NO311975B1 - Nye syntetiske katecholderivater, samt legemiddel inneholdende en slik forbindelse - Google Patents
Nye syntetiske katecholderivater, samt legemiddel inneholdende en slik forbindelse Download PDFInfo
- Publication number
- NO311975B1 NO311975B1 NO19985858A NO985858A NO311975B1 NO 311975 B1 NO311975 B1 NO 311975B1 NO 19985858 A NO19985858 A NO 19985858A NO 985858 A NO985858 A NO 985858A NO 311975 B1 NO311975 B1 NO 311975B1
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- formula
- ampicillin
- branched
- residue
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 55
- 239000003814 drug Substances 0.000 title claims description 9
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 title claims description 6
- 229940079593 drug Drugs 0.000 title claims description 4
- 229960000723 ampicillin Drugs 0.000 claims description 36
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 26
- 229960004841 cefadroxil Drugs 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 14
- NBFNMSULHIODTC-CYJZLJNKSA-N cefadroxil monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=C(O)C=C1 NBFNMSULHIODTC-CYJZLJNKSA-N 0.000 claims description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- OTSSVGGWRCGGFW-NRFANRHFSA-N (2s)-2,6-bis[(2,3-diacetyloxybenzoyl)amino]hexanoic acid Chemical compound CC(=O)OC1=CC=CC(C(=O)NCCCC[C@H](NC(=O)C=2C(=C(OC(C)=O)C=CC=2)OC(C)=O)C(O)=O)=C1OC(C)=O OTSSVGGWRCGGFW-NRFANRHFSA-N 0.000 claims description 7
- QTIOPWJOBZYADA-ZETCQYMHSA-N (2s)-2-[(2,3-diacetyloxybenzoyl)amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)C1=CC=CC(OC(C)=O)=C1OC(C)=O QTIOPWJOBZYADA-ZETCQYMHSA-N 0.000 claims description 7
- KNWCDYSKJSREAQ-UHFFFAOYSA-N 1,3-oxazolidine-2-carboxylic acid Chemical group OC(=O)C1NCCO1 KNWCDYSKJSREAQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 230000010438 iron metabolism Effects 0.000 claims description 6
- XODZHOVMNGAQCZ-UHFFFAOYSA-N 2-[(2,3-diacetyloxybenzoyl)amino]benzoic acid Chemical compound CC(=O)OC1=CC=CC(C(=O)NC=2C(=CC=CC=2)C(O)=O)=C1OC(C)=O XODZHOVMNGAQCZ-UHFFFAOYSA-N 0.000 claims description 5
- 208000035143 Bacterial infection Diseases 0.000 claims description 5
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical group NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 5
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- UJQDRPLHEPIIAC-FDYZEBBJSA-N 2-[(z)-[(3z)-3-(diaminomethylidenehydrazinylidene)cyclopenta[b]naphthalen-1-ylidene]amino]guanidine Chemical group C1=CC=C2C=C3C(=N/N=C(N)N)\C\C(=N\N=C(N)N)C3=CC2=C1 UJQDRPLHEPIIAC-FDYZEBBJSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical group C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- UVOKEWIIBKIDIY-UHFFFAOYSA-N 2-phenyldiazenylbenzoic acid Chemical group OC(=O)C1=CC=CC=C1N=NC1=CC=CC=C1 UVOKEWIIBKIDIY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000000539 amino acid group Chemical group 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
- 239000000126 substance Substances 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- 239000000589 Siderophore Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- -1 benzhydrazones Chemical class 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 229910052742 iron Inorganic materials 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 230000001580 bacterial effect Effects 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- 230000035515 penetration Effects 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000003242 anti bacterial agent Substances 0.000 description 11
- 230000003115 biocidal effect Effects 0.000 description 11
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 11
- 241000588724 Escherichia coli Species 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 239000013543 active substance Substances 0.000 description 9
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical group NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 8
- 229940088710 antibiotic agent Drugs 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 229940024606 amino acid Drugs 0.000 description 7
- 235000001014 amino acid Nutrition 0.000 description 7
- 229960003623 azlocillin Drugs 0.000 description 7
- JTWOMNBEOCYFNV-NFFDBFGFSA-N azlocillin Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC=CC=1)C(=O)N1CCNC1=O JTWOMNBEOCYFNV-NFFDBFGFSA-N 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 230000037361 pathway Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- JWIRVWSAMLMXIV-UHFFFAOYSA-N (2-acetyloxy-3-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(C(Cl)=O)=C1OC(C)=O JWIRVWSAMLMXIV-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 108010016626 Dipeptides Proteins 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- TTZFFDUBICLVMI-UHFFFAOYSA-N 3-[[3,4-bis(methoxycarbonyloxy)phenyl]methylideneamino]benzoic acid Chemical compound C1=C(OC(=O)OC)C(OC(=O)OC)=CC=C1C=NC1=CC=CC(C(O)=O)=C1 TTZFFDUBICLVMI-UHFFFAOYSA-N 0.000 description 5
- QCWURZLKTSDILY-UHFFFAOYSA-N 4-[(3,4-diacetyloxyphenyl)methylideneamino]benzoic acid Chemical compound C1=C(OC(C)=O)C(OC(=O)C)=CC=C1C=NC1=CC=C(C(O)=O)C=C1 QCWURZLKTSDILY-UHFFFAOYSA-N 0.000 description 5
- JSGOTGVPCCMIOB-UHFFFAOYSA-N C=1C=CC=CC=1C(C(=O)O)=NNC(=O)C1=CC=C(O)C(O)=C1 Chemical compound C=1C=CC=CC=1C(C(=O)O)=NNC(=O)C1=CC=C(O)C(O)=C1 JSGOTGVPCCMIOB-UHFFFAOYSA-N 0.000 description 5
- 241000589516 Pseudomonas Species 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229960004050 aminobenzoic acid Drugs 0.000 description 5
- 229960003311 ampicillin trihydrate Drugs 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 239000002738 chelating agent Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000002953 preparative HPLC Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- RLFWLXIRWKNYBP-YFKPBYRVSA-N (2S)-2-[(2,3-dihydroxybenzoyl)amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)C1=CC=CC(O)=C1O RLFWLXIRWKNYBP-YFKPBYRVSA-N 0.000 description 4
- SGVOQUJRSFVMGF-GGYWPGCISA-N (2S)-3-[2,6-bis[(2,3-dihydroxybenzoyl)amino]hexanoylamino]-2-[(2,3-dihydroxybenzoyl)amino]propanoic acid Chemical compound OC1=C(C(=O)NC(C(=O)NC[C@@H](C(=O)O)NC(C2=C(C(=CC=C2)O)O)=O)CCCCNC(C2=C(C(=CC=C2)O)O)=O)C=CC=C1O SGVOQUJRSFVMGF-GGYWPGCISA-N 0.000 description 4
- HVHYEALZJDGYGS-NSHDSACASA-N (2s)-2,4-bis[(2,3-dihydroxybenzoyl)amino]butanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C(=C(O)C=CC=1)O)CNC(=O)C1=CC=CC(O)=C1O HVHYEALZJDGYGS-NSHDSACASA-N 0.000 description 4
- FAECQSURBKNDIY-LBPRGKRZSA-N (2s)-2,5-bis[(2,3-dihydroxybenzoyl)amino]pentanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C(=C(O)C=CC=1)O)CCNC(=O)C1=CC=CC(O)=C1O FAECQSURBKNDIY-LBPRGKRZSA-N 0.000 description 4
- IXWOUPGDGMCKGT-UHFFFAOYSA-N 2,3-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1O IXWOUPGDGMCKGT-UHFFFAOYSA-N 0.000 description 4
- VKKFLAWWJFGHJC-UHFFFAOYSA-N 3,5-bis[[3,4-bis(methoxycarbonyloxy)phenyl]methylideneamino]benzoic acid Chemical compound C1=C(OC(=O)OC)C(OC(=O)OC)=CC=C1C=NC1=CC(N=CC=2C=C(OC(=O)OC)C(OC(=O)OC)=CC=2)=CC(C(O)=O)=C1 VKKFLAWWJFGHJC-UHFFFAOYSA-N 0.000 description 4
- LAXUBKMFSPIYQM-UHFFFAOYSA-N 3-[(2,3-dihydroxyphenyl)methylideneamino]-4-hydroxybenzoic acid Chemical compound OC1=C(C=NC=2C=C(C(=O)O)C=CC2O)C=CC=C1O LAXUBKMFSPIYQM-UHFFFAOYSA-N 0.000 description 4
- PKDYCCLKDRHWAU-UHFFFAOYSA-N 3-[(3,4-diacetyloxyphenyl)iminomethyl]-4,5-dihydroxybenzoic acid Chemical compound C1=C(OC(C)=O)C(OC(=O)C)=CC=C1N=CC1=CC(C(O)=O)=CC(O)=C1O PKDYCCLKDRHWAU-UHFFFAOYSA-N 0.000 description 4
- KYMHAFMJRLOPKB-UHFFFAOYSA-N 3-[[3,4-bis(methoxycarbonyloxy)phenyl]methylideneamino]-4-hydroxybenzoic acid Chemical compound C1=C(OC(=O)OC)C(OC(=O)OC)=CC=C1C=NC1=CC(C(O)=O)=CC=C1O KYMHAFMJRLOPKB-UHFFFAOYSA-N 0.000 description 4
- JHCKACPIHNIJCV-UHFFFAOYSA-N 4-[(2,3-diacetyloxybenzoyl)amino]benzoic acid Chemical compound CC(=O)OC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C(O)=O)=C1OC(C)=O JHCKACPIHNIJCV-UHFFFAOYSA-N 0.000 description 4
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 4
- RJXLOTQYOAFVNC-UHFFFAOYSA-N C=1C=C(C(O)=O)C=CC=1C(=NN)C(=O)C1=CC=C(O)C(O)=C1 Chemical compound C=1C=C(C(O)=O)C=CC=1C(=NN)C(=O)C1=CC=C(O)C(O)=C1 RJXLOTQYOAFVNC-UHFFFAOYSA-N 0.000 description 4
- SERBHKJMVBATSJ-UHFFFAOYSA-N Enterobactin Natural products OC1=CC=CC(C(=O)NC2C(OCC(C(=O)OCC(C(=O)OC2)NC(=O)C=2C(=C(O)C=CC=2)O)NC(=O)C=2C(=C(O)C=CC=2)O)=O)=C1O SERBHKJMVBATSJ-UHFFFAOYSA-N 0.000 description 4
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- 108010013381 Porins Proteins 0.000 description 4
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 4
- KLOHDWPABZXLGI-YWUHCJSESA-M ampicillin sodium Chemical compound [Na+].C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C([O-])=O)(C)C)=CC=CC=C1 KLOHDWPABZXLGI-YWUHCJSESA-M 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
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- 230000007903 penetration ability Effects 0.000 description 4
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- NYBZAGXTZXPYND-GBIKHYSHSA-N pyochelin I Chemical compound S1C[C@@H](C(O)=O)N(C)[C@H]1[C@@H]1N=C(C=2C(=CC=CC=2)O)SC1 NYBZAGXTZXPYND-GBIKHYSHSA-N 0.000 description 4
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- 150000003512 tertiary amines Chemical class 0.000 description 4
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 3
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- ABYBTMRWBKUAQK-NSHDSACASA-N (4s)-3-(2,3-diacetyloxybenzoyl)-1,3-oxazolidine-4-carboxylic acid Chemical compound CC(=O)OC1=CC=CC(C(=O)N2[C@@H](COC2)C(O)=O)=C1OC(C)=O ABYBTMRWBKUAQK-NSHDSACASA-N 0.000 description 3
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- 241000894006 Bacteria Species 0.000 description 3
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- 241000588747 Klebsiella pneumoniae Species 0.000 description 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 3
- 108010052285 Membrane Proteins Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- HKSGNVBOEXPQHJ-LTCKWSDVSA-N benzyl (2s)-2,6-diaminohexanoate;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1.NCCCC[C@H](N)C(=O)OCC1=CC=CC=C1 HKSGNVBOEXPQHJ-LTCKWSDVSA-N 0.000 description 1
- RLMHWGDKMJIEHH-QRPNPIFTSA-N benzyl (2s)-2-aminopropanoate;hydrochloride Chemical compound Cl.C[C@H](N)C(=O)OCC1=CC=CC=C1 RLMHWGDKMJIEHH-QRPNPIFTSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 description 1
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 1
- 229940106164 cephalexin Drugs 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940088530 claforan Drugs 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 229960000958 deferoxamine Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229940099217 desferal Drugs 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 description 1
- 229960002182 imipenem Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- 150000002668 lysine derivatives Chemical class 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 description 1
- 229960002260 meropenem Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 102220090095 rs1042713 Human genes 0.000 description 1
- 150000003354 serine derivatives Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 229940098232 yersinia enterocolitica Drugs 0.000 description 1
- JHYVWAMMAMCUIR-VQNLDRKJSA-N yersiniabactin Chemical compound C([C@@H](N=1)C2SC[C@H](N2)[C@@H](O)C(C)(C)C=2SC[C@@](C)(N=2)C(O)=O)SC=1C1=CC=CC=C1O JHYVWAMMAMCUIR-VQNLDRKJSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/10—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C251/16—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/547—Chelates, e.g. Gd-DOTA or Zinc-amino acid chelates; Chelate-forming compounds, e.g. DOTA or ethylenediamine being covalently linked or complexed to the pharmacologically- or therapeutically-active agent
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/64—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/74—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/78—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C251/80—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Communicable Diseases (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19625524A DE19625524C2 (de) | 1996-06-26 | 1996-06-26 | Neue synthetische Catechol-Antibiotika-Konjugate und diese enthaltende Arzneimittel |
PCT/EP1997/002453 WO1997049670A1 (de) | 1996-06-26 | 1997-05-14 | Neue synthetische catecholderivate, verfahren zu ihrer herstellung und ihre verwendung |
Publications (3)
Publication Number | Publication Date |
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NO985858L NO985858L (no) | 1998-12-14 |
NO985858D0 NO985858D0 (no) | 1998-12-14 |
NO311975B1 true NO311975B1 (no) | 2002-02-25 |
Family
ID=7798042
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19985858A NO311975B1 (no) | 1996-06-26 | 1998-12-14 | Nye syntetiske katecholderivater, samt legemiddel inneholdende en slik forbindelse |
Country Status (30)
Country | Link |
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US (1) | US6380181B1 (es) |
EP (1) | EP0907633B1 (es) |
JP (1) | JP2000514042A (es) |
KR (1) | KR20000022120A (es) |
CN (1) | CN1106380C (es) |
AR (1) | AR008391A1 (es) |
AT (1) | ATE204563T1 (es) |
AU (1) | AU728669B2 (es) |
BR (1) | BR9709964A (es) |
CA (1) | CA2252809A1 (es) |
CO (1) | CO4900028A1 (es) |
CZ (1) | CZ9804297A3 (es) |
DE (2) | DE19654920A1 (es) |
DK (1) | DK0907633T3 (es) |
ES (1) | ES2163161T3 (es) |
GR (1) | GR3036667T3 (es) |
HK (1) | HK1018613A1 (es) |
HU (1) | HUP0001746A3 (es) |
IL (1) | IL126703A0 (es) |
NO (1) | NO311975B1 (es) |
NZ (1) | NZ332519A (es) |
PE (1) | PE70098A1 (es) |
PL (1) | PL330899A1 (es) |
PT (1) | PT907633E (es) |
RU (1) | RU2180898C2 (es) |
SK (1) | SK283560B6 (es) |
UA (1) | UA54437C2 (es) |
UY (1) | UY24596A1 (es) |
WO (1) | WO1997049670A1 (es) |
ZA (1) | ZA975638B (es) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19708846A1 (de) * | 1997-03-05 | 1998-09-17 | Gruenenthal Gmbh | Neue Benzoxazindionderivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
US6613942B1 (en) | 1997-07-01 | 2003-09-02 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
WO1999042435A2 (de) * | 1998-02-21 | 1999-08-26 | Analyticon Ag Biotechnologie Pharmazie | Myxocheline |
US20040186087A1 (en) * | 2003-03-20 | 2004-09-23 | Ceramoptec Industries, Inc. | Siderophore conjugates of photoactive dyes for photodynamic therapy |
DE102004030987A1 (de) * | 2004-06-26 | 2006-01-12 | Merck Patent Gmbh | Ortho-substituierte (3-Hydroxyphenyl)-essigsäure-benzyliden-hydrazide |
US20100240713A1 (en) * | 2007-06-05 | 2010-09-23 | Xenon Pharmaceuticals Inc. | Aromatic and heteroaromatic compounds useful in treating iron disorders |
US20090233972A1 (en) * | 2008-03-12 | 2009-09-17 | Yat Sun Or | Substituted heterocycles as anti-infectives |
EP3265130B1 (en) * | 2014-08-19 | 2024-05-22 | Hsiri Therapeutics, LLC | Antibacterial sideromycins |
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DE3215085A1 (de) | 1982-04-22 | 1983-10-27 | Bayer Ag, 5090 Leverkusen | Ss-lactam-antibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
JPS59193822A (ja) * | 1983-04-15 | 1984-11-02 | Kureha Chem Ind Co Ltd | 腎炎治療剤 |
US4610824A (en) | 1984-10-09 | 1986-09-09 | E. R. Squibb & Sons, Inc. | Hydrazide derivatives of monocyclic beta-lactam antibiotics |
AU586215B2 (en) * | 1985-01-21 | 1989-07-06 | Nippon Pharmaceutical Development Institute Company Limited | Novel ```-lactam antibiotics |
ZA877987B (en) * | 1986-11-12 | 1988-08-31 | Ici Pharma | Antibiotic compounds |
GB8811055D0 (en) * | 1988-05-10 | 1988-06-15 | Ici Plc | Antibiotic compounds |
AU644008B2 (en) * | 1990-08-10 | 1993-12-02 | Sumitomo Pharmaceuticals Company, Limited | Beta-lactam compounds, and their production and use |
EP0544166A3 (en) | 1991-11-26 | 1993-11-03 | Hoffmann La Roche | Cephalosporinderivatives |
JPWO9318062A1 (en) * | 1992-03-11 | 1994-03-03 | Kyowa Hakko Kogyo Kk | Peptide which inhibits phospholipase c. |
DE4231295A1 (de) | 1992-09-18 | 1994-03-24 | Knoell Hans Forschung Ev | Neue alpha-Aminoacylpenicilline mit substituierten Dicarboxamoyl-Seitenketten, Verfahren zu ihrer Herstellung und ihre Verwendung |
DE4313946A1 (de) | 1993-04-28 | 1994-11-03 | Knoell Hans Forschung Ev | Neue O-Acyl-N-(diacyloxybenzoyl)-amoxicillinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
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1996
- 1996-06-26 DE DE19654920A patent/DE19654920A1/de not_active Withdrawn
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1997
- 1997-05-14 NZ NZ332519A patent/NZ332519A/xx unknown
- 1997-05-14 SK SK1788-98A patent/SK283560B6/sk unknown
- 1997-05-14 DK DK97923887T patent/DK0907633T3/da active
- 1997-05-14 HU HU0001746A patent/HUP0001746A3/hu unknown
- 1997-05-14 AU AU29542/97A patent/AU728669B2/en not_active Ceased
- 1997-05-14 CZ CZ19984297A patent/CZ9804297A3/cs unknown
- 1997-05-14 KR KR1019980710534A patent/KR20000022120A/ko not_active Application Discontinuation
- 1997-05-14 CN CN97195765A patent/CN1106380C/zh not_active Expired - Fee Related
- 1997-05-14 UA UA99010372A patent/UA54437C2/uk unknown
- 1997-05-14 JP JP10502161A patent/JP2000514042A/ja active Pending
- 1997-05-14 IL IL12670397A patent/IL126703A0/xx unknown
- 1997-05-14 WO PCT/EP1997/002453 patent/WO1997049670A1/de not_active Application Discontinuation
- 1997-05-14 EP EP97923887A patent/EP0907633B1/de not_active Expired - Lifetime
- 1997-05-14 AT AT97923887T patent/ATE204563T1/de not_active IP Right Cessation
- 1997-05-14 RU RU99101045/04A patent/RU2180898C2/ru not_active IP Right Cessation
- 1997-05-14 DE DE59704380T patent/DE59704380D1/de not_active Expired - Fee Related
- 1997-05-14 ES ES97923887T patent/ES2163161T3/es not_active Expired - Lifetime
- 1997-05-14 BR BR9709964A patent/BR9709964A/pt not_active IP Right Cessation
- 1997-05-14 CA CA002252809A patent/CA2252809A1/en not_active Abandoned
- 1997-05-14 PT PT97923887T patent/PT907633E/pt unknown
- 1997-05-14 PL PL97330899A patent/PL330899A1/xx unknown
- 1997-05-14 US US09/202,955 patent/US6380181B1/en not_active Expired - Fee Related
- 1997-06-11 AR ARP970102549A patent/AR008391A1/es unknown
- 1997-06-13 PE PE1997000491A patent/PE70098A1/es not_active Application Discontinuation
- 1997-06-24 UY UY24596A patent/UY24596A1/es unknown
- 1997-06-24 CO CO97035121A patent/CO4900028A1/es unknown
- 1997-06-25 ZA ZA9705638A patent/ZA975638B/xx unknown
-
1998
- 1998-12-14 NO NO19985858A patent/NO311975B1/no not_active IP Right Cessation
-
1999
- 1999-08-20 HK HK99103611A patent/HK1018613A1/xx not_active IP Right Cessation
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2001
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