United States Patent 9,365,514 Scope, Claims, and US Patent Landscape for 9‑Ethyl‑6,6‑dimethyl‑8‑(4‑morpholin‑4‑yl‑piperidin‑1‑yl)‑11‑oxo‑6,11‑dihydro‑5H‑benzo[b]carbazole‑3‑carbonitrile With Sodium Lauryl Sulfate
Executive summary
US Patent 9,365,514 claims an oral pharmaceutical composition for the specific benzo[b]carbazole‑3‑carbonitrile small molecule (or a pharmaceutically acceptable salt) combined with (i) a pharmaceutically acceptable carrier and (ii) a specific dissolution aid: sodium lauryl sulfate (SLS). Claim 1 is the core composition claim with an embedded dissolution-aid limitation. Claim 2 adds “orally administrable formulation” language. Claim 3 expands the composition with optional polymer excipients selected from a long list. Claim 4 narrows by a measurable physicochemical property: substance water solubility <100 μg/mL at 25°C. The patent’s scope is therefore anchored to a specific API identity plus the specific excipient SLS and, in narrower form, to solubility and to the optional polymer universe in claim 3.
What is the scope of US Patent 9,365,514 based on the claim language?
Short answer: The patent scope covers oral dosage compositions containing the specific benzo[b]carbazole‑3‑carbonitrile compound (or salt) plus SLS as the dissolution aid, with carrier excipients, and optionally with specified polymers; a narrower subset further requires low water solubility (<100 μg/mL at 25°C).
Claim 1: “composition comprising API + carrier + dissolution aid is SLS”
Claim 1 has four functional structural elements:
- API identity: “a substance which is 9‑Ethyl‑6,6‑dimethyl‑8‑(4‑morpholin‑4‑yl‑piperidin‑1‑yl)‑11‑oxo‑6,11‑dihydro‑5H‑benzo[b]carbazole‑3‑carbonitrile or a salt thereof.”
- Carrier: “a pharmaceutically acceptable carrier.”
- Dissolution aid: “dissolution aid is sodium lauryl sulfate.”
- Composition format: no further dosage-form restriction in claim 1, only composition.
Implication for claim scope (practical infringement lens):
- To fall within claim 1, an accused product must include the claimed API (or a salt) and include SLS as the dissolution aid. Replacing SLS with another surfactant (even one used for dissolution) is the most direct design-around against claim 1, because the claim says dissolution aid is sodium lauryl sulfate.
- The claim does not require a specific dosage form, particle size, or ratio in the user-provided text. Those ratio/processing details could exist in the specification, but the infringement boundary for claim 1 as provided is primarily API identity plus SLS inclusion.
Claim 2: “orally administrable formulation comprising the composition described in claim 1”
Claim 2 is a dependent claim that adds:
- Oral administration requirement (“orally administrable formulation”).
- It “comprises the composition described in claim 1,” so it inherits the SLS dissolution-aid limitation.
Implication:
- Claim 2 targets oral dosage forms (tablets, capsules, granules, etc.), but the dependent nature means any oral product that fits claim 1 also can fit claim 2 if it is “orally administrable.”
Claim 3: polymers list as additional optional excipients
Claim 3: “composition according to claim 1, wherein the composition further comprises an organic polymer” selected from a listed set.
Polymer universe in claim 3 (as provided)
The polymers/excipients are:
- hydroxypropyl cellulose
- hydroxypropylmethyl cellulose
- methyl cellulose
- propylene glycol alginate ester
- powdered agar
- guar gum
- zein
- hydroxyethylmethyl cellulose
- a carboxyvinyl polymer
- polyvinyl alcohol
- a vinyl acetate resin
- sodium polystyrene sulfonate
- casein
- sodium caseinate
- a carboxyvinyl polymer (appears twice in the provided text)
- copolyvidone
- amino alkylmethacrylate copolymer E
- polyvinylacetal diethylaminoacetate
- methacrylic acid copolymer LD
- methacrylic acid copolymer S
- purified shellac
- carboxymethylethyl cellulose
- cellulose acetate phthalate
- hydroxypropylmethyl cellulose acetate succinate
- a mixture thereof
Implication for claim scope:
- This creates a broad “polymer could be any in the list” pathway. The claim is not limited to one polymer, so it is harder for a competitor to avoid infringement solely by choosing a different polymer, as long as their polymer is within the enumerated list.
- A design-around strategy consistent with the claim language would be to avoid using any polymer in the enumerated set. However, since claim 3 is dependent on claim 1, even without polymers in the list, claim 1 can still be implicated if SLS is present.
Claim 4: solubility-limited subset (<100 μg/mL at 25°C)
Claim 4: composition according to claim 1 “wherein said water solubility of the substance is less than 100 μg/mL at 25°C.”
Implication:
- This is a measurable physicochemical limitation. In litigation, it can become a key dispute area: whether the API (or salt) used in an accused product meets the solubility threshold, and how solubility is measured (method and conditions).
- Because claim 4 depends on claim 1, an accused product can still infringe claim 1 even if solubility is not below 100 μg/mL, but it would miss the narrower claim 4 subset if solubility exceeds the cutoff.
How broad is US Patent 9,365,514 compared with typical formulation claims?
Short answer: It is a targeted excipient-anchored formulation claim, not a broad “any dissolution aid” formulation claim.
Breadth drivers
- Broad carrier and composition language: “pharmaceutically acceptable carrier” and no dosage form limitation in claim 1.
- Broad polymer option (claim 3): multiple polymer categories.
- Broad within oral scope (claim 2): oral administration not tied to a specific dosage.
Narrowing drivers
- Single dissolution aid identity: SLS is expressly the dissolution aid. This is narrower than claims that cover a class of dissolution aids (e.g., surfactants generally).
- API specificity: the API chemical identity is fixed; the claim does not read on different chemical entities unless they fall within the exact named compound or a salt thereof.
- Solubility cutoff (claim 4): further narrows one dependent claim.
What is likely the key claim construction issue: “dissolution aid is sodium lauryl sulfate”?
Short answer: The dissolution-aid limitation is likely the central infringement lever.
Practical infringement questions created by the claim text
- If an accused formulation uses SLS but characterizes it as something other than “dissolution aid,” the text still says “dissolution aid is sodium lauryl sulfate.” Whether an excipient has the functional role of dissolution aid may be contested. Still, from a claim-language standpoint, SLS presence is strongly tied to dissolution-aid function.
- If a formulation uses SLS in trace amounts or as a processing aid, claim language may be argued either way depending on how the “dissolution aid” role is evidenced in the product and on claim construction (but the provided claim text makes SLS the dissolution aid).
How many US patent claims could cover similar compositions beyond 9,365,514?
Short answer: Patent estates for single-API small molecules often split into (i) composition/excipient patents, (ii) salt/form polymorph patents, and (iii) process/manufacturing patents. Based only on the claim text provided, 9,365,514 is clearly an excipient-dissolution composition patent, not a core molecule patent.
Likely adjacent US patent categories (based on claim type)
- Salt patents for “pharmaceutically acceptable salts” of the named compound.
- Solid form patents (crystal forms, polymorphs, amorphous forms) for the named compound or salt.
- Other dissolution-aid/surfactant patents using alternatives to SLS.
- Different polymer combination patents that keep API fixed but change excipient profiles.
- Dosage form patents (e.g., coated tablets, granulations, modified-release) that can coexist with the SLS composition claim.
What 9,365,514 does not cover (based on provided claims)
- It does not, on its face, cover formulations using different dissolution aids instead of SLS.
- It does not, on its face, cover IV or non-oral routes.
- It does not claim a broader generic “benzo[b]carbazole‑3‑carbonitrile derivatives” family; it is limited to the specifically enumerated substance and its salts.
What does the claim language suggest about the likely commercial “generic entry risk” for SLS-based products?
Short answer: The most direct generic risk is for oral generics that use the same API (or salt) and include SLS as dissolution aid.
Generic product design-around options suggested by the claims
- Switch dissolution aid away from SLS: replace SLS with another surfactant/dissolution agent. This is the cleanest path against claim 1’s “wherein dissolution aid is sodium lauryl sulfate.”
- Keep SLS out entirely: avoid SLS in formulation (including as an excipient with dissolution function).
- Avoid polymer list (for claim 3): keep polymers outside the enumerated set if a party wants to avoid claim 3, but this does not avoid claim 1 if SLS is present.
Where does this patent sit relative to FDA and Orange Book listing risk?
Short answer: The patent is an Orange Book-style formulation patent if listed against an NDA/ANDA product that uses the same API and SLS-inclusive composition.
Likely Orange Book listing mechanics implied by claim structure
- Composition patents like claim 1 and claim 2 often appear as “drug substance” or “drug product” patents depending on the Orange Book classification, and they list the specific formulation basis.
- To trigger listing-based exclusivity or FDA litigation risk, the formulation must match what is patented and what the reference listed drug (RLD) uses or what is claimed as the basis.
(No Orange Book patent list or FDA approval identifiers were provided; therefore no listing status can be stated from the provided inputs.)
Does claim 4’s solubility cutoff create a practical barrier for competitors?
Short answer: It can, but only for the narrower subset (claim 4), not the broader claim 1.
How solubility limits are typically litigated
- Measurement method, conditions, and salt form can affect solubility at 25°C.
- If a competitor uses the same named compound but in a different salt form, solubility may exceed the cutoff for the specific test conditions.
Net effect: claim 4 provides an extra lever, but claim 1 is still the primary barrier due to its dissolution-aid anchoring.
What other US patent types could be needed to fully invalidate or work around 9,365,514?
Short answer: Workarounds typically combine (i) formulation change (dissolution aid swap) with (ii) avoidance of any identical excipient combination and (iii) confirming no other patents in the estate target the new formulation.
Common cross-patent interaction patterns
- Even if 9,365,514 is avoided by swapping SLS, another patent may still cover a different dissolution aid plus the same API, including polymer combinations.
- If the competitor uses a salt, it must ensure the salt is not covered by a separate salt-forming or salt-composition patent.
- If the competitor uses a specific solid form to improve dissolution, it may trigger solid-state patents.
Key Takeaways
- US Patent 9,365,514 is an excipient-specific formulation patent centered on the named benzo[b]carbazole‑3‑carbonitrile API (or salt) plus sodium lauryl sulfate as the dissolution aid.
- Claim 1 is the dominant scope driver: infringement turns on whether the accused oral composition contains the claimed API (or salt) and uses SLS as dissolution aid.
- Claim 3 expands with an enumerated polymer list, but it is dependent on claim 1; avoiding claim 3 alone does not avoid claim 1 if SLS is used.
- Claim 4 adds a measurable subset: API water solubility <100 μg/mL at 25°C, potentially creating a second infringement/validity point for narrower products.
- The clearest design-around is to exclude SLS as the dissolution aid while keeping the API the same, subject to checking whether other patents in the same estate cover alternative dissolution-aid and polymer combinations.
FAQs
1) What is the single most important limitation in US 9,365,514 for infringement analysis?
The dissolution-aid limitation: the composition must have sodium lauryl sulfate as the dissolution aid.
2) Can a product infringe claim 1 without meeting the polymer list in claim 3?
Yes. Claim 3 is dependent on claim 1; polymer presence in the enumerated list is not required for claim 1.
3) Does claim 2 add a new excipient requirement beyond claim 1?
No. Claim 2 only adds the requirement that the formulation is orally administrable, while preserving claim 1’s API plus SLS dissolution-aid structure.
4) What is the practical effect of the solubility limit in claim 4?
It narrows a subset of compositions that meet water solubility <100 μg/mL at 25°C; it does not replace the broader claim 1 coverage.
5) What is the most direct formulation change to reduce risk under this patent?
Replace the dissolution aid so it is not sodium lauryl sulfate, because claim 1 ties dissolution aid identity to SLS.
References
- United States Patent 9,365,514. Claims provided in user prompt.
