DE2256538C2 - Probenecidsalz des Pivaloyloxymethylesters von D-(-)-α-Aminobenzylpenicillin, seine Herstellung und diese enthaltende pharmazeutische Mittel - Google Patents
Probenecidsalz des Pivaloyloxymethylesters von D-(-)-α-Aminobenzylpenicillin, seine Herstellung und diese enthaltende pharmazeutische MittelInfo
- Publication number
- DE2256538C2 DE2256538C2 DE2256538A DE2256538A DE2256538C2 DE 2256538 C2 DE2256538 C2 DE 2256538C2 DE 2256538 A DE2256538 A DE 2256538A DE 2256538 A DE2256538 A DE 2256538A DE 2256538 C2 DE2256538 C2 DE 2256538C2
- Authority
- DE
- Germany
- Prior art keywords
- salt
- probenecid
- pivaloyloxymethyl ester
- aminobenzylpenicillin
- ester
- 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
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical class CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 title claims description 21
- -1 pivaloyloxymethyl ester Chemical class 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- AVKUERGKIZMTKX-YXLKDIQASA-N (2s,5r)-6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)NC(=O)C(N)C1=CC=CC=C1 AVKUERGKIZMTKX-YXLKDIQASA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 11
- 229930182555 Penicillin Natural products 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- 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 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000008177 pharmaceutical agent Substances 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 239000011872 intimate mixture Substances 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 235000019371 penicillin G benzathine Nutrition 0.000 claims 1
- 229940056360 penicillin g Drugs 0.000 claims 1
- 150000002960 penicillins Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- 239000000203 mixture Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 239000003242 anti bacterial agent Substances 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 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 6
- 239000002775 capsule Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 229940049954 penicillin Drugs 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229960000723 ampicillin Drugs 0.000 description 4
- 235000019658 bitter taste Nutrition 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229960003081 probenecid Drugs 0.000 description 3
- 229960004793 sucrose Drugs 0.000 description 3
- 235000019640 taste Nutrition 0.000 description 3
- 230000009967 tasteless effect Effects 0.000 description 3
- 241000220479 Acacia Species 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000036765 blood level Effects 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
- WLDHEUZGFKACJH-ZRUFZDNISA-K Amaranth Chemical compound [Na+].[Na+].[Na+].C12=CC=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C1\N=N\C1=CC=C(S([O-])(=O)=O)C2=CC=CC=C12 WLDHEUZGFKACJH-ZRUFZDNISA-K 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 125000005042 acyloxymethyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007958 cherry flavor Substances 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 229940068682 chewable tablet Drugs 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000002864 food coloring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- YTGKHEDTLHRZGX-RWSKJCERSA-N n-(cyclopentylmethyl)-n-[(2s)-3-[(3s,5r)-3,5-dibenzyl-2-oxopyrrolidin-1-yl]-2-hydroxypropyl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(CC1CCCC1)C[C@@H](O)CN1C(=O)[C@@H](CC=2C=CC=CC=2)C[C@@H]1CC1=CC=CC=C1 YTGKHEDTLHRZGX-RWSKJCERSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 230000014860 sensory perception of taste Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20014871A | 1971-11-18 | 1971-11-18 | |
| US27841572A | 1972-08-07 | 1972-08-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2256538A1 DE2256538A1 (de) | 1973-05-24 |
| DE2256538C2 true DE2256538C2 (de) | 1981-10-08 |
Family
ID=26895526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2256538A Expired DE2256538C2 (de) | 1971-11-18 | 1972-11-17 | Probenecidsalz des Pivaloyloxymethylesters von D-(-)-α-Aminobenzylpenicillin, seine Herstellung und diese enthaltende pharmazeutische Mittel |
Country Status (15)
-
0
- BE BE791532D patent/BE791532A/xx unknown
-
1972
- 1972-09-26 DK DK474372AA patent/DK137607B/da not_active IP Right Cessation
- 1972-10-30 NL NL7214681A patent/NL7214681A/xx not_active Application Discontinuation
- 1972-11-06 IL IL40752A patent/IL40752A0/xx unknown
- 1972-11-07 AU AU48598/72A patent/AU4859872A/en not_active Expired
- 1972-11-13 GB GB5237472A patent/GB1365028A/en not_active Expired
- 1972-11-13 ZM ZM178/72A patent/ZM17872A1/xx unknown
- 1972-11-15 CH CH1662172A patent/CH575953A5/xx not_active IP Right Cessation
- 1972-11-15 OA OA54748A patent/OA04273A/xx unknown
- 1972-11-15 DD DD166871A patent/DD100262A5/xx unknown
- 1972-11-16 LU LU66486A patent/LU66486A1/xx unknown
- 1972-11-16 AR AR245171A patent/AR195888A1/es active
- 1972-11-17 DE DE2256538A patent/DE2256538C2/de not_active Expired
- 1972-11-17 FR FR7241016A patent/FR2160653B1/fr not_active Expired
- 1972-11-18 JP JP11610672A patent/JPS5516436B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5516436B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-05-01 |
| FR2160653B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-05-21 |
| NL7214681A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-05-22 |
| OA04273A (fr) | 1979-12-31 |
| DK137607B (da) | 1978-04-03 |
| GB1365028A (en) | 1974-08-29 |
| JPS4861612A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-08-29 |
| ZM17872A1 (en) | 1974-09-23 |
| AU4859872A (en) | 1974-05-09 |
| DD100262A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-09-12 |
| LU66486A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-06-08 |
| FR2160653A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-06-29 |
| BE791532A (fr) | 1973-05-17 |
| CH575953A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-05-31 |
| AR195888A1 (es) | 1973-11-15 |
| DK137607C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-10-02 |
| DE2256538A1 (de) | 1973-05-24 |
| IL40752A0 (en) | 1973-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |