Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-03-02
2002-11-12
Shah, Mukund (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S210180, C514S210190, C514S210200, C514S210210, C544S060000, C544S111000, C544S242000, C544S359000, C546S139000, C546S150000, C546S176000, C546S268100, C546S268400, C548S152000, C548S202000, C548S217000, C548S364100, C548S518000, C548S950000
Reexamination Certificate
active
06479479
ABSTRACT:
The present invention relates to derivatives of formula:
their salts, their preparation and the medicaments containing them.
In formula (I),
R represents a radical CR
1
R
2
, C═C(R
5
)SO
2
R
6
or C═C(R
7
)SO
2
alk,
or R
1
represents a hydrogen atom and R
2
represents a radical —C(R
8
) (R
9
) (R
10
), —C(R
8
) (R
11
) (R
12
), —CO—NR
13
R
14
, —CH
2
—CO—NR
13
R
14
, —CH
2
—CO—R
6
, —CO—R
6
, —CO-cycloalkyl, —SO—R
6
, —SO
2
—R
6
, —C(OH) (R
12
) (R
6
), —C(OH) (R
6
) (alkyl), —C(═NOalk)R
6
, —C(═NO—CH
2
—CH═CH
2
)R
6
, —CH
2
—CH(R
6
)NR
31
R
32
, —CH
2
—C(═NOalk)R
6
, —CH(R
6
)NR
31
R
32
, —CH(R
6
)NHSO
2
alk, —CH(RP
6
)NHCONHalk or —CH(R
6
)NHCOalk,
or R
1
represents an alkyl, NH—R
15
, cyano, —S—alk—NR
16
R
17
, —CH
2
—NR
18
R
19
, or —NR
20
R
21
radical and R
2
represents a radical —C(R
8
) (R
11
) (R
12
),
R
3
and R
4
, which are identical or different, represent either an alkyl or cycloalkyl radical, or an aromatic chosen from phenyl, naphthyl or indenyl, these aromatics being unsubstituted or substituted with one or more halogen atoms or alkyl, alkoxy, formyl, hydroxyl, trifluoromethyl, trifluoromethoxy, —CO—alk, cyano, —COOH, —COOalk, —CONR
22
R
23
, —CO—NH—NR
24
R
25
, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkylsulfanylalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, hydroxyalkyl or -alk—NR
24
R
25
radicals; or a heteroaromatic chosen from the benzofuryl, benzothiazolyl, benzothienyl, benzoxazolyl, chromanyl, 2,3-dihydrobenzofuryl, 2,3-dihydrobenzothienyl, furyl, imidazolyl, isochromanyl, isoquinolyl, pyrrolyl, pyridyl, pyrimidinyl, quinolyl, 1,2,3,4-tetrahydroisoquinolyl, thiazolyl and thienyl rings, it being possible for these heteroaromatics to be unsubstituted or substituted with one or more halogen atoms or alkyl, alkoxy, hydroxyl, trifluoromethyl, trifluoromethoxy, cyano, —COOH, —COOalk, —CO—NH—NR
24
R
25
, —CONR
22
R
23
, -alk—NR
24
R
25
, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkylsulfanylalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl or hydroxyalkyl radicals,
R
5
represents a hydrogen atom or an alkyl radical,
R
6
represents a radical Ar or Het,
R
7
represents a cycloalkyl, heterocycloalkyl or heterocyclenyl radical optionally substituted by a —CSO-phenyl radical,
R
8
represents a hydrogen atom or an alkyl radical,
R
9
represents a radical —CO—NR
26
R
27
, —COOH, —COOalk, —CH
2
QH, —NH—CO—NH—alk, —CH
2
—NHR
28
or —NHCOOalk,
R
10
represents a radical Ar or Het,
R
11
represents a radical —SO
2
—alk, —SO
2
—Ar or —SO
2
—Het,
R
12
represents a hydrogen atom or a radical Ar or Het,
R
13
represents a hydrogen atom or an alkyl radical,
R
14
represents a radical Ar, Het, -alk—Ar or -alk-Het,
R
15
represents an alkyl, cycloalkyl or -alk—NR
29
R
30
radical,
R
16
and R
17
, which are identical or different, represent a hydrogen atom or an alkyl radical or alternatively R
16
and R
17
together form with the nitrogen atom to which they are attached a 3- to 10-membered unsaturated or saturated mono- or bicyclic heterocycle optionally containing one or more other heteroatoms chosen from oxygen, sulfur and nitrogen and optionally substituted with one or more alkyl radicals,
R
18
represents a hydrogen atom or an alkyl radical,
R
19
represents a hydrogen atom or an alkyl, cycloalkyl, cycloalkylalkyl, cycloalkylcarbonyl, —SO
2
alk, —CO—NHalk or —COOalk radical,
or alternatively R
18
and R
19
form with the nitrogen atom to which they are attached a 3- to 10-membered unsaturated or saturated mono- or bicyclic heterocycle optionally containing one or more heteroatoms chosen from oxygen, sulfur and nitrogen and optionally substituted with one or more alkyl radicals,
—NR
20
R
2
, represents a 3- to 8-membered saturated or unsaturated monocyclic heterocycle optionally containing another heteroatom chosen from oxygen, nitrogen and sulfur,
R
22
and R
23
, which are identical or different, represent a hydrogen atom or an alkyl radical or alternatively R
22
and R
23
together form with the nitrogen atom to which they are attached a 3- to 10-membered saturated mono- or bicyclic heterocycle optionally containing another heteroatom chosen from oxygen, sulfur and nitrogen and being optionally substituted with one or more alkyl radicals,
R
24
and R
25
, which are identical or different, represent a hydrogen atom or an alkyl, —COOalk, cycloalkyl, alkylcycloalkyl, -alk—O—alk or hydroxyalkyl radical or alternatively R
24
and R
25
together form with the nitrogen atom to which they are attached a 3- to 10-membered saturated or unsaturated mono- or bicyclic heterocycle, optionally containing another heteroatom chosen from oxygen, sulfur and nitrogen and being optionally substituted with one or more alkyl, —COalk, —COOalk, —CO—NHalk, —CS—NHalk, oxo, hydroxyalkyl, -alk—O—alk or —CO—NH
2
radicals,
R
26
and R
27
, which are identical or different, represent a hydrogen atom or an alkyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, -alk—COOalk, -alk—Ar, -alk-Het, Het or -alk—N(alk)
2
radical, R
26
and R
27
may also form with the nitrogen atom to which they are attached a 3- to 10-membered unsaturated or saturated mono- or bicyclic heterocycle optionally containing one or more other heteroatoms chosen from oxygen, sulfur and nitrogen and optionally substituted with one or more alkyl or alkoxy radicals or halogen atoms,
R
28
represents a —CH
2
—alk, benzyl, —SO
2
alk, —CONHalk, —COalk, cycloalkylalkylcarbonyl, cycloalkylcarbonyl or —CO—(CH
2
)
n
OH radical,
n is equal to 1, 2 or 3,
R
29
and R
30
, which are identical or different, represent a hydrogen atom or an alkyl radical or alternatively R
29
and R
30
together form with the nitrogen atom to which they are attached a 3- to 10-membered saturated mono- or bicyclic heterocycle optionally containing another heteroatom chosen from oxygen, sulfur and nitrogen and being optionally substituted with one or more alkyl radicals,
R
31
and R
32
, which are identical or different, represent a hydrogen atom or an alkyl, Ar or -alk-Ar radical or alternatively R
31
and R
32
together form with the nitrogen atom to which they are attached a heterocycle chosen from aziridinyl, azetidinyl, pyrrolidinyl and piperidinyl,
alk represents an alkyl or alkylene radical,
Ar represents a phenyl or naphthyl radical optionally substituted with one or more substituents chosen from a halogen atom or an alkyl, alkoxy, —CO—alk, cyano, —COOH, —COOalk, —CONR
22
R
23
, —CO—NH—NR
24
R
25
, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkylsulfanylalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, hydroxyalkyl, -alk—NR
24
R
25
, —NR
24
R
25
, alkylthioalkyl, formyl, hydroxyl, CF
3
, OCF
3
, Het, —O—alk—NH—cycloalkyl or SO
2
NH
2
radical,
Het represents a 3- to 10-membered unsaturated or saturated mono- or bicyclic heterocycle containing one or more heteroatoms chosen from oxygen, sulfur and nitrogen and optionally substituted with one or more halogen atoms or alkyl, alkoxy, alkoxycarbonyl, —CONR
22
R
23
, hydroxyl, hydroxyalkyl, oxo or SO
2
NH
2
radicals.
In the preceding definitions and in those which follow, unless otherwise stated, the alkyl and alkylene radicals and portions and the alkoxy radicals and portions are in the form of a straight or branched chain and contain 1 to 6 carbon atoms, the cycloalkyl radicals contain 3 to 10 carbon atoms and the heterocycloalkyl and heterocyclenyl radicals contain 3 to 10 carbon atoms.
Among the alkyl radicals, there may be mentioned the methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl and hexyl radicals. Among the alkoxy radicals, there may be mentioned the methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy and pentyloxy radicals.
Among the cycloalkyl radicals, there may be mentioned the cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl radicals.
The heterocycloalkyl radicals are cycloalkyl radicals in which at least one of the carbon atoms is replaced with a heteroatom chosen from nitrogen, sulfur and oxygen. Among these, there may be mentioned the pyrrolidinyl, imidazolidinyl, pyrazolidinyl, pi
Achard Daniel
Bouchard Herve
Bouquerel Jean
Filoche Bruno
Grisoni Serge
Aventis Pharma S.A.
McKenzie Thomas
Newman Irvine
Shah Mukund
LandOfFree
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