MXPA03008229A - Trienos fluorados y su uso como moduladores rxr. - Google Patents

Info

Publication number

MXPA03008229A

MXPA03008229A MXPA03008229A MXPA03008229A MXPA03008229A MX PA03008229 A MXPA03008229 A MX PA03008229A MX PA03008229 A MXPA03008229 A MX PA03008229A MX PA03008229 A MXPA03008229 A MX PA03008229A MX PA03008229 A MXPA03008229 A MX PA03008229A

Authority

MX

Mexico

Prior art keywords

optionally substituted

alkyl

aryl

independently

methyl

Prior art date

2001-03-14

Links

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• 150000005671 trienes Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 243
• 102000034527 Retinoid X Receptors Human genes 0.000 claims abstract description 111
• 108010038912 Retinoid X Receptors Proteins 0.000 claims abstract description 111
• 238000000034 method Methods 0.000 claims abstract description 92
• 230000000694 effects Effects 0.000 claims abstract description 64
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 37
• 241000124008 Mammalia Species 0.000 claims abstract description 30
• -1 2, 2-difluoroethoxy Chemical group 0.000 claims description 171
• 239000002253 acid Substances 0.000 claims description 105
• 125000003118 aryl group Chemical group 0.000 claims description 76
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 74
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
• 150000003839 salts Chemical class 0.000 claims description 56
• 125000001072 heteroaryl group Chemical group 0.000 claims description 45
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 44
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 39
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 38
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 38
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 36
• 239000012453 solvate Substances 0.000 claims description 33
• 150000004677 hydrates Chemical class 0.000 claims description 31
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
• 125000000623 heterocyclic group Chemical group 0.000 claims description 30
• 125000004104 aryloxy group Chemical group 0.000 claims description 29
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 29
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 28
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 125000005907 alkyl ester group Chemical group 0.000 claims description 25
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 24
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 23
• 125000001153 fluoro group Chemical group F* 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 22
• 239000000833 heterodimer Substances 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
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• 125000002837 carbocyclic group Chemical group 0.000 claims description 17
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• 125000005843 halogen group Chemical group 0.000 claims description 15
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• 101150050070 RXRA gene Proteins 0.000 claims description 14
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• 125000003277 amino group Chemical group 0.000 claims description 14
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• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 10
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• 239000003638 chemical reducing agent Substances 0.000 claims description 7
• ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 claims description 7
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• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 claims description 6
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• OKUYZZYPRLAUJW-UHFFFAOYSA-N CC(C)=C(C(O)=O)P(=O)=O Chemical compound CC(C)=C(C(O)=O)P(=O)=O OKUYZZYPRLAUJW-UHFFFAOYSA-N 0.000 claims description 5
• LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 claims description 5
• 229960000956 coumarin Drugs 0.000 claims description 5
• 235000001671 coumarin Nutrition 0.000 claims description 5
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 5
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• 229910052744 lithium Inorganic materials 0.000 claims description 5
• 102000027483 retinoid hormone receptors Human genes 0.000 claims description 5
• 108091008679 retinoid hormone receptors Proteins 0.000 claims description 5
• PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims description 5
• VUOSOCHNOBGHIQ-GPSVRZEVSA-N (2e,4e,6z)-7-[2-butoxy-3,5-di(propan-2-yl)phenyl]-3-(trifluoromethyl)octa-2,4,6-trienoic acid Chemical compound CCCCOC1=C(C(C)C)C=C(C(C)C)C=C1\C(C)=C/C=C/C(=C\C(O)=O)/C(F)(F)F VUOSOCHNOBGHIQ-GPSVRZEVSA-N 0.000 claims description 4
• VUOSOCHNOBGHIQ-BFJYOHIJSA-N (2z,4e,6z)-7-[2-butoxy-3,5-di(propan-2-yl)phenyl]-3-(trifluoromethyl)octa-2,4,6-trienoic acid Chemical compound CCCCOC1=C(C(C)C)C=C(C(C)C)C=C1\C(C)=C/C=C/C(=C/C(O)=O)/C(F)(F)F VUOSOCHNOBGHIQ-BFJYOHIJSA-N 0.000 claims description 4
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• XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 4
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• BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 claims description 4
• 150000003254 radicals Chemical class 0.000 claims description 4
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