Fused pyrazole compounds and pharmaceutical use thereof

• US 5,006,520 A
• Filed: 06/13/1989
• Issued: 04/09/1991
• Est. Priority Date: 10/13/1987
• Status: Expired due to Fees

• Current Assignee: Yoshitomi Pharmaceutical Industries, Ltd. (UBE Corporation)
• Original Assignee: Yoshitomi Pharmaceutical Industries, Ltd. (UBE Corporation)
• Inventors: Hisadome, Masao, Sueoka, Hiroyuki, Oe, Takanori, Yamagami, Keiji
• Primary Examiner(s): Bentz, Bernard I.
• Application Number:
  US07/373,296
• Time in Patent Office: 665 Days
• Field of Search: 546/119, 514/303, 514/212, 514/218, 514/228.5, 514/231.5, 514/253, 540/475, 540/597, 544/586, 544/61, 544/27, 544/362
• US Class Current: 514/217.07
• CPC Class Codes: C07D 231/56 Benzopyrazoles; Hydrogenated benzopyrazoles
• CPC Class Codes: C07D 471/04 Ortho-condensed systems

Abstract

Novel fused pyrazole compounds of the general formula ##STR1## wherein all the symbols are as defined in the specification or its pharmaceutically acceptable salt which possesses a stimulating action on phagocytosis of leukocytes, a stimulating action on phagocytosis of macrophages, a restorative action on leukopenia, a stimulating action on non-specific resistance to infection, an antitumour action, an activating action on immune responses and the like, and thereof is of use as a pharmaceutical.

Claims

1. A fused pyrazole compound of the formula ##STR20## on a pharmaceutically acceptable salt thereof wherein in the above formula, X is ═

N--;

R represents hydrogen, an alkyl group, an alkoxy group or a halogen;

Y¹ represents a group of the formula;

##STR21## phenyl group or a phenyl group substituted by one to three halogen(s), alkyl group(s) and/or alkoxy group(s), and Y² represents a group of the formula;

##STR22## a group of the formula;

--A² --B², hydrogen, an alkyl group, a phenylalkyl group, a phenylalkyl group in which the phenyl nucleus is substituted by one to three halogen(s), alkyl group(s) and/or alkoxy group(s), phenyl group or a phenyl group substituted by one to three halogen(s), alkyl group(s) and/or alkoxy group(s), an alkoxyalkyl group, wherein either Y¹ or Y² represents or both of Y¹ and Y² represent a group of the formula;

##STR23## or of the formula;

##STR24## wherein, Z¹ and Z² are the same or different, and respectively represent --O--, --S-- or --NR³ (wherein R³ represents hydrogen or an alkyl group);

A¹ and A² are the same or different, and respectively represent an alkylene group;

B¹ and B² are the same or different, and respectively represent carboxyl group, an alkoxycarbonyl group, a phenylalkoxycarbonyl group (in which the phenyl nucleous may be substituted by one to three halogen(s), alkyl group(s), and/or alkoxy group(s)), an acyl group, hydroxy group, an acyloxy group or a group of the formula;

##STR25## (wherein R¹ and R² are the same or different and respectively represent hydrogen, an alkyl group, a dialkylaminoalkyl group or a hydroxyalkyl group or represent a group which combinedly forms, together with the adjacent nitrogen atom, a heterocycle) and L¹ and L² are the same or different and respectively represent hydrogen, a halogen, an alkyl group or an alkoxy group.

2. The compound as claimed in claim 1 wherein at least one of Z¹ and Z² is oxygen.

3. A compound as claimed in claim 1 which is selected from a group consisting of 3-[4-(1-methyl-2-dimethylaminoethoxy)phenyl]-1H-pyrazolo[3,4-b]pyridin-1-ylacetic acid, ethyl 3-[4-(1-methyl-2-dimethylaminoethoxy)phenyl]-1H-pyrazolo[3,4-b]pyridin-1-ylacetate, 3-[4-(3-dimethylaminopropoxy)phenyl]-1H-pyrazolo[3,4-b]pyridin-1-ylacetic acid, ethyl 3-[4-(2-dimethylaminoethoxy)phenyl]-1H-pyrazolo[3,4-b]pyridin1-ylacetate, 1-[4-(3-dimethylaminopropoxy)phenyl]-3-phenyl-1H-pyrazolo[3,4-b]pyridine, 1-[3-(2-methyl-3-dimethylaminopropoxy)phenyl]-3-phenyl-1H-pyrazolo[3,4-b]pyridine, 1-(4-methylphenyl)-3-[4-(3-dimethylaminopropoxy)phenyl]-1H-pyrazolo[3,4-b]pyridine, 1-[3-(2-dimethylaminoethoxy)phenyl]-3-[4-(2-dimethylaminoethoxy)phenyl]-1H-pyrazolo[3,4-b]pyridine, N-(2-diethylaminoethyl)-3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]phenoxyacetamide and 3-{3-[4-(3-dimethylaminopropoxy)phenyl]-1H-pyrazolo[3,4-b]pyridin-1-yl}propionic acid and their pharmaceutically acceptable salts.

4. A pharmaceutical composition which comprises as the effective ingredient the compound as claimed in claim 1 and a pharmacologically acceptable carrier.