NO760577L - - Google Patents

Info

Publication number: NO760577L
Authority: NO; Norway
Prior art keywords: group; formula; stated; methyl; compound
Prior art date: 1975-02-22

Application number

NO760577A

Other languages

English (en)

Norwegian (no)

Inventor

P H Bentley

G 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

1976-08-24

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

1976-08-24 Publication of NO760577L publication Critical patent/NO760577L/no

Links

238000000034 method Methods 0.000 claims description 28
150000001875 compounds Chemical class 0.000 claims description 24
-1 carbamoyloxy Chemical group 0.000 claims description 18
238000005886 esterification reaction Methods 0.000 claims description 18
230000032050 esterification Effects 0.000 claims description 15
125000003277 amino group Chemical group 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
125000004442 acylamino group Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
239000012038 nucleophile Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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 description 2
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 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
150000002596 lactones Chemical class 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 2
125000001424 substituent group Chemical group 0.000 claims 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
230000007306 turnover Effects 0.000 claims 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
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 9
239000011734 sodium Substances 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
239000000243 solution Substances 0.000 description 9
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
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
125000005633 phthalidyl group Chemical group 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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
229930186147 Cephalosporin Natural products 0.000 description 4
229940124587 cephalosporin Drugs 0.000 description 4
239000005457 ice water Substances 0.000 description 4
230000005012 migration Effects 0.000 description 4
238000013508 migration Methods 0.000 description 4
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 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
238000005917 acylation reaction Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229950004030 cefaloglycin Drugs 0.000 description 3
150000001780 cephalosporins Chemical class 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
125000001544 thienyl group Chemical group 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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 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
125000002252 acyl group Chemical group 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
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 2
229960000603 cefalotin Drugs 0.000 description 2
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 2
239000012043 crude product Substances 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
239000012535 impurity Substances 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
238000001556 precipitation Methods 0.000 description 2
125000004076 pyridyl group Chemical group 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
125000003831 tetrazolyl group Chemical group 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
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
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 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
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 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
230000008901 benefit Effects 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
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
150000007942 carboxylates 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
125000002843 carboxylic acid group Chemical group 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 description 1
238000010511 deprotection reaction Methods 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
125000001240 enamine group Chemical group 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 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
150000002497 iodine compounds Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
125000001624 naphthyl group Chemical group 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
239000003208 petroleum Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003222 pyridines Chemical class 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
235000009518 sodium iodide Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003536 tetrazoles Chemical class 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
238000001665 trituration Methods 0.000 description 1
238000010626 work up procedure Methods 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)

NO760577A 1975-02-22 1976-02-20 NO760577L (ru)

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
NO760577L true NO760577L (ru)	1976-08-24

Family

ID=9835213

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO760577A NO760577L (ru)	1975-02-22	1976-02-20

Country Status (18)

Country	Link
JP (1)	JPS51101995A (ru)
AR (1)	AR212809A1 (ru)
AT (1)	AT345456B (ru)
AU (1)	AU505037B2 (ru)
BE (1)	BE838514A (ru)
CA (1)	CA1071621A (ru)
CH (1)	CH619957A5 (ru)
DE (1)	DE2605159A1 (ru)
DK (1)	DK72976A (ru)
ES (1)	ES445009A1 (ru)
FI (1)	FI760292A (ru)
FR (1)	FR2301527A1 (ru)
GB (1)	GB1544404A (ru)
IE (1)	IE42404B1 (ru)
NL (1)	NL7601662A (ru)
NO (1)	NO760577L (ru)
SE (1)	SE7601534L (ru)
ZA (1)	ZA76441B (ru)

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/FI760292A/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 AT AT118476A patent/AT345456B/de not_active IP Right Cessation
- 1976-02-19 NL NL7601662A patent/NL7601662A/xx not_active Application Discontinuation
- 1976-02-20 DK DK72976*#A patent/DK72976A/da not_active Application Discontinuation
- 1976-02-20 CH CH211176A patent/CH619957A5/de not_active IP Right Cessation
- 1976-02-20 NO NO760577A patent/NO760577L/no unknown
- 1976-02-23 AU AU11339/76A patent/AU505037B2/en not_active Expired

Also Published As

Publication number	Publication date
BE838514A (fr)	1976-08-12
CH619957A5 (en)	1980-10-31
FR2301527B1 (ru)	1980-03-07
CA1071621A (en)	1980-02-12
AT345456B (de)	1978-09-25
ATA118476A (de)	1978-01-15
SE7601534L (sv)	1976-08-23
AU1133976A (en)	1977-09-01
JPS51101995A (ru)	1976-09-08
ES445009A1 (es)	1977-08-16
NL7601662A (nl)	1976-08-24
DE2605159A1 (de)	1976-09-02
ZA76441B (en)	1977-01-26
IE42404L (en)	1976-08-22
AR212809A1 (es)	1978-10-13
GB1544404A (en)	1979-04-19
AU505037B2 (en)	1979-11-08
FI760292A (ru)	1976-08-23
DK72976A (da)	1976-08-23
IE42404B1 (en)	1980-07-30
FR2301527A1 (fr)	1976-09-17

Publication	Publication Date	Title
KR800001569B1 (ko)	1980-12-28	세팔로스포린 유도체의 제조법
US4504658A (en)	1985-03-12	Epimerization of malonic acid esters
NO145576B (no)	1982-01-11	Analogifremgangsmaate ved fremstilling av terapeutisk aktive penicillinderivater
US3872086A (en)	1975-03-18	Certain disulfide derivatives of 2-azetidinones
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