CA1158639A - Acide 6-bromopenicillanique sulfone - Google Patents

Acide 6-bromopenicillanique sulfone

Info

Publication number: CA1158639A
Authority: CA; Canada
Prior art keywords: acid; bromo; thia; oxo; dimethyl
Prior art date: 1978-12-11
Legal status (The legal status 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 status listed.): Expired

Application number

CA000339594A

Other languages

English (en)

Inventor

Eric M. Gordon

William H. Koster

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ER Squibb and Sons LLC

Original Assignee

ER Squibb and Sons LLC

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.)

1978-12-11

Filing date

1979-11-09

Publication date

1983-12-13

1978-12-11 Priority claimed from US05/968,538 external-priority patent/US4203992A/en

1978-12-11 Priority claimed from US05/968,539 external-priority patent/US4203993A/en

1979-11-09 Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC

1983-12-13 Application granted granted Critical

1983-12-13 Publication of CA1158639A publication Critical patent/CA1158639A/fr

Status Expired legal-status Critical Current

Links

PRRXJFSPPODDDK-ALEPSDHESA-N (2s,5r,6r)-6-bromo-3,3-dimethyl-4,4,7-trioxo-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)N2C(=O)[C@@H](Br)[C@H]21 PRRXJFSPPODDDK-ALEPSDHESA-N 0.000 title abstract description 3
150000002148 esters Chemical class 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 11
DAVPSCAAXXVSFU-RVJQKOHUSA-N (2s,5r,6s)-6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2[C@@H](Br)C(=O)N21 DAVPSCAAXXVSFU-RVJQKOHUSA-N 0.000 claims abstract description 5
-1 benzhydryl ester Chemical class 0.000 claims description 29
239000002253 acid Substances 0.000 claims description 23
150000001875 compounds Chemical class 0.000 claims description 13
238000000034 method Methods 0.000 claims description 10
239000003960 organic solvent Substances 0.000 claims description 8
230000001590 oxidative effect Effects 0.000 claims description 7
NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 claims description 6
ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000003638 chemical reducing agent Substances 0.000 claims description 3
102000004190 Enzymes Human genes 0.000 abstract description 20
108090000790 Enzymes Proteins 0.000 abstract description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
239000000203 mixture Substances 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
230000003115 biocidal effect Effects 0.000 description 11
239000000243 solution Substances 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
230000015556 catabolic process Effects 0.000 description 7
238000006731 degradation reaction Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
241000894006 Bacteria Species 0.000 description 5
239000003782 beta lactam antibiotic agent Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 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
159000000000 sodium salts Chemical class 0.000 description 4
229930182555 Penicillin Natural products 0.000 description 3
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 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
150000003951 lactams Chemical class 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 2
229960000723 ampicillin Drugs 0.000 description 2
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 2
238000013459 approach Methods 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
150000002960 penicillins Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 2
JETQIUPBHQNHNZ-NJBDSQKTSA-N (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[[(2r)-2-phenyl-2-sulfoacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H](C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)S(O)(=O)=O)=CC=CC=C1 JETQIUPBHQNHNZ-NJBDSQKTSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 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
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 1
DNHPKCHVSYFMCQ-UHFFFAOYSA-N 7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound OC(=O)C1CSC2CC(=O)N12 DNHPKCHVSYFMCQ-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
241000588652 Neisseria gonorrhoeae Species 0.000 description 1
229930195708 Penicillin V Natural products 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
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 1
229960003022 amoxicillin Drugs 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
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 1
229960003669 carbenicillin Drugs 0.000 description 1
CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 1
229960003866 cefaloridine Drugs 0.000 description 1
229960000603 cefalotin Drugs 0.000 description 1
VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
229940125532 enzyme inhibitor Drugs 0.000 description 1
239000002532 enzyme inhibitor Substances 0.000 description 1
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
239000000463 material Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
229940056367 penicillin v Drugs 0.000 description 1
BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
239000013612 plasmid Substances 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
229960001841 potassium permanganate Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000009877 rendering Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229960004932 sulbenicillin Drugs 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000001665 trituration 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CA000339594A 1978-12-11 1979-11-09 Acide 6-bromopenicillanique sulfone Expired CA1158639A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US968,539		1978-12-11
US05/968,538 US4203992A (en)	1978-12-11	1978-12-11	β-Bromopenicillanic acid sulfone
US05/968,539 US4203993A (en)	1978-12-11	1978-12-11	6α-Bromopenicillanic acid sulfone
US968,538		1978-12-11

Publications (1)

Publication Number	Publication Date
CA1158639A true CA1158639A (fr)	1983-12-13

Family

ID=27130513

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000339594A Expired CA1158639A (fr)	1978-12-11	1979-11-09	Acide 6-bromopenicillanique sulfone

Country Status (5)

Country	Link
CA (1)	CA1158639A (fr)
DE (1)	DE2949809A1 (fr)
FR (1)	FR2444040A1 (fr)
GB (2)	GB2037759B (fr)
IT (1)	IT1164843B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4397783A (en) *	1979-03-05	1983-08-09	Pfizer Inc.	Process for converting 6,6-disubstituted penicillanic acid derivatives to the 6-β-congeners
SE449103B (sv) *	1979-03-05	1987-04-06	Pfizer	Sett att framstella penicillansyra-1,1-dioxid samt estrar derav
IE49768B1 (en)	1979-05-21	1985-12-11	Leo Pharm Prod Ltd	6beta-halopenicillanic acid derivatives
GB8522156D0 (en) *	1985-09-06	1985-10-09	Leo Pharm Prod Ltd	Producing chemical compounds

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IN149747B (fr) *	1977-06-07	1982-04-03	Pfizer
DE2912511C2 (de) *	1977-06-07	1982-06-24	Pfizer Inc., 10017 New York, N.Y.	Pharmazeutische Zusammensetzung, enthaltend Penicillansäure

1979
- 1979-11-09 CA CA000339594A patent/CA1158639A/fr not_active Expired
- 1979-11-30 IT IT50964/79A patent/IT1164843B/it active
- 1979-12-05 GB GB7941987A patent/GB2037759B/en not_active Expired
- 1979-12-11 FR FR7930383A patent/FR2444040A1/fr active Granted
- 1979-12-11 DE DE19792949809 patent/DE2949809A1/de not_active Ceased
1982
- 1982-06-28 GB GB08218692A patent/GB2115406B/en not_active Expired

Also Published As

Publication number	Publication date
FR2444040A1 (fr)	1980-07-11
GB2115406A (en)	1983-09-07
GB2037759A (en)	1980-07-16
IT7950964A0 (it)	1979-11-30
DE2949809A1 (de)	1980-06-19
IT1164843B (it)	1987-04-15
GB2115406B (en)	1984-03-21
GB2037759B (en)	1983-04-13
FR2444040B1 (fr)	1983-03-25

Legal Events

Date	Code	Title	Description
2000-12-13	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20001213

Publication	Publication Date	Title
CA1060432A (fr)	1979-08-14	DERIVES DE LA 7 .alpha. METOXYCEPHALOSPORINE
CA1325077C (fr)	1993-12-07	Derives du beta-lactam
US4203992A (en)	1980-05-20	β-Bromopenicillanic acid sulfone
GB1576796A (en)	1980-10-15	Thiadiazolyl cephalosporin analogues
EP0005889A1 (fr)	1979-12-12	Procédé de préparation de dérivés de bêta-lactame, les nouveaux dérivés ainsi obtenus et compositions pharmaceutiques les contenant
US4276285A (en)	1981-06-30	Combinations of penicillanic acid 1,1-dioxide with 7-(D-2-[4-ethylpiperazin-2,3-dione-1-carboxamido]-2-[4-hydroxyphenyl]acetamido)-3-([1-methyl-5-tetrazolyl]thiomethyl)-3-desacetoxymethylcephalosporanic acid
US4672114A (en)	1987-06-09	Process for the preparation of pure 6-β-halopenicillanic acids and salts thereof
EP0061313B1 (fr)	1985-01-16	Bis-esters de 1,1-alcane-diols avec le 1,1-dioxyde de l'acide 6-béta-hydroxy-méthylpénicillanique et les antibiotiques bêta-lactames
CA1158639A (fr)	1983-12-13	Acide 6-bromopenicillanique sulfone
US4256733A (en)	1981-03-17	Acetoxymethyl penam compounds as β-lactamase inhibitors
KR920005829B1 (ko)	1992-07-20	2β-치환된 티오메틸페니실린 유도체 및 그의 염의 제조방법
EP0025857B1 (fr)	1983-07-27	Sulfoxydes organiques ayant un groupe latent allyle, leur préparation et composition pharmaceutique antibactérienne les contenant
US4420426A (en)	1983-12-13	6-Alpha-halopenicillanic acid 1,1-dioxides
EP0000645B1 (fr)	1981-01-28	Isopénicillines, procédés pour leur préparation et compositions qui les contiennent
US4241050A (en)	1980-12-23	Penam 1,1-dioxides as beta-lactamase inhibitors
CA1154011A (fr)	1983-09-20	ACIDES 6-.beta.-SUBSTITUANT PENICILLANIQUES, INHIBITEURS DE LA .beta.-LACTAMASE
US4260598A (en)	1981-04-07	Method for increasing antibacterial effectiveness of a β-lactam antibiotic
US4247548A (en)	1981-01-27	7α-Methoxycephalosporin derivatives and their pharmaceutical compositions having antibacterial activity
US4203993A (en)	1980-05-20	6α-Bromopenicillanic acid sulfone
US4154845A (en)	1979-05-15	Derivatives of 6-aminopenicillanic acid
SE449103B (sv)	1987-04-06	Sett att framstella penicillansyra-1,1-dioxid samt estrar derav
US3968109A (en)	1976-07-06	Production of 2-(thio substituted)cephalosporin sulfoxides and 2-(thio substituted)cephalosporins
US4342758A (en)	1982-08-03	Allylsulfoxide enzyme inhibitors
GB2105329A (en)	1983-03-23	Penem-3-carboxylic acid derivatives their preparation and their use as antimicrobial agents
US3928336A (en)	1975-12-23	7-{8 D-({60 -amino{60 -phenyl-, 2-thienyl- and 3-thienyl-acetamido){9 -3-(3-methyl-1,2,5-oxadiazol-4-yl)carbonylthiomethyl-3-cephem-4-carboxylic acids