1. A process for preparing a pyrrole derivative of the formula I
wherein
R1 is hydrogen or a straight or branched, saturated or unsaturated C1-30 hydrocarbon group which may comprise 1-5 oxygen atoms, 1-5 nitrogen atoms, 1-2 sulfur atoms, 1 selenium atom andor 1-5 \u2014NR6\u2014 residues, which hydrocarbon group may be substituted with 1-5 optionally protected hydroxy groups, 1-5 \u2014OR7 residues, 1-5 \u2014NR8R9 residues, 1-5 halogen atoms andor 1-5 optionally protected carboxy groups, in which hydrocarbon group 1-5 carbon atoms may form carbonyl groups and which hydrocarbon group or part of which hydrocarbon group may form one or more rings,
R2 is \u2014OR3, \u2014NR4R5, \u2014NR10CONR11R12, \u2014NR13OR14, \u2014ONR15R16 or halogen,
R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15 and R16 are independently selected from hydrogen or a straight, branched andor cyclic, saturated or unsaturated C1-10 alkyl residue or aryl residue, both residues being optionally substituted with 1-3 optionally protected hydroxy or carboxy groups, 1-3 \u2014OR7 residues, 1-3 \u2014NR8R9 residues andor 1-3 halogen atoms, the C1-10 alkyl residue optionally comprising 1-3 oxygen atoms, 1-3 nitrogen atoms andor 1-3 \u2014NR6\u2014 residues, the C1-10 alkyl residue further optionally comprising or being substituted with 1 or 2 aryl residues,
or a salt thereof,
which process comprises the steps of reacting a compound of the formula II
wherein R2 is defined as above, or a salt thereof, with a compound of the formulae IIIa, IIIb or IIIc
R1\u2014NH2\u2003\u2003IIIa,
R1\u2014NH\u2014COO\u2212H3N+\u2014R1\u2003\u2003IIIb
R1\u2014NH\u2014SiR17R18R19\u2003\u2003IIIc,
or mixtures thereof, wherein R1 is defined as above,
R17 and R18 are independently selected from straight, branched andor cyclic C1-10 alkyl residue or aryl residue; and
R19 is straight, branched andor cyclic C1-10 alkyl residue, aryl residue or \u2014NH\u2014R1,
and, if necessary, converting the obtained pyrrole derivative having the substituent R1 into a pyrrole derivative having a different substituent R1,
provided that if R2 is \u2014NR4R5 the compound of the formula IIIa is NH3.
2. The process according to claim 1, wherein R2 is \u2014OR3 or halogen.
3. The process according to claim 2, which comprises the additional step of separating the pyrrole derivative of the formula I from the reaction by-product of the formula IV
wherein R1 at both occurrences are identical and defined as in claim 1.
4. The process according to claim 3, which comprises the additional step of converting the separated reaction by-product of the formula IV into a pyrrole derivative of the formula I, wherein R2 is \u2014OR3, \u2014NR4R5 or halogen and R3, R4 and R5 are defined as in claim 1, provided that \u2014NR4R5 is different from \u2014NHR1.
5. The process according to claim 1, wherein the compound of formula II is obtained by
a) reacting a compound of the formula V
wherein R2 is defined as in claim 1,
with 4-fluorobenzaldehyde or
b) reacting a compound of the formula VI
wherein Hal is halogen, with a compound of the formula VII
wherein R2 is defined as in claim 1 and M+ is selected from H+, Li+, Na+ and K+, preferably Na+.
6. The process according to claim 5, wherein the compound of the formula VI is obtained by halogenating the compound of the formula VIII
7. The process according to claim 6, wherein the compound of the formula VIII is obtained by cleavage of a compound of the formula II, wherein R2 is \u2014NR4R5, and R4 and R5 are defined as in claim 1.
8. The process according to claim 5, wherein the compound of the formula V is obtained by reacting a compound of the formula IX
wherein R2 is defined as in claim 1 with benzaldehyde.
9. The process according to claim 1, wherein R1 is a straight or branched, saturated or unsaturated C1-20 hydrocarbon group which may comprise 1-5 oxygen atoms, may be substituted with 1-5 optionally protected hydroxy groups, 1 or 2 \u2014NR8R9 residues (wherein R8 and R9 are defined as in claim 1) andor 1 or 2 optionally protected carboxy groups, in which hydrocarbon group 1-5 carbon atoms may form carbonyl groups and which hydrocarbon group or part of which hydrocarbon group may form one or more rings.
10. The process according to claim 1, wherein R3, R4, R5, R6, R7, R8 and R9 are independently selected from hydrogen, a straight or branched, saturated or unsaturated C1-6 alkyl residue, a cyclic C3-6 alkyl residue or phenyl.
11. The process according to claim 1, wherein in the compound of the formula I R2 is or is converted to \u2014NH-phenyl and R1 is or is converted to a residue of the formula X
which may optionally be protected.
12. A compound of the formula I
wherein R2 is \u2014OR3 or halogen and R1 and R3 are defined as in claim 1, or a salt thereof, provided that if R3 is ethyl R1 is not \u2014CH2-phenyl.
13. A compound of the formula II
wherein R2 is \u2014OR3 or halogen and R3 is defined as in claim 1, or a salt thereof, provided that R3 is not ethyl.
14. A compound of the formula IV
wherein R1 at both occurrences are identical and defined as in claim 1, or a salt thereof.
15. A method of preparing atorvastatin comprising the step of using a compound of the formula I as defined in claim 12 for the preparation thereof.
16. A method of preparing atorvastatin comprising the step of using a compound of the formula II as defined in claim 13 for the preparation thereof.
17. A method of preparing atorvastatin comprising the step of using a compound of the formula IV as defined in claim 14 for the preparation thereof.
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. A female element of a coupling, the female element comprising:
a body having a duct for receiving a male element along a coupling axis (X-X\u2032) of the coupling;
at least one locking member including a locking portion for contacting the male element, a connecting portion, and a control portion connected to the locking portion via the connecting portion, the locking member extending generally along the axis (X-X\u2032) and being movable with combined movement in pivoting (Y-Y\u2032) and in translation along the axis (X-X\u2032) between a locked position in which the locking portion retains the male element in the body (30) along the axis (X-X\u2032), and an unlocked position in which the locking portion releases the male element so that it is movable within the duct;
an annular element (37) for moving the at least one locking member (33A, 33B, 33C) from the locked position to the unlocked position; and
at least one resilient member for returning the at least one locking member to the locked position;
the female element including longitudinally extending lateral guide means for guiding the connecting portion and the control portion during movement of the locking member, a surface of the locking portion that engages with the male element having a shape of a portion of a surface of revolution about the axis (X-X\u2032), at least one of the control portion and the connection portion of the at least one locking member has a width in a circumferential direction (Y-Y\u2032) of the control portion (332) and of the connecting portion which is less than a width of the locking portion of the at least one locking member.
2. The female element according to claim 1, wherein the portion of the surface of revolution extends over a sector of angle (\u221d330) of at least 30\xb0 relative to the axis (X-X\u2032).
3. The female element according to claim 1, wherein the locking portion has a shape of a portion of a volume of revolution.
4. The female element according to claim 3, wherein the portion of a volume of revolution is formed by two frustoconical surfaces having respective generator lines that are inclined relative to the axis (X-X\u2032) at respective angles (\u221d3302, \u221d3303) lying in a range of 30\xb0 to 60\xb0.
5. The female element according to claim 1, wherein the locking portion has a width (l330) that is greater than its thickness (e330)
6. The female element according to claim 1, wherein lateral faces of the locking portion diverge (\u221d330) going away from the duct.
7. The female element according to claim 1, wherein the body includes a through housing for the locking portion, and in that the control portion and the connecting portion are placed at the outer surface of the body of the female element.
8. The female element according to claim 7, wherein, in the locked position, the locking member co-operates with lateral faces of its housing.
9. The female element according to claim 1, wherein the guide means is at least one longitudinal groove formed in the body and in which the connecting portion and the control portion are seated so as to laterally guide the locking member.
10. The female element according to claim 9, wherein the groove has a flat bottom.
11. The female element according to claim 1, wherein the control portion forms a radial protrusion for co-operating in abutment with a shoulder formed on the annular element.
12. The female element according to claim 1, wherein a washer is placed between the resilient member and the control portion.
13. The female element according to claim 1, wherein the body includes an axial abutment for co-operating with the annular element to limit movement of the annular element in a direction for unlocking the at least one locking member.
14. The female element according to claim 1, including a plurality of distinct locking members.
15. The coupling for joining two pipes together, the coupling including a male element and a female element according to claim 1.