CA1053681A - Derives antibacteriens de l'azetidinone - Google Patents

Derives antibacteriens de l'azetidinone

Info

Publication number: CA1053681A
Authority: CA; Canada
Prior art keywords: formula; group; iii; compound; pharmaceutically acceptable
Prior art date: 1974-10-22
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

CA237,296A

Other languages

English (en)

Other versions

CA237296S (en

Inventor

Thomas T. Howarth

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.)

Beecham Group PLC

Original Assignee

Beecham Group PLC

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.)

1974-10-22

Filing date

1975-10-08

Publication date

1979-05-01

1975-10-08 Application filed by Beecham Group PLC filed Critical Beecham Group PLC

1979-05-01 Application granted granted Critical

1979-05-01 Publication of CA1053681A publication Critical patent/CA1053681A/fr

Status Expired legal-status Critical Current

Links

230000000844 anti-bacterial effect Effects 0.000 title 1
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 75
238000000034 method Methods 0.000 claims abstract description 45
150000003839 salts Chemical class 0.000 claims abstract description 42
150000002148 esters Chemical class 0.000 claims abstract description 29
238000002360 preparation method Methods 0.000 claims abstract description 20
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
125000002252 acyl group Chemical group 0.000 claims abstract description 16
238000005917 acylation reaction Methods 0.000 claims abstract description 8
230000010933 acylation Effects 0.000 claims abstract description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
-1 sulphonyloxy Chemical group 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 12
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
238000009833 condensation Methods 0.000 claims description 7
230000005494 condensation Effects 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
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 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
230000001737 promoting effect Effects 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
150000001718 carbodiimides Chemical class 0.000 claims description 4
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 4
150000004702 methyl esters Chemical class 0.000 claims description 4
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 4
125000003944 tolyl group Chemical group 0.000 claims description 4
NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 claims description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
239000011575 calcium Substances 0.000 claims description 3
229910052791 calcium Inorganic materials 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
AZUFHGGGPUUXKI-FLFDDASRSA-N benzyl (2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound O=C([C@@H]1N2C(=O)C[C@H]2O\C1=C/CO)OCC1=CC=CC=C1 AZUFHGGGPUUXKI-FLFDDASRSA-N 0.000 claims description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000005545 phthalimidyl group Chemical group 0.000 claims description 2
125000002577 pseudohalo group Chemical group 0.000 claims description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 2
125000004001 thioalkyl group Chemical group 0.000 claims description 2
239000000126 substance Substances 0.000 claims 15
239000000376 reactant Substances 0.000 claims 6
229940090805 clavulanate Drugs 0.000 claims 2
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims 2
159000000003 magnesium salts Chemical class 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
101150047265 COR2 gene Proteins 0.000 claims 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims 1
101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
BCDXFOKEDLUDKA-UHFFFAOYSA-M sodium 3-(2-acetyloxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound C(C)(=O)OCC=C1C(N2C(CC2O1)=O)C(=O)[O-].[Na+] BCDXFOKEDLUDKA-UHFFFAOYSA-M 0.000 claims 1
229930186147 Cephalosporin Natural products 0.000 abstract description 5
229930182555 Penicillin Natural products 0.000 abstract description 5
229940124587 cephalosporin Drugs 0.000 abstract description 5
150000001780 cephalosporins Chemical class 0.000 abstract description 5
150000002960 penicillins Chemical class 0.000 abstract description 5
230000002401 inhibitory effect Effects 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 3
125000004442 acylamino group Chemical group 0.000 abstract description 2
239000003112 inhibitor Substances 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 6
239000000243 solution Substances 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
230000000994 depressogenic effect Effects 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
239000000463 material Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
241000588724 Escherichia coli Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000007429 general method Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 2
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000063 preceeding effect Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
241000786363 Rhampholeon spectrum Species 0.000 description 1
101100054666 Streptomyces halstedii sch3 gene Proteins 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
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 1
229960000723 ampicillin Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229960003324 clavulanic acid Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
125000000962 organic group Chemical group 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
229910052763 palladium Inorganic materials 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; 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)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Cephalosporin Compounds (AREA)

CA237,296A 1974-10-22 1975-10-08 Derives antibacteriens de l'azetidinone Expired CA1053681A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB45738/74A GB1529434A (en)	1974-10-22	1974-10-22	Acyl derivatives of clavulanic acid methods for their preparation and compositions containing them

Publications (1)

Publication Number	Publication Date
CA1053681A true CA1053681A (fr)	1979-05-01

Family

ID=10438383

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA237,296A Expired CA1053681A (fr)	1974-10-22	1975-10-08	Derives antibacteriens de l'azetidinone

Country Status (15)

Country	Link
JP (1)	JPS5165794A (fr)
AU (1)	AU497089B2 (fr)
BE (1)	BE834645A (fr)
CA (1)	CA1053681A (fr)
CH (1)	CH623822A5 (fr)
DE (1)	DE2546243A1 (fr)
DK (1)	DK473875A (fr)
ES (1)	ES441965A1 (fr)
FR (1)	FR2288520A1 (fr)
GB (1)	GB1529434A (fr)
IE (1)	IE41808B1 (fr)
IL (1)	IL48265A (fr)
NL (1)	NL7512348A (fr)
SE (1)	SE428563B (fr)
ZA (1)	ZA756473B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7711640A (nl) *	1976-10-25	1978-04-27	Glaxo Lab Ltd	Werkwijze voor de bereiding van nieuwe clavamderivaten.
US4647457A (en) *	1983-12-16	1987-03-03	Hoffmann-La Roche Inc.	Penicillanic acid derivatives

1974
- 1974-10-22 GB GB45738/74A patent/GB1529434A/en not_active Expired
1975
- 1975-10-07 IL IL48265A patent/IL48265A/xx unknown
- 1975-10-08 IE IE2200/75A patent/IE41808B1/en unknown
- 1975-10-08 CA CA237,296A patent/CA1053681A/fr not_active Expired
- 1975-10-14 ZA ZA00756473A patent/ZA756473B/xx unknown
- 1975-10-15 DE DE19752546243 patent/DE2546243A1/de not_active Withdrawn
- 1975-10-17 FR FR7531781A patent/FR2288520A1/fr active Granted
- 1975-10-17 SE SE7511693A patent/SE428563B/xx unknown
- 1975-10-17 BE BE161057A patent/BE834645A/fr not_active IP Right Cessation
- 1975-10-20 JP JP50126835A patent/JPS5165794A/ja active Pending
- 1975-10-21 ES ES441965A patent/ES441965A1/es not_active Expired
- 1975-10-21 AU AU85909/75A patent/AU497089B2/en not_active Expired
- 1975-10-21 DK DK473875A patent/DK473875A/da unknown
- 1975-10-21 NL NL7512348A patent/NL7512348A/xx not_active Application Discontinuation
- 1975-10-22 CH CH1368875A patent/CH623822A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
IE41808B1 (en)	1980-03-26
IL48265A0 (en)	1975-12-31
ES441965A1 (es)	1977-08-01
IE41808L (en)	1976-04-22
SE7511693L (sv)	1976-04-23
CH623822A5 (en)	1981-06-30
DK473875A (da)	1976-04-23
IL48265A (en)	1979-01-31
AU8590975A (en)	1977-05-05
BE834645A (fr)	1976-04-20
ZA756473B (en)	1976-09-29
SE428563B (sv)	1983-07-11
NL7512348A (nl)	1976-04-26
JPS5165794A (fr)	1976-06-07
DE2546243A1 (de)	1976-05-06
FR2288520A1 (fr)	1976-05-21
FR2288520B1 (fr)	1978-11-10
GB1529434A (en)	1978-10-18
AU497089B2 (en)	1978-11-30

Publication	Publication Date	Title
US4201782A (en)	1980-05-06	Thiadiazolyl cephalosporin analogs
JPS5946956B2 (ja)	1984-11-15	抗生物質の新規な中間体の製造方法
US4122262A (en)	1978-10-24	Intermediates and methods for preparing 7-acylamino-8-oxo-oxa-1-azabicyclo[4.2.0]octane-2-carboxylic acid derivatives
US4244965A (en)	1981-01-13	Azetidinoyl ethers
SU959628A3 (ru)	1982-09-15	Способ получени 1,1-диоксидов 2-ацетоксиметил-2-метилпенам-3-карбоновой кислоты или ее солей с щелочными металлами
CA1053681A (fr)	1979-05-01	Derives antibacteriens de l'azetidinone
US4215128A (en)	1980-07-29	Clavulanic acid derivatives their preparation and use
KR900005046B1 (ko)	1990-07-18	페니실린 유도체의 제조방법
US4166816A (en)	1979-09-04	Methods and intermediates for preparing cis-4-oxoazetidine intermediates
AU623932B2 (en)	1992-05-28	Stable oxapenem-3-carboxylic acids and their use as b-lactamase inhibitors
US4048186A (en)	1977-09-13	Antibacterial substituted azetidinones
US4079177A (en)	1978-03-14	Clavulanic acid carbamates
US4072674A (en)	1978-02-07	Cis-4-oxoazetidine intermediates and methods of preparing them
Webber et al.	1975	Chemistry of cephalosporin antibiotics. 28. Preparation and biological activity of 3-(substituted) vinyl cephalosporins
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