NO842248L - Fremgangsmaate for fremstilling av 6-aminometyl-penicillansyre-1,1-dioksyd-derivater - Google Patents

Fremgangsmaate for fremstilling av 6-aminometyl-penicillansyre-1,1-dioksyd-derivater

Info

Publication number: NO842248L
Authority: NO; Norway
Prior art keywords: formula; compound; benzyl; title product; mol
Prior art date: 1983-06-06

Application number

NO842248A

Other languages

English (en)

Norwegian (no)

Inventor

Donald Klein Pirie

Robert Alfred Volkmann

Edward Fox Kleinmann

Original Assignee

Pfizer

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.)

1983-06-06

Filing date

1984-06-05

Publication date

1984-12-07

1984-06-05 Application filed by Pfizer filed Critical Pfizer

1984-12-07 Publication of NO842248L publication Critical patent/NO842248L/no

Links

238000000034 method Methods 0.000 title claims abstract description 62
150000001875 compounds Chemical class 0.000 claims abstract description 81
230000004962 physiological condition Effects 0.000 claims abstract description 15
230000008569 process Effects 0.000 claims abstract description 7
239000000203 mixture Substances 0.000 claims description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 42
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
-1 pivaloyloxymethyl Chemical group 0.000 claims description 19
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 16
229910000564 Raney nickel Inorganic materials 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
238000007327 hydrogenolysis reaction Methods 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 5
238000005984 hydrogenation reaction Methods 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000005643 gamma-butyrolacton-4-yl group Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Chemical group 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 2
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 11
150000002148 esters Chemical class 0.000 abstract description 11
150000003839 salts Chemical class 0.000 abstract description 11
239000000543 intermediate Substances 0.000 abstract description 6
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 2
239000003781 beta lactamase inhibitor Substances 0.000 abstract 1
229940126813 beta-lactamase inhibitor Drugs 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 171
239000000047 product Substances 0.000 description 106
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
230000003115 biocidal effect Effects 0.000 description 15
239000010410 layer Substances 0.000 description 15
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
239000012044 organic layer Substances 0.000 description 14
239000000243 solution Substances 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
238000001704 evaporation Methods 0.000 description 12
230000008020 evaporation Effects 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
238000003756 stirring Methods 0.000 description 12
239000007868 Raney catalyst Substances 0.000 description 11
239000012267 brine Substances 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
239000002253 acid Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000463 material Substances 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
FKENQMMABCRJMK-RITPCOANSA-N sulbactam Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)N2C(=O)C[C@H]21 FKENQMMABCRJMK-RITPCOANSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
229910001868 water Inorganic materials 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
239000003480 eluent Substances 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
229930182555 Penicillin Natural products 0.000 description 6
239000003782 beta lactam antibiotic agent Substances 0.000 description 6
GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
239000006260 foam Substances 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
PONHABAUOQTKJA-UHFFFAOYSA-N n-ethoxymethanimine Chemical compound CCON=C PONHABAUOQTKJA-UHFFFAOYSA-N 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
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 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
125000002091 cationic group Chemical group 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012535 impurity Substances 0.000 description 4
229940049954 penicillin Drugs 0.000 description 4
OSORMYZMWHVFOZ-UHFFFAOYSA-N phenethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCC1=CC=CC=C1 OSORMYZMWHVFOZ-UHFFFAOYSA-N 0.000 description 4
230000009467 reduction Effects 0.000 description 4
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000004108 freeze drying Methods 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
YEUNNNXEJUBNCO-UHFFFAOYSA-N n-phenylmethoxymethanimine Chemical compound C=NOCC1=CC=CC=C1 YEUNNNXEJUBNCO-UHFFFAOYSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 3
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
208000035143 Bacterial infection Diseases 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
239000007818 Grignard reagent Substances 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
208000022362 bacterial infectious disease Diseases 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
150000004795 grignard reagents Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
244000005700 microbiome Species 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
150000002960 penicillins Chemical class 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000007790 scraping Methods 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000001665 trituration Methods 0.000 description 2
NDQQRRVKUBPTHQ-QBIQUQHTSA-N (2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO NDQQRRVKUBPTHQ-QBIQUQHTSA-N 0.000 description 1
XGINAUQXFXVBND-UHFFFAOYSA-N 1,2,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrimidine Chemical compound N1CC=CN2CCCC21 XGINAUQXFXVBND-UHFFFAOYSA-N 0.000 description 1
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
YVRGKFXJZCTTRB-UHFFFAOYSA-N 1-chloroethyl ethyl carbonate Chemical compound CCOC(=O)OC(C)Cl YVRGKFXJZCTTRB-UHFFFAOYSA-N 0.000 description 1
RUHJZSZTSCSTCC-UHFFFAOYSA-N 2-(bromomethyl)naphthalene Chemical compound C1=CC=CC2=CC(CBr)=CC=C21 RUHJZSZTSCSTCC-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
CLMSHAWYULIVFQ-UHFFFAOYSA-N 3-bromo-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(Br)OC(=O)C2=C1 CLMSHAWYULIVFQ-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-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
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
ZDKRMIJRCHPKLW-UHFFFAOYSA-N benzyl methanesulfonate Chemical compound CS(=O)(=O)OCC1=CC=CC=C1 ZDKRMIJRCHPKLW-UHFFFAOYSA-N 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
NHYXMAKLBXBVEO-UHFFFAOYSA-N bromomethyl acetate Chemical compound CC(=O)OCBr NHYXMAKLBXBVEO-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Chemical class 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
239000003245 coal Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
KQBWUPMFKBDNJJ-UHFFFAOYSA-N n-methoxymethanimine Chemical compound CON=C KQBWUPMFKBDNJJ-UHFFFAOYSA-N 0.000 description 1
HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000011591 potassium Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000012264 purified product Substances 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000000935 solvent evaporation Methods 0.000 description 1
ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 description 1
238000005406 washing Methods 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

NO842248A 1983-06-06 1984-06-05 Fremgangsmaate for fremstilling av 6-aminometyl-penicillansyre-1,1-dioksyd-derivater NO842248L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/501,475 US4499017A (en)	1983-06-06	1983-06-06	Beta-lactamase inhibiting 6-(alkoxyamino-methyl) penicillanic acid 1,1-dioxide and derivatives

Publications (1)

Publication Number	Publication Date
NO842248L true NO842248L (no)	1984-12-07

Family

ID=23993709

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO842248A NO842248L (no)	1983-06-06	1984-06-05	Fremgangsmaate for fremstilling av 6-aminometyl-penicillansyre-1,1-dioksyd-derivater

Country Status (21)

Country	Link
US (1)	US4499017A (el)
EP (1)	EP0128037B1 (el)
JP (1)	JPS606693A (el)
KR (1)	KR870000312B1 (el)
AT (1)	ATE24512T1 (el)
AU (1)	AU545467B2 (el)
CA (1)	CA1247597A (el)
DE (1)	DE3461800D1 (el)
DK (1)	DK275884A (el)
ES (1)	ES533147A0 (el)
FI (1)	FI842255A (el)
GR (1)	GR82214B (el)
HU (1)	HU193573B (el)
IL (1)	IL72003A (el)
NO (1)	NO842248L (el)
NZ (1)	NZ208381A (el)
PH (2)	PH21372A (el)
PL (1)	PL144040B1 (el)
PT (1)	PT78689A (el)
YU (1)	YU97084A (el)
ZA (1)	ZA844184B (el)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8928373D0 (en) *	1989-12-15	1990-02-21	Erba Carlo Spa	Beta-lactam derivatives
JP4102664B2 (ja) *	2000-07-19	2008-06-18	ノバルティスアクチエンゲゼルシャフト	バルサルタン塩

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4234579A (en) *	1977-06-07	1980-11-18	Pfizer Inc.	Penicillanic acid 1,1-dioxides as β-lactamase inhibitors
DE2927004A1 (de) *	1979-07-04	1981-05-27	Bayer Ag, 5090 Leverkusen	Penicillansaeure-1,1-dioxide, ihre herstellung und ihre verwendung als arzneimittel als arzneimittel
US4287181A (en) *	1979-10-22	1981-09-01	Pfizer Inc.	Derivatives of 6β-hydroxyalkylpenicillanic acids as β-lactamase inhibitors
RO87705A (ro) *	1982-01-11	1985-10-31	Pfizer Inc,Us	Procedeu pentru prepararea unor derivati ai acidului 6-aminoalchilpenicilanic 1,1-dioxid

1983
- 1983-06-06 US US06/501,475 patent/US4499017A/en not_active Expired - Lifetime
1984
- 1984-06-04 EP EP84303734A patent/EP0128037B1/en not_active Expired
- 1984-06-04 DE DE8484303734T patent/DE3461800D1/de not_active Expired
- 1984-06-04 PL PL1984248043A patent/PL144040B1/pl unknown
- 1984-06-04 CA CA000455812A patent/CA1247597A/en not_active Expired
- 1984-06-04 PT PT78689A patent/PT78689A/pt unknown
- 1984-06-04 GR GR74907A patent/GR82214B/el unknown
- 1984-06-04 AT AT84303734T patent/ATE24512T1/de not_active IP Right Cessation
- 1984-06-04 DK DK275884A patent/DK275884A/da not_active Application Discontinuation
- 1984-06-04 IL IL72003A patent/IL72003A/xx not_active IP Right Cessation
- 1984-06-05 NZ NZ208381A patent/NZ208381A/en unknown
- 1984-06-05 FI FI842255A patent/FI842255A/fi not_active Application Discontinuation
- 1984-06-05 ZA ZA844184A patent/ZA844184B/xx unknown
- 1984-06-05 JP JP59115361A patent/JPS606693A/ja active Pending
- 1984-06-05 AU AU29076/84A patent/AU545467B2/en not_active Ceased
- 1984-06-05 KR KR1019840003122A patent/KR870000312B1/ko not_active IP Right Cessation
- 1984-06-05 HU HU842178A patent/HU193573B/hu unknown
- 1984-06-05 ES ES533147A patent/ES533147A0/es active Granted
- 1984-06-05 YU YU00970/84A patent/YU97084A/xx unknown
- 1984-06-05 NO NO842248A patent/NO842248L/no unknown
- 1984-06-06 PH PH30780A patent/PH21372A/en unknown
1986
- 1986-03-13 PH PH33521A patent/PH22842A/en unknown

Also Published As

Publication number	Publication date
CA1247597A (en)	1988-12-28
IL72003A0 (en)	1984-10-31
YU97084A (en)	1986-10-31
PL248043A1 (en)	1985-07-30
KR870000312B1 (ko)	1987-02-26
NZ208381A (en)	1987-05-29
PH22842A (en)	1989-01-19
AU2907684A (en)	1984-12-13
FI842255A (fi)	1984-12-07
KR850000446A (ko)	1985-02-27
ES8506720A1 (es)	1985-08-01
DK275884D0 (da)	1984-06-04
EP0128037B1 (en)	1986-12-30
DE3461800D1 (en)	1987-02-05
EP0128037A1 (en)	1984-12-12
HU193573B (en)	1987-10-28
GR82214B (el)	1984-12-13
ZA844184B (en)	1986-01-29
PH21372A (en)	1987-10-15
ES533147A0 (es)	1985-08-01
PT78689A (en)	1984-07-01
JPS606693A (ja)	1985-01-14
ATE24512T1 (de)	1987-01-15
US4499017A (en)	1985-02-12
AU545467B2 (en)	1985-07-18
HUT35266A (en)	1985-06-28
DK275884A (da)	1985-01-09
PL144040B1 (en)	1988-04-30
IL72003A (en)	1988-02-29
FI842255A0 (fi)	1984-06-05

Publication	Publication Date	Title
US4146643A (en)	1979-03-27	Increasing vigilance or treating cerebral insufficiency with substituted vincamines
US4155912A (en)	1979-05-22	2-Methylpenem-3-carboxylic acid antibiotics
KR870000324B1 (ko)	1987-02-27	디브로모페니실란산 및 그의 유도체의 탈브롬화방법
NO842248L (no)	1984-12-07	Fremgangsmaate for fremstilling av 6-aminometyl-penicillansyre-1,1-dioksyd-derivater
CH648850A5 (de)	1985-04-15	Penicillansaeure-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel.
DK166883B1 (da)	1993-07-26	Analogifremgangsmaade til fremstilling af 6-aminoalkylpenicillansyre-1,1-dioxider samt derivater eller salte deraf
US5321020A (en)	1994-06-14	Antibacterial 2-carbapenem derivatives
US4588527A (en)	1986-05-13	Process for preparing penicillanic acid 1,1-dioxide derivatives
EP0128718B1 (en)	1986-12-30	Process for 6-(aminomethyl)penicillanic acid 1,1-dioxide and derivatives thereof
NO842249L (no)	1984-12-07	Fremgangsmaate for fremstilling av 6-(aminometyl)penicillansyre-1,1-dioksyd-estere
US5506225A (en)	1996-04-09	Antibacterial penem compounds
CA1270814A (en)	1990-06-26	6-(1-acyl-1-hydroxymethyl)penicillanic acid derivatives
AU616345B2 (en)	1991-10-24	Antibacterial 2-carbapenem derivatives
NO832871L (no)	1983-06-23	Fremgangsmaate for fremstilling av penicillansyrederivater som er egnet som utgangsmateriale ved fremstilling av antibakterielle penicillinderivater
US4505905A (en)	1985-03-19	Cyclobutanone antibacterials
US4169833A (en)	1979-10-02	Novel phosphorane intermediates for use in preparing penem antibiotics
NO844091L (no)	1985-04-15	Fremgangsmaate for fremstilling av 2-dioksacykloalkyltio-2-penem-3-karboksylsyre-derivater
JPH05117280A (ja)	1993-05-14	アミノ酸置換チアゼトキノリン−３−カルボン酸誘導体
US4554160A (en)	1985-11-19	Penicillin esters, salts thereof and methods for their preparation
NO172390B (no)	1993-04-05	Analogifremgangsmaate for stereospesifikk fremstilling av terapeutisk aktive furo(3,4-c)-pyridin-enantiomerer
NO167382B (no)	1991-07-22	Analogifremgangsmaate for fremstilling av terapeutisk aktive 4-hydroxy-4-(substituerte alkenyl)cyklohexancarboxylsyrer.