RU2568611C2 - Средства, индуцирующие апоптоз, для лечения рака, иммунных и аутоиммунных заболеваний - Google Patents

Info

Publication number

RU2568611C2

RU2568611C2 RU2012145298/04A RU2012145298A RU2568611C2 RU 2568611 C2 RU2568611 C2 RU 2568611C2 RU 2012145298/04 A RU2012145298/04 A RU 2012145298/04A RU 2012145298 A RU2012145298 A RU 2012145298A RU 2568611 C2 RU2568611 C2 RU 2568611C2

Authority

RU

Russia

Prior art keywords

amino

phenyl

sulfonyl

benzamide

ylmethyl

Prior art date

2010-03-25

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• 206010028980 Neoplasm Diseases 0.000 title claims description 43
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• 208000023275 Autoimmune disease Diseases 0.000 title description 5
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• 230000001939 inductive effect Effects 0.000 title 1
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• -1 tetrahydro-2H-pyran-4-yl Chemical group 0.000 claims abstract description 523
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
• 239000003814 drug Substances 0.000 claims abstract description 34
• 108010090931 Proto-Oncogene Proteins c-bcl-2 Proteins 0.000 claims abstract description 30
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• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims abstract description 12
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• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 256
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 81
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
• 238000000034 method Methods 0.000 claims description 39
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
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• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 10
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• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• LUQVCHRDAGWYMG-UHFFFAOYSA-N 4-phenylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC=C1 LUQVCHRDAGWYMG-UHFFFAOYSA-N 0.000 claims description 5
• 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 4
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• TZURUFLUONRNJW-UHFFFAOYSA-N 7,7-dimethyl-3-[2-[[4-[4-[[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylcarbamoyl]phenyl]piperazin-1-yl]methyl]phenyl]bicyclo[2.2.1]hept-2-ene-4-carboxylic acid Chemical compound CC1(C)C(C=2)CCC1(C(O)=O)C=2C1=CC=CC=C1CN(CC1)CCN1C(C=C1)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCOCC1 TZURUFLUONRNJW-UHFFFAOYSA-N 0.000 claims description 2
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• 239000003112 inhibitor Substances 0.000 abstract description 32
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• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract description 3
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• 230000004952 protein activity Effects 0.000 abstract 2
• HPTSBCGYASZMOB-UHFFFAOYSA-N 4-[4-(1-adamantylmethyl)piperazin-1-yl]-n-[4-(cyclohexylmethylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C=CC(=CC=2)N2CCN(CC34CC5CC(CC(C5)C3)C4)CC2)=CC=C1NCC1CCCCC1 HPTSBCGYASZMOB-UHFFFAOYSA-N 0.000 abstract 1
• BSUGSMPDCLDVJU-UHFFFAOYSA-N 4-[4-[2-(1-adamantyl)-2-oxoethyl]piperazin-1-yl]-n-[4-(cyclohexylmethylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C=CC(=CC=2)N2CCN(CC(=O)C34CC5CC(CC(C5)C3)C4)CC2)=CC=C1NCC1CCCCC1 BSUGSMPDCLDVJU-UHFFFAOYSA-N 0.000 abstract 1
• UYHFACZDUCOLME-UHFFFAOYSA-N 4-[4-[[2-[5-(8-azabicyclo[3.2.1]octan-8-ylmethyl)thiophen-2-yl]phenyl]methyl]piperazin-1-yl]-n-[3-nitro-4-(oxan-4-ylmethylamino)phenyl]sulfonylbenzamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC(=O)C=2C=CC(=CC=2)N2CCN(CC=3C(=CC=CC=3)C=3SC(CN4C5CCC4CCC5)=CC=3)CC2)=CC=C1NCC1CCOCC1 UYHFACZDUCOLME-UHFFFAOYSA-N 0.000 abstract 1
• INWFGWCWCQKFSZ-OJGIYMQYSA-N 4-[4-[acetyl-[(1r,3s,4s,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]amino]piperidin-1-yl]-n-[4-(cyclohexylmethylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound CC(=O)N([C@@H]1[C@@H](C)[C@@]2(C[C@](C1)(C2(C)C)[H])[H])C(CC1)CCN1C(C=C1)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCCCC1 INWFGWCWCQKFSZ-OJGIYMQYSA-N 0.000 abstract 1
• ITRZAMXRMUCJTB-CVLZCZDBSA-N 4-[4-[benzoyl-[(1r,3s,4s,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]amino]piperidin-1-yl]-n-[4-(cyclohexylmethylamino)-3-nitrophenyl]sulfonylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N([C@@H]1[C@@H](C)[C@@]2(C[C@](C1)(C2(C)C)[H])[H])C(CC1)CCN1C(C=C1)=CC=C1C(=O)NS(=O)(=O)C(C=C1[N+]([O-])=O)=CC=C1NCC1CCCCC1 ITRZAMXRMUCJTB-CVLZCZDBSA-N 0.000 abstract 1
• 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 abstract 1
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