CA2577046A1 - Chemokine combinations to mobilize progenitor/stem cells - Google Patents

Info

Publication number

CA2577046A1

CA2577046A1 CA002577046A CA2577046A CA2577046A1 CA 2577046 A1 CA2577046 A1 CA 2577046A1 CA 002577046 A CA002577046 A CA 002577046A CA 2577046 A CA2577046 A CA 2577046A CA 2577046 A1 CA2577046 A1 CA 2577046A1

Authority

CA

Canada

Prior art keywords

pyridinylmethyl

tetrahydro

methyl

methylene

ring

Prior art date

2004-08-13

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 210000000130 stem cell Anatomy 0.000 title claims abstract description 89
• 102000019034 Chemokines Human genes 0.000 title description 11
• 108010012236 Chemokines Proteins 0.000 title description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 96
• 238000000034 method Methods 0.000 claims abstract description 88
• 125000003118 aryl group Chemical group 0.000 claims description 69
• 229910052757 nitrogen Inorganic materials 0.000 claims description 64
• 125000000623 heterocyclic group Chemical group 0.000 claims description 53
• 229940121384 cxc chemokine receptor type 4 (cxcr4) antagonist Drugs 0.000 claims description 41
• 239000002576 chemokine receptor CXCR4 antagonist Substances 0.000 claims description 36
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 35
• 125000004122 cyclic group Chemical group 0.000 claims description 32
• 125000005842 heteroatom Chemical group 0.000 claims description 32
• 150000003839 salts Chemical group 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 26
• 102000004169 proteins and genes Human genes 0.000 claims description 22
• 108090000623 proteins and genes Proteins 0.000 claims description 22
• 229940002612 prodrug Drugs 0.000 claims description 19
• 239000000651 prodrug Chemical group 0.000 claims description 19
• 210000001185 bone marrow Anatomy 0.000 claims description 17
• 210000005259 peripheral blood Anatomy 0.000 claims description 17
• 239000011886 peripheral blood Substances 0.000 claims description 17
• 125000002947 alkylene group Chemical group 0.000 claims description 14
• 229920000768 polyamine Polymers 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 125000002950 monocyclic group Chemical group 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 10
• 125000005647 linker group Chemical group 0.000 claims description 9
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 8
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• 125000000468 ketone group Chemical group 0.000 claims description 2
• WVLHHLRVNDMIAR-UHFFFAOYSA-N n'-(1h-benzimidazol-2-ylmethyl)-n'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine Chemical compound C1CCC2=CC=CN=C2C1N(CCCCN)CC1=NC2=CC=CC=C2N1 WVLHHLRVNDMIAR-UHFFFAOYSA-N 0.000 claims description 2
• CWJJHESJXJQCJA-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-1-[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methanamine Chemical compound C=1C=C(CN2CCNCCCNCCNCCC2)C=CC=1CNCC1=CC=CC=N1 CWJJHESJXJQCJA-UHFFFAOYSA-N 0.000 claims description 2
• RTHCDPLDSUOFCC-UHFFFAOYSA-N n-(pyridin-4-ylmethyl)-1-[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methanamine Chemical compound C=1C=NC=CC=1CNCC(C=C1)=CC=C1CN1CCCNCCNCCCNCC1 RTHCDPLDSUOFCC-UHFFFAOYSA-N 0.000 claims description 2
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• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
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• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
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• TWTLJZJKDUYSON-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)-1-[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methanamine Chemical compound C=1C=C(CN2CCNCCCNCCNCCC2)C=CC=1CNCC1=CC=CN=C1 TWTLJZJKDUYSON-UHFFFAOYSA-N 0.000 claims 1
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• -1 AMD3 100 Chemical class 0.000 description 71
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 55
• 125000000217 alkyl group Chemical group 0.000 description 47
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 41
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 39
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• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 23
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 22
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 21
• YIQPUIGJQJDJOS-UHFFFAOYSA-N plerixafor Chemical compound C=1C=C(CN2CCNCCCNCCNCCC2)C=CC=1CN1CCCNCCNCCCNCC1 YIQPUIGJQJDJOS-UHFFFAOYSA-N 0.000 description 21
• 125000005843 halogen group Chemical group 0.000 description 20
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
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• 125000001424 substituent group Chemical group 0.000 description 19
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 18
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 18
• 125000003342 alkenyl group Chemical group 0.000 description 18
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
• 229920006395 saturated elastomer Polymers 0.000 description 17
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
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• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 14
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 14
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• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 14
• 229910052739 hydrogen Inorganic materials 0.000 description 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 12
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 12
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• 125000004093 cyano group Chemical group *C#N 0.000 description 11
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