CA2555313A1

CA2555313A1 - Heparanase inhibitors and uses thereof

Heparanase inhibitors and uses thereof Download PDF

Info

Publication number: CA2555313A1
Authority: CA; Canada
Prior art keywords: alkyl; nr9r; group; aryl; compound
Prior art date: 2004-02-06
Legal status : Abandoned

Application number

CA002555313A

Other languages

English (en)

French (fr)

Inventor

Joel M. Van Gelder

Yochai Basel

Boris O. Kraiz

Orly Mouallem

Daphna Miron

Nina Gur-Arie

Joseph Klein

Current Assignee

Insight Biopharmaceuticals Ltd

Original Assignee

Individual

Priority date

2004-02-06

Filing date

2005-02-06

Publication date

2005-08-18

2005-02-06 Application filed by Individual filed Critical Individual

2005-08-18 Publication of CA2555313A1 publication Critical patent/CA2555313A1/en

Status Abandoned legal-status Critical Current

Links

108010037536 heparanase Proteins 0.000 title claims abstract description 98
102100024025 Heparanase Human genes 0.000 title claims abstract description 93
239000003112 inhibitor Substances 0.000 title abstract description 29
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230000003197 catalytic effect Effects 0.000 claims abstract description 18
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 15
208000037765 diseases and disorders Diseases 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 394
125000000217 alkyl group Chemical group 0.000 claims description 340
125000005915 C6-C14 aryl group Chemical group 0.000 claims description 167
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 143
150000003254 radicals Chemical class 0.000 claims description 136
239000008194 pharmaceutical composition Substances 0.000 claims description 125
229910052717 sulfur Inorganic materials 0.000 claims description 123
229910052736 halogen Inorganic materials 0.000 claims description 120
125000004433 nitrogen atom Chemical group N* 0.000 claims description 120
150000002367 halogens Chemical class 0.000 claims description 118
229910052757 nitrogen Inorganic materials 0.000 claims description 118
125000003342 alkenyl group Chemical group 0.000 claims description 106
229910052760 oxygen Inorganic materials 0.000 claims description 89
229910052739 hydrogen Inorganic materials 0.000 claims description 83
210000004027 cell Anatomy 0.000 claims description 73
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 70
239000004593 Epoxy Substances 0.000 claims description 66
229910006069 SO3H Inorganic materials 0.000 claims description 62
239000000203 mixture Substances 0.000 claims description 60
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
238000002360 preparation method Methods 0.000 claims description 58
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125000005842 heteroatom Chemical group 0.000 claims description 55
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 53
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 51
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125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 48
239000007787 solid Substances 0.000 claims description 42
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 14
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XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 14
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 14
239000010452 phosphate Substances 0.000 claims description 14
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QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 13
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