Substituted 1,3,4,9-tetrahydropyrano[3,4,-b]indole-1-acetic acids, pharmaceutical compositions containing them, and methods for treating inflammatory conditions and for analgesic purposes using them

• US 4,810,699 A
• Filed: 09/21/1987
• Issued: 03/07/1989
• Est. Priority Date: 02/20/1987
• Status: Expired due to Fees

• Current Assignee: American Home Products Corporation (Pfizer Inc.)
• Original Assignee: American Home Products Corporation (Pfizer Inc.)
• Inventors: Demerson, Christopher A., Sabatucci, Joseph P., Failli, Amadeo A.
• Primary Examiner(s): Rizzo, Nicholas S.
• Assistant Examiner(s): Rivers, Diana G.
• Application Number:
  US07/099,025
• Time in Patent Office: 533 Days
• Field of Search: 548/432, 514/411, 514/282, 514/161
• US Class Current: 514/161
• CPC Class Codes: C07D 491/04 Ortho-condensed systems

Abstract

Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid nucleus bearing a substituent in position 1,5, 6, 7 and 8. The derivatives are useful anti-inflammatory and analgesic agents and methods for their preparation and use are also disclosed.

Claims

1. The compounds having the structure ##STR5## wherein R¹ is hydrogen, lower alkyl containing 1 to 4 carbon atoms or halogen, R² is --O--CH₂ --CH═

CH₂, --O--CH₂ --CF₃, --O--CH(CH₃)--CF₃, --O--CH₂ --C.tbd.CH and the pharmaceutically acceptable salts thereof.

2. The compounds according to claim 1 wherein R¹ is hydrogen or chlorine, R² is --O--CH₂ --CF₃ and the pharmaceutically acceptable salts thereof.

3. The compound according to claim 2 designated 7-chloro-1-ethyl-1,3,4,9-tetrahydro-8-(2,2,2-trifluoroethoxy)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.

4. A compound according to claim 2 designated 1-ethyl-1,3,4,9-tetrahydro-8-(2,2,2-trifluoroethoxy)-pyrano[3,4-b]indole-1-acetic and the pharmaceutically acceptable salts thereof.

5. A pharmaceutical composition comprising a compound of structure (I), or a pharmaceutically acceptable salt thereof, as define in claim 1 and a pharmaceutically acceptable carrier.

6. A pharmaceutical composition comprising a compound of structure (I), or a pharmaceutically acceptable salt thereof, as defined in claim 1, a nonsteroid anti-inflammatory drug selected from the group consisting of, ibuprofen and aspirin, an opiate analgesic selected from the group consisting of codeine, oxycodone and morphine and a pharmaceutically acceptable carrier.

7. A method for treating inflammatory conditions and for analgesic purposes in conditions which require relief from pain in a mammal which comprises the administration to said mammal of an effective amount of a compound selected from those of formula (I), or a pharmaceutically acceptable salt thereof, as claimed in claim 1.

8. A method for treating inflammatory conditions and for analgesic purposes in conditions which require relief from pain in a mammal which comprises the administration to said mammal of an effective amount of a compound selected from those of formula (I), or a pharmaceutically acceptable salt thereof, as claimed in claim 1, in conjunction with nonsteroid anti-inflammatory drugs and opiate analgesics.