SU1468425A3 - Способ получени производных 6-(1-ацил-1-оксиметил)пенициллановой кислоты,или ее солей с щелочными металлами,или ее сложных пивалоилоксиметиловых эфиров - Google Patents

Способ получени производных 6-(1-ацил-1-оксиметил)пенициллановой кислоты,или ее солей с щелочными металлами,или ее сложных пивалоилоксиметиловых эфиров Download PDF

Info

Publication number: SU1468425A3
Authority: SU; USSR - Soviet Union
Prior art keywords: oxo; penicillanate; hydroxy; ethyl; ethyl acetate
Prior art date: 1985-04-18

Application number

SU864027374A

Other languages

English (en)

Russian (ru)

Inventor

Эндрю Рид Ш Лоуренс

Рид Анне (Наследник)

Original Assignee

Пфайзер Инк. (Фирма)

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.)

1985-04-18

Filing date

1986-04-17

Publication date

1989-03-23

1986-04-17 Application filed by Пфайзер Инк. (Фирма) filed Critical Пфайзер Инк. (Фирма)

1989-03-23 Application granted granted Critical

1989-03-23 Publication of SU1468425A3 publication Critical patent/SU1468425A3/ru

Links

229910052783 alkali metal Inorganic materials 0.000 title claims description 5
150000003839 salts Chemical class 0.000 title claims description 5
238000000034 method Methods 0.000 title claims description 4
150000001340 alkali metals Chemical class 0.000 title claims description 3
150000002148 esters Chemical class 0.000 title claims 2
OPEGYZAATHKDEM-HCWXCVPCSA-N (2r,4s)-2-[(r)-carboxy(formamido)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid Chemical compound CC1(C)S[C@H]([C@H](NC=O)C(O)=O)N[C@H]1C(O)=O OPEGYZAATHKDEM-HCWXCVPCSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 26
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims abstract description 4
239000000047 product Substances 0.000 claims description 110
-1 phenoxy, benzyloxycarbonylamino Chemical group 0.000 claims description 37
239000002253 acid Substances 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 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
101000617550 Dictyostelium discoideum Presenilin-A Proteins 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
230000003197 catalytic effect Effects 0.000 claims 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
230000032050 esterification Effects 0.000 claims 1
238000005886 esterification reaction Methods 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
239000012467 final product Substances 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
238000007327 hydrogenolysis reaction Methods 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 250
238000005160 1H NMR spectroscopy Methods 0.000 description 67
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 65
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 58
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 54
229910052700 potassium Inorganic materials 0.000 description 54
239000011591 potassium Substances 0.000 description 54
239000000243 solution Substances 0.000 description 46
239000000203 mixture Substances 0.000 description 45
238000006243 chemical reaction Methods 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
238000002329 infrared spectrum Methods 0.000 description 20
239000010410 layer Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 18
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
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 16
229910052708 sodium Inorganic materials 0.000 description 16
239000011734 sodium Substances 0.000 description 16
238000000605 extraction Methods 0.000 description 12
230000000844 anti-bacterial effect Effects 0.000 description 11
238000012360 testing method Methods 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
244000005700 microbiome Species 0.000 description 9
238000003756 stirring Methods 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000007710 freezing Methods 0.000 description 8
230000008014 freezing Effects 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000003242 anti bacterial agent Substances 0.000 description 6
239000003814 drug Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000002054 inoculum Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
229920001817 Agar Polymers 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
239000008272 agar Substances 0.000 description 5
230000003115 biocidal effect Effects 0.000 description 5
239000003480 eluent Substances 0.000 description 5
LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 5
238000001914 filtration Methods 0.000 description 5
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000011343 solid material Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000012065 filter cake Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
238000005406 washing Methods 0.000 description 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
239000003782 beta lactam antibiotic agent Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000002024 ethyl acetate extract Substances 0.000 description 3
SLFUXNFVAANERW-UHFFFAOYSA-N ethyl hexanoate;potassium Chemical compound [K].CCCCCC(=O)OCC SLFUXNFVAANERW-UHFFFAOYSA-N 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
239000012267 brine Substances 0.000 description 2
238000009924 canning Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
238000007865 diluting Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
230000009036 growth inhibition Effects 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
231100000636 lethal dose Toxicity 0.000 description 2
238000005259 measurement Methods 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000003973 paint Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000010076 replication Effects 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000002023 wood Substances 0.000 description 2
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
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 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
108090000204 Dipeptidase 1 Proteins 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
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 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
102000006635 beta-lactamase Human genes 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000006261 foam material Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
230000000155 isotopic effect Effects 0.000 description 1
CECJUTNNLPJONZ-UHFFFAOYSA-N methyl 4-(2-acetyloxyacetyl)benzoate Chemical compound COC(=O)C1=CC=C(C(=O)COC(C)=O)C=C1 CECJUTNNLPJONZ-UHFFFAOYSA-N 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
KDLHZDBZIXYQEI-VENIDDJXSA-N palladium-100 Chemical compound [100Pd] KDLHZDBZIXYQEI-VENIDDJXSA-N 0.000 description 1
YCOFRPYSZKIPBQ-UHFFFAOYSA-N penicillic acid Natural products COC1=CC(=O)OC1(O)C(C)=C YCOFRPYSZKIPBQ-UHFFFAOYSA-N 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
VOUGEZYPVGAPBB-UHFFFAOYSA-N penicillin acid Natural products OC(=O)C=C(OC)C(=O)C(C)=C VOUGEZYPVGAPBB-UHFFFAOYSA-N 0.000 description 1
RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
239000011148 porous material Substances 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000028327 secretion Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
230000002195 synergetic effect Effects 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
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

SU864027374A 1985-04-18 1986-04-17 Способ получени производных 6-(1-ацил-1-оксиметил)пенициллановой кислоты,или ее солей с щелочными металлами,или ее сложных пивалоилоксиметиловых эфиров SU1468425A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US72485785A	1985-04-18	1985-04-18

Publications (1)

Publication Number	Publication Date
SU1468425A3 true SU1468425A3 (ru)	1989-03-23

Family

ID=24912209

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU864027374A SU1468425A3 (ru)	1985-04-18	1986-04-17	Способ получени производных 6-(1-ацил-1-оксиметил)пенициллановой кислоты,или ее солей с щелочными металлами,или ее сложных пивалоилоксиметиловых эфиров

Country Status (27)

Country	Link
US (1)	US4675186A (2)
EP (1)	EP0201221B1 (2)
JP (1)	JPS61243089A (2)
KR (1)	KR880000974B1 (2)
CN (1)	CN1003712B (2)
AT (1)	ATE55133T1 (2)
AU (1)	AU565926B2 (2)
CA (1)	CA1270814A (2)
CS (1)	CS255871B2 (2)
DD (1)	DD258020A5 (2)
DE (1)	DE3673057D1 (2)
DK (1)	DK175186A (2)
EG (1)	EG18288A (2)
ES (1)	ES8800233A1 (2)
FI (1)	FI85272C (2)
GR (1)	GR860997B (2)
HU (1)	HU196807B (2)
IE (1)	IE58666B1 (2)
IL (1)	IL78509A (2)
NO (2)	NO861508L (2)
NZ (1)	NZ215863A (2)
PH (2)	PH22795A (2)
PL (1)	PL147619B1 (2)
PT (1)	PT82401B (2)
SU (1)	SU1468425A3 (2)
YU (1)	YU45013B (2)
ZA (1)	ZA862876B (2)

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FR2956400A1 (fr) *	2010-02-15	2011-08-19	Finorga	Procede de preparation de composes adamantyles
CN109422765B (zh) *	2017-09-05	2020-08-28	香港理工大学深圳研究院	C类β-内酰胺酶抑制剂及其制备方法和应用

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1986
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- 1986-04-14 AT AT86302745T patent/ATE55133T1/de not_active IP Right Cessation
- 1986-04-14 DE DE8686302745T patent/DE3673057D1/de not_active Expired - Lifetime
- 1986-04-14 EP EP86302745A patent/EP0201221B1/en not_active Expired - Lifetime
- 1986-04-15 CS CS862759A patent/CS255871B2/cs not_active IP Right Cessation
- 1986-04-15 IL IL78509A patent/IL78509A/xx not_active IP Right Cessation
- 1986-04-15 GR GR860997A patent/GR860997B/el unknown
- 1986-04-16 CA CA000506790A patent/CA1270814A/en not_active Expired - Lifetime
- 1986-04-16 YU YU622/86A patent/YU45013B/xx unknown
- 1986-04-16 PT PT82401A patent/PT82401B/pt not_active IP Right Cessation
- 1986-04-16 PH PH33664A patent/PH22795A/en unknown
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- 1986-04-18 JP JP61089867A patent/JPS61243089A/ja active Granted
- 1986-04-18 DD DD86289375A patent/DD258020A5/de not_active IP Right Cessation
1987
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Also Published As

Publication number	Publication date
DK175186D0 (da)	1986-04-17
CN86102736A (zh)	1986-10-15
FI85272B (fi)	1991-12-13
HUT40669A (en)	1987-01-28
JPH0534358B2 (2)	1993-05-21
CS255871B2 (en)	1988-03-15
PH23560A (en)	1989-08-25
AU5631886A (en)	1986-10-23
PT82401A (en)	1986-05-01
IL78509A0 (en)	1986-08-31
ZA862876B (en)	1987-11-25
CA1270814A (en)	1990-06-26
EG18288A (en)	1992-10-30
PH22795A (en)	1988-12-12
CS275986A2 (en)	1987-07-16
IE861014L (en)	1986-10-18
NO873599D0 (no)	1987-08-26
NO873599L (no)	1986-10-20
NO861508L (no)	1986-10-20
YU62286A (en)	1988-02-29
NZ215863A (en)	1988-07-28
FI85272C (fi)	1992-03-25
HU196807B (en)	1989-01-30
JPS61243089A (ja)	1986-10-29
DE3673057D1 (de)	1990-09-06
GR860997B (en)	1986-08-12
ES8800233A1 (es)	1987-10-16
KR880000974B1 (ko)	1988-06-07
FI861630A0 (fi)	1986-04-17
AU565926B2 (en)	1987-10-01
EP0201221A1 (en)	1986-11-12
DK175186A (da)	1986-10-19
CN1003712B (zh)	1989-03-29
DD258020A5 (de)	1988-07-06
YU45013B (en)	1991-06-30
ES554118A0 (es)	1987-10-16
ATE55133T1 (de)	1990-08-15
EP0201221B1 (en)	1990-08-01
FI861630L (fi)	1986-10-19
US4675186A (en)	1987-06-23
IE58666B1 (en)	1993-11-03
KR860008187A (ko)	1986-11-12
IL78509A (en)	1991-03-10
PT82401B (pt)	1988-08-17
PL147619B1 (en)	1989-07-31

Publication	Publication Date	Title
CH646177A5 (de)	1984-11-15	Bisester von methandiol mit penicillinen und penicillansaeure-1,1-dioxid.
NO145883B (no)	1982-03-08	Analogifremgangsmaate ved fremstilling av terapeutisk aktive 7-methoxy-7-acylamino-cefalosporansyrederivater.
IE51430B1 (en)	1986-12-24	Thiazoline derivatives and processes for their manufacture
SU1468425A3 (ru)	1989-03-23	Способ получени производных 6-(1-ацил-1-оксиметил)пенициллановой кислоты,или ее солей с щелочными металлами,или ее сложных пивалоилоксиметиловых эфиров
US4155912A (en)	1979-05-22	2-Methylpenem-3-carboxylic acid antibiotics
NO820897L (no)	1982-09-24	Fremgangsmaate for fremstilling av antibakterielle bis-estere av 1,1-alkandioler med to beta-laktamgrupper
NO750668L (2)	1973-09-14
EP0003069B1 (en)	1981-05-20	Pseudomonic acid c, pharmaceutically acceptable salts or esters thereof, processes for their preparation and pharmaceutical or veterinary compositions containing them
CA1269369A (en)	1990-05-22	Derivatives of the oligosaccharide antibiotic complex 13-384, their preparation and pharmaceutical compositions containing them
DK159852B (da)	1990-12-17	Fremgangsmaade til fremstilling af penicillansyre-1,1-dioxid eller basesalte eller in vivo let hydrolyserbare estre deraf
Broom et al.	1990	6-(SUBSTITUTED METHYLENE) PENEMS, POTENT BROAD SPECTRUM INHIBITORS OF BACTERIAL β-LACTAMASE II. RACEMIC FURYL AND THIENYL DERIVATIVES
DE2057381A1 (de)	1971-06-03	2-Substituierte Thiazolidinverbindungen
FI79112C (fi)	1989-11-10	6-aminoalkylpenicillansyra-1,1-dioxider och deras derivat som -laktamas-inhibitorer.
CA1148940A (en)	1983-06-28	Penicillin derivatives
EP0112283B1 (de)	1987-08-12	Heterocyclylthioverbindungen, Verfahren zu ihrer Herstellung, pharmazeutische Präparate, welche diese Verbindungen enthalten, und Verwendung von letzteren
EP0003415A2 (en)	1979-08-08	Beta-Lactam compounds, processes for their preparation,compositions containing them and intermediates of use in their preparation
EP0421752A2 (en)	1991-04-10	Substituted acrylamido-penicillanic acid derivatives
US4540580A (en)	1985-09-10	2-[(1'R)-1'-Aminoalkyl]penems
EP0125207A1 (de)	1984-11-14	2-Tetrazolylpropyl-2-penem-Verbindungen, Verfahren zu ihrer Herstellung, pharmazeutische Präparate, welche diese Verbindungen enthalten, und Verwendung von letzteren
US3950350A (en)	1976-04-13	Penam-dimethylsulfoxide complex
GB1570986A (en)	1980-07-09	Derivatives of thienamycin and its isomers
KR810000288B1 (ko)	1981-03-30	몬산 및 이소몬산 유도체의 제조방법
SU1313350A3 (ru)	1987-05-23	Способ получени производных 1,1-диоксида-6-аминоалкил-пенициллановой кислоты
SE466203B (sv)	1992-01-13	Estrar foer framstaellning av en beta-laktamas-inhibitor
EP0041813A1 (en)	1981-12-16	Penicillin derivatives, processes for their preparation and compositions containing them