Details for Patent: 9,266,895

Which drugs does patent 9,266,895 protect, and when does it expire?

Patent 9,266,895 protects WAYRILZ and is included in one NDA.

This patent has forty-two patent family members in thirty countries.

Summary for Patent: 9,266,895

Title:	Substituted pyrazolo[3,4-d]pyrimidines as kinase inhibitors
Abstract:	The present disclosure provides compounds of Formula (IA) and or pharmaceutically acceptable salts thereof that are tyrosine kinase inhibitors, in particular BTK, and are potentially useful for the treatment of diseases treatable by inhibition of tyrosine kinases such as cancer, inflammatory diseases such as arthritis, and the like. Also provided are pharmaceutical compositions containing such compounds and/or pharmaceutically acceptable salts thereof and processes for preparing such compounds and pharmaceutically acceptable salts thereof.
Inventor(s):	Tim Owens, Erik Verner
Assignee:	Principia Biopharma Inc
Application Number:	US14/374,788
Patent Claim Types: see list of patent claims	Use; Composition;

Scope & Claims Analysis for US Patent 9,266,895 (Formula IA Bruton's Tyrosine Kinase Inhibitors)
US 9,266,895 is a broad US composition-of-matter patent centered on “Formula (IA)” compounds that inhibit Bruton's tyrosine kinase (BTK). The independent claim is a generic genus claim over a large set of substituent options (primarily the “Rc” substituent variation and multiple heterocycle/amine embodiments), followed by narrower dependent claims that (1) enumerate specific “Rc” subclasses, (2) lock the invention onto large preselected lists of stereoisomers and named compounds, (3) include salt forms, and (4) cover a pharmaceutical composition and a method of inhibiting BTK.

What does US 9,266,895 claim at a high level?

Featured-snippet answer: US 9,266,895 claims BTK-inhibiting compounds defined by a large chemical “Formula (IA)” genus, with the core scope driven by variation of the “Rc” substituent and multiple heterocycle and stereochemical embodiments, plus pharmaceutically acceptable salts, formulations, and methods of inhibiting BTK in patients.

What is the claim type mix?

• Independent claim 1: A compound of Formula (IA) (genus) with explicit definition of a substituent variable labeled “Rc” and the rest of the Formula (IA) framework captured by the patent’s earlier formula definitions (not provided in full here, but the provided text shows the Rc-dependent portion is the main degree of freedom).
• Dependent claims 2–4: Narrowed genus subsets by specifying which Rc variants are permitted.
• Dependent claims 5–8: Specific named compounds and stereoisomer/mix combinations, still within the same overall scaffold but locking in precise stereochemistry, ring substituents, and Rc choices from the listed families.
• Dependent claim 9: Pharmaceutical composition claim covering the active compound(s) + excipient.
• Dependent claim 10: Method of use claim for inhibiting BTK by administering the claimed pharmaceutical composition to a patient.

Which substituent positions drive infringement risk (Rc and related variants)?

Featured-snippet answer: In US 9,266,895, scope is primarily determined by which chemical group is placed at the “Rc” position (including multiple piperazine and spirocyclic amine options and oxetane-bearing variants), with further narrowing when claims 2–4 specify particular Rc lists and when claims 5–8 name individual stereoisomers.

Rc = substituted piperazine families (claims 1–4)

The provided claim text makes clear that “Rc” includes multiple structural families. The most consequential, because they are enumerated, are:

1. Tert-butyl-free “C(CH3)2-(4-R4-piperazin-1-yl)” family (Rc type a)

   • Rc: —C(CH3)2-(4-R4-piperazin-1-yl)
   • R4 options: hydrogen, alkyl, alkoxyalkyl, haloalkyl, alkylsulfonyl, alkoxycarbonyl, acyl, or oxetan-3-yl
   • Piperazinyl ring optionally substituted with one or two alkyl.

2. 3-oxo substituted piperazinyl family (Rc type b)

   • Rc: —C(CH3)2-(3-oxo-4-Ra-piperazin-1-yl)
   • Ra options: hydrogen, alkyl, cycloalkyl, alkoxyalkyl, haloalkyl, or oxetan-3-yl
   • Piperazinyl ring optionally substituted with one or two alkyl.

3. Oxetane-3-yl amide-like linkage family (Rc type c)

   • Rc: —C(CH3)2—NRboxetan-3-yl
   • Rb options: hydrogen, alkyl, alkoxyalkyl, or cycloalkyl.

4. Nitrogen-rich bicyclic/aza-substituted ring family (Rc type d)

   • Rc: —C(CH3)2—Rd
   • Rd defined as a ring with one or two of X1, X2, X3 are nitrogen and the rest are carbon, with optional substitution by one or two alkyl/haloalkyl/halo substituents.

5. Spirocyclic oxygen-nitrogen rings and morpholine alternatives (Rc type e)

   • Rc options include:
     • —C(CH3)2-2-oxa-6-azaspiro[3.3]heptan-6-yl
     • —C(CH3)2—CH2morpholin-4-yl
       (The claim text repeats these alternatives, but the substantive scope is the same: these are alternative Rc ring systems.)

How the dependent claims narrow Rc

• Claim 2: explicitly enumerates numerous Rc selections (e.g., piperazinyl with hydrogen, methyl, ethyl, methylsulfonyl, 3-oxo variants, oxetan-3-yl, methoxyethyl, tert-butyl, acetyl, trifluoroethyl, isopropyl, multiple dimethyl/trimethyl positional isomers, etc.; plus spiro/morpholine in the list).
• Claims 3 and 4: further enumerate additional Rc subsets, with claim 3 emphasizing a particular subset (e.g., 3-oxo-4-methylpiperazin-1-yl, 4-(2-methoxyethyl)piperazin-1-yl, 4-tert-butylpiperazin-1-yl, 4-isopropylpiperazin-1-yl, multiple methyl positional variants, oxetan-3-ylpiperazin-1-yl, methoxycarbonylpiperazin-1-yl, and 2-oxa-6-azaspiro[…] entries). Claim 4 again enumerates overlapping but not identical Rc options including the spirocyclic and a smaller piperazine set.

In practical infringement terms: a design-around that changes the scaffold but keeps the same overall Formula (IA) core could still fall under claim 1 if Rc is still within the claim-1 Rc definition. A more meaningful design-around is to move Rc to a group outside all five Rc categories and outside the enumerated claim-2/3/4 sets.

How broad is claim 1 versus the named-compound dependent claims?

Claim 1: genus scope

Claim 1 is a genus claim: it covers “a compound of Formula (IA)” with any Rc matching the set of allowed structural patterns (a) through (e) plus pharmaceutically acceptable salts.

Key breadth drivers visible in the text:

• Multiple Rc families (piperazine, 3-oxo piperazine, oxetane-linked amine, nitrogen-containing ring system, spirocyclic oxygen-nitrogen ring, morpholine).
• In multiple families, Rc has variable substituents (e.g., R4 options and optional alkyl substitution on the piperazine ring; for type b, Ra options similarly expand).
• Salts are included.

Claims 2–4: enumerated subsets (intermediate breadth)

Claims 2–4 retain Formula (IA) but narrow by specifying that Rc must be one of an explicit set of options. This is important in freedom-to-operate (FTO) work because it can make the search space discrete: the infringing compounds are likely those with Rc drawn from those lists.

Claims 5–8: high-specificity capture (named stereoisomers and mixtures)

Claims 5–8 include long enumerations of particular compounds. The dependency structure indicates that if a competitor’s product matches any listed named compound (including stereochemistry), it falls within those dependent claims.

What these dependent claims do:

• Pin stereochemical configurations such as (2S)/(2R), (3R)/(3S), (R)/(S), and mixtures like (2 RS), (E) or (Z).
• Lock in specific Rc instances such as:
  • 4-methylpiperazin-1-yl
  • 4-ethylpiperazin-1-yl
  • oxetan-3-yl piperazin-1-yl
  • spiro 2-oxa-6-azaspiro[3.3]heptan-6-yl
  • hexahydropyrazino[2,1-c][1,4]oxazin… substituted moieties (in the list)
  • morpholine-related embodiments (if present in named examples)

Net effect: even if claim 1 is broad, claims 5–8 create a second infringement hook based on specific stereochemical products and mixtures typically seen in development programs.

What do claims 9 and 10 add (composition and BTK method of use)?

Claim 9: pharmaceutical composition

Claim 9 covers:

• A pharmaceutical composition comprising a compound of any one of claims 1 to 5, 6, 7, and 8 (so it incorporates both the genus and the named stereochemical dependent sets)
• Plus a pharmaceutically acceptable excipient.

This matters because it captures formulation-level submissions even when actives are the same.

Claim 10: method of inhibiting BTK

Claim 10 covers:

• A method of inhibiting BTK activity in a patient
• By administering a therapeutically effective amount of the claimed pharmaceutical composition.

This is the regulatory-relevant “use” patent layer typically asserted against ANDA filers only where product label/use overlaps with BTK inhibition indications and the claimed administration language.

How would an accused product map to the claims (claim chart logic)?

Accused product mapping (high-level):

1. Determine whether the active ingredient fits Formula (IA).
2. Identify whether the active ingredient’s Rc matches any of:
   • the structural patterns in claim 1 (types a–e), or
   • any enumerated Rc options in claims 2–4, and/or
   • any listed named stereoisomers/mixtures in claims 5–8.
3. If the active fits, check for:
   • salt form (explicitly included),
   • formulation composition (claim 9),
   • BTK inhibition administration in a patient (claim 10).

Design-around implication: “Rc” is the lever. Changes to piperazine substituent identity, ring substitution patterns, oxetane link placement, or replacement of the spiro/morpholine ring system with a structurally different amine core would be the main routes to escape claim 1’s Rc definition.

Claim-by-claim scope summary table

Claim	Coverage type	Main scope limiter in provided text	Practical freedom-to-operate consequence
1	Independent genus	Rc defined by 5 structural types (a)-(e)	Broadest infringement hook; design-around must exit all Rc patterns.
2	Dependent narrower	Rc explicitly enumerated list of many piperazine/spiro variants	Reduces ambiguity; can target known competitor Rc choices.
3	Dependent narrower	Another enumerated Rc subset list	Further narrows; overlaps with claim 2 but not identical.
4	Dependent narrower	Another Rc list including piperazine and spiro	Captures additional variants not in claims 2/3.
5	Dependent named compounds	Large list of specific stereoisomers and mixtures; salts and E/Z stereochemistry included	Strongest hook when competitor’s API matches a listed named stereoisomer.
6	Dependent named compounds (subset/list)	Similar named stereo/mix capture	Additional discrete capture set.
7	Dependent mixture	3R/3S piperidine-linked named compounds mixture	Captures marketed stereomixtures.
8	Dependent mixture	R/S mixture for oxetan-3-yl piperazinyl variants	Captures specific oxetane-bearing stereoisomer mixtures.
9	Dependent composition	any compound of claims 1–8 + pharmaceutically acceptable excipient	Captures formulation level.
10	Dependent method of use	administering to inhibit BTK	Adds use-based risk for label/indication overlaps.

Patent landscape considerations specifically for this patent (what the claim structure implies)

Featured-snippet answer: The estate built into this claim set is typical of BTK inhibitor scaffold families: broad genus claim 1 plus dependent enumerations that create multiple product-specific hooks (stereoisomers, E/Z variants, and mixture claims), then formulation and BTK use claims. This structure increases enforcement leverage against both API and drug product versions.

What the claim drafting suggests about enforcement posture

• Claim 1 provides the “catch-all” in claim construction.
• Claims 2–4 allow targeted rebuttal or assertion without litigating every substitution possibility.
• Claims 5–8 allow enforcement on a product-by-product basis using stereochemistry and named compound identity.

Key Takeaways

• US 9,266,895 is a BTK inhibitor chemical genus patent centered on Formula (IA) with scope dominated by the Rc substituent definition (piperazine variants, 3-oxo piperazine variants, oxetane-3-yl-linked amine variants, a nitrogen-containing ring alternative, and spiro/morpholine Rc alternatives).
• Dependent claims 2–4 enumerate Rc subsets, while claims 5–8 enumerate specific stereoisomeric compounds and mixtures, creating strong product-specific infringement pathways.
• The patent adds composition-of-matter formulation coverage (claim 9) and BTK inhibition method-of-use coverage (claim 10), expanding litigation targets beyond the API.

FAQs

1) What part of US 9,266,895 is most likely to drive claim construction in litigation?
Rc (the “Rc” substituent definition and its enumerated subsets in claims 2–4) and the stereochemical/mixture lists in claims 5–8.

2) Do the claims cover pharmaceutically acceptable salts?
Yes. Claim 1 includes salts, and dependent compounds (claims 5–8) reference salts as “and/or a pharmaceutically acceptable salt thereof.”

3) Is there protection for specific stereoisomers and E/Z isomers?
Yes. Claims 5–6 include individual (2S)/(2R)/(3R)/(3S)/(R)/(S) entities, mixture stereoisomers (e.g., (2 RS)), and E/Z stereoisomer inclusion.

4) Does the patent cover formulations (tablets/capsules/suspensions) or only active ingredients?
It covers pharmaceutical compositions in claim 9 with pharmaceutically acceptable excipients.

5) Does it also claim the therapeutic method?
Yes. Claim 10 claims methods of inhibiting BTK by administering the claimed compositions to patients.

References

1. US Patent 9,266,895, “Compounds and methods for inhibiting Bruton's tyrosine kinase activity,” claim text as provided.

Drugs Protected by US Patent 9,266,895

Applicant	Tradename	Generic Name	Dosage	NDA	Approval Date	TE	Type	RLD	RS	Patent No.	Patent Expiration	Product	Substance	Delist Req.	Patented / Exclusive Use	Submissiondate
Genzyme Corp	WAYRILZ	rilzabrutinib	TABLET;ORAL	219685-001	Aug 29, 2025		RX	Yes	Yes			Y	Y		METHOD OF INHIBITING BRUTON'S TYROSINE KINASE ACTIVITY IN ADULT PATIENTS WITH PERSISTENT OR CHRONIC IMMUNE THROMBOCYTOPENIA (ITP) WHO HAVE HAD AN INSUFFICIENT RESPONSE TO A PREVIOUS TREATMENT

International Family Members for US Patent 9,266,895

Country	Patent Number	Estimated Expiration	Supplementary Protection Certificate	SPC Country	SPC Expiration
European Patent Office	3181567		C20260015	Finland
European Patent Office	3181567		301380	Netherlands
European Patent Office	3181567		CR 2026 00022	Denmark
European Patent Office	3181567		PA2026520	Lithuania
European Patent Office	3181567		LUC50052	Luxembourg
Australia	2013312296
Brazil	112015003859