Details for Patent: 3,954,872

Summary for Patent: 3,954,872

Title:	1-(2',6'-Dimethyl-phenoxy)-2-amino-alkanes and salts thereof
Abstract:	Compounds of the formula ##EQU1## wherein R is hydrogen or alkyl of 1 to 3 carbon atoms, andR1 is hydrogen or methyl,And non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as anticonvulsives and antiarrhythmics in warmblooded animals.
Inventor(s):	Herbert Koppe, Karl Zeile, Werner Kummer, Helmut Stahle, Peter Danneberg
Assignee:	Boehringer Ingelheim GmbH
Application Number:	US05/511,063
Patent Claim Types: see list of patent claims	Compound;

United States Patent 3,954,872 Scope, Claim Coverage, and US Patent Landscape for Racemic/Optically Active 1-(2,6-dimethyl-phenoxy)-2-aminopropane, -pentane, and -hexane

Executive summary: US Patent 3,954,872 claims a structural class defined by a substituted phenoxy-2-aminopropane family with defined substituents at the side-chain terminus (R = H or C1–C3 alkyl; R1 = H or methyl) and also covers three specific members: 1-(2’,6’-dimethyl-phenoxy)-2-aminopropane, -2-aminopentane, and -2-aminohexane in racemic or optically active form, including pharmacologically acceptable acid addition salts. From the claim text provided, the patent’s practical value is breadth at the “general formula” level plus high enforceability anchors at the three named embodiments.

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What does US Patent 3,954,872 claim and what is the exact compound scope?

Short answer: The patent covers (i) a formula-defined compound class with two substitution handles (R and R1) and (ii) three specific 2-amino phenoxyalkanes (propane, pentane, hexane analogs) plus their acid addition salts in racemic or optically active form.

Core claim architecture

From the claims supplied:

• Claim 1 (formula claim):
  A racemic or optically active compound of formula (as shown in the patent) wherein:

  • R is hydrogen or alkyl of 1 to 3 carbon atoms (CH3, C2H5, n-/i-Pr equivalents implied by “alkyl of 1 to 3 carbon atoms”), and
  • R1 is hydrogen or methyl, and
  • the compound is either the free base or a non-toxic, pharmacologically acceptable acid addition salt.

• Claims 2–4 (dependent embodiment claims):

  • Claim 2: 1-(2’,6’-dimethyl-phenoxy)-2-amino-propane (racemic or optically active) and acid addition salts
  • Claim 3: 1-(2’,6’-dimethyl-phenoxy)-2-amino-pentane (racemic or optically active) and acid addition salts
  • Claim 4: 1-(2’,6’-dimethyl-phenoxy)-2-amino-hexane (racemic or optically active) and acid addition salts

Substitution boundary implied by R and R1

Even without the full chemical structure rendering, the claim limitations drive a tight grid:

• R position permitted: H, or C1–C3 alkyl
  • That means the claimed side-chain variants run across unsubstituted through methyl, ethyl, and propyl analogs.
• R1 position permitted: H or methyl
  • This supports diastereomeric potential where the optically active compounds depend on stereocenters created by the substitution pattern.

Why “racemic or optically active” matters for infringement

Because Claim 1 expressly covers both:

• racemic mixtures, and
• optically active (enantiomerically enriched) forms,

a generic or competitor cannot evade coverage by marketing a single enantiomer if it still falls within the structural limitations.

What acid addition salts expand (and what they do not)

The salt language (“non-toxic, pharmacologically acceptable acid addition salt thereof”) broadens commercial coverage:

• It covers the marketed salt forms of a covered free base.
• It does not automatically cover quaternary ammonium salts or non-pharmacologically acceptable salts unless they qualify as “non-toxic” and “pharmacologically acceptable.”

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How broad is the formula claim versus the named embodiment claims?

Short answer: Claim 1 is the broadest rights grant because it covers a structural class defined by R and R1. Claims 2–4 are narrower but provide explicit anchor compounds that can simplify claim charts and infringement mapping.

Enforcement leverage: formula claim vs. dependent claims

• Formula Claim 1 can capture many analogs that fit the R and R1 constraints, assuming the “formula (as shown)” includes the same backbone and phenoxy substitution.
• Claims 2–4 list three specific chain-length embodiments. These typically:
  • reduce the need to litigate whether an accused compound fits the formula parsing, and
  • support easier “identity” mapping in litigation and in licensing negotiations.

Practical coverage implications

• A party making 1-(2,6-dimethyl-phenoxy)-2-aminoalkanes with chain lengths corresponding to the propane/pentane/hexane family can expect direct pressure under Claims 2–4 if the backbone matches the patent’s structural definition.

• A party making an analog where either:

  • R is outside H or C1–C3, or
  • R1 is outside H or methyl,

  falls outside Claim 1 as written.

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Which compound species fall squarely within Claims 2–4 (propane/pentane/hexane)?

Short answer: The claims explicitly list three species across chain length at the amine side chain: C3, C5, and C6 equivalents (propane/pentane/hexane), each as racemic or optically active and each as free base or acid addition salt.

Claim 2 species

• 1-(2’,6’-dimethyl-phenoxy)-2-amino-propane
• non-toxic pharmacologically acceptable acid addition salts
• racemic or optically active

Claim 3 species

• 1-(2’,6’-dimethyl-phenoxy)-2-amino-pentane
• non-toxic pharmacologically acceptable acid addition salts
• racemic or optically active

Claim 4 species

• 1-(2’,6’-dimethyl-phenoxy)-2-amino-hexane
• non-toxic pharmacologically acceptable acid addition salts
• racemic or optically active

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What design-arounds are plausible based on R and R1 limits?

Short answer: Design-around is most plausibly achieved by moving the compound outside the R = H or C1–C3 alkyl and/or R1 = H or methyl constraints, or changing the scaffold so the phenoxy-2-amino pattern no longer matches the formula.

Most direct variable to attack: R

If the general formula claim uses R as a defined substituent:

• Moving from C1–C3 to C4+ alkyl is an express outside option.
• Changing R to branched substituents not counted as 1 to 3 carbon atoms can also avoid Claim 1 coverage.

Second lever: R1

• If R1 is limited to H or methyl, then analogs with R1 = ethyl or other substituents likely avoid Claim 1.

Stereochemistry does not help

Because both racemic and optically active forms are included, stereochemical purity is not a typical escape route unless the accused species is outside the defined structural substitution pattern.

Salt form typically does not help

Because acid addition salts are included, changing from free base to another “pharmacologically acceptable” acid salt still risks infringement.

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What patent landscape is typically associated with this kind of family claim (formulation, stereochemistry, and process patents)?

Short answer: For a chemical class defined by formula plus salt forms, the broader landscape usually splits into (i) process patents, (ii) salt/polymorph/formulation patents, and (iii) stereochemistry/selection patents. Those can meaningfully expand or narrow enforceable coverage even when a core formula patent expires or is limited.

What to expect around this type of claim

Given the structure and the explicit coverage of racemic/optical forms and acid addition salts, common surrounding patent themes in the US include:

1. Salt selection and preparation

   • Claims directed to a specific acid (e.g., HCl, fumarate, maleate, etc.) with a demonstrated property set.
   • Often overlaps with Claim 1 salt language but can provide more specific enforceability.

2. Enantiomer-specific composition claims

   • A later patent can claim a single enantiomer (e.g., (R)- or (S)- forms) with a defined activity profile.
   • Even if the earlier patent includes “optically active,” later claims may still matter for evidentiary and settlement leverage.

3. Manufacturing processes

   • Selective synthesis steps, resolution procedures, or purification.
   • These can create a separate infringement hook for commercial supply even if the exact compound claim scope is disputed.

4. Formulation and delivery

   • Oral dosage forms, controlled release, or specific excipient combinations.
   • Usually do not avoid compound claim exposure but can drive licensing for finished dosage forms.

What the claim text does not cover

Based on the provided claims alone, the patent does not appear to be a formulation or method-of-use claim. It is a chemical substance claim: formula + specific species + salts.

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How strong is the claim scope (litigation posture) based on the text provided?

Short answer: The claim is strong in that it is a direct composition claim with both a broad formula and explicit embodiment species. The strongest enforceability position comes from Claims 2–4 because they identify specific structures by name.

Strength indicators

• Composition coverage: The claim targets chemical entities rather than a process or use.
• Defined structural boundaries: R and R1 limits create determinable infringement questions.
• Explicit embodiments: Claims 2–4 include specific named compounds.
• Salt coverage: “Pharmacologically acceptable acid addition salts” expands commercial product forms.

Potential vulnerability indicators

• Dependence on the exact backbone in the “formula shown.” If the printed formula includes specific linkages beyond what can be inferred from the text, an accused compound must be mapped precisely.
• R and R1 limitations: competitors can potentially avoid coverage by selecting substitutions outside the express sets.

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What generic entry risks exist for compound and salt variants covered by Claims 1–4?

Short answer: Risk centers on whether a generic applicant’s API (or salt form) falls within the named embodiments or the R/R1 structural constraints. Optical form alone is not a design-around.

Risk categories

• Direct API risk:
  Manufacturing the exact compound species from Claims 2–4.
• Salt variant risk:
  Manufacturing an acid salt of a covered free base.
• Enantiomer risk:
  Manufacturing a single optically active enantiomer of a covered species still within the formula.

Lower risk scenarios

• Substitution patterns that change R to anything beyond H/C1–C3 alkyl or change R1 beyond H/methyl.
• Scaffold variants that disrupt the phenoxy-2-aminoalkane structure required by the formula.

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Does US Patent 3,954,872 likely cover method-of-use or only the chemical entity?

Short answer: Based on the claims provided, coverage is for the chemical entity and its salts, not a therapeutic method.

• Claims 1–4 are all directed to a “compound” of a formula and specific named compounds and their salts.
• No use limitation is present in the claim text shown.

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What does the claim language imply about stereocenters and stereoisomer coverage?

Short answer: Because the claim covers racemic or optically active forms, it includes stereoisomeric forms as long as the core scaffold and permitted substituents are present.

Stereochemical inclusion

• Claim 1: “racemic or optically active compound”
• Claims 2–4: “racemic or optically active” for each named species

Infringement mapping implication

An accused compound does not need to be a specific enantiomer unless the accused compound is outside the structural constraints. The claim wording removes an obvious stereochemical carve-out.

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Key takeaways

• US Patent 3,954,872 is a composition patent covering a substituted phenoxy-2-aminoalkane class with explicit limits on R (H or C1–C3 alkyl) and R1 (H or methyl) plus acid addition salts.
• Claims 2–4 are the most litigation-friendly anchors, explicitly covering:
  • 1-(2’,6’-dimethyl-phenoxy)-2-aminopropane
  • 1-(2’,6’-dimethyl-phenoxy)-2-aminopentane
  • 1-(2’,6’-dimethyl-phenoxy)-2-aminohexane each as racemic or optically active and as pharmacologically acceptable acid salts.
• Design-around is most plausible by moving R outside C1–C3 alkyl and/or R1 outside H or methyl, or by changing the scaffold so it no longer fits the formula.
• Salt form and stereochemical purity are not reliable escape routes because both are expressly covered.

FAQs

1) Does the patent cover only the free base or also acid addition salts?
It covers the compound and its non-toxic, pharmacologically acceptable acid addition salts.

2) Can a competitor avoid infringement by selling an enantiomer instead of a racemate?
No, because the claims cover racemic and optically active forms.

3) What substitution changes are likely outside the formula claim?
Changes where R is not H or C1–C3 alkyl and where R1 is not H or methyl.

4) Are propane, pentane, and hexane analogs explicitly named?
Yes. Claims 2–4 explicitly name the 2-aminopropane, 2-aminopentane, and 2-aminohexane analogs with the 2,6-dimethyl-phenoxy group.

5) Does the claim text indicate coverage of formulations or methods of treatment?
No. The provided claims are directed to compound compositions and their acid addition salts.

References

1. US Patent 3,954,872. (Claim text as provided by the user).

Drugs Protected by US Patent 3,954,872

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: 3,954,872

Foriegn Application Priority Data
Foreign Country	Foreign Patent Number	Foreign Patent Date
	88950	Sep 16, 1966
	94024	Aug 17, 1967

International Family Members for US Patent 3,954,872

Country	Patent Number	Estimated Expiration	Supplementary Protection Certificate	SPC Country	SPC Expiration
Austria	288353
Austria	289075
Austria	291225
Switzerland	509250
Switzerland	509251