Prior art

The most relevant prior art for US Patent 8501730, based on its citations and background discussion, includes several US patents and non-patent literature. The patent US8501730 has a priority date of September 2, 2005. References published or effectively filed before this date are relevant for potential anticipation under 35 U.S.C. § 102.

Here is an analysis of the cited prior art:

Patent Citations

1. US 6,468,988 B1

   • Full Citation: US 6,468,988 B1, "Process for preparing benzazepine compounds," Otsuka Pharmaceutical Co., Ltd., published October 22, 2002.
   • Publication/Filing Date: Publication date: October 22, 2002.
   • Brief Description: Based on the title, this patent likely discloses methods for synthesizing benzazepine compounds. Given the common assignee (Otsuka Pharmaceutical Co., Ltd.) and the subject matter, it is expected to detail processes relevant to the core structures found in US8501730.
   • Potential Anticipation: This reference potentially anticipates aspects of the processes described in Claims 1-6 of US8501730, particularly if it outlines general synthetic routes for benzazepine compounds or specific steps for making intermediates such as compounds (2), (3), (4), or (11)-(14).

2. US 6,262,077 B1

   • Full Citation: US 6,262,077 B1, "Benzazepine derivatives and their use as vasopressin antagonists," Otsuka Pharmaceutical Co., Ltd., published July 17, 2001.
   • Publication/Filing Date: Publication date: July 17, 2001.
   • Brief Description: The title suggests that this patent describes benzazepine derivatives that function as vasopressin antagonists. These compounds are highly likely to include the active pharmaceutical ingredient (compound 10 in US8501730) or closely related structures, and potentially its precursors like compound (1).
   • Potential Anticipation: This patent potentially anticipates the compound (10) itself and its utility as a vasopressin antagonist. If it also details a method for its preparation, it could anticipate Claim 6 (process for producing compound (10)). If it discloses the synthesis of compound (1), it could anticipate Claim 1.

3. US 2003/0060481 A1

   • Full Citation: US 2003/0060481 A1, "Novel production method for benzazepine compound," Otsuka Pharmaceutical Co., Ltd., published March 27, 2003.
   • Publication/Filing Date: Publication date: March 27, 2003.
   • Brief Description: The title indicates that this application describes a novel method for producing benzazepine compounds, implying relevance to the synthetic chemistry of these structures.
   • Potential Anticipation: It potentially anticipates method claims 1-6 if its disclosed "novel production method" includes the specific steps or conditions claimed in US8501730 for preparing compounds (1), (4), or (10), or their intermediates.

4. US 2004/0058930 A1

   • Full Citation: US 2004/0058930 A1, "Process for preparing benzazepine compounds or salts thereof," Otsuka Pharmaceutical Co., Ltd., published March 25, 2004.
   • Publication/Filing Date: Publication date: March 25, 2004.
   • Brief Description: This patent application, similar to others from the same assignee, focuses on a process for synthesizing benzazepine compounds or their salts.
   • Potential Anticipation: It potentially anticipates method claims 1-6 if the processes for preparing compounds (1), (4), or (10) or their intermediates, as claimed in US8501730, are disclosed in this document.

5. US 2005/0143397 A1

   • Full Citation: US 2005/0143397 A1, "Process for preparing benzazepine compounds or salts thereof," Otsuka Pharmaceutical Co., Ltd., published June 30, 2005.
   • Publication/Filing Date: Publication date: June 30, 2005.
   • Brief Description: This application describes a process for preparing benzazepine compounds or their salts, indicating its relevance to the synthesis of these compounds.
   • Potential Anticipation: It potentially anticipates method claims 1-6 if the specific reactions or conditions claimed in US8501730 are disclosed in this document.

6. US 2005/0203117 A1

   • Full Citation: US 2005/0203117 A1, "Process for preparing benzazepine compounds or salts thereof," Otsuka Pharmaceutical Co., Ltd., published September 15, 2005.
   • Publication/Filing Date: Publication date: September 15, 2005. This publication date is after the priority date of US8501730 (September 2, 2005). Therefore, it would only constitute prior art under 35 U.S.C. § 102 if its effective filing date (e.g., through a priority claim to an earlier application) precedes September 2, 2005. Without further information on its filing date or priority chain, its direct anticipatory effect based on publication date is limited.
   • Potential Anticipation: If its effective filing date is prior to September 2, 2005, this reference would likely disclose processes for preparing benzazepine compounds, potentially anticipating claims 1-6.

7. US 2006/0009633 A1

   • Full Citation: US 2006/0009633 A1, "Process for preparing benzazepine compounds or salts thereof," Otsuka Pharmaceutical Co., Ltd., published January 12, 2006.
   • Publication/Filing Date: Publication date: January 12, 2006. This publication date is after the priority date of US8501730 (September 2, 2005). Therefore, it would only constitute prior art under 35 U.S.C. § 102 if its effective filing date precedes September 2, 2005.
   • Potential Anticipation: If its effective filing date is prior to September 2, 2005, this reference would likely disclose processes for preparing benzazepine compounds, potentially anticipating claims 1-6.

8. US 2007/0197775 A1

   • Full Citation: US 2007/0197775 A1, "Production method for 7-chloro-2,3,4,5-tetrahydro-1H-1-benzazepine-5-one," Otsuka Pharmaceutical Co., Ltd., published August 23, 2007.
   • Publication/Filing Date: Publication date: August 23, 2007. This publication date is after the priority date of US8501730 (September 2, 2005). Therefore, it would only constitute prior art under 35 U.S.C. § 102 if its effective filing date precedes September 2, 2005.
   • Brief Description: The title specifies a production method for 7-chloro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one, which corresponds to compound (2) in US8501730.
   • Potential Anticipation: If its effective filing date is prior to September 2, 2005, this reference could anticipate the process for producing compound (2), which is a starting material for Claim 1 of US8501730.

Non-Patent Literature

1. Yasuhiro Torisawa et al., Bioorganic & Medicinal Chemistry Letters, 10 (2000), pp. 2493-2495.

   • Full Citation: Yasuhiro Torisawa et al., "A Novel and Efficient Synthesis of 7-Chloro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one," Bioorganic & Medicinal Chemistry Letters, 10 (2000), pp. 2493-2495.
   • Publication/Filing Date: Published in 2000. (Well before the September 2, 2005, prior art date of US8501730).
   • Brief Description: This article details a novel and efficient synthesis for 7-chloro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one. US8501730 explicitly cites this paper in its background art as a process for preparing benzoic acid compounds (4) via Reaction Scheme C.
   • Potential Anticipation: Since US8501730 states that "the benzoic acid compounds (4) are usually prepared by a process as shown in the following Reaction Scheme C (cf. Yasuhiro Torisawa et al., Bioorganic & Medicinal Chemistry Letters, 10(2000), pp. 2493-2495)", this paper potentially anticipates claims 2, 3, 4, or 5 of US8501730 if the disclosed process in the paper for preparing compound (4) (or its intermediates) directly matches the claimed processes. The synthesis of compound (2) (7-chloro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one) is also directly disclosed.

2. Kondo, Kazumi et al., Bioorganic & Medicinal Chemistry 7 (1999), pp. 1743-1754.

   • Full Citation: Kondo, Kazumi et al., "Synthetic Studies on Vasopressin V2 Receptor Antagonists: Asymmetric Synthesis of the Benzazepine Moiety," Bioorganic & Medicinal Chemistry, 7 (1999), pp. 1743-1754.
   • Publication/Filing Date: Published in 1999. (Well before the September 2, 2005, prior art date of US8501730).
   • Brief Description: This article presents synthetic studies on vasopressin V2 receptor antagonists, focusing on the asymmetric synthesis of the benzazepine moiety. US8501730 references this paper in its background art for the preparation of benzazepine compounds (1) using processes shown in Reaction Schemes A and B.
   • Potential Anticipation: US8501730 clearly indicates that "the benzazepine compounds (1) have been prepared by the processes as shown in the following Reaction schemes A and B (cf. JP-A-4-154765 and Kazumi Kondo et al., Bioorganic & Medicinal Chemistry 7(1999), pp. 1743-1754)." This directly implies that processes for preparing compound (1) and potentially compound (10) were known from this reference. Therefore, this paper could potentially anticipate Claim 1 (process for compound (1)) and Claim 6 (process for compound (10)) of US8501730. Prior litigation has already affirmed that "the asserted method claims of the patent were found invalid as obvious over a 1999 synthesis paper by Kondo," indicating its strong relevance to the method claims.

3. JP-A-4-154765

   • Full Citation: JP-A-4-154765 (Japanese Patent Application Publication).
   • Publication/Filing Date: Published in 1992 (Heisei 4). (Well before the September 2, 2005, prior art date of US8501730).
   • Brief Description: US8501730 states that compounds (1) and (4) are useful intermediates for preparing pharmaceutically active benzazepine compounds having vasopressin antagonistic activity (e.g., compound 10), citing JP-A-4-154765. It also indicates that known processes for preparing compound (1) are disclosed in this reference (Reaction Schemes A and B).
   • Potential Anticipation: This Japanese patent likely discloses the compounds (1), (4), and (10) themselves, and their use as vasopressin antagonists or intermediates. Crucially, it also describes processes for preparing compound (1) and compound (4). Therefore, this reference potentially anticipates Claims 1, 2, 3, 4, 5, and 6, as it appears to disclose the fundamental chemical transformations and the resulting compounds, albeit possibly without the "high yield and high purity on industrial scale" benefits claimed by US8501730.