GB1328340A - 3-heterocyclic thiomethylcephalosporins - Google Patents
3-heterocyclic thiomethylcephalosporinsInfo
- Publication number
- GB1328340A GB1328340A GB5838671A GB5838671A GB1328340A GB 1328340 A GB1328340 A GB 1328340A GB 5838671 A GB5838671 A GB 5838671A GB 5838671 A GB5838671 A GB 5838671A GB 1328340 A GB1328340 A GB 1328340A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- alkyl
- alkoxy
- trifluoromethyl
- acid
- Prior art date
- 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
Links
- -1 hydroxy, amino Chemical group 0.000 abstract 10
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 229930186147 Cephalosporin Natural products 0.000 abstract 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 2
- 229940124587 cephalosporin Drugs 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- LGTVLLPQCMJOGT-UHFFFAOYSA-N 2-bromo-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical compound FC(F)(F)C1=NN=C(Br)S1 LGTVLLPQCMJOGT-UHFFFAOYSA-N 0.000 abstract 1
- LTEUXHSAYOSFGQ-UHFFFAOYSA-N 5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=C(C(F)(F)F)S1 LTEUXHSAYOSFGQ-UHFFFAOYSA-N 0.000 abstract 1
- MYBNRTPEGGJIBD-UHFFFAOYSA-N 5-(trifluoromethyl)-3h-1,3,4-thiadiazole-2-thione Chemical compound FC(F)(F)C1=NN=C(S)S1 MYBNRTPEGGJIBD-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 abstract 1
- 230000006181 N-acylation Effects 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Chemical group 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000005336 allyloxy group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 238000006073 displacement reaction Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 230000000269 nucleophilic effect Effects 0.000 abstract 1
- VXVGSHWWCDZYLO-UHFFFAOYSA-N oxan-2-yl 2-hydroxy-2-phenylacetate Chemical compound C=1C=CC=CC=1C(O)C(=O)OC1CCCCO1 VXVGSHWWCDZYLO-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 229960002317 succinimide Drugs 0.000 abstract 1
- 125000003831 tetrazolyl group Chemical group 0.000 abstract 1
- 125000001113 thiadiazolyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1328340 3 - Heterocyclic - thiomethyl cephalosporins SMITH KLINE & FRENCH LABORATORIES 16 Dec 1971 [17 Dec 1970 18 Feb 1971 (2) 17 March 1971] 58386/71 Headings C2A and C2C The invention comprises novel cephalosporins having the Formula (I) wherein A is in which X and X<SP>1</SP> are each hydrogen, hydroxy, amino, halo, nitro, trifluoromethyl, C 1 -C 4 alkyl or C 1 -C 4 alkoxy; M is hydrogen or alkali metal; Y is -NHR or -OR in which R is hydrogen, aminoalkanoyl having up to 6 carbons and in which the alkanoyl group may be straight or branched and may be substituted by hydroxy, mercapto, methylthio, carboxy, amino or phenyl; or R is alkanoyl having up to 8 carbons which may be substituted by C 1 -C 4 alkoxy, carbalkoxy in which the alkoxy group is C 1 -C 4 , hydroxy, allyloxy, C 1 -C 4 alkylthio, azido, halo, azido, cyano, carboxy or phenoxy; or R is carbocyclic acyl optionally substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 2 -C 8 dialkylamino, halo, nitro, trifluoromethyl, hydroxy, amino or cyano; or R is heterocyclic acyl optionally substituted by methyl; and R<SP>1</SP> is a 5- or 6-membered heterocycle containing one or more atoms of N, O and/or S and optionally substituted by one or two of alkyl or alkenyl having up to 4 carbons, cycloalkyl, phenyl, benzyl, alkoxy or alkoxy-alkyl of 1-4 carbons, CF 3 , -SCH 3 , amino, halogen or -NHR<SP>3</SP> or NR<SP>3</SP> 2 in which R<SP>3</SP> is C 1 -C 4 alkyl; wtih the proviso that when R<SP>1</SP> is thiadiazolyl or tetrazolyl or their alkyl substituted derivatives, A is not unsubstituted or mono-substituted phenyl and that when R<SP>1</SP> is methyloxazolyl or methyloxadiazolyl and Y is NH 2 , A is not unsubstituted phenyl. The compounds (I) are prepared by (a) N- acylating an appropriate 7-amino-3-heterocyclic thiomethyl cephalosporanic acid with a carboxyl-activated glycine or glycolic acid; (b) subjecting an appropriate 7-acylamino-3-acetoxymethyl cephalosporanic acid to nucleophilic displacement of the acetoxy group with a mercaptoheterocycle; or (c) subjecting 7- aminocephalosporanic acid to both of reactions (a) and (b). Subsequent treatment to convert compounds wherein Y is NH 2 or OH to compounds wherein Y is NHR or OR and R is other than hydrogen is carried out if necessary, using conventional O- and N-acylation procedures. Labile groups (e.g. NH 2 and OH) in the starting materials are conventionally protected before carrying out procedures (a), (b) or (c) above, the protecting groups being subsequently removed if necessary. Succinimide ester of O-tetrahydropyranylmandelic acid is prepared by reacting the said acid with N-hydroxysuccinimide in the presence of dicyclohexylcarbodiimide. 2 - Amino - 5 - trifluoromethyl - 1,3,4 - thiadiazole is diazotized and then treated with HBr to give 2-bromo-5-trifluoromethyl-1,3,4-thiadiazole, which is reacted with thiourea with subsequent hydrolysis to give 2-mercapto-5-trifluoromethyl-1,3,4-thiadiazole. Pharmaceutical compositions having antibiotic activity comprise a compound of Formula (I) defined hereinbefore together with a pharmaceutically acceptable non-toxic diluent or carrier.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9929670A | 1970-12-17 | 1970-12-17 | |
| US11659871A | 1971-02-18 | 1971-02-18 | |
| US11659971A | 1971-02-18 | 1971-02-18 | |
| US12540371A | 1971-03-17 | 1971-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1328340A true GB1328340A (en) | 1973-08-30 |
Family
ID=27493051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5838671A Expired GB1328340A (en) | 1970-12-17 | 1971-12-16 | 3-heterocyclic thiomethylcephalosporins |
Country Status (17)
| Country | Link |
|---|---|
| AR (1) | AR194216A1 (en) |
| AU (1) | AU459002B2 (en) |
| BE (1) | BE776222A (en) |
| BR (1) | BR7108309D0 (en) |
| CA (1) | CA990281A (en) |
| CH (1) | CH578581A5 (en) |
| DD (1) | DD94997A5 (en) |
| DE (1) | DE2162575A1 (en) |
| FR (1) | FR2118012B1 (en) |
| GB (1) | GB1328340A (en) |
| HU (1) | HU166307B (en) |
| IE (1) | IE35875B1 (en) |
| IL (1) | IL38099A (en) |
| IT (1) | IT1061965B (en) |
| NL (1) | NL7116791A (en) |
| PH (1) | PH9531A (en) |
| RO (1) | RO59318A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3936446A (en) * | 1974-02-19 | 1976-02-03 | Beecham Group Limited | Isocyanocephalosporanates |
| US4605651A (en) * | 1982-11-10 | 1986-08-12 | Kyoto Pharmaceutical Industries, Ltd. | Antibiotic amino acid derivatives of cephalosporins |
| CN111187284A (en) * | 2020-03-10 | 2020-05-22 | 赵俊瑶 | Preparation method of cefaclor |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1022544A (en) * | 1972-12-21 | 1977-12-13 | Yukiyasu Murakami | Process of preparing a heterocyclic acyl group-substituted cephalosporin derivative |
| KR780000197B1 (en) * | 1972-12-26 | 1978-05-26 | Bristol Myers Co | Method for preparing antibacterial agent |
| CA1035353A (en) * | 1973-01-31 | 1978-07-25 | Lee C. Cheney | 3-thiolated-7-acylamidocephalosporanic acids |
| JPS5732075B2 (en) * | 1974-02-20 | 1982-07-08 | ||
| JPS5732074B2 (en) * | 1974-01-30 | 1982-07-08 | ||
| AR205537A1 (en) * | 1973-05-10 | 1976-05-14 | Fujisawa Pharmaceutical Co | PROCEDURE FOR THE PREPARATION OF ACID DERIVATIVES 7-SUBSTITUTED PHENYLGLYCINAMIDE - 3 - SUBSTITUTED - 3 - CEFEM - 4 - CARBOXYL |
| CA1030523A (en) * | 1973-06-25 | 1978-05-02 | Taiiti Okada | Cephalosporins |
| JPS5729475B2 (en) * | 1974-04-11 | 1982-06-23 | ||
| GB1476981A (en) * | 1974-06-05 | 1977-06-16 | Bristol Myers Co | Substituted penicillanic acids |
| IL48090A0 (en) * | 1974-09-19 | 1975-11-25 | Merck Patent Gmbh | Cephem derivatives,their preparation and compositions containing them |
| US3994876A (en) * | 1975-07-22 | 1976-11-30 | Richardson-Merrell Inc. | 6-[α-AMINO-ω-(2,3-METHYLENEDIOXYPHENYL)ACYLAMIDO]PENICILLANIC ACID DERIVATIVES |
| US3994877A (en) * | 1975-07-22 | 1976-11-30 | Richardson-Merrell Inc. | 6-[α-AMINO-ω-(3,4-METHYLENEDIOXYPHENYL)ACYLAMIDO]PENICILLANIC ACID DERIVATIVES |
| GB1579532A (en) * | 1976-05-21 | 1980-11-19 | Farmaceutici Italia | Cephalosporins |
| CH634848A5 (en) * | 1976-08-17 | 1983-02-28 | Fujisawa Pharmaceutical Co | METHOD FOR PRODUCING NEW 7- (N-SUBSTITUTED 2-PHENYLGLYCINAMIDO) -3-SUBSTITUTED-3-CEPHEM-4-CARBONIC ACIDS. |
| US4319028A (en) * | 1976-08-26 | 1982-03-09 | Eli Lilly And Company | 7-(2-(Substituted benzoyl)amino)acetamido)cephalosporins |
| GR74995B (en) * | 1980-08-27 | 1984-07-12 | Ciba Geigy Ag |
-
1971
- 1971-11-08 IL IL38099A patent/IL38099A/en unknown
- 1971-11-26 PH PH13047*UA patent/PH9531A/en unknown
- 1971-11-29 CA CA128,798A patent/CA990281A/en not_active Expired
- 1971-12-03 BE BE776222A patent/BE776222A/en unknown
- 1971-12-07 NL NL7116791A patent/NL7116791A/xx unknown
- 1971-12-08 IE IE1555/71A patent/IE35875B1/en unknown
- 1971-12-10 FR FR7144419A patent/FR2118012B1/fr not_active Expired
- 1971-12-13 CH CH1815971A patent/CH578581A5/xx not_active IP Right Cessation
- 1971-12-13 AU AU36827/71A patent/AU459002B2/en not_active Expired
- 1971-12-15 DD DD159606A patent/DD94997A5/xx unknown
- 1971-12-15 BR BR8309/71A patent/BR7108309D0/en unknown
- 1971-12-15 IT IT32444/71A patent/IT1061965B/en active
- 1971-12-16 DE DE19712162575 patent/DE2162575A1/en active Pending
- 1971-12-16 GB GB5838671A patent/GB1328340A/en not_active Expired
- 1971-12-16 HU HUSI1240A patent/HU166307B/hu unknown
- 1971-12-16 RO RO7169075A patent/RO59318A/en unknown
- 1971-12-17 AR AR239670A patent/AR194216A1/en active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3936446A (en) * | 1974-02-19 | 1976-02-03 | Beecham Group Limited | Isocyanocephalosporanates |
| US4605651A (en) * | 1982-11-10 | 1986-08-12 | Kyoto Pharmaceutical Industries, Ltd. | Antibiotic amino acid derivatives of cephalosporins |
| CN111187284A (en) * | 2020-03-10 | 2020-05-22 | 赵俊瑶 | Preparation method of cefaclor |
Also Published As
| Publication number | Publication date |
|---|---|
| PH9531A (en) | 1976-01-09 |
| IE35875L (en) | 1972-06-17 |
| BE776222A (en) | 1972-06-05 |
| RO59318A (en) | 1981-01-30 |
| CA990281A (en) | 1976-06-01 |
| AU459002B2 (en) | 1975-03-13 |
| IL38099A (en) | 1976-01-30 |
| FR2118012A1 (en) | 1972-07-28 |
| HU166307B (en) | 1975-02-28 |
| AU3682771A (en) | 1973-06-14 |
| BR7108309D0 (en) | 1973-07-03 |
| IT1061965B (en) | 1983-04-30 |
| AR194216A1 (en) | 1973-06-29 |
| CH578581A5 (en) | 1976-08-13 |
| IE35875B1 (en) | 1976-06-09 |
| DE2162575A1 (en) | 1972-07-27 |
| NL7116791A (en) | 1972-06-20 |
| FR2118012B1 (en) | 1975-10-31 |
| DD94997A5 (en) | 1973-01-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |