Gamma-amino-butyric acid derivatives as GABA B receptor ligands
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Abstract
Gamma-amino-butyric acid derivatives that are GABAB receptor ligands, pharmaceutical compositions comprising such derivatives, and methods of using such derivatives and pharmaceutical compositions thereof for treating diseases are disclosed.
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Citations
28 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, 18, 19, 20, 21, 22, 23, 24, 25)
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2. The compound of claim 1, wherein the compound is of Formula (II):
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3. The compound of claim 1, wherein R1 and R2 are independently chosen from halogen.
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4. The compound of claim 1, wherein:
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R1 is hydrogen; and R2 is chloro.
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5. The compound of claim 1, wherein:
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R3 is —
X—
Y; andR4 is hydrogen.
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6. The compound of claim 1, wherein:
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R3 is hydrogen; and R4 is —
X—
Y.
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7. The compound of claim 1, wherein X is C1-3 heteroalkyldiyl and is chosen from —
- NH(CHR7)n—
, —
O(CHR7)n—
, and —
NH—
SO2—
;
wherein n is chosen from 0, 1, and 2; and
each R7 is independently chosen from hydrogen and C1-4 alkyl.
- NH(CHR7)n—
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8. The compound of claim 1, wherein X is chosen from substituted C1-3 alkyldiyl and substituted C1-3 heteroalkyldiyl, wherein each of the one or more substituents is independently chosen from —
- OH, —
NH2, C1-4 alkyl, C1-4 alkoxy, and ═
O.
- OH, —
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9. The compound of claim 1, wherein Y is chosen from substituted C6-12 aryl and substituted C5-12 heteroaryl, wherein each of the one or more substituents is independently chosen from halogen, —
- OH, —
NH2, —
NO2, —
CN, —
COOH, —
CF3, —
OCF3, C1-4 alkyl, substituted C1-4 alkyl, C1-4 heteroalkyl, and substituted C1-4 heteroalkyl.
- OH, —
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10. The compound of claim 9, wherein:
- each of the one or more substituents of substituted C1-4 alkyl is chosen from —
OH, ═
O, —
OCH3, —
SCH3, —
N(CH3)2, and —
OCH2CH3; and
substituted C1-4 heteroalkyl is chosen from —
C(O)NH2, —
CH2COOH, —
COOCH3, —
COOCH2CH3, and —
SO2CH3.
- each of the one or more substituents of substituted C1-4 alkyl is chosen from —
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11. The compound of claim 1, wherein Y is chosen from phenyl, substituted phenyl, C5 heteroaryl, substituted C5 heteroaryl, C6 heteroaryl, and substituted C6 heteroaryl.
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12. The compound of claim 1, wherein Y is chosen from phenyl, substituted phenyl, thienyl, substituted thienyl, furyl, substituted furyl, imidazolyl, substituted imidazolyl, thiazole, substituted thiazole, oxazole, substituted oxazole, thiazolidine, substituted thiazolidine, oxazolidine, substituted oxazolidine, oxadiazole, substituted oxadiazole, thiadiazole, substituted thiadiazole, pyridyl, substituted pyridyl, indazolyl, substituted indazolyl, isoquinolyl, and substituted isoquinolyl.
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13. The compound of claim 2, wherein:
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R1 is hydrogen; R2 is chloro; R3 is hydrogen; and R4 is —
X—
Y wherein;X is chosen from a covalent bond, C1-3 alkyldiyl, substituted C1-13 alkyldiyl, —
NH(CHR7)n—
, —
O(CHR7)n—
, and —
NH—
SO2—
;
wherein n is chosen from 0, 1, and 2; and
each R7 is independently chosen from hydrogen and C1-4 alkyl; andY is chosen from phenyl, substituted phenyl, C5 heteroaryl, substituted C5 heteroaryl, C6 heteroaryl, and substituted C6 heteroaryl.
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14. The compound of claim 13, wherein Y is chosen from phenyl, substituted phenyl, thienyl, substituted thienyl, furyl, substituted furyl, imidazolyl, substituted imidazolyl, thiazole, substituted thiazole, oxazole, substituted oxazole, thiazolidine, substituted thiazolidine, oxazolidine, substituted oxazolidine, oxadiazole, substituted oxadiazole, thiadiazole, substituted thiadiazole, pyridyl, and substituted pyridyl wherein:
each of the one or more substituent groups is independently chosen from halogen, —
OH, —
NH2, —
NO2, —
CN, —
COOH, —
CF3, —
OCF3, C1-4 alkyl, substituted C1-4 alkyl, C1-4 heteroalkyl, and substituted C1-4 heteroalkyl.
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15. The compound of claim 2, wherein:
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R1 is hydrogen; R2 is chloro; R3 is —
X—
Y wherein;X is chosen from a covalent bond, C1-13 alkyldiyl, substituted C1-13 alkyldiyl, —
NH(CHR7)n—
, —
O(CHR7)n—
, and —
NH—
SO2—
;
wherein n is chosen from 0, 1, and 2; and
each R7 is independently chosen from hydrogen and C1-4 alkyl; andY is chosen from phenyl, substituted phenyl, C5 heteroaryl, substituted C5 heteroaryl, C6 heteroaryl, and substituted C6 heteroaryl; and R4 is hydrogen.
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16. The compound of claim 15, wherein Y is chosen from phenyl, substituted phenyl, thienyl, substituted thienyl, furyl, substituted furyl, imidazolyl, substituted imidazolyl, thiazole, substituted thiazole, oxazole, substituted oxazole, thiazolidine, substituted thiazolidine, oxazolidine, substituted oxazolidine, oxadiazole, substituted oxadiazole, thiadiazole, substituted thiadiazole, pyridyl, and substituted pyridyl;
- wherein;
each of the one or more substituent groups is independently chosen from halogen, —
OH, —
NH2, —
NO2, —
CN, —
COOH, —
CF3, —
OCF3, C1-4 alkyl, substituted C1-4 alkyl, C1-4 heteroalkyl, and substituted C1-4 heteroalkyl.
- wherein;
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17. The compound of claim 1, wherein the compound is chosen from:
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(3R)-4-amino-3-[4-chloro-3-(phenylcarbonylamino)phenyl]butanoic acid; (3R)-4-amino-3-[2-(3,4-dichlorophenyl)-4-chlorophenyl]butanoic acid; 4-{2-[(1R)-2-amino-1-(carboxymethyl)ethyl]-5-chlorophenyl}benzoic acid; (3R)-4-amino-3-(4-chloro-2-(3-thienyl)phenyl)butanoic acid; (3R)-4-amino-3-[4-chloro-2-(4-chlorophenyl)phenyl]butanoic acid; 2-({5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}amino)benzoic acid; 3-({5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}amino)benzoic acid; 4-({5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}amino)benzoic acid; (3R)-4-amino-3-(4-chloro-2-(3-pyridyl)phenyl)butanoic acid; (3R)-4-amino-3-(4-chloro-2-phenoxyphenyl)butanoic acid; (3R)-4-amino-3-{3-[(3,4-dichlorophenyl)amino]-4-chlorophenyl}butanoic acid; (3R)-4-amino-3-[4-chloro-2-(phenylcarbonyl)phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-2-(2-phenylethyl)phenyl]butanoic acid; (3R)-4-amino-3-[3-({[3-(3,4-dichlorophenoxy)phenyl]methyl}amino)-4-chlorophenyl]butanoic acid; (3R)-4-amino-3-{4-chloro-3-[(2-pyridylmethyl)amino]phenyl}butanoic acid; (3R)-4-amino-3-(4-chloro-3-{[(2-fluorophenyl)methyl]amino}phenyl)butanoic acid; (3R)-4-amino-3-(3-{[(2,4-dichlorophenyl)methyl]amino}-4-chlorophenyl)butanoic acid; (3R)-4-amino-3-(4-chloro-3-{[(3-phenoxyphenyl)methyl]amino}phenyl)butanoic acid; 4-amino-3-[4-chloro-3-(phenylamino)phenyl]butanoic acid; (3R)-4-amino-3-{4-chloro-3-[(3-furylmethyl)amino]phenyl}butanoic acid; (3R)-4-amino-3-{4-chloro-3-[(imidazol-5-ylmethyl)amino]phenyl}butanoic acid; 3-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}benzoic acid; (3R)-4-amino-3-{4-chloro-3-[3-(ethoxycarbonyl)phenyl]phenyl}butanoic acid; (3R)-4-amino-3-(4-chloro-3-(3-pyridyl)phenyl)butanoic acid; (3R)-4-amino-3-[4-chloro-3-(3-cyanophenyl)phenyl]butanoic acid; (3R)-4-amino-3-{3-[3-(carboxymethyl)phenyl]-4-chlorophenyl}butanoic acid; (3R)-4-amino-3-[4-chloro-3-(3-hydroxyphenyl)phenyl]butanoic acid; 3-{3-[(1R)-2-amino-1-(carboxymethyl)ethyl]phenyl}benzoic acid; (3R)-4-amino-3-[4-chloro-3-(3-methoxyphenyl)phenyl]butanoic acid; (3R)-4-amino-3-(3-benzimidazol-6-yl-4-chlorophenyl)butanoic acid; (3R)-4-amino-3-[4-chloro-3-(4-cyanophenyl)phenyl]butanoic acid; (3R)-4-amino-3-[3-(3-carbamoylphenyl)-4-chlorophenyl]butanoic acid; (3R)-4-amino-3-{4-chloro-3-[3-(hydroxymethyl)phenyl]phenyl}butanoic acid; 3-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}-4-chlorobenzoic acid; (3R)-4-amino-3-[4-chloro-3-(3-nitrophenyl)phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(4-nitrophenyl)phenyl]butanoic acid; 5-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}pyridine-3-carboxylic acid; 3-{5-[(1R)-1-(aminomethyl)-3-hydroxypropyl]-2-chlorophenyl}benzenecarbonitrile; 4-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}thiophene-2-carboxylic acid; (3R)-4-amino-3-{4-chloro-3-[(4-pyridylmethyl)amino]phenyl}butanoic acid; (3R)-4-amino-3-[4-chloro-3-(3-methylthiophenyl)phenyl]butanoic acid; (3R)-4-amino-3-{4-chloro-3-[3-(methylsulfonyl)phenyl]phenyl}butanoic acid; 5-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}thiophene-2-carboxylic acid; (3R)-4-amino-3-(4-chloro-3-phenylphenyl)butanoic acid; 3-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}-5-nitrobenzoic acid; (3R)-4-amino-3-[4-chloro-3-(4-chloro-3-cyanophenyl)phenyl]butanoic acid; (3R)-4-amino-3-{3-[3-(dimethylamino)phenyl]-4-chlorophenyl}butanoic acid; 3-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}-5-fluorobenzoic acid; 4-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}-3-chlorobenzoic acid; (3R)-4-amino-3-[4-chloro-3-(4-pyridylmethoxy)phenyl]butanoic acid; (3R)-4-amino-3-{4-chloro-3-[(3-chlorophenyl)carbonylamino]phenyl}butanoic acid; (3R)-4-amino-3-(2-{[(3,4-dichlorophenyl)sulfonyl]amino}-4-chlorophenyl)butanoic acid; (3R)-4-amino-3-{2-[(3,4-dichlorophenyl)carbonylamino]-4-chlorophenyl}butanoic acid; (3R)-4-amino-3-[4-chloro-3-(2-pyridylamino)phenyl]butanoic acid; (3R)-4-amino-3-{4-chloro-3-[(4-methoxyphenyl)amino]phenyl}butanoic acid; (3R)-4-amino-3-[4-chloro-3-(4-pyridylamino)phenyl]butanoic acid; 4-{3-[(1R)-2-amino-1-(carboxymethyl)ethyl]-4-chlorophenoxy}benzoic acid; 3-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenoxy}benzoic acid; (3R)-4-amino-3-(4-chloro-3-phenoxyphenyl)butanoic acid; (3R)-4-amino-3-(3-{[(3,4-dichlorophenyl)sulfonyl]amino}-4-chlorophenyl)butanoic acid; 4-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}benzoic acid; 3-({2-[(1R)-2-amino-1-(carboxymethyl)ethyl]-4-chlorophenyl}hydroxymethyl)benzoic acid; 4-[({5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}amino)methyl]benzoic acid; (3R)-4-amino-3-(4-chloro-3-{[(1-methylimidazol-5-yl)methyl]amino}phenyl) butanoic acid; (3R)-4-amino-3-[4-chloro-3-(5-cyano(2-thienyl))phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(2-methylpyrimidin-5-yl)phenyl]butanoic acid; 5-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}-2-fluorobenzoic acid; (3R)-4-amino-3-[4-chloro-3-(3-cyano-6-methylphenyl)phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(3-cyano-5-fluorophenyl)phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(4-methyl(3-pyridyl))phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(3-cyano-6-fluorophenyl)phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(6-chloro-3-cyanophenyl)phenyl]butanoic acid;
methyl (3R)-4-amino-3-[4-chloro-3-(4-pyridylmethoxy)phenyl]butanoate;(3R)-4-amino-3-[4-chloro-3-(3-pyridylmethoxy)phenyl]butanoic acid; 5-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}furan-3-carboxylic acid; (3R)-4-amino-3-[4-chloro-3-(2-(4-pyridyl)ethoxy)phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(4-pyridylethoxy)phenyl]butanoic acid; (3R)-3-[3-((1R)-1-(4-pyridyl)ethoxy)-4-chlorophenyl]-4-aminobutanoic acid; (3R)-4-amino-3-[4-chloro-3-(5-cyano(3-thienyl))phenyl]butanoic acid; (3R)-4-amino-3-{4-chloro-3-[(2-methyl(4-pyridyl))methoxy]phenyl}butanoic acid; (3R)-4-amino-3-{4-chloro-3-[(3-chloro(4-pyridyl))methoxy]phenyl}butanoic acid; 5-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}thiophene-3-carboxylic acid; (3R)-4-amino-3-[4-chloro-3-(2-(4-pyridyl)ethyl)phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(1,3-thiazol-5-ylmethoxy)phenyl]butanoic acid; (3R)-4-amino-3-{3-[5-(N,N-dimethylcarbamoyl)(2-thienyl)]-4-chlorophenyl}butanoic acid; 2-{4-Chloro-3-(4-pyridylmethoxy)phenyl]-3-(hydrohydroxyphosphoryl)propylamine; 3-{5-[2-amino-1-((hydrohydroxyphosphoryl)methyl)ethyl]-2-chlorophenyl}benzoic acid; (3R)-4-amino-3-{4-chloro-3-[5-(ethoxycarbonyl)(2-thienyl)]phenyl}butanoic acid; and a pharmaceutically acceptable salt of any of the foregoing.
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18. The compound of claim 1, wherein the compound is chosen from:
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3-({5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}amino)benzoic acid; 3-{5-[(1R)-2-Amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}benzoic acid; (3R)-4-amino-3-{4-chloro-3-[(imidazol-5-ylmethyl)amino]phenyl}butanoic acid; (3R)-4-amino-3-(4-chloro-3-(3-pyridyl)phenyl)butanoic acid; (3R)-4-amino-3-[4-chloro-3-(3-cyanophenyl)phenyl]butanoic acid; (3R)-4-amino-3-[3-(3-carbamoylphenyl)-4-chlorophenyl]butanoic acid; 3-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}-4-chlorobenzoic acid; (3R)-4-amino-3-[4-chloro-3-(3-nitrophenyl)phenyl]butanoic acid; 4-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}thiophene-2-carboxylic acid (3R)-4-amino-3-{4-chloro-3-[(4-pyridylmethyl)amino]phenyl}butanoic acid; 5-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}thiophene-2-carboxylic acid; 3-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}-5-fluorobenzoic acid; (3R)-4-amino-3-[4-chloro-3-(4-pyridylmethoxy)phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(5-cyano(2-thienyl))phenyl]butanoic acid; 5-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}-2-fluorobenzoic acid; (3R)-4-amino-3-[4-chloro-3-(3-cyano-6-methylphenyl)phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(3-cyano-5-fluorophenyl)phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(4-methyl(3-pyridyl))phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(3-cyano-6-fluorophenyl)phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(6-chloro-3-cyanophenyl)phenyl]butanoic acid; methyl (3R)-4-amino-3-[4-chloro-3-(4-pyridylmethoxy)phenyl]butanoate; (3R)-4-amino-3-[4-chloro-3-(3-pyridylmethoxy)phenyl]butanoic acid; 5-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}furan-3-carboxylic acid; (3R)-4-amino-3-[4-chloro-3-(2-(4-pyridyl)ethoxy)phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(4-pyridylethoxy)phenyl]butanoic acid; (3R)-3-[3-((1R)-1-(4-pyridyl)ethoxy)-4-chlorophenyl]-4-aminobutanoic acid; (3R)-4-amino-3-[4-chloro-3-(5-cyano(3-thienyl))phenyl]butanoic acid; (3R)-4-amino-3-{4-chloro-3-[(2-methyl(4-pyridyl))methoxy]phenyl}butanoic acid; (3R)-4-amino-3-{4-chloro-3-[(3-chloro(4-pyridyl))methoxy]phenyl}butanoic acid; 5-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}thiophene-3-carboxylic acid; (3R)-4-amino-3-[4-chloro-3-(2-(4-pyridyl)ethyl)phenyl]butanoic acid; (3R)-4-amino-3-[4-chloro-3-(1,3-thiazol-5-ylmethoxy)phenyl]butanoic acid; (3R)-4-amino-3-{3-[5-(N,N-dimethylcarbamoyl)(2-thienyl)]-4-chlorophenyl}butanoic acid; 2-{chloro-3-(4-pyridylmethoxy)phenyl]-3-(hydrohydroxyphosphoryl)propylamine; and a pharmaceutically acceptable salt of any of the foregoing.
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19. The compound of claim 1, wherein the compound exhibits GABAB receptor agonist activity.
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20. The compound of claim 1, wherein the compound exhibits GABAB receptor partial agonist activity.
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21. The compound of claim 1, wherein the compound exhibits GABAB receptor antagonist activity.
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22. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 and a pharmaceutically acceptable vehicle.
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23. The pharmaceutical composition of claim 22, wherein the amount is effective for the treatment of a disease chosen from spasticity, gastro-esophageal reflux disease, emesis, cough, overactive bladder, a substance abuse disorder, an attention disorder, an anxiety disorder, a mood disorder, a cognitive disorder, migraine, and pain.
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24. A method of treating a disease in a patient comprising administering to a patient in need of such treatment the pharmaceutical composition of claim 22, wherein the disease is chosen from spasticity, gastro-esophageal reflux disease, emesis, cough, overactive bladder, a substance abuse disorder, an attention disorder, an anxiety disorder, a mood disorder, a cognitive disorder, migraine, and pain.
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25. A method of modulating GABAB receptor function in a patient comprising administering to a patient a compound of claim 1.
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2. The compound of claim 1, wherein the compound is of Formula (II):
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26. The compound (3R)-4-amino-3-[4-chloro-3-(4-pyridylmethoxy)phenyl]butanoic acid or a pharmaceutically acceptable salt thereof.
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27. The compound 4-{5-[(1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}thiophene-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
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28. The compound 5-15- R1R)-2-amino-1-(carboxymethyl)ethyl]-2-chlorophenyl}thiophene-3-carboxylic acid or a pharmaceutically acceptable salt thereof.
Specification
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Current AssigneeXenoPort, Inc. (Arbor Pharmaceuticals LLC)
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Original AssigneeXenoPort, Inc. (Arbor Pharmaceuticals LLC)
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InventorsXu, Feng, Gallop, Mark A., Peng, Ge, Phan, Thu, Dilip, Usha, Wustrow, David J.
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Primary Examiner(s)ZAREK, PAUL E
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Application NumberUS12/762,152Publication NumberTime in Patent Office991 DaysField of Search514/568, 514/649, 514/751, 564/374, 570/182US Class Current514/568CPC Class CodesA61P 1/00 Drugs for disorders of the ...A61P 1/04 for ulcers, gastritis or re...A61P 1/08 for nausea, cinetosis or ve...A61P 11/00 Drugs for disorders of the ...A61P 11/14 Antitussive agentsA61P 13/10 of the bladderA61P 25/00 Drugs for disorders of the ...A61P 25/04 Centrally acting analgesics...A61P 25/06 Antimigraine agentsA61P 25/20 Hypnotics; SedativesA61P 25/28 for treating neurodegenerat...A61P 25/30 for treating abuse or depen...A61P 43/00 Drugs for specific purposes...C07C 229/34 the carbon skeleton contain...C07C 229/38 having amino groups bound t...C07C 229/42 with carboxyl groups linked...C07C 229/58 having the nitrogen atom of...C07C 229/60 with amino and carboxyl gro...C07C 233/81 having the nitrogen atom of...C07C 237/30 having the nitrogen atom of...C07C 255/58 : containing cyano groups and...C07C 255/59 : the carbon skeleton being f...C07C 311/21 : having the nitrogen atom of...C07C 317/48 : the carbon skeleton being f...C07D 213/30 : Oxygen atomsC07D 213/74 : Amino or imino radicals sub...C07D 333/24 : Radicals substituted by car...C07D 333/70 : attached in position 2C07F 9/301 : Acyclic saturated acids whi...C07F 9/306 : Arylalkanephosphinic acids,...C07F 9/58 : Pyridine rings