IE43950L - 6-amidinopenicillanic acid derivatives - Google Patents
6-amidinopenicillanic acid derivativesInfo
- Publication number
- IE43950L IE43950L IE762191A IE219176A IE43950L IE 43950 L IE43950 L IE 43950L IE 762191 A IE762191 A IE 762191A IE 219176 A IE219176 A IE 219176A IE 43950 L IE43950 L IE 43950L
- Authority
- IE
- Ireland
- Prior art keywords
- hydrochloride
- treating
- diastereomeric
- ethoxycarbonyloxyethyl
- base
- Prior art date
Links
- 239000002253 acid Substances 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 239000002585 base Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 abstract 2
- 238000001704 evaporation Methods 0.000 abstract 2
- 239000012458 free base Substances 0.000 abstract 2
- 239000012452 mother liquor Substances 0.000 abstract 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- YVRGKFXJZCTTRB-UHFFFAOYSA-N 1-chloroethyl ethyl carbonate Chemical compound CCOC(=O)OC(C)Cl YVRGKFXJZCTTRB-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- AIPVTTKYSPOWFO-UHFFFAOYSA-N azepane-1-carbaldehyde Chemical compound O=CN1CCCCCC1 AIPVTTKYSPOWFO-UHFFFAOYSA-N 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000004108 freeze drying Methods 0.000 abstract 1
- -1 hexahydro- 1H - azepin - 1 - yl - methyleneamino Chemical group 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 229940127557 pharmaceutical product Drugs 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (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)
Abstract
1529448 1<SP>1</SP>-Ethoxycarbonyloxy-ethyl 6-(hexahydro-1H-azepin-1-yl-methyleneamino)-penicillanate LEO PHARMACEUTICAL PRODUCTS Ltd AS 8 Oct 1976 [29 Oct 1975] 44676/75 Heading C2C [Also in Division A5] Novel crystalline diastereomeric forms of 1<SP>1</SP> - ethoxycarbonyloxyethyl - 6 - (hexahydro- 1H - azepin - 1 - yl - methyleneamino) - penicillenate or its hydrochloride are prepared (a) by adding an equivalent of HCl in propanol- 2 to an ethereal solution of mixture of the free base forms, treating the isolated crystals with acetone and recrystallizing them from methanolether to give one diastereomeric hydrochloride, and evaporating the mother liquor and treating the residue with methanol-ether or propanol-2- diisopropyl ether to crystallize the other diastereomeric hydrochloride; or (b) by dissolving the free base in ether, adding cold water, adjusting to pH3À0 with NHCl, freeze-drying the aqueous phase, treating the amorphous mixture with acetone to crystallize one diastereomeric hydrochloride, evaporating the mother liquor, treating the residue with aqueous NaHCO 3 , purifying the liberated base with an ionexchange resin, converting it to the hydrochloride and crystallizing it from ethyl acetate to give the other diastereomeric hydrochloride; or (c) by neutralizing an aqueous solution of the diastereomeric hydrochloride with a base, such as NaHCO 3 to crystallize the diastereomeric base. 1<SP>1</SP>-Ethoxycarbonyloxyethyl 6-(hexahydro-1H- azepin-1-yl-methyleneamino)-penicillinate is prepared as an amorphous mixture of diastereomers by reacting potassium benzylpenicillanate with 1-chloroethylethyl carbonate, treating the resulting 1<SP>1</SP>-ethoxycarbonyloxyethyl benzylpenicillanate with phosphorus pentachloride and quinoline in chloroform, and treating the resulting 1<SP>1</SP>-ethoxycarbonyloxyethyl 6-amino-penicillanate with the dimethyl sulphate complex of N-formyl-hexamethyleneimine.
[GB1529448A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB44676/75A GB1529448A (en) | 1975-10-29 | 1975-10-29 | 6-amidinopenicillanic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43950L true IE43950L (en) | 1977-04-29 |
| IE43950B1 IE43950B1 (en) | 1981-07-01 |
Family
ID=10434309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2191/76A IE43950B1 (en) | 1975-10-29 | 1976-10-05 | New 6-amidinopenicillanic acid derivatives |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5257190A (en) |
| AU (1) | AU501771B2 (en) |
| BE (1) | BE847749A (en) |
| DE (1) | DE2649183A1 (en) |
| FR (1) | FR2329287A1 (en) |
| GB (1) | GB1529448A (en) |
| IE (1) | IE43950B1 (en) |
| NZ (1) | NZ182323A (en) |
| ZA (1) | ZA766165B (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1427139A (en) * | 1972-03-13 | 1976-03-10 | Astra Laekemedel Ab | Penicillins |
-
1975
- 1975-10-29 GB GB44676/75A patent/GB1529448A/en not_active Expired
-
1976
- 1976-10-05 IE IE2191/76A patent/IE43950B1/en unknown
- 1976-10-13 NZ NZ182323A patent/NZ182323A/en unknown
- 1976-10-14 AU AU18673/76A patent/AU501771B2/en not_active Expired
- 1976-10-15 ZA ZA766165A patent/ZA766165B/en unknown
- 1976-10-27 FR FR7632412A patent/FR2329287A1/en active Granted
- 1976-10-27 JP JP51128415A patent/JPS5257190A/en active Pending
- 1976-10-28 DE DE19762649183 patent/DE2649183A1/en not_active Ceased
- 1976-10-28 BE BE171883A patent/BE847749A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE43950B1 (en) | 1981-07-01 |
| JPS5257190A (en) | 1977-05-11 |
| NZ182323A (en) | 1984-07-31 |
| GB1529448A (en) | 1978-10-18 |
| BE847749A (en) | 1977-04-28 |
| AU1867376A (en) | 1978-04-20 |
| DE2649183A1 (en) | 1977-05-12 |
| AU501771B2 (en) | 1979-06-28 |
| FR2329287B1 (en) | 1979-03-02 |
| ZA766165B (en) | 1977-09-28 |
| FR2329287A1 (en) | 1977-05-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE802658L (en) | Crystalline sweetener | |
| US3240775A (en) | Preparation of alpha-l-fucosides and l-fucose from fucoidan | |
| COXON et al. | Simplified preparation of sophorose (2-O-β-D-glucopyranosyl-D-glucose) | |
| IE43950L (en) | 6-amidinopenicillanic acid derivatives | |
| US3539550A (en) | Process for the preparation of 2'-halo-2'-deoxy pyrimidine nucleosides | |
| GB1452452A (en) | Manufacture of optically active-p-hydroxyphenylglycine and salts thereof | |
| US2993833A (en) | Erythromycin esters | |
| US4282161A (en) | Novel purification process | |
| US4910222A (en) | Cysteine derivatives having expectorant activity | |
| Ness et al. | The Reduction of Various Sugar Acids to Glycitols with Lithium Aluminum Hydride | |
| US2813871A (en) | O-syringoyl reserpic acid esters | |
| Frush et al. | Amides of glucuronic, galacturonic, and mannuronic acids | |
| JPS55167267A (en) | Purification of alpha-l-aspartyl-l-phenylalanine lower alkyl ester | |
| US2991307A (en) | Process of resolving nu, nu-dibenzyl-dl-alpha-amino acids and products | |
| US3322771A (en) | Intermediates for preparing thebaine derivatives | |
| Wolfrom et al. | Thioglycosides of 3-Amino-3-deoxy-D-mannose1 | |
| US2832719A (en) | Nystatin purification | |
| US2380444A (en) | Chemical process and products | |
| US2013536A (en) | Acetyl choline acetate | |
| US3109003A (en) | Lower alkyl reserpate-18-[alpha-methyl-beta-(3, 4, 5-trimethoxyphenyl)]-acrylate | |
| KR970042564A (en) | High-density, highly crystalline Ceperazone sodium salt and preparation method thereof | |
| IL26522A (en) | Preparation of 4'-demethyl-epipodophyllotoxin | |
| IL33548A (en) | Galactopyranosides as lincomycin intermediates | |
| US3284489A (en) | Calcium mono-glycine acetylsalicylate | |
| JPS6426579A (en) | Production of guanine crystal |