CA2523045A1 - Composes phosphonates anti-inflammatoires - Google Patents

Info

Publication number

CA2523045A1

CA2523045A1 CA 2523045 CA2523045A CA2523045A1 CA 2523045 A1 CA2523045 A1 CA 2523045A1 CA 2523045 CA2523045 CA 2523045 CA 2523045 A CA2523045 A CA 2523045A CA 2523045 A1 CA2523045 A1 CA 2523045A1

Authority

CA

Canada

Prior art keywords

conjugate

compound

formula

groups

independently

Prior art date

2003-04-25

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

• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title claims description 35
• 230000003110 anti-inflammatory effect Effects 0.000 title claims description 35
• 150000001875 compounds Chemical class 0.000 claims description 443
• -1 cyano, methyl Chemical group 0.000 claims description 423
• 238000000034 method Methods 0.000 claims description 200
• 229910052760 oxygen Inorganic materials 0.000 claims description 122
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 116
• 229910052757 nitrogen Inorganic materials 0.000 claims description 104
• 125000004432 carbon atom Chemical group C* 0.000 claims description 82
• 229940024606 amino acid Drugs 0.000 claims description 60
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
• 125000006239 protecting group Chemical group 0.000 claims description 59
• 125000000217 alkyl group Chemical group 0.000 claims description 57
• 150000001413 amino acids Chemical class 0.000 claims description 47
• 125000003118 aryl group Chemical group 0.000 claims description 43
• 150000003839 salts Chemical class 0.000 claims description 41
• 229910052717 sulfur Inorganic materials 0.000 claims description 41
• 125000000623 heterocyclic group Chemical group 0.000 claims description 40
• 239000003814 drug Substances 0.000 claims description 38
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 38
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
• 125000005647 linker group Chemical group 0.000 claims description 35
• 229910052731 fluorine Inorganic materials 0.000 claims description 34
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• 229940079593 drug Drugs 0.000 claims description 33
• 229910052799 carbon Inorganic materials 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 24
• 125000003342 alkenyl group Chemical group 0.000 claims description 23
• 125000005843 halogen group Chemical group 0.000 claims description 23
• 125000005842 heteroatom Chemical group 0.000 claims description 23
• 125000001424 substituent group Chemical group 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 229910052740 iodine Inorganic materials 0.000 claims description 19
• 229910052794 bromium Inorganic materials 0.000 claims description 17
• 229910052801 chlorine Inorganic materials 0.000 claims description 17
• 206010061218 Inflammation Diseases 0.000 claims description 16
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
• 230000004054 inflammatory process Effects 0.000 claims description 16
• 125000002947 alkylene group Chemical group 0.000 claims description 15
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 125000004450 alkenylene group Chemical group 0.000 claims description 13
• 125000004419 alkynylene group Chemical group 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
• 238000011282 treatment Methods 0.000 claims description 13
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
• 125000004423 acyloxy group Chemical group 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• 150000003254 radicals Chemical class 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
• BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 10
• 238000001727 in vivo Methods 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 10
• 241001465754 Metazoa Species 0.000 claims description 9
• 101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 claims description 8
• 239000004615 ingredient Substances 0.000 claims description 8
• 239000002777 nucleoside Substances 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 229960004441 tyrosine Drugs 0.000 claims description 7
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 6
• 150000002430 hydrocarbons Chemical group 0.000 claims description 6
• 238000000338 in vitro Methods 0.000 claims description 6
• 239000003112 inhibitor Substances 0.000 claims description 6
• 239000012453 solvate Substances 0.000 claims description 6
• 229920002554 vinyl polymer Polymers 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 4
• AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 4
• 239000004473 Threonine Substances 0.000 claims description 4
• 229960005261 aspartic acid Drugs 0.000 claims description 4
• 239000002552 dosage form Substances 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• 229960002885 histidine Drugs 0.000 claims description 4
• 230000002757 inflammatory effect Effects 0.000 claims description 4
• 229960002898 threonine Drugs 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
• 150000003833 nucleoside derivatives Chemical class 0.000 claims description 3
• 125000004437 phosphorous atom Chemical group 0.000 claims description 3
• ALBODLTZUXKBGZ-JUUVMNCLSA-N (2s)-2-amino-3-phenylpropanoic acid;(2s)-2,6-diaminohexanoic acid Chemical compound NCCCC[C@H](N)C(O)=O.OC(=O)[C@@H](N)CC1=CC=CC=C1 ALBODLTZUXKBGZ-JUUVMNCLSA-N 0.000 claims description 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
• 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 229940123827 Purine nucleoside phosphorylase inhibitor Drugs 0.000 claims description 2
• IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
• 230000002924 anti-infective effect Effects 0.000 claims description 2
• 230000000340 anti-metabolite Effects 0.000 claims description 2
• 229940100197 antimetabolite Drugs 0.000 claims description 2
• 239000002256 antimetabolite Substances 0.000 claims description 2
• 239000002246 antineoplastic agent Substances 0.000 claims description 2
• 239000003443 antiviral agent Substances 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
• 229940043355 kinase inhibitor Drugs 0.000 claims description 2
• 230000001404 mediated effect Effects 0.000 claims description 2
• 238000013160 medical therapy Methods 0.000 claims description 2
• 208000030159 metabolic disease Diseases 0.000 claims description 2
• 125000004043 oxo group Chemical group O=* 0.000 claims description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 2
• 229920000729 poly(L-lysine) polymer Polymers 0.000 claims description 2
• 229920002643 polyglutamic acid Polymers 0.000 claims description 2
• 108010050934 polyleucine Proteins 0.000 claims description 2
• 108010055896 polyornithine Proteins 0.000 claims description 2
• 108010000222 polyserine Proteins 0.000 claims description 2
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
• 239000000784 purine nucleoside phosphorylase inhibitor Substances 0.000 claims description 2
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
• CKLJMWTZIZZHCS-UWTATZPHSA-N D-aspartic acid Chemical compound OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims 1
• 125000002993 cycloalkylene group Chemical group 0.000 claims 1
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
• 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 131
• 238000006243 chemical reaction Methods 0.000 description 127
• 239000000047 product Substances 0.000 description 127
• 239000000203 mixture Substances 0.000 description 93
• 238000003786 synthesis reaction Methods 0.000 description 71
• 230000015572 biosynthetic process Effects 0.000 description 68
• 150000002148 esters Chemical class 0.000 description 60
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
• 235000001014 amino acid Nutrition 0.000 description 58
• 239000000651 prodrug Substances 0.000 description 58
• 229940002612 prodrug Drugs 0.000 description 58
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 53
• 239000002904 solvent Substances 0.000 description 53
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 49
• 238000002360 preparation method Methods 0.000 description 49
• 239000000543 intermediate Substances 0.000 description 47
• 239000004480 active ingredient Substances 0.000 description 46
• 239000002253 acid Substances 0.000 description 45
• 239000002585 base Substances 0.000 description 45
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 44
• 239000000243 solution Substances 0.000 description 41
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 40
• 239000003153 chemical reaction reagent Substances 0.000 description 37
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
• 102000004196 processed proteins & peptides Human genes 0.000 description 34
• 238000009472 formulation Methods 0.000 description 33
• 150000001412 amines Chemical class 0.000 description 31
• 229920001184 polypeptide Polymers 0.000 description 30
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
• 210000004027 cell Anatomy 0.000 description 28
• 125000003710 aryl alkyl group Chemical group 0.000 description 27
• 150000005690 diesters Chemical class 0.000 description 27
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 26
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
• 238000005859 coupling reaction Methods 0.000 description 26
• 150000001408 amides Chemical class 0.000 description 25
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
• FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
• 239000000460 chlorine Substances 0.000 description 22
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 20
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• 125000000524 functional group Chemical group 0.000 description 20
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• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
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• 239000012071 phase Substances 0.000 description 16
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
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• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 15
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 14
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• 125000006413 ring segment Chemical group 0.000 description 14
• QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 14
• 239000000126 substance Substances 0.000 description 14
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 13
• 239000007821 HATU Substances 0.000 description 13
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