CH619957A5 - Process for the preparation of derivatives of 7-aminocephalosporic acid. - Google Patents

Process for the preparation of derivatives of 7-aminocephalosporic acid. Download PDF

Info

Publication number: CH619957A5
Authority: CH; Switzerland
Prior art keywords: formula; radical; compound; atom; methyl
Prior art date: 1975-02-22

Application number

CH211176A

Other languages

German (de)

English (en)

Inventor

Peter Hubert Bentley

Gerald Brooks

Original Assignee

Beecham Group Ltd

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.)

1975-02-22

Filing date

1976-02-20

Publication date

1980-10-31

1976-02-20 Application filed by Beecham Group Ltd filed Critical Beecham Group Ltd

1980-10-31 Publication of CH619957A5 publication Critical patent/CH619957A5/de

Links

238000000034 method Methods 0.000 title claims description 30
230000008569 process Effects 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 7
239000002253 acid Substances 0.000 title description 8
-1 2-thienylacetamido, phenylacetamido Chemical group 0.000 claims description 58
150000001875 compounds Chemical class 0.000 claims description 34
230000032050 esterification Effects 0.000 claims description 18
238000005886 esterification reaction Methods 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000003277 amino group Chemical group 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
150000002596 lactones Chemical class 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
KLYCPFXDDDMZNQ-UHFFFAOYSA-N Benzyne Chemical group C1=CC#CC=C1 KLYCPFXDDDMZNQ-UHFFFAOYSA-N 0.000 claims 2
OROGUZVNAFJPHA-UHFFFAOYSA-N 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one Chemical compound CC1SC(=O)C(C)=C1O OROGUZVNAFJPHA-UHFFFAOYSA-N 0.000 claims 1
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
150000003254 radicals Chemical class 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 9
101150065749 Churc1 gene Proteins 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
239000000047 product Substances 0.000 description 7
159000000000 sodium salts Chemical class 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
BXRVAIYLQLSKIJ-UHFFFAOYSA-N 3-iodo-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(I)OC(=O)C2=C1 BXRVAIYLQLSKIJ-UHFFFAOYSA-N 0.000 description 4
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
229950004030 cefaloglycin Drugs 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000005457 ice water Substances 0.000 description 4
229930186147 Cephalosporin Natural products 0.000 description 3
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 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
150000005840 aryl radicals Chemical class 0.000 description 3
229940124587 cephalosporin Drugs 0.000 description 3
239000012043 crude product Substances 0.000 description 3
230000005012 migration Effects 0.000 description 3
238000013508 migration Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
125000005633 phthalidyl group Chemical group 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
239000011734 sodium Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
CLMSHAWYULIVFQ-UHFFFAOYSA-N 3-bromo-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(Br)OC(=O)C2=C1 CLMSHAWYULIVFQ-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
230000000694 effects Effects 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
230000000269 nucleophilic effect Effects 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 description 1
SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical compound S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 description 1
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 1
125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 1
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-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
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
230000010933 acylation Effects 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
230000008901 benefit Effects 0.000 description 1
150000001555 benzenes 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
238000009835 boiling Methods 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 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
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002081 enamines Chemical group 0.000 description 1
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
125000001624 naphthyl group Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000012048 reactive intermediate Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
239000012991 xanthate Substances 0.000 description 1

Classifications

- 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
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- 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
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
- 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
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)

CH211176A 1975-02-22 1976-02-20 Process for the preparation of derivatives of 7-aminocephalosporic acid. CH619957A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7546/75A GB1544404A (en)	1975-02-22	1975-02-22	Process for preparing esters of 7-amino-cephalosporanic acid derivatives

Publications (1)

Publication Number	Publication Date
CH619957A5 true CH619957A5 (en)	1980-10-31

Family

ID=9835213

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH211176A CH619957A5 (en)	1975-02-22	1976-02-20	Process for the preparation of derivatives of 7-aminocephalosporic acid.

Country Status (18)

Country	Link
JP (1)	JPS51101995A (da)
AR (1)	AR212809A1 (da)
AT (1)	AT345456B (da)
AU (1)	AU505037B2 (da)
BE (1)	BE838514A (da)
CA (1)	CA1071621A (da)
CH (1)	CH619957A5 (da)
DE (1)	DE2605159A1 (da)
DK (1)	DK72976A (da)
ES (1)	ES445009A1 (da)
FI (1)	FI760292A7 (da)
FR (1)	FR2301527A1 (da)
GB (1)	GB1544404A (da)
IE (1)	IE42404B1 (da)
NL (1)	NL7601662A (da)
NO (1)	NO760577L (da)
SE (1)	SE7601534L (da)
ZA (1)	ZA76441B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3139534A (en) *	1960-06-17	1964-06-30	Honeywell Regulator Co	Pulse characterizing apparatus using saturable core means to effect pulse delay and shaping

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1377661A (en) *	1971-06-05	1974-12-18	Yamanouchi Pharma Co Ltd	Oxofuryl ester derivatives of penicillin and cephalosporin
GB1406113A (en) *	1972-10-05	1975-09-17	Leo Pharm Prod Ltd	Process for the preparation of cephalosporin estets

1975
- 1975-02-22 GB GB7546/75A patent/GB1544404A/en not_active Expired
1976
- 1976-01-19 IE IE100/76A patent/IE42404B1/en unknown
- 1976-01-26 ZA ZA441A patent/ZA76441B/xx unknown
- 1976-01-30 CA CA244,626A patent/CA1071621A/en not_active Expired
- 1976-02-04 AR AR262151A patent/AR212809A1/es active
- 1976-02-06 FI FI760292A patent/FI760292A7/fi not_active Application Discontinuation
- 1976-02-07 JP JP51012737A patent/JPS51101995A/ja active Pending
- 1976-02-09 ES ES445009A patent/ES445009A1/es not_active Expired
- 1976-02-10 DE DE19762605159 patent/DE2605159A1/de not_active Withdrawn
- 1976-02-11 FR FR7603744A patent/FR2301527A1/fr active Granted
- 1976-02-11 SE SE7601534A patent/SE7601534L/ not_active Application Discontinuation
- 1976-02-12 BE BE164288A patent/BE838514A/xx unknown
- 1976-02-19 NL NL7601662A patent/NL7601662A/xx not_active Application Discontinuation
- 1976-02-19 AT AT118476A patent/AT345456B/de not_active IP Right Cessation
- 1976-02-20 NO NO760577A patent/NO760577L/no unknown
- 1976-02-20 CH CH211176A patent/CH619957A5/de not_active IP Right Cessation
- 1976-02-20 DK DK72976*#A patent/DK72976A/da not_active Application Discontinuation
- 1976-02-23 AU AU11339/76A patent/AU505037B2/en not_active Expired

Also Published As

Publication number	Publication date
FI760292A7 (da)	1976-08-23
IE42404B1 (en)	1980-07-30
IE42404L (en)	1976-08-22
NO760577L (da)	1976-08-24
ATA118476A (de)	1978-01-15
SE7601534L (sv)	1976-08-23
FR2301527B1 (da)	1980-03-07
AU505037B2 (en)	1979-11-08
AT345456B (de)	1978-09-25
AU1133976A (en)	1977-09-01
CA1071621A (en)	1980-02-12
NL7601662A (nl)	1976-08-24
BE838514A (fr)	1976-08-12
ES445009A1 (es)	1977-08-16
DE2605159A1 (de)	1976-09-02
ZA76441B (en)	1977-01-26
DK72976A (da)	1976-08-23
GB1544404A (en)	1979-04-19
AR212809A1 (es)	1978-10-13
JPS51101995A (da)	1976-09-08
FR2301527A1 (fr)	1976-09-17

Legal Events

Date	Code	Title	Description
1985-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH624119A5 (da)	1981-07-15
DE1670625A1 (de)	1970-08-06	7-alpha-Aminobenzyl-3-methylcephalosporinanaloge und ihre Herstellung
DE2461526C2 (de)	1984-11-22	N-Acylderivate von &alpha;-Aminobenzylpenicillinen
DE2263861A1 (de)	1973-07-05	Verfahren zur herstellung von 7acylamido-3-cephem-4-carbonsaeure
DE2324272A1 (de)	1973-11-29	3-methylencephalosporine
DE2514020A1 (de)	1975-10-02	Acylureidocephalosporine
DE1670324B2 (de)	1977-03-10	7-cyanacetylamino-cephalosporansaeurederivate
DE2735732A1 (de)	1978-02-16	Cephalosporinester
DE2428139A1 (de)	1975-01-09	Cephalosporine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
DE2521063A1 (de)	1975-11-27	Phenylacetamidocephalosporin- derivate
DE3035259C2 (de)	1986-03-13	Cephalosporinverbindungen, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten
DE2234280B2 (de)	1979-03-29	Cephalosporinverbindungen und Verfahren zu deren Herstellung
DE2534926A1 (de)	1976-02-19	Sauerstoffanaloge von cephalosporinen
DE2233499A1 (de)	1973-02-01	Cephalosporinderivate und verfahren zu deren herstellung
CH623825A5 (da)	1981-06-30
DE2303022A1 (de)	1973-08-09	Verfahren zur herstellung von cephalosporinen mit einem primaeren 3-carbamoyloxymethylsubstituenten
DE2605159A1 (de)	1976-09-02	Verfahren zur herstellung von 7-aminocephalosporansaeure und deren derivate
DE2550151A1 (de)	1976-05-26	Neue cephalosporine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
CH625805A5 (da)	1981-10-15
DE2519742A1 (de)	1975-12-04	Cephalosporinester
DE2350230C2 (de)	1984-01-19	Verfahren zur Herstellung von Cephalosporinestern
CH623589A5 (en)	1981-06-15	Process for the preparation of cephalosporin esters
CH627471A5 (en)	1982-01-15	Process for the preparation of cephalosporin compounds
DE2722666C2 (de)	1982-04-15	7-Acylamino-3-pyrazinylthiomethyl- 3-cephem-4-carbonsäure-Verbindungen und ihre Verwendung/Bekämpfung bakterieller Infektionen
AT255646B (de)	1967-07-10	Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure