BE856243A - Nouveaux composes de penicilline - Google Patents

Nouveaux composes de penicilline

Info

Publication number: BE856243A
Authority: BE; Belgium
Prior art keywords: emi; compound; penicillin; formula; pharmaceutically acceptable
Prior art date: 1976-06-30

Application number

BE178882A

Other languages

English (en)

French (fr)

Original Assignee

Dainippon Pharmaceutical Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-06-30

Filing date

1977-06-29

Publication date

1977-12-29

1977-06-29 Application filed by Dainippon Pharmaceutical Co filed Critical Dainippon Pharmaceutical Co

1977-12-29 Publication of BE856243A publication Critical patent/BE856243A/fr

Links

150000002960 penicillins Chemical class 0.000 title claims description 61
150000001875 compounds Chemical class 0.000 claims description 101
239000000243 solution Substances 0.000 claims description 65
-1 penicillin compound Chemical class 0.000 claims description 63
150000003839 salts Chemical class 0.000 claims description 59
229930182555 Penicillin Natural products 0.000 claims description 45
229940049954 penicillin Drugs 0.000 claims description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
238000000034 method Methods 0.000 claims description 34
231100000252 nontoxic Toxicity 0.000 claims description 34
230000003000 nontoxic effect Effects 0.000 claims description 34
230000000844 anti-bacterial effect Effects 0.000 claims description 32
238000002347 injection Methods 0.000 claims description 26
239000007924 injection Substances 0.000 claims description 26
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 20
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 15
239000007795 chemical reaction product Substances 0.000 claims description 13
239000002609 medium Substances 0.000 claims description 13
239000007788 liquid Substances 0.000 claims description 12
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
239000003242 anti bacterial agent Substances 0.000 claims description 9
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 8
238000007911 parenteral administration Methods 0.000 claims description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 7
239000008367 deionised water Substances 0.000 claims description 7
229910021641 deionized water Inorganic materials 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
239000011734 sodium Substances 0.000 claims description 7
AZCVBVRUYHKWHU-MBNYWOFBSA-N Penicillin X Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=C(O)C=C1 AZCVBVRUYHKWHU-MBNYWOFBSA-N 0.000 claims description 6
230000000144 pharmacologic effect Effects 0.000 claims description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
229940079593 drug Drugs 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
238000011282 treatment Methods 0.000 claims description 5
239000012736 aqueous medium Substances 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
229930186147 Cephalosporin Natural products 0.000 claims description 3
229940124587 cephalosporin Drugs 0.000 claims description 3
150000001780 cephalosporins Chemical class 0.000 claims description 3
238000007920 subcutaneous administration Methods 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
239000003708 ampul Substances 0.000 claims 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 2
239000002671 adjuvant Substances 0.000 claims 1
239000004615 ingredient Substances 0.000 claims 1
230000003204 osmotic effect Effects 0.000 claims 1
239000003002 pH adjusting agent Substances 0.000 claims 1
239000003381 stabilizer Substances 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
239000000203 mixture Substances 0.000 description 45
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
239000002244 precipitate Substances 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 24
238000001914 filtration Methods 0.000 description 23
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 22
239000007864 aqueous solution Substances 0.000 description 19
239000000706 filtrate Substances 0.000 description 18
241000699670 Mus sp. Species 0.000 description 15
239000005457 ice water Substances 0.000 description 15
239000000126 substance Substances 0.000 description 13
239000000725 suspension Substances 0.000 description 13
241000589517 Pseudomonas aeruginosa Species 0.000 description 12
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 12
241000894006 Bacteria Species 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin 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=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 11
229910052799 carbon Inorganic materials 0.000 description 11
239000000047 product Substances 0.000 description 11
239000013078 crystal Substances 0.000 description 10
210000002700 urine Anatomy 0.000 description 10
QZPMHVOJMAXMND-UHFFFAOYSA-N (1-methylpiperidin-4-yl) 2-cyclohexyl-2-hydroxy-2-phenylacetate Chemical compound C1CN(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCCC1 QZPMHVOJMAXMND-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
230000037396 body weight Effects 0.000 description 9
229940125904 compound 1 Drugs 0.000 description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
239000007858 starting material Substances 0.000 description 9
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 8
125000002252 acyl group Chemical group 0.000 description 7
229960003022 amoxicillin Drugs 0.000 description 7
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 description 7
239000002585 base Substances 0.000 description 7
238000001816 cooling Methods 0.000 description 7
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 7
NHLLQCBSWYJLRI-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine-2-carboxylic acid Chemical group N1=CC=CC2=NC(C(=O)O)=NC=C21 NHLLQCBSWYJLRI-UHFFFAOYSA-N 0.000 description 7
159000000000 sodium salts Chemical class 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
229960000723 ampicillin Drugs 0.000 description 6
238000001727 in vivo Methods 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 6
229940126062 Compound A Drugs 0.000 description 5
241000588724 Escherichia coli Species 0.000 description 5
241000192125 Firmicutes Species 0.000 description 5
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
125000004433 nitrogen atom Chemical group N* 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
230000001580 bacterial effect Effects 0.000 description 4
239000006172 buffering agent Substances 0.000 description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
239000002504 physiological saline solution Substances 0.000 description 4
BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical group C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical group OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
241000191967 Staphylococcus aureus Species 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
230000002489 hematologic effect Effects 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
231100000053 low toxicity Toxicity 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
229960002317 succinimide Drugs 0.000 description 3
235000019786 weight gain Nutrition 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical class O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 2
PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical class CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 description 2
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
229930194542 Keto Natural products 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000589516 Pseudomonas Species 0.000 description 2
230000005856 abnormality Effects 0.000 description 2
230000021736 acetylation Effects 0.000 description 2
238000006640 acetylation reaction Methods 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000010227 cup method (microbiological evaluation) Methods 0.000 description 2
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
230000022244 formylation Effects 0.000 description 2
238000006170 formylation reaction Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000001072 heteroaryl group Chemical group 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
150000004677 hydrates Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
210000003734 kidney Anatomy 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
235000019371 penicillin G benzathine Nutrition 0.000 description 2
229940056360 penicillin g Drugs 0.000 description 2
206010034674 peritonitis Diseases 0.000 description 2
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 2
229960002292 piperacillin Drugs 0.000 description 2
WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 description 2
159000000001 potassium salts Chemical class 0.000 description 2
IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
239000010409 thin film Substances 0.000 description 2
230000036325 urinary excretion Effects 0.000 description 2
NIBFJPXGNVPNHK-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-4-carbaldehyde Chemical group C1=CC(C=O)=C2OC(F)(F)OC2=C1 NIBFJPXGNVPNHK-UHFFFAOYSA-N 0.000 description 1
LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
QQKAZZAULUMMKR-UHFFFAOYSA-N 2-n-hydroxybenzene-1,2-dicarboxamide Chemical compound NC(=O)C1=CC=CC=C1C(=O)NO QQKAZZAULUMMKR-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
AAXFXBIGBZUQDH-UHFFFAOYSA-N 5-oxo-6h-pyrido[2,3-d]pyrimidine-6-carboxylic acid Chemical compound C1=NC=C2C(=O)C(C(=O)O)C=NC2=N1 AAXFXBIGBZUQDH-UHFFFAOYSA-N 0.000 description 1
208000019881 Abnormality of the kidney Diseases 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000588697 Enterobacter cloacae Species 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
201000008225 Klebsiella pneumonia Diseases 0.000 description 1
241000588747 Klebsiella pneumoniae Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
206010035717 Pneumonia klebsiella Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
241000607715 Serratia marcescens Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
241000186064 Trueperella pyogenes Species 0.000 description 1
239000012345 acetylating agent Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000005236 alkanoylamino group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
125000005530 alkylenedioxy group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000005388 borosilicate glass Substances 0.000 description 1
YSMHTFWPDRJCMN-UHFFFAOYSA-N butan-2-yl carbonochloridate Chemical compound CCC(C)OC(Cl)=O YSMHTFWPDRJCMN-UHFFFAOYSA-N 0.000 description 1
RSYNHXZMASRGMC-UHFFFAOYSA-N butan-2-yl hydrogen carbonate Chemical compound CCC(C)OC(O)=O RSYNHXZMASRGMC-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
238000012754 cardiac puncture Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
210000004534 cecum Anatomy 0.000 description 1
229940106164 cephalexin Drugs 0.000 description 1
AVGYWQBCYZHHPN-CYJZLJNKSA-N cephalexin 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=CC=C1 AVGYWQBCYZHHPN-CYJZLJNKSA-N 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
230000003118 histopathologic effect Effects 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000007689 inspection Methods 0.000 description 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000003902 lesion Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
244000005700 microbiome Species 0.000 description 1
238000002156 mixing Methods 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
ZZPZLAOFCDYFRB-UHFFFAOYSA-N n,n-dimethylpyrido[3,2-d]pyrimidin-2-amine Chemical class N1=CC=CC2=NC(N(C)C)=NC=C21 ZZPZLAOFCDYFRB-UHFFFAOYSA-N 0.000 description 1
LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
JOHZPMXAZQZXHR-UHFFFAOYSA-N pipemidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCNCC1 JOHZPMXAZQZXHR-UHFFFAOYSA-N 0.000 description 1
229960001732 pipemidic acid Drugs 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
AHIHJODVQGBOND-UHFFFAOYSA-N propan-2-yl hydrogen carbonate Chemical compound CC(C)OC(O)=O AHIHJODVQGBOND-UHFFFAOYSA-N 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
238000000746 purification Methods 0.000 description 1
YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
231100000456 subacute toxicity Toxicity 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

BE178882A 1976-06-30 1977-06-29 Nouveaux composes de penicilline BE856243A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP7808576A JPS535184A (en)	1976-06-30	1976-06-30	N-acylpenicillin derivatives

Publications (1)

Publication Number	Publication Date
BE856243A true BE856243A (fr)	1977-12-29

Family

ID=13651997

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE178882A BE856243A (fr)	1976-06-30	1977-06-29	Nouveaux composes de penicilline

Country Status (3)

Country	Link
JP (1)	JPS535184A (ja)
BE (1)	BE856243A (ja)
ZA (1)	ZA773800B (ja)

1976
- 1976-06-30 JP JP7808576A patent/JPS535184A/ja active Pending
1977
- 1977-06-24 ZA ZA00773800A patent/ZA773800B/xx unknown
- 1977-06-29 BE BE178882A patent/BE856243A/fr unknown

Also Published As

Publication number	Publication date
JPS535184A (en)	1978-01-18
ZA773800B (en)	1978-05-30

Publication	Publication Date	Title
KR0180798B1 (ko)	1999-03-20	결정성 페니실린 유도체, 그의 제법 및 용도
FR2466467A1 (fr)	1981-04-10	Pentahydrate de cephalosporine, son procede de preparation et son application en therapeutique
US3483188A (en)	1969-12-09	6-(alpha - 3 - allophanamidophenylacetamido) and 6 - (alpha - 3 - allophanamidothienylacetamido)-penicillanic acids
FR2509310A1 (fr)	1983-01-14	Nouvelles cephalosporines, leur procede de preparation et leur application en therapeutique
FR2512449A1 (fr)	1983-03-11	Quinoleinium-betaines de cephalosporine et leur application pharmacolique
DK150201B (da)	1987-01-05	Alfa-azido-n-acyl-6-aminopenicillansyreester til anvendelse ved fremstilling af den tilsvarende alfa-aminoforbindelse
EP0049119B1 (en)	1986-01-15	Cephalosporin derivatives, a process for their preparation and compositions containing them
FR2512448A1 (fr)	1983-03-11	Isoquinoleinium-betaines de cephalosporine et son application pharmaceutique
FR2466469A1 (fr)	1981-04-10	Bischlorhydrate de cephalosporine, son procede de preparation et ses applications, notamment en therapeutique
MC1838A1 (fr)	1988-06-03	Composes beta lactame,la methode de sa preparation et la composition pharmacologique pour la therapie des maladies infectieuses et les moyens de sa synthese
US3481922A (en)	1969-12-02	6-(alpha - 3 - acylthioureidophenylacetamido)-and 6 - (alpha-3-acylthioureidothienylacetamido)-penicillanic acids
KR850001936B1 (ko)	1985-12-31	페니실란오일옥시메틸 페니실라네이트 1, 1, 1', 1'-테트라옥사이드의 제조 방법
CH621125A5 (ja)	1981-01-15
NO802686L (no)	1978-10-24	Fremgangsmaate for fremstilling av en ester av et klavulansyreamin
LU82429A1 (fr)	1980-07-31	Derives heterocycliques de cephalosporines oxy-imino-substituees
MC1991A1 (fr)	1989-11-30	Esters d'acides carboxyliques pharmacologiquement actifs
US4231928A (en)	1980-11-04	Antibacterial agents
US4104469A (en)	1978-08-01	7-(Syn-α-alkoxy-iminofuryl)acetamido-3-(2-methyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids
BE856243A (fr)	1977-12-29	Nouveaux composes de penicilline
BE821243A (fr)	1975-04-18	Derives de la penicilline
US4103011A (en)	1978-07-25	Novel penicillin compounds and process for preparation thereof
FR2468608A1 (fr)	1981-05-08	Derives de la 1-oxadethiacephalosporine, leur procede de production et compositions anti-bacteriennes les contenant
FR2591598A1 (fr)	1987-06-19	Nouveaux derives d'acide ceph-3-em-4-carboxylique, leur preparation et medicaments les contenant
JPS63154622A (ja)	1988-06-27	セフアロスポリン誘導体を有効成分とする哺乳動物用抗菌剤
BE890499A (fr)	1982-03-25	Nouvelles cephalosporines, leur procede de preparation et leur application en therapeutique