DE2262472A1 - Acylderivate - Google Patents
AcylderivateInfo
- Publication number
- DE2262472A1 DE2262472A1 DE2262472A DE2262472A DE2262472A1 DE 2262472 A1 DE2262472 A1 DE 2262472A1 DE 2262472 A DE2262472 A DE 2262472A DE 2262472 A DE2262472 A DE 2262472A DE 2262472 A1 DE2262472 A1 DE 2262472A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- cooh
- salt
- salts
- formula
- 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- Withdrawn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
- 150000003839 salts Chemical class 0.000 claims description 29
- 159000000000 sodium salts Chemical class 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 150000004677 hydrates Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000003115 biocidal effect Effects 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 4
- 239000000969 carrier Substances 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- 239000000243 solution Substances 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- -1 alkali metal salts Chemical class 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 229940049954 penicillin Drugs 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229930182555 Penicillin Natural products 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229960002317 succinimide Drugs 0.000 description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 4
- 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 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical class ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- 229940124587 cephalosporin Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 2
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 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 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- NYHNVHGFPZAZGA-RXMQYKEDSA-N (2r)-2-hydroxyhexanoic acid Chemical compound CCCC[C@@H](O)C(O)=O NYHNVHGFPZAZGA-RXMQYKEDSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CRPFKUKPDCBUIX-UHFFFAOYSA-N 2-ethyl-5-phenyl-1,2-oxazol-2-ium-3-sulfonate Chemical compound [O-]S(=O)(=O)C1=[N+](CC)OC(C=2C=CC=CC=2)=C1 CRPFKUKPDCBUIX-UHFFFAOYSA-N 0.000 description 1
- LVRFTAZAXQPQHI-UHFFFAOYSA-N 2-hydroxy-4-methylvaleric acid Chemical compound CC(C)CC(O)C(O)=O LVRFTAZAXQPQHI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical class C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 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
- 150000001540 azides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 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
- 239000012267 brine Substances 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000007928 imidazolide derivatives Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- OALPPYUMFWGHEK-UHFFFAOYSA-M potassium;benzenethiolate Chemical compound [K+].[S-]C1=CC=CC=C1 OALPPYUMFWGHEK-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
-
- 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 |
|---|---|---|---|
| CH572A CH565182A5 (enrdf_load_stackoverflow) | 1972-01-03 | 1972-01-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2262472A1 true DE2262472A1 (de) | 1973-07-19 |
Family
ID=4177249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2262472A Withdrawn DE2262472A1 (de) | 1972-01-03 | 1972-12-20 | Acylderivate |
Country Status (16)
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB940712A (en) * | 1961-06-23 | 1963-10-30 | Beecham Res Lab | Improvements in or relating to penicillins |
| FR1393245A (fr) * | 1962-05-21 | 1965-03-26 | Beecham Group Ltd | Procédé de préparation de pénicillines |
| FR1393244A (fr) * | 1962-05-21 | 1965-03-26 | Beecham Group Ltd | Procédé pour la préparation de pénicillines |
| SE311519B (enrdf_load_stackoverflow) * | 1962-12-14 | 1969-06-16 | Astra Ab |
-
0
- BE BE793595D patent/BE793595A/xx unknown
-
1972
- 1972-01-03 CH CH572A patent/CH565182A5/xx not_active IP Right Cessation
- 1972-11-27 ZA ZA728418A patent/ZA728418B/xx unknown
- 1972-12-01 DK DK603572AA patent/DK140553B/da unknown
- 1972-12-01 IL IL40978A patent/IL40978A/xx unknown
- 1972-12-20 DE DE2262472A patent/DE2262472A1/de not_active Withdrawn
- 1972-12-22 PH PH14198A patent/PH11075A/en unknown
- 1972-12-22 NL NL7217543A patent/NL7217543A/xx not_active Application Discontinuation
-
1973
- 1973-01-01 AR AR245959A patent/AR205150A1/es active
- 1973-01-02 SE SE7300033A patent/SE412065B/xx unknown
- 1973-01-02 AT AT1373A patent/AT320153B/de not_active IP Right Cessation
- 1973-01-02 CA CA160,421A patent/CA1001155A/en not_active Expired
- 1973-01-02 IE IE2/73A patent/IE37053B1/xx unknown
- 1973-01-02 GB GB20273A patent/GB1355629A/en not_active Expired
- 1973-01-03 FR FR7300110A patent/FR2181649B1/fr not_active Expired
- 1973-01-03 HU HU73HO1538A patent/HU170008B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU4949272A (en) | 1974-05-30 |
| IE37053L (en) | 1973-07-03 |
| CH565182A5 (enrdf_load_stackoverflow) | 1975-08-15 |
| IE37053B1 (en) | 1977-04-27 |
| HU170008B (en) | 1977-03-28 |
| NL7217543A (enrdf_load_stackoverflow) | 1973-07-05 |
| DK140553C (enrdf_load_stackoverflow) | 1980-02-18 |
| FR2181649B1 (enrdf_load_stackoverflow) | 1976-03-05 |
| PH11075A (en) | 1977-10-25 |
| ZA728418B (en) | 1973-08-29 |
| IL40978A (en) | 1975-10-15 |
| FR2181649A1 (enrdf_load_stackoverflow) | 1973-12-07 |
| BE793595A (fr) | 1973-07-02 |
| AR205150A1 (es) | 1976-04-12 |
| CA1001155A (en) | 1976-12-07 |
| SE412065B (sv) | 1980-02-18 |
| DK140553B (da) | 1979-10-01 |
| AT320153B (de) | 1975-01-27 |
| IL40978A0 (en) | 1973-02-28 |
| GB1355629A (en) | 1974-06-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2416449C2 (de) | Penicilline und ihre Verwendung bei der Bekämpfung bakterieller Infektionen | |
| DE2301544A1 (de) | Acylderivate | |
| DE2529941A1 (de) | Azetidinonderivate und verfahren zu ihrer herstellung | |
| CH638680A5 (de) | Verfahren zur herstellung einer injizierbaren waessrigen loesung eines cephalosporinantibiotikums. | |
| DE2901843A1 (de) | Verfahren zur herstellung von carbonsaeureamiden und peptiden | |
| DE1795188B2 (de) | 3-Alkoxymethylcephalosporine, Verfahren zu deren Herstellung und die diese enthaltenden pharmazeutischen Zusammensetzungen | |
| CH641468A5 (de) | Cephemderivate. | |
| DE3885031T2 (de) | Wasserlösliches antibiotisches Präparat und wasserlösliche Salze von Cephem-Verbindungen. | |
| DE2155081B2 (de) | 7- (lsoxazol-5-yl-acetamido)cephalosporansäurederivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE2638067C2 (de) | Penicilline und Verfahren zu deren Herstellung | |
| DE2521063A1 (de) | Phenylacetamidocephalosporin- derivate | |
| DE2262472A1 (de) | Acylderivate | |
| DE2055531B2 (de) | Anüdinopenicillansaurederivate, Verfahren zur Herstellung dieser Verbindungen und ihre Verwendung bei der Bekämpfung von Infektionskrankheiten | |
| CH671020A5 (enrdf_load_stackoverflow) | ||
| DE2824065A1 (de) | Acylderivate | |
| DE3231596A1 (de) | Penem-3-carbonsaeurederivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen | |
| DE2857816C2 (de) | 7ß-(substituierte-Isothiazol)thioacetamido-7-methoxy(alkylsubstituierte-tetraz olyl)thiomethyl-Δ↑3↑-cephem-4-carbonsäuren, Verfahren zu ihrer Herstellung und deren Verwendung | |
| DE2163600A1 (de) | Acylderivate | |
| DE1815396A1 (de) | Verfahren zur Herstellung von Penicilloinsaeurederivaten | |
| DE2106500C3 (de) | deren Salze und Verfahren zu deren Herstellung | |
| DE2644335A1 (de) | 2-niedrig-alkyl-7-subst.-2- oder -3-cephem-4-carbonsaeureverbindungen und verfahren zu ihrer herstellung | |
| DE2852745A1 (de) | Neue penicillin- und cephalosporinderivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| DE1695313A1 (de) | Verfahren zur Herstellung von 6-Amino-penicillansaeure | |
| DE1545838C3 (de) | 7-(2-Azidooctanamido)-cephalosporansäure, deren Salze und Verfahren zur Herstellung dieser Verbindungen | |
| DE2025415B2 (de) | Verfahren zur Herstellung von cyclischen Acylureido-Penicillinen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8139 | Disposal/non-payment of the annual fee |