IE43950L - 6-amidinopenicillanic acid derivatives - Google Patents

6-amidinopenicillanic acid derivatives

Info

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
Application number
IE762191A
Other versions
IE43950B1 (en
Original Assignee
Leo Pharm Prod Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Leo Pharm Prod Ltd filed Critical Leo Pharm Prod Ltd
Publication of IE43950L publication Critical patent/IE43950L/en
Publication of IE43950B1 publication Critical patent/IE43950B1/en

Links

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]
IE2191/76A 1975-10-29 1976-10-05 New 6-amidinopenicillanic acid derivatives IE43950B1 (en)

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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1427139A (en) * 1972-03-13 1976-03-10 Astra Laekemedel Ab Penicillins

Also Published As

Publication number Publication date
JPS5257190A (en) 1977-05-11
GB1529448A (en) 1978-10-18
AU501771B2 (en) 1979-06-28
BE847749A (en) 1977-04-28
ZA766165B (en) 1977-09-28
FR2329287A1 (en) 1977-05-27
AU1867376A (en) 1978-04-20
IE43950B1 (en) 1981-07-01
DE2649183A1 (en) 1977-05-12
NZ182323A (en) 1984-07-31
FR2329287B1 (en) 1979-03-02

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