DE2116900A1 - Verfahren zum Herstellen von Salzen des alpha Ammobenzylpenicillins - Google Patents
Verfahren zum Herstellen von Salzen des alpha AmmobenzylpenicillinsInfo
- Publication number
- DE2116900A1 DE2116900A1 DE19712116900 DE2116900A DE2116900A1 DE 2116900 A1 DE2116900 A1 DE 2116900A1 DE 19712116900 DE19712116900 DE 19712116900 DE 2116900 A DE2116900 A DE 2116900A DE 2116900 A1 DE2116900 A1 DE 2116900A1
- Authority
- DE
- Germany
- Prior art keywords
- aminobenzylpenicillin
- salts
- aqueous
- organic
- preparation
- 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
- 150000003839 salts Chemical class 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 8
- VEAOYIMEHYDQHN-UHFFFAOYSA-N (2-methoxyphenyl) 2-hydroxyacetate Chemical compound COC1=CC=CC=C1OC(=O)CO VEAOYIMEHYDQHN-UHFFFAOYSA-N 0.000 claims description 19
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 11
- -1 thionylamino Chemical group 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 2
- 229960001867 guaiacol Drugs 0.000 claims 2
- AUZQQIPZESHNMG-UHFFFAOYSA-N 3-methoxysalicylic acid Chemical compound COC1=CC=CC(C(O)=O)=C1O AUZQQIPZESHNMG-UHFFFAOYSA-N 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YJESALUAHUVISI-UHFFFAOYSA-N 3,5-dimethylhexan-2-one Chemical compound CC(C)CC(C)C(C)=O YJESALUAHUVISI-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CACOOQBHODXMRK-UHFFFAOYSA-N (2-methoxyphenyl) 2-(diethylamino)acetate Chemical class CCN(CC)CC(=O)OC1=CC=CC=C1OC CACOOQBHODXMRK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- OSOVNLTXXLKBQC-UHFFFAOYSA-N 2-methoxyphenol;sulfuric acid Chemical compound OS(O)(=O)=O.COC1=CC=CC=C1O OSOVNLTXXLKBQC-UHFFFAOYSA-N 0.000 description 1
- QDRCGSIKAHSALR-UHFFFAOYSA-N 4-hydroxy-3-methoxybenzene-1-sulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=CC=C1O QDRCGSIKAHSALR-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
- 101100128278 Mus musculus Lins1 gene Proteins 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000002152 aqueous-organic solution Substances 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960003360 guaiacolsulfonate Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES378410A ES378410A1 (es) | 1970-04-09 | 1970-04-09 | Procedimiento de obtencion de sales de la alfa-aminobencil-penicilina. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2116900A1 true DE2116900A1 (de) | 1971-10-21 |
Family
ID=8455582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712116900 Pending DE2116900A1 (de) | 1970-04-09 | 1971-04-07 | Verfahren zum Herstellen von Salzen des alpha Ammobenzylpenicillins |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4825485B1 (enExample) |
| AR (1) | AR195367A1 (enExample) |
| BE (1) | BE753220A (enExample) |
| CH (1) | CH530419A (enExample) |
| DE (1) | DE2116900A1 (enExample) |
| ES (1) | ES378410A1 (enExample) |
| FR (1) | FR2085939A1 (enExample) |
| GB (1) | GB1320406A (enExample) |
-
1970
- 1970-04-09 ES ES378410A patent/ES378410A1/es not_active Expired
- 1970-06-09 FR FR7021088A patent/FR2085939A1/fr not_active Withdrawn
- 1970-06-29 GB GB3130770A patent/GB1320406A/en not_active Expired
- 1970-07-09 BE BE753220D patent/BE753220A/xx unknown
- 1970-07-16 CH CH1080870A patent/CH530419A/fr not_active IP Right Cessation
- 1970-11-20 AR AR232522A patent/AR195367A1/es active
- 1970-12-14 JP JP45111054A patent/JPS4825485B1/ja active Pending
-
1971
- 1971-04-07 DE DE19712116900 patent/DE2116900A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4825485B1 (enExample) | 1973-07-30 |
| BE753220A (fr) | 1970-12-16 |
| FR2085939A1 (enExample) | 1971-12-31 |
| ES378410A1 (es) | 1973-03-16 |
| CH530419A (fr) | 1972-11-15 |
| GB1320406A (en) | 1973-06-13 |
| AR195367A1 (es) | 1973-10-08 |
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