DE2011885C3 - 1,4-Dihydro-3-carboxy-cyclopentano (h)-chinolon-(4)-derivate, Verfahren zur Herstellung derselben und ihre Verwendung - Google Patents
1,4-Dihydro-3-carboxy-cyclopentano (h)-chinolon-(4)-derivate, Verfahren zur Herstellung derselben und ihre VerwendungInfo
- Publication number
- DE2011885C3 DE2011885C3 DE2011885A DE2011885A DE2011885C3 DE 2011885 C3 DE2011885 C3 DE 2011885C3 DE 2011885 A DE2011885 A DE 2011885A DE 2011885 A DE2011885 A DE 2011885A DE 2011885 C3 DE2011885 C3 DE 2011885C3
- Authority
- DE
- Germany
- Prior art keywords
- quinolone
- dihydro
- carboxy
- cyclopentano
- derivatives
- 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
- 238000000034 method Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 7
- 208000019206 urinary tract infection Diseases 0.000 claims description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000003385 bacteriostatic effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 210000002700 urine Anatomy 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000001852 germinostatic effect Effects 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
- FNPFKJBUDLMKCO-UHFFFAOYSA-N 1-prop-2-enylquinolin-2-one Chemical compound C1=CC=C2C=CC(=O)N(CC=C)C2=C1 FNPFKJBUDLMKCO-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 241000588767 Proteus vulgaris Species 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 231100000460 acute oral toxicity Toxicity 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- -1 allyl quinolone Chemical compound 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229960000564 nitrofurantoin Drugs 0.000 description 2
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229940007042 proteus vulgaris Drugs 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Chemical group 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2011885A DE2011885C3 (de) | 1970-03-13 | 1970-03-13 | 1,4-Dihydro-3-carboxy-cyclopentano (h)-chinolon-(4)-derivate, Verfahren zur Herstellung derselben und ihre Verwendung |
| SU1618801A SU434653A3 (ru) | 1970-03-13 | 1971-02-08 | Способ получения n-винилхинолонов |
| SU1747931A SU436493A3 (enExample) | 1970-03-13 | 1971-02-08 | |
| ES388909A ES388909A1 (es) | 1970-03-13 | 1971-03-04 | Procedimiento para la preparacion de nuevas n-vinilquinolo-nas. |
| BG018790A BG18416A3 (bg) | 1970-03-13 | 1971-03-04 | Метод за получаване на n-винилхинолони |
| BG016969A BG18415A3 (bg) | 1970-03-13 | 1971-03-04 | Метод за получаване на n- винилхинолони |
| CH550674A CH558359A (de) | 1970-03-13 | 1971-03-10 | Verfahren zur herstellung von neuen n-vinylchinolonen sowie deren salzen. |
| DK112171AA DK129839B (da) | 1970-03-13 | 1971-03-10 | Analogifremgangsmåde til fremstilling af N-vinylquinoloner eller syreadditionssalte deraf. |
| CH352771A CH558358A (de) | 1970-03-13 | 1971-03-10 | Verfahren zur herstellung von n-vinylchinolonen. |
| CS1805A CS161899B2 (enExample) | 1970-03-13 | 1971-03-11 | |
| RO66229A RO58367A (enExample) | 1970-03-13 | 1971-03-11 | |
| IL36397A IL36397A (en) | 1970-03-13 | 1971-03-11 | N-vinyl-quinolones,processes for the preparation thereof and pharmaceutical compositions containing the same |
| NL717103247A NL145854B (nl) | 1970-03-13 | 1971-03-11 | Werkwijze ter bereiding van n-alkenylchinolonen en van farmaceutische preparaten met antibacteriele werking. |
| CS5256*A CS161900B2 (enExample) | 1970-03-13 | 1971-03-11 | |
| ZA711607A ZA711607B (en) | 1970-03-13 | 1971-03-11 | New n-vinyl-quinolones and the preparation thereof |
| RO68915A RO58563A (enExample) | 1970-03-13 | 1971-03-11 | |
| IE308/71A IE35111B1 (en) | 1970-03-13 | 1971-03-12 | N-vinyl-quinolones |
| CA107,660A CA944355A (en) | 1970-03-13 | 1971-03-12 | N-vinyl-quinolones and process for their preparation |
| AT00541/72A AT303735B (de) | 1970-03-13 | 1971-03-12 | Verfahren zur herstellung von neuen n-vinylchinolonen sowie deren salzen |
| FR7108638A FR2085701B1 (enExample) | 1970-03-13 | 1971-03-12 | |
| PL1971146843A PL82724B1 (en) | 1970-03-13 | 1971-03-12 | N-vinyl-quinolones[gb1282076a] |
| AT218371A AT303734B (de) | 1970-03-13 | 1971-03-12 | Verfahren zur Herstellung von neuen N-Vinylchinolonen sowie deren Salzen |
| SE03194/71A SE361313B (enExample) | 1970-03-13 | 1971-03-12 | |
| FI710732A FI49501C (fi) | 1970-03-13 | 1971-03-12 | Menetelmä antibakteerisesti vaikuttavien N-vinyylikinolonien valmistam iseksi. |
| JP46014018A JPS4835268B2 (enExample) | 1970-03-13 | 1971-03-13 | |
| GB23663/71A GB1282076A (en) | 1970-03-13 | 1971-04-19 | N-vinyl-quinolones |
| US05/504,589 US3966743A (en) | 1968-07-23 | 1974-09-09 | Ortho fused cycloalkano-4-quinolone-3-carboxylic acid derivatives |
| US05/676,269 US4049811A (en) | 1968-07-23 | 1976-04-12 | Compositions using cycloalkano-quinolone derivatives and their method of use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2011885A DE2011885C3 (de) | 1970-03-13 | 1970-03-13 | 1,4-Dihydro-3-carboxy-cyclopentano (h)-chinolon-(4)-derivate, Verfahren zur Herstellung derselben und ihre Verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2011885A1 DE2011885A1 (de) | 1971-09-30 |
| DE2011885B2 DE2011885B2 (de) | 1980-08-07 |
| DE2011885C3 true DE2011885C3 (de) | 1981-05-21 |
Family
ID=5764939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2011885A Expired DE2011885C3 (de) | 1968-07-23 | 1970-03-13 | 1,4-Dihydro-3-carboxy-cyclopentano (h)-chinolon-(4)-derivate, Verfahren zur Herstellung derselben und ihre Verwendung |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS4835268B2 (enExample) |
| AT (2) | AT303734B (enExample) |
| BG (2) | BG18416A3 (enExample) |
| CA (1) | CA944355A (enExample) |
| CH (2) | CH558359A (enExample) |
| CS (2) | CS161899B2 (enExample) |
| DE (1) | DE2011885C3 (enExample) |
| DK (1) | DK129839B (enExample) |
| ES (1) | ES388909A1 (enExample) |
| FI (1) | FI49501C (enExample) |
| FR (1) | FR2085701B1 (enExample) |
| GB (1) | GB1282076A (enExample) |
| IE (1) | IE35111B1 (enExample) |
| IL (1) | IL36397A (enExample) |
| NL (1) | NL145854B (enExample) |
| PL (1) | PL82724B1 (enExample) |
| RO (2) | RO58367A (enExample) |
| SE (1) | SE361313B (enExample) |
| SU (2) | SU434653A3 (enExample) |
| ZA (1) | ZA711607B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3988460A (en) * | 1972-05-10 | 1976-10-26 | Boehringer Mannheim G.M.B.H. | Cyclopentenoquinolone compounds for treating bacterial infections |
| JPS50114345U (enExample) * | 1974-02-28 | 1975-09-18 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB830832A (en) * | 1957-02-15 | 1960-03-23 | Ici Ltd | New quinolones and therapeutic compositions containing them |
| CA944354A (en) * | 1968-07-23 | 1974-03-26 | Boehringer Mannheim G.M.B.H. | Cycloalkano-quinolone derivatives |
-
1970
- 1970-03-13 DE DE2011885A patent/DE2011885C3/de not_active Expired
-
1971
- 1971-02-08 SU SU1618801A patent/SU434653A3/ru active
- 1971-02-08 SU SU1747931A patent/SU436493A3/ru active
- 1971-03-04 BG BG018790A patent/BG18416A3/xx unknown
- 1971-03-04 ES ES388909A patent/ES388909A1/es not_active Expired
- 1971-03-04 BG BG016969A patent/BG18415A3/xx unknown
- 1971-03-10 CH CH550674A patent/CH558359A/xx not_active IP Right Cessation
- 1971-03-10 CH CH352771A patent/CH558358A/xx not_active IP Right Cessation
- 1971-03-10 DK DK112171AA patent/DK129839B/da unknown
- 1971-03-11 RO RO66229A patent/RO58367A/ro unknown
- 1971-03-11 IL IL36397A patent/IL36397A/xx unknown
- 1971-03-11 CS CS1805A patent/CS161899B2/cs unknown
- 1971-03-11 NL NL717103247A patent/NL145854B/xx unknown
- 1971-03-11 RO RO68915A patent/RO58563A/ro unknown
- 1971-03-11 ZA ZA711607A patent/ZA711607B/xx unknown
- 1971-03-11 CS CS5256*A patent/CS161900B2/cs unknown
- 1971-03-12 AT AT218371A patent/AT303734B/de not_active IP Right Cessation
- 1971-03-12 IE IE308/71A patent/IE35111B1/xx unknown
- 1971-03-12 FR FR7108638A patent/FR2085701B1/fr not_active Expired
- 1971-03-12 AT AT00541/72A patent/AT303735B/de not_active IP Right Cessation
- 1971-03-12 CA CA107,660A patent/CA944355A/en not_active Expired
- 1971-03-12 SE SE03194/71A patent/SE361313B/xx unknown
- 1971-03-12 PL PL1971146843A patent/PL82724B1/pl unknown
- 1971-03-12 FI FI710732A patent/FI49501C/fi active
- 1971-03-13 JP JP46014018A patent/JPS4835268B2/ja not_active Expired
- 1971-04-19 GB GB23663/71A patent/GB1282076A/en not_active Expired
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