Last updated: February 19, 2026
This report analyzes China patent CN105597206, titled "Preparation method of a substituted 1,5-diketone and its application" (中文名称: “取代的1,5-二酮的制备方法及其应用”). The patent, filed on January 15, 2015, by ZHU, Pengsheng, and granted on May 18, 2016, covers a specific preparation method for a class of substituted 1,5-diketones and their potential applications. The disclosed compound class is represented by general formula (I) in the patent document.
What is the Core Invention of CN105597206?
The patent's core invention is a novel and efficient method for synthesizing substituted 1,5-diketones. These compounds possess a 1,5-diketone structure with various substituents at specific positions, which are claimed to be valuable intermediates for pharmaceutical synthesis. The patent emphasizes an improved process that aims for higher yields and purities compared to existing methods.
What are the Key Claims of CN105597206?
The patent's claims define the legal boundaries of the invention. CN105597206 includes independent and dependent claims covering the preparation method and the resulting compounds.
Claim 1: The Preparation Method
Independent Claim 1 outlines the specific process for synthesizing the substituted 1,5-diketones. The general reaction scheme involves reacting specific starting materials under defined conditions. Key aspects of this claim typically include:
- Reactants: Identification of the precise chemical structures or classes of compounds used as starting materials. This often involves specific aldehydes, ketones, or enolates.
- Catalyst: Specification of any catalysts employed in the reaction. This can include Lewis acids, Brønsted acids, or bases.
- Solvent: The solvent system used for the reaction, influencing solubility and reaction kinetics.
- Reaction Conditions: Parameters such as temperature, pressure, and reaction time, critical for achieving the desired outcome.
- Work-up and Purification: Methods for isolating and purifying the target 1,5-diketone.
The patent's abstract and detailed description indicate that the method aims to control regioselectivity and stereoselectivity, leading to a purer product. For example, the patent describes a process using specific catalysts and reaction temperatures that prevent unwanted side reactions and isomer formation.
Claim 2-N: Dependent Claims and Variations
Dependent claims refine and narrow the scope of the independent claims, providing further protection for specific embodiments of the invention. These may include:
- Specific Substituents: Claims detailing the synthesis of 1,5-diketones with particular R groups (substituents) at defined positions on the diketone backbone. These R groups can be alkyl, aryl, heteroaryl, or functionalized groups, each potentially imparting different properties to the final molecule.
- Optimized Conditions: Claims specifying preferred ranges for reaction temperatures, catalyst concentrations, or reaction times that yield even better results.
- Specific Catalyst or Reagent: Claims that narrow the scope to the use of a particular, named catalyst or reagent that was found to be particularly effective.
- Stereoisomers: Claims that specifically cover the synthesis of particular stereoisomers (enantiomers or diastereomers) of the 1,5-diketones, which is crucial in pharmaceutical development.
Claim X: Application of the Compounds
A significant portion of the claims, if present, would relate to the application of the synthesized substituted 1,5-diketones. This typically involves:
- Use as Intermediates: Claims stating that the claimed compounds are useful as intermediates in the synthesis of active pharmaceutical ingredients (APIs).
- Therapeutic Applications: Claims for the use of these intermediates in the preparation of drugs for treating specific diseases. While the patent might not claim the final drug itself, it claims the method to create a key building block for such a drug.
What is the Scope of Protection Offered by CN105597206?
The scope of protection is determined by the breadth of the claims. CN105597206 provides protection for:
- The Specific Preparation Method: Any party using the exact process described in Claim 1 (or its specific variations in dependent claims) to synthesize these substituted 1,5-diketones would infringe upon the patent.
- The Synthesized Compounds: The patent protects the specific substituted 1,5-diketones themselves, as defined by the general formula (I) and its specific embodiments within the claims. This means that even if a third party discovers an alternative method to synthesize these same compounds, they may still be prevented from making, using, or selling them if the patent's claims cover the compounds themselves.
- Potential Applications: If the patent claims the use of these compounds as intermediates for specific therapeutic areas, it could impact the development of drugs in those areas by competitors.
The scope is further defined by the patent's drawings and detailed description, which provide examples and illustrate the invention. However, legal protection is strictly limited to the wording of the claims.
What is the Patent Landscape for Substituted 1,5-Diketones and Related Technologies?
The patent landscape surrounding substituted 1,5-diketones is complex, driven by their utility as versatile synthetic intermediates. Analysis of this landscape involves examining patents related to:
1. Synthesis Methods for 1,5-Diketones
This category includes patents for various chemical reactions that produce 1,5-diketones. Key reactions historically and currently relevant include:
- Michael Addition Reactions: A common pathway involving the conjugate addition of a nucleophile to an $\alpha,\beta$-unsaturated carbonyl compound, followed by subsequent reactions. Patents in this area might focus on novel catalysts, specific substrate combinations, or optimized conditions for higher yields and selectivities.
- Robinson Annulation: A sequence of Michael addition and aldol condensation reactions, often used to form cyclic ketones, but can be adapted for acyclic 1,5-diketones.
- Transition Metal-Catalyzed Reactions: Modern synthetic chemistry heavily relies on transition metals (e.g., palladium, copper, rhodium) for C-C bond formation. Patents may cover novel organometallic catalysts or catalytic cycles for 1,5-diketone synthesis.
- Enzyme-Catalyzed Synthesis: Biocatalysis offers environmentally friendly and highly selective routes. Patents may exist for engineered enzymes or bioprocesses for producing diketones.
- Flow Chemistry and Microreactors: Patents in this domain focus on continuous manufacturing processes for diketone synthesis, offering advantages in scalability, safety, and reaction control.
2. Applications of 1,5-Diketones in Pharmaceutical Synthesis
1,5-Diketones are valuable precursors for a wide range of heterocyclic compounds that form the core structures of many pharmaceuticals. Notable examples include:
- Pyrroles: Condensation of 1,5-diketones with primary amines or ammonia yields pyrroles, a fundamental building block in many drugs (e.g., statins like atorvastatin).
- Pyridines: Reactions with ammonia or ammonium salts can lead to pyridine derivatives, another prevalent scaffold in medicinal chemistry.
- Furans and Thiophenes: Synthesis of these five-membered heterocycles can also involve 1,5-diketone precursors under specific conditions.
- Other Heterocycles: Depending on the substituents on the 1,5-diketone and the reaction partner, a variety of other fused or unfused heterocyclic systems can be accessed, each with potential therapeutic relevance (e.g., in antivirals, anti-inflammatories, or oncology drugs).
3. Specific Drug Intermediates
Patents are often filed for methods to synthesize specific intermediates that are crucial for the production of a particular marketed drug or a drug candidate in development. CN105597206 likely falls into this category if the claimed substituted 1,5-diketones are known or predicted to be key precursors for a valuable API. This necessitates tracking patents that:
- Disclose synthesis of the exact 1,5-diketone structure claimed in CN105597206.
- Disclose the use of these 1,5-diketones to produce a specific therapeutic agent.
4. Geographic Distribution of Patents
A review of the patent landscape would also consider the geographic filing strategies of major pharmaceutical companies and research institutions. Patents in China (like CN105597206), the United States, Europe (via EPO), Japan, and South Korea are particularly relevant for the global pharmaceutical market. Identifying where similar inventions are patented can reveal key competitive regions and potential markets for licensing or enforcement.
Analysis of CN105597206 in the Context of the Landscape
CN105597206 focuses on a specific preparation method for a class of substituted 1,5-diketones. Its value within the broader patent landscape hinges on:
- Novelty and Inventive Step: Whether the claimed preparation method is indeed new and non-obvious compared to existing published synthetic routes for similar 1,5-diketones. A thorough prior art search would be required to assess this.
- Efficiency and Yield: The patent's claims and detailed description likely highlight improvements in reaction yield, purity, cost-effectiveness, or environmental impact of the synthesis. These factors are critical for industrial adoption.
- Commercial Relevance of the Target Diketones: The significance of CN105597206 is amplified if the substituted 1,5-diketones it produces are identified as key intermediates for high-value pharmaceuticals or drugs in development for significant unmet medical needs. For instance, if these diketones are precursors to a blockbuster drug, the patent on their synthesis becomes highly strategic.
- Freedom to Operate (FTO): Companies developing or manufacturing drugs that utilize 1,5-diketone intermediates must conduct FTO analyses to ensure their processes do not infringe on existing patents like CN105597206. This involves identifying relevant patents, analyzing their claims, and assessing the likelihood of infringement.
Potential Infringement Scenarios
- A generic drug manufacturer seeking to produce a drug that uses the claimed 1,5-diketone as an intermediate would need to ensure their synthesis route does not employ the patented method described in CN105597206, or that they have a license.
- A contract manufacturing organization (CMO) producing the intermediate on behalf of a pharmaceutical company must ensure the client's process is non-infringing.
- A research institution synthesizing the diketone for non-commercial research purposes might fall under experimental use exemptions, depending on local patent law, but commercialization would trigger infringement concerns.
Patent Expiration
China patent CN105597206 has a term of 20 years from the filing date. Filed on January 15, 2015, its expiration date is January 15, 2035. After this date, the preparation method and the specific compounds, as claimed, would enter the public domain, allowing for wider use without licensing.
Key Takeaways
- China patent CN105597206 protects a specific preparation method for substituted 1,5-diketones and potentially their applications as pharmaceutical intermediates.
- The patent's core claims define the reactants, catalysts, solvents, and reaction conditions for an improved synthesis process.
- The scope of protection extends to the method itself and the synthesized compounds, impacting their commercial use by third parties.
- The patent landscape for 1,5-diketones is driven by their utility in synthesizing diverse heterocyclic scaffolds essential for drug discovery.
- The strategic importance of CN105597206 is linked to the commercial value of the intermediates it produces and the drugs derived from them.
- Patent expiration is scheduled for January 15, 2035, after which the protected subject matter becomes public domain.
Frequently Asked Questions
1. What specific chemical structures are covered by the general formula (I) in CN105597206?
The specific structures are detailed within the patent's claims and specification, defining various substituents at defined positions on the 1,5-diketone backbone. A precise interpretation requires consulting the original patent document.
2. Does CN105597206 claim any finished pharmaceutical products?
The patent primarily focuses on the method of preparing substituted 1,5-diketones and their use as intermediates. It typically does not claim the final drug product itself, but rather the key chemical building block.
3. How can a company determine if its synthesis process infringes CN105597206?
Infringement analysis involves comparing the company's actual manufacturing process against the claims of CN105597206, often requiring expert legal and technical review to interpret claim language and assess process similarities.
4. Are there any known drugs that utilize intermediates synthesized by the method in CN105597206?
Identifying specific drugs requires cross-referencing the patented diketone structures and their synthetic pathways with known pharmaceutical APIs and their manufacturing processes, which is a complex undertaking.
5. What are the implications if CN105597206 is licensed to a competitor?
Licensing would grant the licensee the legal right to practice the patented invention, potentially excluding others or providing a competitive advantage, depending on the exclusivity terms of the license.
Citations
[1] ZHU, P. (2015). Preparation method of a substituted 1,5-diketone and its application (Chinese Patent CN105597206). State Intellectual Property Office of the People's Republic of China.
