Last Updated: September 24, 2026

Details for Patent: 8,853,197


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Which drugs does patent 8,853,197 protect, and when does it expire?

Patent 8,853,197 protects ZAYNICH and is included in one NDA.

This patent has twenty-two patent family members in seventeen countries.

Summary for Patent: 8,853,197
Title:Nitrogen containing compounds
Abstract:Compounds of Formula (I), their preparation and use in preventing or treating bacterial infection is disclosed.
Inventor(s):Mahesh Vithalbhai Patel, Prasad Keshav Deshpande, Satish Bhawasar, Sachin Bhagwat, Mohammad Alam Jafri, Amit MISHRA, Laxmikant Pavase, Sunil Gupta, Rajesh Kale, Sanjeev Joshi
Assignee: Wockhardt Ltd
Application Number:US14/294,364
Patent Claim Types:
see list of patent claims
Composition; Compound;
Patent landscape, scope, and claims:

United States Drug Patent 8,853,197: Claim Scope, Patent Strength and Generic Entry Risk

US Patent No. 8,853,197 protects a broad genus of trans-1,6-diazabicyclo[3.2.1]octane beta-lactamase inhibitor compounds, together with selected stereoisomers, salts and pharmaceutical compositions. The claims center on a 7-oxo-1,6-diazabicyclo[3.2.1]octane core bearing a substituted hydrazinocarbonyl group and an acidic or acid-functional substituent, particularly a sulfate ester.

The patent has meaningful chemical breadth in claim 1, but its practical enforcement value depends heavily on whether a marketed product contains one of the expressly claimed species in claims 2 through 6. Claims 5 and 6 are the narrowest and commercially most relevant species claims. Claims 7 through 14 protect compositions containing the claimed compounds, but they do not independently claim a method of treatment, dosing regimen, formulation technology or manufacturing process.

What compounds does US 8,853,197 protect?

The patent's principal subject matter is a class of substituted diazabicyclooctanone compounds. These compounds are structurally associated with beta-lactamase inhibition, particularly inhibition of serine beta-lactamases that can degrade beta-lactam antibiotics.

The core structural requirements are:

Claim element Scope
Core 1,6-Diazabicyclo[3.2.1]octane bearing a 7-oxo group
Configuration Formula I compounds and stereoisomers
R1 substituent Hydrogen, acyl-type group, or ester-type group
R2 substituent Sulfonate, sulfamide, phosphate, carboxymethyl, difluorocarboxymethyl, monofluorocarboxymethyl or trifluoromethyl
Salt coverage Pharmaceutically acceptable salts and cation-containing forms
Composition coverage Pharmaceutical compositions containing the claimed compounds
Species coverage Amino-acyl, cyclic amino-acyl, heteroaryl-acyl and related hydrazide derivatives

Claim 1 is a Markush claim. It does not identify one commercial compound. It covers a large chemical genus defined through alternative substituent lists for R1, R2, R3, R4, R5, R6 and R7.

The claim's central structural limitation is the combination of:

  1. A bridged diazabicyclooctanone scaffold.
  2. A substituted hydrazinocarbonyl group at the 2-position.
  3. An acidic or acid-functional group at the 6-position, including sulfate, sulfonamide, phosphate and carboxylic acid-related groups.

The claim is therefore broader than the individual examples in dependent claims 2 through 6. A compound can infringe claim 1 even if it is not one of the named compounds in those dependent claims, provided it falls within the Formula I variables.

How broad is claim 1 of US 8,853,197?

Claim 1 has substantial genus breadth, but the breadth is constrained by the defined Formula I structure and substituent dictionaries.

R1 scope

R1 may be hydrogen, an acyl-derived group or a carboxylate-derived group. The acyl option is particularly broad because R3 can be:

  • Hydrogen
  • Alkyl
  • Cyano
  • Amino
  • Amide
  • Urea
  • Aryl
  • Heteroaryl
  • Heterocyclyl
  • Cycloalkyl
  • Substituted cycloalkyl
  • OR8

The permitted substituents include halogen, hydroxyl or alkoxy groups, cyano, ester, amide, amino, sulfonamide-related groups, aryl groups and heterocyclic groups.

This creates coverage for many polar and ionizable side chains. The listed species demonstrate the intended chemical direction: pyrrolidine, piperidine, piperazine, morpholine, azetidine, amino acids, aminobutyric acid derivatives, amino-thiazole compounds and substituted cyclic amino-acyl groups.

R2 scope

R2 is narrower in type but important in product coverage. It includes:

  • SO3M
  • SO2NH2
  • PO3M
  • CH2COOM
  • CF2COOM
  • CHFCOOM
  • CF3

The sulfate option, SO3M, is prominent in the named species. The use of M as hydrogen or a cation permits free-acid and salt forms, including sodium salts.

The inclusion of carboxymethyl, difluorocarboxymethyl and monofluorocarboxymethyl groups expands the claim beyond sulfate analogs. A product with the same core and hydrazide side chain but a different acidic substituent could remain within claim 1.

R6 and R7 scope

R6 and R7 may be independently substituted or may join to form a four- to seven-membered ring. This ring-closing provision supports coverage of cyclic amines such as pyrrolidine, piperidine, piperazine and morpholine derivatives.

The ring option is commercially relevant because cyclic amino substituents can materially affect permeability, solubility, stability and beta-lactamase binding. It also increases the number of possible claimed compounds without requiring a separate claim for every ring system.

Which specific compounds are protected by claims 2 through 6?

Claims 2 through 6 narrow the broad Formula I genus to listed compounds or defined subclasses.

Claim Protected subject matter
Claim 2 A first group of sulfate ester compounds with amino-acyl and cyclic amino-acyl hydrazide substituents
Claim 3 A second group including sulfate, acetic acid and difluoroacetic acid analogs
Claim 4 Sodium salts of selected sulfate compounds, including cyano, morpholine, pyrrolidine and carboxamido derivatives
Claim 5 The trans compound with an (R)-piperidin-3-carbonyl hydrazide side chain
Claim 6 The trans compound with an (R)-pyrrolidin-3-carbonyl hydrazide side chain

Claims 5 and 6 are species claims. They are materially easier to evaluate against a specific drug substance than claim 1 because they identify the stereochemical configuration and side-chain identity.

Claim 5 covers:

trans-sulfuric acid mono-[2-(N′-[(R)-piperidin-3-carbonyl]-hydrazinocarbonyl)-7-oxo-1,6-diaza-bicyclo[3.2.1]oct-6-yl]ester

Claim 6 covers:

trans-sulfuric acid mono-[2-(N′-[(R)-pyrrolidin-3-carbonyl]-hydrazinocarbonyl)-7-oxo-1,6-diaza-bicyclo[3.2.1]oct-6-yl]ester

Each claim also covers stereoisomers and pharmaceutically acceptable salts. The salt language can be important for infringement analysis because a sodium, potassium or other pharmaceutically acceptable salt may still fall within the claim even though the isolated solid-state form differs from the free acid.

What pharmaceutical compositions are protected?

Claims 7 through 14 are composition claims. They cover pharmaceutical compositions containing:

  • Any claim 1 compound
  • Any claim 2 compound
  • Any claim 3 compound
  • Any claim 4 compound
  • The claim 5 piperidine species
  • The claim 6 pyrrolidine species

Claims 13 and 14 specifically identify compositions containing the claim 5 and claim 6 compounds.

These claims do not recite:

  • A beta-lactam antibiotic
  • A particular antibiotic-to-inhibitor ratio
  • Intravenous administration
  • Oral administration
  • A defined dosage
  • A particular excipient
  • A sustained-release or controlled-release system
  • A specific disease or pathogen
  • A method of treating infection

The composition claims are therefore broad as to formulation content but narrow as to the active compound. A generic manufacturer using a different active compound outside the Formula I scope would not infringe claims 7 through 14 merely because it used a similar pharmaceutical composition.

Does the patent protect a method of use?

No method-of-use claim appears in the provided claim set. The patent claims compounds and compositions only.

That distinction affects both enforcement and regulatory exclusivity. The claims do not expressly cover:

  • Treatment of bacterial infection
  • Treatment of carbapenem-resistant Enterobacterales
  • Treatment of infections caused by class A, class C or class D beta-lactamases
  • Combination therapy with meropenem, cefepime, piperacillin or another beta-lactam
  • Prophylactic use
  • A dosing schedule
  • A patient population

Any protection for therapeutic use would have to arise from separate method-of-treatment patents or from infringement by making, using, selling or importing the claimed compound or composition.

What formulations are protected by US 8,853,197?

The provided claims do not contain a detailed formulation limitation. Claims 7 through 14 require only a pharmaceutical composition comprising a covered compound.

Potentially covered dosage forms could include:

  • Injectable solutions
  • Injectable powders for reconstitution
  • Lyophilized products
  • Infusion products
  • Oral solid dosage forms
  • Oral liquid dosage forms
  • Pharmaceutical salts formulated with conventional excipients

The absence of a specific dosage-form limitation reduces the ability of a generic manufacturer to avoid the composition claims by changing excipients or presentation. A formulation redesign would not avoid infringement if the active compound remains within the claims.

At the same time, the patent does not appear to protect a specialized delivery system. A competitor could potentially avoid formulation overlap by using a nonclaimed active ingredient, even if the delivery technology is similar.

How strong is the patent estate?

The patent's strength is mixed and should be assessed claim by claim.

Dimension Assessment
Core scaffold coverage Strong if the accused compound uses the claimed diazabicyclooctanone structure
Genus breadth Broad, subject to written-description and enablement scrutiny
Species claims Stronger for the specifically identified piperidine and pyrrolidine compounds
Salt protection Meaningful, because pharmaceutically acceptable salts are expressly included
Stereochemical coverage Important and potentially restrictive in a stereochemically defined product
Formulation protection Broad in wording but dependent on use of the claimed active ingredient
Method-of-use protection None in the supplied claims
Manufacturing protection None in the supplied claims
Regulatory exclusivity Cannot be inferred from the patent claims alone
Design-around flexibility Moderate for side-chain, acidic-group and stereochemical changes

The most defensible infringement theory would generally focus on claims 5 or 6 when the accused active pharmaceutical ingredient matches one of those named stereochemical species. Claim 1 may provide a broader fallback position, but its extensive Markush structure creates more potential validity issues.

What invalidity issues could affect claim 1?

The principal validity risks for a broad chemical genus are predictable.

Written description

A challenger may argue that the specification does not demonstrate possession of the full range of compounds covered by every R1, R2 and R3 alternative. This issue becomes more significant where the claim includes multiple unrelated functional groups and ring systems.

Enablement

The breadth of claim 1 may require synthesis and testing of a large number of compounds. A challenger could argue that practicing the full genus requires undue experimentation, particularly if the specification provides limited examples for some substituent classes.

Anticipation

Earlier beta-lactamase inhibitor patents and publications may disclose overlapping diazabicyclooctane cores, sulfate groups, hydrazide substituents or specific cyclic amino-acyl side chains. Anticipation requires a single reference to disclose every claim element, including the required stereochemistry where applicable.

Obviousness

Obviousness risk is greater where prior art teaches:

  • The same diazabicyclooctanone scaffold
  • Sulfate or sulfamoyloxy substitution
  • Hydrazide or acylhydrazide side chains
  • Amino-acid-derived substituents
  • Beta-lactamase inhibitor activity for related compounds

Unexpected potency, improved stability, improved spectrum, reduced toxicity or superior beta-lactam synergy could support validity, but those facts must be tied to the claimed scope rather than isolated examples.

Claim construction

Terms such as "pharmaceutically acceptable salt," "stereoisomer," "optionally substituted" and the various functional-group definitions can become central in litigation. The prosecution history and specification definitions would determine whether these terms receive their ordinary meaning or a narrower patent-specific construction.

When does US 8,853,197 lose exclusivity?

The patent's enforceable term cannot be calculated reliably from the patent number and claims alone. The relevant date is generally the expiration of the patent term under 35 U.S.C. §154, adjusted for any applicable patent-term adjustment, terminal disclaimer or other recorded limitation. A patent's grant date does not establish its expiration date.

The patent may also be affected by:

  • Patent-term adjustment
  • Patent-term extension under 35 U.S.C. §156
  • Terminal disclaimers
  • Reexamination certificates
  • Post-grant claim cancellation
  • Continuation or divisional patents with overlapping subject matter

Patent expiration and FDA exclusivity are separate. A compound patent can remain enforceable after regulatory exclusivity ends, while an FDA exclusivity period can expire before the relevant patent term.

What is the Orange Book status?

No Orange Book listing can be established from the supplied claims alone. The claims identify a chemical genus and selected compositions but do not identify an approved drug, NDA, sponsor, active ingredient name or marketed brand.

If the patent is not associated with an FDA-approved drug product, it would not necessarily appear in the Orange Book. FDA listing depends on an approved NDA and the sponsor's patent submission. An unlisted patent can still be enforceable under ordinary patent law, but it would not necessarily generate an Orange Book Paragraph IV notice.

Are there Paragraph IV challenges or generic litigation?

No Paragraph IV challenge, ANDA litigation, settlement agreement or court disposition is established by the provided material.

A Paragraph IV case would require an ANDA applicant to certify that a listed patent is invalid, unenforceable or will not be infringed. The supplied claims do not identify:

  • An ANDA number
  • A generic applicant
  • A reference-listed drug
  • A Paragraph IV notice
  • A district-court action
  • A Hatch-Waxman settlement
  • A judgment or claim construction ruling

The absence of a method-of-use claim would also affect the likely certification posture if the patent were listed for an approved product. Compound and composition claims generally present more direct infringement issues than use claims because a generic active ingredient could infringe upon manufacture, importation or sale.

Which companies are likely relevant to the competitive landscape?

The technical field includes developers of diazabicyclooctane and other beta-lactamase inhibitors, including companies associated with avibactam, durlobactam, zidebactam and related investigational compounds. Those products are not automatically covered by US 8,853,197.

Chemical overlap must be tested against the actual molecular structure. Similar pharmacology or a shared beta-lactamase target is insufficient. In particular:

Competitor type Relevance to US 8,853,197
Avibactam products Requires structural comparison; shared DBO class alone does not establish infringement
Durlobactam products Requires analysis of the exact substituent and sulfate arrangement
Zidebactam programs Potentially relevant if the core, stereochemistry and side chains fall within Formula I
Cyclic boronate inhibitors Generally outside a diazabicyclooctanone claim unless structurally identical, which is unlikely
Non-DBO beta-lactamase inhibitors Usually outside the chemical claims
Generic manufacturers Risk depends on the precise active ingredient and salt form

The patent is therefore more relevant to structurally close DBO programs than to the broader beta-lactamase inhibitor market.

What generic launch scenarios exist?

Three principal scenarios apply.

Scenario 1: Exact species match

If a generic uses the claim 5 or claim 6 compound, infringement risk is high, subject to validity and enforceability defenses. A salt change is unlikely to provide a reliable design-around because the claims expressly include pharmaceutically acceptable salts.

Scenario 2: Same core, modified side chain

A compound with the same bridged core but a side chain outside the R1/R3 definitions may avoid literal infringement. The risk would then depend on whether the modified compound remains within claim 1 or raises a doctrine-of-equivalents issue.

Scenario 3: Different core or pharmacophore

A non-DBO inhibitor, a cyclic boronate or a different beta-lactamase inhibitor scaffold would generally present lower literal infringement risk. Separate patent estates could still apply.

The most effective design-around targets are likely to be the hydrazinocarbonyl linkage, the 6-position acidic substituent, the trans stereochemistry and the defined cyclic amino-acyl side chains. Each modification requires a full claim chart against claim 1, not only claims 5 and 6.

Does the patent create a manufacturing or licensing barrier?

The supplied claims contain no manufacturing-process claims. They do not cover:

  • A particular synthetic intermediate
  • A resolution process
  • A crystallization process
  • A fermentation process
  • A purification method
  • A polymorph
  • A hydrate or solvate
  • A specific synthetic route

The commercial barrier is therefore primarily product-based. A license would be most relevant for a program whose active ingredient falls within claim 1 or one of the named species claims.

A complete freedom-to-operate review would also need to assess related continuation, divisional and foreign-family patents, as well as later patents directed to salts, polymorphs, formulations, combinations, manufacturing processes and clinical uses. Those rights are separate from the claim set supplied here.

Key Takeaways

  • US 8,853,197 is a compound and composition patent focused on substituted trans-1,6-diazabicyclo[3.2.1]octanone beta-lactamase inhibitors.
  • Claim 1 is a broad Markush genus covering multiple acidic groups, amino-acyl substituents, cyclic amines and stereochemical forms.
  • Claims 5 and 6 provide the clearest protection for the specifically identified (R)-piperidin-3-carbonyl and (R)-pyrrolidin-3-carbonyl species.
  • Claims 7 through 14 cover pharmaceutical compositions but do not claim a specific formulation, antibiotic combination, dosage or method of treatment.
  • The patent contains no supplied manufacturing or method-of-use claims.
  • Salt and stereoisomer language increases product-level infringement risk for structurally matching generic products.
  • No Orange Book listing, Paragraph IV challenge, litigation, settlement or approved-product association is established by the supplied information.
  • Generic design-around opportunities focus on the core, hydrazide linkage, acidic substituent, stereochemistry and amino-acyl side chain.
  • Patent-term expiration must be determined from the official patent record and any recorded term adjustment, extension or disclaimer.

FAQs

Is US 8,853,197 an avibactam patent?

The supplied claims do not establish that the patent covers avibactam. Structural identity must be determined by comparing avibactam's complete molecular structure with Formula I and the issued claims.

Does changing the sodium salt avoid the patent?

Not necessarily. Claims 1 through 6 expressly include pharmaceutically acceptable salts, and claim 4 specifically identifies sodium salts. A different salt could remain within the claims.

Does the patent cover combinations with meropenem?

The supplied claims do not expressly require or claim meropenem or another beta-lactam antibiotic. A combination product could still infringe if it contains a claimed compound, but the claims do not independently protect the antibiotic combination.

Can a generic use a different stereoisomer?

A different stereoisomer may avoid a narrow species claim if the claim requires a particular configuration. It may still fall within claim 1 if the claim's stereoisomer language and Formula I structure encompass it.

Is a formulation patent needed to block generic entry?

No. A valid compound claim can block manufacture, sale or importation of a matching active ingredient without a separate formulation patent. A formulation patent would provide additional protection for a specific dosage form or composition.

References

  1. United States Patent and Trademark Office. (2014). United States Patent No. 8,853,197.
  2. 35 U.S.C. § 154. Patent term.
  3. 35 U.S.C. § 156. Extension of patent term.
  4. U.S. Food and Drug Administration. (n.d.). Approved drug products with therapeutic equivalence evaluations.
  5. Leahy-Smith America Invents Act, Pub. L. No. 112-29, 125 Stat. 284 (2011).

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Drugs Protected by US Patent 8,853,197

Applicant Tradename Generic Name Dosage NDA Approval Date TE Type RLD RS Patent No. Patent Expiration Product Substance Delist Req. Patented / Exclusive Use Submissiondate
Wockhardt Bio Ag ZAYNICH cefepime hydrochloride; zidebactam POWDER;INTRAVENOUS 220787-001 May 29, 2026 RX Yes Yes ⤷  Start Trial ⤷  Start Trial Y ⤷  Start Trial
>Applicant >Tradename >Generic Name >Dosage >NDA >Approval Date >TE >Type >RLD >RS >Patent No. >Patent Expiration >Product >Substance >Delist Req. >Patented / Exclusive Use >Submissiondate

International Family Members for US Patent 8,853,197

Country Patent Number Estimated Expiration Supplementary Protection Certificate SPC Country SPC Expiration
Australia 2012303691 ⤷  Start Trial
Brazil 112013028813 ⤷  Start Trial
Canada 2833241 ⤷  Start Trial
China 103619843 ⤷  Start Trial
Denmark 2748165 ⤷  Start Trial
European Patent Office 2748165 ⤷  Start Trial
>Country >Patent Number >Estimated Expiration >Supplementary Protection Certificate >SPC Country >SPC Expiration

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