HU198044B - Process for production of 2-oxo-1-/(substituated sulphonil)-/amin/-carbonil)-asetidines and medical preparatives containing these substances - Google Patents
Process for production of 2-oxo-1-/(substituated sulphonil)-/amin/-carbonil)-asetidines and medical preparatives containing these substances Download PDFInfo
- Publication number
- HU198044B HU198044B HU864124A HU412486A HU198044B HU 198044 B HU198044 B HU 198044B HU 864124 A HU864124 A HU 864124A HU 412486 A HU412486 A HU 412486A HU 198044 B HU198044 B HU 198044B
- Authority
- HU
- Hungary
- Prior art keywords
- oxo
- amino
- mmol
- added
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 239000000126 substance Substances 0.000 title description 3
- -1 (2-oxo-1-imidazolidinyl) methyl Chemical group 0.000 claims description 125
- 150000001875 compounds Chemical class 0.000 claims description 115
- 125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 206010029897 Obsessive thoughts Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001539 azetidines Chemical class 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052736 halogen Chemical group 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 136
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 114
- 239000000243 solution Substances 0.000 description 109
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 87
- 239000000203 mixture Substances 0.000 description 82
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 79
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 73
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 238000003756 stirring Methods 0.000 description 62
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 48
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 32
- 239000000725 suspension Substances 0.000 description 31
- 239000000047 product Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 23
- 239000002244 precipitate Substances 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 14
- 239000012043 crude product Substances 0.000 description 14
- 238000010511 deprotection reaction Methods 0.000 description 14
- 239000005457 ice water Substances 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 8
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 8
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 150000003952 β-lactams Chemical class 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 7
- 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 7
- 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 7
- 238000001035 drying Methods 0.000 description 7
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
- 239000012434 nucleophilic reagent Substances 0.000 description 7
- DDGMPNJQMZYCGV-UHFFFAOYSA-N 2-amino-5-hydroxy-1h-pyridin-4-one Chemical compound NC1=CC(=O)C(O)=CN1 DDGMPNJQMZYCGV-UHFFFAOYSA-N 0.000 description 6
- 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 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 6
- NQXRQYKIEKLAHI-VIFPVBQESA-N benzyl n-[(3s)-2-oxoazetidin-3-yl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)N[C@H]1CNC1=O NQXRQYKIEKLAHI-VIFPVBQESA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 239000003039 volatile agent Substances 0.000 description 6
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 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
- 238000005406 washing Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- DHIVBEZCBBHIPZ-UHFFFAOYSA-N 1-aminoimidazolidin-2-one Chemical compound NN1CCNC1=O DHIVBEZCBBHIPZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 3
- ZCUUVWCJGRQCMZ-UHFFFAOYSA-N 3-hydroxypyridin-4(1H)-one Chemical group OC1=CC=NC=C1O ZCUUVWCJGRQCMZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000013058 crude material Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 3
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 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
- 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 2
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 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
- 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 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
- 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 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-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
- 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 2
- RAFXAEJBIFWFJJ-UHFFFAOYSA-N 5-hydroxy-2-[(2-oxoimidazolidin-1-yl)methyl]-1h-pyridin-4-one Chemical compound O=C1C(O)=CNC(CN2C(NCC2)=O)=C1 RAFXAEJBIFWFJJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000124008 Mammalia Species 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
- 229930182555 Penicillin Natural products 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-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
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78047985A | 1985-09-26 | 1985-09-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT44535A HUT44535A (en) | 1988-03-28 |
| HU198044B true HU198044B (en) | 1989-07-28 |
Family
ID=25119699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU864124A HU198044B (en) | 1985-09-26 | 1986-09-26 | Process for production of 2-oxo-1-/(substituated sulphonil)-/amin/-carbonil)-asetidines and medical preparatives containing these substances |
Country Status (31)
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0308416A1 (en) * | 1986-05-23 | 1989-03-29 | The Upjohn Company | N-1 substituted sulfonylaminocarbonyl, c-4 substituted monobactams |
| WO1988006156A1 (en) * | 1987-02-11 | 1988-08-25 | The Upjohn Company | NOVEL N-1 SUBSTITUTED beta-LACTAMS AS ANTIBIOTICS |
| US5006650A (en) * | 1987-02-11 | 1991-04-09 | The Upjohn Company | Novel N-1 substituted beta-lactams as antibiotics |
| AU600094B2 (en) * | 1987-02-27 | 1990-08-02 | Upjohn Company, The | Antibiotic 2- azetidinones have pyrid -4- one 2-yl- carbonylamino-1-imidazolid-2-one-3-yl sulfonylaminocarbonyl groups at N-1 |
| CA1317298C (en) * | 1987-03-03 | 1993-05-04 | Upjohn Company (The) | Antibiotic sulfonylaminocarbonyl activated .beta.-lactams |
| US4762922A (en) * | 1987-07-01 | 1988-08-09 | Squibb Corporation | 2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines |
| US4772693A (en) * | 1987-07-01 | 1988-09-20 | E. R. Squibb & Sons, Inc. | 2-oxo-1-((Substituted sulfonyl)amino)-carbonyl)azetidines |
| KR890701588A (ko) * | 1987-07-22 | 1989-12-21 | 로버어트 에이 아미테이지 | 치료학적으로 유용한 β-락탐 |
| US5015737A (en) * | 1987-07-22 | 1991-05-14 | The Upjohn Company | Therapeutically useful beta-lactams |
| 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 |
| JPH01290674A (ja) * | 1988-04-04 | 1989-11-22 | E R Squibb & Sons Inc | アゼチジニル誘導体 |
| 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 |
| DE69405535T2 (de) * | 1994-03-11 | 1998-04-02 | Agfa Gevaert Nv | Photographisches Material, das einen neuen Typ eines Hydrazides enthält |
| 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 NO NO863837A patent/NO863837L/no unknown
- 1986-09-26 JP JP61229474A patent/JPS6284082A/ja active Pending
- 1986-09-26 GR GR862449A patent/GR862449B/el unknown
- 1986-09-26 KR KR1019860008067A patent/KR900001013B1/ko not_active Expired
- 1986-09-26 IT IT8621834A patent/IT1214533B/it active
- 1986-09-26 AT AT0257986A patent/ATA257986A/de not_active Application Discontinuation
- 1986-09-26 DE DE19863632876 patent/DE3632876A1/de not_active Ceased
- 1986-09-26 NL NL8602446A patent/NL8602446A/nl active Search and Examination
- 1986-09-26 HU HU864124A patent/HU198044B/hu not_active IP Right Cessation
- 1986-09-26 DK DK460386A patent/DK460386A/da not_active Application Discontinuation
- 1986-09-26 BE BE0/217217A patent/BE905502A/fr not_active IP Right Cessation
- 1986-09-26 LU LU86611A patent/LU86611A1/fr unknown
- 1986-09-26 IL IL80160A patent/IL80160A/xx not_active IP Right Cessation
- 1986-09-26 GB GB8623151A patent/GB2181130B/en not_active Expired
- 1986-09-26 ZA ZA867373A patent/ZA867373B/xx unknown
- 1986-09-26 IE IE254786A patent/IE59686B1/en not_active IP Right Cessation
- 1986-09-26 CH CH3860/86A patent/CH670828A5/fr not_active IP Right Cessation
- 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 YU YU165986A patent/YU46177B/sh unknown
- 1986-09-26 PL PL1986261575A patent/PL151546B1/pl unknown
- 1986-09-26 CN CN198686106980A patent/CN86106980A/zh active Pending
- 1986-09-26 FI FI863890A patent/FI863890A7/fi not_active Application Discontinuation
- 1986-09-26 PT PT83440A patent/PT83440B/pt unknown
- 1986-09-26 SE SE8604089A patent/SE8604089L/xx not_active Application Discontinuation
- 1986-09-26 PH PH34303A patent/PH23315A/en unknown
- 1986-09-26 ES ES8602204A patent/ES2001995A6/es not_active Expired
- 1986-09-26 FR FR8613466A patent/FR2587700B1/fr not_active Expired
- 1986-09-26 DD DD86295013A patent/DD250121A5/de not_active IP Right Cessation
-
1988
- 1988-09-26 NZ NZ217704A patent/NZ217704A/xx unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |