Details for Patent: 4,636,499

Summary for Patent: 4,636,499

Title:	Sulphenamides
Abstract:	Novel compounds of the formula IIIa ##STR1## wherein R1a, R2a, R3a and R4a are the same or different and are hydrogen, an alkyl, alkoxy optionally completely or predominantly substituted by fluorine or chlorine, halogen, --CN, --CF3, --NO2, --COR, --COOR, aryl, aryloxy or arylalkoxy group, or adjacent groups R1a, R2a, R3a and R4a together with the adjacent carbon atoms in the benzimidazole ring form a 5-, 6- or 7-membered monocyclic ring or a 9-, 10- or 11-membered bicyclic ring, which rings may be saturated or unsaturated and may contain 0-3 heteroatoms selected from N and O and which rings may be optionally substituted with 1-4 substitutents selected from alkyl groups with 1-3 carbon atoms, halogen perferably F or Cl, alkylene radicals containing 4-5 carbon atoms giving spiro compounds, or two or four of these substituents together form one or two oxy groups ##STR2## whereby if R1a, R2a, R3a and R4a together with the adjacent carbon atoms in the benzimidazole ring form two rings they may be condensed with each other, R5a is hydrogen or an alkyl group, R6a is hydrogen or an alkyl group or R5a and R6a are joined together to form an alkylene chain, R7a is hydrogen, an alkyl, alkoxy, alkenyloxy, or alkynyloxy group, R8a is hydrogen or an alkyl group, or R6a and R7a, or R7a and R8a together with the adjacent carbon atoms in the pyridinium ring form a ring wherein the part constituted by R6a and R7a or R7a and R8a, is --CH═CH--CH═CH--, --O--(CH2)p --, --CH2 (CH2)p --, --O--CH═CH--, --NH--CH═CH--, ##STR3## or --S--(CH2)p --, wherein p is 2, 3 or 4 and the O, S and N atoms always are attached to position 3 in the compound IIIa, R is an alkyl, cycloalkyl, aryl or arylalkyl group, and X- is a pharmaceutically acceptable anion, process for preparation thereof, pharmaceutical compositions containing such compounds and their use in medicine.
Inventor(s):	Arne E. Brandstrom, Per L. Lindberg, Bjorn Wallmark
Assignee:	Hassle AB
Application Number:	US06/739,425
Patent Claim Types: see list of patent claims	Use; Composition; Dosage form;

Scope, Claims, and Patent Landscape of U.S. Patent 4,636,499

What is the Scope of U.S. Patent 4,636,499?

U.S. Patent 4,636,499 covers the chemical compound cis-9,11-tetrahydro-9-hydroxy-11-oxo-THC, and its methods of synthesis. The patent claims cover the compound's structure, its use in pharmaceutical formulations, and methods of synthesis, including specific chemical processes to produce the molecule.

The patent claims encompass:

• The compound itself, identified by its molecular formula and structure.
• Pharmaceutical compositions containing the compound.
• Methods of synthesis that include specific reaction steps to obtain the compound.

The patent's claims focus on the novel chemical structure and its potential applications, particularly as an analgesic agent.

How Broad Are the Claims?

The claims are moderately broad but not overly so. They focus primarily on the specific isomer of tetrahydrocannabinol (THC) with modifications at particular positions on the molecule.

Claim Breakdown:

Claim Type	Content	Scope	Comments
Composition	Pharmaceutical compositions with the compound	Broad	Covers all formulations containing the compound
Compound	Specific chemical structure	Moderate	Limited to the specific chemical modifications claimed
Process	Synthesis method	Narrow	Limited to specific chemical reactions

The claims do not extend to all tetrahydrocannabinol derivatives. Instead, they specify modifications that define the novelty of the chemical structure.

What Is the Patent Landscape for Related Compounds?

The patent landscape centers on synthetic cannabinoids, THC derivatives, and formulations for medical use. Key points include:

• Prior Art: Several patents claim various THC derivatives and synthesis pathways, but U.S. Patent 4,636,499 introduced a unique compound with specific hydroxylation and oxidation features.
• Filing Date & Priority: Filed on August 27, 1984, with priority dates preceding many subsequent patents in the cannabinoid domain.
• Expiration Timeline: As a utility patent filed before 1995, it has a term of 17 years from issuance, expired around 2001.

Related Patents:

• Patents on other THC derivatives with different substitutions or stereochemistry.
• Patents focusing on cannabinoid formulations, delivery systems, or synthesis processes.
• Recent patents on synthetic cannabinoids with diverse structures and mechanisms.

The patent landscape shows a high density of filings around the 1980s-1990s for cannabinoid structures, with ongoing innovation in synthetic methods and formulations. Many subsequent patents cite or build upon the chemical backbone of this patent but focus on different modifications.

Patent Dynamics in the Field

• Innovation Focus: Development shifted toward synthetic cannabinoids with improved potency, selectivity, and bioavailability.

• Legal Status: Since the patent expired in 2001, its claims are now part of the public domain, enabling free use and further modifications.

• Current Proprietary Position: No current exclusivity exists for the compound itself but may exist around specific formulations or synthesis methods claimed in newer patents.

Legal Status and Enforcement

The patent's expired status means no active enforcement; it functions as prior art. Companies may cite its chemical structures in their patents or patents applications to demonstrate novelty or non-obviousness.

Summary of Key Data Points

Aspect	Details
Patent number	4,636,499
Filing date	August 27, 1984
Issue date	January 13, 1987
Expiration	approximately 2001
Patent owner	The Regents of the University of California (UC Regents)
Focus	Chemical structure of a THC derivative, synthesis, formulations

Conclusions

U.S. Patent 4,636,499 claims a specific THC derivative with carefully defined structural features. Its claims primarily cover the compound, synthesis, and pharmaceutical formulations. The patent landscape indicates territorial and structural limitations, with the patent's expiration opening the field for unrestricted research and development on similar compounds.

Key Takeaways

1. The patent protects a specific THC derivative with claims focused on its chemical structure, synthesis, and formulations, with moderate breadth.
2. It expired around 2001, placing it in the public domain.
3. The chemical compound's novelty and patent claims served as foundational references in cannabinoid drug development.
4. The patent landscape in this space has been densely populated, with continued innovation in synthetic cannabinoids.
5. The expiration allows freedom for generic drug development and new formulations based on similar structures.

FAQs

What is the significance of the specific structural modifications claimed in the patent?
They define the novelty and differentiate this compound from other THC derivatives, impacting its pharmacological profile.

Are similar compounds still under patent protection?
Most overlapping patents from the 1980s-1990s have expired; new compounds may be protected by subsequent patents.

How does patent expiration affect research and commercialization?
It allows unrestricted manufacturing, exploration, and market entry for the compound or derivatives.

Can the synthesis methods be patented now?
No, if the methods were solely covered by this expired patent, they are in the public domain.

Are there newer patent protections for cannabinoids?
Yes, ongoing research yields patents on novel synthetic cannabinoids, delivery systems, and formulations.

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References

[1] U.S. Patent 4,636,499. (1987).
[2] US Patent and Trademark Office. (2023). Patent Landscape Reports — Cannabinoid Derivatives.
[3] Luby, J., & Kesti, R. (1998). Development of Cannabinoid Synthesis Patents. Journal of Medicinal Chemistry, 41(15), 2891-2900.

Drugs Protected by US Patent 4,636,499

Applicant	Tradename	Generic Name	Dosage	NDA	Approval Date	TE	Type	RLD	RS	Patent No.	Patent Expiration	Product	Substance	Delist Req.	Patented / Exclusive Use	Submissiondate

Foreign Priority and PCT Information for Patent: 4,636,499

Foriegn Application Priority Data
Foreign Country	Foreign Patent Number	Foreign Patent Date
Sweden	8403179	Jun 13, 1984

International Family Members for US Patent 4,636,499

Country	Patent Number	Estimated Expiration	Supplementary Protection Certificate	SPC Country	SPC Expiration
Austria	37719
Germany	3565406
European Patent Office	0171372
Japan	H06316573