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US 6,747,039 B2Granted
Aza-benzothiopyranoindazoles with antitumor activity
AssigneeAlbany Molecular Research, Inc.
InventorSimon N. Haydar
Life of this patent
Estimating the term…
Abstract
The present invention relates to a group of aza-anthrapyrazole compounds having antitumor activity, and processes for their preparation. Compositions containing the aza-anthrapyrazole compounds and methods of treating tumors and cancer in mammals with the compounds of the present invention are also disclosed.
Claims52
A compound having the formula:
- where:
- W is selected from the group consisting of S, SO, and SO2;
- Q is a 5- or 6-membered aromatic ring having at least one atom selected from the group consisting of N and S;
- A is selected from the group consisting of:
- hydrogen;
- C1-C4 linear, branched, or cyclic alkyl which is substituted or unsubstituted;
- C1-C4 linear or branched alkoxy which is substituted or unsubstituted;
- hydroxy;
- C(O)H;
- C(O)OR1;
- SO2R1;
- (CH2)nNH(CH2)mCH3;
- (CH2)nN((CH2)mCH3)(CH2)pCH3;
- and (CH2)nD;
- B is selected in the group consisting of:
- hydrogen;
- C1-C4 linear, branched, or cyclic alkyl which is substituted or unsubstituted;
- C1-C4 linear or branched alkoxy which is substituted or unsubstituted;
- hydroxy;
- (CH2)nNH(CH2)mCH3;
- (CH2)nN((CH2)mCH3)(CH2)pCH3;
- and (CH2)nD;
- R1 is selected from a group consisting of C1-C10 alkyl, phenyl, and phenyl alkyl, as free bases;
- n is 2-3;
- m is 0-3;
- p is 0-3;
- and
- D is selected from the group consisting of:
- hydroxy;
- C1-C4 linear or branched alkoxy which is substituted or unsubstituted;
- and a 5- or 6-member aromatic or non-aromatic heterocyclic ring containing a sulfur, oxygen, or nitrogen heteroatom or
- pharmaceutically acceptable salts.
29 more elements
A process for preparation of a product compound of the formula:
- where:
- one or more of X, Y, Z, or T═N;
- W is selected from the group consisting of S, SO, and SO2;
- A is selected from the group consisting of:
- hydrogen;
- C1-C4 linear, branched, or cyclic alkyl which is substituted or unsubstituted;
- C1-C4 linear or branched alkoxy which is substituted or unsubstituted;
- hydroxy;
- C(O)H, C(O)OR1, SO2R1;
- (CH2)nNH(CH2)mCH3;
- (CH2)nN((CH2)mCH3)(CH2)pCH3;
- and (CH2)nD;
- B is selected from the group consisting of:
- hydrogen;
- C1-C4 linear, branched, or cyclic alkyl which is substituted or unsubstituted;
- C1-C4 linear or branched alkoxy which is substituted or unsubstituted;
- hydroxy;
- (CH2)nNH(CH2)mCH3;
- (CH2)nN((CH2)mCH3)(CH2)pCH3;
- and (CH2)nD;
- R1 is selected from a group consisting of C1-C10 alkyl, phenyl, and phenyl alkyl, as free bases;
- n is 2-3;
- m is 0-3;
- p is 0-3;
- and
- D is selected from the group consisting of:
- hydroxy;
- C1-C4 linear or branched alkoxy which is substituted or unsubstituted;
- and a 5- or 6-member aromatic or non-aromatic heterocyclic ring containing a sulfur, oxygen, or nitrogen heteroatom;
- or
- pharmaceutically acceptable salts thereof, said process comprising:
- transforming a first intermediate compound of the formula:
- under conditions effective to form the product compound.
30 more elements
A process for preparation of a product compound of the formula:
- where:
- A is selected from the group consisting of:
- hydrogen;
- C1-C4 linear, branched, or cyclic alkyl which is substituted or unsubstituted;
- C1-C4 linear or branched alkoxy which is substituted or unsubstituted;
- hydroxy;
- C(O)H;
- C(O)OR1;
- SO2R1;
- (CH2)nNH(CH2)mCH3;
- (CH2)nN((CH2)mCH3)(CH2)pCH3;
- and (CH2)nD;
- B is selected in the group consisting of:
- hydrogen;
- C1-C4 linear, branched, or cyclic alkyl which is substituted or unsubstituted;
- C1-C4 linear or branched alkoxy which is substituted or unsubstituted;
- hydroxy;
- (CH2)nNH(CH2)mCH3;
- (CH2)nN((CH2)mCH3)(CH2)pCH3;
- and (CH2)nD;
- R1 is selected from a group consisting of C1-C10 alkyl, phenyl, and phenyl alkyl, as free bases;
- n is 2-3;
- m is 0-3;
- p is 0-3;
- and
- D is selected from the group consisting of:
- hydroxy;
- C1-C4 linear or branched alkoxy which is substituted or unsubstituted;
- and a 5- or 6-member aromatic or non-aromatic heterocyclic ring containing a sulfur, oxygen, or nitrogen heteroatom;
- or
- a pharmaceutically acceptable salt thereof, said process comprising:
- transforming a first intermediate compound of the formula:
- under conditions effective to form the product compound.
30 more elements
A process for preparation of a product compound of the formula:
- where:
- A is selected from the group consisting of:
- hydrogen;
- C1-C4 linear, branched, or cyclic alkyl which is substituted or unsubstituted;
- C1-C4 linear or branched alkoxy which is substituted or unsubstituted;
- hydroxy;
- C(O)H;
- C(O)OR1;
- SO2R1;
- (CH2)nNH(CH2)mCH3;
- (CH2)nN((CH2)mCH3)(CH2)pCH3;
- and (CH2)nD;
- B is selected in the group consisting of:
- hydrogen;
- C1-C4 linear, branched, or cyclic alkyl which is substituted or unsubstituted;
- C1-C4 linear or branched alkoxy which is substituted or unsubstituted;
- hydroxy;
- (CH2)nNH(CH2)mCH3;
- (CH2)nN((CH2)mCH3)(CH2)pCH3;
- and (CH2)nD;
- R1 is selected from a group consisting of C1-C10 alkyl, phenyl, and phenyl alkyl, as free bases;
- n is 2-3;
- m is 0-3;
- p is 0-3;
- E is OCH3 or Cl;
- and
- D is selected from the group consisting of:
- hydroxy;
- C1-C4 linear or branched alkoxy which is substituted or unsubstituted;
- and a 5- or 6-member aromatic or non-aromatic heterocyclic ring containing a sulfur, oxygen, or nitrogen heteroatom;
- or
- a pharmaceutically acceptable salt thereof, said process comprising:
- transforming a first intermediate compound of the formula:
- under conditions effective to form the product compound wherein E is Cl.
31 more elements
Dependencies are inferred from the claim text.