GB708370A - Process for the production of scopolamine-bromobutylate - Google Patents

Process for the production of scopolamine-bromobutylate

Info

Publication number
GB708370A
GB708370A GB30023/51A GB3002351A GB708370A GB 708370 A GB708370 A GB 708370A GB 30023/51 A GB30023/51 A GB 30023/51A GB 3002351 A GB3002351 A GB 3002351A GB 708370 A GB708370 A GB 708370A
Authority
GB
United Kingdom
Prior art keywords
scopolamine
butylate
bromo
butyl bromide
months
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
GB30023/51A
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.)
ISLE LIEBRECHT
JULIUS LIEBRECHT
Original Assignee
ISLE LIEBRECHT
JULIUS LIEBRECHT
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 ISLE LIEBRECHT, JULIUS LIEBRECHT filed Critical ISLE LIEBRECHT
Publication of GB708370A publication Critical patent/GB708370A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms
    • C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (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)

Abstract

The invention comprises Scopolamine bromo-n-butylate, which may be prepared by reacting excess n-butyl bromide with scopolamine base in the presence of an organic solvent, preferably a highly polar solvent. The period of reaction is from several days at elevated temperatures to several months at ordinary temperatures. In examples (1) scopolamine is refluxed with aceto-nitrile and n-butyl bromide for 160 hours, solvent removed and scopolamine bromo-n-butylate crystallized from methanol; (2) scopolamine and n-butyl bromide in acetonitrile are allowed to stand for six months at room temperature, during which scopolamine bromo-n-butylate crystallizes. German Specification 698,274 is referred to.
GB30023/51A 1950-12-27 1951-12-21 Process for the production of scopolamine-bromobutylate Expired GB708370A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE708370X 1950-12-27

Publications (1)

Publication Number Publication Date
GB708370A true GB708370A (en) 1954-05-05

Family

ID=6617595

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30023/51A Expired GB708370A (en) 1950-12-27 1951-12-21 Process for the production of scopolamine-bromobutylate

Country Status (1)

Country Link
GB (1) GB708370A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5135933A (en) * 1989-05-25 1992-08-04 Fujisawa Pharmaceutical Company, Ltd. Method for transplantation of fertilized ova
US5973182A (en) * 1998-10-22 1999-10-26 Sepracor Inc. Carbonate Intermediates useful in the preparation of optically active cyclohexylphenylglycolate esters
US6140529A (en) * 1998-10-22 2000-10-31 Sepracor Inc. Synthesis of optically active cyclohexylphenylglycolate esters

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5135933A (en) * 1989-05-25 1992-08-04 Fujisawa Pharmaceutical Company, Ltd. Method for transplantation of fertilized ova
US5973182A (en) * 1998-10-22 1999-10-26 Sepracor Inc. Carbonate Intermediates useful in the preparation of optically active cyclohexylphenylglycolate esters
US6090971A (en) * 1998-10-22 2000-07-18 Sepracor Inc. Resolution process for cyclohexylphenyl glycolic acid
US6140529A (en) * 1998-10-22 2000-10-31 Sepracor Inc. Synthesis of optically active cyclohexylphenylglycolate esters

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