GB576340A - Improvements in or relating to the manufacture of amine carbonates and to inhalant preparations containing the same - Google Patents

Improvements in or relating to the manufacture of amine carbonates and to inhalant preparations containing the same

Info

Publication number
GB576340A
GB576340A GB563/44A GB56344A GB576340A GB 576340 A GB576340 A GB 576340A GB 563/44 A GB563/44 A GB 563/44A GB 56344 A GB56344 A GB 56344A GB 576340 A GB576340 A GB 576340A
Authority
GB
United Kingdom
Prior art keywords
oil
amino
amine
carbon dioxide
menthol
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
GB563/44A
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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 Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB576340A publication Critical patent/GB576340A/en
Expired legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/007Pulmonary tract; Aromatherapy

Landscapes

  • Health & Medical Sciences (AREA)
  • Pulmonology (AREA)
  • Chemical & Material Sciences (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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Carbonates of 1-R-1 amino ethanes, where R is a saturated aliphatic hydrocarbon radical having from 4 to 9 carbon atoms are prepared by reacting the amine with carbon dioxide and water, preferably in the proportions of one-half molecular equivalent each per mole. of amine. The normal carbonate is the main reaction product. These amine carbonates may be used in inhalers as vasoconstrictors (see Group VI). The process may be carried out as follows: (1) by passing dry carbon dioxide through a mixture of the amine and water in the above proportions until a one-half molar quantity of the carbon dioxide has been taken up; (2) by passing moist carbon dioxide through the dry amine until the increase in weight corresponds to absorption of the above-stated equivalents of carbon dioxide and water; (3) by passing moist carbon dioxide into a dry solution of the amine in a volatile solvent such as ether until the theoretical increase in weight has occurred as in (2) and then carefully removing the solvent by evaporation; (4) by passing moist carbon dioxide into a solution of moist amine in an oil base such as mineral oil, cottonseed oil, or olive oil with the addition of an essential oil which facilitates said solution, such as menthol, camphor, oil of lavender or oil of rose; alternatively, in this method either the amine or carbon dioxide may be dry, but at least one of them should contain sufficient moisture for the production of the carbonate which is determined by the weight increase as above. The reaction temperature is desirably maintained below 30 DEG C. The amino ethanes employed as starting materials and their preparations are described in Specifications 4076/43, 4446/43, 575,677 and 576,943 (as open to public inspection under Sect. 91). Examples describe the preparation of (1) 2-aminoheptane carbonate by method 1; (2) the same carbonate by method 3; (3) and (4) the carbonates of 2-amino-4-methyl hexane and 2-amino-4-methyl heptane by method 1; (5) 2-amino heptane carbonate by passing dry carbon dioxide into a solution of the amine, water, menthol, oil of rose, and paraffin oil; (6) 2-amino-4-methyl hexane carbonate by passing dry carbon dioxide into a mixture comprising the amine, water, menthol, oil of lavender, and cottonseed oil; and (7) 2-amino-4-methyl heptane carbonate by passing dry carbon dioxide into a solution of the amine, water, menthol, camphor, oil of rose geranium and ethyl oleate. In examples 5, 6 and 7, peanut oil or lauryl alcohol may replace the oil base used. In place of menthol and the essential oils, there may be used phenylethyl alcohol, oil of thyme and oil of cedar. The Specification as open to inspection under Sect. 91 states that the starting materials may also comprise 1-R-1 amino ethanes, where R is an unsaturated aliphatic hydrocarbon radical having 4 to 9 carbon atoms; thus the 2-amino heptane used in the above examples may be replaced by 2-amino heptene or 2-amino-heptine. This subject-matter does not appear in the Specification as accepted.ALSO:Carbonates I-R-I-amino ethanes where R represents a saturated aliphatic hydrocarbon of 4 to 9 carbon atoms (see Group IV) may be used as vasoconstrictors in inhalers. They may be used as such but are preferably employed in solution in oil bases, such as liquid petrolatum, certain vegetable oils such as cottonseed oil, and esters of fatty acids such as ethyl oleate. Desirably an essential oil which facilitates the solution of such as menthol, camphor, oil of lavender, or oil of rose, may be present. In examples are described (1) amine carbonates of 2-aminoheptane, 2-amino-4-methylhexane, and 2-amino-4-methylheptane, all being suitable as inhalers; (2) an inhalant preparation comprising 2-aminoheptane carbonate, menthol, oil of rose and paraffin oil which may be used on cotton pledgets; (3) an inhalant mixture comprising 2-amino-4-methylhexane carbonate, menthol, oil of lavender and cottonseed oil; and (4) an inhalant mixture comprising 2-amino-4-methyl heptane carbonate, menthol, camphor, oil of rose geranium and ethyl oleate. The oil bases may be replaced by peanut oil or lauryl alcohol, while instead of menthol and the above mentioned essential oils, there may be used in phenylethyl alcohol, oil of thyme, and oil of cedar. The parent amines are described in Specifications 575,677, 576,943, 4076/43 and 4446/43 (as open to inspection under Section 91). The Specification as open to inspection under Section 91 includes also the use of 2-amino alkenes and 2-amino alkines, being I-R-I-aminoethanes where R is an unsaturated aliphatic hydrocarbon radical having 4 to 9 carbon atoms; thus the 2-amino heptane used above may be replaced by 2-amino heptene or 2-amino heptine. This subject matter does not appear in the Specification as accepted.
GB563/44A 1943-01-15 1944-01-12 Improvements in or relating to the manufacture of amine carbonates and to inhalant preparations containing the same Expired GB576340A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US576340XA 1943-01-15 1943-01-15

Publications (1)

Publication Number Publication Date
GB576340A true GB576340A (en) 1946-03-29

Family

ID=22011827

Family Applications (1)

Application Number Title Priority Date Filing Date
GB563/44A Expired GB576340A (en) 1943-01-15 1944-01-12 Improvements in or relating to the manufacture of amine carbonates and to inhalant preparations containing the same

Country Status (1)

Country Link
GB (1) GB576340A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4483888A (en) * 1981-09-01 1984-11-20 Phillips Petroleum Company Carbon dioxide treatment of epoxy resin compositions
US4526721A (en) * 1982-06-28 1985-07-02 Thomas Swan & Co. Ltd. Curing of epoxide resins
EP2868314A1 (en) * 2013-10-31 2015-05-06 AromaStick AG Composition for use in an inhalation device and inhalation device that can be used for same

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4483888A (en) * 1981-09-01 1984-11-20 Phillips Petroleum Company Carbon dioxide treatment of epoxy resin compositions
US4526721A (en) * 1982-06-28 1985-07-02 Thomas Swan & Co. Ltd. Curing of epoxide resins
EP2868314A1 (en) * 2013-10-31 2015-05-06 AromaStick AG Composition for use in an inhalation device and inhalation device that can be used for same
WO2015062684A1 (en) * 2013-10-31 2015-05-07 Aromastick Ag Composition for use in an inhalation device and inhalation device useful therefor

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