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Details for Patent: 7,432,370

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Details for Patent: 7,432,370

Title:Chiral salt resolution
Abstract: The present application discloses compounds of the formula ##STR00001## wherein R.sup.2 and R.sup.3 are as defined herein. The present application further discloses certain pyrrolol[2,3-d]pyrimidine compounds having the 3R,4R stereochemical configuration shown above. Corresponding pharmaceutical compositions and methods for the treatment or prevention of a disorder or condition selected from organ transplant rejection, xeno transplantation, lupus, multiple sclerosis, rheumatoid arthritis, psoriasis, Type I diabetes and complications from diabetes, cancer, asthma, atopic dermatitis, autoimmune thyroid disorders, ulcerative colitis, Crohn's disease, Alzheimer's disease, leukemia and other autoimmune diseases are also disclosed.
Inventor(s): Wilcox; Glenn E. (Cranston, RI), Flanagan; Mark E. (Gales Ferry, CT), Munchhof; Michael J. (Salem, CT), Vries; Ton (Groningen, NL), Koecher; Christian (St. Ursan, CH)
Assignee: Pfizer Inc. (Groton, CT)
Filing Date:Jun 15, 2004
Application Number:10/869,101
Claims:1. A resolved compound of the formula ##STR00022## or a pharmaceutically acceptable salt thereof, wherein R.sup.2 and R.sup.3 are each independently selected from the group consisting of hydrogen, deuterium, amino, halo, hydroxy, nitro, carboxy, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl, trifluoromethyl, trifluoromethoxy, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.3-C.sub.10)cycloalkyl wherein the alkyl, alkoxy or cycloalkyl groups are optionally substituted by one to three groups selected from halo, hydroxy, carboxy, amino(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylamino, ((C.sub.1-C.sub.6)alkyl).sub.2amino, (C.sub.5-C.sub.9)heteroaryl, (C.sub.2-C.sub.9)heterocycloalkyl, (C.sub.3-C.sub.9)cycloalkyl or (C.sub.6-C.sub.10)aryl; or R.sup.2 and R.sup.3 are each independently (C.sub.3-C.sub.10)cycloalkyl, (C.sub.3-C.sub.10)cycloalkoxy, (C.sub.1-C.sub.6)alkylamino, ((C.sub.1-C.sub.6)alkyl).sub.2amino, (C.sub.6-C.sub.10)arylamino, (C.sub.1-C.sub.6)alkylthio, (C.sub.6-C.sub.10)arylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.6-C.sub.10)arylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.6-C.sub.10)arylsulfonyl, (C.sub.1-C.sub.6)acyl, (C.sub.1-C.sub.6)alkoxy-CO--NH--, (C.sub.1-C.sub.6)alkylamino-CO--, (C.sub.5-C.sub.9)heteroaryl, (C.sub.2-C.sub.9)heterocycloalkyl or (C.sub.6-C.sub.10)aryl wherein the heteroaryl, heterocycloalkyl and aryl groups are optionally substituted by one to three halo, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkyl-CO--NH--, (C.sub.1-C.sub.6)alkoxy-CO--NH--, (C.sub.1-C.sub.6)alkyl-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-CO--NH--(C.sub.1-C.sub.6)alkoxy, carboxy, carboxy(C.sub.1-C.sub.6)alkyl, carboxy(C.sub.1-C.sub.6)alkoxy, benzyloxycarbonyl(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkoxycarbonyl(C.sub.1-C.sub.6)alkoxy, (C.sub.6-C.sub.10)aryl, amino, amino(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxycarbonylamino, (C.sub.6-C.sub.10)aryl(C.sub.1-C.sub.6)alkoxycarbonylamino, (C.sub.1-C.sub.6)alkylamino, ((C.sub.1-C.sub.6)alkyl).sub.2amino, (C.sub.1-C.sub.6)alkylamino(C.sub.1-C.sub.6)alkyl, ((C.sub.1-C.sub.6)alkyl).sub.2amino(C.sub.1-C.sub.6)alkyl, hydroxy, (C.sub.1-C.sub.6)alkoxy, carboxy, carboxy(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)alkoxycarbonyl(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-CO--NH--, (C.sub.1-C.sub.6)alkyl-CO--NH--, cyano, (C.sub.5-C.sub.9)heterocycloalkyl, amino-CO--NH--, (C.sub.1-C.sub.6)alkylamino-CO--NH--, ((C.sub.1-C.sub.6)alkyl).sub.2amino-CO--NH--, (C.sub.6-C.sub.10)arylamino-CO--NH--, (C.sub.5-C.sub.9)heteroarylamino-CO--NH--, (C.sub.1-C.sub.6)alkylamino-CO--NH--(C.sub.1-C.sub.6)alkyl, ((C.sub.1-C.sub.6)alkyl).sub.2amino-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.6-C.sub.10)arylamino-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.9)heteroarylamino-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)alkylsulfonylamino, (C.sub.1-C.sub.6)alkylsulfonylamino(C.sub.1-C.sub.6)alkyl, (C.sub.6-C.sub.10)arylsulfonyl, (C.sub.6-C.sub.10)arylsulfonylamino, (C.sub.6-C.sub.10)arylsulfonylamino(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonylamino, (C.sub.1-C.sub.6)alkylsulfonylamino(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.9)heteroaryl or (C.sub.2-C.sub.9)heterocycloalkyl; wherein the alkyl groups are saturated monovalent hydrocarbon radicals having straight or branched moieties or combinations thereof.

2. A compound according to claim 1, wherein R.sup.2 and R.sup.3 are hydrogen.

3. A compound according to claim 1, wherein the compound is enantiomerically resolved in excess of 90 percent.

4. A resolved compound of the formula ##STR00023## wherein R.sup.2 and R.sup.3 are each independently selected from the group consisting of hydrogen, deuterium, amino, halo, hydroxy, nitro, carboxy, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl, trifluoromethyl, trifluoromethoxy, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.3-C.sub.10)cycloalkyl wherein the alkyl, alkoxy or cycloalkyl groups are optionally substituted by one to three groups selected from halo, hydroxy, carboxy, amino (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylamino, ((C.sub.1-C.sub.6)alkyl).sub.2amino, (C.sub.5-C.sub.9)heteroaryl, (C.sub.2-C.sub.9)heterocycloalkyl, (C.sub.3-C.sub.9)cycloalkyl or (C.sub.6-C.sub.10)aryl; or R.sup.2 and R.sup.3 are each independently (C.sub.3-C.sub.10)cycloalkyl, (C.sub.3-C.sub.10)cycloalkoxy, (C.sub.1-C.sub.6)alkylamino, ((C.sub.1-C.sub.6)alkyl).sub.2amino, (C.sub.6-C.sub.10)arylamino, (C.sub.1-C.sub.6)alkylthio, (C.sub.6-C.sub.10)arylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.6-C.sub.10)arylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.6-C.sub.10)arylsulfonyl, (C.sub.1-C.sub.6)acyl, (C.sub.1-C.sub.6)alkoxy-CO--NH--, (C.sub.1-C.sub.6)alkylamino-CO--, (C.sub.5-C.sub.9)heteroaryl, (C.sub.2-C.sub.9)heterocycloalkyl or (C.sub.6-C.sub.10)aryl wherein the heteroaryl, heterocycloalkyl and aryl groups are optionally substituted by one to three halo, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkyl-CO--NH--, (C.sub.1-C.sub.6)alkoxy-CO--NH--, (C.sub.1-C.sub.6)alkyl-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-CO--NH--(C.sub.1-C.sub.6)alkoxy, carboxy, carboxy(C.sub.1-C.sub.6)alkyl, carboxy(C.sub.1-C.sub.6)alkoxy, benzyloxycarbonyl(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkoxycarbonyl(C.sub.1-C.sub.6)alkoxy, (C.sub.6-C.sub.10)aryl, amino, amino(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxycarbonylamino, (C.sub.6-C.sub.10)aryl(C.sub.1-C.sub.6)alkoxycarbonylamino, (C.sub.1-C.sub.6)alkylamino, ((C.sub.1-C.sub.6)alkyl).sub.2amino, (C.sub.1-C.sub.6)alkylamino(C.sub.1-C.sub.6)alkyl, ((C.sub.1-C.sub.6)alkyl).sub.2amino(C.sub.1-C.sub.6)alkyl, hydroxy, (C.sub.1-C.sub.6)alkoxy, carboxy, carboxy(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)alkoxycarbonyl(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-CO--NH--, (C.sub.1-C.sub.6)alkyl-CO--NH--, cyano, (C.sub.5-C.sub.9)heterocycloalkyl, amino-CO--NH--, (C.sub.1-C.sub.6)alkylamino-CO--NH--, ((C.sub.1-C.sub.6)alkyl).sub.2amino-CO--NH--, (C.sub.6-C.sub.10)arylamino-CO--NH--, (C.sub.5-C.sub.9)heteroarylamino-CO--NH--, (C.sub.1-C.sub.6)alkylamino-CO--NH--(C.sub.1-C.sub.6)alkyl, ((C.sub.1-C.sub.6)alkyl).sub.2amino-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.6-C.sub.10)arylamino-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.9)heteroarylamino-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)alkylsulfonylamino, (C.sub.1-C.sub.6)alkylsulfonylamino(C.sub.1-C.sub.6)alkyl, (C.sub.6-C.sub.10)arylsulfonyl, (C.sub.6-C.sub.10)arylsulfonylamino, (C.sub.6-C.sub.10)arylsulfonylamino(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonylamino, (C.sub.1-C.sub.6)alkylsulfonylamino(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.9)heteroaryl or (C.sub.2-C.sub.9)heterocycloalkyl; wherein the alkyl groups are saturated monovalent hydrocarbon radicals having straight or branched moieties or combinations thereof.

5. A compound according to claim 1, wherein R.sup.2 and are hydrogen.

6. A compound according to claim 4, wherein the compound is enantiomerically resolved in excess of 90 percent.

7. A compound according to claim 5, wherein the compound is enantiomerically resolved in excess of 90 percent.

8. An enantiomerically enriched compound of the formula ##STR00024## wherein R.sup.2 and R.sup.3 are each independently selected from the group consisting of hydrogen, deuterium, amino, halo, hydroxy, nitro, carboxy, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl, trifluoromethyl, trifluoromethoxy, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.3-C.sub.10)cycloalkyl wherein the alkyl, alkoxy or cycloalkyl groups are optionally substituted by one to three groups selected from halo, hydroxy, carboxy, amino (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylamino, ((C.sub.1-C.sub.6)alkyl).sub.2amino, (C.sub.5-C.sub.9)heteroaryl, (C.sub.2-C.sub.9)heterocycloalkyl, (C.sub.3-C.sub.9)cycloalkyl or (C.sub.6-C.sub.10)aryl; or R.sup.2 and R.sup.3 are each independently (C.sub.3-C.sub.10)cycloalkyl, (C.sub.3-C.sub.10)cycloalkoxy, (C.sub.1-C.sub.6)alkylamino, ((C.sub.1-C.sub.6)alkyl).sub.2amino, (C.sub.6-C.sub.10)arylamino, (C.sub.1-C.sub.6)alkylthio, (C.sub.6-C.sub.10)arylthio, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.6-C.sub.10)arylsulfinyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.6-C.sub.10)arylsulfonyl, (C.sub.1-C.sub.6)acyl, (C.sub.1-C.sub.6)alkoxy-CO--NH--, (C.sub.1-C.sub.6)alkylamino-CO--, (C.sub.5-C.sub.9)heteroaryl, (C.sub.2-C.sub.9)heterocycloalkyl or (C.sub.6-C.sub.10)aryl wherein the heteroaryl, heterocycloalkyl and aryl groups are optionally substituted by one to three halo, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkyl-CO--NH--, (C.sub.1-C.sub.6)alkoxy-CO--NH--, (C.sub.1-C.sub.6)alkyl-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-CO--NH--(C.sub.1-C.sub.6)alkoxy, carboxy, carboxy(C.sub.1-C.sub.6)alkyl, carboxy(C.sub.1-C.sub.6)alkoxy, benzyloxycarbonyl(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkoxycarbonyl(C.sub.1-C.sub.6)alkoxy, (C.sub.6-C.sub.10)aryl, amino, amino(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxycarbonylamino, (C.sub.6-C.sub.10)aryl(C.sub.1-C.sub.6)alkoxycarbonylamino, (C.sub.1-C.sub.6)alkylamino, ((C.sub.1-C.sub.6)alkyl).sub.2amino, (C.sub.1-C.sub.6)alkylamino(C.sub.1-C.sub.6)alkyl, ((C.sub.1-C.sub.6)alkyl).sub.2amino(C.sub.1-C.sub.6)alkyl, hydroxy, (C.sub.1-C.sub.6)alkoxy, carboxy, carboxy(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)alkoxycarbonyl(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-CO--NH--, (C.sub.1-C.sub.6)alkyl-CO--NH--, cyano, (C.sub.1-C.sub.9)heterocycloalkyl, amino-CO--NH--, (C.sub.1-C.sub.6)alkylamino-CO--NH--, ((C.sub.1-C.sub.6)alkyl).sub.2amino-CO--NH--, (C.sub.6-C.sub.10)arylamino-CO--NH--, (C.sub.5-C.sub.9)heteroarylamino-CO--NH--, (C.sub.1-C.sub.6)alkylamino-CO--NH--(C.sub.1-C.sub.6)alkyl, ((C.sub.1-C.sub.6)alkyl).sub.2amino-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.6-C.sub.10)arylamino-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.9)heteroarylamino-CO--NH--(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)alkylsulfonylamino, (C.sub.1-C.sub.6)alkylsulfonylamino(C.sub.1-C.sub.6)alkyl, (C.sub.6-C.sub.10)arylsulfonyl, (C.sub.6-C.sub.10)arylsulfonylamino, (C.sub.6-C.sub.10)arylsulfonylamino(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonylamino, (C.sub.1-C.sub.6)alkylsulfonylamino(C.sub.1-C.sub.6)alkyl, (C.sub.5-C.sub.9)heteroaryl or (C.sub.2-C.sub.9)heterocycloalkyl; wherein the alkyl groups are saturated monovalent hydrocarbon radicals having straight or branched moieties or combinations thereof.

9. A compound according to claim 8, wherein R.sup.2 and R.sup.3 are hydrogen.

10. A compound according to claim 8, wherein the compound is enantiomerically enriched in excess of 90 percent.

11. A compound according to claim 9, wherein the compound is enantiomerically enriched in excess of 90 percent.
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