GB804492A - Aminopyrine, caffeine or quinine hydrochloride inclusion compounds - Google Patents

Aminopyrine, caffeine or quinine hydrochloride inclusion compounds

Info

Publication number
GB804492A
GB804492A GB11890/55A GB1189055A GB804492A GB 804492 A GB804492 A GB 804492A GB 11890/55 A GB11890/55 A GB 11890/55A GB 1189055 A GB1189055 A GB 1189055A GB 804492 A GB804492 A GB 804492A
Authority
GB
United Kingdom
Prior art keywords
weight
urea
aminopyrine
parts
caffeine
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
Application number
GB11890/55A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB11890/55A priority Critical patent/GB804492A/en
Publication of GB804492A publication Critical patent/GB804492A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
    • C07D473/12—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1, 3, and 7, e.g. caffeine
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • C07D231/48—Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nanotechnology (AREA)
  • Biophysics (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Medical Informatics (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises a water-soluble inclusion compound obtained by heating aminopyrine (4 - dimethylamino - 1,5 - dimethyl - 2-phenyl-3-pyrazolone), caffeine or quinine hydrochloride with at least the stoichiometric amount of at least one carbamic acid alkyl ester and not more than 30 per cent, calculated on the weight of said ester, of an alkyl derivative of urea, and by heating aminopyrine or caffeine with at least the stoichiometric amount of at least one carbamic acid alkyl ester, and the preparation thereof by the said method. The addition compounds may be prepared by introducing the aminopyrine, caffeine or quinine hydrochloride into a melt of the carbamic acid ester, with or without the alkyl derivative of urea, and heating the mixture to 60-70 DEG C. The resulting melt may be solidified, dissolved and spray dried to form a powder. At least two of the compounds aminopyrine, caffeine and quinine hydrochloride may be introduced into the melt. The molar ratio of the aminopyrine, caffeine or quinine hydrochloride and the said complex-forming compounds may be adjusted to about 1 : 2. The above process may also be carried out by mixing an aqueous concentrated solution of the aminopyrine, caffeine or quinine hydrochloride with an aqueous concentrated solution of the carbamic acid ester, with or without the alkyl derivative of urea, and either substantially removing all the water under reduced pressure and heating the resulting mixture to 60 DEG to 70 DEG C., or substantially removing all the water at a temperature of about 60 DEG to 70 DEG C. Suitable alkyl methanes are methyl, ethyl and trichloroethyl methanes, and suitable alkyl derivatives of urea are monomethyl urea and sym. dimethyl urea. In the examples: (1) an inclusion compound is formed from ethyl methane and aminopyrine in a mol. ratio of 2 : 1 and has a melting point of 53 DEG C., and a solubility of 1 gm. in 1.5 cc. of water at 20 DEG C. and of 1 gm. in 1 cc. of water at 55 DEG C.; similar results are obtained if up to 30 per cent, e.g. from 5 to 30 per cent, by weight of the ethyl methane is replaced by an alkyl urea, e.g. a methyl urea; (2) an inclusion compound is prepared containing 230 parts by weight of aminopyrine, 40 parts by weight of caffeine and 178 parts by weight of methyl methane and has a melting point of 60 DEG C. and a solubility of 1 gm. in 1.5 cc. of water at 20 DEG C.; (3) an inclusion compound is prepared containing 60 parts by weight of quinine hydrochloride, 37 parts by weight of methyl methane and 3 parts by weight of ethyl urea (or N,N1-dimethyl urea) and has a melting point of 45 DEG C. and a solubility of 1 gm. in 2 gm. of water at about 35-40 DEG C.; and (4) an inclusion compound is prepared containing 49 parts by weight of ethyl methane, 3 parts by weight of N,N1-dimethyl urea, 10 parts by weight of caffeine and 38 parts by weight of aminopyrine and has a melting point of 55-56 DEG C. and a solubility of 1 part in 2 parts of water at about 35-40 DEG C.ALSO:Solutions having an antipyretic effect are prepared by dissolving in water, oils or fats the inclusion compound obtained by heating aminopyrine (4 - dimethylamino - 1,5 - dimethyl - 2-phenyl - 3 - pyrazolone) with at least the stoichiometric amount of at least one carbamic acid alkyl ester with or without not more than 30 per cent, calculated on the weight of said ester, of an alkyl derivative of urea. The solutions in oils and fats may be incorporated into suppositories.
GB11890/55A 1955-04-25 1955-04-25 Aminopyrine, caffeine or quinine hydrochloride inclusion compounds Expired GB804492A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB11890/55A GB804492A (en) 1955-04-25 1955-04-25 Aminopyrine, caffeine or quinine hydrochloride inclusion compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB11890/55A GB804492A (en) 1955-04-25 1955-04-25 Aminopyrine, caffeine or quinine hydrochloride inclusion compounds

Publications (1)

Publication Number Publication Date
GB804492A true GB804492A (en) 1958-11-19

Family

ID=11316954

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11890/55A Expired GB804492A (en) 1955-04-25 1955-04-25 Aminopyrine, caffeine or quinine hydrochloride inclusion compounds

Country Status (1)

Country Link
GB (1) GB804492A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2379283A1 (en) * 1977-02-05 1978-09-01 Henkel Kgaa COSMETIC PRODUCTS CONTAINING MOISTURIZING AGENTS FOR THE SKIN
EP0006724A1 (en) * 1978-06-16 1980-01-09 Phares Pharmaceutical Research N.V. Pharmaceutical compositions containing urea

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2379283A1 (en) * 1977-02-05 1978-09-01 Henkel Kgaa COSMETIC PRODUCTS CONTAINING MOISTURIZING AGENTS FOR THE SKIN
EP0006724A1 (en) * 1978-06-16 1980-01-09 Phares Pharmaceutical Research N.V. Pharmaceutical compositions containing urea
USRE32161E (en) * 1978-06-16 1986-05-27 Phares Pharmecutical Research N.V. Pharmaceutical compositions containing urea

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