DK2627649T3 - CXCR4 receptor antagonists - Google Patents

Info

Publication number

DK2627649T3

DK2627649T3 DK11773227.1T DK11773227T DK2627649T3 DK 2627649 T3 DK2627649 T3 DK 2627649T3 DK 11773227 T DK11773227 T DK 11773227T DK 2627649 T3 DK2627649 T3 DK 2627649T3

Authority

DK

Denmark

Prior art keywords

piperidin

pyridin

diazepan

pyridine

propan

Prior art date

2010-10-14

Links

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• 108010061299 CXCR4 Receptors Proteins 0.000 title description 10
• 102000012000 CXCR4 Receptors Human genes 0.000 title description 10
• 239000002464 receptor antagonist Substances 0.000 title 1
• 229940044551 receptor antagonist Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 354
• -1 isopropylmethyl Chemical group 0.000 claims description 195
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 170
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 138
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 101
• 125000000217 alkyl group Chemical group 0.000 claims description 73
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 64
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
• 125000001424 substituent group Chemical group 0.000 claims description 44
• 125000001153 fluoro group Chemical group F* 0.000 claims description 42
• 210000000130 stem cell Anatomy 0.000 claims description 41
• 206010028980 Neoplasm Diseases 0.000 claims description 39
• 238000011282 treatment Methods 0.000 claims description 38
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 36
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims description 34
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 210000004027 cell Anatomy 0.000 claims description 25
• 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims description 24
• 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 23
• 150000002367 halogens Chemical class 0.000 claims description 23
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
• 238000000034 method Methods 0.000 claims description 22
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 21
• 201000011510 cancer Diseases 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 21
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 16
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• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
• 229910052731 fluorine Inorganic materials 0.000 claims description 16
• 239000011737 fluorine Substances 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 15
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• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 238000001959 radiotherapy Methods 0.000 claims description 13
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• 125000003118 aryl group Chemical group 0.000 claims description 12
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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 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
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• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 7
• 125000001041 indolyl group Chemical group 0.000 claims description 7
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• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
• FUFZNHHSSMCXCZ-UHFFFAOYSA-N 5-piperidin-4-yl-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical group FC(F)(F)C1=CC=CC(C=2N=C(ON=2)C2CCNCC2)=C1 FUFZNHHSSMCXCZ-UHFFFAOYSA-N 0.000 claims description 3
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• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 230000009467 reduction Effects 0.000 claims description 3
• UUCZFULDFFWPQL-TZIWHRDSSA-N (3r)-n-[[(3r)-1-cyclopentylpyrrolidin-3-yl]methyl]-1-[6-(4-cyclopropyl-5-methyl-1h-imidazol-2-yl)pyridin-2-yl]pyrrolidin-3-amine Chemical compound CC=1NC(C=2N=C(C=CC=2)N2C[C@@H](CC2)NC[C@@H]2CN(CC2)C2CCCC2)=NC=1C1CC1 UUCZFULDFFWPQL-TZIWHRDSSA-N 0.000 claims description 2
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