Claims
- 1. A compound of the formula ##STR33## where (a) X is O or S;
- (b) Y is O or S;
- (c) m is 1 or 2;
- (d) each Z is independently H, loweralkyl, halogen, nitro, --NH.sub.2, loweralkylcarbonylamino, arylcarbonylamino, loweralkoxycarbonylamino, loweralkylamino, triloweralkylsilyl, formyl, loweralkylaminocarbonyl, carboxyl or loweralkoxycarbonyl;
- (e) R.sub.1 is H, loweralkyl, arylloweralkyl, heteroarylloweralkyl, cycloalkylmethyl or loweralkenylmethyl, and
- (f) R.sub.6 is hydrogen or methyl; the term aryl in each occurrence signifying an unsubstituted phenyl group or naphthyl group or a phenyl group substituted with 1, 2 or 3 substituent groups each of which being independently loweralkyl, halogen, nitro, loweralkoxy, hydroxy or trifluoromethyl; and the term heteroaryl signifying a group having the formula ##STR34## where W is O, S, NR.sub.5 or CH.dbd.N, R.sub.5 being hydrogen or loweralkyl; or a pharmaceutically acceptable acid addition salt thereof.
- 2. The compound as defined in claim 1, where the group R.sub.6 is present at the 1-position of the tetrahydroisoquinoline ring.
- 3. The compound as defined in claim 1, where m is 1.
- 4. The compound as defined in claim 1, where X is O.
- 5. The compound as defined in claim 1, where m is 1 and X is O.
- 6. The compound as defined in claim 1, where Y is O.
- 7. The compound as defined in claim 1, where Z is H.
- 8. The compound as defined in claim 1, where Z is halogen.
- 9. The compound as defined in claim 1, where Z is 7-chloro or 7-bromo.
- 10. The compound as defined in claim 1, where Z is nitro, amino, loweralkylcarbonylamino, arylcarbonylamino, loweralkoxycarbonylamino or loweralkylamino.
- 11. The compound as defined in claim 1, where Y is S.
- 12. The compound as defined in claim 1, where Y is S and X is O.
- 13. The compound as defined in claim 1, where Y is O and X is S.
- 14. The compound as defined in claim 1, which is (3aS-cis)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol, (1,2,3,4-tetrahydroisoquinolinyl) carbamate ester or the 3aR-cis isomer thereof or the racemic mixture or other mixture of the two.
- 15. The compound as defined in claim 1, which is (3aS-cis)-1,2,3,3a,8,8a-hexahydro-1,3,8-trimethylpyrrolo[2,3-b]indol-5-ol, (1-methyl-1,2,3,4-tetrahydroisoquinolinyl) carbamate ester or the 3aR-cis isomer thereof or the racemic mixture or other mixture of the two.
- 16. A pharmaceutical composition comprising an effective memory enhancing amount or pain alleviating amount of a compound as defined in claim 1 and a suitable carrier thereof.
- 17. A method of treating a patient in need of memory enhancement which comprises administering to the patient an effective amount of a compound as defined in claim 1.
- 18. A method of treating a patient in need of relief from pain which comprises administering to the patient an effective amount of a compound as defined in claim 1.
Parent Case Info
This is a continuation-in-part application of a prior patent application Ser. No. 049,894, filed May 15, 1987 now U.S. Pat. No. 4,791,107, which is a continuation-in-part of a prior application Ser. No. 885,991, filed Jul. 16, 1986 now abandoned.
US Referenced Citations (5)
Foreign Referenced Citations (1)
Number |
Date |
Country |
0154864 |
Sep 1985 |
EPX |
Non-Patent Literature Citations (4)
Entry |
P. Julian et al. J. Am. Chem. Soc., 57 563 (1935). |
Yu and Brossi, Heterocycles, vol. 27, No. 3, pp. 745-750 (1988). |
Chem. Abstracts, vol. 108 221937m (1988). |
Cowin, "Silicon in Oganic Synthesis," Chapter 10, pp. 125-133 Butterworths, (1981). |
Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
49894 |
May 1987 |
|
Parent |
885991 |
Jul 1996 |
|