CN86106980A - 2-氧代-1-{[(取代的磺酰基)-氨基]羰基}氮杂环丁烷类 - Google Patents
2-氧代-1-{[(取代的磺酰基)-氨基]羰基}氮杂环丁烷类 Download PDFInfo
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- CN86106980A CN86106980A CN198686106980A CN86106980A CN86106980A CN 86106980 A CN86106980 A CN 86106980A CN 198686106980 A CN198686106980 A CN 198686106980A CN 86106980 A CN86106980 A CN 86106980A CN 86106980 A CN86106980 A CN 86106980A
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims description 243
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 title claims description 80
- 125000004390 alkyl sulfonyl group Chemical group 0.000 title description 114
- 230000003213 activating effect Effects 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 342
- -1 azido- Chemical class 0.000 claims description 241
- 238000002360 preparation method Methods 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000002252 acyl group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000006371 dihalo methyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 239
- 239000000243 solution Substances 0.000 description 181
- 238000003756 stirring Methods 0.000 description 177
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 139
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 119
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- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 90
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 86
- 229910052760 oxygen Inorganic materials 0.000 description 86
- 239000001301 oxygen Substances 0.000 description 86
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 85
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 83
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- 238000006243 chemical reaction Methods 0.000 description 66
- 239000012043 crude product Substances 0.000 description 62
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 58
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 55
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 53
- 238000010511 deprotection reaction Methods 0.000 description 51
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- 239000012434 nucleophilic reagent Substances 0.000 description 44
- 239000007787 solid Substances 0.000 description 42
- 238000005406 washing Methods 0.000 description 40
- 238000002425 crystallisation Methods 0.000 description 36
- 230000008025 crystallization Effects 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- 239000003643 water by type Substances 0.000 description 34
- 238000001556 precipitation Methods 0.000 description 33
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 32
- 239000000706 filtrate Substances 0.000 description 31
- 239000002585 base Substances 0.000 description 30
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 29
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 28
- 239000002253 acid Substances 0.000 description 27
- 238000001704 evaporation Methods 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 238000000354 decomposition reaction Methods 0.000 description 26
- 238000001914 filtration Methods 0.000 description 25
- 238000007738 vacuum evaporation Methods 0.000 description 25
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
- 229920001577 copolymer Polymers 0.000 description 22
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 21
- 238000001291 vacuum drying Methods 0.000 description 21
- 238000000746 purification Methods 0.000 description 20
- 238000001035 drying Methods 0.000 description 19
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 18
- 235000010290 biphenyl Nutrition 0.000 description 18
- 230000000903 blocking effect Effects 0.000 description 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 18
- 235000011121 sodium hydroxide Nutrition 0.000 description 18
- 239000003153 chemical reaction reagent Substances 0.000 description 17
- 239000000463 material Substances 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 16
- 239000003513 alkali Substances 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 15
- 230000007062 hydrolysis Effects 0.000 description 15
- 238000006460 hydrolysis reaction Methods 0.000 description 15
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 13
- 238000010828 elution Methods 0.000 description 13
- 229910052736 halogen Inorganic materials 0.000 description 13
- 150000002367 halogens Chemical class 0.000 description 13
- 235000011167 hydrochloric acid Nutrition 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 238000000967 suction filtration Methods 0.000 description 13
- 150000001721 carbon Chemical group 0.000 description 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- PISMJKGQNDOCGA-UHFFFAOYSA-N 2-(1,3-thiazol-4-yl)acetic acid Chemical compound OC(=O)CC1=CSC=N1 PISMJKGQNDOCGA-UHFFFAOYSA-N 0.000 description 11
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical class C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 11
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 11
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 230000008878 coupling Effects 0.000 description 11
- 238000010168 coupling process Methods 0.000 description 11
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- 235000019441 ethanol Nutrition 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 229940083608 sodium hydroxide Drugs 0.000 description 11
- 150000003952 β-lactams Chemical class 0.000 description 11
- BZBBXVLXVOZFRH-UHFFFAOYSA-N 1-benzylpyridin-4-one Chemical compound C1=CC(=O)C=CN1CC1=CC=CC=C1 BZBBXVLXVOZFRH-UHFFFAOYSA-N 0.000 description 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 10
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 10
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- 238000006722 reduction reaction Methods 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 9
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 9
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- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical class C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 8
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- 241001465754 Metazoa Species 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- CPQHOTXYSJSUMB-UHFFFAOYSA-L S(=O)(=O)([O-])[O-].[Na+].C(Cl)Cl.[Na+] Chemical compound S(=O)(=O)([O-])[O-].[Na+].C(Cl)Cl.[Na+] CPQHOTXYSJSUMB-UHFFFAOYSA-L 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000545067 Venus Species 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
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- CDMXXXZRZWQJQE-UHFFFAOYSA-N acetic acid;2-methylprop-2-enoic acid Chemical compound CC(O)=O.CC(=C)C(O)=O CDMXXXZRZWQJQE-UHFFFAOYSA-N 0.000 description 1
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- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000002905 alkanoylamido group Chemical group 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
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
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- 229940045984 antineoplastic methylhydrazine Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
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- 125000003435 aroyl group Chemical group 0.000 description 1
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- ORFJCQXUFRFQBX-UHFFFAOYSA-N azetidin-2-one 2,2,2-trifluoroacetic acid Chemical compound O=C1CCN1.OC(=O)C(F)(F)F ORFJCQXUFRFQBX-UHFFFAOYSA-N 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- NQXRQYKIEKLAHI-UHFFFAOYSA-N benzyl n-(2-oxoazetidin-3-yl)carbamate Chemical class C=1C=CC=CC=1COC(=O)NC1CNC1=O NQXRQYKIEKLAHI-UHFFFAOYSA-N 0.000 description 1
- 150000005524 benzylchlorides Chemical class 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
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- 239000012267 brine Substances 0.000 description 1
- HBBRVEMMVUOSTL-UHFFFAOYSA-N butyl n-aminocarbamate Chemical compound CCCCOC(=O)NN HBBRVEMMVUOSTL-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- UCKZMPLVLCKKMO-LHLIQPBNSA-N cephamycin Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](C)[C@]21OC UCKZMPLVLCKKMO-LHLIQPBNSA-N 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
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
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- 230000005494 condensation Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
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- 238000000151 deposition Methods 0.000 description 1
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- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 description 1
- DAKOBUIKDCTJEB-UHFFFAOYSA-L disodium;propanoate Chemical compound [Na+].[Na+].CCC([O-])=O.CCC([O-])=O DAKOBUIKDCTJEB-UHFFFAOYSA-L 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
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- 229940079593 drug Drugs 0.000 description 1
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- FTHUKEBATJXQFL-UHFFFAOYSA-N formic acid;hydrochloride Chemical compound Cl.OC=O FTHUKEBATJXQFL-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 150000002332 glycine derivatives Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 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
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 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
- 229940059936 lithium bromide Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000012452 mother liquor Substances 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
- VKYTZTJFZKKPBL-UHFFFAOYSA-N n-[3-(hydrazinecarbonyl)-2-oxoimidazolidin-1-yl]-4-oxo-5-phenylmethoxy-1h-pyridine-2-carboxamide Chemical class O=C1N(C(=O)NN)CCN1NC(=O)C1=CC(=O)C(OCC=2C=CC=CC=2)=CN1 VKYTZTJFZKKPBL-UHFFFAOYSA-N 0.000 description 1
- JCCYOHZVYALPAS-UHFFFAOYSA-N n-[3-(hydrazinecarbonyl)-2-oxoimidazolidin-1-yl]-5-hydroxy-4-oxo-1h-pyridine-2-carboxamide Chemical class O=C1N(C(=O)NN)CCN1NC(=O)C1=CC(=O)C(O)=CN1 JCCYOHZVYALPAS-UHFFFAOYSA-N 0.000 description 1
- UYMIYCDMRUOMMP-UHFFFAOYSA-N n-aminocarbamoyl chloride Chemical compound NNC(Cl)=O UYMIYCDMRUOMMP-UHFFFAOYSA-N 0.000 description 1
- QGNBDSPDXGLEJP-UHFFFAOYSA-N n-fluoroacetamide Chemical class CC(=O)NF QGNBDSPDXGLEJP-UHFFFAOYSA-N 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
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- 229940049954 penicillin Drugs 0.000 description 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- DXDCKYIDRFGAFT-UHFFFAOYSA-N phenyl dihydrogen phosphate;hydrochloride Chemical compound Cl.OP(O)(=O)OC1=CC=CC=C1 DXDCKYIDRFGAFT-UHFFFAOYSA-N 0.000 description 1
- JTHRRMFZHSDGNJ-UHFFFAOYSA-N piperazine-2,3-dione Chemical compound O=C1NCCNC1=O JTHRRMFZHSDGNJ-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
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- 238000000247 postprecipitation Methods 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 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
- 238000003825 pressing Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 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
- 125000004076 pyridyl group Chemical group 0.000 description 1
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229960001866 silicon dioxide Drugs 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
- 235000014347 soups Nutrition 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- OFNIMGKBLSKHNI-UHFFFAOYSA-N sulfo formate Chemical compound OS(=O)(=O)OC=O OFNIMGKBLSKHNI-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine group Chemical class C(CCC)N(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
- 125000004953 trihalomethyl group Chemical group 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 class C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78047985A | 1985-09-26 | 1985-09-26 | |
| US780.479 | 1985-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN86106980A true CN86106980A (zh) | 1987-04-08 |
Family
ID=25119699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN198686106980A Pending CN86106980A (zh) | 1985-09-26 | 1986-09-26 | 2-氧代-1-{[(取代的磺酰基)-氨基]羰基}氮杂环丁烷类 |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS6284082A (enExample) |
| KR (1) | KR900001013B1 (enExample) |
| CN (1) | CN86106980A (enExample) |
| AT (1) | ATA257986A (enExample) |
| AU (1) | AU600912B2 (enExample) |
| BE (1) | BE905502A (enExample) |
| CA (1) | CA1308719C (enExample) |
| CH (1) | CH670828A5 (enExample) |
| DD (1) | DD250121A5 (enExample) |
| DE (1) | DE3632876A1 (enExample) |
| DK (1) | DK460386A (enExample) |
| EG (1) | EG18314A (enExample) |
| ES (1) | ES2001995A6 (enExample) |
| FI (1) | FI863890A7 (enExample) |
| FR (1) | FR2587700B1 (enExample) |
| GB (1) | GB2181130B (enExample) |
| GR (1) | GR862449B (enExample) |
| HU (1) | HU198044B (enExample) |
| IE (1) | IE59686B1 (enExample) |
| IL (1) | IL80160A (enExample) |
| IT (1) | IT1214533B (enExample) |
| LU (1) | LU86611A1 (enExample) |
| NL (1) | NL8602446A (enExample) |
| NO (1) | NO863837L (enExample) |
| NZ (1) | NZ217704A (enExample) |
| PH (1) | PH23315A (enExample) |
| PL (1) | PL151546B1 (enExample) |
| PT (1) | PT83440B (enExample) |
| SE (1) | SE8604089L (enExample) |
| YU (1) | YU46177B (enExample) |
| ZA (1) | ZA867373B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106986820A (zh) * | 2017-02-24 | 2017-07-28 | 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 |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0246786A1 (en) * | 1986-05-23 | 1987-11-25 | The Upjohn Company | N-1 subsituted sulfonylaminocarbonyl, C-4 substituted monobactams |
| US5006650A (en) * | 1987-02-11 | 1991-04-09 | The Upjohn Company | Novel N-1 substituted beta-lactams as antibiotics |
| JPH02502378A (ja) * | 1987-02-11 | 1990-08-02 | ジ・アップジョン・カンパニー | 抗生物質としての新規なＮ‐１置換β‐ラクタム |
| JPH02502455A (ja) * | 1987-02-27 | 1990-08-09 | ジ・アップジョン・カンパニー | ピリドンカルボン酸または酸誘導体を含有する抗生物質β‐ラクタム |
| 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 |
| US5015737A (en) * | 1987-07-22 | 1991-05-14 | The Upjohn Company | Therapeutically useful beta-lactams |
| KR890701588A (ko) * | 1987-07-22 | 1989-12-21 | 로버어트 에이 아미테이지 | 치료학적으로 유용한 β-락탐 |
| 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 |
| DE69325083T2 (de) * | 1992-12-23 | 1999-10-28 | Novartis Ag, Basel | 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 |
| EP2308562B1 (en) * | 2003-12-25 | 2015-02-25 | 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 |
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 |
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1986
- 1986-09-25 EG EG603/86A patent/EG18314A/xx active
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- 1986-09-26 HU HU864124A patent/HU198044B/hu not_active IP Right Cessation
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- 1986-09-26 PH PH34303A patent/PH23315A/en unknown
- 1986-09-26 AT AT0257986A patent/ATA257986A/de not_active Application Discontinuation
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- 1986-09-26 FR FR8613466A patent/FR2587700B1/fr not_active Expired
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- 1986-09-26 CH CH3860/86A patent/CH670828A5/fr not_active IP Right Cessation
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- 1986-09-26 CN CN198686106980A patent/CN86106980A/zh active Pending
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106986820A (zh) * | 2017-02-24 | 2017-07-28 | 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 |
| 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 |
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