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US 7,115,589 B2Granted
Purine derivatives
AssigneeARIAD Pharmaceuticals, Inc.
InventorsManfred Weigele, Tomi K. Sawyer, Regine Bohacek, William C. Shakespeare, Rajeswari Sundaramoorthi, Yihan Wang, David C. Dalgarno, Chester A. Metcalf, III
Life of this patent
Estimating the term…
Abstract
This invention relates to compounds of the general formula: in which RA, RB, RC and RD are as defined herein, and to their preparation and use. In these compounds, RB is an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety which comprises one or more phosphorus-containing moieties.
Claims20
A compound of formula (Ia) (or a salt or ester, or salt of an ester, thereof):
- wherein
- RA is Mx-aryl or Mx-heterocycle where M is a substituted or unsubstituted methylene, x is an integer from 1 to 6, the aryl moiety may bear one or more substituents, and the heterocycle is a substituted or unsubstituted, aromatic or nonaromatic heterocyclic moiety comprising a 5- to 7-membered ring bearing one or more heteroatoms;
- RB comprises an aryl, or heteroaryl moiety bearing at least one a substituent of Series llb:
- RC is hydrogen, halogen, an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety, or —ZR, wherein Z is —O—, —S—, or NR, wherein each occurrence of R without a further alphanumeric superscript is independently hydrogen, or a substituted or unsubstituted aliphatic, heteroaliphatic, aryl, or heteroaryl moiety;
- each occurrence of K is independently —O— or —S—;
- each occurrence of Y is independently —O—, —S—, —NR— or a chemical bond;
- each occurrence of R (without a further alphanumeric superscript) is independently hydrogen, or a substituted or unsubstituted aliphatic, heteroaliphatic, aryl, or heteroaryl moiety;
- each occurrence of R1 is independently a substituted or unsubstituted aliphatic, heteroaliphatic, aryl, or heteroaryl moiety, or, except in YR1 moieties in which Y is a covalent bond, R1 may also be H;
- each occurrence of R2 is independently R1, —PK(YR1)(YR1), —SO2(YR1) or —C(O)(YR1);
- each occurrence of R6 independently represents an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety;
- each occurrence of G is independently —O—, —S—, —NR— or Mx;
- and,
- each occurrence of MY is independently a methine group or a lower alkyl moiety which contains a methine group and optionally may be further substituted,
- wherein in each of the foregoing groups each aliphatic or heteroaliphatic moiety may be branched or unbranched, cyclic or acyclic and substituted or unsubstituted, and each aryl and heteroaryl moiety may be substituted or unsubstituted.
11 more elements
A compound of formula (lb) (or a salt or ester, or salt of an ester, thereof):
- wherein
- RA is hydrogen, or an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety;
- RC is an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety;
- RD is hydrogen, halogen, an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety, or —ZR;
- wherein Z is —O—, —S—, or NR, wherein each occurrence of R without a further alphanumeric superscript is independently hydrogen, or a substituted or unsubstituted aliphatic, heteroaliphatic, aryl, or heteroaryl moiety;
- R8 is selected from the moieties of Series II:
- is selected from the moieties of Series III:
- R3 represents from 0–3 substituents independently selected from the group consisting of halogen, R, —GR, —CO(YR), amido, amidino, cyano, nitro, azido, sulfamoyl, sulfonamido, and substituents of Series II;
- M is a substituted or unsubstituted methylene;
- x is an integer from 1 to 6;
- each occurrence of K is independently —O— or —S—;
- each occurrence of Y is independently —O—, —S—, —NR— or a chemical bond;
- each occurrence of R1 is independently a substituted or unsubstituted aliphatic, heteroaliphatic, aryl, or heteroaryl moiety, or, except in YR1 moieties in which Y is a covalent bond, R1 may also be H;
- each occurrence of R2 is independently R1, —PK(YR1)(YR1), —SO2(YR1) or —C(O)(YR1);
- each occurrence of G is independently —O—, —S—, —NR— or Mx;
- and,
- each occurrence of MY is independently a methine group or a lower alkyl moiety which contains a methine group and optionally may be further substituted;
- wherein in each of the foregoing groups each aliphatic or heteroaliphatic moiety may be branched or unbranched, cyclic or acyclic and substituted or unsubstituted, and each aryl and heteroaryl moiety may be substituted or unsubstituted;
- with the following provisos:
- (1) RD is a moiety other than one comprising a substituted or unsubstituted arylene moiety (in which up to two methine carbons may be replaced by nitrogen atoms), a C3–7 cycloalkylene moiety (which may contain nitrogen atoms in place of up to two ring carbons), an indanylene moiety, or a 1,2,3,4-tetrahydronaphthylene moiety;
- (2) RD is a moiety other than one bearing a cyano group or an N-substituted or unsubstituted amino, amidino, guanidino or guanidinoalkyl group;
- RC is covalently attached through a C—C bond to the carbon atom at ring position 2 of the purine ring system.
19 more elements
The compound (or a salt or ester, or salt of an ester, thereof) of the formula:
- wherein
- RA is hydrogen, or an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety;
- RC is hydrogen, halogen, an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety, or —ZR, wherein Z is —O—, —S—, or NR, wherein each occurrence of R without a further alphanumeric superscript is independently hydrogen, or a substituted or unsubstituted aliphatic, heteroaliphatic, aryl, or heteroaryl moiety;
- RD is hydrogen, halogen, an aliphatic, heteroaliphatic, aryl, or heteroaryl moiety, or —ZR, with the proviso that RD does not bear a cyano group or an N-substituted or unsubstituted amino, amidino, guanidino or guanidinoalkyl group;
- each R6 is independently aliphatic, heteroaliphatic, aryl, or heteroaryl and wherein in each of the foregoing groups each aliphatic or heteroaliphatic moiety may be branched or unbranched, cyclic or acyclic and substituted or unsubstituted, and each aryl and heteroaryl moiety may be substituted or unsubstituted.
2 more elements
Dependencies are inferred from the claim text.