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US 2003/0229130 A1Published application
Imidazolinylmethyl aralkylsulfonamides
AssigneeRoche Palo Alto LLC
InventorsMichael Patrick Dillon, Clara Jeou Jen Lin, Counde O'Yang, Xiaoming Zhang
Life of this patent
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Abstract
Compounds of the Formula: 1 where R1-R6 are those defined herein and methods for producing the same. Also provided are pharmaceutical compositions comprising a Compound of Formula I and methods for their use as therapeutic agents.
Claims25
A compound of the formula:
- 117
- a pharmaceutically acceptable salt or a prodrug thereof,
- wherein
- R1 is alkyl or —NR7R8, where each of R7 and R8 is independently hydrogen or alkyl;
- R2 is hydrogen or alkyl;
- each of R3, R4, R5, and R6 is independently hydrogen, halide, alkyl, —OR9 (where R9 is hydrogen, alkyl, a hydroxy protecting group, or cycloalkylalkyl), —SR10 (where R10 is hydrogen or alkyl), or —NR11R12 (where each of R11 and R12 is independently hydrogen, alkyl, or a nitrogen protecting group), provided R3, R4, R5, and R6 are not all simultaneously alkyl);
- or R3 and R4 together with atoms to which they are attached to form heterocyclyl, heteroaryl, or cycloalkyl;
- and
- R14 is hydrogen, lower alkyl or —OR15, where R15 is hydrogen, lower alkyl, or a hydroxy protecting group.
6 more elements
A method for producing an imidazolin-2-ylmethyl-substituted aromatic compound of the formula:
- 119
- said method comprising contacting a nitrile compound of the formula:
- 120
- with ethylene diamine to produce the imidazolin-2-ylmethyl-substituted aromatic compound, wherein
- R1 is alkyl, —NR7R8, where each of R7 and R is independently hydrogen or alkyl;
- R2 is hydrogen or alkyl;
- each of R3, R4, R5, and R6 is independently hydrogen, halide, alkyl, —OR9, where R9 is hydrogen, alkyl, a hydroxy protecting group, or cycloalkylalkyl, —SR10, where R10 is hydrogen or alkyl, or —NR11R12, where each of R11 and R12 is independently hydrogen, alkyl, or a nitrogen protecting group, provided R3, R4, R5, and R6 are not all simultaneously alkyl);
- or R3 and R4 together with atoms to which they are attached to form heterocyclyl, heteroaryl, or cycloalkyl;
- and
- R14 is hydrogen, lower alkyl or —OR15, where R15 is hydrogen, lower alkyl, or a hydroxy protecting group.
7 more elements
A method for producing an imidazolin-2-ylmethyl-substituted aromatic compound of the formula:
- 121
- said method comprising contacting an ester compound of the formula:
- 122
- with ethylene diamine in the presence of a trialkylaluminum to produce the imidazolin-2-ylmethyl-substituted aromatic compound,
- wherein
- R1 is alkyl, —NR7R8, where each of R7 and R8 is independently hydrogen or alkyl;
- R2 is hydrogen or alkyl;
- each of R3, R4, R5, and R6 is independently hydrogen, halide, alkyl, —OR9, where R9 is hydrogen, alkyl, a hydroxy protecting group, or cycloalkylalkyl, —SR10, where R10 is hydrogen or alkyl;
- or —NR11R12, where each of R and R12 is independently hydrogen, alkyl, or a nitrogen protecting group;
- or R3 and R4 together with atoms to which they are attached to form heterocyclyl, heteroaryl, or cycloalkyl;
- R13 is alkyl;
- and
- R14 is hydrogen, lower alkyl or —OR15, where R15 is hydrogen, lower alkyl, or a hydroxy protecting group.
10 more elements
Dependencies are inferred from the claim text.