TWI542589B - Ｃ型肝炎病毒抑制劑 - Google Patents

Info

Publication number

TWI542589B

TWI542589B TW101116051A TW101116051A TWI542589B TW I542589 B TWI542589 B TW I542589B TW 101116051 A TW101116051 A TW 101116051A TW 101116051 A TW101116051 A TW 101116051A TW I542589 B TWI542589 B TW I542589B

Authority

TW

Taiwan

Prior art keywords

oxy

pyrrolo

dimethyl

ester

hexadehydrocyclopropyl

Prior art date

2011-05-05

Links

• Espacenet
• Global Dossier
• Discuss

• 241000711549 Hepacivirus C Species 0.000 title description 42
• 239000003112 inhibitor Substances 0.000 title 1
• -1 benzodioxanyl group Chemical group 0.000 claims description 1171
• 150000001875 compounds Chemical class 0.000 claims description 1140
• KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 643
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 268
• LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 claims description 183
• 150000001412 amines Chemical class 0.000 claims description 173
• 239000000203 mixture Substances 0.000 claims description 84
• ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 78
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 72
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 69
• 150000003839 salts Chemical class 0.000 claims description 64
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 51
• 239000002253 acid Substances 0.000 claims description 42
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 42
• 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 claims description 42
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims description 31
• DLTBAYKGXREKMW-UHFFFAOYSA-N cyclopropanesulfonic acid Chemical compound OS(=O)(=O)C1CC1 DLTBAYKGXREKMW-UHFFFAOYSA-N 0.000 claims description 29
• NBFABZHUOJWSDM-UHFFFAOYSA-N 5h-pyrrolo[1,2-a][1,4]diazepine Chemical compound C1C=CN=CC2=CC=CN12 NBFABZHUOJWSDM-UHFFFAOYSA-N 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 125000001188 haloalkyl group Chemical group 0.000 claims description 24
• 125000005843 halogen group Chemical group 0.000 claims description 24
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 24
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 24
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 20
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
• 230000002146 bilateral effect Effects 0.000 claims description 19
• 229960005286 carbaryl Drugs 0.000 claims description 19
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
• IREYIBNCFDVBFO-UHFFFAOYSA-N 1,2-diazacyclopentadecane Chemical compound C1CCCCCCNNCCCCCC1 IREYIBNCFDVBFO-UHFFFAOYSA-N 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 17
• 150000002148 esters Chemical class 0.000 claims description 17
• 230000000694 effects Effects 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 108010047761 Interferon-alpha Proteins 0.000 claims description 12
• 102000006992 Interferon-alpha Human genes 0.000 claims description 12
• 102000014150 Interferons Human genes 0.000 claims description 12
• 108010050904 Interferons Proteins 0.000 claims description 12
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 12
• 229940079322 interferon Drugs 0.000 claims description 12
• SJZBPJCXFMEAMR-UHFFFAOYSA-N (1,1,1-trifluoro-2-methylpropan-2-yl) carbamate Chemical compound FC(F)(F)C(C)(C)OC(N)=O SJZBPJCXFMEAMR-UHFFFAOYSA-N 0.000 claims description 11
• SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 239000003795 chemical substances by application Substances 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 10
• SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 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 claims description 10
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 10
• 208000015181 infectious disease Diseases 0.000 claims description 10
• VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims description 10
• BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims description 10
• HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 10
• 229960000329 ribavirin Drugs 0.000 claims description 10
• ALAUVXXIBDWIAM-UHFFFAOYSA-N (1,1,1-trifluoro-2-methylpropan-2-yl) N-aminocarbamate Chemical compound CC(C)(OC(=O)NN)C(F)(F)F ALAUVXXIBDWIAM-UHFFFAOYSA-N 0.000 claims description 9
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 8
• 238000011282 treatment Methods 0.000 claims description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
• 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 150000002431 hydrogen Chemical class 0.000 claims description 7
• RKTVIAJXTCLIJQ-UHFFFAOYSA-N CC(C)(C(C)(F)F)NC(=O)O Chemical compound CC(C)(C(C)(F)F)NC(=O)O RKTVIAJXTCLIJQ-UHFFFAOYSA-N 0.000 claims description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
• 108010022999 Serine Proteases Proteins 0.000 claims description 6
• 102000012479 Serine Proteases Human genes 0.000 claims description 6
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
• 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 claims description 6
• DIHPWPXPOQOIKS-UHFFFAOYSA-N 4-ethoxypyridazine Chemical compound CCOC1=CC=NN=C1 DIHPWPXPOQOIKS-UHFFFAOYSA-N 0.000 claims description 5
• 108060004795 Methyltransferase Proteins 0.000 claims description 5
• 101800001019 Non-structural protein 4B Proteins 0.000 claims description 5
• 101800001014 Non-structural protein 5A Proteins 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 5
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 5
• UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims description 4
• 101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 claims description 4
• 102100040018 Interferon alpha-2 Human genes 0.000 claims description 4
• 108010079944 Interferon-alpha2b Proteins 0.000 claims description 4
• 102000013462 Interleukin-12 Human genes 0.000 claims description 4
• 108010065805 Interleukin-12 Proteins 0.000 claims description 4
• 102000000588 Interleukin-2 Human genes 0.000 claims description 4
• 108010002350 Interleukin-2 Proteins 0.000 claims description 4
• 102000004889 Interleukin-6 Human genes 0.000 claims description 4
• 108090001005 Interleukin-6 Proteins 0.000 claims description 4
• 108010006035 Metalloproteases Proteins 0.000 claims description 4
• 102000005741 Metalloproteases Human genes 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 4
• 229960003805 amantadine Drugs 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims description 4
• 229960002751 imiquimod Drugs 0.000 claims description 4
• 108700027921 interferon tau Proteins 0.000 claims description 4
• 229940117681 interleukin-12 Drugs 0.000 claims description 4
• 229940100601 interleukin-6 Drugs 0.000 claims description 4
• VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 229960000888 rimantadine Drugs 0.000 claims description 4
• FNXMSIHJJROGEJ-UHFFFAOYSA-N (1,1,1-trifluoro-2-methylpropan-2-yl)carbamic acid Chemical compound FC(F)(F)C(C)(C)NC(O)=O FNXMSIHJJROGEJ-UHFFFAOYSA-N 0.000 claims description 3
• NSGNREBTEFKPIL-UHFFFAOYSA-N 4-methoxypyridazine Chemical compound COC1=CC=NN=C1 NSGNREBTEFKPIL-UHFFFAOYSA-N 0.000 claims description 3
• CEJYQTHDTUMTPS-UHFFFAOYSA-N carbamic acid 1,1,1-trifluoro-2-methylpropane Chemical compound FC(C(C)C)(F)F.C(N)(O)=O CEJYQTHDTUMTPS-UHFFFAOYSA-N 0.000 claims description 3
• WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 claims description 3
• 125000001475 halogen functional group Chemical group 0.000 claims description 3
• 239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims description 3
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 3
• SNMLKBMPULDPTA-UWTATZPHSA-N (2r)-1,1,1-trifluoropropan-2-amine Chemical compound C[C@@H](N)C(F)(F)F SNMLKBMPULDPTA-UWTATZPHSA-N 0.000 claims description 2
• FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 claims description 2
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
• 125000005055 alkyl alkoxy group Chemical group 0.000 claims description 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
• 150000001408 amides Chemical class 0.000 claims description 2
• 150000003857 carboxamides Chemical class 0.000 claims description 2
• 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 2
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
• 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
• 125000006809 haloalkylaminocarbonyl group Chemical group 0.000 claims description 2
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000006611 nonyloxy group Chemical group 0.000 claims description 2
• 125000004193 piperazinyl group Chemical group 0.000 claims description 2
• 125000005936 piperidyl group Chemical group 0.000 claims description 2
• 229960005235 piperonyl butoxide Drugs 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims description 2
• FMPXYODRXNVVAR-UHFFFAOYSA-N CC(C)(C(F)(F)F)OC(=O)NC1CCCCCCCCCN(NCCC1)C2CCCCCCCCCCCCCC2 Chemical compound CC(C)(C(F)(F)F)OC(=O)NC1CCCCCCCCCN(NCCC1)C2CCCCCCCCCCCCCC2 FMPXYODRXNVVAR-UHFFFAOYSA-N 0.000 claims 81
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims 56
• QGFYFOHMBDMGBZ-UHFFFAOYSA-N 5-[(7-chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)phenol Chemical compound C1=C(O)C(CN(CC)CC)=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 QGFYFOHMBDMGBZ-UHFFFAOYSA-N 0.000 claims 5
• HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-dioxene Chemical compound C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 claims 4
• MDUMKDKGRGEJKE-UHFFFAOYSA-N 1-methylcyclopropane-1-sulfonic acid Chemical compound OS(=O)(=O)C1(C)CC1 MDUMKDKGRGEJKE-UHFFFAOYSA-N 0.000 claims 4
• RZHDRAZYNNMJIW-UHFFFAOYSA-N CC(C)(C(C)(F)F)OC(=O)NN Chemical compound CC(C)(C(C)(F)F)OC(=O)NN RZHDRAZYNNMJIW-UHFFFAOYSA-N 0.000 claims 4
• BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
• YYYQVCATDMJBTG-UHFFFAOYSA-N C(CCCC1)CCCCC=CCCCC1C1CCCN=NCCCCCCCCC1 Chemical group C(CCCC1)CCCCC=CCCCC1C1CCCN=NCCCCCCCCC1 YYYQVCATDMJBTG-UHFFFAOYSA-N 0.000 claims 3
• 229910001873 dinitrogen Inorganic materials 0.000 claims 3
• 239000011737 fluorine Substances 0.000 claims 3
• BBOUSJIHFHLBIZ-UHFFFAOYSA-N fluoromethylcyclopropane Chemical compound FCC1CC1 BBOUSJIHFHLBIZ-UHFFFAOYSA-N 0.000 claims 3
• GEGDLANPARTRKE-UHFFFAOYSA-N 4-methyl-2,3-dihydro-1,4-oxazine Chemical compound CN1CCOC=C1 GEGDLANPARTRKE-UHFFFAOYSA-N 0.000 claims 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
• NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 claims 2
• ZXAISWHLHOKQPD-UHFFFAOYSA-N (4-methyloxan-4-yl) n-aminocarbamate Chemical compound NNC(=O)OC1(C)CCOCC1 ZXAISWHLHOKQPD-UHFFFAOYSA-N 0.000 claims 1
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
• WZQRMZSLIAFYFJ-UHFFFAOYSA-N 3,3,3-trifluoro-2,2-bis(trifluoromethyl)propanoic acid Chemical compound OC(=O)C(C(F)(F)F)(C(F)(F)F)C(F)(F)F WZQRMZSLIAFYFJ-UHFFFAOYSA-N 0.000 claims 1
• OBODZWYMCPRQNA-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-methoxyisoquinoline Chemical compound FC1=CC=C(C=C1)C=1N=CC2=CC=C(C=C2C=1)OC OBODZWYMCPRQNA-UHFFFAOYSA-N 0.000 claims 1
• DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 claims 1
• XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims 1
• IGGGWGBPSWUADK-UHFFFAOYSA-N 6-ethoxyisoquinoline Chemical compound C1=NC=CC2=CC(OCC)=CC=C21 IGGGWGBPSWUADK-UHFFFAOYSA-N 0.000 claims 1
• RIQXGSMNHPFSDH-UHFFFAOYSA-N 6-propan-2-yloxyisoquinoline Chemical compound C1=NC=CC2=CC(OC(C)C)=CC=C21 RIQXGSMNHPFSDH-UHFFFAOYSA-N 0.000 claims 1
• IQQQOQYZKQBOLE-UHFFFAOYSA-N C1CCCCC(CCCN=NCCCC1)NNC(=O)OC2=CC=CC=C2F Chemical compound C1CCCCC(CCCN=NCCCC1)NNC(=O)OC2=CC=CC=C2F IQQQOQYZKQBOLE-UHFFFAOYSA-N 0.000 claims 1
• GCYCMTHRLKVZDW-UHFFFAOYSA-N C1CCCCCCC=C(CCCCCC1)C2=NCCCCCCCCCCCCN2 Chemical group C1CCCCCCC=C(CCCCCC1)C2=NCCCCCCCCCCCCN2 GCYCMTHRLKVZDW-UHFFFAOYSA-N 0.000 claims 1
• JDKPVNZRGFVQMV-UHFFFAOYSA-N CC(C)(C(F)(F)F)N1CCCCCN1 Chemical compound CC(C)(C(F)(F)F)N1CCCCCN1 JDKPVNZRGFVQMV-UHFFFAOYSA-N 0.000 claims 1
• YBQMDNUQKYICAR-UHFFFAOYSA-N CC(C)(C(F)(F)F)OC(=O)NNC1CCCCCCCCCC=CCCC1 Chemical compound CC(C)(C(F)(F)F)OC(=O)NNC1CCCCCCCCCC=CCCC1 YBQMDNUQKYICAR-UHFFFAOYSA-N 0.000 claims 1
• ULQNSFJRSHAGOZ-UHFFFAOYSA-N CC(CCCC=C)NNC(=O)O Chemical compound CC(CCCC=C)NNC(=O)O ULQNSFJRSHAGOZ-UHFFFAOYSA-N 0.000 claims 1
• KPMIVQJXHMLZOL-UHFFFAOYSA-N CCCCCCCCCCCC(CCCC=C)NNC(=O)O Chemical compound CCCCCCCCCCCC(CCCC=C)NNC(=O)O KPMIVQJXHMLZOL-UHFFFAOYSA-N 0.000 claims 1
• TYVOOUXGWPDEJG-UHFFFAOYSA-N CCOC1=CC2=C(C=NC=C2C=C1)OC Chemical compound CCOC1=CC2=C(C=NC=C2C=C1)OC TYVOOUXGWPDEJG-UHFFFAOYSA-N 0.000 claims 1
• 108050006182 Inosine-5'-monophosphate dehydrogenases Proteins 0.000 claims 1
• 102000016600 Inosine-5'-monophosphate dehydrogenases Human genes 0.000 claims 1
• VKLDYQKQYVKNLE-UHFFFAOYSA-N OC(NC(CCCCCCCCC1)CCCNN1C1CCCCCCCCCCCCCC1)=O Chemical compound OC(NC(CCCCCCCCC1)CCCNN1C1CCCCCCCCCCCCCC1)=O VKLDYQKQYVKNLE-UHFFFAOYSA-N 0.000 claims 1
• SWGQIGNWMBPMGO-UWTATZPHSA-N [(2r)-1,1,1-trifluoropropan-2-yl] carbamate Chemical compound FC(F)(F)[C@@H](C)OC(N)=O SWGQIGNWMBPMGO-UWTATZPHSA-N 0.000 claims 1
• AWVQALYBPDVINU-UHFFFAOYSA-N [1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yl] benzoate Chemical compound C1=CC=C(C=C1)C(=O)OC(C(F)(F)F)(C(F)(F)F)C(F)(F)F AWVQALYBPDVINU-UHFFFAOYSA-N 0.000 claims 1
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
• BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 claims 1
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