FI66004C - Foerfarande foer framstaellning av beta-laktamantibiotika anvaendbara saosom laekemedel - Google Patents
Foerfarande foer framstaellning av beta-laktamantibiotika anvaendbara saosom laekemedel Download PDFInfo
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- FI66004C FI66004C FI753333A FI753333A FI66004C FI 66004 C FI66004 C FI 66004C FI 753333 A FI753333 A FI 753333A FI 753333 A FI753333 A FI 753333A FI 66004 C FI66004 C FI 66004C
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- Finland
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- 239000003782 beta lactam antibiotic agent Substances 0.000 title claims description 10
- 239000002132 β-lactam antibiotic Substances 0.000 title claims description 9
- 229940124586 β-lactam antibiotics Drugs 0.000 title claims description 9
- -1 p-hydroxylphenyl Chemical group 0.000 claims description 113
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 231100000252 nontoxic Toxicity 0.000 claims description 6
- 230000003000 nontoxic effect Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000001540 azides Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000002516 radical scavenger Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 110
- 239000011734 sodium Substances 0.000 description 106
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 96
- 229910052708 sodium Inorganic materials 0.000 description 86
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 86
- 229910001868 water Inorganic materials 0.000 description 84
- 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 description 81
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- 239000000460 chlorine Chemical group 0.000 description 57
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- 239000005662 Paraffin oil Substances 0.000 description 47
- 229930182555 Penicillin Natural products 0.000 description 40
- 239000000243 solution Substances 0.000 description 39
- 238000002329 infrared spectrum Methods 0.000 description 37
- 229940049954 penicillin Drugs 0.000 description 37
- 150000003952 β-lactams Chemical class 0.000 description 37
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 36
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 30
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 29
- 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 29
- 239000000047 product Substances 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 229960003311 ampicillin trihydrate Drugs 0.000 description 27
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 27
- 239000002244 precipitate Substances 0.000 description 27
- 229950004030 cefaloglycin Drugs 0.000 description 26
- 150000002960 penicillins Chemical class 0.000 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 description 25
- 229930186147 Cephalosporin Natural products 0.000 description 24
- 229940124587 cephalosporin Drugs 0.000 description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 22
- 150000001780 cephalosporins Chemical class 0.000 description 22
- 159000000000 sodium salts Chemical class 0.000 description 22
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 22
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 21
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 15
- 235000010288 sodium nitrite Nutrition 0.000 description 15
- 239000002585 base Substances 0.000 description 13
- 239000005051 trimethylchlorosilane Substances 0.000 description 13
- 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 10
- 239000007858 starting material Substances 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 10
- VRIKLWVRINZPSR-UHFFFAOYSA-N 1-aminoimidazolidin-2-one;hydrochloride Chemical compound Cl.NN1CCNC1=O VRIKLWVRINZPSR-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 229940056360 penicillin g Drugs 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- RPBAFSBGYDKNRG-NJBDSQKTSA-N epicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CCC=CC1 RPBAFSBGYDKNRG-NJBDSQKTSA-N 0.000 description 8
- 229960002457 epicillin Drugs 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 229960004920 amoxicillin trihydrate Drugs 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- ZWXXVWSSKFZMOJ-UHFFFAOYSA-N 3-(furan-2-ylmethylideneamino)-2-oxoimidazolidine-1-carbonyl chloride Chemical compound O=C1N(C(=O)Cl)CCN1N=CC1=CC=CO1 ZWXXVWSSKFZMOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 230000020477 pH reduction Effects 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
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- 150000007529 inorganic bases Chemical class 0.000 description 5
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- 235000019371 penicillin G benzathine Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- DHIVBEZCBBHIPZ-UHFFFAOYSA-N 1-aminoimidazolidin-2-one Chemical compound NN1CCNC1=O DHIVBEZCBBHIPZ-UHFFFAOYSA-N 0.000 description 4
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 4
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- RLGBRPHLXPWFHQ-UHFFFAOYSA-N 3-(cinnamylideneamino)-2-oxoimidazolidine-1-carbonyl chloride Chemical compound O=C1N(C(=O)Cl)CCN1N=CC=CC1=CC=CC=C1 RLGBRPHLXPWFHQ-UHFFFAOYSA-N 0.000 description 3
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- NASVHNJQONZOGA-UHFFFAOYSA-N 3-[(5-methylfuran-2-yl)methylideneamino]-2-oxoimidazolidine-1-carbonyl chloride Chemical compound ClC(=O)N1C(N(CC1)N=CC1=CC=C(O1)C)=O NASVHNJQONZOGA-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
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- FUEAILYGIAMTLM-UHFFFAOYSA-N 3-[(4-fluorophenyl)methylideneamino]-2-oxoimidazolidine-1-carbonyl chloride Chemical compound C1=CC(F)=CC=C1C=NN1C(=O)N(C(Cl)=O)CC1 FUEAILYGIAMTLM-UHFFFAOYSA-N 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- FNEDHAVUXWEPMP-UHFFFAOYSA-M sodium;2-methylhexanoate Chemical compound [Na+].CCCCC(C)C([O-])=O FNEDHAVUXWEPMP-UHFFFAOYSA-M 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring 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
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742456307 DE2456307A1 (de) | 1974-11-28 | 1974-11-28 | Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2456307 | 1974-11-28 | ||
| DE2512998 | 1975-03-25 | ||
| DE19752512998 DE2512998A1 (de) | 1975-03-25 | 1975-03-25 | Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE19752525541 DE2525541C2 (de) | 1975-06-07 | 1975-06-07 | β-Lactam-Antibiotica, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel |
| DE2525541 | 1975-06-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI753333A7 FI753333A7 (en, 2012) | 1976-05-29 |
| FI66004B FI66004B (fi) | 1984-04-30 |
| FI66004C true FI66004C (fi) | 1984-08-10 |
Family
ID=27186174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI753333A FI66004C (fi) | 1974-11-28 | 1975-11-26 | Foerfarande foer framstaellning av beta-laktamantibiotika anvaendbara saosom laekemedel |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4147693A (en, 2012) |
| JP (2) | JPS5182286A (en, 2012) |
| AR (1) | AR210103A1 (en, 2012) |
| AT (1) | AT342196B (en, 2012) |
| AU (1) | AU499337B2 (en, 2012) |
| CA (1) | CA1064020A (en, 2012) |
| CH (1) | CH623326A5 (en, 2012) |
| DD (1) | DD124736A5 (en, 2012) |
| DK (1) | DK535675A (en, 2012) |
| ES (1) | ES443008A1 (en, 2012) |
| FI (1) | FI66004C (en, 2012) |
| FR (1) | FR2292471A1 (en, 2012) |
| GB (1) | GB1486349A (en, 2012) |
| HK (1) | HK19678A (en, 2012) |
| IE (1) | IE43813B1 (en, 2012) |
| IL (1) | IL48538A (en, 2012) |
| LU (1) | LU73873A1 (en, 2012) |
| NL (1) | NL7513746A (en, 2012) |
| NO (1) | NO753818L (en, 2012) |
| NZ (1) | NZ179347A (en, 2012) |
| RO (1) | RO68146A (en, 2012) |
| SE (1) | SE434513B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4061861A (en) * | 1976-06-21 | 1977-12-06 | Eli Lilly And Company | 7-[α-(2,3-DIHYDRO-2-OXO-1H-benzimidazol-1-ylcarbonyl-amino)arylacetamido]cephalosporins |
| JPS5326143A (en) * | 1976-08-24 | 1978-03-10 | Oki Electric Ind Co Ltd | Coupling method for op tical fiber |
| JPS5331690A (en) * | 1976-09-01 | 1978-03-25 | Shionogi & Co Ltd | Oxadithiacephalosporins |
| GB1584400A (en) * | 1976-12-24 | 1981-02-11 | Bayer Ag | (2-oxo-imidazoliden-1-yl(carbonylamino)-acetamido-cephalosporins and penicillins |
| DE2732283A1 (de) * | 1977-07-16 | 1979-01-25 | Bayer Ag | Beta-lactam-verbindungen |
| JPS5616489A (en) * | 1979-07-20 | 1981-02-17 | Ajinomoto Co Inc | Imidazolecarboxylic acid derivative |
| US4386199A (en) * | 1980-01-03 | 1983-05-31 | E. R. Squibb & Sons, Inc. | Cephalosporins having an imino substituted piperazindioncarbonylamino acyl sidechain |
| US4436904A (en) * | 1981-02-14 | 1984-03-13 | Kanto Ishi Pharmaceutical Co., Ltd. | Cephalosporins |
| DE3137038A1 (de) | 1981-09-17 | 1983-03-24 | Bayer Ag, 5090 Leverkusen | Ss-lactam antibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| GB8318846D0 (en) * | 1983-07-12 | 1983-08-10 | Fujisawa Pharmaceutical Co | Prophylactic/therapeutic agent against fish diseases |
| CN103360321B (zh) * | 2012-04-05 | 2016-09-21 | 北京勤邦生物技术有限公司 | 呋喃妥因代谢物半抗原及其制备方法和应用 |
| CN111995663B (zh) * | 2020-09-02 | 2023-07-28 | 重庆大学 | 一种含有N-氨基咪唑烷-2-酮结构的Ang-（1-7）多肽类似物 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH571524A5 (en, 2012) * | 1970-05-25 | 1976-01-15 | Bayer Ag | |
| US3974140A (en) * | 1970-05-25 | 1976-08-10 | Bayer Aktiengesellschaft | Ureidoacetamido-penicillins |
| US3980792A (en) * | 1970-05-25 | 1976-09-14 | Bayer Aktiengesellschaft | Ureidoacetamido-penicillins |
| CH562249A5 (en, 2012) * | 1970-05-25 | 1975-05-30 | Bayer Ag | |
| US3939149A (en) * | 1970-05-25 | 1976-02-17 | Bayer Aktiengesellschaft | Ureidoacetamido-penicillins |
| US3732332A (en) * | 1970-10-16 | 1973-05-08 | Allied Chem | Production of low molecular weight polyanhydrides and epoxy compositions derived therefrom |
| US3974141A (en) * | 1971-10-23 | 1976-08-10 | Bayer Aktiengesellschaft | Penicillins |
| NL175419C (nl) * | 1971-10-23 | 1984-11-01 | Bayer Ag | Werkwijze ter bereiding of vervaardiging van antibiotisch werkzame farmaceutische preparaten, alsmede werkwijze ter bereiding van antibiotisch werkzame alfa-gesubstitueerde 6-(alfa-(3-acylureido)acetylamino) penicillanzuurderivaten. |
| US3974142A (en) * | 1971-10-23 | 1976-08-10 | Bayer Aktiengesellschaft | Penicillins |
| US3978056A (en) * | 1971-10-23 | 1976-08-31 | Bayer Aktiengesellschaft | Penicillins |
| BE790441A (fr) * | 1971-10-23 | 1973-04-24 | Bayer Ag | Nouvelles penicillines, leur procede de preparation et medicament les contenant |
| US3972870A (en) * | 1971-10-23 | 1976-08-03 | Bayer Aktiengesellschaft | Penicillins |
| US3983105A (en) * | 1971-10-23 | 1976-09-28 | Bayer Aktiengesellschaft | Penicillins |
| DE2354219A1 (de) * | 1973-10-30 | 1975-05-07 | Bayer Ag | Beta-lactam-antibiotica, ein verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
1975
- 1975-10-28 GB GB44296/75A patent/GB1486349A/en not_active Expired
- 1975-11-13 US US05/631,515 patent/US4147693A/en not_active Expired - Lifetime
- 1975-11-14 NO NO753818A patent/NO753818L/no unknown
- 1975-11-18 CA CA239,913A patent/CA1064020A/en not_active Expired
- 1975-11-24 CH CH1523375A patent/CH623326A5/de not_active IP Right Cessation
- 1975-11-25 IL IL48538A patent/IL48538A/xx unknown
- 1975-11-25 NZ NZ179347A patent/NZ179347A/xx unknown
- 1975-11-25 NL NL7513746A patent/NL7513746A/xx not_active Application Discontinuation
- 1975-11-26 ES ES443008A patent/ES443008A1/es not_active Expired
- 1975-11-26 JP JP50140877A patent/JPS5182286A/ja active Granted
- 1975-11-26 FI FI753333A patent/FI66004C/fi not_active IP Right Cessation
- 1975-11-26 LU LU73873A patent/LU73873A1/xx unknown
- 1975-11-26 DD DD189709A patent/DD124736A5/xx unknown
- 1975-11-26 JP JP50140878A patent/JPS6043332B2/ja not_active Expired
- 1975-11-26 RO RO7584030A patent/RO68146A/ro unknown
- 1975-11-27 DK DK535675A patent/DK535675A/da not_active Application Discontinuation
- 1975-11-27 SE SE7513378A patent/SE434513B/xx unknown
- 1975-11-27 IE IE2588/75A patent/IE43813B1/en unknown
- 1975-11-28 AT AT907275A patent/AT342196B/de not_active IP Right Cessation
- 1975-11-28 FR FR7536543A patent/FR2292471A1/fr active Granted
- 1975-11-28 AR AR261391A patent/AR210103A1/es active
- 1975-11-28 AU AU87085/75A patent/AU499337B2/en not_active Expired
-
1978
- 1978-04-13 HK HK196/78A patent/HK19678A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1486349A (en) | 1977-09-21 |
| SE434513B (sv) | 1984-07-30 |
| DK535675A (da) | 1976-05-29 |
| FI753333A7 (en, 2012) | 1976-05-29 |
| NL7513746A (nl) | 1976-06-01 |
| US4147693A (en) | 1979-04-03 |
| SE7513378L (sv) | 1976-05-31 |
| AT342196B (de) | 1978-03-28 |
| ATA907275A (de) | 1977-07-15 |
| IE43813L (en) | 1976-05-28 |
| CA1064020A (en) | 1979-10-09 |
| ES443008A1 (es) | 1977-05-01 |
| IE43813B1 (en) | 1981-06-03 |
| NZ179347A (en) | 1978-04-28 |
| IL48538A0 (en) | 1976-01-30 |
| NO753818L (en, 2012) | 1976-05-31 |
| FR2292471B1 (en, 2012) | 1981-12-31 |
| HK19678A (en) | 1978-04-20 |
| JPS5182286A (en) | 1976-07-19 |
| FR2292471A1 (fr) | 1976-06-25 |
| AU499337B2 (en) | 1979-04-12 |
| JPS6114151B2 (en, 2012) | 1986-04-17 |
| CH623326A5 (en, 2012) | 1981-05-29 |
| JPS5176438A (en, 2012) | 1976-07-02 |
| AU8708575A (en) | 1977-06-02 |
| AR210103A1 (es) | 1977-06-30 |
| RO68146A (ro) | 1980-04-15 |
| IL48538A (en) | 1979-07-25 |
| JPS6043332B2 (ja) | 1985-09-27 |
| LU73873A1 (en, 2012) | 1976-09-06 |
| FI66004B (fi) | 1984-04-30 |
| DD124736A5 (en, 2012) | 1977-03-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: BAYER AKTIENGESELLSCHAFT |