BE881862A - Composes antibacteriens et inhibiteurs de beta-lactamase, procede pour les preparer et leur usage comme medicaments - Google Patents

Composes antibacteriens et inhibiteurs de beta-lactamase, procede pour les preparer et leur usage comme medicaments Download PDF

Info

Publication number: BE881862A
Authority: BE; Belgium
Prior art keywords: emi; general formula; compound; group; formula
Prior art date: 1979-02-24

Application number

BE0/199502A

Other languages

English (en)

French (fr)

Inventor

M Foglio

G Franceschi

C Scarafile

F Arcamome

A Sanfilippo

Original Assignee

Erba Farmitalia

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.)

1979-02-24

Filing date

1980-02-22

Publication date

1980-08-22

1980-02-22 Application filed by Erba Farmitalia filed Critical Erba Farmitalia

1980-08-22 Publication of BE881862A publication Critical patent/BE881862A/fr

Links

150000001875 compounds Chemical class 0.000 title claims description 88
238000000034 method Methods 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 4
239000003814 drug Substances 0.000 title description 3
230000000844 anti-bacterial effect Effects 0.000 title description 2
239000003781 beta lactamase inhibitor Substances 0.000 title 1
229940126813 beta-lactamase inhibitor Drugs 0.000 title 1
-1 benzyloxycarbonyloxy Chemical group 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 11
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
230000004913 activation Effects 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
238000001727 in vivo Methods 0.000 claims description 4
230000002503 metabolic effect Effects 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
238000006467 substitution reaction Methods 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
238000006385 ozonation reaction Methods 0.000 claims 4
USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
238000006317 isomerization reaction Methods 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
125000005633 phthalidyl group Chemical group 0.000 claims 1
238000007363 ring formation reaction Methods 0.000 claims 1
239000000243 solution Substances 0.000 description 28
239000000203 mixture Substances 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
238000001704 evaporation Methods 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
230000008020 evaporation Effects 0.000 description 16
239000000741 silica gel Substances 0.000 description 16
229910002027 silica gel Inorganic materials 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 8
238000003756 stirring Methods 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 7
125000002768 hydroxyalkyl group Chemical group 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 6
239000003480 eluent Substances 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
239000007832 Na2SO4 Substances 0.000 description 4
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
238000005949 ozonolysis reaction Methods 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
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 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000005055 short column chromatography Methods 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
229930186147 Cephalosporin Natural products 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 2
DIOVBHTUHUUROP-UHFFFAOYSA-N acetyloxymethyl 2-oxoacetate Chemical compound CC(=O)OCOC(=O)C=O DIOVBHTUHUUROP-UHFFFAOYSA-N 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
238000010586 diagram Methods 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
125000005843 halogen group Chemical group 0.000 description 2
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
150000002960 penicillins Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
CJZSHVMLIFESHD-UHFFFAOYSA-O (3-amino-4-oxo-1-sulfanylpyridin-2-yl)oxycarbonylazanium Chemical compound NC(=O)OC1=C(N)C(O)=CC=[N+]1S CJZSHVMLIFESHD-UHFFFAOYSA-O 0.000 description 1
HVRMNEPIBIGCNZ-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-oxoacetate Chemical compound [O-][N+](=O)C1=CC=C(COC(=O)C=O)C=C1 HVRMNEPIBIGCNZ-UHFFFAOYSA-N 0.000 description 1
ARAIIFFPXFUMGY-AATRIKPKSA-N (E)-4-[(4-nitrophenyl)methoxy]-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 ARAIIFFPXFUMGY-AATRIKPKSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
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 1
229910020667 PBr3 Inorganic materials 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012455 biphasic mixture Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
DJANLSNABDFZLA-RQJHMYQMSA-N methyl (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound S1C(C)(C)[C@H](C(=O)OC)N2C(=O)C[C@H]21 DJANLSNABDFZLA-RQJHMYQMSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 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
238000007911 parenteral administration Methods 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
108700026220 vif Genes Proteins 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)

BE0/199502A 1979-02-24 1980-02-22 Composes antibacteriens et inhibiteurs de beta-lactamase, procede pour les preparer et leur usage comme medicaments BE881862A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7906634		1979-02-24

Publications (1)

Publication Number	Publication Date
BE881862A true BE881862A (fr)	1980-08-22

Family

ID=10503424

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/199502A BE881862A (fr)	1979-02-24	1980-02-22	Composes antibacteriens et inhibiteurs de beta-lactamase, procede pour les preparer et leur usage comme medicaments

Country Status (4)

Country	Link
JP (1)	JPS55136288A (xx)
KR (1)	KR840000865B1 (xx)
BE (1)	BE881862A (xx)
ZA (1)	ZA80993B (xx)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4577016A (en) *	1982-04-08	1986-03-18	Farmitalia Carlo Erba S.P.A.	Process for the preparation of penem derivatives

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5625110A (en) *	1978-12-18	1981-03-10	Bristol Myers Co	Antibacterial
GB8300295D0 (en) *	1983-01-06	1983-02-09	Erba Farmitalia	Penem esters
GB8416651D0 (en) *	1984-06-29	1984-08-01	Erba Farmitalia	Penem derivatives
DE69329939T2 (de)	1992-04-28	2001-06-28	Tanabe Seiyaku Co	Verfahrenzur Abspaltung von Silylschutzgruppen aus geschützten HO-Gruppen
EP0966471B1 (en)	1997-12-29	2002-06-12	Research Corporation Technologies, Inc	2-beta-substituted-6-alkylidene penicillanic acid derivatives as beta-lactamase inhibitors
US6407091B1 (en)	1999-04-15	2002-06-18	Research Corporation Technologies, Inc.	β-lactamase inhibiting compounds
JP2005502687A (ja)	2001-07-24	2005-01-27	アラムクスエルエルシー	β−ラクタマーゼ阻害剤としての７−アルキリデン−３−置換型−３−セフェム−４−カルボキシラート
JP2005525399A (ja)	2002-04-04	2005-08-25	アラムクスエルエルシー	セリンおよびメタロ−β−ラクタマーゼの阻害剤

1980
- 1980-02-21 ZA ZA00800993A patent/ZA80993B/xx unknown
- 1980-02-22 BE BE0/199502A patent/BE881862A/fr not_active IP Right Cessation
- 1980-02-23 JP JP2108080A patent/JPS55136288A/ja active Granted
- 1980-02-25 KR KR1019800000767A patent/KR840000865B1/ko active

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4577016A (en) *	1982-04-08	1986-03-18	Farmitalia Carlo Erba S.P.A.	Process for the preparation of penem derivatives
US4729990A (en) *	1982-04-08	1988-03-08	Farmitalia Carlo Erba S.P.A.	Substituted penem derivatives

Also Published As

Publication number	Publication date
JPS55136288A (en)	1980-10-23
JPH03396B2 (xx)	1991-01-07
KR840000865B1 (ko)	1984-06-20
ZA80993B (en)	1981-02-25
KR830001945A (ko)	1983-05-19

Legal Events

Date

Code

Title

Description

1997-08-31

RE

Patent lapsed

Owner name: FARMITALIA CARLO ERBA S.R.L.

Effective date: 19970228

Publication	Publication Date	Title
EP0430771B1 (fr)	1994-07-20	Dérivés de l'isoindolone, leur préparation et leur utilisation comme intermédiaires pour la préparation d'antagonistes de la substance P
FR2676446A1 (fr)	1992-11-20	Nouveaux derives du thiopyranopyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent.
FR2689888A1 (fr)	1993-10-15	Nouveaux dérivés de pérhydroisoindole, leur préparation et les compositions pharmaceutiques qui les contiennent.
FR2676443A1 (fr)	1992-11-20	Nouveaux derives de perhydroisoindole et leur preparation.
LU82192A1 (fr)	1980-06-06	Composes antibacteriens et inhibituers de beta-lactamase, procede pour les preparer et leur usage comme medicaments
BE881862A (fr)	1980-08-22	Composes antibacteriens et inhibiteurs de beta-lactamase, procede pour les preparer et leur usage comme medicaments
LU82795A1 (fr)	1981-04-17	Composes penam acetoxymethyles et composition pharmaceutique les contenant
EP0635002B1 (fr)	1998-07-22	Nouveaux derives de perhydroisoindole, et leur preparation
FR2518098A1 (fr)	1983-06-17	Procede pour la preparation de derives penem optiquement actifs
BE875053A (fr)	1979-07-16	Composes analogues aux cephalosporines
LU82215A1 (fr)	1980-09-24	Procede et composes intermediaires pour la prouduction du 1,1-dioxyde d'acide penicillanique et de ses esters
EP0658557A1 (fr)	1995-06-21	Nouveaux analogues de l'éburnane, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
EP0119896B1 (fr)	1986-10-08	Nouveaux dérivés de l'amino-5 dithiole-1,2 one-3, leur préparation et les compositions médicinales qui les contiennent
BE887886A (fr)	1981-09-10	Derivés de l'acide 2-peneme-3-carboxylique leur preparation et leur application thérapeutique.
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
FR2519002A1 (fr)	1983-07-01	Nouveaux composes bicycliques et procede pour les preparer
BE889151A (fr)	1981-12-09	Derives d'acides peneme-3-carboxylique, leurs procedes de preparation et leur application en therapeutique
FR2483925A1 (fr)	1981-12-11	Procede de preparation de derives de l'acide peneme-3-carboxylique
BE876466A (fr)	1979-11-23	Derive de l'acide penicillanique et son procede de preparation
FR2482966A1 (fr)	1981-11-27	1, 2, 3, 4, 4a, 9b, -hexahydro 4-amino dibenzofurannes, leur procede de preparation et leur application en therapeutique
FR2472569A1 (fr)	1981-07-03	1,2,3,4,4a,9b-hexahydro 4-hydroxy dibenzofurannes et leur procede de preparation
CH635103A5 (fr)	1983-03-15	Derives de penicilline.
EP0188150A1 (fr)	1986-07-23	Procédé de préparation d'isomères optiques de thiazolo [3,2-a] pyrimidines, les nouveaux isomères ainsi obtenus, les compositions pharmaceutiques qui les contiennent et les intermédiaires pour mettre en oeuvre ce procédé
EP0384844A2 (fr)	1990-08-29	Nouveaux dérivés de la 1-arylsulfonyl pyrrollidin-2-thione ou de la 1-aryl-sulfonyl pipéridin-2-thione, leur procédé de préparation, leur application comme médicaments et les compositions les renfermant
EP0187631A1 (fr)	1986-07-16	Procédé pour la préparation de dérivés de pyrrolo-pyridine et nouveaux dérivés obtenus