Muscarinic agonists
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Abstract
Compounds and methods are provided for the treatment of disease conditions in which modification of cholinergic, especially muscarinic m1, m4, or both m1 and m4, receptor activity has a beneficial effect. In the method, an effective amount of a compound is administered to a patient in need of such treatment.
26 Citations
76 Claims
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1. A compound of formula (I):
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76)
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2. The compound of claim 1, wherein each t is 2 and R10 is straight- or branched-chain C2-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 alkylidene, C1-8 alkoxy, or C1-8 heteroalkyl.
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3. The compound of claim 2, wherein R10 is n-butyl.
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4. The compound of claim 1, wherein Z1 is CR1 or N, Z2 is CR2, Z3 is CR3 or N, and Z4 is CR4.
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5. The compound of claim 4, wherein each R1, R2, R3, and R4, independently, is H, halo, —
- NO2, or straight- or branched-chain C1-4 alkyl, or R1 and R2 together form —
NH—
N═
N—
or R3 and R4 together form —
NH—
N═
N—
.
- NO2, or straight- or branched-chain C1-4 alkyl, or R1 and R2 together form —
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6. The compound of claim 2, wherein Y is absent or O, p is 0, 1, 2 or 3, and R8 and R9 are H.
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7. The compound of claim 6, wherein Z is absent, Y is absent and p is 3.
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8. The compound of claim 7, wherein R10 is n-butyl.
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9. The compound of claim 2, wherein the compound is of the formula
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10. The compound of claim 9, wherein Z is absent, Y is absent and p is 3.
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11. The compound of claim 10, wherein R10 is n-butyl.
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12. The compound of claim 9, wherein R5 is H or C1-6 alkyl.
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13. The compound of claim 2, wherein the compound is of the formula
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14. The compound of claim 13, wherein Z is absent, Y is absent and p is 3.
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15. The compound of claim 14, wherein R10 is n-butyl.
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16. The compound of claim 13, wherein R5 is H or C1-6 alkyl.
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17. The compound of claim 1, wherein the compound is:
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2-(3-(4-n-butylpiperidine-1-yl)-propyl)-benzothiazole;
2-(3-(4-n-butylpiperidine-1-yl)-propyl)-benzooxazole;
4,5-difluoro-2-(3-(4-n-butylpiperidine-1-yl)-propyl)-1H-benzoimidazole;
6-fluoro-5-nitro-2-(3-(4-n-butylpiperidine-1-yl)-propyl)-1H-benzoimidazole;
5-tert-butyl-2-(3-(4-n-butylpiperidine-1-yl)-propyl)-1H-benzoimidazole;
5-chloro-6-methyl-2-(3-(4-n-butylpiperidine-1-yl)-propyl)-1H-benzoimidazole;
4,6-difluoro-2-(3-(4-n-butylpiperidine-1-yl)-propyl)-1H-benzoimidazole;
2-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-imidazo[4,5-c]pyridine;
8-(3-(4-n-butylpiperidine)-1-yl-propyl)-9H-purine;
7-(3-(4-n-butylpiperidine)-1-yl-propyl)-3,8-dihydroimidazo[4′
,5′
;
3,4]benzo[1,2-d][1,2,3]triazole;
2-(3-(4-n-butylpiperidine)-1-yl-propyl)-3a,4,5,6,7,7a-hexahydro-1H-benzoimidazole;
1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indole;
1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-benzoimidazole;
3-methyl-1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indole;
5-bromo-1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indole;
3-formyl-1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indole;
7-bromo-1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indole;
1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indazole;
3-(3-(4-n-butylpiperidine)-1-yl-propyl)-benzo[d]isoxazole;
3-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indole;
4-nitro-2-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-benzoimidazole;
5-nitro-2-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-benzoimidazole;
4-hydroxy-2-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-benzoimidazole;
2-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-benzoimidazole;
4-methyl-2-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-benzoimidazole;
3-(2-(4-n-butylpiperidine)-1-yl-ethyl)-1H-indole;
3-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indazole;
3-(2-(4-n-butylpiperidine)-ethoxy)-7-methyl-benzo[d]isoxazole;
1-(3-(4-Methylpiperidine)-1-yl-propyl)-1H-indazole;
1-(3-(4-Pentylpiperidine)-1-yl-propyl)-1H-indazole;
1-(3-(4-Propylpiperidine)-1-yl-propyl)-1H—
;
1-(3-(4-(3-Methyl-butyl)-piperidine)-1-yl-propyl)-1H-indazole 1-(3-(4-Pentylidene-piperidine)-1-yl-propyl)-1H-indazole;
1-(3-(4-Propylidene-piperidine)-1-yl-propyl)-1H-indazole 1-Benzo[b]thiophen-2-yl-4-(4-butylpiperidin-1-yl)-butan-1-one 4-(4-Butylpiperidin-1-yl)-1-(3-methyl-benzofuran-2-yl)-butan-1-one;
4-(4-Butylpiperidin-1-yl)-1-(5-fluoro-3-methyl-benzo[b]thiophen-2-yl)-butan-1-one;
1-Benzofuran-2-yl-4-(4-butylpiperidin-1-yl)-butan-1-one;
1-(3-Bromo-benzo[b]thiophen-2-yl)-4-(4-butylpiperidin-1-yl)-butan-1-one 1-(3-Benzo[b]thiophen-2-yl-propyl)-4-butylpiperidine;
1-(3-Benzofuran-2-yl-propyl)4-butylpiperidine;
4-Butyl-1-[3-(3-methyl-benzofuran-2-yl)-propyl]-piperidine;
4-Butyl-1-[3-(5-fluoro-3-methyl-benzo[b]thiophen-2-yl)-propyl]-piperidine;
2-(3-Iodo-propyl)-benzo[b]thiophene;
1-(3-Benzo[b]thiophen-2-yl-propyl)-4-methylpiperidine 1-(3-Benzo[b]thiophen-2-yl-propyl)-4-benzylpiperidine;
1-(3-Benzo[b]thiophen-2-yl-propyl)-4-(2-methoxy-phenyl)-piperidine;
2-(3-Bromopropyl)-2H-benzotriazole;
2-[3-(4-Butylpiperidin-1-yl)-propyl]-2H-benzotriazole;
1-(3-Bromopropyl)-1H-benzotriazole;
1-[3-(4-Butylpiperidin-1-yl)-propyl]-1H-benzotriazole;
1-[3-(4-Butylpiperidin-1-yl)-propyl]-1H-indole-3-carbaldehyde;
{1-[3-(4-Butylpiperidin-1-yl)-propyl]-1H-indol-3-yl}-methanol;
1-[3-(4-Butylpiperidin-1-yl)-propyl]-2-phenyl-1H-benzoimidazole;
1-[3-(4-Butylpiperidin-1-yl)-propyl]-3-chloro-1H-indazole;
1-[3-(4-Butylpiperidin-1-yl)-propyl]-6-nitro-1H-indazole;
Benzo[d]isoxazol-3-ol;
3-(2-Chloroethoxy)-benzo[d]isoxazole;
3-[2-(4-Butylpiperidin-1-yl)-ethoxy]-benzo[d]isoxazol;
3-(1H-Indol-3-yl)-propan-1-ol;
3-[3-(4-Butyl-piperidin-1-yl)-propyl]-1H-indole hydrochloride;
4-(4-Butylpiperidine-1-yl)-butyric acid methyl ester;
2-[3-(4-Butylpiperidin-1-yl)-propyl]-1-methyl-1H-benzimidazole;
1H-Indazole-3-carboxylic acid (2-(4-butylpiperidin)-1-yl-ethyl)-amide;
1-[3-(4-Butylpiperidin-1-yl)-propyl]-5-nitro-1H-indazole;
2-[3-(4-butylpiperidin-1-yl)-propyl]-5-nitro-2H-indazole;
1-[3-(4-Butyl-piperidin-1-yl)-propyl]-2-methyl-1H-indole;
1-{1-[3-(4-Butyl-piperidin-1-yl)-propyl]-1H-indol-3-yl}-ethanone;
{1-[3-(4-Butyl-piperidin-1-yl)-propyl]-1H-indol-3-yl}-acetonitrile;
1-[3-(4-Butyl-piperidin-1-yl)-propyl]-1H-indole-3-carbonitrile;
1-[3-(4-Butyl-piperidin-1-yl)-propyl]-5,6-dimethyl-1H-benzoimidazole;
1-[3-(4-Butyl-piperidin-1-yl)-propyl]-5(6)-dimethyl-1H-benzoimidazole;
1-[3-(4-Butyl-piperidin-1-yl)-propyl]-5-methoxy-1H-benzoimidazole;
{1-[3-(4-Butyl-piperidin-1-yl)-propyl]-1H-benzoimidazol-2-yl}-methanol;
1-[3-(4-Butyl-piperidin-1-yl)-propyl]-2-trifuoromethyl-1H-benzoimidazole;
(2-Trimethylstannanyl-phenyl)-carbamic acid tert-butyl ester;
[2-(4-Chloro-butyryl)-phenyl]-carbamic acid tert-butyl ester;
{2-[4-(4-Butyl-piperidine-1-yl)-butyryl]-phenyl}-carbamic acid tert-butyl ester;
3-[3-(4-Butyl-piperidine-1-yl)-propyl]-1H-indazole, HCl;
3-[3-(4-Butyl-piperidine-1-yl)-propyl]-5-nitro-1H-indazole;
3-[3-(4-Butyl-piperidine-1-yl)-propyl]-5,7-dinitro-1H-indazole;
4-(4-Butyl-piperidin-1-yl)-1-(2-metylsulfanyl-phenyl)-butan-1-one;
3-[3-(4-Butyl-piperidin-1-yl)-propyl]-benzo[d]isothiazole;
3-[3-(4-Butyl-piperidin-1-yl)-propyl]-5-methoxy-1H-indazole;
3-[3-(4-Butyl-piperidin-1-yl)-propyl]-4-methoxy-1H-indazole 3-[3-(4-Butyl-piperidin-1-yl)-propyl]-6-methoxy-1H-indazole;
3-[3-(4-Butyl-piperidin-1-yl)-propyl]-1H-indazole-4-ol (53MF51);
3-[3-(4-Butyl-piperidin-1-yl)-propyl]-1H-indazole-6-ol (53MF52);
or3-[3-(4-Butyl-piperidin-1-yl)-propyl]-1H-indazole-5-ol
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47. A method of activating a cholinergic receptor comprising contacting the cholinergic receptor or a system containing the cholinergic receptor with an effective amount of at least one compound of claim 1.
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48. The method of claim 47 wherein the compound is a cholinergic agonist.
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49. The method of claim 47 wherein the compound is selective for the m1, m4, or both the m1 and m4 muscarinic receptor subtype.
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50. The method of claim 47 wherein the cholinergic receptor is a muscarinic receptor.
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51. The method of claim 47 wherein the muscarinic receptor is the m1 or m4 muscarinic receptor subtype.
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52. The method of claim 47 wherein the muscarinic receptor is in the central nervous system.
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53. The method of claim 47 wherein the muscarinic receptor is in the peripheral nervous system.
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54. The method of claim 47 wherein the muscarinic receptor is in the gastrointestinal system, heart, endocrine glands, or lungs.
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55. The method of claim 47 wherein the muscarinic receptor is truncated, mutated, or modified.
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56. A method of treating a disease condition associated with a cholinergic receptor comprising administering to a subject in need of such treatment an effective amount of at least one compound of claim 1.
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57. The method of claim 56 wherein the disease condition is selected from the group consisting of cognitive impairment, forgetfulness, confusion, memory loss, attentional deficits, deficits in visual perception, depression, pain, sleep disorders, psychosis, hallucinations, aggressiveness, paranoia, and increased intraocular pressure.
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58. The method of claim 56 wherein the disease condition is selected from the group consisting of neurodegenerative disease, Alzheimer'"'"'s disease, Parkinson'"'"'s disease, Huntington'"'"'s chorea, Friederich'"'"'s ataxia, Gilles de la Tourette'"'"'s Syndrome, Down Syndrome, Pick disease, dementia, clinical depression, age-related cognitive decline, attention-deficit disorder, sudden infant death syndrome, and glaucoma.
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59. The method of claim 56 wherein the disease condition is associated with a cholinergic receptor dysfunction.
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60. The method of claim 56 wherein the disease condition is associated with decreased activity of a cholinergic receptor.
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61. The method of claim 56 wherein the disease condition is associated with loss of cholinergic receptors.
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62. The method of claim 56 wherein the cholinergic receptor is a muscarinic receptor.
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63. The method of claim 62 wherein the muscarinic receptor is the m1 or m4 muscarinic receptor subtype.
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64. The method of claim 62 wherein the muscarinic receptor is in the central nervous system.
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65. The method of claim 62 wherein the muscarinic receptor is in the peripheral nervous system.
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66. The method of claim 62 wherein the muscarinic receptor is in gastrointestinal system, heart, endocrine glands, or lungs.
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67. The method of claim 62 wherein the muscarinic receptor is truncated, mutated, or modified.
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68. A method of treating a disease condition associated with reduced levels of acetylcholine comprising administering to a subject in need of such treatment an effective amount of at least one compound of claim 1.
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69. A method of treating Alzheimer'"'"'s Disease comprising administering to a subject in need of such treatment an effective amount of at least one compound of claim 1.
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70. A method of treating cognitive impairment comprising administering to a subject in need of such treatment an effective amount of at least one compound of claim 1.
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71. A method of treating glaucoma comprising administering to a subject in need of such treatment an effective amount of at least one compound of claim 1.
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72. A method of treating pain comprising administering to a subject in need of such treatment an effective amount of at least one compound of claim 1.
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73. A method of treating schizophrenia comprising administering to a subject in need of such treatment an effective amount of at least one compound of claim 1.
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74. A method for identifying a genetic polymorphism predisposing a subject to being responsive to amount of at least one compound of claim 1, comprising:
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administering to a subject an therapeutically effective amount of the compound;
measuring the response of said subject to said compound, thereby identifying a responsive subject having an ameliorated disease condition associated with a cholinergic receptor; and
identifying a genetic polymorphism in the responsive subject, wherein the genetic polymorphism predisposes a subject to being responsive to the compound.
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75. The method of claim 74 wherein the ameliorated disease condition is associated with the m1 or m4 muscarinic receptor subtype.
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76. A method for identifying a subject suitable for treatment with at least one compound of claim 1, comprising detecting the presence of a polymorphism in a subject wherein the polymorphism predisposes the subject to being responsive to said compound, and wherein the presence of the polymorphism indicates that the subject is suitable for treatment with said compound of claim 1.
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2. The compound of claim 1, wherein each t is 2 and R10 is straight- or branched-chain C2-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 alkylidene, C1-8 alkoxy, or C1-8 heteroalkyl.
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18. A pharmaceutical composition comprising an effective amount of a compound of formula (I):
- View Dependent Claims (19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34)
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19. The pharmaceutical composition of claim 18, wherein each t is 2 and R10 is straight- or branched-chain C2-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 alkylidene, C1-8 alkoxy, or C1-8 heteroalkyl.
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20. The pharmaceutical composition of claim 19, wherein R10 is n-butyl.
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21. The pharmaceutical composition of claim 19, wherein Z1 is CR1 or N, Z2 is CR2, Z3 is CR3 or N, and Z4 is CR4.
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22. The pharmaceutical composition of claim 21, wherein each R1, R2, R3, and R4, independently, is H, halo, —
- NO2, or straight- or branched-chain C1-6 alkyl, or R1 and R2 together form —
NH—
N═
N—
or R3 and R4 together form —
NH—
N═
N—
.
- NO2, or straight- or branched-chain C1-6 alkyl, or R1 and R2 together form —
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23. The pharmaceutical composition of claim 19, wherein Y is absent or O, p is 0, 1, 2 or 3, and R and R9 are H.
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24. The pharmaceutical composition of claim 23, wherein Z is absent, Y is absent and p is 3.
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25. The pharmaceutical composition of claim 24, wherein R10 is n-butyl.
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26. The pharmaceutical composition of claim 19, wherein the compound is of the formula
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27. The pharmaceutical composition of claim 26, wherein Z is absent, Y is absent and p is 3.
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28. The pharmaceutical composition of claim 27, wherein R10 is n-butyl.
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29. The pharmaceutical composition of claim 26, wherein R5 is H or C1alkyl.
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30. The pharmaceutical composition of claim 19, wherein the compound is of the formula
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31. The pharmaceutical composition of claim 30, wherein Z is absent, Y is absent and p is 3.
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32. The pharmaceutical composition of claim 31, wherein R10 is n-butyl.
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33. The pharmaceutical composition of claim 30, wherein R5 is H or C1-4 alkyl.
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34. The pharmaceutical composition of claim 19, wherein the compound is:
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2-(3-(4-n-butylpiperidine-1-yl)-propyl)-benzothiazole;
2-(3-(4-n-butylpiperidine-1-yl)-propyl)-benzooxazole;
4,5-difluoro-2-(3-(4-n-butylpiperidine-1-yl)-propyl)-1H-benzoimidazole;
6-fluoro-5-nitro-2-(3-(4-n-butylpiperidine-1-yl)-propyl)-1H-benzoimidazole;
5-tert-butyl-2-(3-(4-n-butylpiperidine-1-yl)-propyl)-1H-benzoimidazole;
5-chloro-6-methyl-2-(3-(4-n-butylpiperidine-1-yl)-propyl)-1H-benzoimidazole;
4,6-difluoro-2-(3-(4-n-butylpiperidine-1-yl)-propyl)-1H-benzoimidazole;
2-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-imidazo[4,5-c]pyridine;
8-(3-(4-n-butylpiperidine)-1-yl-propyl)-9H-purine;
7-(3-(4-n-butylpiperidine)-1-yl-propyl)-3,8-dihydroimidazo[4′
5′
;
3, 4]benzo[1,2-d][1, 2, 3]triazole;
2-(3-(4-n-butylpiperidine)-1-yl-propyl)-3a,4,5,6,7,7a-hexahydro-1H-benzoimidazole;
1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indole;
1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-benzoimidazole;
3-methyl-1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indole;
5-bromo-1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indole;
3-formyl-1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indole;
7-bromo-1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indole;
1-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indazole;
3-(3-(4-n-butylpiperidine)-1-yl-propyl)-benzo[d]isoxazole;
3-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indole;
4-nitro-2-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-benzoimidazole;
5-nitro-2-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-benzoimidazole;
4-hydroxy-2-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-benzoimidazole;
2-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-benzoimidazole;
4-methyl-2-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-benzoimidazole;
3-(2-(4-n-butylpiperidine)-1-yl-ethyl)-1H-indole;
or3-(3-(4-n-butylpiperidine)-1-yl-propyl)-1H-indazole.
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19. The pharmaceutical composition of claim 18, wherein each t is 2 and R10 is straight- or branched-chain C2-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 alkylidene, C1-8 alkoxy, or C1-8 heteroalkyl.
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35. A method of increasing an activity of a cholinergic receptor comprising contacting the cholinergic receptor or a system containing the cholinergic receptor with an effective amount of at least one compound of formula (I):
- View Dependent Claims (36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46)
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36. The method of claim 35 wherein the cholinergic receptor is a muscarinic receptor.
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37. The method of claim 36 wherein the muscarinic receptor is of the m1 muscarinic receptor subtype.
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38. The method of claim 36 wherein the muscarinic receptor is of the m4 muscarinic receptor subtype.
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39. The method of claim 36 wherein the muscarinic receptor is in the central nervous system.
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40. The method of claim 36 wherein the muscarinic receptor is in the peripheral nervous system.
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41. The method of claim 36 wherein the muscarinic receptor is in the gastrointestinal system, heart, endocrine glands, or lungs.
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42. The method of claim 36 wherein the muscarinic receptor is truncated, mutated, or modified.
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43. The method of claim 35 wherein the activity is a signaling activity of a cholinergic receptor.
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44. The method of claim 35 wherein the activity is associated with muscarinic receptor activation.
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45. The method of claim 35 wherein the compound is a cholinergic agonist.
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46. The method of claim 35 wherein the compound is selective for the m1, or m4 muscarinic receptor subtype, or both the m1 and m4 muscarinic receptor subtypes.
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36. The method of claim 35 wherein the cholinergic receptor is a muscarinic receptor.
Specification
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Current AssigneeAllan K. Uldam, Bo Lennart M. Friberg, Carl-Magnus A. Anderson, Niels Skjaerbaek, Tracy A. Spalding
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Original AssigneeAllan K. Uldam, Bo Lennart M. Friberg, Carl-Magnus A. Anderson, Niels Skjaerbaek, Tracy A. Spalding
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InventorsUldam, Allan K., Anderson, Carl-Magnus A., Skjaerbaek, Niels, Friberg, Bo Lennart M., Spalding, Tracy A.
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Granted Patent
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Time in Patent OfficeDays
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Field of Search
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US Class Current514/210.210
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CPC Class CodesA61P 25/02 for peripheral neuropathiesA61P 25/04 Centrally acting analgesics...A61P 25/14 for treating abnormal movem...A61P 25/16 Anti-Parkinson drugsA61P 25/18 Antipsychotics, i.e. neurol...A61P 25/20 Hypnotics; SedativesA61P 25/24 AntidepressantsA61P 25/28 for treating neurodegenerat...A61P 27/02 Ophthalmic agentsA61P 27/06 Antiglaucoma agents or mioticsA61P 29/00 Non-central analgesic, anti...A61P 43/00 Drugs for specific purposes...C07D 401/06 linked by a carbon chain co...C07D 405/06 linked by a carbon chain co...C07D 409/06 linked by a carbon chain co...C07D 413/06 linked by a carbon chain co...C07D 413/12 linked by a chain containin...C07D 417/06 linked by a carbon chain co...C07D 471/04 Ortho-condensed systemsC07D 473/00 Heterocyclic compounds cont...C07D 487/04 : Ortho-condensed systems