1. An automated seed sampler system, comprising:
an imaging device configured to obtain at least one image of a seed;
an orienting device configured to orient the seed based on the at least one image of the seed; and
a sampling station configured to remove tissue from the oriented seed.
2. The system of claim 1, wherein the imaging device includes at least one camera.
3. The system of claim 1, further comprising an imaging fixture configured to support the seed adjacent the imaging device so that the imaging device can obtain the at least one image of the seed; and wherein the orienting device is configured to orient the seed while the seed is supported within the imaging fixture.
4. The system of claim 1, wherein the orienting device includes an actuator configured to orient the seed in a desired orientation.
5. The system of claim 4, wherein the actuator is selected from the group consisting of an air-operated actuator and a mechanical actuator.
6. The system of claim 1, further comprising a seed transport subsystem configured to support the oriented seed and convey the oriented seed to the sampling station.
7. The system of claim 6, wherein the seed transport subsystem includes a seed holder for holding the oriented seed in the seed transport subsystem, and wherein the sampling station is configured to remove tissue from the oriented seed in the seed holder.
8. The system of claim 1, wherein the sampling station is configured to remove tissue from the oriented seed so as to protect germination viability of the seed.
9. The system of claim 1, further comprising a sample tray for holding the tissue removed from the oriented seed, and a seed tray for holding the seed from which the tissue is removed such that a one-to-one correspondence exists between the tissue and the seed from which the tissue is removed.
10. A method for removing tissue from a seed, the method comprising:
imaging a seed;
orienting the seed based on information obtained from imaging the seed; and
removing tissue from the oriented seed.
11. The method of claim 10, wherein imaging a seed includes suspending the seed in an imaging fixture using air, and imaging the suspended seed.
12. The method of claim 11, wherein orienting the seed includes rotating the seed in the imaging fixture to a desired orientation.
13. The method of claim 10, wherein imaging a seed includes locating a tip portion of the seed; and wherein orienting the seed includes orienting the seed based on the location of the tip portion of the seed.
14. The method of claim 10, wherein orienting the seed includes orienting the seed in a desired orientation using an actuator.
15. The method of claim 10, further comprising transporting the oriented seed in a seed transport subsystem to a sampling station for removing the tissue from the oriented seed.
16. The method of claim 10, further comprising collecting the tissue removed from the oriented seed so that a one-to-one correspondence exists between the tissue and the seed from which the tissue is removed.
17. The method of claim 10, further comprising receiving the tissue in a receptacle andor contacting the tissue with extraction fluid.
18. The method of claim 10, wherein removing tissue from the oriented seed includes removing tissue from the oriented seed while protecting germination viability of the seed.
19. The method of claim 10, further comprising analyzing the tissue for one or more characteristics indicative of at least one genetic andor chemical trait.
20. The method of claim 10, further comprising isolating the seed from a plurality of seeds prior to imaging the seed.
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 compound of general formula (Ic), or a stereoisomer, optical isomer, pharmaceutically acceptable salt, or pharmaceutically acceptable solvate thereof
wherein
R1 is phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4-alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl, or is a heterocycle, which is a saturated, partially unsaturated or aromatic ring containing 5 or 6 ring atoms of which 1, 2 or 3 are identical or different heteroatoms selected from: nitrogen, oxygen, sulfur, and phosphorus, and where the heterocycle is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, \u2014C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl;
R2 is hydrogen, C1-C6-alkyl, phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4-alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl, OR11, halogen, cyano, nitro, NR9R10 or SR11;
R3, R4 and R5 are each independently selected from: hydrogen, C1-C4-alkyl, halogen, OR11, C1-C4-alkylcarbonyloxy, NR9R10, SO2NR9R10, carboxyl, cyano and nitro;
Z is O or S;
A is a saturated or unsaturated 5-membered ring and represented by any one of the general structures (i) to (v);
wherein X1 and X2 are each independently selected from: a carbon atom and a nitrogen atom, provided that at least one of X1 and X2 is a nitrogen atom, wherein the nitrogen atom is at least monosubstituted by R13, wherein R13 is selected from: hydrogen, unsubstituted C1-C6-alkyl, or C1-C6-alkyl substituted by halogen, hydroxyl or carboxyl, C2-C6-alkenyl, hydroxyl, C1-C6-alkoxy, C1-C4-alkylcarbonyl, toluenesulfonyl, cyano, SO2R10, \u2014CO(CH2)mR14 and phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4-alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl;
R6 is \u2014C1-C4-alkyleneOR11;
R9 and R10 are each independently selected from: hydrogen, C1-C4-alkyl, C1-C4-alkanoyl, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, carboxamide and sulfonamide;
R11 is hydrogen, C1-C4-alkyl, C1-C4-alkanoyl, or C1-C4-alkoxycarbonyl;
R14 is hydrogen, C1-C4-alkyl, hydroxyl, \u2014NR9R10 halogen, \u2014SH, or \u2014S\u2014C1-C4-alkyl; and
m is an integer of 0 to 6.
2. A compound of the general formula (Id), or a stereoisomer, optical isomer, pharmaceutically acceptable salt, or pharmaceutically acceptable solvate thereof
wherein
R1 is phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl, or is a heterocycle, which is a saturated, partially unsaturated or aromatic ring containing 5 or 6 ring atoms of which 1, 2 or 3 are identical or different heteroatoms selected from: nitrogen, oxygen, sulfur, and phosphorus, and where the heterocycle is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl;
R2 is hydrogen, C1-C6-alkyl, phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4-alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl, OR11, halogen, cyano, nitro, NR9R10 or SR11;
R3, R4 and R5 are each independently selected from: hydrogen, C1-C4-alkyl, C1-C4alkoxyl, halogen, OR11, C1-C4-alkylcarbonyloxy, NR9R10, SO2NR9R10, carboxy, cyano and nitro;
A is a saturated or unsaturated 5-membered ring and represented by any one of the general structures (i) to (iv);
wherein X1 is either a nitrogen atom, and wherein R13 is selected from: hydrogen, unsubstituted C1-C6-alkyl, or C1-C6-alkyl substituted by halogen, hydroxyl or carboxyl, C2-C6-alkenyl, hydroxyl, C1-C6-alkoxy, C1-C4-alkylcarbonyl, toluenesulfonyl, cyano, SO2R10 and \u2014CO(CH2)mR14, phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4-alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl;
R6 is \u2014C1-C4-alkyleneOR11;
R9 and R10 are each independently selected from: hydrogen, C1-C4-alkyl, C1-C4-alkanoyl, C1-C4 alkoxycarbonyl, C1-C4-alkylcarbonyl, carboxamide and sulfonamide;
R11 is hydrogen, C1-C4-alkyl, C1-C4-alkanoyl, or C1-C4-alkoxycarbonyl;
R14 is hydrogen, C1-C4-alkyl, hydroxyl, \u2014NR9R10, halogen, \u2014SH, or \u2014S\u2014C1-C4-alkyl; and
m is an integer of 0 to 6.
3. A compound of the general formula (Ie), or a stereoisomer, optical isomer, pharmaceutically acceptable salt, or pharmaceutically acceptable solvate thereof
wherein
R1 is phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4-alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl, or is a heterocycle, which is a saturated, partially unsaturated or aromatic ring containing 6 ring atoms of which 1, 2 or 3 are identical or different heteroatoms selected from: nitrogen, oxygen and sulfur, and where the heterocycle is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl;
R2 and R4 are hydrogen;
R3 and R5 are each independently selected from: hydroxyl, C1-C4-alkoxyl and C1-C4-alkylcarbonyloxy;
A is a saturated or unsaturated 5-membered ring and represented by any one of the general structures (i) to (iv);
wherein X1 is either a carbon atom or a nitrogen atom, and wherein R13 is selected from: hydrogen, unsubstituted C1-C6-alkyl, or C1-C6-alkyl substituted by halogen, hydroxyl, or carboxyl, C2-C6-alkenyl, hydroxyl, C1-C6-alkoxy, C1-C4-alkylcarbonyl, toluenesulfonyl, cyano, SO2R10, \u2014CO(CH2)mR14 and phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4-alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl;
R6 is \u2014C1-C4-alkyleneOR11;
R9 and R10 are each independently selected from: hydrogen, C1-C4-alkyl, C1-C4-alkanoyl, C1-C4 alkoxycarbonyl, C1-C4-alkylcarbonyl, carboxamide and sulfonamide;
R11 is hydrogen, C1-C4-alkyl, C1-C4-alkanoyl, or C1-C4-alkoxycarbonyl;
R14 is hydrogen, C1-C4-alkyl, hydroxyl, \u2014NR9R10, halogen, \u2014SH, or \u2014S\u2014C1-C4-alkyl; and m is an integer of 0 to 6.
4. A compound of the general formula (If), or a stereoisomer, optical isomer, pharmaceutically acceptable salt, or pharmaceutically acceptable solvate thereof
wherein
R1 is phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl, or is a heterocycle, which is a saturated, partially unsaturated or aromatic ring containing 6 ring atoms of which 1, 2 or 3 are identical or different heteroatoms selected from: nitrogen, oxygen and sulfur, and where the heterocycle is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl;
R2 and R4 are hydrogen;
R3 and R5 are each independently selected from: hydroxyl, C1-C4-alkoxyl and C1-C4-alkylcarbonyloxy;
R6 is \u2014C1-C4-alkyleneOR11;
R9 and R10 are each independently selected from: hydrogen, C1-C4-alkyl, C1-C4-alkanoyl, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, carboxamide and sulfonamide;
R1 is hydrogen, C1-C4-alkyl, C1-C4-alkanoyl, or C1-C4-alkoxycarbonyl; and
R13 is hydrogen or C1-C4-alkyl.
5. A compound of the general formula (Ig), or a stereoisomer, optical isomer, pharmaceutically acceptable salt, or pharmaceutically acceptable solvate thereof
wherein
R1 is phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl, or is a heterocycle, which is a saturated, partially unsaturated or aromatic ring containing 5 or 6 ring atoms of which 1, 2 or 3 are identical or different heteroatoms selected from: nitrogen, oxygen, sulfur and phosphorus, and where the heterocycle is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl;
R2 is hydrogen, C1-C6-alkyl, phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl, OR11, halogen, cyano, nitro, NR9R10 or SR11;
R3, R4 and R5 are each independently selected from: hydrogen, C1-C4-alkyl, C1-C4-alkoxyl, halogen, OR11, C1-C4-alkylcarbonyloxy, NR9R10 SO2NR9R10, carboxyl, cyano and nitro;
Z is O or S;
A is a 5-membered saturated ring represented by any one of the general structures (i) to (v);
wherein X1 and X2 independently represent a carbon atom and a nitrogen atom provided that at least one of X1 and X2 is a nitrogen atom and wherein the nitrogen atom is at least monosubstituted by R13 wherein R13 is selected from: hydrogen, unsubstituted C1-C6-alkyl, or C1-C6-alkyl substituted by halogen, hydroxyl, or carboxyl, C2-C6-alkenyl, hydroxyl, C1-C6-alkoxy, C1-C4-alkylcarbonyl, toluenesulfonyl, SO2R10\u2014CO(CH2)mR14, cyano, phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10 SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4-alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl;
R6 is C1-C4-alkyl, \u2014C1-C4-alkanoyl, hydroxyl, C1-C4-alkoxyl, \u2014C1-C4-alkoxycarbonyl, \u2014C1-C4-alkyleneOR11, \u2014C1-C4-alkylenehalo, \u2014C1-C4-alkyleneNR9R10, C1-C4-alkyleneC(O)OR9, phenoxy, \u2014NRgRo, SR12, S(O)nR12, \u2014C(O)R12 or \u2014C(S)R12;
R9 and R10 are each independently selected from: hydrogen, C1-C4-alkyl, C1-C4-alkanoyl, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, carboxamide and sulfonamide;
R11 is hydrogen, C1-C4-alkyl, C1-C4-alkanoyl, or C1-C4-alkoxycarbonyl;
R12 is hydrogen, halogen, C1-C4-alkyl, \u2014NR9R10, or OR9;
R14 is hydrogen, C1-C4-alkyl, hydroxyl, \u2014NR9R10, halogen, \u2014SH, or \u2014S\u2014C1-C4-alkyl;
m is an integer of 0 to 6; and
n is an integer of 1 or 2.
6. A compound of general formula (Ih), or a stereoisomer, optical isomer, pharmaceutically acceptable salt, or pharmaceutically acceptable solvate thereof
wherein
R1 is phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl, or is a heterocycle, which is a saturated, partially unsaturated or aromatic ring containing 6 ring atoms of which 1, 2 or 3 are identical or different heteroatoms selected from: nitrogen, oxygen and sulfur, and where the heterocycle is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl;
R2 and R4 are hydrogen;
R3 and R5 are each independently selected from: hydroxyl, C1-C4-alkoxyl and C1-C4-alkylcarbonyloxy;
A is a 5-membered saturated ring represented by any one of the general structures (i) to (v);
wherein X1 and X2 independently represent a carbon atom and a nitrogen atom, provided that at least one of X1 and X2 is a nitrogen atom and wherein the nitrogen atom is at least monosubstituted by R13 wherein R13 is selected from: hydrogen, unsubstituted C1-C6-alkyl, or C1-C6-alkyl substituted by halogen, hydroxyl, or carboxyl, C2-C6-alkenyl, hydroxyl, C1-C6-alkoxy, C1-C4-alkylcarbonyl, toluenesulfonyl, cyano, SO2R10, \u2014CO(CH2)mR14 and phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl;
R6 is C1-C4-alkyl, \u2014C1-C4-alkanoyl, hydroxyl, C1-C4-alkoxyl, \u2014C1-C4-alkoxycarbonyl, \u2014C1-C4-alkyleneOR11, \u2014C1-C4-alkylenehalo, \u2014C1-C4-alkyleneNR9R10, \u2014C1-C4-alkyleneC(O)OR9, phenoxy, \u2014NR9R10, SR12, S(O)nR12, \u2014C(O)R12 or \u2014C(S)R12;
R9 and R10 are each independently selected from: hydrogen, C1-C4-alkyl, C1-C4-alkanoyl, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, carboxamide and sulfonamide;
R11 is hydrogen, C1-C4-alkyl, C1-C4-alkanoyl or C1-C4-alkoxycarbonyl;
R12 is hydrogen, halogen, C1-C4-alkyl, \u2014NR9R10, or OR9;
R14 is hydrogen, C1-C4-alkyl, hydroxyl, \u2014NR9R10, halogen, \u2014SH, or \u2014S\u2014C1-C4-alkyl;
m is an integer of 0 to 6; and
n is an integer of 1 or 2.
7. A compound of general formula (Ii), or a stereoisomer, optical isomer, pharmaceutically acceptable salt, or pharmaceutically acceptable solvate thereof
wherein
R1 is phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl, or is a heterocycle, which is a saturated, partially unsaturated or aromatic ring containing 6 ring atoms of which 1, 2 or 3 are identical or different heteroatoms selected from: nitrogen, oxygen and sulfur, and where the heterocycle is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl;
R2 and R4 are hydrogen;
R3 and R5 are each independently selected from: hydroxyl, C1-C4-alkoxyl and C1-C4-alkylcarbonyloxy;
A is a 5-membered saturated ring represented by any one of the general structures (i) to (iv);
wherein X1 is a carbon atom or a nitrogen atom and wherein R13 is selected from: hydrogen, unsubstituted C1-C6-alkyl, or C1-C6-alkyl substituted by halogen, hydroxyl, or carboxyl, C2-C6-alkenyl, hydroxyl, C1-C6-alkoxy, C1-C4-alkylcarbonyl, toluenesulfonyl, cyano, SO2R10, \u2014CO(CH2)mR14 and phenyl, which is unsubstituted or substituted by 1, 2, or 3 identical or different substituents selected from: halogen, C1-C4-alkyl, C1-C4-alkoxy, nitro, NR9R10, SR11, trifluoromethyl, hydroxyl, cyano, carboxy, C1-C4-alkoxycarbonyl and \u2014C1-C4-alkylenehydroxyl;
R6 is C1-C4-alkyl, \u2014C1-C4-alkanoyl, hydroxyl, C1-C4-alkoxyl, \u2014C1-C4-alkoxycarbonyl, \u2014C1-C4-alkyleneOR11, \u2014C1-C4-alkylenehalo, \u2014C1-C4-alkyleneNR9R10, \u2014C1-C4-alkyleneC(O)OR9, phenoxy \u2014NR9R10, SR2, S(O)nR2, \u2014C(O)R12 or \u2014C(S)R12;
R9 and R10 are each independently selected from: hydrogen, C1-C4-alkyl, C1-C4-alkanoyl, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, carboxamide and sulfonamide;
R11 is hydrogen, C1-C4-alkyl, C1-C4-alkanoyl, or C1-C4-alkoxycarbonyl;
R12 is hydrogen, halogen, C1-C4-alkyl, \u2014NR9R10, or OR9;
R14 is hydrogen, C1-C4-alkyl, hydroxyl, \u2014NR9R10, halogen, \u2014SH, or \u2014S\u2014C1-C4-alkyl;
m is an integer of 0 to 6; and
n is an integer of 1 or 2.
8. A compound as claimed in claim 1, wherein R1 is phenyl or pyridinyl, substituted by 1, 2 or 3 identical or different substituents selected from: halogen and nitro, R2 and R4 are hydrogen, R3 and R5 are hydroxyl, A is a saturated 5-membered ring represented by any one of the general structures (i) to (v), wherein X1, X2, R6 and R13 are as defined.
9. A compound as claimed in claim 1, wherein R1 is phenyl or pyridinyl, substituted by 1, 2 or 3 identical or different substituents selected from: halogen and nitro, R2 and R4 are hydrogen, R3 and R5 are hydroxyl, A is a saturated 5-membered ring represented by any one of the general structures (i) to (v), wherein X1 is carbon, X2 is nitrogen, R6 is \u2014C1-C4-alkylenehydroxyl, and R13 is C1-C4-alkyl.
10. A compound of the general formula (Ig) as claimed in claim 5, which is:
(+\u2212)-trans-2-(2-Chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2-Chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2-Chloro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(\u2212)-trans-2-(2-Chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(\u2212)-trans-2-(2-Chloro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(2-Bromo-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2-Bromo-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(4-Bromo-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(4-Bromo-phenyl)-5-hydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-7-methoxy-chromen-4-one;
(+)-trans-2-(4-Bromo-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(3-Chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(3-Chloro-phenyl)-5-hydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-7-methoxy-chromen-4-one;
(+)-trans-2-(3-Chloro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-2-(2-iodo-phenyl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-5,7-Dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-2-(2-iodo-phenyl)-chromen-4-one;
(+)-trans-2-(2-Fluoro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2-Fluoro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(3-Fluoro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(3-Fluoro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2,6-Difluoro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2,6-Difluoro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-4-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-4-oxo-4H-chromen-2-yl-benzonitrile;
(+\u2212)-trans-4-5,7-Dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4-oxo-4H-chromen-2-yl-benzonitrile;
(+)-trans-4-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-4-oxo-4H-chromen-2-yl-benzonitrile;
(+)-trans-4-5,7-Dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4-oxo-4H-chromen-2-yl-benzonitrile;
(+\u2212)-trans-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-2-(4-trifluoromethyl-phenyl)-chromen-4-one;
(+\u2212)-trans-5,7-Dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-2-(4-trifluoromethyl-phenyl)-chromen-4-one;
(+)-trans-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-2-(4-trifluoromethyl-phenyl)-chromen-4-one;
(+)-trans-5,7-Dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-2-(4-trifluoromethyl-phenyl)-chromen-4-one;
(\u2212)-trans-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-2-(4-trifluoromethyl-phenyl)-chromen-4-one;
(\u2212)-trans-5,7-Dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-2-(4-trifluoromethyl-phenyl)-chromen-4-one;
(+)-trans-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-2-phenyl-chromen-4-one;
(+)-trans-5,7-Dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-2-phenyl-chromen-4-one;
(+)-trans-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-2-thiophen-2-yl-chromen-4-one;
(+)-trans-5,7-Dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-2-thiophen-2-yl-chromen-4-one;
(+)-trans-4-5,7-Dihydroxy-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4-oxo-4H-chromen-2-yl-3-methyl-benzonitrile;
(+)-trans-4-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-4-oxo-4H-chromen-2-yl-3-methyl-benzonitrile;
(+\u2212)-trans-2-(2-Bromo-5-methoxy-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+\u2212)-trans-2-(2-Bromo-5-methoxy-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(2-Bromo-5-methoxy-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2-Bromo-5-methoxy-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(2-Bromo-5-hydroxy-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(2-Bromo-5-hydroxy-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(3,5-Bis-trifluoromethyl)-phenyl-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+\u2212)-trans-2-(3,5-Bis-trifluoromethyl)-phenyl-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(2-Chloro-5-methyl-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2-Chloro-5-methyl-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(2-Bromo-5-nitro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+\u2212)-trans-2-(2-Bromo-5-nitro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dihydroxy-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-pyridin-3-yl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-pyridin-3-yl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(2-Bromo-5-nitrophenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dihydroxy-chromen-4-one;
(+)-trans-2-(2-Chloro-pyridin-3-yl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-2-(4-nitrophenyl)-4H-chromen-4-one;
(+\u2212)-trans-5,7-Dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-2-(4-nitrophenyl)-chromen-4-one;
(+\u2212)-trans-2-(4-Aminophenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-2-(2-methoxy-phenyl)-chromen-4-one;
(+\u2212)-trans-5,7-Dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-2-(2-hydroxy-phenyl)-chromen-4-one;
(+)-trans-3-Chloro-4-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-4-oxo-4H-chromen-2-yl-benzonitrile;
(+)-trans-3-Chloro-4-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4-oxo-4H-chromen-2-yl-benzonitrile;
(+)-trans-2-(4-Bromo-2-chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(4-Bromo-2-chloro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-4-dimethylamino-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-4-methylamino-phenyl)-5,7-dihydroxy-8-(2-hydroxy methyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-4-methoxy-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-4-hydroxy-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-5-fluoro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-5-fluoro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-5-methoxy-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-5-hydroxy-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-5-methoxy-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-8-(2-Azidomethyl-1-methyl-pyrrolidin-3-yl)-2-(2-chloro-phenyl)-5,7-dimethoxy-chromen-4-one;
(+\u2212)-trans-8-(2-Aminomethyl-1-methyl-pyrrolidin-3-yl)-2-(2-chloro-phenyl)-5,7-dimethoxy-chromen-4-one;
(+\u2212)-trans-8-(2-Aminomethyl-1-methyl-pyrrolidin-3-yl)-2-(2-chloro-phenyl)-5,7-dihydroxy-chromen-4-one;
(+\u2212)-trans-3-{2-(2-Chloro-phenyl)-5,7-dimethoxy-4-oxo-4H-chromen-8-yl-1-methyl-pyrrolidin-2-yl}-acetonitrile;
(+\u2212)-trans-{3-2-(2-Chloro-phenyl)-5,7-dihydroxy-4-oxo-4H-chromen-8-yl-1-methyl-pyrrolidin-2-yl}-acetonitrile;
(+\u2212)-trans-2-2-Chloro-phenyl-8-(2-mercaptomethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-phenyl)-5,7-dihydroxy-8-(2-mercaptomethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-Acetic acid 3-2-(2-chloro-phenyl)-5,7-dimethoxy-4-oxo-4H-chromen-8-yl-1-(4-methoxy-phenyl)-pyrrolidin-2-ylmethyl ester;
(+\u2212)-trans-2-(2-Chloro-phenyl)-8-2-hydroxymethyl-1-(4-methoxy-phenyl)-pyrrolidin-3-yl-5,7-dimethoxy-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-phenyl)-5,7-dihydroxy-8-2-hydroxymethyl-1-(4-methoxy-phenyl)-pyrrolidin-3-yl-chromen-4-one;
(+\u2212)-trans-Acetic acid-3-2-(2-chloro-phenyl)-5,7-dimethoxy-4-oxo-4H-chromen-8-yl-1-propyl-pyrrolidin-2-ylmethyl ester;
(+\u2212)-trans-2-(2-Chloro-phenyl)-8-(2-hydroxymethyl-1-propyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-propyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-4-nitro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(2-Bromo-4-nitro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-3-Chloro-4-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4-oxo-4H-chromen-2-yl-benzoic acid;
(+\u2212)-trans-3-Bromo-4-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4-oxo-4H-chromen-2-yl-benzoic acid;
(+\u2212)-trans-2-(2-Chloro-4-fluoro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(4-Amino-2-chloro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(2-Bromo-4-fluoro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(4-Amino-2-bromo-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-4-Chloro-3-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4-oxo-4H-chromen-2-yl-benzoic acid;
(+\u2212)-trans-4-Bromo-3-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4-oxo-4H-chromen-2-yl-benzoic acid;
(+\u2212)-trans-4-Bromo-3-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4-oxo-4H-chromen-2-yl-N-hydroxy-benzamide;
(+\u2212)-trans-4-Chloro-3-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4-oxo-4H-chromen-2-yl-N-hydroxy-benzamide;
(+\u2212)-trans-3-Chloro-4-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4-oxo-4H-chromen-2-yl-N-hydroxy-benzamide;
(+\u2212)-trans-3-Bromo-4-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4-oxo-4H-chromen-2-yl-N-hydroxy-benzamide; or
(+\u2212)-trans-2-(2,4-Difluoro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(2-Chloro-3-fluoro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2-Chloro-3-fluoro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(2-Bromo-3-fluoro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2-Bromo-3-fluoro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(2-Bromo-5-fluoro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2-Bromo-5-fluoro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(2-Chloro-5-iodo-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2-Chloro-5-iodo-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(2-Bromo-5-chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2-Bromo-5-chloro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+\u2212)-trans-2-(2-Chloro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-1-oxy-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(2-Bromo-4-nitro-phenyl)-8-(2-hydroxymethyl-1-methylpyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2-Bromo-4-nitro-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(4-Amino-2-bromo-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(4-Amino-2-bromo-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(2-Bromo-4-methoxy-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one;
(+)-trans-2-(2-Bromo-4-methoxy-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-2-(2-Bromo-4-hydroxy-phenyl)-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one;
(+)-trans-Acetic acid 8-(2-acetoxymethyl-1-methyl-pyrrolidin-3-yl)-5-hydroxy-2-(4-nitro-phenyl)-4-oxo-4H-chromen-7-yl ester;
(+)-trans-2-(2,4-Dichloro-5-fluoro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one; or
(+)-trans-2-(2,4-Dichloro-5-fluoro-phenyl-5,7-dihydroxy-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-chromen-4-one.
11. A pharmaceutical composition comprising a compound of general formula (Ic) or a stereoisomer, optical isomer, pharmaceutically acceptable salt, or pharmaceutically acceptable solvate thereof as claimed in claim 1, and a pharmaceutically acceptable carrier.
12. A process for the preparation of a compound of general formula (Ic), as claimed in claim 1, or a pharmaceutically acceptable salt thereof:
wherein
R1, R2, R3, R4, R5, R6 and A are as defined in claim 1, which process comprises reacting a compound of formula (XA):
or a compound of formula (XIIA):
wherein in each case R1, R2, R3, R4, R5, R6 and A are as defined in claim 1, with an organic or inorganic base, subsequently adding an acid to the reaction mixture capable of effecting cyclization, then adding an organic or inorganic base, and, optionally, converting the compound of formula (Ic) into a pharmaceutically acceptable salt.
13. A process according to claim 12, wherein the compound of formula (XIIA) is obtained by reacting a compound of formula (XIA)
wherein R2, R3, R4, R5, R6 and A are as defined in claim 12, with a carboxylic acid ester, an acid halide, or an activated ester in the presence of an organic or inorganic base in organic or inorganic solvent.
14. A process for the preparation of a compound of formula (XIIIA) or a pharmaceutically acceptable salt thereof:
wherein R1, R2, R3, R4, R5 and R13 are as defined in claim 1, comprising reacting a compound of formula (VIIA)
wherein R1, R2, R3, R4, R5 and R13 are as defined in claim 1, with a reagent suitable to effect replacement of the \u2014OH group on the piperidino ring by a leaving group, in the presence of an organic or inorganic base, followed by adding a suitable organic base in the presence of a suitable organic solvent to effect contraction of the piperidino ring, and, optionally, converting the resultant compound of formula (XIII) into a pharmaceutically acceptable salt.
15. The compound of claim 4, wherein R11 is hydrogen.