# US 2014/0155416 A1 · Substituted pyrazolo[1,5-a] pyrimidines as calcium receptor modulating agents

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- Number: US 2014/0155416 A1
- Document ID: US20140155416A1
- Status: Published application
- Kind: A1
- Application number: 14/089,747
- Filed: 2013-11-25
- Published: 2014-06-05
- Earliest claimed: 2002-08-26
- Assignees: Takeda Pharmaceutical Company Limited
- Applicants: Takeda Pharmaceutical Company Limited
- Inventors: Tsuneo Yasuma; Akira Mori; Masahiro Kawase; Hiroyuki Kimura; Masato Yoshida; Albert Charles Gyorkos; Scott Alan Pratt; Christopher Peter Corrette
- Web page: https://patentgrep.com/patent/US20140155416A1

## CPC

- C07D 487/04: Ortho-condensed systems
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 3/14: for calcium homeostasis (vitamin D A61P3/02; parathyroid hormones A61P5/18; calcitonin A61P5/22; osteoporosis A61P19/10; bone metastasis A61P35/04)
- A61P 5/14: of the thyroid hormones, e.g. T3, T4
- A61P 9/12: Antihypertensives
- A61P 13/12: of the kidneys
- A61P 19/00: Drugs for skeletal disorders
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 19/08: for bone diseases, e.g. rachitism, Paget's disease
- A61P 19/10: for osteoporosis
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

There is provided a calcium receptor modulator comprising a compound of the formula (I): wherein ring A is an optionally substituted 5- to 7-membered ring; ring B is an optionally substituted 5- to 7-membered heterocyclic ring; X1 is CR1, CR1R2, N or NR13; X2 is N or NR3; Y is C, CR4 or N, Z is CR5, CR5R6, N or NR7; Ar is an optionally substituted cyclic group; R is H, an optionally substituted hydrocarbon group, etc.; and is a single bond or a double bond; R1, R2, R3, R4, R5, R6, R7 and R13 are independently H, an optionally substituted hydrocarbon group; or a salt thereof or a prodrug thereof. Compounds of the formula (II) and (III): wherein ring A is an optionally substituted 5- to 7-membered ring; Q is C, CR5 or N; R8, R9, R10, R11 and R12 are independently, H, an optionally substituted hydrocarbon group, etc., or a salt thereof are also provided. Also specify X1, R3, R1, Y and X3 in formula (II) and (III) as before.

## Claims

### Claim at position 1

-31. (canceled)

### Claim 32

A compound of the formula (III):
wherein R1 is a group of the formula: —CONR20(CR21R22R23) (wherein R20 is H, and one of R21, R22, and R23 is an optionally substituted C6-10 aryl group, and the others are the same or different and are each independently an optionally substituted C1-6 alkyl group);
R3 is H;
Y is CR4 (wherein R4 is H);
R8 is a C1-6 alkyl group;
Ar is an optionally substituted C6-10 aryl group;
R9 and R10 are the same or different and are each independently a C1-6 alkyl group;
X3 is CH2; and
is a single bond;
or a salt thereof.

### Claim 33 (depends on 32)

A pharmaceutical composition which comprises the compound according to claim 32 and a pharmaceutically acceptable carrier.

### Claim 34 (depends on 32)

A method for modulating a calcium receptor which comprises administering to a mammal an effective amount of a compound of the formula (I) or a salt thereof or a prodrug thereof according to claim 32.

### Claim 35 (depends on 32)

A method for preventing or treating bone diseases, which comprises administering to a mammal an effective amount of a compound of the formula (I) or a salt thereof or a prodrug thereof according to claim 32.

### Claim 36 (depends on 32)

The compound according to claim 32, wherein Ar is an optionally substituted phenyl group.

### Claim 37 (depends on 32)

The compound according to claim 32, wherein one of R21, R22, and R23 is phenyl substituted with a hydroxyl-C1-6 alkyl group or a C2-8 alkanoyl group.

### Claim 38 (depends on 32)

The compound according to claim 32, which is (5R)—N-{1-ethyl-1-[4-(1-hydroxyethyl)phenyl]propyl}-2,7,7-trimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide or (5R)—N-[1-(4-acetylphenyl)-1-ethylpropyl]-2,7,7-trimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide.