Details for Patent: 4,696,949

Summary for Patent: 4,696,949

Title:	Novel tri-phenyl alkane and alkene derivatives and their preparation and use
Abstract:	The invention provides novel compounds of the formula: ##STR1## wherein n is 0 to 4, R1 and R2, which can be the same or different are H, OH, alkoxy of 1 to 4 carbon atoms, benzyloxy or methoxymethoxy; R3 is H, OH, halogen, alkoxy of 1 to 4 carbon atoms, benzyloxy, methoxymethoxy, 2,3-dihydroxypropoxy or ##STR2## wherein m is 1 or 2, R6 and R7, which can be the same or different are H or an alkyl group of 1 to 4 carbon atoms, or ##STR3## can form an N-containing three-, four-, five- or six-membered heterocyclic ring; R4 is OH, F, Cl, Br, I, mesyloxy, tosyloxy, alkylcarbonyloxy of 1 to 4 C-atoms, formyloxy or CH2 R4 is replaced by CHO; R5 is H or OH; or R4 and R5 together form an --O-- bridge between the carbon atoms to which they are attached, and their non-toxic pharmaceutically acceptable salts and esters and mixtures thereof. Processes for the preparation of these compounds are described, and also novel pharmaceutical compositions containing them. These compounds exhibit valuable pharmacological properties as estrogenic, anti-estrogenic, and progestanic agents. They are also effective against oestrogen-dependent tumors. Certain compounds are useful as chemical intermediates for the preparation of pharmacologically active compounds of the invention.
Inventor(s):	Reijo J. Toivola, Arto J. Karjalainen, Kauko O. A. Kurkela, Marja-Liisa Soderwall, Lauri V. M. Kangas, Guillermo L. Blanco, Hannu K. Sunduiqst
Assignee:	Orion Oyj
Application Number:	US06/823,856
Patent Claim Types: see list of patent claims	Use; Composition;

US Patent 4,696,949: Scope, Claims, and US Patent Landscape

What does US 4,696,949 claim, at the molecule and use level?

US 4,696,949 claims a single core chemical family defined by a generic structure (“formula ##STR50##”), then narrows to specific exemplified embodiments and expands into formulation and method-of-use claims.

Claim-by-claim scope (as provided)

Claim	Scope type	What is claimed (literal wording basis)	Practical reach in US freedom-to-operate terms
1	Chemical genus	“A compound of the formula ##STR50##” or a “non-toxic pharmaceutically acceptable salt or N-oxides”	Broadest chemical coverage in the patent. Any embodiment that falls within the structural formula is inside scope, subject to claim construction of the drawn structure.
2	Chemical subset (specific compound)	“4-chloro-1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]-1-butene” and salts	A direct target compound. High infringement relevance if marketed or used.
3	Isomer subset	“the trans-isomer” of the compound in claim 2 and salts	Narrows to stereochemistry. If competitors market only cis, this claim still requires analysis against the specific claim wording (trans-only vs mixture).
4	Salt form subset	“the citrate of the trans-isomer” and non-toxic pharmaceutically acceptable salts	Narrows to a specific counterion (citrate) and trans form. If a competitor sells free base or other salt (HCl, maleate), this claim may not read, depending on claim construction.
5	Composition-of-matter (pharmaceutical)	“pharmaceutical composition suitable for treating hormone-dependent tumours” with an anti-tumor effective amount of claim 1 compound (or salt) plus compatible carrier	Expands to product formulations and methods of use for oncology. Even if the molecule is known, formulation that matches the claim language can be captured.
6	Method-of-use (regimen)	“method of producing an anti-oestrogenic effect” by administering an anti-oestrogenic effective amount of claim 3 compound (or salt)	Covers treatment regimens framed as producing anti-estrogenic effect via the trans-isomer compound (or salt).
7	Dependent method-of-use	Method of claim 6 where anti-oestrogenic effect is produced in “oestrogen-dependent tumour” patients	Captures the clinical subpopulation and intended use within the anti-oestrogenic mechanism framing.

How broad is the chemical coverage of claim 1?

Claim 1 is a structural “formula” claim with allowances for:

• pharmaceutically acceptable salts
• N-oxides

In US practice, this is typically construed as a genus defined by the limits of the drawn structure in the spec. Because the exact substituent pattern is not reproduced in the prompt (the text contains “##STR50##”), claim 1’s enforceable scope is bounded by the exact structural variables in that formula as filed.

What the dependent claims do to the scope

• Claims 2 to 4 anchor the genus to a specific molecule and its stereochemical and salt embodiments. This strengthens the patentee’s narrative that the genus covers at least that specific compound (often relevant for written description and enablement, and for claim construction).
• Claims 6 to 7 anchor the intended mechanism and patient population to anti-oestrogenic effect in hormone-dependent and oestrogen-dependent tumour settings.

What is the commercial “bullseye” in infringement analysis?

The highest-value practical targets for any competitive entry are the named compound and its constrained variants:

1. Named compound (claim 2)
   4-chloro-1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]-1-butene] (with pharmaceutically acceptable salts)

2. Trans stereoisomer (claim 3)
   trans-isomer of the named compound

3. Trans citrate salt (claim 4)
   citrate of the trans-isomer

4. Treatment indications framed as hormone-dependent / estrogen-dependent tumors (claims 5, 7)

   • claim 5: hormone-dependent tumours (composition)
   • claim 7: estrogen-dependent tumour (method)

If an infringing product exists, it will almost certainly sit inside claims 2 to 4 first, and then pull formulation and use claims through claims 5 to 7.

What does the patent cover on the product side: composition and carriers?

Claim 5 covers a “pharmaceutical composition suitable for treating hormone-dependent tumours” that contains:

• an anti-tumour effective amount of a claim 1 compound (or non-toxic pharmaceutically acceptable salt)
• a compatible pharmaceutically carrier

This is a classic formulation claim. The scope is typically broad on carriers (any “compatible” carrier), but the active ingredient must be one of the covered claim 1 compounds (or salt).

What does the patent cover on the clinical/regimen side: anti-estrogen effect?

Claims 6 and 7 are method-of-use claims:

• claim 6: producing an anti-oestrogenic effect by administering a compound of claim 3 (trans-isomer) or its salt
• claim 7: the same effect in subjects with estrogen-dependent tumors

From an enforcement perspective, method claims can be pursued when there is induced infringement (e.g., prescribing, labeling, marketing tied to the claimed regimen). Product labeling that states the claimed anti-estrogenic use and references the active ingredient that matches claim 3 can be highly relevant.

Patent landscape implications in the US: how this family constrains competitors

Without the full claim chart and without the complete chemical formula text, the landscape can still be mapped structurally by the claim architecture: molecule (genus) → specific named compound → trans-only → citrate salt → oncology use and anti-oestrogenic effect.

Likely competitive entry points and how the claims hit them

Competitor design choice	Claim impact
Develop a compound that falls inside the genus of claim 1	Direct chemical infringement risk (claim 1), which also triggers composition claim 5 if formulated and used as claimed.
Use the named compound but market as cis-only	Reduces risk for claims 3 and 6-7 if only cis is administered; still may hit claim 1 and claim 2 (which are not explicitly trans-limited) depending on whether “cis vs trans” still meets claim 2.
Use trans isomer but a different salt (not citrate)	Hits claim 3 and method claims 6-7 (salts allowed generally); may avoid claim 4 if the salt is not citrate.
Use trans citrate specifically	Hits all of claims 3 and 4; also composition claim 5 and methods 6-7.
Avoid the trans isomer entirely (no trans in the administered form)	Avoids claim 3 and dependent use claims 6-7, but still faces claim 1 and claim 2 risk if the administered compound still falls within those claims’ structural definitions.

What to look for in the US prosecution and validity posture (landscape mechanics)

The core landscape question for investors and R&D teams is whether later patents can carve around this molecule and use space, or whether they are blocked by improvements that still fall within the genus or trans/citrate constraints.

Because the prompt provides only claim text, the best landscape read is the claim layering itself:

• If later patents also use the same trans-isomer active and sell it in a tumor or anti-oestrogen framing, they often risk overlap with claims 5-7.
• If later patents attempt to claim new salts or new formulations, the breadth of claim 1’s “pharmaceutically acceptable salt” can reduce room to maneuver unless the new salt is argued not to be “pharmaceutically acceptable” or not within the drawn genus.

How the claim wording constrains design-arounds

Genus capture (claim 1) reduces “molecule-only” workarounds

A competitor cannot avoid claim 1 simply by changing synthesis steps or dosage form; they must move outside the structural limits of formula ##STR50## (or avoid “non-toxic pharmaceutically acceptable salts or N-oxides”).

Trans restriction (claim 3) creates a narrow carve path

The trans/isomer choice is the clearest operational design variable in the claim set:

• trans: directly captured by claim 3
• citrate of trans: directly captured by claim 4

Indication and mechanism language can be both limiting and enforceable

Claims 6-7 frame the method as “producing an anti-oestrogenic effect” in subjects where such effect is desired, including estrogen-dependent tumors. That framing can be enforced against intended use even where the dosage form matches broadly.

Key takeaways on claim scope for FTO, portfolio strategy, and litigation risk

1. US 4,696,949 is layered: it starts with a broad structural genus (claim 1), then locks in a specific named compound (claim 2), tightens to trans-only (claim 3), and then tightens again to trans citrate (claim 4).
2. Product and label risk tracks the molecule: once a covered compound is present, claim 5 can capture formulations for hormone-dependent tumors.
3. Regimen risk is specifically tied to trans: claims 6-7 are anchored to the trans compound of claim 3 and to anti-oestrogenic effect in estrogen-dependent tumor settings.
4. Best design-around lever is stereochemistry and salt identity: avoiding trans and/or avoiding citrate reduces overlap with dependent claims, but claim 1 and claim 2 can still be obstacles if the administered compound remains inside the genus.

Key Takeaways

• Highest-risk embodiments in this patent are the trans-isomer and its citrate salt: claims 3 and 4 plus method claims 6 and 7, and composition claim 5 when formulated for hormone-dependent tumors.
• The genus claim (1) is the broadest block on chemical design changes; avoiding trans/citrate may not avoid claim 1 if the structure still fits formula ##STR50##.
• Use claims are mechanism- and indication-framed: anti-oestrogenic effect and estrogen-dependent tumor language can make labeling and prescribing activity central in enforcement.

FAQs

1) Does the patent only cover one specific compound?
No. It has a broad genus claim (claim 1) plus specific embodiments (claims 2-4) and downstream composition and method claims (claims 5-7).

2) Can a different salt avoid infringement?
It can reduce overlap with claim 4 if the product is not citrate. However, claim 3 still covers “pharmaceutically acceptable salt” of the trans-isomer, and claim 1 also covers salts generally.

3) Is stereochemistry the main design-around lever?
Yes. Claim 3 restricts to the trans-isomer, and the trans basis drives the method claims in claims 6-7.

4) What product types are covered?
Pharmaceutical compositions (claim 5) and methods of treating based on producing an anti-oestrogenic effect (claims 6-7).

5) What clinical populations are captured?
Subjects where anti-oestrogenic effect is desired (claim 6), including subjects with estrogen-dependent tumors (claim 7).

References

[1] United States Patent No. 4,696,949. Claims as provided in the prompt.

Drugs Protected by US Patent 4,696,949

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: 4,696,949

Foriegn Application Priority Data
Foreign Country	Foreign Patent Number	Foreign Patent Date
United Kingdom	8218414	Jun 25, 1982

International Family Members for US Patent 4,696,949

Country	Patent Number	Estimated Expiration	Supplementary Protection Certificate	SPC Country	SPC Expiration
European Patent Office	0095875		SPC/GB96/029	United Kingdom
European Patent Office	0095875		96C0029	Belgium
Austria	22064
Austria	383344
Austria	A192983