1. Process for preparing pyridyl-substituted pyrazole derivatives of the general formula (I)
in which
R1 is alkoxy, hydroxyl, aryloxy, alkylaryloxy, alkyl, cycloalkyl, halogen,
R2 is hydroxyl, alkoxy, arylalkoxy, allylthio, chlorine, bromine, fluorine, iodine, O\u2014(C\u2550O)alkyl, O\u2014(C\u2550O)O-alkyl, OSO2alkyl, OSO2Ph, OSO2-haloalkyl, OSO2-aryl,
characterized in that
(A) acetyleneketones of the formula (II)
in which
R4 is a protecting group selected from (C1-C6)-alkyl, aryl, benzyl, tetrahydropyran, (C\u2550O)-alkyl, (C\u2550O)\u2014Oalkyl, Si(alkyl)3,
and X is halogen
are reacted with hydrazinopyridines of the formula (III)
in which
R3 is halogen, CN, NO2, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkylamino,
to give 1-pyridyl-substituted dihydro-1H-pyrazoles of the formula (IV)
in which X, R3, R4 are each as defined above,
(B) the latter are optionally converted further, without preceding isolation, with elimination of water, to 1-pyridyl-substituted trihalomethylpyrazoles of the formula (V)
in which X, R3, R4 are each as defined above,
(C) these compounds of the general formula (V)
are converted with addition of H2SO4, for example, to pyrazolecarboxylic acids of the formula (VI)
in which R3, R4 are each as defined above,
(D) the latter are converted, after detaching the protecting group R4, to hydroxymethylpyrazole acids of the formula (VII)
in which R3 is as defined above, and
(E) the latter are converted to compounds of the formula (I).
2. Process for preparing compounds of the formula (I) according to claim 1, characterized in that
R1 is (C1-C6)-alkoxy, halogen,
R2 is (C1-C6)-alkoxy, aryl(C1-C6)-alkoxy, fluorine, chlorine, bromine, iodine,
R3 is halogen, CN, NO2, (C1-C6)-alkyl, halo(C1-C6)-alkyl, (C1-C6)-alkoxy, halo(C1-C6)alkoxy.
3. Process for preparing compounds of the formula (I), characterized in that the preparation of the compound of the formula (V) comprises steps (A) and (B) according to claim 1.
4. Process for preparing compounds of the formula (I) according to claim 3, characterized in that the compounds of the formula (V)
in which
X is halogen,
R4 is a protecting group selected from (C1-C6)-alkyl, aryl, benzyl, tetrahydropyran, (C\u2550O)-alkyl, (C\u2550O)\u2014Oalkyl, Si(alkyl)3,
R3 is halogen, CN, NO2, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkylamino,
are converted by detaching the protecting group to compounds of the formula (VIII)
in which
X, R3 are each as defined above,
the latter are converted by hydrolysis to compounds of the general formula (VII)
in which
R3 is as defined above,
and the latter are converted with addition of a halogenating agent and subsequent alcohol addition to compounds of the formula (I).
5. Process for preparing compounds of the formula (I) according to claim 3,
characterized in that the compounds of the formula (V)
in which
X is halogen,
R4 is a protecting group selected from (C1-C6)-alkyl, aryl, benzyl, tetrahydropyran, (C\u2550O)-alkyl, (C\u2550O)\u2014Oalkyl, Si(alkyl)3,
R3 is halogen, CN, NO2, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkylamino,
are converted with addition of alcohol directly to the inventive compounds of the formula (I).
6. Compounds of the formula (I) according to claim 1, characterized in that
R1 is halogen,
R2 is fluorine, chlorine, bromine, iodine,
R3 is halogen, CN, NO2, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkylamino.
7. Compounds of the formula (IV) according to claim 1, characterized in that
X is halogen,
R3 is chlorine,
R4 is benzyl.
8. Compounds of the formula (V) according to any of claims 1 to 5, characterized in that
X is halogen,
R3 is chlorine,
R4 is benzyl.
9. Compounds of the formula (V) according to claim 8, characterized in that
X is chlorine.
10. Compounds of the formula (VII) according to claim 1 or 4, characterized in that
R3 is halogen, CN, NO2, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkylamino.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. Method for controlling and regulating a motor driven adjusting device, more particularly a window lifter, seat adjuster or a sun-roof, of a motor vehicle with an anti-jamming protection, wherein input variables of the motorised drive are continuously detected and the actual load of the adjusting device or motorised drive is determined through systems of equations which were set up using a mathematical model of the complete adjusting device including the drive, and on exceeding a predetermined load limit the motorised drive is switched off or regulated to a value below the load limit, characterised in that
the continuously detected input variables are converted into individual force components (Fmot, FBeschl, Fres, Fsh) which contribute to increasing or reducing the overall load (FEinkl) of the adjusting device or individual components of the adjusting device and which are entered with a positive sign into the calculation of the actual total load (FEinkl) of the adjusting device or drive, which depends on whether the relevant force component (Fmot, FBeschl, Fres, Fsh) assists the adjusting movement of the adjusting device or drive or counteracts the adjusting movement of the adjusting device or drive.
2. Method according to claim 1, characterised in that as an input variable the speed (n) of a drive formed as an electric motor is sent both to a third dynamic system of equations (3) formed as a high pass filter, which takes into account a mechanical time constant and slide friction constant, and also together with a control signal (AS) of the electric motor as an input variable to a static system of equations (6) and that the force component (Fres) issued by the third dynamic equation system (3) with negative sign and the motor force component (Fmot) issued by the static equation system (6) with positive sign are supplied to a comparison member (5).
3. Method according to claim 2, characterised in that the comparison member (5) is connected to a high pass filter (7) which issues the maximum jamming force (Feinkl) permissible.
4. Method according to claim 2, characterised in that an input variable (P) corresponding to the position of the device to be adjusted is entered into a dynamic system of equations (4) containing a table function and which issues a position-dependent adhesive friction force component (FSH) with negative sign to the comparison member (5) from which the maximum permissible jamming force (FEinkl) is issued.
5. Method according to claim 1, characterised in that as an input variable the speed (n) of a drive formed as an electric motor is sent both to a third dynamic system of equations (3) formed as a high pass filter, which takes into account a mechanical time constant and slide friction constant, and also together with a control signal (AS) of the electric motor as an input variable to a second dynamic system of equations (2), that the force component (Fres) issued by the third dynamic equation system (3) with negative sign and the motor force component (Fmot) issued by the second dynamic equation system (2) with positive sign are supplied to a comparison member (5), that an input variable (P) corresponding to the position of the device to be adjusted is entered into a fourth dynamic system of equations (4) containing a table function and which issues a position-dependent adhesive friction force component (FSH) with negative sign to the comparison member (5) from which the maximum permissible jamming force (FEinkl) is issued.
6. Method according to claim 5 characterised in that an input variable (BV) detecting the vertical acceleration of the window pane is supplied to a first dynamic system of equations (1) which takes into account the mass to be adjusted and which issues an acceleration force component FBeschl with negative sign to the comparison member (5).
7. Method according to one of the preceding claims characterised in that at least a part of the parameters of the mathematical model is determined on the basis of the input variables actually detected or the time-dependent paths of the input variables.
8. Method according to one of the preceding claims, characterised in that at least a part of the parameters of the mathematical model is established on the basis of empirically determined data.
9. Method according to one of the preceding claims characterised in that empirically determined data or theoretical load calculations regarding the mechanical components of the drive are used when establishing the load limit.
10. Method according to one of the preceding claims characterised in that the load limit is determined in dependence on the temperature of at least one part of the adjusting device.
11. Method according to claim 10 characterised in that the load limit is determined anew for each adjusting process.
12. Method according to claim 10 characterised in that the load limit is determined continuously during an adjusting process.
13. Method according to one of the preceding claims characterised in that when establishing the load limit the mean variation of the actual load generated by the motorised drive and calculated through the mathematical model is taken into account reducing the amount.
14. Method according to one of the preceding claims characterised in that the mathematical model has a dynamic part which takes into account the influences during acceleration and braking of the drive.
15. Method according to one of the preceding claims characterised in that the mathematical model has a proportion which represents the actual characteristic field of the drive used.