# US 8,785,631 B2 · Oxazolone derivative compounds having a 3-oxa-1-azaspiro[4.5] core

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 8,785,631 B2
- Document ID: US8785631B2
- Status: Granted
- Kind: B2
- Application number: 12/087,689
- Filed: 2007-01-10
- Published: 2009-05-21
- Granted: 2014-07-22
- Earliest claimed: 2006-01-11
- Assignees: Seikagaku Corporation
- Applicants: Tsuneo Koji; Hisatomo Kunii; Nobuo Kobayashi
- Inventors: Tsuneo Koji; Hisatomo Kunii; Nobuo Kobayashi
- Web page: https://patentgrep.com/patent/US8785631B2

## CPC

- C07D 263/52: condensed with carbocyclic rings or ring systems
- A61P 19/10: for osteoporosis
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 413/14: containing three or more hetero rings
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/10: linked by a carbon chain containing aromatic rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Novel raw material compounds are provided that are useful for producing novel cycloalkane carboxamide derivatives having cathepsin K inhibitory action. An oxazolone derivative represented by formula (I): [wherein, R1 represents a substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted phenyl group, substituted or unsubstituted naphthyl group or substituted or unsubstituted heterocyclic group, and ring A represents a saturated cyclic alkylidene group having 6 to 7 carbon atoms].

## Claims

### Claim 1

An oxazolone derivative of formula (I):
wherein R1 represents an alkyl group of 1 or 2 carbon atoms substituted by a phenyl group, furanyl group, furanylcarbonylamino group or benzoylamino group; a cycloalkyl group of 5 or 6 carbon atoms; a cyclopentenyl group; an alkenyl group of 2 carbon atoms which is substituted by a furanyl group; a phenyl group which is substituted by a phenyl group, methoxy group, propylpiperazinyl group, dimethylaminomethyl group, morpholinylmethyl group or thiazolyl group which may be substituted by a methylpiperazinyl group or morpholinylpiperidinyl group; a naphthyl group; a furanyl group which may be substituted by a methyl group; a thienyl group which may be substituted by a methyl group or ethoxy group; a pyrrolyl group which may be substituted by a methyl group; a pyridinyl group which may be substituted by a hydroxyl group; a piperidinyl group which may be substituted by an ethoxycarbonyl group, propoxycarbonyl group or furanylcarbonyl group; a pyrazinyl group; an isoxazolyl group which may be substituted by a methyl group; a benzothiazolyl group; a benzodioxolyl group; a tetrahydrobenzofuranyl group; an indolyl group; or a benzothienyl group; and
ring A represents an unsubstituted cyclohexylidene group.

### Claim 2

An oxazolone derivative compound selected from the group consisting of:
2-(phenylmethyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(2-phenylethyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(4-biphenyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(2-naphthyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(1-naphthyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[(RS)-2,3-tetrahydrobenzofuran-2-yl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(2-furanyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(3-furanyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[2-(2-furanyl)ethenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-cyclohexyl-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(6-benzothiazolyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(2-thienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(1,3-benzodioxol-5-yl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(2-pyridinyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(3-thienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(3-ethoxy-2-thienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[2-[(S)-1-phenylethyl]]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(2-pyrazinyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(5-methylisoxazol-4-yl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-cyclopentyl-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(5-methyl-2-thienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(4-methoxyphenyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(3-methyl-2-thienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(3-methyl-2-furanyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(3-pyridinyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(1-methyl-1H-pyrrol-2-yl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[(R)-1-phenylethyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(1H-indol-5-yl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(1-cyclopentenyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(4-pyridinyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(1H-pyrrol-2-yl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(6-hydroxy-2-pyridinyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(2-hydroxy-3-pyridinyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(6-hydroxy-3-pyridinyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[2-(2-furanyl)ethyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[1-[(2-propoxy)carbonyl]piperidin-4-yl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[1-(ethoxycarbonyl)piperidin-4-yl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[1-(2-furanylcarbonyl)piperidin-4-yl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[[(2-furanylcarbonyl)amino]methyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[(benzoylamino)methyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[[4-(1-propyl)piperazin-1-yl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-(2-benzothienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[4-[(dimethylamino)methyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[4-(4-morpholinylmethyl)phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one,
2-[4-[2-(4-methyl-1-piperazinyl)-4-thiazolyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one and
2-[4-[2-[4-(4-morpholinyl)-1-piperidinyl]-4-thiazolyl]phenyl]-3-oxa-1-azaspiro[4.5]dec-1-en-4-one.