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Details for Patent: 7,321,063

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Details for Patent: 7,321,063

Title:Sulfonamide inhibitors of aspartyl protease
Abstract: The present invention relates to a novel class of sulfonamides which are aspartyl protease inhibitors. In one embodiment, this invention relates to a novel class of HIV aspartyl protease inhibitors characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting HIV-1 and HIV-2 protease activity and consequently, may be advantageously used as anti-viral agents against the HIV-1 and HIV-2 viruses. This invention also relates to methods for inhibiting the activity of HIV aspartyl protease using the compounds of this invention and methods for screening compounds for anti-HIV activity.
Inventor(s): Tung; Roger D (Arlington, MA), Murcko; Mark A (Holliston, MA), Bhisetti; Govinda R (Lexington, MA)
Assignee: Vertex Pharmaceuticals Incorporated (Cambridge, MA)
Filing Date:Feb 24, 2004
Application Number:10/786,997
Claims:1. A compound of formula I: ##STR00654## wherein: A is selected from the group consisting of --R.sup.1--C.sub.1-C.sub.6 alkyl, which may be optionally substituted with one or more groups selected from the group consisting of hydroxy, C.sub.1-C.sub.4 alkoxy, --NR.sup.2--CO--N(R.sup.2)(R.sup.2) and --CO--N(R.sup.2)(R.sup.2); each R.sup.1 is independently selected from the group consisting of --C(O)--, --S(O).sub.2--, --C(O)--C(O)--, --O--C(O)--, --O--S(O).sub.2, --NR.sup.2--S(O).sub.2--, --NR.sup.2--C(O)-- and --NR.sup.2--C(O)--C(O)--; each R.sup.2 is independently selected from the group consisting of H and C.sub.1-C.sub.3 alkyl optionally substituted with Ar; with the proviso that when R.sup.2 is C.sub.1-C.sub.3 alkyl substituted with Ar, said Ar may not be substituted with an Ar-containing moiety; B, when present, is --N(R.sup.2)--C(R.sup.3)(R.sup.3)--C(O)--; x is 0 or 1; each R.sup.3 is independently selected from the group consisting of H, Het, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.6 cycloalkyl and C.sub.5-C.sub.6 cycloalkenyl, wherein any member of said R.sup.3, except H, may be optionally substituted with one or more substituents selected from the group consisting of --OR.sup.2, --C(O)--NH--R.sup.2, --S(O).sub.n--N(R.sup.2)(R.sup.2), Het, --CN, --SR.sup.2, --CO.sub.2R.sup.2, NR.sup.2--C(O)--R.sup.2; each n is independently 1 or 2; D and D' are independently selected from the group consisting of Ar; C.sub.1-C.sub.4 alkyl, which may be optionally substituted with one or more groups selected from C.sub.3-C.sub.6 cycloalkyl, --OR.sup.2, --R.sup.3, --O--Ar and Ar; C.sub.2-C.sub.4 alkenyl, which may be optionally substituted with one or more groups selected from the group consisting of C.sub.3-C.sub.6 cycloalkyl, --OR.sup.2, --R.sup.3, --O--Ar and Ar; C.sub.3-C.sub.6 cycloalkyl, which may be optionally substituted with or fused with Ar; and C.sub.5-C.sub.6 cycloalkenyl, which may be optionally substituted with or fused with Ar; each Ar is independently selected from the group consisting of phenyl; 3-6 membered carbocyclic ring, wherein said carbocyclic ring may be saturated or unsaturated and optionally substituted with one or more groups selected from the group consisting of oxo, --OR.sup.2, --R.sup.2, --N(R.sup.2)(R.sup.2), --N(R.sup.2)--C(O)--R.sup.2, C.sub.1-C.sub.3 alkyl substituted with --OH and optionally substituted with Ar, --CN, --CO.sub.2R.sup.2, --C(O)--N(R.sup.2)(R.sup.2), halo and --CF.sub.3; E is selected from the group consisting of Het; O-Het; Het-Het; --O--R.sup.3; --NR.sup.2R.sup.3; C.sub.1-C.sub.6 alkyl, which may be optionally substituted with one or more groups selected from the group consisting of R.sup.4 and Het; C.sub.2-C.sub.6 alkenyl, which may be optionally substituted with one or more groups selected from the group consisting of R.sup.4 and Het; C.sub.3-C.sub.6 saturated carbocycle, which may optionally be substituted with one or more groups selected from the group consisting of R.sup.4 and Het; and C.sub.5-C.sub.6 unsaturated carbocycle, which may optionally be substituted with one or more groups selected from the group consisting of R.sup.4 and Het; each Het is independently selected from the group consisting of C.sub.3-C.sub.7 cycloalkyl; C.sub.5-C.sub.7 cycloalkenyl; C.sub.6-C.sub.10 aryl; and 5-7 membered saturated or unsaturated heterocycle, containing one heteroatom selected from N, N(R.sup.2), O, S and S(O).sub.n, wherein said heterocycle may optionally be benzofused; and wherein any member of said Het may be optionally substituted with one or more substituents selected from the group consisting of oxo, --OR.sup.2, --R.sup.2, --N(R.sup.2)(R.sup.2), --R.sup.2--OH, --CN, --CO.sub.2R.sup.2, --C(O)--N(R.sup.2)(R.sup.2), --S(O).sub.2--N(R.sup.2)(R.sup.2), --N(R.sup.2)--C(O)--R.sub.2, --C(O)--R.sup.2, --S(O).sub.n--R.sup.2, --OCF.sub.3, --S(O).sub.n--Ar, methylenedioxy, --N(R.sup.2)--S(O).sub.2(R.sup.2), halo, --CF.sub.3, --NO.sub.2, Ar and --O--Ar; and each R.sup.4 is independently selected from the group consisting of --OR.sup.2, --C(O)--NHR.sup.2, --S(O).sub.2--NHR.sup.2, halo, --NR.sup.2--C(O)--R.sup.2 and --CN.

2. The compound according to claim 1, characterized in that said compound has the structure of formula XXII: ##STR00655## and A, D' and E are defined as in claim 1.

3. The compound according to claim 1, characterized in that said compound has the structure of formula XXXI: ##STR00656## and A, R.sup.3, D' and E are defined as in claim 1.

4. A compound according to claim 1, wherein: A is selected from the group consisting of --R.sup.1-C.sub.1-C.sub.6 alkyl, which may be optionally substituted with one or more groups selected from the group consisting of hydroxy, C.sub.1-C.sub.4 alkoxy; each R.sup.1 is independently selected from the group consisting of --C(O)--, --S(O).sub.2--, --C(O)--C(O)--, --O--CO--, --O--S(O).sub.2-- and --NR.sup.2--S(O).sub.2--; each R.sup.2 is independently selected from the group consisting of H and C.sub.1-C.sub.3 alkyl; B, when present, is --NH--CH(R.sup.3)--C(O)--; x is 0 or 1; R.sup.3 is selected from the group consisting of Het, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.3-C.sub.6 cycloalkyl and C.sub.5-C.sub.6 cycloalkenyl, wherein any member of said R.sup.3 may be optionally substituted with one or more substituents selected from the group consisting of --OR.sup.2, --C(O)--NH--R.sup.2, --S(O).sub.n--N(R.sup.2).sub.2, Het and --CN; n is 1 or 2; D and D' are independently selected from the group consisting of Ar; C.sub.1-C.sub.4 alkyl, which may be optionally substituted with C.sub.3-C.sub.6 cycloalkyl or Ar; C.sub.2-C.sub.4 alkenyl, which may be optionally substituted with C.sub.3-C.sub.6 cycloalkyl or Ar; C.sub.3-C.sub.6 cycloalkyl, which may be optionally substituted or fused with Ar; and C.sub.5-C.sub.6 cycloalkenyl, which may be optionally substituted or fused with Ar; Ar is selected from the group consisting of phenyl; 3-6 membered carbocyclic ring wherein said carbocyclic ring may be saturated or unsaturated and optionally substituted with one or more groups selected from the group consisting of oxo, --OR.sup.2, --R.sup.2, --N(R.sup.2).sub.2, --N(R.sup.2)--C(O)R.sup.2, --R.sup.2--OH, --CN, --CO.sub.2R.sup.2, --C(O)--N(R.sup.2).sub.2, halo and --CF.sub.3; E is selected from the group consisting of Het; --O--R.sup.3; --NR.sup.2R.sup.5; C.sub.1-C.sub.6 alkyl, which may be optionally substituted with one or more R.sup.4 or Het; C.sub.2-C.sub.6 alkenyl, which may be optionally substituted with one or more R.sup.4 or Het; C.sub.3-C.sub.6 saturated carbocycle, which may optionally be substituted with one or more R.sup.4 or Het; and C.sub.5-C.sub.6 unsaturated carbocycle, which may optionally be substituted with one or more R.sup.4 or Het; each Het is independently selected from the group consisting of C.sub.3-C.sub.7 cycloalkyl; C.sub.5-C.sub.7 cycloalkenyl; C.sub.6-C.sub.10 aryl; and 5-7 membered saturated or unsaturated heterocycle, containing one heteroatom selected from N, O and S, which may optionally be benzofused; wherein any member of said Het may be optionally substituted with one or more substituents selected from the group consisting of oxo, --OR.sup.2, --R.sup.2, --N(R.sup.2).sub.2, --R.sup.2--OH, --CN, --CO.sub.2R.sup.2, --C(O)--N(R.sup.2).sub.2 and --S(O).sub.2--N(R.sup.2).sub.2; each R.sup.4 is independently selected from the group consisting of --OR.sup.2, --C(O)--NHR.sup.2, --S(O).sub.2--NHR.sup.2, halo and --CN; and each R.sup.5 is independently selected from the group consisting of H and R.sup.3.

5. The compound according to claim 1, wherein: R.sup.3 is selected from the group consisting of C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.5-C.sub.6 cycloalkyl, C.sub.5-C.sub.6 cycloalkenyl and a 5-6 membered saturated or unsaturated heterocycle, wherein any member of said R.sup.3 may optionally be substituted with one or more substituents selected from the group consisting of --OR.sup.2, --C(O)--NH--R.sup.2, --S(O).sub.nN(R.sup.2)(R.sup.2), Het, --CN, --SR.sup.2, --C(O).sub.2R.sup.2, NR.sup.2--C(O)--R.sup.2; and D' is selected from the group consisting of C.sub.1-C.sub.3 alkyl and C.sub.3 alkenyl, wherein said alkyl or alkenyl may optionally be substituted with one or more groups selected from the group consisting of C.sub.3-C.sub.6 cycloalkyl, --OR.sup.2, --O--Ar and Ar.

6. The compound according to claim 1, wherein said compound has a molecular weight less than or equal to about 700 g/mol.

7. A compound according to claim 6, wherein said compound has a molecular weight less than or equal to about 600 g/mol.
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