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(3S,4S)-delta-6-tetrahydrocannabinol-7-oic acids and derivatives thereof, processors for their preparation and pharmaceutical compositions containing them

Patent 5635530 Issued on June 3, 1997. Estimated Expiration Date: Icon_subject June 3, 2014. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.

Patent References

Novel tetrahydrocannabinol type compounds
Patent #: 4179517
Issued on: 12/18/1979
Inventor: Mechoulam ,   et al.

Delta 1-thc-7-oic acid and analgesic and anti-inflammatory agents
Patent #: 4847290
Issued on: 07/11/1989
Inventor: Burstein

(3S-4S)-7-hydroxy-Ɗ6 -tetrahydrocannabinols
Patent #: 4876276
Issued on: 10/24/1989
Inventor: Mechoulam, et al.

Platelet activating factor antagonist and methods of use therefor
Patent #: 4973603
Issued on: 11/27/1990
Inventor: Burstein

Deuterated cannabinoids as standards for the analysis of tetrahydrocannabinol and its metabolites in biological fluids
Patent #: 5036014
Issued on: 07/30/1991
Inventor: ElSohly, et al.

Fluorescene polarization immunoassay for tetrahydrocannabinoids
Patent #: 5144030
Issued on: 09/01/1992
Inventor: Wang, et al.

NMDA-blocking pharmaceutical compositions
Patent #: 5284867
Issued on: 02/08/1994
Inventor: Kloog, et al.

(3R,4R)-Ɗ6 -tetrahydrocannabinol-7-oic acids useful as antiinflammatory agents and analgesics Patent #: 5338753
Issued on: 08/16/1994
Inventor: Burstein, et al.

Inventors

Assignee

Application

No. 190089 filed on 05/24/1994

US Classes:

514/454, Tricyclo ring system having the hetero ring as one of the cyclos549/390, Dibenzo(b,d)pyrans (including hydrogenated)549/391Plural chalcogens bonded directly to the tricyclo ring system

Examiners

Primary: Chan, Nicky

Attorney, Agent or Firm

International Classes

A61K 031/35
C07D 311/80

Foreign Application Priority Data

1991-09-12 IL

Abstract

The invention relates to novel compounds of formula (I) wherein R is a hydrogen atom or a C1 -C5 alkyl group and R2 is selected from the group consisting of: (a) a straight-chained or branched C5 -C12 alkyl radical; (b) a group --O--R4, wherein R4 is a straight-chained or branched C2 -C9 alkyl radical which may be substituted at the terminal carbon atom by a phenyl group; (c) a group --(CH2)n --O--alkyl, wherein n is an integer of from 1 to 7 and the alkyl group contains from 1 to 5 carbon atoms, having the (3S,4S) configuration, essentially free of the (3R,4R) enantiomer. The invention also relates to process for the preparation of compounds of formula (I) as defined above. The invention further relates to pharmaceutical compositions which possess analgesic, anti-inflammatory, anti-emetic, anti-glaucoma, leukocytes antiadhesion or PAF activity, containing as active ingredient compounds of formula (I) as defined above.

Other References

  • Mechoulam et al., Tetrahedron: Asymmetry, vol. 1, No. 5, pp. 315-318 (199 )
  • Feigenbaum et al., Proc. Natl. Acad. Sci. USA, vol. 86, pp. 9584-9587 (1989)
  • Schwartz et al., J. Org. Chem., vol. 51, pp. 5463-5465 (1986
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