Claims
- 1. A compound of the formula ##STR10## wherein R.sub.1 is hydrogen or alkyl of 1 to 10 carbons; R.sub.2 and R.sub.3 are hydrogen, or alkyl of 1 to 6 carbons and the substituted ethynyl group occupies either the 2 or the 3 position of the dihydronaphthalene nucleus;
- m is an integer having the value of 0-3;
- o is an integer having the value 0-3;
- Y is a phenyl group optionally substituted with one or two R.sub.2 groups;
- A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds;
- B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, CR.sub.7 OR.sub.13 O, or tri-lower alkylsilyl, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.12 is lower alkyl, and R.sub.13 is divalent alkyl radical of 2-5 carbons, and
- R.sub.22 is hydrogen, alkyl of 1 to 10 carbons, fluoro-substituted alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons and having 1 to 3 double bonds, alkynyl having 2 to 10 carbons and 1 to 3 triple bonds, hydroxy alkyl of 1 to 10 carbons, hydroxyalkynyl having 2 to 10 carbons and 1 to 3 triple bonds, acyloxyalkyl of 1 to 10 carbons or acyloxyalkynyl of 2 to 10 carbons and 1 to 3 triple bonds where the acyl group is represented by COR.sub.14, CN, CON(R.sub.1).sub.2, (CH.sub.2).sub.p CO.sub.2 R.sub.8 where p is an integer between 0 to 10, or R.sub.22 is aminoalkyl or thioalkyl of 1 to 10 carbons, or R.sub.22 is represented by (CH.sub.2).sub.p XR.sub.1 or by (CH.sub.2).sub.p NR.sub.1 R.sub.2 ; where X is O or S, the R.sub.14 group is hydrogen, alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons and having 1 to 3 double bond, alkynyl having 2 to 10 carbons and 1 to 3 triple bonds, carbocyclic aryl selected from the group consisting of phenyl, C.sub.1 -C.sub.10 -alkylphenyl, naphthyl, C.sub.1 -C.sub.10 -alkylnaphthyl, phenyl-C.sub.1 -C.sub.10 alkyl, or naphthyl-C.sub.1 -C.sub.10 alkyl.
- 2. A compound of claim 1 where the phenyl ring is 1,4 (para) substituted.
- 3. A compound of claim 1 where R.sub.2 is hydrogen.
- 4. A compound of claim 1 where R.sub.3 is hydrogen.
- 5. A compound of claim 1 where R.sub.22 is hydrogen, alkyl of 1-10 carbons, alkynyl of 2 to 10 carbons having 1 triple bond, CH.sub.2 CO.sub.2 R.sub.8, hydroxyalkyl having 1 to 10 carbons in the alkyl group or hydroxyalkynyl having 2 to 10 carbons in the alkynyl group.
- 6. A compound of claim 1 where R.sub.22 is cyano (CN) or CONH.sub.2.
- 7. A compound of the formula ##STR11## wherein R.sub.1 is hydrogen or alkyl of 1 to 10 carbons; R.sub.2 and R.sub.3 are hydrogen, or alkyl of 1 to 6 carbons and the substituted ethynyl group occupies either the 2 or the 3 position of the dihydronaphthalene nucleus;
- m is an integer having the value of 0-3;
- o is an integer having the value 0-3;
- Y is phenyl optionally substituted with one or two R.sub.2 groups;
- A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds;
- B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, CR.sub.7 OR.sub.13 O, or tri-lower alkylsilyl, where R.sub.7 is alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.12 is lower alkyl, and R.sub.13 is divalent alkyl radical of 2-5 carbons, and
- R.sub.22 is hydrogen, alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons and having 1 to 3 double bonds, alkynyl having 2 to 10 carbons and 1 to 3 triple bonds, hydroxy alkyl of 1 to 10 carbons, hydroxyalkynyl having 2 to 10 carbons and 1 to 3 triple bonds, acyloxyalkyl of 1 to 10 carbons or acyloxyalkynyl of 2 to 10 carbons and 1 to 3 triple bonds where the acyl group is represented by COR.sub.14, CN, CON(R.sub.1).sub.2, (CH.sub.2).sub.p CO.sub.2 R.sub.8 where p is an integer between 0 to 10, where the R.sub.14 group is hydrogen, alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons and having 1 to 3 double bond, alkynyl having 2 to 10 carbons and 1 to 3 triple bonds, carbocyclic aryl selected from the group consisting of phenyl, C.sub.1 -C.sub.10 -alkylphenyl, or phenyl-C.sub.1 -C.sub.10 alkyl.
- 8. A compound of claim 7 where A is (CH.sub.2).sub.n where n is 0-5 and where B is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, or CONR.sub.9 R.sub.10.
- 9. A compound of claim 8 where n is 0 and B is COOH or a pharmaceutically acceptable salt thereof.
- 10. A compound of the formula ##STR12## wherein R.sub.8 is hydrogen, an alkyl group of 1 to 10 carbons or trimethylsilylalkyl where the alkyl group has 1 to 10 carbons, and
- R.sub.22 is hydrogen, alkyl of 1 to 10 carbons, alkynyl having 2 to 10 carbons and 1 to 3 triple bonds, hydroxy alkyl of 1 to 10 carbons, hydroxyalkynyl having 2 to 10 carbons and 1 to 3 triple bonds, CN, CONH.sub.2, (CH.sub.2).sub.2 CO.sub.2 R.sub.8, and the substituted ethynyl group occupies the 2 or 3 position of the dihydronaphthalene nucleus.
- 11. A compound of claim 10 where R.sub.22 is H or lower alkyl of 1 to 10 carbons.
- 12. A compound of claim 11 where R.sub.8 is H or C.sub.2 H.sub.5.
- 13. A compound of claim 10 where R.sub.22 is CH.sub.2 COOR.sub.8, CN or CONH.sub.2.
- 14. A compound of claim 13 where R.sub.8 is H or C.sub.2 H.sub.5.
- 15. A compound of claim 10 where R.sub.22 is straight or branch-chained alkynyl having 2 to 10 carbons and 1 triple bond.
- 16. A compound of claim 15 where R.sub.8 is H or C.sub.2 H.sub.5.
- 17. A compound of claim 10 where R.sub.22 is 1-(3-hydroxy-3-methyl)butynyl.
- 18. A compound of claim 10 where R.sub.8 is H or C.sub.2 H.sub.5.
- 19. A compound of the formula ##STR13## wherein R.sub.1 is hydrogen or alkyl of 1 to 10 carbons; R.sub.2 and R.sub.3 are hydrogen, or alkyl of 1 to 6 carbons and the substituted ethynyl group occupies either the 2 or the 3 position of the dihydronaphthalene nucleus;
- m is an integer having the value of 0-3;
- o is an integer having the value 0-3;
- Y is a phenyl group optionally substituted with one or two R.sub.2 groups;
- A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds;
- B is hydrogen, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, CR.sub.7 OR.sub.13 O, or tri-lower alkylsilyl, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.12 is lower alkyl, and R.sub.13 is divalent alkyl radical of 2-5 carbons, and
- R.sub.22 is carbocyclic aryl selected from the group consisting of phenyl, C.sub.1 -C.sub.10 -alkylphenyl, naphthyl, C.sub.1 -C.sub.10 -alkylnaphthyl, phenyl-C.sub.1 -C.sub.10 alkyl, naphthyl-C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 -alkenylphenyl having 1 to 3 double bonds, C.sub.1 -C.sub.10 -alkynylphenyl having 1 to 3 triple bonds, phenyl-C.sub.1 -C.sub.10 alkenyl having 1 to 3 double bonds, phenyl-C.sub.1 -C.sub.10 alkynyl having 1 to 3 triple bonds, or a pharmaceutically acceptable salt of said compound.
Parent Case Info
This application is a divisional of application Ser. No. 08/854,297 filed on May 12, 1997, now U.S. Pat. No. 5,808,297, which is a divisional of application Ser. No. 08/366,193, filed on Dec. 29, 1994, now U.S. Pat. No. 5,648,514.
US Referenced Citations (103)
Foreign Referenced Citations (2)
Number |
Date |
Country |
170105A |
Jul 1983 |
EPX |
0098591 |
Jan 1984 |
EPX |
Divisions (2)
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Number |
Date |
Country |
Parent |
854297 |
May 1997 |
|
Parent |
366193 |
Dec 1994 |
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