AU2004269020A1 - Substituted isoquinoline derivatives and methods of use - Google Patents

Info

Publication number

AU2004269020A1

AU2004269020A1 AU2004269020A AU2004269020A AU2004269020A1 AU 2004269020 A1 AU2004269020 A1 AU 2004269020A1 AU 2004269020 A AU2004269020 A AU 2004269020A AU 2004269020 A AU2004269020 A AU 2004269020A AU 2004269020 A1 AU2004269020 A1 AU 2004269020A1

Authority

AU

Australia

Prior art keywords

optionally substituted

piperidin

substituted

ylmethoxy

boc

Prior art date

2003-08-25

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
• Discuss

• 238000000034 method Methods 0.000 title claims abstract description 64
• 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 266
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 39
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 39
• 150000003839 salts Chemical class 0.000 claims abstract description 37
• 238000011282 treatment Methods 0.000 claims abstract description 34
• 230000033115 angiogenesis Effects 0.000 claims abstract description 21
• 201000011510 cancer Diseases 0.000 claims abstract description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• -1 -OR 3 Chemical group 0.000 claims description 1091
• 125000000623 heterocyclic group Chemical group 0.000 claims description 116
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 108
• 125000000217 alkyl group Chemical group 0.000 claims description 76
• 125000001424 substituent group Chemical group 0.000 claims description 64
• 125000005843 halogen group Chemical group 0.000 claims description 51
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
• 125000002757 morpholinyl group Chemical group 0.000 claims description 40
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 38
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 37
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
• 125000004043 oxo group Chemical group O=* 0.000 claims description 34
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 26
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 22
• 125000001153 fluoro group Chemical group F* 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 21
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 20
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 16
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 16
• 208000035475 disorder Diseases 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 15
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 14
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 14
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims description 13
• 125000002883 imidazolyl group Chemical group 0.000 claims description 13
• 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 13
• 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims description 12
• 229920006395 saturated elastomer Polymers 0.000 claims description 12
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 10
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 9
• 125000003282 alkyl amino group Chemical group 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 8
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 7
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 7
• 125000005493 quinolyl group Chemical group 0.000 claims description 7
• 230000001225 therapeutic effect Effects 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 6
• 206010061218 Inflammation Diseases 0.000 claims description 6
• 241001465754 Metazoa Species 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 230000004054 inflammatory process Effects 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
• 230000035755 proliferation Effects 0.000 claims description 6
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 6
• 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 claims description 6
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 6
• 125000002856 2-fluorophenylethyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
• 125000001246 bromo group Chemical group Br* 0.000 claims description 5
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 5
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 230000009467 reduction Effects 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 4
• UBFZXVYANXWBCM-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-8-(pyridin-4-ylmethylamino)-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2CC1 UBFZXVYANXWBCM-UHFFFAOYSA-N 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 4
• SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 4
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 4
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 4
• 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
• 239000002256 antimetabolite Substances 0.000 claims description 3
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
• 229940125697 hormonal agent Drugs 0.000 claims description 3
• 229910052701 rubidium Inorganic materials 0.000 claims description 3
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
• KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 2
• 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
• 125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims description 2
• 101100203601 Caenorhabditis elegans sor-3 gene Proteins 0.000 claims description 2
• 229940100198 alkylating agent Drugs 0.000 claims description 2
• 239000002168 alkylating agent Substances 0.000 claims description 2
• 125000002619 bicyclic group Chemical group 0.000 claims description 2
• 230000017531 blood circulation Effects 0.000 claims description 2
• 239000000677 immunologic agent Substances 0.000 claims description 2
• 229940124541 immunological agent Drugs 0.000 claims description 2
• 125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims description 2
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 2
• AVAWMINJNRAQFS-UHFFFAOYSA-N n,n-dimethylpyrrolidin-3-amine Chemical compound CN(C)C1CCNC1 AVAWMINJNRAQFS-UHFFFAOYSA-N 0.000 claims description 2
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
• 125000004547 quinazolin-6-yl group Chemical group N1=CN=CC2=CC(=CC=C12)* 0.000 claims description 2
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 2
• 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
• RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 claims description 2
• LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
• RJWLAIMXRBDUMH-ULQDDVLXSA-N N-Acetylleucyl-leucyl-methioninal Chemical compound CSCC[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(C)=O RJWLAIMXRBDUMH-ULQDDVLXSA-N 0.000 claims 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
• 125000006513 pyridinyl methyl group Chemical group 0.000 claims 1
• 201000010099 disease Diseases 0.000 abstract description 23
• 230000008569 process Effects 0.000 abstract description 18
• 230000001404 mediated effect Effects 0.000 abstract description 5
• 239000000543 intermediate Substances 0.000 abstract description 3
• 238000011321 prophylaxis Methods 0.000 abstract description 3
• 239000000651 prodrug Substances 0.000 abstract 1
• 229940002612 prodrug Drugs 0.000 abstract 1
• 150000003254 radicals Chemical class 0.000 description 59
• 239000000203 mixture Substances 0.000 description 46
• 125000004432 carbon atom Chemical group C* 0.000 description 42
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 40
• 235000002639 sodium chloride Nutrition 0.000 description 39
• 238000006243 chemical reaction Methods 0.000 description 37
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
• 210000004027 cell Anatomy 0.000 description 29
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 22
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 22
• 239000000243 solution Substances 0.000 description 22
• 238000002360 preparation method Methods 0.000 description 21
• 235000019439 ethyl acetate Nutrition 0.000 description 20
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
• 239000000460 chlorine Substances 0.000 description 19
• 150000001299 aldehydes Chemical class 0.000 description 18
• 239000002253 acid Substances 0.000 description 17
• 238000009472 formulation Methods 0.000 description 16
• 239000002246 antineoplastic agent Substances 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
• 229940034982 antineoplastic agent Drugs 0.000 description 13
• 239000003921 oil Substances 0.000 description 13
• 235000019198 oils Nutrition 0.000 description 13
• 241000700159 Rattus Species 0.000 description 12
• 239000002585 base Substances 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• 239000007858 starting material Substances 0.000 description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
• 239000004480 active ingredient Substances 0.000 description 11
• 125000003118 aryl group Chemical group 0.000 description 11
• 125000006239 protecting group Chemical group 0.000 description 11
• 238000000746 purification Methods 0.000 description 11
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 11
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• 238000003818 flash chromatography Methods 0.000 description 10
• 238000001819 mass spectrum Methods 0.000 description 10
• 239000003981 vehicle Substances 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 125000004429 atom Chemical group 0.000 description 9
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• 125000004434 sulfur atom Chemical group 0.000 description 9
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• 102100024785 Fibroblast growth factor 2 Human genes 0.000 description 5
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