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Patent landscape, scope, and claims: |
United States Patent 4,680,291: Scope, Claim Architecture, and US Patent Landscape
US Patent 4,680,291 claims a broad genus of N-substituted aminocrotonic acid ester / propenyl amine-type compounds (formula I and multiple sub-formulas) plus (i) pharmaceutical compositions and (ii) animal mycosis treatment methods. The claims are structurally dense and license coverage is driven by (a) the general structural scaffold and (b) very wide substituent definitions on multiple rings and linker fragments, with targeted provisos that carve out specific sub-genuses.
What is the claimed chemical scope (claim 1) and what does it cover in practice?
Core structure: claim 1 genus (formula I)
Claim 1 is the primary coverage grant:
- Compound of formula I
- plus chemotherapeutically acceptable salts
The claim uses a nested set of variable substituents:
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R1 is defined as one of:
- a radical of formula IIa (with substituent options on R7 and R8), or
- a radical of formula IIb, IIc, IId, IIe (with substituent options on R9 and heteroatom/linker definitions including X and short alkyl chain spacers), or
- alternatively R1 and R2 together with the carbon atom form a fused/bridged substituent radical formula IIf or IIg (with p = 1, 2, or 3).
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R2 is hydrogen or lower alkyl (when not fused into IIf/IIg).
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R1 and R2 together can form IIf or IIg, which gives the claim a “ring-closure” escape from separate R1/R2 substitution rules.
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R3 and R4 together can be a polymethylene linker: --(CH2)u-- where u = 1 to 8 (claim 1(b)(ii) in the long-form constraints).
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R6 is the main “heteroaryl/aromatic tail” selector with either:
- (i) a five-membered aromatic heterocycle containing one heteroatom (O, S, or N) or optionally additional N atoms, with optional halogen/hydroxy/lower alkyl/lower alkoxy substitution, or
- (ii) formula IIIa, or
- (iii) formula IIIb (a carbonyl-terminated group of the type “--CO--R10”), or
- (iv) formula IIIc, IIId or IIIe, or
- (v) formula IIIf, or
- (vi) formula IIIg.
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R3/R4/R6 constraints include “any nitrogen ring atom present” optional lower alkyl substitution (for certain heterocycles), and multiple other broad sub-definitions.
Claim 1 proviso: “R1 not a specific IIa when R6 is IIIg or phenyl/phenylalkyl”
Claim 1 contains a controlling exclusion:
- “general proviso that R1 is not a radical of formula IIa when R6 is a radical of formula IIIg or phenyl or phenylalkyl.”
This is a key narrowing point: it prevents overlap of certain IIa-derived R1 substituents with certain R6 classes.
Claim 1(b) alternative
Claim 1(b) re-states the family in an alternative form where:
- R1 is a radical of formula IIa to IIe
- R2, R5 and R6 keep their claim-defined ranges
- and R3 and R4 are the --(CH2)u-- linker with u = 1 to 8.
In effect, claim 1 captures multiple ways to specify the same scaffold, but the provisos remain the gating constraints.
How wide are the substituent ranges in claim 1? (materially relevant ranges)
Halogen definition is unusually broad
Across claim 1 variable definitions:
- “halogen of atomic number from 9 to 53” includes F (9), Cl (17), Br (35), I (53).
Lower alkyl / alkoxy
- Lower alkyl and lower alkoxy are repeatedly used without hard carbon-number caps in the text you provided, but the claim elsewhere limits specific residues:
- alkyl (C1-6) for R4
- alkenyl (C3-12) and alkynyl (C3-12) for R4
- cycloalkyl (C3-8) for R4
- R14 options include alkyl and alkoxy (C1-12), and R20 options include alkyl (C1-12) or phenylalkyl (C7-12)
R4 is a major expansion vector
Claim 1 explicitly allows:
- R4 = alkyl (C1-6), alkenyl (C3-12), alkynyl (C3-12), or cycloalkyl (C3-8)alkyl (C1-6)
That is not a minor variation. It changes the steric and electronic profile of the propenyl/alkenyl fragment embedded in the scaffold.
What additional claim structure is provided beyond the genus? (claims 3-5 and dependent species)
Dependent “formula” claims that narrow the genus
The patent adds species-focused formula claims that lock in particular head-tail combinations and ranges:
- Claim 3: compounds having formula Ig with:
- R1I = 1-naphthyl, optionally mono-substituted by lower alkyl or alkoxy
- u = 1 to 8
- R6II is restricted to defined sub-sets:
- (i) R19 = hydrogen, hydroxy, lower alkoxy, or lower alkyl, or
- (ii) a carbonyl ester-like radical “--CO--OR20” with R20 = alkyl (C1-12) or phenylalkyl (C7-12) or
- (iii) the more detailed m/n/v sub-formula case (same as claim 1 parameterization)
This claim is operationally useful: it is a fast track to “naphthyl plus controlled R6II tail chemistry.”
These dependent claims do not just narrow; they also correct ambiguity by explicitly excluding certain linker patterns and specific R6 families.
What are the explicit named / example species claims? (claims 6, 8, 9-11, 12-21, 25-29)
Exact compound identity claims
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Claim 6 is an explicit structure name:
- N-(3-cyclohex-1-en-1-yl-2-trans-propenyl)-N-methyl-N-(1-naphthylmethyl)amine
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Claim 8 is explicit:
- 4-[N-methyl-N-(1-naphthylmethyl)]aminocrotonic acid ethyl ester
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Claims 9 and 10 are also explicit:
- N-(3-cyclohex-1-en-1-yl-2-cis-propenyl)-N-methyl-N-(1-naphthylmethyl)amine (claim 9)
- N-(3-cyclohexyl-2-trans-propenyl)-N-methyl-N-(1-naphthylmethyl)amine (claim 10)
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Claim 11 adds heteroaryl:
- N-methyl-N-[3-(5'-methyl-2'-thienyl)-2-trans-propenyl]-N-(1-naphthylmethyl)amine
These are enforcement anchors. In litigation or licensing, they reduce the question from “is it within the genus?” to “is it the exact molecule?”
Formula Ie / If claims with enumerated R6 choices
Claim 12 defines a structural formula Ie and then claims multiple specific R6 variants:
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Claim 12: formula Ie
- R1 and R6 as defined in claim 1
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Claims 13-19: fix R1 = 1-naphthyl and specify R6:
- claim 13: R6 = 2-thienyl
- claim 14: R6 is a specific substituted group (drawn in text as structure reference)
- claim 15: R6 = 4-pyridyl
- claim 16: R6 = --CH=CH.C6H5 (styryl/vinyl-phenyl)
- claim 17: R6 = Cyclohept-1-en-1-yl
- claim 18: R6 is another specific drawn group
- claim 19: R1 = 3-benzo[b]thienyl and R6 = Cyclohex-1-en-1-yl
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Claims 20-24: formula If with u fixed to 3, 4, 5 and R1/R6 choices:
- claim 21: R1 = 1-naphthyl, R6 = phenyl, u = 4
- claim 22: R1 = 1-naphthyl, R6 = phenyl, u = 3
- claim 23: R1 = 1-naphthyl, R6 = phenyl, u = 5
- claim 24: R1 = 5-tetralinyl, R6 = phenyl, u = 4
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Claims 25-29 are additional named scaffold variations:
- claim 25: N-(3-cyclohex-1-en-1-yl-2-cis-propenyl)-2-(1'-naphthyl)-piperidine
- claim 26: N-(1-acenaphthenyl)-N-methyl-N-(3-phenyl-2-trans-propenyl)amine
- claim 27: N-(1-acenaphthenyl)N-methyl-N-[3-(5'-methyl-2'-thienyl)-2-trans-propenyl]amine
- claim 28: N-(6,7,8,8a-tetrahydro-1-acenaphthenyl)-N-methyl-N-(3-phenyl-2-transpropenyl)amine
- claim 29: N-methyl-N-(2,3-dihydro-1-phenalenyl)-N-(3-phenyl-2-trans-propenyl)amine
Claims 30-34: R6-specific sub-classes
These narrow R6 only:
- claim 30: “R6 is an aromatic, five membered heterocycle as defined”
- claim 31: R6 = IIIa
- claim 32: R6 = IIIb
- claim 33: R6 = IIIc/IIId/IIIe
- claim 34: R6 = IIIf
This helps establish claim coverage for specific tail motifs.
What treatment and formulation scope is claimed?
Pharmaceutical composition
- Claim 2: composition with a therapeutically effective amount of claim 1 compound plus a chemotherapeutically acceptable diluent/carrier.
Method of combatting mycoses in animals
- Claim 7: administering an anti-mycotic amount to an animal in need.
This is animal-use directed, not human-use directed in the text provided.
What is the effective “license space” implied by the claim hierarchy?
The claim set spans three layers:
- Genus (claim 1): formula I plus broad substituent definitions with a small number of explicit provisos (including the R1/R6 combination exclusion).
- Sub-genuses (claims 3-5, 12, 20, 37-42): locked head group selections (naphthyl/acenaphthenyl/phenyl-type) and constrained linker/tail combinations, often with fixed indices (u = 1-8, s = 4, t = 3, a = 4).
- Species (claims 6, 8-11, 13-19, 21-29, 25, 26-29): enforcement-ready exact examples.
The result is a portfolio that can be asserted both broadly (genus) and specifically (named molecules), depending on claim construction outcomes.
How do claims 37-42 extend or re-articulate scope (potential continuation-like tightening)?
Claims 37-42 are a second “big re-statement” of formula-based scope, with the same core variable machinery:
- Claim 37: compound according to formula (drawn as a big formula with R1, R6 definition repeats), then salts.
- Claim 38-39: specific instantiations where R1 and R6 are fixed to drawn sub-groups.
- Claim 40: “q is 0 or 1.”
- Claim 41: R1 is a drawn group; and s, t, X, R9 as defined.
- Claim 42: R1 and R2 together form IIf or IIg with p = 1, 2, or 3.
Practically, this increases redundancy in claim coverage: different dependent paths can survive different validity challenges.
US patent landscape: how to position 4,680,291 vs competitors and what the landscape would hinge on
Landscape inference from claim content
The structure language indicates a fixed pharmacophore class:
- an aminated propenyl/crotonate framework,
- with a naphthylmethyl / naphthyl / acenaphthenyl head region,
- and a variable heteroaryl or aryl tail (R6),
- plus a polymethylene linker possibility (u).
This points to a landscape where competitor designs will try to:
- switch the head group (R1: naphthyl vs benzo[b]thiophene vs acenaphthenyl vs tetralinyl),
- alter the tail chemistry (R6 categories: IIIa through IIIg; heterocycles with heteroatom counts),
- change linker identity to avoid the claim’s explicit --(CH2)u-- patterns when the relevant dependent claims require “other than --(CH2)u--”.
Most likely “design-around pressure points” within the claim set
Key pressure points, based only on explicit wording provided:
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R1/R6 proviso
- R1 is not IIa when R6 is IIIg or phenyl or phenylalkyl.
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Linker provisos in dependent families
- Claim 5 requires R3 and R4 are other than --(CH2)u--.
- Claim 1(b)(ii) is the opposite: allows --(CH2)u-- with u = 1-8.
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R6 sub-class exclusions through R10 restrictions
- Several dependent constraints exclude R10 = phenyl or phenylalkoxy for certain carbonyl substituents (IIIb context).
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Specific fixed parameter values
- claims 3-5 and 4/5 include fixed indices: s = 4, t = 3, a = 4. Competitors can avoid those exact parameterizations if the claim construction ends up reading them strictly in those dependents.
Who is “in” the likely overlap zone
Based on the enumerated species claims (8-11, 13-19, 25-29), the most overlap likely exists for products containing:
- 1-naphthylmethyl or naphthyl / substituted naphthyl head groups,
- methylated amine (claim 6 uses N-methyl; other claims similarly),
- a propenyl/crotonate-like unsaturated carbon chain, and
- R6 that is either:
- five-membered heteroaryl (thiophene, furan, pyridine-class tails),
- or aryl/heteroaryl groups that can map into IIIa-IIIg categories.
Key Takeaways
- Claim 1 is the real breadth driver: formula I with extensive substituent permutations on R1 and R6, broad halogen range (9-53), and flexible R4 (alkyl/alkenyl/alkynyl/cycloalkyl-alkyl).
- The claim set is layered: genus (claim 1) plus redundant sub-genuses (claims 3-5, 12, 20, 37-42) and enforcement-ready exact molecules (claims 6, 8-11, 13-19, 21-29).
- The main narrowing logic is in provisos, especially the “R1 is not IIa when R6 is IIIg or phenyl/phenylalkyl” rule, plus explicit exclusions such as “R3 and R4 are other than --(CH2)u--” in claim 5.
- Landscape design-around will focus on violating provisos and shifting tail/linker/head selections away from the enumerated R6 categories and explicit linker forms tied to dependent claims.
FAQs
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Which claim should define the outer bounds for freedom-to-operate analysis?
Claim 1 sets the outer genus scope; claims 3-5 and 12/20/37-42 define major sub-areas with parameter restrictions and provisos.
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What is the most important structural exclusion to design around?
The claim-wide proviso preventing R1 = IIa when R6 = IIIg or phenyl/phenylalkyl.
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Does the patent cover compositions, or only compounds?
It covers both: claim 2 is a pharmaceutical composition; claim 7 is a method of mycosis treatment in animals.
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How do the “formula” dependent claims change risk compared with the genus?
They tighten specific parameter combinations (fixed indices like s = 4, t = 3, a = 4) and sometimes add targeted provisos that exclude certain linker or tail classes.
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Are there enforcement points beyond the broad genus language?
Yes. Multiple claims are explicit named molecules (not just formula language), including claims 6, 8-11, 25-29 and multiple formula-instance claims 13-19, 21-24.
References
[1] United States Patent 4,680,291. “United States Drug Patent 4,680,291” (claims as provided in prompt).
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