFFAOYSA-N 1-(chloromethyl)-3-phenylmethoxypyridin-4-one;hydrochloride Chemical compound Cl.ClCN1C=CC(=O)C(OCC=2C=CC=CC=2)=C1 WILQNAKOSCMYFK-UHFFFAOYSA-N 0.000 description 2
- ILVHRPSTCQMRSY-UHFFFAOYSA-N 1-aminopiperazine-2,3-dione Chemical compound NN1CCNC(=O)C1=O ILVHRPSTCQMRSY-UHFFFAOYSA-N 0.000 description 2
- MAXMIIXSFGCZJY-UHFFFAOYSA-N 1-benzyl-4-oxo-5-phenylmethoxypyridine-2-carboxylic acid Chemical compound C=1N(CC=2C=CC=CC=2)C(C(=O)O)=CC(=O)C=1OCC1=CC=CC=C1 MAXMIIXSFGCZJY-UHFFFAOYSA-N 0.000 description 2
- NUWSROZTGBWJGI-UHFFFAOYSA-N 1-tritylpiperazine-2,3-dione Chemical compound O=C1C(=O)NCCN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NUWSROZTGBWJGI-UHFFFAOYSA-N 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 2
- PISMJKGQNDOCGA-UHFFFAOYSA-N 2-(1,3-thiazol-4-yl)acetic acid Chemical compound OC(=O)CC1=CSC=N1 PISMJKGQNDOCGA-UHFFFAOYSA-N 0.000 description 2
- HKZWAHYXIHIFEY-UHFFFAOYSA-N 2-(aminomethyl)-1-benzyl-5-phenylmethoxypyridin-4-one Chemical compound C=1N(CC=2C=CC=CC=2)C(CN)=CC(=O)C=1OCC1=CC=CC=C1 HKZWAHYXIHIFEY-UHFFFAOYSA-N 0.000 description 2
- ZVLYUUNXCFPSCP-UHFFFAOYSA-N 2-(aminomethyl)-5-phenylmethoxy-3h-pyridin-4-one Chemical compound O=C1CC(CN)=NC=C1OCC1=CC=CC=C1 ZVLYUUNXCFPSCP-UHFFFAOYSA-N 0.000 description 2
- NLUZBFODWQDOOB-UHFFFAOYSA-N 2-(azidomethyl)-5-(phenoxymethyl)-1h-pyridin-4-one Chemical compound N1C(CN=[N+]=[N-])=CC(=O)C(COC=2C=CC=CC=2)=C1 NLUZBFODWQDOOB-UHFFFAOYSA-N 0.000 description 2
- JEXFBZSAKIURDS-UHFFFAOYSA-N 2-(azidomethyl)-5-phenylmethoxy-1h-pyridin-4-one Chemical compound N1C(CN=[N+]=[N-])=CC(=O)C(OCC=2C=CC=CC=2)=C1 JEXFBZSAKIURDS-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 2
- NXJZQSRAFBHNLI-UHFFFAOYSA-N 2-oxoimidazolidine-1-carbonyl chloride Chemical compound ClC(=O)N1CCNC1=O NXJZQSRAFBHNLI-UHFFFAOYSA-N 0.000 description 2
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 2
- GCBWDZYSLVSRRI-UHFFFAOYSA-N 3-aminoazetidin-2-one Chemical compound NC1CNC1=O GCBWDZYSLVSRRI-UHFFFAOYSA-N 0.000 description 2
- NVEQKTJCRXBWHS-UHFFFAOYSA-N 3-azidoazetidin-2-one Chemical compound [N-]=[N+]=NC1CNC1=O NVEQKTJCRXBWHS-UHFFFAOYSA-N 0.000 description 2
- ZCUUVWCJGRQCMZ-UHFFFAOYSA-N 3-hydroxypyridin-4(1H)-one Chemical compound OC1=CC=NC=C1O ZCUUVWCJGRQCMZ-UHFFFAOYSA-N 0.000 description 2
- WYLVNASPZUFUJS-UHFFFAOYSA-N 3-phenylmethoxypyridine-2-carbaldehyde Chemical compound O=CC1=NC=CC=C1OCC1=CC=CC=C1 WYLVNASPZUFUJS-UHFFFAOYSA-N 0.000 description 2
- LKAICDYIYAEMNK-UHFFFAOYSA-N 4-methylbenzenesulfonate;pyridin-1-ium-2-ol Chemical compound O=C1C=CC=CN1.CC1=CC=C(S(O)(=O)=O)C=C1 LKAICDYIYAEMNK-UHFFFAOYSA-N 0.000 description 2
- IEDZXMPDRSEYCZ-UHFFFAOYSA-N 4-oxo-5-phenylmethoxy-1h-pyridine-2-carbohydrazide Chemical compound N1C(C(=O)NN)=CC(=O)C(OCC=2C=CC=CC=2)=C1 IEDZXMPDRSEYCZ-UHFFFAOYSA-N 0.000 description 2
- VZSOLQXJYRJEMM-UHFFFAOYSA-N 4-oxo-n-(2-oxoimidazolidin-1-yl)-5-phenylmethoxy-1h-pyridine-2-carboxamide Chemical compound C=1C(=O)C(OCC=2C=CC=CC=2)=CNC=1C(=O)NN1CCNC1=O VZSOLQXJYRJEMM-UHFFFAOYSA-N 0.000 description 2
- NTWXQDISUWBDPV-UHFFFAOYSA-N 5-hydroxy-4-oxo-1h-pyridine-2-carbaldehyde Chemical compound OC1=CNC(C=O)=CC1=O NTWXQDISUWBDPV-UHFFFAOYSA-N 0.000 description 2
- SCFDEORBGQKORJ-UHFFFAOYSA-N 5-hydroxy-4-oxo-n-(2-oxoimidazolidin-1-yl)-1h-pyridine-2-carboxamide Chemical compound O=C1C(O)=CNC(C(=O)NN2C(NCC2)=O)=C1 SCFDEORBGQKORJ-UHFFFAOYSA-N 0.000 description 2
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 2
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 241001529251 Gallinago gallinago Species 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- IVVPRJNZVRCZGB-UHFFFAOYSA-N N-(2-aminoethyl)-5-hydroxy-4-oxo-1H-pyridine-2-carboxamide dihydrochloride Chemical compound NCCNC(=O)C=1NC=C(C(C1)=O)O.Cl.Cl IVVPRJNZVRCZGB-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- LNCZMASXOCFBJK-UHFFFAOYSA-N benzhydryl cyclopentanecarboxylate Chemical compound C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(=O)C1CCCC1 LNCZMASXOCFBJK-UHFFFAOYSA-N 0.000 description 2
- WVVSMQGGICZYSZ-UHFFFAOYSA-N benzyl 3-phenylmethoxypyridine-2-carboxylate Chemical compound N=1C=CC=C(OCC=2C=CC=CC=2)C=1C(=O)OCC1=CC=CC=C1 WVVSMQGGICZYSZ-UHFFFAOYSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical compound OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 description 2
- WZNJWVWKTVETCG-UHFFFAOYSA-N kojic acid Natural products OC(=O)C(N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 2
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000005646 oximino group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- JTHRRMFZHSDGNJ-UHFFFAOYSA-N piperazine-2,3-dione Chemical compound O=C1NCCNC1=O JTHRRMFZHSDGNJ-UHFFFAOYSA-N 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- NLARCUDOUOQRPB-RUDMXATFSA-N (2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetic acid Chemical compound CO\N=C(\C(O)=O)C1=CSC(N)=N1 NLARCUDOUOQRPB-RUDMXATFSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- TWUVPYBVZUYZLH-UHFFFAOYSA-N 1,3-diaminoimidazolidin-2-one Chemical class NN1CCN(N)C1=O TWUVPYBVZUYZLH-UHFFFAOYSA-N 0.000 description 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
- PDYXYAQZKOOFSP-UHFFFAOYSA-N 1-benzyl-2-(chloromethyl)-5-phenylmethoxypyridin-4-one hydrochloride Chemical compound Cl.ClCc1cc(=O)c(OCc2ccccc2)cn1Cc1ccccc1 PDYXYAQZKOOFSP-UHFFFAOYSA-N 0.000 description 1
- JFBAXQZJXCIYEF-UHFFFAOYSA-N 1-benzyl-2-(hydroxymethyl)-5-phenylmethoxypyridin-4-one Chemical compound C=1N(CC=2C=CC=CC=2)C(CO)=CC(=O)C=1OCC1=CC=CC=C1 JFBAXQZJXCIYEF-UHFFFAOYSA-N 0.000 description 1
- BZBBXVLXVOZFRH-UHFFFAOYSA-N 1-benzylpyridin-4-one Chemical compound C1=CC(=O)C=CN1CC1=CC=CC=C1 BZBBXVLXVOZFRH-UHFFFAOYSA-N 0.000 description 1
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
- GHKFQHNOAJTZCF-UHFFFAOYSA-N 1-methyl-3-phenylmethoxypyridin-4-one Chemical compound CN1C=CC(=O)C(OCC=2C=CC=CC=2)=C1 GHKFQHNOAJTZCF-UHFFFAOYSA-N 0.000 description 1
- YFMLAZBUXVEFHJ-UHFFFAOYSA-N 2,2,2-trifluoro-N-silylacetamide Chemical compound FC(F)(F)C(=O)N[SiH3] YFMLAZBUXVEFHJ-UHFFFAOYSA-N 0.000 description 1
- QLPZEDHKVHQPAD-UHFFFAOYSA-N 2,2,2-trifluoro-n-trimethylsilylacetamide Chemical compound C[Si](C)(C)NC(=O)C(F)(F)F QLPZEDHKVHQPAD-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- LTIAISOLFAANNB-UHFFFAOYSA-N 2-(1-benzyl-4-oxo-5-phenylmethoxypyridin-2-yl)acetonitrile Chemical compound C1=C(OCC=2C=CC=CC=2)C(=O)C=C(CC#N)N1CC1=CC=CC=C1 LTIAISOLFAANNB-UHFFFAOYSA-N 0.000 description 1
- LJUFWZQRDABBTO-UHFFFAOYSA-N 2-(1-benzyl-5-hydroxy-4-oxopyridin-2-yl)-n-(2-oxoimidazolidin-1-yl)acetamide Chemical compound C1CNC(=O)N1NC(=O)CC1=CC(=O)C(O)=CN1CC1=CC=CC=C1 LJUFWZQRDABBTO-UHFFFAOYSA-N 0.000 description 1
- WAIAKIHTKCUWEP-UHFFFAOYSA-N 2-(1-benzyl-5-hydroxy-4-oxopyridin-2-yl)acetic acid Chemical compound OC(=O)CC1=CC(=O)C(O)=CN1CC1=CC=CC=C1 WAIAKIHTKCUWEP-UHFFFAOYSA-N 0.000 description 1
- OOYGSFOGFJDDHP-UHFFFAOYSA-N 2-(aminomethyl)-6-[4,6-diamino-3-[4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol;sulfuric acid Chemical compound OS(O)(=O)=O.OC1C(O)C(O)C(CN)OC1OC1C(O)C(OC2C(C(N)C(O)C(CO)O2)O)C(N)CC1N OOYGSFOGFJDDHP-UHFFFAOYSA-N 0.000 description 1
- AUOGGZMEEHWEMY-UHFFFAOYSA-N 2-(azidomethyl)-1-benzyl-5-phenylmethoxypyridin-4-one Chemical compound C=1N(CC=2C=CC=CC=2)C(CN=[N+]=[N-])=CC(=O)C=1OCC1=CC=CC=C1 AUOGGZMEEHWEMY-UHFFFAOYSA-N 0.000 description 1
- VNQBCNKTIHUZQT-UHFFFAOYSA-N 2-(chloromethyl)-5-phenylmethoxy-1h-pyridin-4-one;hydrochloride Chemical compound Cl.N1C(CCl)=CC(=O)C(OCC=2C=CC=CC=2)=C1 VNQBCNKTIHUZQT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- MUXYPCOHLFTZJG-UHFFFAOYSA-N 2-[hydroxy(methoxy)methyl]-5-phenylmethoxy-1h-pyridin-4-one Chemical compound N1C(C(O)OC)=CC(=O)C(OCC=2C=CC=CC=2)=C1 MUXYPCOHLFTZJG-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 150000008625 2-imidazolidinones Chemical class 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- QFZTUWOWMRNMAH-UHFFFAOYSA-N 2h-pyran-2-carboxylic acid Chemical compound OC(=O)C1OC=CC=C1 QFZTUWOWMRNMAH-UHFFFAOYSA-N 0.000 description 1
- QUKFBBRMZXGYBK-UHFFFAOYSA-N 3-ethylpyridine-2-carboxamide Chemical compound CCC1=CC=CN=C1C(N)=O QUKFBBRMZXGYBK-UHFFFAOYSA-N 0.000 description 1
- QGFZHCCZNXHVDB-UHFFFAOYSA-N 3-hydroxy-4-oxo-3H-pyridine-2-carboxamide Chemical compound OC1C(=NC=CC1=O)C(=O)N QGFZHCCZNXHVDB-UHFFFAOYSA-N 0.000 description 1
- KHKMKPMVKSVVMC-UHFFFAOYSA-N 3-phenylmethoxypyridine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=C1OCC1=CC=CC=C1 KHKMKPMVKSVVMC-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- QRCNLMIBDQGEHC-UHFFFAOYSA-N 4-oxo-3H-pyridine-2-carboxamide Chemical compound C(N)(=O)C1=NC=CC(C1)=O QRCNLMIBDQGEHC-UHFFFAOYSA-N 0.000 description 1
- RGZZNPNSZZJJSH-UHFFFAOYSA-N 4-oxo-5-phenylmethoxypyran-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC(=O)C(OCC=2C=CC=CC=2)=C1 RGZZNPNSZZJJSH-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- KIDVXDFSLNXGEA-UHFFFAOYSA-N 5-hydroxy-4-oxo-1h-pyridine-2-carbohydrazide Chemical compound NNC(=O)C1=CC(=O)C(O)=CN1 KIDVXDFSLNXGEA-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- 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 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101100148830 Arabidopsis thaliana SCI1 gene Proteins 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- CYHZTCBOALXIJO-UHFFFAOYSA-L C(C(C)C)(=O)[O-].C(C(C)C)(=O)[O-].[Na+].[Na+] Chemical compound C(C(C)C)(=O)[O-].C(C(C)C)(=O)[O-].[Na+].[Na+] CYHZTCBOALXIJO-UHFFFAOYSA-L 0.000 description 1
- WJFVUBKNSREWHF-UHFFFAOYSA-N C(N)(OCC1=CC=CC=C1)=O.[Na] Chemical compound C(N)(OCC1=CC=CC=C1)=O.[Na] WJFVUBKNSREWHF-UHFFFAOYSA-N 0.000 description 1
- CXLAXPSGWNHBFE-UHFFFAOYSA-N CC1=C(C(=O)C(=CN1CC2=CC=CC=C2)OCC3=CC=CC=C3)N4CCNC4=O Chemical compound CC1=C(C(=O)C(=CN1CC2=CC=CC=C2)OCC3=CC=CC=C3)N4CCNC4=O CXLAXPSGWNHBFE-UHFFFAOYSA-N 0.000 description 1
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- LXWBXEWUSAABOA-UHFFFAOYSA-N Cephamycin-C Natural products S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)C(OC)(NC(=O)CCCC(N)C(O)=O)C21 LXWBXEWUSAABOA-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- YMEMQHRQAVYSMQ-UHFFFAOYSA-N N-(2-aminoethyl)-5-hydroxy-4-oxo-1H-pyridine-2-carboxamide 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.NCCNC(=O)c1cc(=O)c(O)c[nH]1 YMEMQHRQAVYSMQ-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- KGKHLWVVGNKHCW-UHFFFAOYSA-N O=C(NC(C(N1)=C=O)C1=O)OCC1=CC=CC=C1 Chemical compound O=C(NC(C(N1)=C=O)C1=O)OCC1=CC=CC=C1 KGKHLWVVGNKHCW-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- 101100054266 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) SNF4 gene Proteins 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920006328 Styrofoam Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- BYHXLDZDSZVDJH-UHFFFAOYSA-N acetic acid;1,3-thiazole Chemical compound CC(O)=O.C1=CSC=N1 BYHXLDZDSZVDJH-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000005276 alkyl hydrazino group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000005100 aryl amino carbonyl group Chemical group 0.000 description 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 1
- PPVWKLLLMBEYBH-UHFFFAOYSA-N azetidine-1-carboxamide 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.N1(CCC1)C(=O)N PPVWKLLLMBEYBH-UHFFFAOYSA-N 0.000 description 1
- 150000001539 azetidines Chemical class 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- NNVNDLCNXISESU-UHFFFAOYSA-N benzyl 4,5-bis(phenylmethoxy)pyridine-2-carboxylate Chemical compound C=1C(OCC=2C=CC=CC=2)=C(OCC=2C=CC=CC=2)C=NC=1C(=O)OCC1=CC=CC=C1 NNVNDLCNXISESU-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- NQXRQYKIEKLAHI-UHFFFAOYSA-N benzyl n-(2-oxoazetidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CNC1=O NQXRQYKIEKLAHI-UHFFFAOYSA-N 0.000 description 1
- NLIIGHUGRWVWMF-WPRPVWTQSA-N benzyl n-[(2s,3s)-2-methyl-4-oxoazetidin-3-yl]carbamate Chemical compound C[C@@H]1NC(=O)[C@H]1NC(=O)OCC1=CC=CC=C1 NLIIGHUGRWVWMF-WPRPVWTQSA-N 0.000 description 1
- 238000005574 benzylation reaction Methods 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- LXWBXEWUSAABOA-VXSYNFHWSA-N cephamycin C Chemical compound S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)[C@@](OC)(NC(=O)CCC[C@@H](N)C(O)=O)[C@H]21 LXWBXEWUSAABOA-VXSYNFHWSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 230000003009 desulfurizing effect Effects 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- CBQZVPOKZXSMDA-UHFFFAOYSA-N ethyl acetate;n-(oxomethylidene)sulfamoyl chloride Chemical compound CCOC(C)=O.ClS(=O)(=O)N=C=O CBQZVPOKZXSMDA-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002332 glycine derivatives Chemical class 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XOAYKINYVYDPDF-UHFFFAOYSA-N imidazolidine-1-carboxylic acid Chemical compound OC(=O)N1CCNC1 XOAYKINYVYDPDF-UHFFFAOYSA-N 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- JGCLDEFBULMSDY-UHFFFAOYSA-N n-(2,3-dioxopiperazin-1-yl)-4,5-bis(phenylmethoxy)pyridine-2-carboxamide Chemical compound C=1C(OCC=2C=CC=CC=2)=C(OCC=2C=CC=CC=2)C=NC=1C(=O)NN1CCNC(=O)C1=O JGCLDEFBULMSDY-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 125000002071 phenylalkoxy group Chemical group 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 208000020029 respiratory tract infectious disease Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008261 styrofoam Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- VIYXXANHGYSBLY-UHFFFAOYSA-N trimethylsilyl 2,2,2-trifluoroacetate Chemical compound C[Si](C)(C)OC(=O)C(F)(F)F VIYXXANHGYSBLY-UHFFFAOYSA-N 0.000 description 1
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical class [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78047985A | 1985-09-26 | 1985-09-26 | |
| US78047985 | 1985-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8602446A true NL8602446A (nl) | 1987-04-16 |
Family
ID=25119699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8602446A NL8602446A (nl) | 1985-09-26 | 1986-09-26 | 2-oxo-1-(gesubstitueerd sulfonyl)aminocarbonylazetidinen. |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS6284082A (cs) |
| KR (1) | KR900001013B1 (cs) |
| CN (1) | CN86106980A (cs) |
| AT (1) | ATA257986A (cs) |
| AU (1) | AU600912B2 (cs) |
| BE (1) | BE905502A (cs) |
| CA (1) | CA1308719C (cs) |
| CH (1) | CH670828A5 (cs) |
| DD (1) | DD250121A5 (cs) |
| DE (1) | DE3632876A1 (cs) |
| DK (1) | DK460386A (cs) |
| EG (1) | EG18314A (cs) |
| ES (1) | ES2001995A6 (cs) |
| FI (1) | FI863890A7 (cs) |
| FR (1) | FR2587700B1 (cs) |
| GB (1) | GB2181130B (cs) |
| GR (1) | GR862449B (cs) |
| HU (1) | HU198044B (cs) |
| IE (1) | IE59686B1 (cs) |
| IL (1) | IL80160A (cs) |
| IT (1) | IT1214533B (cs) |
| LU (1) | LU86611A1 (cs) |
| NL (1) | NL8602446A (cs) |
| NO (1) | NO863837L (cs) |
| NZ (1) | NZ217704A (cs) |
| PH (1) | PH23315A (cs) |
| PL (1) | PL151546B1 (cs) |
| PT (1) | PT83440B (cs) |
| SE (1) | SE8604089L (cs) |
| YU (1) | YU46177B (cs) |
| ZA (1) | ZA867373B (cs) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987007273A2 (en) * | 1986-05-23 | 1987-12-03 | The Upjohn Company | N-1 substituted sulfonylaminocarbonyl, c-4 substituted monobactams |
| US5006650A (en) * | 1987-02-11 | 1991-04-09 | The Upjohn Company | Novel N-1 substituted beta-lactams as antibiotics |
| KR890700588A (ko) * | 1987-02-11 | 1989-04-25 | 로버어트 에이 아미테이지 | 항생 물질로서 신규 N-1 치환된 β -락탐 |
| KR890700586A (ko) * | 1987-02-27 | 1989-04-25 | 로버어트 에이 아마테이지 | 피리돈 카르복실산 또는 산유도체를 함유하는 항균제 베타-락탐 |
| CA1317298C (en) * | 1987-03-03 | 1993-05-04 | Upjohn Company (The) | Antibiotic sulfonylaminocarbonyl activated .beta.-lactams |
| US4772693A (en) * | 1987-07-01 | 1988-09-20 | E. R. Squibb & Sons, Inc. | 2-oxo-1-((Substituted sulfonyl)amino)-carbonyl)azetidines |
| US4762922A (en) * | 1987-07-01 | 1988-08-09 | Squibb Corporation | 2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines |
| US5015737A (en) * | 1987-07-22 | 1991-05-14 | The Upjohn Company | Therapeutically useful beta-lactams |
| JPH02504272A (ja) * | 1987-07-22 | 1990-12-06 | ジ・アップジョン・カンパニー | 治療上有用なβ‐ラクタム類 |
| US4777252A (en) * | 1987-08-13 | 1988-10-11 | E. R. Squibb & Sons, Inc. | 2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines |
| US4889930A (en) * | 1987-12-21 | 1989-12-26 | E. R. Squibb & Sons, Inc. | Process for making 2-oxo-1-((substituted sulfonyl)amino)carbonzyl)azetidines and intermediates used therein |
| US4871841A (en) * | 1987-12-23 | 1989-10-03 | E. R. Squibb & Sons, Inc. | 2-Oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines |
| EP0336667A3 (en) * | 1988-04-04 | 1991-04-10 | E.R. Squibb & Sons, Inc. | [3S(Z)]-3-[[(2-amino-4-thiazolyl)[[2-(hydroxyamino)-2-oxoethoxy]imino]acetyl]-amino]-2,2-dimethyl-4-oxo-1-azetidinyl sulfate |
| US4959470A (en) * | 1988-08-17 | 1990-09-25 | E. R. Squibb & Sons, Inc. | 2-oxo-[[(substituted sulfonyl)-amino]carbonyl]-azetidines |
| ATE180474T1 (de) * | 1992-12-23 | 1999-06-15 | Novartis Ag | Imidazol-derivate und ihre verwendung als agrochemische mittel |
| EP0671654B1 (en) * | 1994-03-11 | 1997-09-10 | Agfa-Gevaert N.V. | Photographic material containing a new type of hydrazide |
| EP1698375B1 (en) * | 2003-12-25 | 2014-04-02 | Ono Pharmaceutical Co., Ltd. | Azetidine ring compounds and drugs comprising the same |
| GB201111704D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Novel compounds |
| GB201111705D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Compounds and their use |
| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| AP2014007637A0 (en) * | 2011-11-15 | 2014-05-31 | Takeda Pharmaceutical | Dihydroxy aromatic heterocyclic compound |
| GB201222711D0 (en) | 2012-12-17 | 2013-01-30 | Takeda Pharmaceutical | Novel compounds |
| CN106986820B (zh) * | 2017-02-24 | 2019-05-21 | 浙江工商大学 | 多功能的羟基吡啶酮衍生物及其水合物的制备法和用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ199981A (en) * | 1981-04-09 | 1985-08-16 | Squibb & Sons Inc | 2-oxo-1-(((substituted sulphonyl)amino)carbonyl)azetidines |
| CA1272726C (en) * | 1982-01-04 | 1990-08-14 | 2-oxo-1-(aminocarbonylaminosulfonyl- aminocarbonyl)azetidines | |
| US4939253A (en) * | 1982-08-04 | 1990-07-03 | E. R. Squibb & Sons, Inc. | 2-oxoazetidin-1-yloxy acetic acids and analogs |
| US4801705A (en) * | 1986-06-23 | 1989-01-31 | E. R. Squibb & Sons, Inc. | 2-oxo-1-(((substituted sulfonyl)amino)-carbonyl)azetidines |
-
1986
- 1986-09-25 EG EG603/86A patent/EG18314A/xx active
- 1986-09-26 AU AU63156/86A patent/AU600912B2/en not_active Ceased
- 1986-09-26 CA CA000519170A patent/CA1308719C/en not_active Expired - Lifetime
- 1986-09-26 CH CH3860/86A patent/CH670828A5/fr not_active IP Right Cessation
- 1986-09-26 SE SE8604089A patent/SE8604089L/xx not_active Application Discontinuation
- 1986-09-26 DE DE19863632876 patent/DE3632876A1/de not_active Ceased
- 1986-09-26 DK DK460386A patent/DK460386A/da not_active Application Discontinuation
- 1986-09-26 ZA ZA867373A patent/ZA867373B/xx unknown
- 1986-09-26 KR KR1019860008067A patent/KR900001013B1/ko not_active Expired
- 1986-09-26 NL NL8602446A patent/NL8602446A/nl active Search and Examination
- 1986-09-26 DD DD86295013A patent/DD250121A5/de not_active IP Right Cessation
- 1986-09-26 YU YU165986A patent/YU46177B/sh unknown
- 1986-09-26 ES ES8602204A patent/ES2001995A6/es not_active Expired
- 1986-09-26 BE BE0/217217A patent/BE905502A/fr not_active IP Right Cessation
- 1986-09-26 HU HU864124A patent/HU198044B/hu not_active IP Right Cessation
- 1986-09-26 PL PL1986261575A patent/PL151546B1/pl unknown
- 1986-09-26 GB GB8623151A patent/GB2181130B/en not_active Expired
- 1986-09-26 NO NO863837A patent/NO863837L/no unknown
- 1986-09-26 IE IE254786A patent/IE59686B1/en not_active IP Right Cessation
- 1986-09-26 IT IT8621834A patent/IT1214533B/it active
- 1986-09-26 IL IL80160A patent/IL80160A/xx not_active IP Right Cessation
- 1986-09-26 AT AT0257986A patent/ATA257986A/de not_active Application Discontinuation
- 1986-09-26 LU LU86611A patent/LU86611A1/fr unknown
- 1986-09-26 FI FI863890A patent/FI863890A7/fi not_active Application Discontinuation
- 1986-09-26 PH PH34303A patent/PH23315A/en unknown
- 1986-09-26 FR FR8613466A patent/FR2587700B1/fr not_active Expired
- 1986-09-26 CN CN198686106980A patent/CN86106980A/zh active Pending
- 1986-09-26 JP JP61229474A patent/JPS6284082A/ja active Pending
- 1986-09-26 GR GR862449A patent/GR862449B/el unknown
- 1986-09-26 PT PT83440A patent/PT83440B/pt unknown
-
1988
- 1988-09-26 NZ NZ217704A patent/NZ217704A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NL8602446A (nl) | 2-oxo-1-(gesubstitueerd sulfonyl)aminocarbonylazetidinen. | |
| US4576749A (en) | 3-Acylamino-1-carboxymethylaminocarbonyl-2-azetidinones | |
| US4581170A (en) | N-hydroxyl protecting groups and process and intermediates for the preparation of 3-acylamino-1-hydroxy-2-azetidinones | |
| CA1246572A (en) | 2-oxo-1-[[(substituted sulfonyl)amino]- carbonyl]azetidines | |
| US4633017A (en) | N-hydroxy protecting groups and process for the preparation of 3-acylamino-1-hydroxy-2-azetidinones | |
| JPH0368021B2 (cs) | ||
| EP0303286A1 (en) | 2-Oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines | |
| JPH01305081A (ja) | ３―アシルアミノ―１―［［［（置換スルホニル）アミノ〕カルボニル〕アミノ〕―２―アゼチジノン類 | |
| JPS588060A (ja) | アリ−ルチオアゼチジノンスルホン酸塩類 | |
| US4959470A (en) | 2-oxo-[[(substituted sulfonyl)-amino]carbonyl]-azetidines | |
| EP0420069A2 (en) | Heterocyclic hydrazide derivatives of monocyclic beta-lactam antibiotics | |
| JPS6023363A (ja) | Ｎ−（置換メチル）−アゼチジン−２−オン類 | |
| US4889930A (en) | Process for making 2-oxo-1-((substituted sulfonyl)amino)carbonzyl)azetidines and intermediates used therein | |
| CA1323029C (en) | 2-oxo-1-[(substituted sulfonyl)amino]carbonyl]azetidines | |
| JPS5988462A (ja) | アゼチジニルスルホン酸およびその類縁体 | |
| US5106977A (en) | Intermediates for a process for making 2-oxo-1-[[(substituted sulfonyl)-amino]carbonyl]azetidines | |
| NZ199828A (en) | 4-substituted mercapto-2-oxo-1-azetidine-sulphonic acid derivatives and pharmaceutical compositions | |
| EP0127177B1 (en) | [[(3-Acylamino-2-oxo-1-azetidinyl)oxy]methyl]phosphinic acids | |
| US4980465A (en) | Process for making 2-oxo-1-[[(substituted sulfonyl)-amino]carbonyl)] azetidines and intermediates used therein | |
| US5068331A (en) | Certain (2-carboxy or 2-propenoic or 2-carbonyl)-3-halo-4,5-dioxy pyridine intermediates and the corresponding 1,4-dihydro-4-pyridones) | |
| EP0015771A1 (en) | N-(6-((acylaminoacylamino or aminoacylamino)phenyl)-1,2-dihydro-2-oxonicotinyl) cephalosporin compounds, processes for their production, and compositions containing the same | |
| JPS6094958A (ja) | アゼチジノン類 | |
| JPS5930716B2 (ja) | 抗生物質の製造方法 | |
| HK1088003B (en) | 3-substituted 5,6-diaryl-pyrazine-2-carboxamide and-2-sulfonamide derivatives as cb1 modulators |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BN | A decision not to publish the application has become irrevocable |