CA2439288C - Method for protecting cells and tissues from ionizing radiation toxicity with .alpha.,.beta. unsaturated aryl sulfones - Google Patents

Info

Publication number

CA2439288C

CA2439288C CA2439288A CA2439288A CA2439288C CA 2439288 C CA2439288 C CA 2439288C CA 2439288 A CA2439288 A CA 2439288A CA 2439288 A CA2439288 A CA 2439288A CA 2439288 C CA2439288 C CA 2439288C

Authority

CA

Canada

Prior art keywords

ionizing radiation

radiation

exposure

use according

radioprotective compound

Prior art date

2001-02-28

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

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• 230000005865 ionizing radiation Effects 0.000 title claims abstract description 121
• 125000005362 aryl sulfone group Chemical group 0.000 title abstract description 92
• 230000001988 toxicity Effects 0.000 title abstract description 11
• 231100000419 toxicity Toxicity 0.000 title abstract description 11
• 238000000034 method Methods 0.000 title description 57
• -1 unsaturated aryl sulfone compound Chemical class 0.000 claims abstract description 176
• 230000005855 radiation Effects 0.000 claims abstract description 95
• 230000004223 radioprotective effect Effects 0.000 claims abstract description 64
• 230000000694 effects Effects 0.000 claims abstract description 31
• 150000001875 compounds Chemical class 0.000 claims description 103
• 125000003118 aryl group Chemical group 0.000 claims description 39
• 210000001185 bone marrow Anatomy 0.000 claims description 37
• 238000011282 treatment Methods 0.000 claims description 37
• 230000001225 therapeutic effect Effects 0.000 claims description 28
• 230000006378 damage Effects 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 24
• 206010028980 Neoplasm Diseases 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• SNGZRCQJDGCGEF-OGBZJDJUSA-N 4-[(e)-3-[(e)-3-(4-carboxyphenyl)-1-(4-chlorophenyl)prop-2-enyl]sulfonyl-3-(4-chlorophenyl)prop-1-enyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C=CC(=CC=1)C(O)=O)C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 SNGZRCQJDGCGEF-OGBZJDJUSA-N 0.000 claims description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• 230000002062 proliferating effect Effects 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 14
• 201000011510 cancer Diseases 0.000 claims description 13
• 230000003211 malignant effect Effects 0.000 claims description 13
• 125000001424 substituent group Chemical group 0.000 claims description 12
• LRHCIAKITMHSNT-OGBZJDJUSA-N 1-[(e)-3-(4-chlorophenyl)-3-[(e)-1-(4-chlorophenyl)-3-(4-fluorophenyl)prop-2-enyl]sulfonylprop-1-enyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C=CC(F)=CC=1)C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 LRHCIAKITMHSNT-OGBZJDJUSA-N 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 10
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 6
• XHHUIUHBUNSNOW-LQGKIZFRSA-N 4-[(e)-1-[(e)-1-(4-cyanophenyl)-3-(4-fluorophenyl)prop-2-enyl]sulfonyl-3-(4-fluorophenyl)prop-2-enyl]benzonitrile Chemical compound C1=CC(F)=CC=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C=CC(F)=CC=1)C=1C=CC(=CC=1)C#N)C1=CC=C(C#N)C=C1 XHHUIUHBUNSNOW-LQGKIZFRSA-N 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• LSQPHWBCMFQPAP-XPWSMXQVSA-N 1,3,5-trimethoxy-2-[(e)-3-(4-methoxyphenyl)-3-[(e)-1-(4-methoxyphenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-enyl]sulfonylprop-1-enyl]benzene Chemical compound C1=CC(OC)=CC=C1C(S(=O)(=O)C(\C=C\C=1C(=CC(OC)=CC=1OC)OC)C=1C=CC(OC)=CC=1)\C=C\C1=C(OC)C=C(OC)C=C1OC LSQPHWBCMFQPAP-XPWSMXQVSA-N 0.000 claims description 3
• LRHCIAKITMHSNT-FDWQPRGYSA-N 1-[(z)-3-(4-chlorophenyl)-3-[(z)-1-(4-chlorophenyl)-3-(4-fluorophenyl)prop-2-enyl]sulfonylprop-1-enyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1\C=C/C(S(=O)(=O)C(\C=C/C=1C=CC(F)=CC=1)C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 LRHCIAKITMHSNT-FDWQPRGYSA-N 0.000 claims description 3
• PTXRVHYRFPXJKU-OGBZJDJUSA-N 1-fluoro-4-[(e)-3-[(e)-3-(4-fluorophenyl)-1-[4-(trifluoromethyl)phenyl]prop-2-enyl]sulfonyl-3-[4-(trifluoromethyl)phenyl]prop-1-enyl]benzene Chemical compound C1=CC(F)=CC=C1\C=C\C(S(=O)(=O)C(\C=C\C=1C=CC(F)=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 PTXRVHYRFPXJKU-OGBZJDJUSA-N 0.000 claims description 3
• ARXGEFCQNAWAPD-FACPPWRESA-N 4-chloro-1-[4-chloro-2-[(e)-2-(4-fluorophenyl)ethenyl]phenyl]sulfonyl-2-[(e)-2-(4-fluorophenyl)ethenyl]benzene Chemical compound C1=CC(F)=CC=C1\C=C\C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1\C=C\C1=CC=C(F)C=C1 ARXGEFCQNAWAPD-FACPPWRESA-N 0.000 claims description 3
• GUTQOTUHJUKDRX-FARFLWGWSA-N C(=C/C1=CC=CC=C1)/C(=CC1=C(C=C(C=C1)OCC)OC)/S(=O)(=O)C(=CC1=C(C=C(C=C1)OCC)OC)C=C/C1=CC=CC=C1 Chemical compound C(=C/C1=CC=CC=C1)/C(=CC1=C(C=C(C=C1)OCC)OC)/S(=O)(=O)C(=CC1=C(C=C(C=C1)OCC)OC)C=C/C1=CC=CC=C1 GUTQOTUHJUKDRX-FARFLWGWSA-N 0.000 claims description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 125000001041 indolyl group Chemical group 0.000 claims description 2
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
• 125000002971 oxazolyl group Chemical group 0.000 claims description 2
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• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
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• 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
• 125000001544 thienyl group Chemical group 0.000 claims description 2
• 125000003107 substituted aryl group Chemical group 0.000 claims 5
• 230000000246 remedial effect Effects 0.000 claims 1
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