UA79507C2 - Purine compounds and uses thereof as cannabinoid receptor ligands - Google Patents
Purine compounds and uses thereof as cannabinoid receptor ligands Download PDFInfo
- Publication number
- UA79507C2 UA79507C2 UAA200504047A UA2005004047A UA79507C2 UA 79507 C2 UA79507 C2 UA 79507C2 UA A200504047 A UAA200504047 A UA A200504047A UA 2005004047 A UA2005004047 A UA 2005004047A UA 79507 C2 UA79507 C2 UA 79507C2
- Authority
- UA
- Ukraine
- Prior art keywords
- alkyl
- alkylamino
- partially
- aryl
- heteroaryl
- Prior art date
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- 102000018208 Cannabinoid Receptor Human genes 0.000 title abstract description 19
- 108050007331 Cannabinoid receptor Proteins 0.000 title abstract description 19
- 239000003446 ligand Substances 0.000 title abstract description 14
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 383
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 41
- 238000011282 treatment Methods 0.000 claims abstract description 38
- 241001465754 Metazoa Species 0.000 claims abstract description 29
- 201000010099 disease Diseases 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 314
- 125000003282 alkyl amino group Chemical group 0.000 claims description 181
- 229920006395 saturated elastomer Polymers 0.000 claims description 175
- -1 cyano, hydroxy, amino Chemical group 0.000 claims description 169
- 125000003118 aryl group Chemical group 0.000 claims description 154
- 125000001072 heteroaryl group Chemical group 0.000 claims description 146
- 239000001257 hydrogen Substances 0.000 claims description 138
- 229910052739 hydrogen Inorganic materials 0.000 claims description 138
- 125000000623 heterocyclic group Chemical group 0.000 claims description 136
- 239000000203 mixture Substances 0.000 claims description 112
- 239000000126 substance Substances 0.000 claims description 106
- 238000000034 method Methods 0.000 claims description 105
- 125000002252 acyl group Chemical group 0.000 claims description 91
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 81
- 150000002431 hydrogen Chemical class 0.000 claims description 77
- 150000003839 salts Chemical class 0.000 claims description 75
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 44
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 43
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
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- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 claims description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- MZRPLPNMEBKVMW-UHFFFAOYSA-N 6-(1-benzylpyrrolidin-3-yl)oxy-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)purine Chemical compound C1=CC(Cl)=CC=C1N1C2=NC=NC(OC3CN(CC=4C=CC=CC=4)CC3)=C2N=C1C1=CC=C(Cl)C=C1Cl MZRPLPNMEBKVMW-UHFFFAOYSA-N 0.000 claims description 2
- VNOGOEOTNFURPS-UHFFFAOYSA-N 9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-6-(4-pyrimidin-2-ylpiperazin-1-yl)purine Chemical compound C1=CC(Cl)=CC=C1N1C2=NC=NC(N3CCN(CC3)C=3N=CC=CN=3)=C2N=C1C1=CC=C(Cl)C=C1Cl VNOGOEOTNFURPS-UHFFFAOYSA-N 0.000 claims description 2
- MOMMTIGOEFZQSC-UHFFFAOYSA-N 9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-6-propan-2-yloxypurine Chemical compound N=1C=2C(OC(C)C)=NC=NC=2N(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1Cl MOMMTIGOEFZQSC-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- RYVNIFSIEDRLSJ-UHFFFAOYSA-N 5-(hydroxymethyl)cytosine Chemical compound NC=1NC(=O)N=CC=1CO RYVNIFSIEDRLSJ-UHFFFAOYSA-N 0.000 claims 1
- HDPLEFUIDWOLLX-UHFFFAOYSA-N 9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-6-(4-pyridin-2-ylpiperazin-1-yl)purine Chemical compound C1=CC(Cl)=CC=C1N1C2=NC=NC(N3CCN(CC3)C=3N=CC=CC=3)=C2N=C1C1=CC=C(Cl)C=C1Cl HDPLEFUIDWOLLX-UHFFFAOYSA-N 0.000 claims 1
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