process of making 3-phenyl-1-methylenedioxyphenyl-indane-2-carboxylic acid derivatives
First Claim
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1. A compound of the Formula (u):
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where R3 and R4 are independently H, OH, protected OH, C1-8alkoxy, I, Br, Cl, F, CF3 or C1-6alkyl and R9 is an oxy protecting group.
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Abstract
Invented is an improved process for preparing aromatic ring-fused cyclopentane derivatives. Preferred compounds prepared by this invention are indane carboxylates and cyclopentanopyridine derivatives. The most preferred compounds prepared by this invention are (+)(1S, 2R, 3S)-3-[2-(2-hydroxyeth-1-yloxy)-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid and pharmaceutically acceptable salts thereof and (+)(1S, 2R, 3S)-3-(2-carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid and pharmaceutically acceptable salts thereof. Also invented are novel intermediates useful in preparing these compounds.
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4 Claims
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1. A compound of the Formula (u):
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where R3 and R4 are independently H, OH, protected OH, C1-8alkoxy, I, Br, Cl, F, CF3 or C1-6alkyl and R9 is an oxy protecting group. - View Dependent Claims (3)
where three of A, B, C and D are carbon atoms and one is a nitrogen atom; R1 is where R3 and R4 are independently H, OH, protected OH, C1-8alkoxy, I, Br, Cl, F, CF3 or C1-6alkyl and R5 is —
OCH2CO2H;
R2 is where R3 and R4 are as indicated above and Z is H, OH, or C1-5alkoxy;
or a pharmaceutically acceptable salt thereof, which comprises converting a compound of formula (u), as described in claim 1, into a compound of the above Formula and thereafter optionally forming a pharmaceutically acceptable salt thereof.
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2. A compound of Formula (v):
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where R3 and R4 are independently H, OH, protected OH, C1-8alkoxy, I, Br, Cl, F,CF3 or C1-6alkyl and R9 is an oxy protecting group. - View Dependent Claims (4)
where three of A, B, C and D are carbon atoms and one is a nitrogen atom; R1 is where R3 and R4 are independently H, OH, protected OH, C1-8alkoxy, I, Br, Cl, F, CF3 or C1-6alkyl and R5 is —
OCH2CO2H;
R2 is where R3 and R4 are as indicated above and Z is H, OH, or C1-5alkoxy;
or a pharmaceutically acceptable salt thereof, which comprises converting a compound of formula (v), as described in claim 2, into a compound of the above Formula, and thereafter optionally forming a pharmaceutically acceptable salt thereof.
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Specification
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Current AssigneeSmithkline Beecham Corporation (Smithkline Beecham PLC)
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Original AssigneeSmithkline Beecham Corporation (Smithkline Beecham PLC)
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InventorsTickner, Ann Marie, Lantos, Ivan, Pridgen, Lendon Norwood, Mills, Robert John, Clark, William Morrow
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Primary Examiner(s)OWENS, AMELIA A
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Application NumberUS09/607,173Time in Patent Office621 DaysField of Search549/432, 568/630, 568/648, 568/649, 568/656US Class Current549/432CPC Class CodesC07D 317/60 Radicals substituted by car...
