Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-06-29
2002-01-15
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S272000, C514S275000, C514S303000, C514S392000, C514S393000, C514S395000, C514S398000, C514S510000, C514S569000, C514S616000, C514S621000, C514S632000, C514S634000, C540S492000, C540S553000, C544S317000, C544S332000, C546S118000, C548S307400, C548S302700, C548S321500, C560S061000, C562S461000, C564S155000, C564S169000, C564S251000
Reexamination Certificate
active
06339082
ABSTRACT:
This application is a 371 of PCT/FR98/02038 filed Sep. 20, 1998.
The present invention relates to novel tricyclic compounds, their preparation process and the intermediates of this process, their use as medicaments and the pharmaceutical compositions containing them.
A subject of the present invention is the compounds of general formula (I):
in which R
1
represents a —CONH—[A]—[B]—COR
6
group, —[A]— representing a divalent radical derived from an acyclic, linear or branched saturated or unsaturated hydrocarbon, comprising 1 to 12 carbon atoms, substituted by the (Z) group or non substituted,
[B] representing a phenyl radical, a CH(Z) radical, or a single bond,
(Z) represents a hydrogen atom, a (D)
0-6
—NRaRb, (D)
0-6
—NH—SO
2
—Rc, (D)
0-6
—NH—CO
2
—Rc, (D)
0-6
—NH—CO—Rc, (D)
0-6
—NH—SO
2
—NH—Rc, (D)
0-6
—NH—CO—NH—Rc, (D)
0-6
—CO
2
—RC, (D)
0-6
—SO
2
—Rc, (D)
0-6
—CO-Rc or (D)
0-6
—Rc group in which (D)
0-6
is a divalent radical derived from an acyclic, linear or branched, saturated or unsaturated hydrocarbon, comprising 0 to 6 carbon atoms,
Ra, Rb and Rc represent a hydrogen atom, a (CH
2
)
0-3
—Ar radical in which Ar represents a carbocyclic aryl group containing 6 to 18 carbon atoms, a (CH
2
)
0-3
—Het radical in which Het represents a radical derived from an aromatic or non aromatic, saturated or non saturated heterocycle, comprising 1 to 9 carbon atoms and 1 to 5 heteroatoms chosen from oxygen, nitrogen or sulphur atoms, a (CH
2
)
0-3
—Alk radical in which Alk represents a radical derived from a non aromatic, linear, branched or cyclic, saturated or unsaturated hydrocarbon, and comprising 1 to 12 carbon atoms, the Het, Ar and Alk radicals being able to be non substituted or substituted,
or, Ra and Rb represent together with the nitrogen atom to which they are linked a nitrogenous, aromatic or non aromatic, saturated or unsaturated heterocycle, optionally containing one or more heteroatoms chosen from oxygen, nitrogen or sulphur atoms, this radical being able to be substituted or non substituted,
R
6
represents a hydroxyl radical, an O—Alk, O—Ar, NH
2
, NH—Alk, N(Alk)
2
radical or the remainder of an L or D amino acid, Alk and Ar being as defined previously and being able to be substituted or non substituted,
R
2
and R
3
identical or different represent either a hydrogen atom, a hydroxyl radical, an O—Alk radical or an O—(CH
2
)
0-3
—Ar radical, Alk and Ar being as defined previously, or R
2
and R
3
form together a ring of the —O—(CRdRe)
n
—O— type, n being an integer from 1 to 5, Rd and Re independently of one another represent a hydrogen atom, an alkyl radical containing 1 to 6 carbon atoms, or a phenyl radical,
R
4
represents a hydrogen atom, a halogen atom, a hydroxyl, amino, nitro, cyano, CF
3
, acyl or acyloxy group containing 1 to 12 carbon atoms alkyl, alkenyl, alkynyl, alkylthio, alkoxy, alkylamino, dialkylamino, dialkylaminoalkyl, dialkylaminoalkyloxy group, in which the alkyl term contains 1 to 6 carbon atoms,
R
5
represents a hydrogen atom, a hydroxyl radical, a halogen atom, an O—Alk radical or an O—(CH
2
)
0-3
—Ar radical, Alk and Ar being as defined previously,
G represents,
either a radical of formula G1
in which Rh is a hydrogen atom or an (Alk) group as defined previously and (Het′) is a heterocycle of general formula:
in which (H) forms, with the N═C—NH— unit, the remainder of an aromatic or non aromatic, mono or bicyclic, saturated or non saturated heterocycle comprising 1 to 9 carbon atoms and 2 to 5 heteroatoms chosen from oxygen, nitrogen and sulphur atoms, this radical being able to be substituted or non substituted,
or an NRaRb radical (radical G2), Ra and Rb being as defined above,
or a (Het) radical (radical G3) as defined above,
or an —NRh—C(═X)—NHRc radical (radical G4), in which X is a sulphur, oxygen or NH atom, Rh and Rc are as defined previously,
or an —NRh—SO
2
Rc radical, (radical G5), in which Rh and Rc are as defined previously, the dotted lines represent an optional second bond, as well as the addition salts with acids, bases and esters, R
1
, R
2
and R
3
can be in position 8, 9 or 10 of the tricycle.
By compound of formula (I) is meant all the possible geometric isomers and stereoisomers taken individually or in a mixture.
When —[A]— represents a divalent radical derived from an acyclic, linear or branched, saturated or unsaturated, hydrocarbon comprising 1 to 12 carbon atoms, the alkylene radicals of formula —(CH
2
)
n
—, in which n represents an integer comprised between 1 and 12, such as —CH
2
—, —CH
2
CH
2
—, —CH
2
CH
2
CH
2
— or —CH
2
CH
2
CH
2
CH
2
—, or the alkenylene or alkynylene radicals such as —CH═CH—CH
2
— or —C═—C—CH
2
— are designated in particular.
When these divalent radicals are branched, it can be radicals such as —CH(CH
3
)—, —C(Me)
2
, —CH
2
—C(Me)
2
—, —CH(Et)—, —CH(C≡≡CH)— or —C(C≡CH)(Et)—.
When [B] represents a divalent radical —Ph—, the COR
6
group can be in ortho, meta or para position. It is preferably found in para position.
When (D)
0-6
is a divalent radical derived from an acyclic, linear or branched, saturated or unsaturated, hydrocarbon comprising 0 to 6 carbon atoms, (D)
0-6
is chosen from the values of [A] mentioned above. By (D)
0
is meant the absence of this radical which reverts to having a single covalent bond. (D) will preferably be a single bond or a (CH
2
)n group, n being an integer chosen from 1, 2 or 3 .
When Ra, Rb and Rc represent a (CH
2
)
0-3
—Ar, (CH
2
)
0-3
—Het, (CH
2
)
0-3
—Alk group, (CH
2
)
0-3
represents either a single bond in the case of (CH
2
)
0
, or —CH
2
—, —(CH
2
)
2
— or —(CH
2
)
3
— radicals.
By the term (Ar) representing a carbocyclic aryl group containing 6 to 18 carbon atoms, is meant a radical derived from an aromatic cyclic hydrocarbon such as the phenyl, naphthyl, phenanthrenyl radical or a radical derived from a condensed bicyclic or tricyclic hydrocarbon comprising a benzene ring such as indanyl, indenyl, dihydronaphtyl, tetrahydronaphtyl or fluorenyl. The junction is carried out at the level of the benzene ring. It is preferably phenyl.
By the term (Het) representing a radical derived from an aromatic or non aromatic, saturated or non saturated heterocycle, comprising 1 to 9 carbon atoms and 1 to 5 heteroatoms chosen from oxygen, nitrogen and sulphur atoms, is designated in particular:
heterocyclic monocyclic radicals, for example thienyl, furyl, pyrannyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazolyl, oxazolyl, furazannyl, pyrrolinyl, imidazolinyl, pyrazolinyl, thiazolinyl, triazolyl, tetrazolyl radicals,
heterocyclic condensed rings, for example benzofurannyl, benzothienyl, benzimidazolyl, benzothiazolyl, naphtho[2,3-b]thienyl, thianthrenyl, isobenzofurannyl, chromenyl, xanthenyl, phenoxathiinyl, indolizinyl, isoindolyl, 3H-indolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, carbazolyl, beta-carbolinyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, indolinyl, isoindolinyl, imidazopyridyl, imidazopyrimidinyl or also polycyclic condensed systems constituted by heterocyclic monocyclics as defined above such as for example furo[2,3-b]pyrrole or thieno[2,3-b]furan,
or saturated heterocycles such as pyrrolidine, piperidine, morpholine.
This term (Het) includes moreover the values of (Het′) as defined previously.
By the term (Alk) representing a radical derived from a non aromatic, linear, branched or cyclic, saturated or unsaturated hydrocarbon, is designated in the case of acyclic hydrocarbons alkyl radicals such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, 2-methyl pentyl, 2,3-dimethyl butyl, n-heptyl, 2-methylhexyl, 2,2-dimethylpentyl, 3,3-dimethyl pentyl, 3-ethylpentyl, n-octyl, 2,2-dimethylhexyl, 3,3-dimethylhexyl, 3-methyl-3-ethylpentyl, nonyl, 2,4-dimethylheptyl or n-decyl, alkenyl radicals such as vin
Carniato Denis
Gadek Thomas R.
Gourvest Jean-Francois
Knolle Jochen
McDowell Robert S.
Aventis Pharma S.A.
Bierman, Muserlian and Lucas
McKenzie Thomas C
Shah Mukund J.
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