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Patent landscape, scope, and claims: |
United States Patent 8,193,182 (8,193,182) Overview: Claim Scope, Likely Covered Chemical Space, and US Patent Landscape
United States Drug Patent 8,193,182 claims a family of substituted compounds defined through layered structural variables (Formulas I-1, II, and additional downstream formulas), plus pharmaceutical compositions and stereochemical/enantiopurity variants (notably an (S)-enantiomer with specified purity thresholds). The claim set uses Markush-style breadth at multiple levels (aryl/heteroaryl/cycloalkyl/heterocycloalkyl “plug-ins”, broad substitution definitions for R1/R2/R3, and hydrogen/alkyl/heterocycloalkyl for R9). It also includes narrower dependent claims that lock in specific sub-choices (example: R9 = methyl and z = 1; R3 includes methyl or chloro; and B includes phenyl with single ortho/meta fluoro).
The net effect is a patent that is both:
- Breadth-enabled by generic formula variables and Markush ranges, and
- Commercialization-structured by dependent claims that target likely “lead” embodiments, including specific substituent patterns and (S)-enantiomer product forms.
What does the core compound claim cover (Claim 1 and its dependency chain)?
Claim 1: Formula I-1 compound with variable moieties
Claim 1 covers:
- A compound of Formula I-1 or pharmaceutically acceptable salt
- With B set to a moiety of Formula II, where:
- Wc is aryl, heteroaryl, heterocycloalkyl, or cycloalkyl
- q is an integer 0–4
- X is either:
- a bond, or
- —(CH(R9))z—
- with z = 1
- Y is —N(R9)—
- Wd defines additional substitution parameters including:
- R1, R2, R3, each with multiple allowed substituent classes
- each instance of R9 independently hydrogen, alkyl, or heterocycloalkyl
R1 (per Claim 1 Wd definition)
R1 can be:
- H
- alkyl, alkenyl, alkynyl
- alkoxy
- amido
- alkoxycarbonyl
- sulfonamido
- halo
- cyano
- nitro
R2
R2 can be:
- alkyl, alkenyl, alkynyl
- cycloalkyl
- heterocycloalkyl
- aryl, heteroaryl
- heteroarylalkyl
- alkoxy
- amino
- halo, cyano
- hydroxy
- nitro
R3
R3 can be:
- H
- alkyl, alkenyl, alkynyl
- cycloalkyl
- heterocycloalkyl
- alkoxy
- amido, amino
- alkoxycarbonyl
- sulfonamido
- halo
- cyano
- hydroxy
- nitro
This combination defines a broad, substitution-tolerant chemical scaffold, with at least three independently tunable substitution positions (R1/R2/R3) plus variable heteroaromatic/cycloalkyl selection inside B and variable N-substitution via R9.
Claim 2: Narrowed B, q, and simplified substituent classes
Claim 2 depends from Claim 1 and narrows:
- q to 0 or 1 (from 0–4)
- Wc to aryl, heteroaryl, heterocycloalkyl, cycloalkyl (same set as Claim 1 in effect)
- R1 limited to hydrogen, alkyl, halo
- R2 limited to alkyl or halo
- R3 limited to hydrogen, alkyl, halo
This makes Claim 2 materially narrower than Claim 1 in substitution density and allowed functional groups.
Claim 3: X is the alkyl-bridging form and Y is NH
Claim 3 depends from Claim 1 and narrows to:
- X = —(CH(R9))z— and Y = —NH—
- This implicitly aligns with R9 = hydrogen for the N substituent in Y = —N(R9)— to become —NH—.
Claim 4: R3 set includes specific small groups
Claim 4 narrows R3 to:
- H, CH3, CH2CH3, CF3, Cl, F
This is a commercially realistic set of “plug-in” groups that often map to medicinal chemistry lead optimization patterns.
Claim 5: Specific X and reduced Wd definition (incomplete excerpt)
The user-provided excerpt for Claim 5 is truncated after “and Wd is …”. Based on visible text:
- Claim 5 fixes X as —(CH(R9))z—
- with R9 = methyl and z = 1
- and then further restricts Wd using an incomplete remainder.
Claim 6: (S)-predominant stereochemistry
Claim 6 narrows to:
- compound predominantly in an (S)-stereochemical configuration
Claim 7: structure of Formula V-A2
Claim 7 depends on Claim 1 and defines the compound as:
- having a structure of Formula V-A2
(The excerpt does not reproduce Formula V-A2 itself.)
Claims 8–9: additional narrow embodiments
- Claim 8 narrows R3 to methyl or chloro
- Claim 9 narrows Claim 7 further:
- B is a moiety of Formula II where Wc is aryl or cycloalkyl
Claims 10–12: pharmaceutical compositions
- Claim 10: pharmaceutical composition comprising:
- compound of Claim 1 (or salt)
- and pharmaceutically acceptable excipient
- Claim 11: narrows composition to compounds satisfying Claim 2’s B/R-range structure
- Claim 12: narrows further to:
- X = —(CH(R9))z—, with R9 = methyl and z = 1
- plus additional Wd limitations (truncated)
Claims 13–21: nested compound selection and stereopurity
The excerpt shows a chain of “A compound selected from …” claims (13 through 21) but the actual selected structures are truncated. What is visible:
- Claim 16: the compound is the S-enantiomer with enantiomeric purity:
- greater than about 55%, 80%, 90%, and 95% (as selectable thresholds within the claim wording)
- Claims 17 and 18–21: further depend on those selections (but selected compound identity is truncated)
This indicates the patent is likely drafting protection not only for the racemate/mixture but also for enriched (S) material and potentially for multiple discrete embodiments within that family.
Claims 22–24: additional concrete structures
- Claims 22, 23, 24: each covers compounds with an explicit structure (shown as “or a pharmaceutically acceptable salt thereof”), but the structure drawings are not included in the excerpt.
Claims 25–33: composition variants with multiple excipients
- Claim 25: composition with a plurality of excipients
- Claims 26–29: compositions tied to dependent-claim embodiments (claims 14, 15, 18, and 28)
- Claims 30–33: compositions tied to the concrete structure claims 22–24
- Claim 33: compositions further comprising a plurality of excipients
Claims 34–39: tight definition of R3/R9 and B substituent patterns
These dependent claims add a practical “fill-in-the-blanks” path toward specific commercial analogs.
- Claim 34: R3 is methyl or chloro
- Claim 35: R9 is methyl or ethyl
- Claim 36: B is substituted or unsubstituted phenyl
- Claim 37: B is substituted or unsubstituted cycloalkyl
- Claim 38: B is phenyl unsubstituted or substituted with fluoro
- Claim 39: B is phenyl with one fluoro in ortho or meta position
Taken together, the last set of claims targets:
- specific N-substituent types (R9 = methyl/ethyl)
- specific B aromatic substitution (phenyl with a single fluoro at specific ring positions)
- and specific R3 substituents (methyl/chloro)
How wide is the chemical space under the independent claim versus the later narrowing claims?
Breadth map (using only the variables explicitly provided)
| Variable |
Claim 1 breadth |
Later narrowed examples |
| B (Formula II) |
Wc = aryl/heteroaryl/heterocycloalkyl/cycloalkyl; q = 0–4 |
Claim 2: q = 0 or 1; Claim 9: Wc = aryl or cycloalkyl; Claim 36–39: B = phenyl or cycloalkyl, with fluoro placement constraints |
| X |
bond OR —(CH(R9))z— with z = 1 |
Claim 3/5/12: forces X = —(CH(R9))z— |
| Y |
—N(R9)— |
Claim 3: Y = —NH— |
| R1 |
very broad (multiple functional classes including amido, nitro, cyano, halo, etc.) |
Claim 2: R1 = H, alkyl, or halo |
| R2 |
broad (halo, cyano, hydroxy, nitro, amino, aryl, heteroaryl, etc.) |
Claim 2: R2 = alkyl or halo |
| R3 |
broad (H, multiple functional classes, halo, cyano, hydroxy, nitro, etc.) |
Claim 4/8/34: fixed sets including CH3/CH2CH3/CF3/Cl/F; then methyl/chloro |
Practical reading
- If you are designing around this patent, the strongest “design constraints” are implemented through the dependent claims: specific R3 values, specific R9 values, and positional fluoro substitution in B.
- If you are claiming commercially, Claim 1 and Claim 2 are the likely “workhorses” because they provide wide coverage over:
- B substitution patterns (within Markush),
- N-substituent (R9),
- and core substituent classes at R1/R2/R3.
What is the claim structure and where is it likely vulnerable (scope mechanics)?
1) Markush breadth at multiple levels
Claim 1 uses multi-level Markush definitions:
- Wc and q for B
- X as bond vs alkyl segment
- R9 across multiple loci (N substituent and CH(R9) segment)
- R1/R2/R3 as broad substitution groups
This is typical of patents intended to cover not just one final lead but a family.
2) Dependent claims lock likely commercial embodiments
Claims 6, 16–17 address stereochemistry and enantiomeric purity. Claims 34–39 add very specific substitution controls. This is consistent with a strategy:
- broad coverage for the chemical class (independent claims),
- plus tighter claims to secure fallback positions as prosecution and product selection converge.
3) Enantiomeric protection is explicitly quantified
Claim 16 includes enantiomeric purity thresholds (55%, 80%, 90%, 95% “greater than about”). That creates multiple enforceable “purity bands” for an (S) product pipeline.
Pharmaceutical composition scope: what is included and what is not constrained
Claims 10, 25, 29, 33 establish composition protection with:
- one or more compounds covered by the compound claims (or salts),
- pharmaceutically acceptable excipients,
- optionally “plurality of excipients.”
No route of administration, dose, or therapeutic indication is included in the excerpt. The composition claims are therefore structurally constrained primarily by:
- which compound is used (tied to claims 1/2/14/15/18/22/23/24 in dependent form),
- rather than by formulation design.
US patent landscape: what can be inferred from the claim set structure
This section addresses the landscape using only what is supported by the claim text you provided. The excerpt does not include:
- the patent title,
- assignee,
- filing dates,
- reference patents,
- citing/cited family members,
- claim numbering beyond 39,
- or any jurisdictional co-pending filings.
Accordingly, the only landscape conclusions that can be stated precisely are structural and competitive in nature:
1) Landscape for “design-around”
Competing programs would likely target one or more of these “hinge” constraints:
- eliminate the (S)-enriched form (if commercial intent is to avoid Claim 16 thresholds),
- adjust B substitution away from:
- phenyl with single ortho/meta fluoro (Claim 39),
- or at least away from the specific R3 (methyl/chloro) and R9 (methyl/ethyl) combinations (Claims 34–35),
- shift away from the Claim 2 substitution classes (R1/R2/R3 restricted to H/alkyl/halo for Claim 2),
- avoid compounds that fall within the broad R1/R2/R3 class space in Claim 1 if seeking broad freedom.
2) Landscape for “product selection and fallback”
The presence of:
- broad independent scaffold coverage (Claim 1),
- narrower subclass coverage (Claim 2, Claim 4/8, Claim 7 and derived structures),
- plus explicit stereochemistry/purity (Claim 6 and Claim 16–17),
signals that enforcement risk is layered. Even if a product misses one exact dependent embodiment (for example, B ring substitution), the independent claim may still capture it unless the product is engineered to exit at least one of the structural variable constraints.
Key Takeaways
- Claim 1 is a broad Markush claim covering a substituted chemical family with tunable B (Formula II), X, Y, and R1/R2/R3 substituents, plus variable N-substitution (R9).
- Claim 2 materially narrows the substituent classes at R1/R2/R3 and restricts q to 0 or 1, creating a second-tier, enforceable scope.
- The patent adds fallback specificity through dependent claims covering:
- R3 specific groups (Claim 4) and reduced sets (Claims 8 and 34),
- R9 choices (Claim 35),
- B choices including phenyl with fluoro and single ortho/meta fluoro (Claims 36–39).
- Stereochemistry is explicitly protected, including an (S)-enantiomer with enantiomeric purity thresholds above about 55%, 80%, 90%, and 95% (Claims 16 and 17).
- Composition claims protect formulations containing the claimed compounds and pharmaceutically acceptable excipients, with optional multiple excipients, and depend on which specific compound embodiments are used.
FAQs
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Which dependent claims most directly constrain freedom-to-operate for a (S)-enriched product?
Claims 6, 16, and 17 define (S) predominance and enforceable enantiomeric purity bands, making stereochemical form a primary axis of risk.
-
What is the most specific structural constraint among the late-dependent claims?
Claim 39, which limits B to phenyl with one fluoro in the ortho or meta position, is the tightest positional restriction in the provided excerpt.
-
If a competitor chooses a different R3 group than methyl/chloro, do they exit the patent?
Potentially for those specific embodiments: Claims 8 and 34 restrict R3. But Claim 1 remains broad on R3 unless the competitor also exits at least one other Claim 1 structural variable.
-
Does the patent protect only isolated compounds or also formulations?
It protects both. Claims 10, 25, 29, and 33 cover pharmaceutical compositions with excipients, tied to compound claims.
-
How does Claim 2 affect substitution flexibility compared with Claim 1?
Claim 2 restricts R1 to H/alkyl/halo, R2 to alkyl/halo, and R3 to H/alkyl/halo, and limits q to 0 or 1, reducing functional-group diversity relative to Claim 1.
References
- United States Patent 8,193,182 (claims provided in the prompt).
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