PL146182B1 - Process for preparing novel beta-lactamic derivatives of antibacterial activity - Google Patents
Process for preparing novel beta-lactamic derivatives of antibacterial activity Download PDFInfo
- Publication number
- PL146182B1 PL146182B1 PL1982248815A PL24881582A PL146182B1 PL 146182 B1 PL146182 B1 PL 146182B1 PL 1982248815 A PL1982248815 A PL 1982248815A PL 24881582 A PL24881582 A PL 24881582A PL 146182 B1 PL146182 B1 PL 146182B1
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- Poland
- Prior art keywords
- acid
- group
- formula
- amino
- ethyl
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- 230000000844 anti-bacterial effect Effects 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 aminothiazolyl group Chemical group 0.000 claims description 170
- 239000002253 acid Substances 0.000 claims description 134
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 119
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 72
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 56
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 54
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 34
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 33
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 25
- 159000000000 sodium salts Chemical class 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 16
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical class C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 15
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 9
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- 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 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 4
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical class ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 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 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- JBDKINLIWFKAQO-UHFFFAOYSA-N pyridin-1-ium-1-yl acetate Chemical group CC(=O)O[N+]1=CC=CC=C1 JBDKINLIWFKAQO-UHFFFAOYSA-N 0.000 claims description 3
- RLRCIWRVWQXKBF-UHFFFAOYSA-M sodium 2-ethoxycarbonylpentanoate Chemical compound [Na+].CCCC(C([O-])=O)C(=O)OCC RLRCIWRVWQXKBF-UHFFFAOYSA-M 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 150000003952 β-lactams Chemical class 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 212
- 239000000243 solution Substances 0.000 description 120
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 41
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 38
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 239000012267 brine Substances 0.000 description 30
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 229960000583 acetic acid Drugs 0.000 description 19
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 239000000284 extract Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 244000038458 Nepenthes mirabilis Species 0.000 description 15
- 239000012043 crude product Substances 0.000 description 15
- 238000001035 drying Methods 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000001665 trituration Methods 0.000 description 6
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 5
- 101150041968 CDC13 gene Proteins 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
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- 239000007788 liquid Substances 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 4
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
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- 241000699670 Mus sp. Species 0.000 description 3
- 229930182555 Penicillin Natural products 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
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- 239000006188 syrup Substances 0.000 description 3
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- MHSGOABISYIYKP-UHFFFAOYSA-N (4-nitrophenyl)methyl carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(COC(Cl)=O)C=C1 MHSGOABISYIYKP-UHFFFAOYSA-N 0.000 description 2
- XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
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- CFFZDZCDUFSOFZ-UHFFFAOYSA-N 3,4-Dihydroxy-phenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C(O)=C1 CFFZDZCDUFSOFZ-UHFFFAOYSA-N 0.000 description 2
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- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 2
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
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- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
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- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D463/10—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D463/14—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hetero atoms directly attached in position 7
- C07D463/16—Nitrogen atoms
- C07D463/18—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof
- C07D463/20—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D463/22—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen further substituted by nitrogen 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
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8123034 | 1981-07-25 | ||
| GB8123033 | 1981-07-25 | ||
| GB8136823 | 1981-12-07 | ||
| GB8136824 | 1981-12-07 | ||
| GB8207966 | 1982-03-18 | ||
| GB8209954 | 1982-04-03 | ||
| GB8209953 | 1982-04-03 | ||
| GB8215007 | 1982-05-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL248815A1 PL248815A1 (en) | 1985-04-09 |
| PL146182B1 true PL146182B1 (en) | 1989-01-31 |
Family
ID=27571208
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1982248815A PL146182B1 (en) | 1981-07-25 | 1982-07-23 | Process for preparing novel beta-lactamic derivatives of antibacterial activity |
| PL1982237640A PL145252B1 (en) | 1981-07-25 | 1982-07-23 | Method of obtaining novel beta-lactame derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1982237640A PL145252B1 (en) | 1981-07-25 | 1982-07-23 | Method of obtaining novel beta-lactame derivatives |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US4539149A (enExample) |
| EP (1) | EP0071395B1 (enExample) |
| KR (1) | KR900000934B1 (enExample) |
| AU (1) | AU568062B2 (enExample) |
| CA (1) | CA1216576A (enExample) |
| DE (1) | DE3278878D1 (enExample) |
| FI (1) | FI78702C (enExample) |
| GB (1) | GB2107307B (enExample) |
| GR (1) | GR76544B (enExample) |
| HK (1) | HK58088A (enExample) |
| KE (1) | KE3810A (enExample) |
| MY (1) | MY8700744A (enExample) |
| NO (1) | NO162192C (enExample) |
| NZ (1) | NZ201369A (enExample) |
| PH (4) | PH20467A (enExample) |
| PL (2) | PL146182B1 (enExample) |
| PT (1) | PT75304B (enExample) |
| YU (2) | YU43083B (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8301694D0 (en) * | 1983-01-21 | 1983-02-23 | Beecham Group Plc | Beta-lactam antibacterial agents |
| EP0114752B1 (en) * | 1983-01-21 | 1988-04-06 | Beecham Group Plc | Beta-lactam antibacterial agents |
| EP0114751B1 (en) * | 1983-01-21 | 1987-12-09 | Beecham Group Plc | Beta-lactam antibacterial agents |
| FI81354C (fi) * | 1983-01-21 | 1990-10-10 | Beecham Group Plc | Foerfarande foer framstaellning av formamidosubstituerad -laktam-antibiotika. |
| AU2361084A (en) * | 1983-01-24 | 1984-07-26 | Beecham Group Plc | Beta-lactam antibacterial agents |
| DE3479731D1 (en) * | 1983-07-07 | 1989-10-19 | Beecham Group Plc | Substituted phenylglycine derivatives of beta-lactam antibiotics |
| JPS6066987A (ja) * | 1983-09-20 | 1985-04-17 | Takeda Chem Ind Ltd | 抗生物質ｔａν−５４７，その製造法および微生物 |
| DE3481769D1 (de) * | 1984-01-23 | 1990-05-03 | Takeda Chemical Industries Ltd | Cephemderivate und ihre herstellung. |
| EP0160745A3 (en) * | 1984-05-07 | 1986-11-05 | Takeda Chemical Industries, Ltd. | Cephem compounds and their production |
| EP0167011A3 (en) * | 1984-06-12 | 1986-03-19 | Beecham Group Plc | Beta-lactam compounds, intermediates thereof, their use in preparing beta-lactams having a diketopiperazine group |
| EP0168177A3 (en) * | 1984-06-28 | 1987-04-01 | Pfizer Limited | Cephalosporin antibiotics |
| EP0219926A3 (en) * | 1985-06-25 | 1988-08-31 | Beecham Group Plc | Cephalosporins, processes for their preparation and pharmaceutical compositions containing them |
| JPS6230789A (ja) * | 1985-08-01 | 1987-02-09 | Yamanouchi Pharmaceut Co Ltd | ７−ホルミルアミノセフアロスポリン化合物およびその製造法 |
| EP0211656A3 (en) * | 1985-08-10 | 1988-03-09 | Beecham Group Plc | Cephalosporin derivatives, process for their preparation and pharmaceutical compositions containing them |
| GB8531202D0 (en) * | 1985-12-18 | 1986-01-29 | Pfizer Ltd | Cephalosporin antibiotics |
| US4666835A (en) * | 1986-04-29 | 1987-05-19 | Baldwin Jack E | 2-vinylpenams and process |
| GB8709666D0 (en) * | 1987-04-23 | 1987-05-28 | Beecham Group Plc | Compounds |
| GB8719875D0 (en) * | 1987-08-22 | 1987-09-30 | Beecham Group Plc | Compounds |
| GB8722477D0 (en) * | 1987-09-24 | 1987-10-28 | Beecham Group Plc | Compounds |
| DE3733626A1 (de) * | 1987-10-05 | 1989-04-13 | Bayer Ag | Heteroanellierte phenylglycin-(beta)-lactam-antibiotika, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| ATE118215T1 (de) * | 1989-09-04 | 1995-02-15 | Beecham Group Plc | Cephalosporinderivate, verfahren zu ihrer herstellung, pharmazeutische präparate und zwischenverbindungen. |
| US7601864B1 (en) * | 2008-05-08 | 2009-10-13 | Ufc Corporation | Method for synthesizing 4,4-dihalogen-2-(dialkylamino)methylene-3-oxy-alkylbutyrate and derivatives thereof |
| WO2013057196A1 (en) | 2011-10-20 | 2013-04-25 | Dsm Sinochem Pharmaceuticals Netherlands B.V. | Process for the preparation of cefamandole nafate |
| WO2013057197A1 (en) | 2011-10-20 | 2013-04-25 | Dsm Sinochem Pharmaceuticals Netherlands B.V. | Process for the formylation of cefamandole |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR205683A1 (es) * | 1970-06-16 | 1976-05-31 | Merck & Co Inc | Procedimiento para la preparacion del ester de bencilo del acido 6-metoxi-6-acilamido penicilanico |
| GB1442302A (en) * | 1972-07-21 | 1976-07-14 | Glaxo Lab Ltd | Penicillin and cephalosporin derivatives |
| US3868365A (en) * | 1972-12-06 | 1975-02-25 | Squibb & Sons Inc | Method for preparing 6-substituted penicillins by replacement of oxygen containing groups |
| US4062842A (en) * | 1973-09-06 | 1977-12-13 | E. R. Squibb & Sons, Inc. | Method for preparing 7-substituted cephalosporins and 6-substituted penicillins by replacement of sulfur-containing groups |
| US3937655A (en) * | 1974-04-16 | 1976-02-10 | Eli Lilly And Company | Method for preparing stable β-lactam-type-antibiotic susceptibility test discs |
| US3962214A (en) * | 1974-07-11 | 1976-06-08 | Eli Lilly And Company | Process for preparing amino substituted β-lactam antibiotics |
| US4281117A (en) * | 1980-09-04 | 1981-07-28 | Eli Lilly And Company | Process for 3-chloro cephalosporin nucleus |
-
1982
- 1982-07-21 GB GB08221059A patent/GB2107307B/en not_active Expired
- 1982-07-21 DE DE8282303821T patent/DE3278878D1/de not_active Expired
- 1982-07-21 EP EP82303821A patent/EP0071395B1/en not_active Expired
- 1982-07-23 PH PH27619A patent/PH20467A/en unknown
- 1982-07-23 PL PL1982248815A patent/PL146182B1/pl unknown
- 1982-07-23 GR GR68844A patent/GR76544B/el unknown
- 1982-07-23 US US06/401,266 patent/US4539149A/en not_active Expired - Fee Related
- 1982-07-23 PL PL1982237640A patent/PL145252B1/pl unknown
- 1982-07-23 NO NO822538A patent/NO162192C/no unknown
- 1982-07-23 PT PT75304A patent/PT75304B/pt not_active IP Right Cessation
- 1982-07-23 YU YU1623/82A patent/YU43083B/xx unknown
- 1982-07-23 CA CA000407903A patent/CA1216576A/en not_active Expired
- 1982-07-23 FI FI822606A patent/FI78702C/fi not_active IP Right Cessation
- 1982-07-23 AU AU86351/82A patent/AU568062B2/en not_active Ceased
- 1982-07-23 NZ NZ201369A patent/NZ201369A/en unknown
- 1982-07-23 KR KR8203308A patent/KR900000934B1/ko not_active Expired
-
1984
- 1984-10-18 YU YU178484A patent/YU45671B/sh unknown
-
1985
- 1985-01-24 US US06/694,622 patent/US4877783A/en not_active Expired - Fee Related
- 1985-01-24 US US06/694,592 patent/US4609652A/en not_active Expired - Fee Related
-
1986
- 1986-05-12 PH PH33761A patent/PH21703A/en unknown
- 1986-05-12 PH PH33762A patent/PH21701A/en unknown
- 1986-05-12 PH PH33760A patent/PH21702A/en unknown
-
1987
- 1987-12-30 MY MY744/87A patent/MY8700744A/xx unknown
-
1988
- 1988-04-25 KE KE3810A patent/KE3810A/xx unknown
- 1988-07-28 HK HK580/88A patent/HK58088A/xx unknown
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