CH654831A5 - Azetidinverbindungen. - Google Patents

Azetidinverbindungen. Download PDF

Info

Publication number: CH654831A5
Authority: CH; Switzerland
Prior art keywords: azetidin; compound; methyl; cooch; formula
Prior art date: 1979-02-24

Application number

CH2794/84A

Other languages

German (de)

English (en)

Inventor

Maurizio Foglio

Giovanni Franceschi

Cosimo Scarafile

Federico Arcamone

Aurora-Sanfilippo Grein

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

1980-02-21

Publication date

1986-03-14

1980-02-21 Application filed by Erba Farmitalia filed Critical Erba Farmitalia

1986-03-14 Publication of CH654831A5 publication Critical patent/CH654831A5/de

Links

150000001875 compounds Chemical class 0.000 description 56
-1 cyclic radical Chemical class 0.000 description 29
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
125000000217 alkyl group Chemical group 0.000 description 14
239000000203 mixture Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 11
239000001257 hydrogen Substances 0.000 description 11
125000004435 hydrogen atom Chemical class [H]* 0.000 description 11
238000001704 evaporation Methods 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000002768 hydroxyalkyl group Chemical group 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
239000002904 solvent Substances 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 6
238000000034 method Methods 0.000 description 6
239000007832 Na2SO4 Substances 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
125000000753 cycloalkyl group Chemical group 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
150000002148 esters Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000002198 insoluble material Substances 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
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 2
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 2
125000006519 CCH3 Chemical group 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
229910020667 PBr3 Inorganic materials 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
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
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-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
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
108090000204 Dipeptidase 1 Proteins 0.000 description 1
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
150000000475 acetylene derivatives Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001539 azetidines Chemical class 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
102000006635 beta-lactamase Human genes 0.000 description 1
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical class Cl* 0.000 description 1
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 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
238000001035 drying Methods 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000007429 general method Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000004519 manufacturing process Methods 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
239000012074 organic phase 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
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
150000003952 β-lactams Chemical class 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
- 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
- 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
- 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)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Cephalosporin Compounds (AREA)

CH2794/84A 1979-02-24 1980-02-21 Azetidinverbindungen. CH654831A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7906634		1979-02-24
GB7932591		1979-09-20

Publications (1)

Publication Number	Publication Date
CH654831A5 true CH654831A5 (de)	1986-03-14

Family

ID=26270697

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH2794/84A CH654831A5 (de)	1979-02-24	1980-02-21	Azetidinverbindungen.
CH1400/80A CH651570A5 (de)	1979-02-24	1980-02-21	Antibakterielle penemverbindungen mit beta-lactamase-aktivitaet und verfahren zu deren herstellung.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1400/80A CH651570A5 (de)	1979-02-24	1980-02-21	Antibakterielle penemverbindungen mit beta-lactamase-aktivitaet und verfahren zu deren herstellung.

Country Status (24)

Country	Link
AT (1)	AT368506B (fr)
AU (1)	AU535080B2 (fr)
CA (2)	CA1154010A (fr)
CH (2)	CH654831A5 (fr)
CS (1)	CS226010B2 (fr)
DE (1)	DE3006273A1 (fr)
DK (1)	DK159448C (fr)
ES (2)	ES488886A0 (fr)
FI (1)	FI75163C (fr)
FR (1)	FR2449690B1 (fr)
GB (1)	GB2043639B (fr)
GR (1)	GR73623B (fr)
HK (1)	HK74487A (fr)
HU (1)	HU182664B (fr)
IE (1)	IE49407B1 (fr)
IT (1)	IT1193922B (fr)
LU (1)	LU82192A1 (fr)
NL (1)	NL192265C (fr)
NO (1)	NO161000C (fr)
NZ (1)	NZ192949A (fr)
PT (1)	PT70849A (fr)
SE (1)	SE449489B (fr)
UA (1)	UA6041A1 (fr)
YU (1)	YU42964B (fr)

Families Citing this family (23)

* 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
DE3121510A1 (de) *	1980-07-04	1982-06-16	Farmitalia Carlo Erba S.p.A., 20159 Milano	6-alkyl-2-subst.-peneme und verfahren zu ihrer herstellung
JPS588084A (ja) *	1981-07-08	1983-01-18	Takeda Chem Ind Ltd	（６ｒ）−置換−（５ｒ）−ペネム−３−カルボン酸誘導体およびその製造法
AU8605382A (en) *	1981-07-15	1983-01-20	Sumitomo Chemical Company, Limited	Penicillins and azetidinones
AT379399B (de) *	1981-12-11	1985-12-27	Erba Farmitalia	Verfahren zur herstellung von optisch aktiven penemen
NO831160L (no) *	1982-04-08	1983-10-10	Erba Farmitalia	Fremstilling av substituerte penem-derivater
PH21930A (en) *	1982-11-16	1988-04-08	Ciba Geigy Ag	6-hydroxy-lower alkylpenem compounds,pharmaceutical composition containing same and method of use thereof
DE3372968D1 (en) *	1982-11-16	1987-09-17	Ciba Geigy Ag	Heterocyclyl-thio compounds, process for their preparation, pharmaceutical compositions containing them and their use
GB8300295D0 (en) *	1983-01-06	1983-02-09	Erba Farmitalia	Penem esters
JPS59152387A (ja) *	1983-02-10	1984-08-31	Shionogi & Co Ltd	新規ペネム化合物
GB8321677D0 (en) *	1983-08-11	1983-09-14	Erba Farmitalia	Preparation of penems
US4656165A (en) *	1983-09-02	1987-04-07	Ciba-Geigy Corporation	Aminomethyl penem compounds
US4711886A (en) *	1984-07-02	1987-12-08	Merck & Co., Inc.	β-lactam derivatives as anti-inflammatory and antidegenerative agents
US4761408A (en) *	1984-11-02	1988-08-02	Ciba-Geigy Corporation	Crystalline aminomethyl compound
ES2058328T3 (es) *	1987-02-11	1994-11-01	Ciba Geigy Ag	Acidos beta-lactama carboxilicos biciclicos.
GB2206578B (en) *	1987-07-07	1991-07-03	Erba Carlo Spa	Process for the preparation of penems
US5364768A (en) *	1987-07-07	1994-11-15	Farmitalia Carlo Erba S.R.L.	Process for the preparation of penems
IT1286558B1 (it) *	1996-02-27	1998-07-15	Menarini Farma Ind	Processo per la preparazione di 2-alogenometil-penems e loro uso per la preparazione di penems antibatterici
ATE219085T1 (de)	1997-12-29	2002-06-15	Res Corp Technologies Inc	2-beta-substituierte-6-alkylidenpenizillansäure derivate als beta-laktamase inhibitoren
US6407091B1 (en)	1999-04-15	2002-06-18	Research Corporation Technologies, Inc.	β-lactamase inhibiting compounds
US6720445B2 (en) *	2000-12-21	2004-04-13	Beacon Laboratories, Inc.	Acetyloxymethyl esters and methods for using the same
CA2454413A1 (fr)	2001-07-24	2003-03-13	Alamx, L.L.C.	7-alkylidene-3-substitues-3-cephem-4-carboxylates utilises en tant qu'inhibiteurs de beta-lactamase
WO2003087105A1 (fr)	2002-04-04	2003-10-23	Alamx, L.L.C.	INHIBITEURS DE SERINE ET DE METALLO-ss-LACTAMASES

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
LU77306A1 (fr) *	1977-05-09	1979-01-18
AU3796278A (en) *	1977-07-13	1980-01-17	Glaxo Group Ltd	Penams and azetidinones
US4168314A (en) *	1977-11-17	1979-09-18	Merck & Co., Inc.	6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid
US4155912A (en) *	1977-12-14	1979-05-22	Bristol-Myers Company	2-Methylpenem-3-carboxylic acid antibiotics
EP0003415A3 (fr) *	1978-01-20	1979-08-22	Glaxo Group Limited	Composés bêta-lactames, procédés pour leur préparation, compositions pharmaceutiques les contenant et les intermédiaires pour leur préparation
EP0042026B1 (fr) *	1978-02-02	1986-01-08	Ciba-Geigy Ag	Dérivés d'azétidin-2-one 3,4-disubstitués et procédé de préparation
EP0010358A1 (fr) *	1978-09-20	1980-04-30	Glaxo Group Limited	Composés de bêta-lactame, procédés pour leur préparation, compositions les contenant, intermédiaires utilisables dans leur préparation et méthodes pour leur production
JPS5625110A (en) *	1978-12-18	1981-03-10	Bristol Myers Co	Antibacterial
EP0013067A1 (fr) *	1978-12-22	1980-07-09	Beecham Group Plc	Agents antibactériens à cycle bêta-lactame bicyclique, leur utilisation dans des compositions pharmaceutiques, procédés pour leur préparation et intermédiaires à utiliser dans de tels procédés

1980
- 1980-02-19 IT IT20021/80A patent/IT1193922B/it active
- 1980-02-19 GR GR61228A patent/GR73623B/el unknown
- 1980-02-19 GB GB8005476A patent/GB2043639B/en not_active Expired
- 1980-02-19 FI FI800493A patent/FI75163C/fi not_active IP Right Cessation
- 1980-02-19 AU AU55670/80A patent/AU535080B2/en not_active Ceased
- 1980-02-19 AT AT0091980A patent/AT368506B/de not_active IP Right Cessation
- 1980-02-19 NL NL8001012A patent/NL192265C/nl not_active IP Right Cessation
- 1980-02-20 DE DE19803006273 patent/DE3006273A1/de active Granted
- 1980-02-20 PT PT70849A patent/PT70849A/pt not_active IP Right Cessation
- 1980-02-20 YU YU461/80A patent/YU42964B/xx unknown
- 1980-02-20 CA CA000346011A patent/CA1154010A/fr not_active Expired
- 1980-02-20 IE IE338/80A patent/IE49407B1/en not_active IP Right Cessation
- 1980-02-21 CH CH2794/84A patent/CH654831A5/de not_active IP Right Cessation
- 1980-02-21 CH CH1400/80A patent/CH651570A5/de not_active IP Right Cessation
- 1980-02-22 LU LU82192A patent/LU82192A1/fr unknown
- 1980-02-22 SE SE8001424A patent/SE449489B/sv not_active IP Right Cessation
- 1980-02-22 NZ NZ192949A patent/NZ192949A/en unknown
- 1980-02-22 FR FR8003938A patent/FR2449690B1/fr not_active Expired
- 1980-02-22 DK DK077580A patent/DK159448C/da not_active IP Right Cessation
- 1980-02-22 NO NO800501A patent/NO161000C/no unknown
- 1980-02-22 CS CS801241A patent/CS226010B2/cs unknown
- 1980-02-22 HU HU80420A patent/HU182664B/hu not_active IP Right Cessation
- 1980-02-22 UA UA2886007A patent/UA6041A1/uk unknown
- 1980-02-23 ES ES488886A patent/ES488886A0/es active Granted
- 1980-10-16 ES ES495977A patent/ES8107224A1/es not_active Expired
1986
- 1986-01-14 CA CA000499579A patent/CA1212665B/fr not_active Expired
1987
- 1987-10-15 HK HK744/87A patent/HK74487A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT1193922B (it)	1988-08-31
CA1212665B (fr)	1986-10-14
DK159448C (da)	1991-03-04
YU46180A (en)	1983-02-28
GB2043639A (en)	1980-10-08
HU182664B (en)	1984-02-28
NL192265C (nl)	1997-04-03
NL8001012A (nl)	1980-08-26
DE3006273A1 (de)	1980-09-04
NO161000B (no)	1989-03-13
FI75163B (fi)	1988-01-29
YU42964B (en)	1989-02-28
HK74487A (en)	1987-10-23
IE49407B1 (en)	1985-10-02
CA1154010A (fr)	1983-09-20
IT8020021A1 (it)	1981-08-19
ES8200685A1 (es)	1981-11-16
ES495977A0 (es)	1981-10-01
DK77580A (da)	1980-08-25
IE800338L (en)	1980-08-24
LU82192A1 (fr)	1980-06-06
FI800493A7 (fi)	1980-08-25
ATA91980A (de)	1982-02-15
NO800501L (no)	1980-08-25
AT368506B (de)	1982-10-25
FI75163C (fi)	1988-05-09
ES488886A0 (es)	1981-11-16
IT8020021A0 (it)	1980-02-19
SE449489B (sv)	1987-05-04
DK159448B (da)	1990-10-15
NO161000C (no)	1989-06-21
PT70849A (en)	1980-03-01
AU5567080A (en)	1980-09-11
FR2449690A1 (fr)	1980-09-19
NZ192949A (en)	1984-03-16
GR73623B (fr)	1984-03-26
SE8001424L (sv)	1980-08-25
FR2449690B1 (fr)	1986-06-13
ES8107224A1 (es)	1981-10-01
AU535080B2 (en)	1984-03-01
UA6041A1 (uk)	1994-12-29
CH651570A5 (de)	1985-09-30
CS226010B2 (en)	1984-03-19
NL192265B (nl)	1996-12-02
GB2043639B (en)	1983-07-20

Legal Events

Date	Code	Title	Description
1988-05-31	PFA	Name/firm changed	Owner name: FARMITALIA CARLO ERBA S.R.L.
1997-10-15	PL	Patent ceased

Publication	Publication Date	Title
CH654831A5 (de)	1986-03-14	Azetidinverbindungen.
LU82066A1 (de)	1980-08-08	2-penem-verbindungen und verfahren zu ihrer herstellung
CH645902A5 (de)	1984-10-31	Beta-lactam-zwischenverbindungen sowie verfahren zu ihrer herstellung.
CH628901A5 (de)	1982-03-31	Verfahren zur herstellung von cephalosporinantibiotika.
CH663024A5 (de)	1987-11-13	Verfahren zur herstellung von penemderivaten.
DE69032681T2 (de)	1999-02-25	Cephalosporine und ihre Homologen, Verfahren zu ihrer Herstellung und pharmazeutische Präparate
EP0050805B1 (fr)	1985-07-24	Bêta-lactames, intermédiaires et procédé de préparation, ainsi que les compositions pharmaceutiques les contenant
DE3382761T2 (de)	1995-03-09	Verfahren zur Herstellung von Penem-Verbindungen.
CH617677A5 (fr)	1980-06-13
DE3216256C2 (fr)	1989-12-21
CH623331A5 (en)	1981-05-29	Process for the preparation of 7beta-amino- and 7beta-acylamino-6alphaH-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-ca rboxylic acid derivatives
DE3008257C2 (de)	1984-03-01	Verfahren zur Herstellung von Penicillansäure-1,1-dioxid und dessen Estern
KR840000865B1 (ko)	1984-06-20	β-락탐-함유 항균제의 제조방법
CH630333A5 (de)	1982-06-15	Verfahren zur spaltung von benzylestern von carbonsaeuren.
DE2534926C2 (de)	1982-12-30	Verfahren zur Herstellung von Estern der 7-Oxo- und 7&beta;-Hydroxy-cephalosporansäure und deren 3-substituierten Derivaten
DE2952413C2 (de)	1986-12-11	3-Halogencarbacephem-Verbindungen und Verfahren zu ihrer Herstellung
EP0185221B1 (fr)	1990-09-26	Procédé pour la préparation de dérivés d'aminothiazolylacide acétique
DE2429166A1 (de)	1975-01-09	Verfahren zur selektiven spaltung der amidsaeurefunktion eines 7-(amidsaeure)cephalosporins
DD202163A5 (de)	1983-08-31	Verfahren und zwischenstufen zur herstellung von 1,1-dixopenicillanoyloxymethyl-6 (2-amino-2-phenylacetamido)penicillanaten
DE69024114T2 (de)	1996-05-09	Verfahren zur Herstellung von Penemen
EP0101602B1 (fr)	1988-06-01	Dérivés de oxo-7-oxa-4-diazabicyclo-(3.2.0)-hept-en-2 non substitués en position 6, procédés pour leur préparation et leur utilisation comme produits intermédiaires pour la synthèse d'antibiotiques béta-lactames
EP0221846A1 (fr)	1987-05-13	Acyloxyazétidinones optiquement actives
DE3914658A1 (de)	1989-11-16	Chemisches verfahren
CH650262A5 (de)	1985-07-15	6-alpha- und 6-beta-substituierte penicillansaeurederivate und verfahren zu ihrer herstellung.
EP0023887A2 (fr)	1981-02-11	Dérivés d'azétidinone bicycliques substitués en 3, procédé pour leur préparation et intermédiaires ainsi que leur préparation