Tricyclic compounds, their preparation process and the...

Details Tricyclic compounds, their preparation process and the... Tricyclic compounds, their preparation process and the...

2001-01-25

2002-10-01

Shah, Mukund J. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C560S034000, C562S439000, C564S020000, C564S021000, C564S036000, C564S081000, C564S163000

Reexamination Certificate

active

06459001

ABSTRACT:

The present invention relates to new 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 —C≡C—[A]—[B]—COR
6
, —CH═CH—[A]—[B]—COR
6
, —(CH
2
)
2
—[A]—[B]—COR
6
, —O—[A]—[B]—COR
6
, —CH
2
CO—[A]—[B]—COR
6
group, —[A]— representing
either a bivalent hydrocarbonated radical derived from a saturated or unsaturated, linear or branched structure containing 1 to 12 carbon atoms and 1 to 6 heteroatoms chosen from oxygen, nitrogen or sulphur atoms,
or a bivalent radical derived from a saturated or unsaturated, linear or branched acyclic hydrocarbon containing 1 to 12 carbon atoms,
[B] representing a phenyl radical, a CH[Z] radical, or a single bond,
Z represents a hydrogen atom, one of the following groups:
(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 in which (D)
0-6
is a bivalent radical derived from a saturated or unsaturated, linear or branched acyclic hydrocarbon containing 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 a saturated or unsaturated, aromatic or non-aromatic heterocycle containing 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 saturated or unsaturated, linear, branched or cyclic, non-aromatic hydrocarbon, containing 1 to 12 carbon atoms, the Het, Ar and Alk radicals being able to be non-substituted or substituted, or also, Ra and Rb represent together with the nitrogen atom to which they are linked a saturated or unsaturated, aromatic or non-aromatic, nitrogenous 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 a L or D amino acid, Alk and Ar being as defined previously and being optionally substituted or not 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 with a ring of —O—(CRdRe)
n
— type, n being an integer from 1 to 5, Rd and Re independently of each other 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, one of the following groups: hydroxyl, amino, nitro, cyano, CF
3
, acyl or acyloxy containing 1 to 12 carbon atoms, alkyl, alkenyl, alkynyl, alkylthio, alkoxy, alkylamino, dialkylamino, dialkylaminoalkyl, dialkylaminoalkyloxy, in which the term alkyl 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 a saturated or unsaturated, mono- or bicyclic, aromatic or non-aromatic heterocycle containing 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 or oxygen atom or NH, 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 and bases and the 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 geometrical isomers and stereoisomers taken individually or as a mixture.
By —[A]— group representing a bivalent radical derived from a saturated or unsaturated, linear or branched structure containing 1 to 12 carbon atoms and 1 to 6 heteroatoms chosen from oxygen, nitrogen and sulphur atoms, is meant in particular, radicals derived from the alkanes some of whose carbons are replaced by oxygen or sulphur atoms, or by the following groups: C═O, SO, SO
2
, NH, N(Alk), NH—CO, N(Alk)—CO, CO—NH, CO—N(Alk), SO
2
—NH, SO
2
—N(Alk), (Alk) being as defined above. It can therefore be the following radicals:
—CH
2
—CH
2
—O—CH
2
—CH
2
—, —CH
2
—CH
2
—N(CH
3
)—CH
2
—CH
2
—, CH
2
—CH
2
—C(O)—CH
2
—CH
2
, CH
2
—C(O)—C(Me)
2
—CH
2
.
When —[A]— represents a bivalent radical derived from a saturated or unsaturated, linear or branched, acyclic hydrocarbon containing 1 to 12 carbon atoms, there are meant in particular 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 the alkenylene or alkynylene radicals such as —CH═CH—CH
2
— or —C═C—CH
2
—.
When these bivalent radicals are branched, they 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 —Ph— bivalent radical, the COR
6
group can be in ortho, meta or para position. It is preferably found in the para position.
When (D)
0-6
is a bivalent radical derived from a saturated or unsaturated, linear or branched, acyclic hydrocarbon containing 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 once again has 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 the radical —CH
2
—, —(CH
2
)
2
— or —(CH
2
)
3
—.
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 containing a benzene ring such as indanyl, indenyl, dihydronaphthyl, tetrahydronaphthyl or fluorenyl. The junction occurs at the level of the benzene ring. It is preferably the phenyl.
By the term (Het) representing a radical derived from a saturated or unsaturated, aromatic or non-aromatic heterocycle containing 1 to 9 carbon atoms and 1 to 5 heteroatoms chosen from oxygen, nitrogen and sulphur atoms, is meant in particular:
monocyclic heterocyclic radicals, for example the following radicals: thienyl, furyl, pyrannyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazolyl, oxazolyl, furazannyl, pyrrolinyl, imidazolinyl, pyrazolinyl, thiazolinyl, triazolyl, tetrazolyl,
condensed heterocyclic 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

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