DE2000111A1 - Oral wirksame schwefelhaltige Cephalosporinantibiotica - Google Patents
Oral wirksame schwefelhaltige CephalosporinantibioticaInfo
- Publication number
- DE2000111A1 DE2000111A1 DE19702000111 DE2000111A DE2000111A1 DE 2000111 A1 DE2000111 A1 DE 2000111A1 DE 19702000111 DE19702000111 DE 19702000111 DE 2000111 A DE2000111 A DE 2000111A DE 2000111 A1 DE2000111 A1 DE 2000111A1
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acid
- acid
- group
- compound
- phenyl radical
- 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.)
- Pending
Links
- 229940124587 cephalosporin Drugs 0.000 title description 4
- 229930186147 Cephalosporin Natural products 0.000 title description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title description 3
- 239000003242 anti bacterial agent Substances 0.000 title description 3
- 229940088710 antibiotic agent Drugs 0.000 title description 3
- 150000001780 cephalosporins Chemical class 0.000 title description 3
- 239000011593 sulfur Substances 0.000 title description 3
- 229910052717 sulfur Inorganic materials 0.000 title description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- 239000000243 solution Substances 0.000 claims description 26
- -1 thienyl radical Chemical group 0.000 claims description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Chemical class 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 8
- 230000010933 acylation Effects 0.000 claims description 8
- 238000005917 acylation reaction Methods 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000005331 phenylglycines Chemical class 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 239000011260 aqueous acid Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000006894 reductive elimination reaction Methods 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 2
- UJCHIZDEQZMODR-BYPYZUCNSA-N (2r)-2-acetamido-3-sulfanylpropanamide Chemical compound CC(=O)N[C@@H](CS)C(N)=O UJCHIZDEQZMODR-BYPYZUCNSA-N 0.000 claims 1
- 241001669680 Dormitator maculatus Species 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 101000724404 Homo sapiens Saccharopine dehydrogenase Proteins 0.000 claims 1
- 102100028294 Saccharopine dehydrogenase Human genes 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000006031 2-methyl-3-butenyl group Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- 230000002829 reductive effect Effects 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- MAFIPFSQYBWLAM-BAFYGKSASA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid Chemical compound OC(=O)C1C=CS[C@@H]2CC(=O)N12 MAFIPFSQYBWLAM-BAFYGKSASA-N 0.000 description 1
- HOBFSNNENNQQIU-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylacetic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)C1=CC=CC=C1 HOBFSNNENNQQIU-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 229930195708 Penicillin V Natural products 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001782 cephems Chemical class 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229940056367 penicillin v Drugs 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 108090000765 processed proteins & peptides Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 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
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80264369A | 1969-02-26 | 1969-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2000111A1 true DE2000111A1 (de) | 1970-09-10 |
Family
ID=25184304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702000111 Pending DE2000111A1 (de) | 1969-02-26 | 1970-01-02 | Oral wirksame schwefelhaltige Cephalosporinantibiotica |
Country Status (17)
| Country | Link |
|---|---|
| AT (1) | AT296501B (en, 2012) |
| BE (1) | BE743754A (en, 2012) |
| BR (1) | BR6915176D0 (en, 2012) |
| CH (1) | CH536321A (en, 2012) |
| DE (1) | DE2000111A1 (en, 2012) |
| DO (1) | DOP1970001696A (en, 2012) |
| ES (1) | ES375237A1 (en, 2012) |
| FR (1) | FR2032408B1 (en, 2012) |
| GB (1) | GB1261780A (en, 2012) |
| GT (1) | GT196915584A (en, 2012) |
| IL (1) | IL33522A0 (en, 2012) |
| LU (1) | LU60150A1 (en, 2012) |
| NL (1) | NL6919698A (en, 2012) |
| PL (1) | PL80818B1 (en, 2012) |
| RO (1) | RO56960A (en, 2012) |
| SU (1) | SU383302A3 (en, 2012) |
| ZA (1) | ZA698494B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7112483A (en, 2012) * | 1970-09-14 | 1972-03-16 | ||
| GB1385895A (en) * | 1971-03-01 | 1975-03-05 | Glaxo Lab Ltd | Antibiotics |
| CA1076560A (en) * | 1972-06-14 | 1980-04-29 | Smith Kline And French Canada Ltd. | 3-heterocyclic thiomethylcephalosporins |
| US4409215A (en) * | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical Co., Ltd. | 7-Acylamino-3-substituted cephalosporanic acid derivatives and processes for the preparation thereof |
-
1969
- 1969-12-05 ZA ZA698494A patent/ZA698494B/xx unknown
- 1969-12-11 IL IL33522A patent/IL33522A0/xx unknown
- 1969-12-15 BR BR215176/69A patent/BR6915176D0/pt unknown
- 1969-12-24 BE BE743754D patent/BE743754A/xx unknown
- 1969-12-24 SU SU1389812A patent/SU383302A3/ru active
- 1969-12-26 FR FR6945111A patent/FR2032408B1/fr not_active Expired
- 1969-12-26 GT GT196915584A patent/GT196915584A/es unknown
- 1969-12-31 NL NL6919698A patent/NL6919698A/xx unknown
- 1969-12-31 GB GB63526/69A patent/GB1261780A/en not_active Expired
-
1970
- 1970-01-02 PL PL1970137933A patent/PL80818B1/pl unknown
- 1970-01-02 DE DE19702000111 patent/DE2000111A1/de active Pending
- 1970-01-06 RO RO62053A patent/RO56960A/ro unknown
- 1970-01-07 LU LU60150D patent/LU60150A1/xx unknown
- 1970-01-07 ES ES375237A patent/ES375237A1/es not_active Expired
- 1970-01-07 DO DO1970001696A patent/DOP1970001696A/es unknown
- 1970-01-07 AT AT11670A patent/AT296501B/de not_active IP Right Cessation
- 1970-01-07 CH CH10970A patent/CH536321A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE743754A (en, 2012) | 1970-06-24 |
| IL33522A0 (en) | 1970-02-19 |
| DOP1970001696A (es) | 1974-12-09 |
| LU60150A1 (en, 2012) | 1970-07-09 |
| SU383302A3 (en, 2012) | 1973-05-25 |
| RO56960A (en, 2012) | 1974-11-11 |
| CH536321A (de) | 1973-04-30 |
| GB1261780A (en) | 1972-01-26 |
| PL80818B1 (en, 2012) | 1975-08-30 |
| AT296501B (de) | 1972-02-25 |
| FR2032408B1 (en, 2012) | 1974-02-01 |
| ES375237A1 (es) | 1972-03-16 |
| FR2032408A1 (en, 2012) | 1970-11-27 |
| GT196915584A (es) | 1971-06-19 |
| NL6919698A (en, 2012) | 1970-08-28 |
| ZA698494B (en) | 1971-07-28 |
| BR6915176D0 (pt) | 1973-02-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2760156C2 (en, 2012) | ||
| DE2018600C3 (de) | 3-Thiadiazolylmercaptomethyl- und -Tetrazolylmercaptomethylcephalosporine und Verfahren zu ihrer Herstellung | |
| DE2812625C2 (en, 2012) | ||
| DE2462736B1 (de) | 7-Aminothiazolylacetamido-3-cephem-4-carbonsaeuren und Verfahren zur Herstellung derselben | |
| CH633558A5 (de) | Verfahren zur herstellung neuer cephalosporinderivate. | |
| DE2331078C2 (de) | 3-Substituierte 7β-Amino-cepham-4-carbonsäureverbindungen | |
| JPS6140235B2 (en, 2012) | ||
| AT392072B (de) | Verfahren zur herstellung der neuen 7-amino-3propenylcephalosporansaeure sowie von estern und salzen derselben | |
| DE2312997A1 (de) | Verfahren zur herstellung von 7-(alphahydroxy-alpha-phenyl)-acetamido-3-(1-methyl1h-tetrazol-5-ylthiomethyl)-3-cephem-4carbonsaeure und derivaten davon | |
| CH622523A5 (en, 2012) | ||
| DE2000111A1 (de) | Oral wirksame schwefelhaltige Cephalosporinantibiotica | |
| DE2451931C2 (de) | 7β-Acylamido-7α-methoxycephalosporine, Verfahren zu ihrer Herstellung und sie enthaltendes antibiotisches Mittel | |
| DE2160319A1 (de) | Verfahren zur Herstellung von Cephalosporinderivaten | |
| DE2538801A1 (de) | Cephalosporinderivate und verfahren zu ihrer herstellung | |
| DE2612926A1 (de) | Neue acyl-derivate der 6-(alpha- amino-phenylacetamido)-penicillansaeure | |
| DE2225149A1 (de) | Neue Oxofurylesterdenvate von Penicillin und Cephalosporin | |
| DE2259176A1 (de) | Schwerloesliche salze von cephalexin, ihre herstellung und verwendung | |
| DE2633005A1 (de) | Cephem- und penamverbindungen und verfahren zu ihrer herstellung | |
| CH631988A5 (de) | Verfahren zur herstellung von 3-(alkylsulfonamidoalkyltetrazolylthiomethyl)-cephalosporin-derivaten. | |
| CH638781A5 (de) | Verfahren zur herstellung von beta-lactamen. | |
| DE2755902A1 (de) | Verfahren zur herstellung von cephalosporinen | |
| DE2818025A1 (de) | Verfahren zur herstellung von cephemverbindungen | |
| CH633290A5 (en) | Process for preparing derivatives of 7-oxo-1,3-diazabicyclo[3.2.0]heptane-2-carboxylic acid | |
| DD201142A5 (de) | Verfahren zur herstellung von bistetrazolyl-methylsubstituierten cephalosporiantibiotika | |
| DE2404592C2 (de) | In 3-Stellung thiolierte 7-Acyl-amidocephalosporansäurederivate, Verfahren zu deren Herstellung und sie enthaltende Mittel |