DE2205169C3 - Verfahren zur Reinigung von 6-[D-α-(3-Guanyl-1-ureido)-phenylacetamido]-penicillansäure - Google Patents
Verfahren zur Reinigung von 6-[D-α-(3-Guanyl-1-ureido)-phenylacetamido]-penicillansäureInfo
- Publication number
- DE2205169C3 DE2205169C3 DE2205169A DE2205169A DE2205169C3 DE 2205169 C3 DE2205169 C3 DE 2205169C3 DE 2205169 A DE2205169 A DE 2205169A DE 2205169 A DE2205169 A DE 2205169A DE 2205169 C3 DE2205169 C3 DE 2205169C3
- Authority
- DE
- Germany
- Prior art keywords
- guanyl
- ureido
- phenylacetamido
- penicillanic acid
- crystalline
- 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 claims description 8
- 238000000746 purification Methods 0.000 title claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 26
- 239000002244 precipitate Substances 0.000 claims description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
- 229910017604 nitric acid Inorganic materials 0.000 claims description 5
- FGHSTPNOXKDLKU-UHFFFAOYSA-N nitric acid;hydrate Chemical compound O.O[N+]([O-])=O FGHSTPNOXKDLKU-UHFFFAOYSA-N 0.000 claims description 5
- 229910002651 NO3 Inorganic materials 0.000 claims description 4
- 239000002002 slurry Substances 0.000 claims description 4
- 150000002823 nitrates Chemical class 0.000 claims description 3
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 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
- 150000004682 monohydrates Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- CRDUMFPZOLIQCX-UHFFFAOYSA-N 1-amino-3-(diaminomethylidene)urea;dihydrochloride Chemical compound Cl.Cl.NNC(=O)N=C(N)N CRDUMFPZOLIQCX-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000002253 acid Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 229960000723 ampicillin Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QHNCQQJOCQZXFW-UHFFFAOYSA-N 1-(diaminomethylidene)-3-nitrourea Chemical compound NC(N)=NC(=O)N[N+]([O-])=O QHNCQQJOCQZXFW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 benzal Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 238000007705 chemical test Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960003311 ampicillin trihydrate Drugs 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 230000002252 carbamoylating effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance 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
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 |
|---|---|---|---|
| US11245271A | 1971-02-03 | 1971-02-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2205169A1 DE2205169A1 (de) | 1972-08-17 |
| DE2205169B2 DE2205169B2 (de) | 1980-09-04 |
| DE2205169C3 true DE2205169C3 (de) | 1981-05-07 |
Family
ID=22343981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2205169A Expired DE2205169C3 (de) | 1971-02-03 | 1972-02-03 | Verfahren zur Reinigung von 6-[D-α-(3-Guanyl-1-ureido)-phenylacetamido]-penicillansäure |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3711471A (OSRAM) |
| JP (1) | JPS5231880B1 (OSRAM) |
| AU (1) | AU459026B2 (OSRAM) |
| BE (1) | BE778944A (OSRAM) |
| CA (1) | CA986505A (OSRAM) |
| DE (1) | DE2205169C3 (OSRAM) |
| FR (1) | FR2124411B1 (OSRAM) |
| GB (1) | GB1382276A (OSRAM) |
| ZA (1) | ZA72609B (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933797A (en) * | 1972-02-22 | 1976-01-20 | Pfizer Inc. | 6-[α-(ω-QUANIDINOALKANOYLAMIDO)ACYLAMIDO]PENICILLANIC ACIDS |
| AR204162A1 (es) * | 1972-05-08 | 1975-11-28 | Yamanouchi Pharma Co Ltd | Proceso para la preparacion de derivados de ampicilina |
| US3891627A (en) * | 1972-05-18 | 1975-06-24 | Pfizer | 6-{8 Alpha-(amidinothioacylamido)acylamido{9 penicillanic acids |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU33875B (en) * | 1968-12-02 | 1978-06-30 | Bristol Myers Co | Process for preparing antibacterial agents |
| US3579501A (en) * | 1969-08-22 | 1971-05-18 | Bristol Myers Co | 6-(alpha-(3 - guanyl - 1 - ureido)phenyl- or thienyl-acetamido)penicillanic acids |
-
1971
- 1971-02-03 US US00112452A patent/US3711471A/en not_active Expired - Lifetime
-
1972
- 1972-01-12 CA CA132234A patent/CA986505A/en not_active Expired
- 1972-01-25 AU AU38290/72A patent/AU459026B2/en not_active Expired
- 1972-01-31 ZA ZA720609A patent/ZA72609B/xx unknown
- 1972-02-01 GB GB474372A patent/GB1382276A/en not_active Expired
- 1972-02-02 FR FR7203520A patent/FR2124411B1/fr not_active Expired
- 1972-02-03 DE DE2205169A patent/DE2205169C3/de not_active Expired
- 1972-02-03 JP JP47011889A patent/JPS5231880B1/ja active Pending
- 1972-02-03 BE BE778944A patent/BE778944A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA986505A (en) | 1976-03-30 |
| ZA72609B (en) | 1972-10-25 |
| FR2124411A1 (OSRAM) | 1972-09-22 |
| BE778944A (fr) | 1972-08-03 |
| DE2205169B2 (de) | 1980-09-04 |
| AU3829072A (en) | 1973-07-26 |
| FR2124411B1 (OSRAM) | 1975-10-10 |
| JPS5231880B1 (OSRAM) | 1977-08-17 |
| US3711471A (en) | 1973-01-16 |
| AU459026B2 (en) | 1975-03-13 |
| DE2205169A1 (de) | 1972-08-17 |
| GB1382276A (en) | 1975-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: KINZEBACH, W., DIPL.-CHEM. DR.PHIL., PAT.-ANW., 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |