1. A method for producing a set of cooperating embossing rollers, characterized in that for parameterising the embossing rollers a modelling device is used comprising a pair of rollers, which are put under measurable and adjustable pressure in order to determine the parameters for producing the embossing rollers from the measurement data.
2. The method according to claim 1, characterized in that the rollers of the modelling device are put under external and hydraulic pressure and the deflection of one of the rollers is measured in order to determine from this the geometrical shape of the surface of the backup-roller in the embossing roller set,
3. The method according to claim 2, characterized in that the modelling device comprises two rollers with a shell and an axle each, which on both ends are mounted in a mounting in a housing and are put under hydrostatic pressure, while an external pressure is created on one of the rollers, the effect of which on the roller axle is measured,
4. The method according to claim 1, characterized in that the model device comprises elements in order to measure the course of the deflection of an axle from the force externally applied on a roller.
5. The method according to claim 4, characterized in that the measurement data are used in order to determine the geometry of the surface of the backup-roller of the embossing roller set,
6. The method according to claim 4, characterized in that the geometrical shape of the surface of the backup-roller is a crown that is selected slightly larger than the deflection of the embossing roller through the external pressure.
7. A modelling device for carrying out the method according to claim 1, for determining the parameters for producing a set of embossing rollers, characterized in that the modelling device comprises two rollers, wherein each roller comprises an axle which is hydrostatically mounted in a shell in two bearing regions and means in order to create an adjustable and measurable counter-pressure to the external pressure on the axle.
8. The device according to claim 7, characterized in that the means are recesses on the axle which are connected to a hydraulic oil line, in order to create a hydrostatic pressure.
9. The device according to claim 8, characterized in that the axle comprises at least one sectorial recess serving as pressure pocket and is held on both sides in the shell in a bearing region, wherein the axle in the bearing region comprises symmetrically arranged recesses serving as bearing pockets in order to form a hydrostatic bearing each and both the pressure pocket as well as the bearing pockets are connected to the oil line.
10. The device according to claim 7, characterized in that it comprises an adjusting and evaluation unit in order to adjust the hydraulic pressure with a given external pressure and from the measurement results calculate the geometrical shape of the surface of the backup-roller.
The claims below are in addition to those above.
All refrences to claims which appear below refer to the numbering after this setence.
1. Compounds derived from substituted 3-phenyl-1-(phenylthienyl)propan-1-ones and 3-phenyl-1-(phenylfuranyl)propan-1-ones of general formula (I):
in which:
X1 represents a halogen, a R1, \u2014SR1 or \u2014OR1 group;
X2 represents a sulfur or oxygen atom;
X3 represents a halogen, a R3, \u2014SR3 or \u2014OR3 group;
X4 represents a halogen, a R4, \u2014SR4 or \u2014OR4 group;
X5 represents a R5, \u2014SR5 or \u2014OR5 group;
X6 represents a halogen, a R6, \u2014SR6 or \u2014OR6 group;
X7 represents a halogen, a R7, \u2014SR7 or \u2014OR7 group;
X8 represents a R8 group;
R1 representing a hydrogen or an alkyl group having 1 to 4 carbon atoms, said alkyl group being optionally halogenated;
R3, R4, R6, R7 and R8, which may be identical or different, selected from hydrogen or an alkyl group having 1 to 4 carbon atoms;
R5 representing an alkyl radical formed from a saturated linear carbon chain, having 1 to 4 carbon atoms, said carbon chain being:
bound, by its end opposite to the phenyl group (III), to a substituent selected from \u2014COOR12 and \u2014CONR12R13, R12 and R13, which may be identical or different, representing a hydrogen or an alkyl group having 1 to 4 carbon atoms;
unbranched or branched with at least one alkyl or alkenyl group having 1 to 4 carbon atoms, or substituted with a phenyl group;
A represents:
(i) a carbonyl group (CO),
(ii) an oxime group (C\u2550N\u2014O\u2014H) or oxime ether group (C\u2550N\u2014O\u2014R11), with R11 selected from a hydrogen atom, an alkyl group (linear or branched) having 1 to 7 carbon atoms, substituted or not with an aryl group, notably a phenyl group, said alkyl and aryl groups being optionally halogenated, or
(iii) a \u2014CR9R10 group, R9 representing a hydrogen atom and R10 representing an \u2014OR11 group, R11 being selected from a hydrogen atom or an alkyl group (linear or branched) having 1 to 7 carbon atoms, said alkyl group being unsubstituted or substituted with a cycloalkyl group, notably cyclohexyl, an aryl group, notably phenyl or a heteroaryl group, notably pyridinyl, said alkyl, cycloalkyl, aryl or heteroaryl groups being optionally halogenated;
B represents:
(i) an unsubstituted, saturated alkyl group having two carbon atoms (CH2\u2014CH2), or
(ii) an unsubstituted alkene group, having two carbon atoms (CH\u2550CH),
their stereoisomers (diastereoisomers, enantiomers), pure or mixed, racemic mixtures, geometric isomers, tautomers, salts, hydrates, solvates, solid forms and mixtures thereof.
2. The compounds according to claim 1, characterized in that X5 represents an \u2014OR5 group, with R5 representing an alkyl radical whose said carbon chain is bound to a \u2014COOR12 substituent.
3. The compounds according to claim 1, characterized in that X5 is selected from the groups: \u2014OC(CH3)2COOR12, \u2014OCH(CH2CH3)COOR12, \u2014O(CH2)3C(CH3)2COOR12, \u2014OCH(C6H5)COOR12 and \u2014OCH2COOR12.
4. The compound according to claim 1, characterized in that A represents a carbonyl group C\u2550O.
5. The compound according to claim 1, characterized in that A represents a \u2014CHOR11 group, with R11 selected from a hydrogen atom, a methyl, ethyl, isopropyl, cyclohexylmethyl, benzyl, iodobenzyl and pyridinylmethyl group.
6. The compounds according to claim 1, characterized in that A represents a C\u2550N\u2014O\u2014R11 group, with R11 selected from a hydrogen atom and a methyl group.
7. The compounds according to claim 1, characterized in that ring II is substituted with ring I in position C4.
8. The compounds according to claim 1, characterized in that ring II is substituted with ring I in position C5.
9. The compounds according to claim 1, characterized in that X1 is in the para position relative to the position of ring II.
10. The compounds according to claim 1, characterized in that X1 is selected from a trifluoromethyl group, a bromine atom, a methyloxy group, a methylthio group and a trifluoromethoxy group and a hydrogen atom.
11. The compounds according to claim 1, characterized in that at least one of the groups X3, X4, X6 and X7 represents a halogen atom.
12. The compounds according to claim 1, characterized in that X3 and X4 are identical and correspond to halogen atoms.
13. The compounds according to claim 1, characterized in that X3 and X4 are identical and correspond to chlorine or fluorine atoms.
14. The compounds according to claim 1, characterized in that at least one of the groups X3, X4, X6 and X7 represents a halogen atom, and the remaining group(s) among X3, X4, X6 and X7 represents a hydrogen atom or hydrogen atoms.
15. The compounds according to claim 1, characterized in that X4 andor X6 represents an alkyl group.
16. The compounds according to claim 1, characterized in that X4 and X6 are two methyl groups, and X3, X7 are hydrogen atoms.
17. The compounds according to claim 1, characterized in that they are selected from:
tert-butyl2-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-2-methylpropanoate;
2-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)-2-methylpropanoic acid;
tert-butyl 2-(2,3-dichloro-4-(3-hydroxy-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)-2-methylpropanoate;
2-(2,3-dichloro-4-(3-hydroxy-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
tert-butyl 2-(4-(3-(4-iodobenzyloxy)-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)-2,3-dichlorophenoxy)-2-methylpropanoate;
2-(4-(3-(4-iodobenzyloxy)-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)-2,3-dichlorophenoxy)-2-methylpropanoic acid;
2-(4-(3-(benzyloxy)-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-2,3-dichlorophenoxy)-2-methylpropanoic acid;
tert-butyl 2-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)butanoate;
2-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)butanoic acid;
tert-butyl 2-(2,3-dichloro-4-(3-oxo-3-(4-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-2-methylpropanoate;
2-(2,3-dichloro-4-(3-oxo-3-(4-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)-2-methylpropanoic acid;
methyl 5-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-2,2-dimethylpentanoate;
5-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)phenoxy)-2,2-dimethylpentanoic acid;
tert-butyl 2-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)acetate;
2-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)acetic acid;
ethyl 2-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-2-phenylacetate;
2-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)-2-phenylacetic acid;
tert-butyl 2-(2-chloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-2-methylpropanoate;
2-(2-chloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)-2-methylpropanoic acid;
tert-butyl 2-(3-chloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-2-methylpropanoate;
2-(3-chloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)-2-methylpropanoic acid;
tert-butyl 2-(2-fluoro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-2-methylpropanoate;
2-(2-fluoro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-2-methylpropanoic acid;
tert-butyl 2-(2-fluoro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)acetate;
2-(2-fluoro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)acetic acid;
2-(2-fluoro-4-(3-hydroxy-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)acetic acid;
2-(4-(3-(benzyloxy)-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-2-fluorophenoxy)acetic acid;
tert-butyl 2-(2-fluoro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)butanoate;
2-(2-fluoro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)butanoic acid;
2-(2-fluoro-4-(3-hydroxy-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)butanoic acid;
tert-butyl 2-(2-bromo-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)butanoate;
2-(2-bromo-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)butanoic acid;
tert-butyl 2-(2-bromo-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)acetate;
2-(2-bromo-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)acetic acid;
tert-butyl 2-(2-bromo-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-2-methylpropanoate;
2-(2-bromo-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)-2-methylpropanoic acid;
tert-butyl 2-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)fur-2-yl)propyl)-phenoxy)-2-methylpropanoate;
2-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)fur-2-yl)-propyl)phenoxy)-2-methylpropanoic acid;
2-(2,3-dichloro-4-(3-(pyridin-3-ylmethoxy)-3-(5-(4-(trifluoromethyl)-phenyl)thien-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
2-(2,3-dichloro-4-(3-methoxy-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
2-(2,3-dichloro-4-(3-ethoxy-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
2-(2,3-dichloro-4-(3-(cyclohexylmethoxy)-3-(5-(4-(trifluoromethyl)-phenyl)thien-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
tert-butyl 2-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethoxy)phenyl)thien-2-yl)-propyl)phenoxy)-2-methylpropanoate;
2-(2,3-dichloro-4-(3-oxo-3-(5-(4-(trifluoromethoxy)phenyl)thien-2-yl)-propyl)phenoxy)-2-methylpropanoate acid;
tert-butyl 2-(2,3-difluoro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-2-methylpropanoate;
2-(2,3-difluoro-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)-2-methylpropanoic acid;
tert-butyl 2-(2,6-dimethyl-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-2-methylpropanoate;
2-(2,6-dimethyl-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)-2-methylpropanoic acid;
2-(2,3-dichloro-4-(3-(hydroxyimino)-3-(5-(4-(trifluoromethyl)phenyl)-thien-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
2-(2,3-dichloro-4-(3-(methoxyimino)-3-(5-(4-(trifluoromethyl)phenyl)-thien-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
tert-butyl 2-(4-(3-(5-(4-bromophenyl)thien-2-yl)-3-oxopropyl)-2,3-dichlorophenoxy)-2-methylpropanoate;
2-(4-(3-(5-(4-bromophenyl)thien-2-yl)-3-oxopropyl)-2,3-dichloro-phenoxy)-2-methylpropanoic acid;
tert-butyl 2-(2,3-dichloro-4-(3-(5-(4-(methylthio)phenyl)thien-2-yl)-3-oxopropyl)-phenoxy)-2-methylpropanoate;
2-(2,3-dichloro-4-(3-(5-(4-(methylthio)phenyl)thien-2-yl)-3-oxo-propyl)phenoxy)-2-methylpropanoic acid;
2-(2,3-dichloro-4-(3-isopropoxy-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
tert-butyl 2-(2,3-dichloro-4-(3-oxo-3-(5-phenylthiophen-2-yl)propyl)phenoxy)-2-methylpropanoate;
2-(2,3-dichloro-4-(3-oxo-3-(5-phenylthien-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
tert-butyl 2-methyl-2-(2-methyl-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thiophen-2-yl)propyl)phenoxy) propanoate;
2-methyl-2-(2-methyl-4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)-thiophen-2-yl)propyl)phenoxy)propanoic acid;
2-(2,3-dichloro-4-(3-hydroxy-3-(4-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
2-(4-(3-(benzyloxy)-3-(4-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-2,3-dichlorophenoxy)-2-methylpropanoic acid;
2-(2,3-difluoro-4-(3-hydroxy-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
2-(4-(3-(benzyloxy)-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-2,3-difluorophenoxy)-2-methylpropanoic acid;
tert-butyl 2-(4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)phenoxy)-butanoate;
2-(4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-butanoic acid;
tert-butyl 2-methyl-2-(4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)propanoate;
2-(4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-2-methylpropanoic acid;
tert-butyl 2-(4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)phenoxy)-acetate;
2-(4-(3-oxo-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)acetic acid;
2-(4-(3-(benzyloxy)-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-2-fluorophenoxy)butanoic acid;
2-(2,3-dichloro-4-(3-hydroxy-3-(5-(4-(trifluoromethyl)phenyl)furan-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
2-(2,3-dichloro-4-(3-methoxy-3-(5-(4-(trifluoromethyl)phenyl)fur-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
2-(4-(3-hydroxy-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-2,6-dimethylphenoxy)-2-methylpropanoic acid;
2-(4-(3-methoxy-3-(5-(4-(trifluoromethyl)phenyl)thien-2-yl)propyl)-2,6-dimethylphenoxy)-2-methylpropanoic acid;
ethyl 2-(2,3-dichloro-4-(3-oxo-3-(5-(3-(trifluoromethyl)phenyl)thien-2-yl)propyl)-phenoxy)-2-methylpropanoate;
2-(2,3-dichloro-4-(3-oxo-3-(5-(3-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)-2-methylpropanoic acid;
ethyl 2-(2,3-dichloro-4-(3-hydroxy-3-(5-(3-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)-2-methylpropanoate;
ethyl 2-(2,3-dichloro-4-(3-methoxy-3-(5-(3-(trifluoromethyl)phenyl)thien-2-yl)-propyl)phenoxy)-2-methylpropanoate;
2-(2,3-dichloro-4-(3-hydroxy-3-(5-(4-(trifluoromethoxy)phenyl)thien-2-yl)propyl)phenoxy)-2-methylpropanoic acid;
2-(2,3-dichloro-4-(3-methoxy-3-(5-(4-(trifluoromethoxy)phenyl)thien-2-yl)propyl)phenoxy)-2-methylpropanoic acid.
18. The compounds according to claim 1, as medicinal products.
19. A pharmaceutical composition comprising, in a pharmaceutically acceptable carrier, at least one compound as defined in claim 1, optionally in combination with one or more other therapeutic andor cosmetic active principles.
20. A pharmaceutical composition comprising, in a pharmaceutically acceptable carrier, at least one compound as defined in claim 1, in combination with one or more compounds selected from the following list:
an antidiabetic,
insulin,
an antilipemic andor cholesterol-lowering molecule,
an antihypertensive or hypotensive agent,
an antiplatelet agent,
an antiobesity agent,
an antiinflammatory agent,
an antioxidant,
an agent used in the treatment of heart failure,
an agent used for the treatment of coronary insufficiency,
an anticancer agent,
an antiasthmatic,
a corticoid used in the treatment of skin diseases
a vasodilator andor an antiischemic agent.
21. The pharmaceutical composition according to claim 19, for treating the complications associated with metabolic syndrome, insulin resistance, dyslipidemias, atherosclerosis, cardiovascular diseases, obesity, hypertension, inflammatory diseases, cerebral ischemia, autoimmune diseases, neurodegenerative pathologies or cancers.
22. The pharmaceutical composition according to claim 19, for treating the cardiovascular risk factors connected with disturbances of lipid andor carbohydrate metabolism.
23. The pharmaceutical composition according to claim 19, for the treatment of diabetes.
24. The pharmaceutical composition according to claim 19, for the treatment of dyslipidemias.