LU81795A1 - Nouvelle penicilline semi-synthetique,son procede de production et composition pharmaceutique la contenant - Google Patents

Nouvelle penicilline semi-synthetique,son procede de production et composition pharmaceutique la contenant Download PDF

Info

Publication number: LU81795A1
Authority: LU; Luxembourg
Prior art keywords: acid; ester; salt; formula; product
Prior art date: 1978-10-16

Application number

LU81795A

Other languages

English (en)

French (fr)

Original Assignee

Bristol Myers 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.)

1978-10-16

Filing date

1979-10-16

Publication date

1980-05-07

1979-10-16 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1980-05-07 Publication of LU81795A1 publication Critical patent/LU81795A1/fr

Links

238000000034 method Methods 0.000 title claims description 27
230000008569 process Effects 0.000 title claims description 16
239000008194 pharmaceutical composition Substances 0.000 title claims description 6
229930182555 Penicillin Natural products 0.000 title description 23
229940049954 penicillin Drugs 0.000 title description 16
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 title description 14
239000002253 acid Substances 0.000 claims description 49
150000002148 esters Chemical class 0.000 claims description 48
150000003839 salts Chemical class 0.000 claims description 43
-1 pivaloyloxymethyl Chemical group 0.000 claims description 39
239000000047 product Substances 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 20
239000003795 chemical substances by application Substances 0.000 claims description 11
230000000844 anti-bacterial effect Effects 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 7
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 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000005633 phthalidyl group Chemical group 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
125000006239 protecting group Chemical class 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 1
238000007911 parenteral administration Methods 0.000 claims 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
239000000203 mixture Substances 0.000 description 30
239000000243 solution Substances 0.000 description 24
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 11
150000002960 penicillins Chemical class 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
229960002292 piperacillin Drugs 0.000 description 10
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 10
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
230000010933 acylation Effects 0.000 description 8
238000005917 acylation reaction Methods 0.000 description 8
229960004821 amikacin Drugs 0.000 description 8
230000000694 effects Effects 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000000284 extract Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
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 6
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
238000002211 ultraviolet spectrum Methods 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
239000003242 anti bacterial agent Substances 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
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238000001914 filtration Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000002844 melting Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
229920001817 Agar Polymers 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000008272 agar Substances 0.000 description 4
230000003115 biocidal effect Effects 0.000 description 4
FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 4
229960003669 carbenicillin Drugs 0.000 description 4
XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 4
229960000603 cefalotin Drugs 0.000 description 4
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 4
230000006870 function Effects 0.000 description 4
239000000499 gel Substances 0.000 description 4
238000007918 intramuscular administration Methods 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 4
JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
229930186147 Cephalosporin Natural products 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
241000589516 Pseudomonas Species 0.000 description 3
229940126575 aminoglycoside Drugs 0.000 description 3
229940126574 aminoglycoside antibiotic Drugs 0.000 description 3
239000002647 aminoglycoside antibiotic agent Substances 0.000 description 3
230000036765 blood level Effects 0.000 description 3
229940124587 cephalosporin Drugs 0.000 description 3
150000001780 cephalosporins Chemical class 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000010828 elution Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
244000005700 microbiome Species 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
230000002195 synergetic effect Effects 0.000 description 3
CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical compound C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-N 0.000 description 2
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241000894006 Bacteria Species 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000588697 Enterobacter cloacae Species 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
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150000001408 amides Chemical class 0.000 description 2
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PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
230000002301 combined effect Effects 0.000 description 2
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230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
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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 description 2
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JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 1
SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
SRVFFFJZQVENJC-IHRRRGAJSA-N aloxistatin Chemical compound CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C SRVFFFJZQVENJC-IHRRRGAJSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
229960001656 amikacin sulfate Drugs 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
230000003385 bacteriostatic effect Effects 0.000 description 1
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
239000012964 benzotriazole Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
230000007073 chemical hydrolysis Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 1
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940092559 enterobacter aerogenes Drugs 0.000 description 1
230000007071 enzymatic hydrolysis Effects 0.000 description 1
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
101150064711 fliO gene Proteins 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000005417 image-selected in vivo spectroscopy Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000007689 inspection Methods 0.000 description 1
238000012739 integrated shape imaging system Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229960000318 kanamycin Drugs 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
231100000417 nephrotoxicity Toxicity 0.000 description 1
230000007694 nephrotoxicity Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000008520 organization Effects 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
231100000262 ototoxicity Toxicity 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
210000003899 penis Anatomy 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000004262 preparative liquid chromatography Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000029305 taxis Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
230000009466 transformation Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
230000035899 viability Effects 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)

LU81795A 1978-10-16 1979-10-16 Nouvelle penicilline semi-synthetique,son procede de production et composition pharmaceutique la contenant LU81795A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US95190078A	1978-10-16	1978-10-16
US95190078		1978-10-16
US96733878		1978-12-07
US05/967,338 US4206116A (en)	1978-10-16	1978-12-07	Novel penicillins

Publications (1)

Publication Number	Publication Date
LU81795A1 true LU81795A1 (fr)	1980-05-07

Family

ID=27130320

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU81795A LU81795A1 (fr)	1978-10-16	1979-10-16	Nouvelle penicilline semi-synthetique,son procede de production et composition pharmaceutique la contenant

Country Status (18)

Country	Link
US (1)	US4206116A (es)
AT (1)	AT366385B (es)
AU (1)	AU533598B2 (es)
CA (1)	CA1132540A (es)
CH (1)	CH644383A5 (es)
DE (1)	DE2941717A1 (es)
DK (1)	DK435279A (es)
ES (1)	ES485079A0 (es)
FI (1)	FI68839C (es)
FR (1)	FR2439202A1 (es)
GB (1)	GB2043627B (es)
GR (1)	GR72291B (es)
IE (1)	IE49083B1 (es)
IT (1)	IT1206996B (es)
LU (1)	LU81795A1 (es)
NL (1)	NL7907577A (es)
SE (2)	SE445456B (es)
YU (3)	YU41888B (es)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3215085A1 (de) *	1982-04-22	1983-10-27	Bayer Ag, 5090 Leverkusen	Ss-lactam-antibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
EP0093564B1 (en) *	1982-04-29	1987-06-24	Beecham Group Plc	Beta-lactam antibiotics
DE3479731D1 (en) *	1983-07-07	1989-10-19	Beecham Group Plc	Substituted phenylglycine derivatives of beta-lactam antibiotics

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1450764A (en) *	1972-09-14	1976-09-29	Beecham Group Ltd	Penicillins
US4110327A (en) *	1974-05-09	1978-08-29	Toyama Chemical Co., Ltd.	2,3 Diketo-piperazinocarbonylamino alkanoic acids and derivatives
US4087424A (en) *	1974-05-09	1978-05-02	Toyama Chemical Co., Ltd.	Novel penicillins and cephalosporins and process for producing the same

1978
- 1978-12-07 US US05/967,338 patent/US4206116A/en not_active Expired - Lifetime
1979
- 1979-10-02 CA CA336,802A patent/CA1132540A/en not_active Expired
- 1979-10-04 GR GR60185A patent/GR72291B/el unknown
- 1979-10-05 AU AU51499/79A patent/AU533598B2/en not_active Ceased
- 1979-10-08 YU YU2437/79A patent/YU41888B/xx unknown
- 1979-10-09 GB GB7934995A patent/GB2043627B/en not_active Expired
- 1979-10-11 FR FR7925346A patent/FR2439202A1/fr active Granted
- 1979-10-11 FI FI793169A patent/FI68839C/fi not_active IP Right Cessation
- 1979-10-12 NL NL7907577A patent/NL7907577A/nl not_active Application Discontinuation
- 1979-10-15 DE DE19792941717 patent/DE2941717A1/de not_active Withdrawn
- 1979-10-15 DK DK435279A patent/DK435279A/da not_active Application Discontinuation
- 1979-10-15 CH CH927379A patent/CH644383A5/fr not_active IP Right Cessation
- 1979-10-15 IT IT7950565A patent/IT1206996B/it active
- 1979-10-15 SE SE7908528A patent/SE445456B/sv unknown
- 1979-10-15 IE IE1952/79A patent/IE49083B1/en unknown
- 1979-10-16 AT AT0673579A patent/AT366385B/de active
- 1979-10-16 LU LU81795A patent/LU81795A1/fr unknown
- 1979-10-16 ES ES485079A patent/ES485079A0/es active Granted
1982
- 1982-10-04 YU YU2227/82A patent/YU42051B/xx unknown
- 1982-10-04 YU YU02226/82A patent/YU222682A/xx unknown
1984
- 1984-09-11 SE SE8404556A patent/SE8404556L/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
IE49083B1 (en)	1985-07-24
FR2439202A1 (fr)	1980-05-16
ATA673579A (de)	1981-08-15
US4206116A (en)	1980-06-03
FI793169A7 (fi)	1980-04-17
SE7908528L (sv)	1980-04-17
YU222682A (en)	1983-04-30
YU243779A (en)	1983-01-21
GB2043627B (en)	1982-10-06
SE8404556D0 (sv)	1984-09-11
GB2043627A (en)	1980-10-08
CH644383A5 (fr)	1984-07-31
AU5149979A (en)	1980-04-24
ES8101076A1 (es)	1980-12-01
IT1206996B (it)	1989-05-17
CA1132540A (en)	1982-09-28
SE445456B (sv)	1986-06-23
SE8404556L (sv)	1984-09-11
NL7907577A (nl)	1980-04-18
FR2439202B1 (es)	1983-02-11
IE791952L (en)	1980-04-16
ES485079A0 (es)	1980-12-01
DK435279A (da)	1980-04-17
YU42051B (en)	1988-04-30
GR72291B (es)	1983-10-17
IT7950565A0 (it)	1979-10-15
AU533598B2 (en)	1983-12-01
FI68839B (fi)	1985-07-31
AT366385B (de)	1982-04-13
DE2941717A1 (de)	1980-04-24
YU222782A (en)	1983-04-30
FI68839C (fi)	1985-11-11
YU41888B (en)	1988-02-29

Publication	Publication Date	Title
LU79774A1 (fr)	1980-01-22	Procede de preparation de 1,1-dioxydes de l'acide penicillanique et de ses esters utiles comme inhibiteurs de la b-lactamase
LU82452A1 (fr)	1980-12-16	Bis-esters de methanediol avec des penicillines et le 1,1-dioxyde d'acide penicillanique,leur procede de production et composition pharmaceutique les contenant
EP0034536A2 (fr)	1981-08-26	Nouvelles oximes dérivées de l'acide 3-alkyloxy ou 3-alkylthiométhyl 7-amino thiazolylacétamido céphalosporanique, leur préparation, leur application comme médicaments et les compositions les renfermant
CH638221A5 (fr)	1983-09-15	Oximes derivees de l'acide 3-substitue 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et les compositions pharmaceutiques les renfermant.
CA1094547A (fr)	1981-01-27	Procede de preparation de derives de l'acide 3- carbamoyloxymethyl 7-(amino thiazolyl acetamido) cephalosporanique
CA1148937A (fr)	1983-06-28	Procede de preparation de nouvelles aco-yloximes substituees derivees de l'acide 7-(2-amino 4-thiazolyl) acetamido cephalosporanique
FR2465736A1 (fr)	1981-03-27	Composes penam acetoxymethyles et composition pharmaceutique les contenant
LU82215A1 (fr)	1980-09-24	Procede et composes intermediaires pour la prouduction du 1,1-dioxyde d'acide penicillanique et de ses esters
BE846094A (fr)	1977-03-10	Nouvelles penicillines et leurs procedes de preparation
LU81795A1 (fr)	1980-05-07	Nouvelle penicilline semi-synthetique,son procede de production et composition pharmaceutique la contenant
BE875054A (fr)	1979-07-16	Composes analogues aux cephalosporines
LU82219A1 (fr)	1980-09-24	Acides penicillamiques 6- -substitues inhibiteurs de -lac-tamase, leur procede de production et composition pharmaceutique les contenant
EP0080944B1 (fr)	1985-08-28	Nouveaux dérivés de céphalosporines substitués en position 3 par un groupe hétérocycle thiométhyl, procédé de préparation desdits composés et compositions pharmaceutiques en contenant
FR2468608A1 (fr)	1981-05-08	Derives de la 1-oxadethiacephalosporine, leur procede de production et compositions anti-bacteriennes les contenant
BE1007544A3 (fr)	1995-08-01	Derives de thioalkylthiocarbacephalosporines.
BE887886A (fr)	1981-09-10	Derivés de l'acide 2-peneme-3-carboxylique leur preparation et leur application thérapeutique.
FR2551441A1 (fr)	1985-03-08	Derives de aminomethyl-2-penem, leur procede de preparation et les preparations pharmaceutiques
CH640858A5 (fr)	1984-01-31	Oximes derivees de l'acide 3-azidomethyl 7-amino thiazolyl acetamido cephalosporanique, leurs procedes de preparation et les medicaments les renfermant.
FR2482103A1 (fr)	1981-11-13	Sulfone d'acide 2b-chloromethyl-2a-methylpename-3a-carboxylique, son procede de preparation et son utilisation en association avec des antibiotiques de la classe des b-lactamines
CA1140113A (fr)	1983-01-25	Procede de preparation de nouvelles oximes 0-substituees par un radical comportant un ammonium quatermaire et derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique
BE879443A (fr)	1980-04-16	Nouvelle penicilline semi-synthetique, son procede de production et composition pharmaceutique la contenant
CH415636A (fr)	1966-06-30	Procédé de préparation de nouvelles pénicillines
BE897183A (fr)	1983-10-17	Esters carboxyliques aisement clivables et leur utilisation dans la synthese de penems et autres antibiotiques de beta -lactame
BE852213R (fr)	1977-09-08	Nouvelles cephalosporines et leur preparation
FR2520362A1 (fr)	1983-07-29	Nouveaux composes de type b-lactame, y compris leurs sels formes avec des acides ou des bases acceptables en pharmacie, procedes pour produire ces composes, medicaments les contenant et leur utilisation pour combattre les maladies infectieuses