DE2555158A1 - Alpha-(tolyloxycarbonyl)-3-thienylmethylpenicillin, verfahren zu seiner herstellung und diese verbindung enthaltende arzneipraeparate - Google Patents
Alpha-(tolyloxycarbonyl)-3-thienylmethylpenicillin, verfahren zu seiner herstellung und diese verbindung enthaltende arzneipraeparateInfo
- Publication number
- DE2555158A1 DE2555158A1 DE19752555158 DE2555158A DE2555158A1 DE 2555158 A1 DE2555158 A1 DE 2555158A1 DE 19752555158 DE19752555158 DE 19752555158 DE 2555158 A DE2555158 A DE 2555158A DE 2555158 A1 DE2555158 A1 DE 2555158A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- acid
- compound
- acylating derivative
- solution
- 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
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- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 229940126601 medicinal product Drugs 0.000 title 1
- -1 p-Tolyloxycarbonyl Chemical group 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
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- 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 12
- 229930182555 Penicillin Natural products 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 229940049954 penicillin Drugs 0.000 claims description 10
- 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 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 238000003776 cleavage reaction Methods 0.000 claims description 4
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- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 238000006136 alcoholysis reaction Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 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
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate 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
- 230000000069 prophylactic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- AXZPMKATFNMZNE-UHFFFAOYSA-M sodium;3-ethylheptanoate Chemical compound [Na+].CCCCC(CC)CC([O-])=O AXZPMKATFNMZNE-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 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 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB818675A GB1455529A (enrdf_load_stackoverflow) | 1975-02-27 | 1975-02-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2555158A1 true DE2555158A1 (de) | 1976-09-09 |
Family
ID=9847499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752555158 Pending DE2555158A1 (de) | 1975-02-27 | 1975-12-08 | Alpha-(tolyloxycarbonyl)-3-thienylmethylpenicillin, verfahren zu seiner herstellung und diese verbindung enthaltende arzneipraeparate |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS51101993A (enrdf_load_stackoverflow) |
| AU (1) | AU1146276A (enrdf_load_stackoverflow) |
| BE (1) | BE839058A (enrdf_load_stackoverflow) |
| CA (1) | CA1047484A (enrdf_load_stackoverflow) |
| DE (1) | DE2555158A1 (enrdf_load_stackoverflow) |
| ES (1) | ES445577A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1455529A (enrdf_load_stackoverflow) |
| ZA (1) | ZA757369B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ194912A (en) | 1979-10-02 | 1983-05-31 | Beecham Group Ltd | 6 -(2-(2'-methylphenoxycarbonyl)-2-thien-3'-ylacetamido)-penicillanic acid and pharmaceutical compositions |
-
1975
- 1975-02-27 GB GB818675A patent/GB1455529A/en not_active Expired
- 1975-05-29 CA CA228,020A patent/CA1047484A/en not_active Expired
- 1975-11-24 ZA ZA757369A patent/ZA757369B/xx unknown
- 1975-12-08 DE DE19752555158 patent/DE2555158A1/de active Pending
-
1976
- 1976-02-04 JP JP51011179A patent/JPS51101993A/ja active Pending
- 1976-02-26 ES ES445577A patent/ES445577A1/es not_active Expired
- 1976-02-26 AU AU11462/76A patent/AU1146276A/en not_active Expired
- 1976-02-27 BE BE164751A patent/BE839058A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES445577A1 (es) | 1977-11-01 |
| AU1146276A (en) | 1977-09-01 |
| GB1455529A (enrdf_load_stackoverflow) | 1976-11-10 |
| JPS51101993A (enrdf_load_stackoverflow) | 1976-09-08 |
| CA1047484A (en) | 1979-01-30 |
| BE839058A (fr) | 1976-08-27 |
| ZA757369B (en) | 1976-11-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |