Claims
- 1. ##STR17## wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons; R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
- m is an integer having the value of 0-3;
- o is an integer having the value of 0-3;
- Z is --C--.tbd.C--
- --N.dbd.N--,
- --N.dbd.CR.sub.1 --,
- --CR.sub.1 .dbd.N--,
- --(CR.sub.1 .dbd.CR.sub.1).sub.n,--where n' is an integer having the value 0-5,
- --CO--NR.sub.1 --,
- --CS--NR.sub.1 --,
- --NR.sub.1 --CO,
- --NR.sub.1 --CS,
- --COO--,
- --OCO--;
- --CSO--;
- --OCS--;
- Y is heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said heteroaryl groups being optionally substituted with one or two R.sub.2 group;
- A is (CH.sub.2).sub.q where q 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 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.14 is (R.sub.15).sub.r -phenyl, (R.sub.15).sub.r -naphthyl, or (R.sub.15).sub.r - heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and
- R.sub.15 is independently H, F, Cl, Br, I, NO.sub.2, N(R.sub.8).sub.2, NH(R.sub.8), COR.sub.8, NR.sub.8 CON(R.sub.8).sub.2, OH, OCOR.sub.8, OR.sub.8, CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons.
- 2. A compound of claim 1 where Y is pyridyl, thienyl or furyl.
- 3. A compound of claim 1 where Y is pyridyl.
- 4. A compound of claim 1 where R.sub.2 is H, F, or CF.sub.3.
- 5. A compound of claim 1 where R.sub.3 is H or methyl.
- 6. A compound of claim 1 where R.sub.14 is (R.sub.15).sub.r - phenyl.
- 7. A compound of claim 1 where R.sub.14 is (R.sub.15).sub.r - heteroaryl.
- 8. A compound of claim 7 where R.sub.14 is (R.sub.15).sub.r - heteroaryl where the heteroaryl group is a 5 or six membered ring having 1 or 2 heteroatoms.
- 9. A compound of claim 8 where the heteroaryl group is selected from 2-pyridyl, 3-pyridyl, 2-thienyl and 2-thiazolyl.
- 10. A compound of claim 1 where the R.sub.15 group is H, CF.sub.3, F, lower alkyl, lower alkoxy, hydroxy or chlorine.
- 11. A compound of claim 1 where Z is --C.tbd.C--.
- 12. A compound of claim 1 where Z is --CS.sub.1 --NR--.
- 13. A compound of claim 1 where X is S.
- 14. A compound of the formula ##STR18## wherein X is S, O NR' where R' is H or alkyl of 1 to 6 carbons; R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
- m is an integer having the value of 0-3;
- o is an integer having the value of 0-3;
- Z is --C.tbd.C--
- --N.dbd.N--,
- --N.dbd.CR.sub.1 --,
- --CR.sub.1 .dbd.N--,
- --(CR.sub.1 .dbd.CR.sub.1).sub.n' --where n' is an integer having the value 0-5,
- --CO--NR.sub.1 --,
- --CS--NR.sub.1 --,
- --NR.sub.1 --CO,
- --NR.sub.1 --CS,
- --COO--,
- --OCO--;
- --CSO--;
- --OCS--;
- Y is heteroaryl selected from a group consisting of thienyl and furyl, said thienyl and furyl groups being optionally substituted with one or two R.sub.2 group;
- A is (CH.sub.2).sub.q where q 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.14 is (R.sub.15).sub.r - phenyl, (R.sub.15).sub.r - naphthyl, or (R.sub.15).sub.r - heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and
- R.sub.15 is independently H, F, Cl, Br, I, NO.sub.2, N(R.sub.8).sub.2, NH(R.sub.8), COR.sub.8, NR.sub.8 CON(R.sub.8).sub.2, OH, OCOR.sub.8, OR.sub.8, CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons.
- 15. A compound of the formula ##STR19## wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons; R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
- m is an integer having the value of 0-3;
- o is an integer having the value of 0-3;
- Y is heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said heteroaryl groups being optionally substituted with one or two R.sub.2 group;
- A is (CH.sub.2).sub.q where q 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.14 is (R.sub.15).sub.r - phenyl, (R.sub.15).sub.r - -naphthyl, or (R.sub.15).sub.r - heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and
- R.sub.15 is independently H, F, Cl, Br, I, NO.sub.2, N(R.sub.8).sub.2, NH(R.sub.8), COR.sub.8, NR.sub.8 CON(R.sub.8).sub.2, OH, OCOR.sub.8, OR.sub.8, CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons.
- 16. A compound of the formula ##STR20## wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons; R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
- m is an integer having the value of 0-3;
- o is an integer having the value of 0-3;
- Y is heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said heteroaryl groups being optionally substituted with one or two R.sub.2 group;
- A is (CH.sub.2).sub.q where q 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.14 is (R.sub.15).sub.r - phenyl, (R.sub.15).sub.r - naphthyl, or (R.sub.15).sub.r - heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and
- R.sub.15 is independently H, F, Cl, Br, I, NO.sub.2, N(R.sub.8).sub.2, NH(R.sub.8), COR.sub.8, NR.sub.8 CON(R.sub.8).sub.2, OH, OCOR.sub.8, OR.sub.8, CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons.
- 17. A compound of the formula ##STR21## wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons; R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
- m is an integer having the value of 0-3;
- o is an integer having the value of 0-3;
- Y is heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said heteroaryl groups being optionally substituted with one or two R.sub.2 group;
- A is (CH.sub.2).sub.q where q 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.14 is (R.sub.15).sub.r - phenyl, (R.sub.15).sub.r - naphthyl, or (R.sub.15).sub.r - heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and
- R.sub.15 is independently H, F, Cl, Br, I, NO.sub.2, N(R.sub.8).sub.2, NH(R8), COR.sub.8, NR.sub.8 CON(R.sub.8).sub.2, OH, OCOR.sub.8, OR.sub.8, CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons.
- 18. A compound of the formula ##STR22## wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons; R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
- m is an integer having the value of 0-3;
- o is an integer having the value of 0-3;
- Y is heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said heteroaryl groups being optionally substituted with one or two R.sub.2 group;
- A is (CH.sub.2).sub.q where q 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.14 is (R.sub.15).sub.r - phenyl, (R.sub.15).sub.r - naphthyl, or (R.sub.15).sub.r - heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and
- R.sub.15 is independently H, F, Cl, Br, I, NO.sub.2, N(R.sub.8).sub.2, NH(R.sub.8), COR.sub.8, NR.sub.8 CON(R.sub.8).sub.2, OH, OCOR.sub.8, OR.sub.8, CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons.
- 19. The method of treating a pathological condition in a mammal, said condition associated with a retinoic acid receptor activity, said method comprising administering to said mammal a retinoid antagonist or negative hormone capable of binding to a retinoic acid receptor subtype selected from the group consisting of RAR.sub..alpha., RAR.sub..beta. and RAR.sub..gamma., said antagonist or negative hormone being administered in an amount pharmaceutically effective to provide a therapeutic benefit against said pathological condition in said mammal and wherein the negative hormone or antagonist has the formula: ##STR23## wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons; R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
- m is an integer having the value of 0-3;
- o is an integer having the value of 0-3;
- Z is --C.tbd.C--
- --N.dbd.N--,
- --N.dbd.CR.sub.1 --,
- --CR.sub.1 .dbd.N--,
- --(CR.sub.1 .dbd.CR.sub.1).sub.n --where n' is an integer having the value 0-5,
- --CO--NR.sub.1 --,
- --CS--NR.sub.1 --,
- --NR.sub.1 --CO,
- --NR.sub.1 --CS,
- --COO--,
- --OCO--;
- --CSO--;
- --OCS--;
- Y is heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said heteroaryl groups being optionally substituted with one or two R.sub.2 group;
- A is (CH.sub.2).sub.q where q 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.14 is (R.sub.15).sub.r - phenyl, (R.sub.15).sub.r - naphthyl, or (R.sub.15).sub.r - heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and
- R.sub.15 is independently H, F, Cl, Br, I, NO.sub.2, N(R.sub.8).sub.2, NH(R.sub.8), COR.sub.8, NR.sub.8 CON(R.sub.8).sub.2, OH, OCOR.sub.8, OR.sub.8, CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons.
- 20. A method of claim 19 where in the formula of the antagonist or negative hormone Y is pyridyl, thienyl or furyl.
- 21. A method of claim 19 where in the formula of the antagonist or negative hormone Y is pyridyl.
- 22. A method of claim 19 where in the formula of the antagonist or negative hormone R.sub.2 is H, F, or CF.sub.3.
- 23. A method of claim 19 where in the formula of the antagonist or negative hormone R.sub.3 is H or methyl.
- 24. A method of claim 19 where in the formula of the antagonist or negative hormone R.sub.14 is (R.sub.15).sub.r - phenyl.
- 25. A method of claim 19 where in the formula of the antagonist or negative hormone R.sub.14 is (R.sub.15).sub.r - heteroaryl.
- 26. A method of claim 25 where in the formula of the antagonist or negative hormone R.sub.14 is (R.sub.15).sub.r - heteroaryl where the heteroaryl group is a 5 or six membered ring having 1 or 2 heteroatoms.
- 27. A method of claim 26 where in the formula of the antagonist the heteroaryl group is selected from 2-pyridyl, 3-pyridyl, 2-thienyl and 2-thiazolyl.
- 28. A method of claim 19 where in the formula of the antagonist or negative hormone the R.sub.15 group is H, CF.sub.3, F, lower alkyl, lower alkoxy, hydroxy or chlorine.
- 29. A method of claim 19 where in the formula of the antagonist or negative hormone Z is --C.tbd.C--.
- 30. A method of claim 19 where in the formula of the antagonist or negative hormone Z is --COO--.
- 31. A method of claim 19 where in the formula of the antagonist or negative hormone X is S.
- 32. A method of treating a pathological condition in a mammal, said condition associated with a retinoic acid receptor activity, said method comprising administering to said mammal a retinoid antagonist or negative hormone capable of binding to a retinoic acid receptor subtype selected from the group consisting of RAR.sub..alpha., RAR.sub..beta. and RAR.sub..gamma., said antagonist or negative hormone being administered in an amount pharmaceutically effective to provide a therapeutic benefit against said pathological condition in said mammal and wherein the negative hormone or antagonist has the formula ##STR24## wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons; R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
- m is an integer having the value of 0-3;
- o is an integer having the value of 0-3;
- Z is --C.dbd.C--
- --N.dbd.N--,
- --N.dbd.CR.sub.1 --,
- --CR.sub.1 .dbd.N--,
- --(CR.sub.1 .dbd.CR.sub.1).sub.n' --where n' is an integer having the value 0-5,
- --CO--NR.sub.1 --,
- --CS--NR.sub.1 --,
- --NR.sub.1 --CO,
- --NR.sub.1 --CS,
- --COO--,
- --OCO--;
- --CSO--;
- --OCS--;
- Y is heteroaryl selected from a group consisting of thienyl and furyl, said thienyl and furyl groups being optionally substituted with one or two R.sub.2 group;
- A is (CH.sub.2).sub.q where q 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, COOR8, 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.14 is (R.sub.15).sub.r --phenyl, (R.sub.15).sub.r -naphthyl, or (R.sub.15).sub.r - heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and
- R.sub.15 is independently H, F, Cl, Br, I, NO.sub.2, N(R.sub.8).sub.2, NH(R.sub.8), COR.sub.8, NR.sub.8 CON(R.sub.8).sub.2, OH, OCOR.sub.8, OR.sub.8, CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons.
- 33. A method of treating a pathological condition in a mammal, said condition associated with a retinoic acid receptor activity, said method comprising administering to said mammal a retinoid antagonist or negative hormone capable of binding to a retinoic acid receptor subtype selected from the group consisting of RAR.sub..alpha., RAR.sub..beta. and RAR.sub..gamma., said antagonist or negative hormone being administered in an amount pharmaceutically effective to provide a therapeutic benefit against said pathological condition in said mammal and wherein the negative hormone or antagonist has the formula ##STR25## wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons; R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
- m is an integer having the value of 0-3;
- o is an integer having the value of 0-3;
- Y is heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said heteroaryl groups being optionally substituted with one or two R.sub.2 group;
- A is (CH.sub.2).sub.q where q 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.14 is (R.sub.15).sub.r - phenyl, (R.sub.15).sub.r - naphthyl, or (R.sub.15).sub.r - heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and
- R.sub.15 is independently H, F, Cl, Br, I, NO.sub.2, N(R.sub.8).sub.2, NH(R.sub.8), COR.sub.8, NR.sub.8 CON(R.sub.8).sub.2, OH, OCOR.sub.8, OR.sub.8, CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons.
- 34. A method of treating a pathological condition in a mammal, said condition associated with a retinoic acid receptor activity, said method comprising administering to said mammal a retinoid antagonist or negative hormone capable of binding to a retinoic acid receptor subtype selected from the group consisting of RAR.sub..alpha., RAR.sub..beta. and RAR.sub..gamma., said antagonist or negative hormone being administered in an amount pharmaceutically effective to provide a therapeutic benefit against said pathological condition in said mammal and wherein the negative hormone or antagonist has the formula ##STR26## wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons; R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
- m is an integer having the value of 0-3;
- o is an integer having the value of 0-3;
- Y is heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said heteroaryl groups being optionally substituted with one or two R.sub.2 group;
- A is (CH.sub.2).sub.q where q 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, COOR8, 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.14 is (R.sub.15).sub.r - phenyl, (R.sub.15).sub.r - naphthyl, or (R.sub.15).sub.r -heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and
- R.sub.15 is independently H, F, Cl, Br, I, NO.sub.2, N(R.sub.8).sub.2, NH(R.sub.8), COR.sub.8, NR.sub.8 CON(R.sub.8).sub.2, OH, OCOR.sub.8, OR.sub.8, CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons.
- 35. A method of treating a pathological condition in a mammal, said condition associated with a retinoic acid receptor activity, said method comprising administering to said mammal a retinoid antagonist or negative hormone capable of binding to a retinoic acid receptor subtype selected from the group consisting of RAR.sub..alpha., RAR.sub..beta. and RAR.sub..gamma., said antagonist or negative hormone being administered in an amount pharmaceutically effective to provide a therapeutic benefit against said pathological condition in said mammal and wherein the negative hormone or antagonist has the formula ##STR27## wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons; R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
- m is an integer having the value of 0-3;
- o is an integer having the value of 0-3;
- Y is heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said heteroaryl groups being optionally substituted with one or two R.sub.2 group;
- A is (CH.sub.2).sub.q where q 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.14 is (R.sub.15).sub.r - phenyl, (R.sub.15).sub.r - naphthyl, or (R.sub.15).sub.r - heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and
- R.sub.15 is independently H, F, Cl, Br, I, NO.sub.2, N(R.sub.8).sub.2, NH(R.sub.8), COR.sub.8, NR.sub.8 CON(R.sub.8).sub.2, OH, OCOR.sub.8, OR.sub.8, CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons.
- 36. A method in accordance with claim 35 wherein in the formula of the antagonist or negative hormone R.sub.1 is H.
- 37. A method of treating a pathological condition in a mammal, said condition associated with a retinoic acid receptor activity, said method comprising administering to said mammal a retinoid antagonist or negative hormone capable of binding to a retinoic acid receptor subtype selected from the group consisting of RAR.sub..alpha., RAR.sub..beta. and RAR.sub..gamma., said antagonist or negative hormone being administered in an amount pharmaceutically effective to provide a therapeutic benefit against said pathological condition in said mammal and wherein the negative hormone or antagonist has the formula ##STR28## wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons; R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
- m is an integer having the value of 0-3;
- o is an integer having the value of 0-3;
- Y is heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said heteroaryl groups being optionally substituted with one or two R.sub.2 group;
- A is (CH.sub.2).sub.q where q 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.14 is (R.sub.15).sub.r - phenyl, (R.sub.15).sub.r - naphthyl, or (R.sub.15).sub.r - heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and
- R.sub.15 is independently H, F, Cl, Br, I, NO.sub.2, N(R.sub.8).sub.2, NH(R.sub.8), COR.sub.8, NR.sub.8 CON(R.sub.8).sub.2, OH, OCOR.sub.8, OR.sub.8, CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons.
- 38. A method of treating a pathological condition in a mammal, said condition associated with a retinoic acid receptor activity, said method comprising administering to said mammal a retinoid antagonist or negative hormone capable of binding to a retinoic acid receptor subtype selected from the group consisting of RAR.sub..alpha., RAR.sub..beta. and RAR.sub..gamma., said antagonist or negative hormone being administered in an amount pharmaceutically effective to provide a therapeutic benefit against said pathological condition in said mammal and wherein the negative hormone or antagonist has the formula ##STR29## wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons; R.sub.2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF.sub.3, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons;
- R.sub.3 is hydrogen, lower alkyl of 1 to 6 carbons or F;
- m is an integer having the value of 0-3;
- o is an integer having the value of 0-3;
- Y is heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said heteroaryl groups being optionally substituted with one or two R.sub.2 group;
- A is (CH.sub.2).sub.q where q 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.2 is lower alkyl, and R.sub.13 is divalent alkyl radical of 2-5 carbons, and
- R.sub.4 is (R.sub.15).sub.r --phenyl, (R.sub.15).sub.r --naphthyl, or (R.sub.15).sub.r -heteroaryl where the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, S and N, r is an integer having the values of 0-5, and
- R.sub.15 is independently H, F, Cl, Br, I, NO.sub.2, N(R.sub.8).sub.2, NH(R.sub.8), COR.sub.8, NR.sub.8 CON(R.sub.8).sub.2, OH, OCOR.sub.8, OR.sub.8, CN, an alkyl group having 1 to 10 carbons, fluoro substituted alkyl group having 1 to 10 carbons, an alkenyl group having 1 to 10 carbons and 1 to 3 double bonds, alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or a trialkylsilyl or trialkylsilyloxy group where the alkyl groups independently have 1 to 6 carbons.
RELATED APPLICATIONS
This application is a divisional of application Ser. No. 08.backslash.871,093 filed on Jun. 9, 1997 now U.S. Pat. No. 5,952,345, which is a divisional of application Ser. No. 08/613,863 filed on Mar. 11, 1996, now U.S. Pat. No. 5,776,699, which claims the benefit of priority under 35 U.S.C. .sctn. 119(e) of the three following U.S. applications, each of which was filed as a nonprovisional application and converted to a provisional application by separate petitions filed on Jan. 31, 1996: application Ser. No. 08/522,778, filed Sep. 1, 1995, now provisional application Ser. No. 60/019,015 application Ser. No. 08/522,778, filed Sep. 1, 1995, now provisional application Ser. No. 60/064,853; and application Ser. No. 08/542,648, filed Oct. 13, 1995, now provisional application Ser. No. 60/020,501. The complete disclosures of these related applications is hereby incorporated herein by this reference thereto.
US Referenced Citations (122)
Foreign Referenced Citations (2)
Number |
Date |
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170105A |
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EPX |
0098591 |
Jan 1984 |
EPX |
Divisions (2)
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871093 |
Jun 1997 |
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613863 |
Mar 1996 |
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