1,2,5-trisubstituted 1,2-dihydroindazol-3-ones having anti-asthmatic, anti-allergic, anti-inflammatory, immunomodulating and neuroprotective action, process for their preparation and their use as medicaments

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United States of America Patent

PATENT NO 6180637
SERIAL NO

09305602

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Abstract

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The invention relates to 1,2,5-trisubstituted 1,2-dihydroindazol-3-ones of formula (I) ##STR1## wherein X is --SO.sub.2 --, --SO--, --(CH.sub.2).sub.p --, --(CH.sub.2).sub.p --O--, --(CH.sub.2).sub.p --(C.dbd.O)--, --(CH.sub.2).sub.p --(C.dbd.O)--NH--, --(CH.sub.2).sub.p --CHOH--, --CHOH--(CH.sub.2).sub.p --, --(CH.sub.2).sub.p --CH.dbd.CH--, --CH.dbd.CH--(CH.sub.2).sub.p --, Y is --(C.dbd.O)--, --(C.dbd.O)--NH--, --(C.dbd.O)--NH--(CH.sub.2).sub.p --, --C.dbd.O)--(CH.sub.2).sub.p --, --(CH.sub.2).sub.p --, --(CH.sub.2).sub.p --O--, --(CH.sub.2).sub.p --(C.dbd.O)--, --(CH.sub.2).sub.p --(C.dbd.O)--NH--, --(CH.sub.2).sub.p --(C.dbd.O)--NH--(CH.sub.2).sub.p --, --(CH.sub.2).sub.p --CHOH--, --CHOH--(CH.sub.2).sub.p --, --(CH.sub.2).sub.p --CH.dbd.CH--, --CH.dbd.CH--(CH.sub.2).sub.p --, Z is --O--, --O--(CH.sub.2).sub.p --, --NH--, --NH--(C.dbd.O)--, --NH--(C.dbd.O)--NH--, --NH--(C.dbd.O)--O--, --NH--CH.sub.2 --(C.dbd.O)--and --NH--(C.dbd.O)--CH.sub.2 --, P is a cardinal number from 1 to 4, R.sup.1, R.sup.2 and R.sup.3 can be the same or different and are: mono-, bi- or tricyclic saturated or mono- or polyunsaturated carbocycles having from 5 to 14 ring members; or mono-, bi- or tricyclic saturated or mono- or polyunsaturated heterocycles having from 5 to 15 ring members and from 1 to 6 heteroatoms, in which the carbocycles and the heterocycles can be mono- or polysubstituted by: C.sub.1-6 -alkyl, --O--C.sub.1-6 -alkyl, --O--C.sub.3-7 -cycloalkyl, mono-, bi- or tricyclic saturated or mono- or polyunsaturated carbocycles having from 3 to 14 ring members, mono-, bi- or tricyclic saturated or mono- or polyunsaturated heterocycles having from 5 to 15 ring members and from 1 to 6 heteroatoms, R.sup.1 is also H, provided that when X is CH.sub.2, then R.sup.1 is not H, R.sup.3 --Z is also NO.sub.2, and their pharmaceutically acceptable salts, but excluding compounds of formula (I) in which if Z is --NH--(C.dbd.O)--, --NH--(C.dbd.O)--NH--, --NH--(C.dbd.O)--O--, --NH--(C.dbd.O)--CH.sub.2 and at the same time R.sup.1 is phenyl, monosubstituted or polysubstituted by --COOH, --COOC.sub.1-6 -alkyl, --(CH.sub.2).sub.p --COOH, --(CH.sub.2).sub.p --COOC.sub.1-6 -alkyl --CONHC.sub.1-6 -alkyl, --CONHC.sub.6-14 -aryl, --CONHSO.sub.2 C.sub.1-6 -alkyl, --CONHSO.sub.2 C.sub.6-4 -aryl, 1H-tetrazol-5-yl, then R.sup.2 is not phenyl, monosubstituted or polysubstituted by CN, halogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkyloxy, CF.sub.3 ; and if R.sup.3 --Z is NO.sub.2, then R.sup.1 --X is not benzyl or 4-methoxybenzyl, and R.sup.2 --Y is not benzyl or 2-picolyl at the same time; and to pharmaceutical treatment processes, and processes for making.

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Patent Owner(s)

Patent OwnerAddress
ARZNEIMITTELWERK DRESDEN GMBHD-01435 RADEBEUL

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Inventor(s)

Inventor Name Address # of filed Patents Total Citations
Brune, Kay Marloffstein, DE 25 267
Hofgen, Norbert Medingen, DE 26 204
Poppe, Hildegard Dresden, DE 15 132
Schindler, Rudolf Dresden, DE 24 300

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