NZ584108A - Imidazo [1,2-a] pyrazine compounds for treatment of viral infections such as hepatitis - Google Patents

Info

Publication number

NZ584108A

NZ584108A NZ584108A NZ58410808A NZ584108A NZ 584108 A NZ584108 A NZ 584108A NZ 584108 A NZ584108 A NZ 584108A NZ 58410808 A NZ58410808 A NZ 58410808A NZ 584108 A NZ584108 A NZ 584108A

Authority

NZ

New Zealand

Prior art keywords

alkyl

substituted

unsubstituted

alkoxy

compound

Prior art date

2007-08-21

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• 238000011282 treatment Methods 0.000 title claims abstract description 33
• 208000036142 Viral infection Diseases 0.000 title claims abstract description 22
• 230000009385 viral infection Effects 0.000 title claims abstract description 22
• 208000006454 hepatitis Diseases 0.000 title 1
• 231100000283 hepatitis Toxicity 0.000 title 1
• 150000005236 imidazo[1,2-a]pyrazines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 279
• 125000000217 alkyl group Chemical group 0.000 claims description 130
• 125000003545 alkoxy group Chemical group 0.000 claims description 116
• 229910052736 halogen Inorganic materials 0.000 claims description 44
• 150000002367 halogens Chemical class 0.000 claims description 44
• CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 34
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 21
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 13
• 230000002265 prevention Effects 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 2
• 230000007717 exclusion Effects 0.000 claims 1
• JVMWXARNXCVSIK-UHFFFAOYSA-N 4-[[[3-(2-fluoro-4-hydroxyphenyl)imidazo[1,2-a]pyrazin-8-yl]amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC1=NC=CN2C1=NC=C2C1=CC=C(O)C=C1F JVMWXARNXCVSIK-UHFFFAOYSA-N 0.000 abstract 1
• 125000003118 aryl group Chemical group 0.000 description 105
• 125000005843 halogen group Chemical group 0.000 description 94
• 125000000753 cycloalkyl group Chemical group 0.000 description 75
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 68
• -1 imidazopyrazine compound Chemical class 0.000 description 64
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 55
• 239000007787 solid Substances 0.000 description 55
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 52
• 239000000203 mixture Substances 0.000 description 50
• 241000711549 Hepacivirus C Species 0.000 description 49
• 239000000243 solution Substances 0.000 description 49
• 238000000034 method Methods 0.000 description 43
• 125000001188 haloalkyl group Chemical group 0.000 description 41
• GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical class CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 description 40
• 125000001072 heteroaryl group Chemical group 0.000 description 40
• 238000006243 chemical reaction Methods 0.000 description 39
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 37
• 150000003254 radicals Chemical class 0.000 description 36
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
• 125000003710 aryl alkyl group Chemical group 0.000 description 32
• 125000004438 haloalkoxy group Chemical group 0.000 description 31
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 30
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 24
• 125000001424 substituent group Chemical group 0.000 description 24
• 101100134927 Gallus gallus COR8 gene Proteins 0.000 description 23
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
• 230000000694 effects Effects 0.000 description 21
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
• 239000011541 reaction mixture Substances 0.000 description 17
• 239000000651 prodrug Substances 0.000 description 16
• 229940002612 prodrug Drugs 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• 238000007429 general method Methods 0.000 description 15
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
• 125000005842 heteroatom Chemical group 0.000 description 14
• 229910052739 hydrogen Inorganic materials 0.000 description 14
• 239000000047 product Substances 0.000 description 14
• 239000012453 solvate Substances 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• 239000013543 active substance Substances 0.000 description 13
• 239000001257 hydrogen Substances 0.000 description 13
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• 241000709664 Picornaviridae Species 0.000 description 12
• 238000009472 formulation Methods 0.000 description 12
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
• 239000012044 organic layer Substances 0.000 description 12
• 125000003107 substituted aryl group Chemical group 0.000 description 12
• 125000004093 cyano group Chemical group *C#N 0.000 description 11
• 208000015181 infectious disease Diseases 0.000 description 11
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• 125000004432 carbon atom Chemical group C* 0.000 description 10
• 239000003112 inhibitor Substances 0.000 description 10
• IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 235000019439 ethyl acetate Nutrition 0.000 description 9
• 150000002431 hydrogen Chemical class 0.000 description 9
• 241000430519 Human rhinovirus sp. Species 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• 239000004480 active ingredient Substances 0.000 description 8
• 125000004414 alkyl thio group Chemical group 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
• 238000004440 column chromatography Methods 0.000 description 8
• 150000005235 imidazopyrazines Chemical class 0.000 description 8
• 239000002244 precipitate Substances 0.000 description 8
• 230000010076 replication Effects 0.000 description 8
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 7
• 241000709661 Enterovirus Species 0.000 description 7
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 7
• 241000124008 Mammalia Species 0.000 description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
• 210000004027 cell Anatomy 0.000 description 7
• 230000000155 isotopic effect Effects 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• 125000003396 thiol group Chemical class [H]S* 0.000 description 7
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• 125000004442 acylamino group Chemical group 0.000 description 6
• 238000003556 assay Methods 0.000 description 6
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• 229940079593 drug Drugs 0.000 description 6
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• 125000000623 heterocyclic group Chemical group 0.000 description 6
• 108010010648 interferon alfacon-1 Proteins 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 229910052757 nitrogen Inorganic materials 0.000 description 6
• 239000012299 nitrogen atmosphere Substances 0.000 description 6
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
• 229920006395 saturated elastomer Polymers 0.000 description 6
• 229910000029 sodium carbonate Inorganic materials 0.000 description 6
• SIACJRVYIPXFKS-UHFFFAOYSA-N (4-sulfamoylphenyl)methylazanium;chloride Chemical compound Cl.NCC1=CC=C(S(N)(=O)=O)C=C1 SIACJRVYIPXFKS-UHFFFAOYSA-N 0.000 description 5
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
• 241000709687 Coxsackievirus Species 0.000 description 5
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• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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• 238000002953 preparative HPLC Methods 0.000 description 5
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