Substituted indeno, naphtho and cyclohepta pyrazoles

• US 3,932,430 A
• Filed: 04/11/1973
• Issued: 01/13/1976
• Est. Priority Date: 10/13/1971
• Status: Expired due to Term

• Current Assignee: Sandoz Inc. (Novartis Ag)
• Original Assignee: Sandoz Inc. (Novartis Ag)
• Inventors: Houlihan, William J., Habeck, Dietmar A.
• Primary Examiner(s): Rotman, Alan L.
• Application Number:
  US05/350,140
• Time in Patent Office: 1,007 Days
• Field of Search: 260/296 T, 260/296 P, 260/294.8 R, 260/295 S
• US Class Current: 546/275.7
• CPC Class Codes: C07C 45/455 with carboxylic acids or their derivatives
• CPC Class Codes: C07C 49/792 containing rings other than six-membered aromatic rings
• CPC Class Codes: C07D 207/333 Radicals substituted by oxygen or sulfur atoms
• CPC Class Codes: C07D 213/50 Ketonic radicals
• CPC Class Codes: C07D 213/53 Nitrogen atoms
• CPC Class Codes: C07D 231/54 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 303/32 by aldehydo- or ketonic radicals
• CPC Class Codes: C07D 307/46 Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
• CPC Class Codes: C07D 333/22 Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom

Abstract

Substituted indeno [1,2-c] pyrazoles, naphtho [1,2-c] pyrazoles and benzo [6,7] cyclohepta [1,2-c] pyrazoles e.g., 3-(2,3-dimethoxyphenyl)-4H-indeno[1,2-c] pyrazole and 4,5-dihydro-3-(4-pyridyl)-2H-naphtho[1,2-c] pyrazole, are useful as non-estrogenic anti-fertility agents and antihypertensive agents.

Claims

1. A compound of the formula ##SPC16##

where ring A represents the structures ##SPC17##

n is 2;

R₁ represents hydrogen or lower alkyl having 1 to 4 carbon atoms excluding tertiary butyl;

Ar is ##SPC18##

and

R₂ and R₃ each independently represent hydrogen, halo having an atomic weight of about 19 to 36, lower alkyl having 1 to 4 carbon atoms, lower alkoxy, trifluoromethyl or

R₂ and R₃ together independently represent methylenedioxy attached to adjacent carbon atoms,

provided that when R₂ and R₃ are independently trifluoromethyl or tertiary butyl they are not on adjacent carbon atoms, or a pharmaceutically acceptable acid addition salt thereof.

2. The compound of claim 1 having structure (1a) and (1b) when R₁ is hydrogen or structure (1b) when R₁ is lower alkyl.

3. The compound of claim 1, in which R₁ is hydrogen.

4. The compound of claim 3, in which n is 2.

5. The compounds of claim 1 in which R₁ is hydrogen and Ar is pyridyl.

6. The compounds of claim 5 in which n is 2.

7. The compound of claim 1 which is 4,5-dihydro-3-(4-pyridyl)-2H-naphtho[1,2-c]pyrazole.

8. The compound of claim 1 which is 4,5-dihydro-3-(2-pyridyl)-2H-naphtho[ 1,2-c]pyrazole.

9. The compound of claim 1 which is 4,5-dihydro-3-(3-pyridyl)-2H-naphtho[ 1,2-c]pyrazole.