Calcium receptor-active molecules

A compound having the chemical formula:

• ##STR16## wherein alk is either n-propylene, 2,4-butylene, or 1,3-butylene;
• R.sub.1 is a lower alkyl of from 1 to 3 carbon atoms;
• R.sub.2 is either naphthyl or a phenyl substituted with 1 to 5 substituents, and R.sub.3 is either cyclohexyl, naphthyl, or a phenyl optionally substituted with 1 to 5 substituents;
• wherein each of said R.sub.2 substituents and each of said R.sub.3 substituents are independently selected from the group consisting of:
• OCF.sub.3, lower alkyl of 1 to 3 carbon atoms, lower haloalkyl of 1 to 3 carbon atoms substituted with 1 to 7 halogen atoms, lower alkoxy of 1 to 3 carbon atoms, halogen, nitro, amino, alkylamino, amido, lower alkylamido of 1 to 3 carbon atoms, cyano, hydroxy, acyl of 2 to 4 carbon atoms, lower hydroxyalkyl of 1 to 3 carbon atoms, and lower thioalkyl of 1 to 3 carbon atoms;
• provided that R.sub.2 is not 4-OH-phenyl;
• or
• a pharmaceutically acceptable acid addition salt or complex thereof.

A compound represented by a formula selected from the group consisting of ##STR22## wherein m is independently an integer of 0 to 5 for naphthyl rings and m is independently an integer of 1 to 5 for phenyl rings;

• x is independently selected from the group consisting of --Br, --C1, --F, --I, --CN, --NO.sub.2, --OR, --NR.sub.2, --CF.sub.3, --SR, --S(O)R, --S(O).sub.2 R, --C(O)R, --OC(O)R, --C(O)OR, --NRC(O)R, C(O)NR.sub.2, methyl and isopropyl radicals;
• provided that the X substituent on the phenyl ring of the Ph-CHR-group is other than hydroxy, 4-OCH.sub.3, or 4-CH.sub.3 ;
• and
• each R is independently either a hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, --CF.sub.3, --CF.sub.2 H, --CFH.sub.2, --CH.sub.2 CF.sub.3 or phenyl radical;
• provided that if said compound has the chemical formula:
• ##STR23## wherein the naphthyl is either unsubstitued or substituted with a lower alkyl or halogen and only one substituent is present on the phenyl, then said one substituent is not lower alkyl or halogen;
• or a pharmaceutically acceptable acid addition salt or complex thereof.

A compound having the chemical formula:

• ##STR32## wherein alk is 1,1-ethylidine or methylene;
• R.sub.1 is lower alkyl of from 1 to 3 carbon atoms or lower haloalkyl of from 1 to 3 carbon atoms substituted with from 1 to 7 halogen atoms;
• and
• R.sub.2 and R.sub.3 are independently selected monocyclic or bicyclic carbocyclic aryl or cycloalkyl groups, having 5- to 7-membered rings optionally substituted with 1 to 5 substituents independently selected from the group consisting of:
• OCF.sub.3, lower alkyl of 1 to 3 carbon atoms, lower haloalkyl of 1 to 3 carbon atoms substituted with 1 to 7 halogen atoms, lower alkoxy of 1 to 3 carbon atoms, halogen, nitro, amino, alkylamino, amido, lower alkylamido of 1 to 3 carbon atoms, cyano, hydroxy, acyl of 2 to 4 carbon atoms, lower hydroxyalkyl of 1 to 3 carbon atoms, and lower thioalkyl of 1 to 3 carbon atoms;
• provided that R.sub.2 is not and unsubstituted phenyl and R.sub.3 is not an unsubstituted phenyl;
• further provided that if alk is methylene then either, R.sub.2 and R.sub.3 are both substituted phenyls, R.sub.3 does not contain a OH substituent, and R.sub.3 is not 4-OCH.sub.3 -phenyl, or 4-CH.sub.3 -phenyl, or R.sub.2 is an optionally substituted naphthyl and R.sub.3 is a substituted phenyl not containing an OH substituent;
• and
• further provided that if one of R.sub.2 or R.sub.3 is naphthyl or naphthyl substituted with a lower alkyl of 1 to 3 carbons or halogen and the other of R.sub.2 or R.sub.3 is phenyl, then the phenyl has 1-5 substituents and if one substituent is present, then the one substituent is other than 2-OH, lower alkyl of 1 to 3 carbons or halogen;
• or a pharmaceutically acceptable acid addition salt or complex thereof.

A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound having the chemical formula:

• ##STR46## wherein alk is a straight- or branched-chain alkylene of from 0 to 6 carbon atoms;
• R.sub.1 is a lower alkyl of from 1 to 3 carbon atoms or a lower haloalkyl of from 1 to 3 carbon atoms substituted with from 1 to 7 halogen atoms;
• and
• R.sub.2 and R.sub.3 are each independently selected monocyclic or bicyclic carbocyclic aryl or cycloalkyl groups, having 5- to 7-membered rings optionally substituted with 1 to 5 substituents each independently selected from the group consisting of:
• OCF.sub.3, lower alkyl of 1 to 3 carbon atoms, lower haloalkyl of 1 to 3 carbon atoms substituted with 1 to 7 halogen atoms, lower alkoxy of 1 to 3 carbon atoms, halogen, nitro, amino, alkylamino, amido, lower alkylamido of 1 to 3 carbon atoms, cyano, hydroxy, acyl of 2 to 4 carbon atoms, lower hydroxyalkyl of 1 to 3 carbon atoms, and lower thioalkyl of 1 to 3 carbon atoms;
• provided that if R.sub.2 is phenyl, then R.sub.2 is substituted with 1 to 5 substituents;
• further provided that if R.sub.3 is cycloalk and alk is --CH.sub.2 --, then R.sub.2 is not 4 aminophenyl;
• or a pharmaceutically acceptable acid addition salt or complex thereof.