# US 8,785,386 B2 · Benzazepine derivatives useful as vasopressin antagonists

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- Number: US 8,785,386 B2
- Document ID: US8785386B2
- Status: Granted
- Kind: B2
- Application number: 14/034,943
- Filed: 2013-09-24
- Published: 2014-01-23
- Granted: 2014-07-22
- Earliest claimed: 2007-06-26
- Assignees: Otsuka Pharmaceutical Co., Ltd.
- Applicants: Otsuka Phamaceutical Co., Ltd.
- Inventors: Kazumi Kondo; Yasuhiro Menjo; Takahiro Tomoyasu; Shin Miyamura; Yuso Tomohira; Takakuni Matsuda; Keigo Yamada; Yusuke Kato
- Web page: https://patentgrep.com/patent/US8785386B2

## CPC

- C07D 223/16: Benzazepines; Hydrogenated benzazepines
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A61P 7/10: Antioedematous agents; Diuretics
- A61P 7/12: Antidiuretics, e.g. drugs for diabetes insipidus (ADH A61P5/10)
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/02: Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- A61P 9/08: Vasodilators for multiple indications
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/12: Antihypertensives
- A61P 9/14: Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
- A61P 13/02: of urine or of the urinary tract, e.g. urine acidifiers
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07F 9/5535: {condensed with carbocyclic rings or ring systems}
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The present invention provides a benzazepine compound that can maintain for a long period of time the blood level of tolvaptan enabling to provide the desired pharmaceutical effects. The benzazepine compound of the present invention is represented by general formula (1) wherein R1 represents a —CO—(CH2)n—COR2 group (wherein n is an integer of 1 to 4, and R2 is (2-1) a hydroxy group; (2-2) a lower alkoxy group optionally substituted with a hydroxy group, a lower alkanoyl group, a lower alkanoyloxy group, a lower alkoxycarbonyloxy group, a cycloalkyloxycarbonyloxy group, or 5-methyl-2-oxo-1,3-dioxol-4-yl; or (2-3) an amino group optionally substituted with a hydroxy-lower alkyl group), or the like.

## Claims

### Claim 1

A benzazepine compound represented by general formula (1)
wherein R1 is a group of (1-1):
(1-1) a —CO—(CH2)n—COR2 group wherein n is an integer of 1 to 4, R2 is (2-1) a hydroxy group; (2-2) a lower alkoxy group optionally substituted with a hydroxy group, a lower alkanoyl group, a lower alkanoyloxy group, a lower alkoxycarbonyloxy group, a cycloalkyloxycarbonyloxy group, or 5-methyl-2-oxo-1,3-dioxol-4-yl; or (2-3) an amino group optionally substituted with a hydroxy-lower alkyl group;
or a salt thereof.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein, in formula (1), R1 is a —CO—(CH2)n—COOH group wherein n is an integer of 1 to 4; a salt thereof.

### Claim 3 (depends on 1)

A pharmaceutical preparation comprising the benzazepine compound of claim 1 or a pharmacologically acceptable salt thereof, and a pharmacologically acceptable diluent and/or carrier.

### Claim 4 (depends on 3)

The pharmaceutical preparation according to claim 3 for use as a vasodilator, hypotensive drug, aquaretic agent, or platelet aggregation inhibitor.