DE2456307A1 - Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel - Google Patents
Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittelInfo
- Publication number
- DE2456307A1 DE2456307A1 DE19742456307 DE2456307A DE2456307A1 DE 2456307 A1 DE2456307 A1 DE 2456307A1 DE 19742456307 DE19742456307 DE 19742456307 DE 2456307 A DE2456307 A DE 2456307A DE 2456307 A1 DE2456307 A1 DE 2456307A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- parts
- compound
- weight
- compounds
- 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.)
- Withdrawn
Links
- 229930182555 Penicillin Natural products 0.000 title abstract description 16
- 150000002960 penicillins Chemical class 0.000 title abstract description 13
- 229930186147 Cephalosporin Natural products 0.000 title abstract description 6
- 229940124587 cephalosporin Drugs 0.000 title abstract description 6
- 150000001780 cephalosporins Chemical class 0.000 title abstract description 6
- 239000003674 animal food additive Substances 0.000 title abstract description 3
- -1 cycloalkedienyl Chemical group 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 12
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 11
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims abstract description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 4
- PFZCOWLKXHIVII-UHFFFAOYSA-N pyridin-1-ium-1-amine Chemical compound N[N+]1=CC=CC=C1 PFZCOWLKXHIVII-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 68
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 159000000000 sodium salts Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 239000002132 β-lactam antibiotic Substances 0.000 claims description 11
- 229940124586 β-lactam antibiotics Drugs 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000001540 azides Chemical class 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 125000001485 cycloalkadienyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 230000001737 promoting effect Effects 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000003460 beta-lactamyl group Chemical group 0.000 claims 2
- 102000020897 Formins Human genes 0.000 claims 1
- 108091022623 Formins Proteins 0.000 claims 1
- BCTILSWHJRTUIE-UHFFFAOYSA-N azanium;4-[4-[bis[4-(dimethylamino)phenyl]-hydroxymethyl]-3-methyl-5-oxo-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [NH4+].C1=CC(N(C)C)=CC=C1C(O)(C=1C=CC(=CC=1)N(C)C)C1C(=O)N(C=2C=CC(=CC=2)S([O-])(=O)=O)N=C1C BCTILSWHJRTUIE-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 32
- 125000003118 aryl group Chemical group 0.000 abstract description 9
- 239000003242 anti bacterial agent Substances 0.000 abstract description 7
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 7
- 229940088710 antibiotic agent Drugs 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 239000000314 lubricant Substances 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 238000001228 spectrum Methods 0.000 abstract description 3
- 102000006635 beta-lactamase Human genes 0.000 abstract description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 abstract 1
- 108090000204 Dipeptidase 1 Proteins 0.000 abstract 1
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000565 sulfonamide group Chemical group 0.000 abstract 1
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 abstract 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- 229910001868 water Inorganic materials 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- 239000004480 active ingredient Substances 0.000 description 29
- 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 28
- 229910052708 sodium Inorganic materials 0.000 description 27
- 239000011734 sodium Substances 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 239000000460 chlorine Substances 0.000 description 23
- 239000000126 substance Substances 0.000 description 19
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 18
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 150000003952 β-lactams Chemical class 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
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- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
- 229910052794 bromium Inorganic materials 0.000 description 12
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 12
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- 125000005842 heteroatom Chemical group 0.000 description 10
- 229940049954 penicillin Drugs 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (31)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742456307 DE2456307A1 (de) | 1974-11-28 | 1974-11-28 | Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| GB44296/75A GB1486349A (en) | 1974-11-28 | 1975-10-28 | Beta-lactam antibiotics process for their preparation and their use as medicaments |
| US05/631,515 US4147693A (en) | 1974-11-28 | 1975-11-13 | βLactam antibiotics and process for their use |
| NO753818A NO753818L (cs) | 1974-11-28 | 1975-11-14 | |
| CA239,913A CA1064020A (en) | 1974-11-28 | 1975-11-18 | .beta.-LACTAM ANTIBIOTICS AND PROCESSES FOR THEIR PREPARATION AND USE |
| SU752189965A SU663307A3 (ru) | 1974-11-28 | 1975-11-20 | Способ получени производных пенициллина или цефалоспорина или их солей в виде смеси изомеров или отдельных изомеров или гидратов |
| CH1523375A CH623326A5 (cs) | 1974-11-28 | 1975-11-24 | |
| NL7513746A NL7513746A (nl) | 1974-11-28 | 1975-11-25 | (beta)-lactam-antibiotica, werkwijzen ter bereiding alsmede de toepassing ervan als geneesmiddelen. |
| NZ179347A NZ179347A (en) | 1974-11-28 | 1975-11-25 | Penicillins and cephalosporins, pharmaceutical compositions and medicated fodder |
| IL48538A IL48538A (en) | 1974-11-28 | 1975-11-25 | Penicillins and cephalosporins with imidazolidinone groupstheir preparation and pharmaceutical compositions containig them |
| JP50140877A JPS5182286A (en) | 1974-11-28 | 1975-11-26 | Beetaa rakutamu no seizoho |
| JP50140878A JPS6043332B2 (ja) | 1974-11-28 | 1975-11-26 | 人間以外の動物用抗菌剤 |
| DD189709A DD124736A5 (cs) | 1974-11-28 | 1975-11-26 | |
| ES443008A ES443008A1 (es) | 1974-11-28 | 1975-11-26 | Procedimiento para preparar antibioticos de beta-lactama. |
| FI753333A FI66004C (fi) | 1974-11-28 | 1975-11-26 | Foerfarande foer framstaellning av beta-laktamantibiotika anvaendbara saosom laekemedel |
| PL18498775A PL98550B1 (pl) | 1974-11-28 | 1975-11-26 | Sposob wytwarzania nowego beta-laktamowego antybiotyku |
| HU75BA3343A HU173952B (hu) | 1974-11-28 | 1975-11-26 | Sposob poluchenija novykh beta-laktam antibiotikov i farmacevticheskikh kompozicijj soderzhahhikh ikh aktivnymi agentami |
| RO7584030A RO68146A (ro) | 1974-11-28 | 1975-11-26 | Procedeu pentru prepararea unor beta-lactam -derivati ai penicilinei si cefalosporinei |
| LU73873A LU73873A1 (cs) | 1974-11-28 | 1975-11-26 | |
| IE1794/80A IE43814B1 (en) | 1974-11-28 | 1975-11-27 | -lactam antibiotics,process for their preparation and their use as medicaments |
| DK535675A DK535675A (da) | 1974-11-28 | 1975-11-27 | Beta-lactam-antibiotika samt deres fremstilling og anvendelse |
| ZA00757482A ZA757482B (en) | 1974-11-28 | 1975-11-27 | B-lactam antibiotics, process for their preparation and their use as medicaments |
| IE2588/75A IE43813B1 (en) | 1974-11-28 | 1975-11-27 | -lactam antibiotics,process for their preparation and their use as medicaments |
| SE7513378A SE434513B (sv) | 1974-11-28 | 1975-11-27 | Sett att framstella nya derivat av 6-((2-oxo-imidazolidin-1-yl)karbonylamino)acetamido)penicillinsyra |
| BE162237A BE836022A (fr) | 1974-11-28 | 1975-11-27 | Nouveaux antibiotiques du type beta-lactame, leur procede de preparation et medicament les contenant |
| AR261391A AR210103A1 (es) | 1974-11-28 | 1975-11-28 | Procedimiento para la produccion de nuevos derivados de aci-6(d-a-((2-oxo imidazolidin-1-il)-carbonilamino)-4-acetamido)-penicilanico y de acido 7-(d-a((2-oxo-imidazolidin-1-il)-carbonilamino)-4-acetamido)-cef-3-em-4-carboxilico |
| AT907275A AT342196B (de) | 1974-11-28 | 1975-11-28 | Verfahren zur herstellung von neuen beta-lactam-antibiotica |
| AU87085/75A AU499337B2 (en) | 1974-11-28 | 1975-11-28 | Penicillins & cephalosporins |
| CS758091A CS188982B2 (en) | 1974-11-28 | 1975-11-28 | Process for preparing antibiotics of 3-n-substituted imidazolidin-1-yl carbonylamino-beta-lactame |
| FR7536543A FR2292471A1 (fr) | 1974-11-28 | 1975-11-28 | Nouveaux antibiotiques du type b-lactame, leur procede de preparation et medicament les contenant |
| HK196/78A HK19678A (en) | 1974-11-28 | 1978-04-13 | Beta-lactam antibiotics, process for their preparation and their use as medicaments |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742456307 DE2456307A1 (de) | 1974-11-28 | 1974-11-28 | Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2456307A1 true DE2456307A1 (de) | 1976-08-12 |
Family
ID=5931964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742456307 Withdrawn DE2456307A1 (de) | 1974-11-28 | 1974-11-28 | Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE836022A (cs) |
| CS (1) | CS188982B2 (cs) |
| DE (1) | DE2456307A1 (cs) |
| HU (1) | HU173952B (cs) |
| ZA (1) | ZA757482B (cs) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000393A1 (de) * | 1977-07-16 | 1979-01-24 | Bayer Ag | Beta-Lactam-Verbindungen, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| EP0000380A1 (de) * | 1977-07-15 | 1979-01-24 | Bayer Ag | Penicilline, Verfahren zu ihrer Herstellung und ihre Verwendung |
| WO1995007275A1 (de) * | 1993-09-10 | 1995-03-16 | Ciba-Geigy Ag | Photochrome verbindungen, verfahren und zwischenprodukte zu deren hestellung und deren verwendung |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1593524A (en) * | 1976-11-19 | 1981-07-15 | Merck & Co Inc | 1-carba-2-penem-3-carboxylic acids |
| US4189482A (en) * | 1978-10-12 | 1980-02-19 | E. R. Squibb & Sons, Inc. | Penicillins having an imino substituted piperazindioncarbonylamino acyl sidechain |
| US4231928A (en) * | 1979-04-24 | 1980-11-04 | Bristol-Myers Company | Antibacterial agents |
-
1974
- 1974-11-28 DE DE19742456307 patent/DE2456307A1/de not_active Withdrawn
-
1975
- 1975-11-26 HU HU75BA3343A patent/HU173952B/hu unknown
- 1975-11-27 BE BE162237A patent/BE836022A/xx not_active IP Right Cessation
- 1975-11-27 ZA ZA00757482A patent/ZA757482B/xx unknown
- 1975-11-28 CS CS758091A patent/CS188982B2/cs unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000380A1 (de) * | 1977-07-15 | 1979-01-24 | Bayer Ag | Penicilline, Verfahren zu ihrer Herstellung und ihre Verwendung |
| EP0000393A1 (de) * | 1977-07-16 | 1979-01-24 | Bayer Ag | Beta-Lactam-Verbindungen, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| WO1995007275A1 (de) * | 1993-09-10 | 1995-03-16 | Ciba-Geigy Ag | Photochrome verbindungen, verfahren und zwischenprodukte zu deren hestellung und deren verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA757482B (en) | 1976-10-27 |
| CS188982B2 (en) | 1979-03-30 |
| BE836022A (fr) | 1976-05-28 |
| HU173952B (hu) | 1979-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |