NZ579890A - 4'-o-substituted isoindoline derivatives and compositions comprising and methods of using the same - Google Patents

Info

Publication number

NZ579890A

NZ579890A NZ579890A NZ57989008A NZ579890A NZ 579890 A NZ579890 A NZ 579890A NZ 579890 A NZ579890 A NZ 579890A NZ 57989008 A NZ57989008 A NZ 57989008A NZ 579890 A NZ579890 A NZ 579890A

Authority

NZ

New Zealand

Prior art keywords

compound

mmol

disease

disorder

mixture

Prior art date

2007-03-20

Links

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• 238000000034 method Methods 0.000 title claims description 32
• GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title abstract description 7
• 239000000203 mixture Chemical class 0.000 title description 151
• 150000001875 compounds Chemical class 0.000 claims abstract description 152
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 119
• 208000035475 disorder Diseases 0.000 claims abstract description 62
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 41
• 201000011510 cancer Diseases 0.000 claims abstract description 29
• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 229940002612 prodrug Drugs 0.000 claims abstract description 25
• 239000000651 prodrug Substances 0.000 claims abstract description 25
• 239000012453 solvate Substances 0.000 claims abstract description 22
• 208000002193 Pain Diseases 0.000 claims abstract description 19
• 208000011580 syndromic disease Diseases 0.000 claims abstract description 17
• 230000006378 damage Effects 0.000 claims abstract description 14
• 230000033115 angiogenesis Effects 0.000 claims abstract description 12
• 208000014674 injury Diseases 0.000 claims abstract description 11
• 208000027418 Wounds and injury Diseases 0.000 claims abstract description 10
• 208000017520 skin disease Diseases 0.000 claims abstract description 9
• 208000029462 Immunodeficiency disease Diseases 0.000 claims abstract description 6
• 208000030852 Parasitic disease Diseases 0.000 claims abstract description 6
• 239000010425 asbestos Substances 0.000 claims abstract description 6
• 208000034737 hemoglobinopathy Diseases 0.000 claims abstract description 6
• 208000002780 macular degeneration Diseases 0.000 claims abstract description 6
• 229910052895 riebeckite Inorganic materials 0.000 claims abstract description 6
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 5
• 208000035473 Communicable disease Diseases 0.000 claims abstract description 5
• 208000019693 Lung disease Diseases 0.000 claims abstract description 5
• 208000015114 central nervous system disease Diseases 0.000 claims abstract description 5
• 208000015181 infectious disease Diseases 0.000 claims abstract description 5
• -1 chloro, bromo, fluoro, methyl Chemical group 0.000 claims description 89
• 201000010099 disease Diseases 0.000 claims description 57
• 239000002552 dosage form Substances 0.000 claims description 57
• 239000013543 active substance Substances 0.000 claims description 39
• 239000003814 drug Substances 0.000 claims description 36
• 239000008194 pharmaceutical composition Substances 0.000 claims description 34
• 125000000217 alkyl group Chemical group 0.000 claims description 29
• 125000003118 aryl group Chemical group 0.000 claims description 26
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 125000001424 substituent group Chemical group 0.000 claims description 9
• 108700012920 TNF Proteins 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 239000000463 material Substances 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
• 125000001188 haloalkyl group Chemical group 0.000 claims description 7
• 125000002950 monocyclic group Chemical group 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 239000002775 capsule Substances 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 150000002825 nitriles Chemical class 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 4
• 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 4
• SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 229960005486 vaccine Drugs 0.000 claims description 4
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 3
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 125000005493 quinolyl group Chemical group 0.000 claims description 3
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 claims description 2
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
• 125000002619 bicyclic group Chemical group 0.000 claims description 2
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 2
• 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
• 229940022399 cancer vaccine Drugs 0.000 claims 1
• 238000009566 cancer vaccine Methods 0.000 claims 1
• 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract description 4
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 213
• 229910001868 water Inorganic materials 0.000 description 110
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 102
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
• 235000019439 ethyl acetate Nutrition 0.000 description 73
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
• 239000007787 solid Substances 0.000 description 60
• 239000004480 active ingredient Substances 0.000 description 47
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
• 239000000243 solution Substances 0.000 description 47
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 42
• 239000000047 product Substances 0.000 description 42
• 238000011282 treatment Methods 0.000 description 42
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
• 238000005481 NMR spectroscopy Methods 0.000 description 37
• 210000004027 cell Anatomy 0.000 description 34
• 239000002904 solvent Substances 0.000 description 31
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
• 238000000746 purification Methods 0.000 description 28
• 238000003818 flash chromatography Methods 0.000 description 27
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
• 238000004128 high performance liquid chromatography Methods 0.000 description 24
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
• 239000003112 inhibitor Substances 0.000 description 22
• 239000003643 water by type Substances 0.000 description 22
• BQGDDMMXPRJQHZ-UHFFFAOYSA-N dimethyl 3-hydroxybenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=CC(O)=C1C(=O)OC BQGDDMMXPRJQHZ-UHFFFAOYSA-N 0.000 description 21
• 230000002265 prevention Effects 0.000 description 21
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 21
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 20
• 229940079593 drug Drugs 0.000 description 20
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
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• 235000011007 phosphoric acid Nutrition 0.000 description 18
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• 239000012044 organic layer Substances 0.000 description 15
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