Details for Patent: 7,579,449

Which drugs does patent 7,579,449 protect, and when does it expire?

Patent 7,579,449 protects SYNJARDY XR, TRIJARDY XR, GLYXAMBI, JARDIANCE, and SYNJARDY, and is included in five NDAs.

Protection for SYNJARDY XR has been extended six months for pediatric studies, as indicated by the *PED designation in the table below.

This patent has seventy-four patent family members in thirty-six countries.

Summary for Patent: 7,579,449

Title:	Glucopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture
Abstract:	Glucopyranosyl-substituted benzene derivatives of general formula I where the groups R1 to R6 as well as R7a, R7b, R7c are defined herein and the tautomers, the stereoisomers thereof, the mixtures thereof and the salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.
Inventor(s):	Matthias Eckhardt, Peter Eickelmann, Frank Himmelsbach, Edward Leon Barsoumian, Leo Thomas
Assignee:	Boehringer Ingelheim International GmbH
Application Number:	US11/080,150
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 7,579,449
Patent Claim Types: see list of patent claims	Compound;

United States Patent 7,579,449: Scope, Claim Coverage, and U.S. Landscape

What does US 7,579,449 claim?

US Drug Patent 7,579,449 claims glucopyranosyl-substituted benzene derivatives defined by a generic scaffold (Formula I) plus a set of narrowed dependent claims and explicit individual chemical embodiments.

Core claim set (independent + dependent)

• Claim 1 is the broadest: compounds of general formula I with constrained substituent sets for R1–R7a/R7b/R7c and R2, R3, R4, R5, R6.
• Claims 2–13 narrow Claim 1 by fixing specific substituent selections (examples: R1 = methyl or chlorine; R3 = ethynyl; R3 = trimethylsilylethyl; R3 = cycloalkyloxy; specific choices for R2, R4/R5, and R6).
• Claims 14–25 identify specific named chemical structures as distinct embodiments.

Practical claim architecture

Claim 1 defines a combinatorial space across three main “handles”:

1. A glucopyranosyl-substituted benzene ring system (the sugar is fixed as β-D-glucopyranos-1-yl).
2. A benzyl linkage to a second substituted benzene ring through a defined substitution pattern (visible in the explicitly named claims).
3. A controlled substituent set at R3 that includes multiple electron-rich/heteroatom and cyclic ether/heterocycle ether and ethynyl-anchored options.

What is the scope of Claim 1 (Formula I) in business terms?

Claim 1 covers glucopyranosyl-substituted benzene derivatives of general formula I with these key restrictions:

Substituent constraints in Claim 1

R1 (on the benzene system):

• Allowed: H, F, Cl, Br, CN, methyl, ethyl, isopropyl, ethynyl, hydroxy, methoxy, ethoxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy

R2:

• Allowed: H, F, hydroxy, methoxy, ethoxy, methyl

R3 (the most composition-defining group):

• Allowed:
  • trimethylsilylethyl
  • ethynyl
  • 2-hydroxyprop-2-ylethynyl
  • 2-methoxyprop-2-ylethynyl
  • 3-hydroxy-1-propyn-1-yl
  • 3-methoxy-1-propyn-1-yl
  • cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy
  • tetrahydrofuran-3-yloxy, tetrahydropyran-4-yloxy
  • piperidin-4-yloxy
  • N-methylpiperidin-4-yloxy
  • N-acetylpiperidin-4-yloxy

R4, R5 (independent):

• Allowed: H or F

R6:

• Allowed: H, (C1-6-alkyl)carbonyl, (C1-6-alkyl)oxycarbonyl

R7a, R7b, R7c:

• Allowed: H (no additional substitution allowed at these positions)

Stated tolerance:

• Includes stereoisomers, mixtures, and salts unless otherwise stated.

What this means for breadth

• Sugar anchoring is fixed as glucopyranosyl (β-D in named examples), which limits claims versus fully variable glycosyl moieties.
• A wide hetero-/halo substitution set for aromatic positions exists, especially R1 and R2, giving latitude for electronics and solubility tuning.
• R3 is the primary “design axis”. Claim 1 includes both:
  • ethynyl/alkynyl variants and
  • cyclic ether/heterocyclic ether variants including THF-3-yloxy, THP-4-yloxy, and piperidine-4-yloxy derivatives.
• R4/R5 are heavily restricted (only H or F), which limits substitution pattern escape.

How do Claims 2–13 narrow the combinatorial space?

These dependent claims lock in particular choices that map closely to common medicinal chemistry series.

Claim-by-claim narrowing (high signal)

Claim	Fixed limitation	Practical impact on scope
2	R1 is methyl or chlorine	Narrows aromatic substituent diversity to a 2-member set
3	R3 is ethynyl	Focuses on a direct alkynyl handle
4	R3 is trimethylsilylethyl	Covers protected alkynyl precursor-like motif
5	R3 is cyclobutyloxy	Locks R3 to a small cyclic ether
6	R3 is cyclopentyloxy	Locks R3 to larger cyclic ether
7	R3 is cyclohexyloxy	Locks R3 to larger cyclic ether
8	R3 is tetrahydrofuran-3-yloxy	Locks R3 to THF-derived oxygen substituent
9	R3 is tetrahydropyran-4-yloxy	Locks R3 to THP-derived oxygen substituent
10	R2 is H or methyl	Limits second ring substituent
11	R2 is H	Removes methyl option
12	R4 and R5 are H	Removes fluorine option
13	R6 is H	Removes carbonyl/alkoxycarbonyl options

Relationship to Claim 1

Claims 2–13 are additive constraints. If a compound matches Claim 1 and also matches one of these fixed selections, it falls into those dependent claim scopes too. The real-world coverage is therefore Claim 1 breadth plus a ladder of narrower “claim-strong” embodiments.

Which specific molecules are explicitly claimed (Claims 14–25)?

Claims 14–25 provide concrete compositions that often function as:

• exemplified targets for enforcement,
• fallback positions for validity if the genus is attacked.

Explicitly named claim embodiments

Claim	Structure name (as provided)	Key locked features
14	1-Chloro-2-(4-cyclopentyloxybenzyl)-4-(β-D-glucopyran-1-yl)-benzene	Chloro; cyclopentyloxy-benzyl; glucopyranosyl at specified position
15	1-Chloro-4-(β-D-glucopyran-1-yl)-2-[4-((R)-tetrahydrofuran-3-yloxy)-benzyl]-benzene	THF-3-yloxy; chiral R designation
16	1-Chloro-4-(β-D-glucopyran-1-yl)-2-[4-((S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene	THF-3-yloxy; opposite enantiomer S
17	1-Chloro-4-(β-D-glucopyran-1-yl)-2-(4-cyclobutyloxy-benzyl)-benzene	cyclobutyloxy-benzyl
18	1-Chloro-4-(β-D-glucopyran-1-yl)-2-(4-cyclohexyloxy-benzyl)-benzene	cyclohexyloxy-benzyl
19	1-Chloro-4-(β-D-glucopyran-1-yl)-2-[4-(tetrahydropyran-4-yloxy)-benzyl]-benzene	THP-4-yloxy-benzyl
20	1-Chloro-4-(β-D-glucopyran-1-yl)-2-[4-(1-acetyl-piperidin-4-yloxy)-benzyl]-benzene	N-acetylpiperidin-4-yloxy variant
21	1-(β-D-Glucopyranos-1-yl)-4-methyl-3-[4-(2-trimethylsilyl-ethyl)-benzyl]-benzene	Trimethylsilylethyl-benzyl
22	1-Chloro-4-(β-D-glucopyran-1-yl)-2-(4-ethynyl-benzyl)-benzene	Ethynyl-benzyl
23	1-Fluoro-4-(β-D-glucopyran-1-yl)-2-(4-ethynyl-benzyl)-benzene	Fluoro analog of Claim 22
24	1-(β-D-Glucopyranos-1-yl)-3-(4-ethynyl-benzyl)-benzene	Loss of halogen at that position
25	1-Methoxy-4-(β-D-glucopyran-1-yl)-2-(4-ethynyl-benzyl)-benzene	Methoxy variant of the ethynyl-benzyl series

What these explicit claims signal

The claim set concentrates on:

• chloro/fluoro/methyl/methoxy substitutions on the glucopyranosyl-bearing ring,
• benzyl-linked para-substituted aromatic rings with either cyclic ether, ethynyl, or trimethylsilylethyl groups,
• enantiomer-specified coverage for at least one THF-3-yloxy benzyl system (Claims 15–16).

That pattern often correlates with a lead optimization campaign where the benzyl aryl substituent (para-oxygenated ring or para-ethynyl ring) is the medicinal chemistry lever.

Where does the patent sit in the U.S. patent landscape (scope/coverage map)?

With only the provided claim text, the enforceable landscape for US 7,579,449 can be mapped at a claim-scope level (not by citing other patents, since no bibliographic record, assignee, priority, or related family members were provided).

In-patent landscape: “genus + enumerated species” pattern

• Genus coverage: Claim 1 covers a large set of compounds built on the same core scaffold and substitution constraints.
• Species coverage: Claims 14–25 enumerate specific R1/R2/R3 combinations and lock stereochemistry for at least one R3 benzyl-THF system.

Practical infringement/clearance “design lanes”

Competitors seeking freedom-to-operate against US 7,579,449 will most often evaluate whether their candidates fall into one of these inclusion corridors:

1. R3 is one of the enumerated ether groups or alkynyl groups (ethynyl, trimethylsilylethyl, cyclic ethers, THF/THP ether variants, piperidinyl ether variants).
2. Sugar is a glucopyranosyl substituent in the claimed manner (β-D glucopyranose indicated in the named examples and consistent with Claim 1’s “glucopyranosyl-substituted” language).
3. Aromatic halogen positions comply with R4/R5 (H or F) and R6 constraints.

Small changes outside these exact sets (for example, changing R3 to a non-listed substituent type) are often the difference between inclusion and exclusion.

What is the effective claim “surface area” for enforcement?

Highest-probability enforcement zone

• Compounds that match Claim 1 and simultaneously match at least one “tight” dependent parameter combination in Claims 2–13, or match one of the explicit numbered compounds in Claims 14–25.

Highest-probability species-level targets

• The explicit named compounds (Claims 14–25) because they are single-compound claim entries with no need to argue that a competitor’s compound fits an expansive Markush-like parameter range.

Potential overlap with typical competitor design strategies (within Claim text constraints)

Based strictly on the provided claim elements, the most salient competitor “escape hatches” in chemistry terms are those that violate one of the rigid enumerations:

• R3 not equal to the listed groups (the broadest escape for R&D teams).
• R4/R5 not equal to H or F (claim restriction at those positions).
• R6 not equal to H or permitted carbonyl/alkoxycarbonyl format.
• R7a/R7b/R7c not all hydrogen.
• Non-glucopyranosyl glycosylation or different sugar anomer/attachment pattern (the claim language is sugar-form specific).

Key Takeaways

• US 7,579,449 is structured as a genus patent (Claim 1) covering glucopyranosyl-substituted benzene derivatives with strict limits on R1–R7a/R7b/R7c, with the largest chemical variability anchored on R1/R2 and especially R3.
• Claims 2–13 create a narrowing ladder by fixing key substituent choices, with multiple options focused on alkynyl (ethynyl, trimethylsilylethyl) and cyclic ether/heterocycle ether R3 groups.
• Claims 14–25 enumerate specific structures, including two enantiomer-specific THF-3-yloxy benzyl examples (Claims 15–16) and multiple ethynyl-benzyl and cyclic ether-benzyl variants.
• For clearance and enforcement, the decisive axis is whether a candidate matches:
  • the glucopyranosyl scaffold, and
  • R3 membership in the claimed set, while also obeying R4/R5 (H/F) and R6 (H or permitted carbonyl/alkoxycarbonyl).

FAQs

1. Is Claim 1 a Markush-style genus?
   Yes. Claim 1 uses a “general formula I” with enumerated substituent options for R1–R7a/R7b/R7c and additional fixed value constraints for R4/R5 and R6.

2. Which substituent most controls inclusion across the claim family?
   R3. It lists a defined set of alkynyl and ether/heterocycle ether substituent groups and drives the major structure differences between the enumerated embodiments.

3. Do the claims cover stereoisomers?
   Yes, Claim 1 expressly includes stereoisomers and mixtures. In addition, Claims 15 and 16 separately claim the R and S versions of a THF-3-yloxy benzyl system.

4. Are halogen and fluorine permitted throughout the scaffold?
   Chlorine is common in the explicit examples, and Claim 1 allows fluorine in multiple roles: R1 includes fluorine, and R4/R5 can be H or F.

5. Do Claims 14–25 function as narrower fallback positions?
   Yes. They are explicit compound claims that reduce reliance on parameter matching and provide direct enforcement targets for the specific structures listed.

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References

[1] United States Patent 7,579,449 (claims as provided by user).

Drugs Protected by US Patent 7,579,449

Applicant	Tradename	Generic Name	Dosage	NDA	Approval Date	TE	Type	RLD	RS	Patent No.	Patent Expiration	Product	Substance	Delist Req.	Patented / Exclusive Use	Submissiondate
Boehringer Ingelheim	SYNJARDY XR	empagliflozin; metformin hydrochloride	TABLET, EXTENDED RELEASE;ORAL	208658-001	Dec 9, 2016		RX	Yes	No	7,579,449*PED				Y
Boehringer Ingelheim	SYNJARDY XR	empagliflozin; metformin hydrochloride	TABLET, EXTENDED RELEASE;ORAL	208658-002	Dec 9, 2016		RX	Yes	No	7,579,449*PED				Y
Boehringer Ingelheim	SYNJARDY XR	empagliflozin; metformin hydrochloride	TABLET, EXTENDED RELEASE;ORAL	208658-003	Dec 9, 2016		RX	Yes	No	7,579,449*PED				Y
Boehringer Ingelheim	SYNJARDY XR	empagliflozin; metformin hydrochloride	TABLET, EXTENDED RELEASE;ORAL	208658-004	Dec 9, 2016		RX	Yes	Yes	7,579,449*PED				Y
Boehringer Ingelheim	TRIJARDY XR	empagliflozin; linagliptin; metformin hydrochloride	TABLET, EXTENDED RELEASE;ORAL	212614-001	Jan 27, 2020		RX	Yes	No	7,579,449*PED				Y
Boehringer Ingelheim	TRIJARDY XR	empagliflozin; linagliptin; metformin hydrochloride	TABLET, EXTENDED RELEASE;ORAL	212614-002	Jan 27, 2020		RX	Yes	No	7,579,449*PED				Y

Foreign Priority and PCT Information for Patent: 7,579,449

Foriegn Application Priority Data
Foreign Country	Foreign Patent Number	Foreign Patent Date
Germany	10 2004 012 676	Mar 16, 2004
Germany	10 2004 040 168	Aug 18, 2004
Germany	10 2004 061 145	Dec 16, 2004
	05002628	Feb 9, 2005

International Family Members for US Patent 7,579,449

Country	Patent Number	Estimated Expiration	Supplementary Protection Certificate	SPC Country	SPC Expiration
European Patent Office	1730131		62/2014	Austria
European Patent Office	1730131		C300696	Netherlands
European Patent Office	1730131		PA2014035	Lithuania
European Patent Office	1730131		92555	Luxembourg
European Patent Office	1730131		CA 2014 00054	Denmark
European Patent Office	1730131		1490061-7	Sweden