CH586227A5 - 3-carbamoyloxymethyl-cephalosporins - from carbamoyl halides and alcohols,broad spectrum antibiotics - Google Patents

3-carbamoyloxymethyl-cephalosporins - from carbamoyl halides and alcohols,broad spectrum antibiotics

Info

Publication number: CH586227A5
Authority: CH; Switzerland
Prior art keywords: ester; methoxy; carbamoyloxymethyl; formula; thienylacetamido
Prior art date: 1971-12-14

Application number

CH1813572A

Other languages

German (de)

English (en)

Original Assignee

Merck & Co Inc

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.)

1971-12-14

Filing date

1972-12-13

Publication date

1977-03-31

1972-12-13 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1977-03-31 Publication of CH586227A5 publication Critical patent/CH586227A5/de

Links

-1 carbamoyl halides Chemical class 0.000 title claims abstract description 70
150000001298 alcohols Chemical class 0.000 title abstract description 3
229940124587 cephalosporin Drugs 0.000 title description 13
239000003242 anti bacterial agent Substances 0.000 title description 3
229940088710 antibiotic agent Drugs 0.000 title description 3
125000002252 acyl group Chemical group 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 31
150000002148 esters Chemical class 0.000 claims description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 5
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 claims description 5
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
150000003512 tertiary amines Chemical class 0.000 claims description 4
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 5
HUNBANGPCFCPTB-GCZXYKMCSA-N (6R)-7-methoxy-8-oxo-4-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(=CC=C1)CC(=O)NC1S[C@H]2N(C(=C1)C(=O)O)C(C2OC)=O HUNBANGPCFCPTB-GCZXYKMCSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 3
239000000010 aprotic solvent Substances 0.000 abstract 1
230000000903 blocking effect Effects 0.000 abstract 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 7
229930186147 Cephalosporin Natural products 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
125000000623 heterocyclic group Chemical group 0.000 description 5
150000001780 cephalosporins Chemical class 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000002367 halogens Chemical group 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
108010013043 Acetylesterase Proteins 0.000 description 2
241000207199 Citrus Species 0.000 description 2
102100036617 Monoacylglycerol lipase ABHD2 Human genes 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229940054025 carbamate anxiolytics Drugs 0.000 description 2
150000004657 carbamic acid derivatives Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
235000020971 citrus fruits Nutrition 0.000 description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
244000005700 microbiome Species 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YZKJQBUBQFJLMF-JLOHTSLTSA-N (6r)-3-(carbamoyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C(O)=O)NC(=O)CC1=CC=CS1 YZKJQBUBQFJLMF-JLOHTSLTSA-N 0.000 description 1
IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 1
VTKCZXODCRDHIU-TVKKRMFBSA-N (6r)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@H]2SCC=C(N2C1=O)C(=O)O)NC(=O)CC1=CC=CS1 VTKCZXODCRDHIU-TVKKRMFBSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
241001478240 Coccus Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
YJQPYGGHQPGBLI-UHFFFAOYSA-N Novobiocin Natural products O1C(C)(C)C(OC)C(OC(N)=O)C(O)C1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
BJSRJSIBEOXZBR-ZWAGFTRDSA-N benzhydryl (6r)-3-(hydroxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)CO)C(=O)OC(C=1C=CC=CC=1)C=1C=CC=CC=1)NC(=O)CC1=CC=CS1 BJSRJSIBEOXZBR-ZWAGFTRDSA-N 0.000 description 1
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
229960004484 carbachol Drugs 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
244000000058 gram-negative pathogen Species 0.000 description 1
244000000059 gram-positive pathogen Species 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000002372 labelling Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229960004815 meprobamate Drugs 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
YJQPYGGHQPGBLI-KGSXXDOSSA-N novobiocin Chemical compound O1C(C)(C)[C@H](OC)[C@@H](OC(N)=O)[C@@H](O)[C@@H]1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-KGSXXDOSSA-N 0.000 description 1
229960002950 novobiocin Drugs 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
150000002960 penicillins Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- C07D501/02—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

Landscapes

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

CH1813572A 1971-12-14 1972-12-13 3-carbamoyloxymethyl-cephalosporins - from carbamoyl halides and alcohols,broad spectrum antibiotics CH586227A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US20798371A	1971-12-14	1971-12-14

Publications (1)

Publication Number	Publication Date
CH586227A5 true CH586227A5 (en)	1977-03-31

Family

ID=22772767

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1813572A CH586227A5 (en)	1971-12-14	1972-12-13	3-carbamoyloxymethyl-cephalosporins - from carbamoyl halides and alcohols,broad spectrum antibiotics

Country Status (12)

Country	Link
JP (1)	JPS4867290A (cs)
AT (1)	AT324552B (cs)
CA (1)	CA994326A (cs)
CH (1)	CH586227A5 (cs)
CS (1)	CS178901B2 (cs)
DD (1)	DD101681A5 (cs)
ES (1)	ES409555A1 (cs)
HU (1)	HU165713B (cs)
NL (1)	NL7216137A (cs)
PL (1)	PL79162B1 (cs)
SE (1)	SE400561B (cs)
SU (1)	SU503525A3 (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2639740C2 (de) *	1976-09-03	1985-12-19	8500 Nürnberg HÜWA - Walter Hübner Handelsvertretung	Abstandhalter zum Stützen von Bewehrungen

1972
- 1972-11-27 SE SE1542872A patent/SE400561B/xx unknown
- 1972-11-28 NL NL7216137A patent/NL7216137A/xx not_active Application Discontinuation
- 1972-12-05 PL PL15929972A patent/PL79162B1/pl unknown
- 1972-12-08 CA CA158,812A patent/CA994326A/en not_active Expired
- 1972-12-08 SU SU1855239A patent/SU503525A3/ru active
- 1972-12-12 ES ES409555A patent/ES409555A1/es not_active Expired
- 1972-12-12 AT AT1056572A patent/AT324552B/de not_active IP Right Cessation
- 1972-12-13 DD DD16750772A patent/DD101681A5/xx unknown
- 1972-12-13 JP JP12444572A patent/JPS4867290A/ja active Pending
- 1972-12-13 CS CS857072A patent/CS178901B2/cs unknown
- 1972-12-13 CH CH1813572A patent/CH586227A5/de not_active IP Right Cessation
- 1972-12-14 HU HUME001580 patent/HU165713B/hu unknown

Also Published As

Publication number	Publication date
SU503525A3 (ru)	1976-02-15
CA994326A (en)	1976-08-03
DD101681A5 (cs)	1973-11-12
PL79162B1 (cs)	1975-06-30
ES409555A1 (es)	1976-03-16
NL7216137A (cs)	1973-06-18
CS178901B2 (en)	1977-10-31
AT324552B (de)	1975-09-10
SE400561B (sv)	1978-04-03
HU165713B (cs)	1974-10-28
JPS4867290A (cs)	1973-09-13

Legal Events

Date	Code	Title	Description
1980-08-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2462736C2 (de)	1980-09-11	7-Aminothiazolylacetamido-3-cephem-4-carbonsäuren und Verfahren zur Herstellung derselben
DE2837264C2 (cs)	1991-06-13
DE3249832C2 (cs)	1988-12-29
CH633558A5 (de)	1982-12-15	Verfahren zur herstellung neuer cephalosporinderivate.
DE2539664C2 (cs)	1988-09-29
DE3789720T2 (de)	1994-08-18	Cephalosporinverbindungen.
DE2937868A1 (de)	1980-04-03	7- eckige klammer auf 2-(2-amino- 5-halogen-4-thiazolyl)-2-alkoxyiminoacetamido eckige klammer zu -3-cephem- 4-carbonsaeure-verbindungen, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung bakterieller infektionen
DE2324272A1 (de)	1973-11-29	3-methylencephalosporine
DE2217563A1 (de)	1972-10-26	Verfahren zur Herstellung von Acylaminoverbindungen
DE1953861C2 (de)	1982-12-23	7-Tetrazolylacetamido-3-thiomethyl-3-cephem-4- carbonsäuren
CH626370A5 (en)	1981-11-13	Process for the preparation of the syn isomer or of a mixture of syn and anti isomers of 7beta-acylamidoceph-3-em-4-carboxylic acids with antibiotic activity
DE2203653A1 (de)	1972-08-10	Cephalosporincarbamate und Verfahren zu deren Herstellung
DE2128605A1 (de)	1971-12-23	Neue Cephalosporansäurederivaten und Verfahren zu ihrer Herstellung
DE2715038A1 (de)	1977-11-24	Neue antibakterielle verbindungen
AT365197B (de)	1981-12-28	Verfahren zur herstellung von neuen acylderivaten
EP0029966A2 (de)	1981-06-10	Cephalosporinderivate, und deren Herstellung sowie entsprechende pharmazeutische Präparate
CH654311A5 (de)	1986-02-14	1-oxadethiacephalosporinderivate und verfahren zu deren herstellung.
CH586227A5 (en)	1977-03-31	3-carbamoyloxymethyl-cephalosporins - from carbamoyl halides and alcohols,broad spectrum antibiotics
DE2339045A1 (de)	1974-02-14	Cephalosporinderivate und verfahren zu ihrer herstellung
DE2360620A1 (de)	1974-06-12	Verfahren zur herstellung von lactolartigen cephalosporinen
DE2451492A1 (de)	1975-05-15	2-oxo-1-pyridinyl-penicillin- und -cephalosporin-derivate
EP0553792A2 (de)	1993-08-04	Verfahren zur Herstellung von Ceftriaxon-dinatriumsalzhemiheptahydrat
CH593924A5 (en)	1977-12-30	Cephalosporin carbamates - from alcohols and isocyanates
EP0035161A2 (de)	1981-09-09	Cephalosporine, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
CH576951A5 (en)	1976-06-30	Carbamates prepn - from alcohols and organosilyl isocyanates-esp 3-carbamoyloxy methylcephalosporins