JP2020526546A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2020526546A5 JP2020526546A5 JP2020501229A JP2020501229A JP2020526546A5 JP 2020526546 A5 JP2020526546 A5 JP 2020526546A5 JP 2020501229 A JP2020501229 A JP 2020501229A JP 2020501229 A JP2020501229 A JP 2020501229A JP 2020526546 A5 JP2020526546 A5 JP 2020526546A5
- Authority
- JP
- Japan
- Prior art keywords
- spiro
- dihydro
- cyclohexane
- chloro
- quinazoline
- Prior art date
- 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.)
- Granted
Links
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 331
- 125000000217 alkyl group Chemical group 0.000 claims 324
- -1 -C 3-7 cycloalkyl Chemical group 0.000 claims 170
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 156
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 91
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 87
- 125000001188 haloalkyl group Chemical group 0.000 claims 86
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 86
- 125000000753 cycloalkyl group Chemical group 0.000 claims 75
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 68
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 66
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 64
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 62
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 56
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 55
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 52
- 125000001072 heteroaryl group Chemical group 0.000 claims 52
- 125000005843 halogen group Chemical group 0.000 claims 49
- 125000003118 aryl group Chemical group 0.000 claims 45
- 150000001875 compounds Chemical class 0.000 claims 41
- 150000003839 salts Chemical class 0.000 claims 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 37
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 34
- 125000001424 substituent group Chemical group 0.000 claims 32
- 125000004076 pyridyl group Chemical group 0.000 claims 31
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 30
- 125000002619 bicyclic group Chemical group 0.000 claims 29
- 125000002950 monocyclic group Chemical group 0.000 claims 29
- 125000003545 alkoxy group Chemical group 0.000 claims 25
- 229930192474 thiophene Natural products 0.000 claims 24
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 23
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 21
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 21
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 19
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 17
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 16
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 16
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims 15
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 14
- HXJUTPCZVOIRIF-UHFFFAOYSA-N Tetrahydrothiophene-1,1-dioxide, Natural products O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 13
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 12
- 150000001345 alkine derivatives Chemical class 0.000 claims 11
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 125000000304 alkynyl group Chemical group 0.000 claims 10
- 208000035475 disorder Diseases 0.000 claims 10
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims 10
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 9
- 208000006011 Stroke Diseases 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 9
- XCRMJVAKOKRMRS-UHFFFAOYSA-N 1,2-diazaspiro[5.5]undecane Chemical compound C1CCCCC21NNCCC2 XCRMJVAKOKRMRS-UHFFFAOYSA-N 0.000 claims 8
- BLOINAPUWZYQMD-UHFFFAOYSA-N 1-azabicyclo[4.1.0]heptane Chemical compound C1CCCN2CC21 BLOINAPUWZYQMD-UHFFFAOYSA-N 0.000 claims 8
- HZLUMDLSMBEFMQ-UHFFFAOYSA-N 2-oxa-8-azaspiro[4.5]decan-1-one Chemical compound O=C1OCCC11CCNCC1 HZLUMDLSMBEFMQ-UHFFFAOYSA-N 0.000 claims 8
- QRDSDKAGXMWBID-UHFFFAOYSA-N 5-azabicyclo[3.1.0]hexane Chemical compound C1CCN2CC21 QRDSDKAGXMWBID-UHFFFAOYSA-N 0.000 claims 8
- WZFOPYGRZNUWSP-UHFFFAOYSA-N 7-oxa-2-azaspiro[3.5]nonane Chemical compound C1NCC11CCOCC1 WZFOPYGRZNUWSP-UHFFFAOYSA-N 0.000 claims 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 8
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 8
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 8
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 8
- SKFZSJIOAVSXCU-UHFFFAOYSA-N spiro[3,4-dihydroisochromene-1,4'-piperidine] Chemical compound C1CNCCC21C1=CC=CC=C1CCO2 SKFZSJIOAVSXCU-UHFFFAOYSA-N 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 239000011593 sulfur Substances 0.000 claims 8
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 7
- HPARLNRMYDSBNO-UHFFFAOYSA-N 1,4-benzodioxine Chemical compound C1=CC=C2OC=COC2=C1 HPARLNRMYDSBNO-UHFFFAOYSA-N 0.000 claims 7
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 7
- JKWQHCSGMTWRIQ-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NCCC2=N1 JKWQHCSGMTWRIQ-UHFFFAOYSA-N 0.000 claims 7
- JHTIYCNAYYKEGT-UHFFFAOYSA-N 2-oxa-1-azabicyclo[2.2.1]heptane Chemical compound C1C2CCN1OC2 JHTIYCNAYYKEGT-UHFFFAOYSA-N 0.000 claims 7
- DIQOUXNTSMWQSA-UHFFFAOYSA-N 2-oxa-5-azabicyclo[2.2.1]heptane Chemical compound C1OC2CNC1C2 DIQOUXNTSMWQSA-UHFFFAOYSA-N 0.000 claims 7
- RECARUFTCUAFPV-UHFFFAOYSA-N 2-oxa-7-azaspiro[3.5]nonane Chemical compound C1OCC11CCNCC1 RECARUFTCUAFPV-UHFFFAOYSA-N 0.000 claims 7
- HGWUUOXXAIISDB-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexane Chemical compound C1NCC2CC21 HGWUUOXXAIISDB-UHFFFAOYSA-N 0.000 claims 7
- FTGUMOQCPJEKOR-UHFFFAOYSA-N 6-oxa-9-azaspiro[4.5]decane Chemical compound C1CCCC21OCCNC2 FTGUMOQCPJEKOR-UHFFFAOYSA-N 0.000 claims 7
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 7
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 7
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 7
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 7
- MKCBRYIXFFGIKN-UHFFFAOYSA-N bicyclo[1.1.1]pentane Chemical compound C1C2CC1C2 MKCBRYIXFFGIKN-UHFFFAOYSA-N 0.000 claims 7
- JAPMJSVZDUYFKL-UHFFFAOYSA-N bicyclo[3.1.0]hexane Chemical compound C1CCC2CC21 JAPMJSVZDUYFKL-UHFFFAOYSA-N 0.000 claims 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 7
- 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 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 7
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims 7
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 239000001301 oxygen Substances 0.000 claims 7
- SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical compound C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 claims 7
- 125000003386 piperidinyl group Chemical group 0.000 claims 7
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 7
- OXXXNXISRXFPBK-UHFFFAOYSA-N 2-oxa-8-azaspiro[4.5]decane Chemical compound C1OCCC21CCNCC2 OXXXNXISRXFPBK-UHFFFAOYSA-N 0.000 claims 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 6
- 208000012902 Nervous system disease Diseases 0.000 claims 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 6
- 230000004913 activation Effects 0.000 claims 6
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical group ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 claims 6
- RQHOGSOCPPWOJC-UHFFFAOYSA-N spiro[3h-chromene-2,3'-pyrrolidine]-4-one Chemical compound O1C2=CC=CC=C2C(=O)CC21CCNC2 RQHOGSOCPPWOJC-UHFFFAOYSA-N 0.000 claims 6
- QZRPWSLIWFBELO-UHFFFAOYSA-N spiro[6,7-dihydro-5h-thieno[3,2-c]pyridine-4,4'-piperidine] Chemical compound C1CNCCC21C(C=CS1)=C1CCN2 QZRPWSLIWFBELO-UHFFFAOYSA-N 0.000 claims 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 6
- HQTYIRUSJRQGBS-UHFFFAOYSA-N 1-oxa-8-azaspiro[4.5]decan-3-one Chemical compound C1C(=O)COC21CCNCC2 HQTYIRUSJRQGBS-UHFFFAOYSA-N 0.000 claims 5
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 5
- UMEIYBJBGZKZOS-UHFFFAOYSA-N 5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine Chemical compound C1NCCN2C=NN=C21 UMEIYBJBGZKZOS-UHFFFAOYSA-N 0.000 claims 5
- SWBUHQQTIPEPMK-UHFFFAOYSA-N 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine Chemical compound C1NCCN2C=CN=C21 SWBUHQQTIPEPMK-UHFFFAOYSA-N 0.000 claims 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 5
- INLLUQVDJROGIE-UHFFFAOYSA-N S1C=CC2=C1C1(NCC2)CCNCC1 Chemical compound S1C=CC2=C1C1(NCC2)CCNCC1 INLLUQVDJROGIE-UHFFFAOYSA-N 0.000 claims 5
- 208000010877 cognitive disease Diseases 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- QFCMBRXRVQRSSF-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole Chemical compound C1NCC2CNCC21 QFCMBRXRVQRSSF-UHFFFAOYSA-N 0.000 claims 4
- WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 claims 4
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 4
- GCODEMBJCAEKNJ-UHFFFAOYSA-N 2,3,4,5-tetrahydropyrido[2,3-f][1,4]oxazepine Chemical compound C1NCCOC2=CC=CN=C21 GCODEMBJCAEKNJ-UHFFFAOYSA-N 0.000 claims 4
- JIPXZUULKFLFHD-UHFFFAOYSA-N 2,4,7,7a-tetrahydro-1h-imidazo[4,5-b]pyrazine Chemical compound N1C=CNC2=NCNC21 JIPXZUULKFLFHD-UHFFFAOYSA-N 0.000 claims 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 4
- GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical compound CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 claims 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- XJLDYKIEURAVBW-UHFFFAOYSA-N Aethyl-heptyl-keton Natural products CCCCCCCC(=O)CC XJLDYKIEURAVBW-UHFFFAOYSA-N 0.000 claims 4
- DQSVFRXTUGLVSJ-UHFFFAOYSA-N CC1CCCCN1Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CC1CCCCN1Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 DQSVFRXTUGLVSJ-UHFFFAOYSA-N 0.000 claims 4
- 208000018737 Parkinson disease Diseases 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N monomethyl-formamide Natural products CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 4
- 230000009251 neurologic dysfunction Effects 0.000 claims 4
- 208000015015 neurological dysfunction Diseases 0.000 claims 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 4
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 4
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims 4
- 150000003852 triazoles Chemical class 0.000 claims 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 3
- MKOIWLVTFRQTJW-UHFFFAOYSA-N 5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C1CCCN2C=NN=C21 MKOIWLVTFRQTJW-UHFFFAOYSA-N 0.000 claims 3
- ZUMUJKQGAPXFLM-UHFFFAOYSA-N 5-chloro-2-[[2-(dimethylamino)ethyl-methylamino]methyl]spiro[6,8-dihydro-[1,3]oxazolo[5,4-f]quinazoline-9,1'-cyclohexane]-7-one Chemical compound CN(C)CCN(C)CC1=NC2=CC(=C3C(=C2O1)C4(CCCCC4)NC(=O)N3)Cl ZUMUJKQGAPXFLM-UHFFFAOYSA-N 0.000 claims 3
- IWDMWRFGBFCYQD-UHFFFAOYSA-N CN(Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)C1CCOCC1 Chemical compound CN(Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)C1CCOCC1 IWDMWRFGBFCYQD-UHFFFAOYSA-N 0.000 claims 3
- FIWQVLYLPLDEPY-UHFFFAOYSA-N COC1(C)CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound COC1(C)CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 FIWQVLYLPLDEPY-UHFFFAOYSA-N 0.000 claims 3
- 208000019430 Motor disease Diseases 0.000 claims 3
- LRUJXVIFHZUNCH-UHFFFAOYSA-N OCC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound OCC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 LRUJXVIFHZUNCH-UHFFFAOYSA-N 0.000 claims 3
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 3
- 230000006872 improvement Effects 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 206010025135 lupus erythematosus Diseases 0.000 claims 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- IOLQWFQLCNMKAZ-UHFFFAOYSA-N 1,2,3,6-tetrahydropyrazine Chemical compound C1CN=CCN1 IOLQWFQLCNMKAZ-UHFFFAOYSA-N 0.000 claims 2
- DWKUKQRKVCMOLP-UHFFFAOYSA-N 1-piperideine Chemical compound C1CCN=CC1 DWKUKQRKVCMOLP-UHFFFAOYSA-N 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims 2
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- QXIYTSXNJSIWFZ-UHFFFAOYSA-N 5,6,7,8-tetrahydro-2h-pyrido[3,4-d]pyridazin-1-one Chemical compound C1NCCC2=C1C=NNC2=O QXIYTSXNJSIWFZ-UHFFFAOYSA-N 0.000 claims 2
- BKBYLHWOJBKKQT-UHFFFAOYSA-N 5-chloro-2-(2-hydroxyethyl)spiro[6,8-dihydro-[1,3]oxazolo[5,4-f]quinazoline-9,1'-cyclohexane]-7-one Chemical compound C1=C(C2=C(C3=C1N=C(O3)CCO)C1(CCCCC1)NC(=O)N2)Cl BKBYLHWOJBKKQT-UHFFFAOYSA-N 0.000 claims 2
- VSJICRRMKMRZHC-UHFFFAOYSA-N 5-chloro-2-[[(2-methoxyphenyl)methylamino]methyl]spiro[6,8-dihydro-[1,3]oxazolo[5,4-f]quinazoline-9,1'-cyclohexane]-7-one Chemical compound COC1=CC=CC=C1CNCC2=NC3=CC(=C4C(=C3O2)C5(CCCCC5)NC(=O)N4)Cl VSJICRRMKMRZHC-UHFFFAOYSA-N 0.000 claims 2
- WDWRKOLWNQJXDH-ZDUSSCGKSA-N 5-chloro-2-[[(3S)-3-methoxypiperidin-1-yl]methyl]spiro[6,8-dihydro-[1,3]oxazolo[5,4-f]quinazoline-9,1'-cyclohexane]-7-one Chemical compound CO[C@H]1CCCN(C1)CC2=NC3=CC(=C4C(=C3O2)C5(CCCCC5)NC(=O)N4)Cl WDWRKOLWNQJXDH-ZDUSSCGKSA-N 0.000 claims 2
- WGNUHKDOAXYCRK-LBPRGKRZSA-N 5-chloro-2-[[[(3S)-oxan-3-yl]amino]methyl]spiro[6,8-dihydro-[1,3]oxazolo[5,4-f]quinazoline-9,1'-cyclohexane]-7-one Chemical compound C1CCC2(CC1)C3=C4C(=CC(=C3NC(=O)N2)Cl)N=C(O4)CN[C@H]5CCCOC5 WGNUHKDOAXYCRK-LBPRGKRZSA-N 0.000 claims 2
- IOIUPJUTDZQTPQ-NSHDSACASA-N 5-chloro-2-[[[(3S)-oxolan-3-yl]amino]methyl]spiro[6,8-dihydro-[1,3]oxazolo[5,4-f]quinazoline-9,1'-cyclohexane]-7-one Chemical compound C1CCC2(CC1)C3=C4C(=CC(=C3NC(=O)N2)Cl)N=C(O4)CN[C@H]5CCOC5 IOIUPJUTDZQTPQ-NSHDSACASA-N 0.000 claims 2
- NVZWMJWMTWOVNJ-UHFFFAOYSA-N 6-azaspiro[3.4]octane Chemical compound C1CCC21CNCC2 NVZWMJWMTWOVNJ-UHFFFAOYSA-N 0.000 claims 2
- FQCUDCXJZOKDGV-UHFFFAOYSA-N CC(=O)C1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound CC(=O)C1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 FQCUDCXJZOKDGV-UHFFFAOYSA-N 0.000 claims 2
- RRBQWNFMPZUISB-UHFFFAOYSA-N CC(=O)N1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound CC(=O)N1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 RRBQWNFMPZUISB-UHFFFAOYSA-N 0.000 claims 2
- KUBKPPCJLQOSGO-UHFFFAOYSA-N CC(C)C(=O)CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CC(C)C(=O)CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 KUBKPPCJLQOSGO-UHFFFAOYSA-N 0.000 claims 2
- KPXGORWGJRALGU-UHFFFAOYSA-N CC(C)COC1CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound CC(C)COC1CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 KPXGORWGJRALGU-UHFFFAOYSA-N 0.000 claims 2
- OMMOIXUCOFSUKQ-UHFFFAOYSA-N CC(C)N1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CC(C)N1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 OMMOIXUCOFSUKQ-UHFFFAOYSA-N 0.000 claims 2
- NHUCYTBTGACGCA-UHFFFAOYSA-N CC(C)N1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound CC(C)N1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 NHUCYTBTGACGCA-UHFFFAOYSA-N 0.000 claims 2
- WPFJESNDQRIXSP-UHFFFAOYSA-N CC(C)NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CC(C)NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 WPFJESNDQRIXSP-UHFFFAOYSA-N 0.000 claims 2
- CSJUCZCAQORFCK-UHFFFAOYSA-N CC(C)OC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound CC(C)OC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 CSJUCZCAQORFCK-UHFFFAOYSA-N 0.000 claims 2
- DKUQETJZOXSYNX-UHFFFAOYSA-N CC(NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)C1CCCCO1 Chemical compound CC(NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)C1CCCCO1 DKUQETJZOXSYNX-UHFFFAOYSA-N 0.000 claims 2
- KPGLQPJINULLKC-UHFFFAOYSA-N CC1(CCOC1)NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CC1(CCOC1)NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 KPGLQPJINULLKC-UHFFFAOYSA-N 0.000 claims 2
- KCNOVQJCMOIKNU-UHFFFAOYSA-N CC1(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)COC1 Chemical compound CC1(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)COC1 KCNOVQJCMOIKNU-UHFFFAOYSA-N 0.000 claims 2
- QHXNCLDUTWOTQV-UHFFFAOYSA-N CC1CC(CC(C)O1)NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CC1CC(CC(C)O1)NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 QHXNCLDUTWOTQV-UHFFFAOYSA-N 0.000 claims 2
- LKNPTZAWEREWIR-UHFFFAOYSA-N CC1N(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CCN(C)C1=O Chemical compound CC1N(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CCN(C)C1=O LKNPTZAWEREWIR-UHFFFAOYSA-N 0.000 claims 2
- KFWVVFDEPFGQAI-UHFFFAOYSA-N CCC(=O)N1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound CCC(=O)N1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 KFWVVFDEPFGQAI-UHFFFAOYSA-N 0.000 claims 2
- OFBBXRBNTCPMPC-UHFFFAOYSA-N CCC1COCCN1Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CCC1COCCN1Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 OFBBXRBNTCPMPC-UHFFFAOYSA-N 0.000 claims 2
- HOWRMGRFMQGRAB-UHFFFAOYSA-N CCCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CCCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 HOWRMGRFMQGRAB-UHFFFAOYSA-N 0.000 claims 2
- MOINQXVUEGIGOT-UHFFFAOYSA-N CCN(C)C(=O)CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CCN(C)C(=O)CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 MOINQXVUEGIGOT-UHFFFAOYSA-N 0.000 claims 2
- ONDIRTTYENSECV-UHFFFAOYSA-N CCN(CC)C(=O)CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CCN(CC)C(=O)CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 ONDIRTTYENSECV-UHFFFAOYSA-N 0.000 claims 2
- SWXCNTHYGZEVCO-UHFFFAOYSA-N CCN1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CCN1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 SWXCNTHYGZEVCO-UHFFFAOYSA-N 0.000 claims 2
- CKTHQKLOBUHUQJ-UHFFFAOYSA-N CCN1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound CCN1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 CKTHQKLOBUHUQJ-UHFFFAOYSA-N 0.000 claims 2
- WEPBPUNWPHIITB-UHFFFAOYSA-N CCN1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1=O Chemical compound CCN1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1=O WEPBPUNWPHIITB-UHFFFAOYSA-N 0.000 claims 2
- JUDYIVIVTMPDEN-UHFFFAOYSA-N CCNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CCNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 JUDYIVIVTMPDEN-UHFFFAOYSA-N 0.000 claims 2
- YWKJGLZLRDISGI-UHFFFAOYSA-N CCOC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound CCOC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 YWKJGLZLRDISGI-UHFFFAOYSA-N 0.000 claims 2
- BCEYSZIMSXAZRJ-GFCCVEGCSA-N CCO[C@@H]1CCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CCO[C@@H]1CCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 BCEYSZIMSXAZRJ-GFCCVEGCSA-N 0.000 claims 2
- PITNQINSAGLNJM-UHFFFAOYSA-N CCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 PITNQINSAGLNJM-UHFFFAOYSA-N 0.000 claims 2
- XOTUZMYEPHMGIQ-UHFFFAOYSA-N CN(C)C(=O)CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(C)C(=O)CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 XOTUZMYEPHMGIQ-UHFFFAOYSA-N 0.000 claims 2
- ODOBVNQJABFPDZ-UHFFFAOYSA-N CN(C)C(=O)CNCc1nc2cc(F)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(C)C(=O)CNCc1nc2cc(F)c3NC(=O)NC4(CCCCC4)c3c2o1 ODOBVNQJABFPDZ-UHFFFAOYSA-N 0.000 claims 2
- KTMYMVXRFZWNHV-UHFFFAOYSA-N CN(C)C(=O)COCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(C)C(=O)COCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 KTMYMVXRFZWNHV-UHFFFAOYSA-N 0.000 claims 2
- RCMFDUIYJCVVFW-UHFFFAOYSA-N CN(C)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(C)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 RCMFDUIYJCVVFW-UHFFFAOYSA-N 0.000 claims 2
- NEUMLGPDQCGFRQ-UHFFFAOYSA-N CN(C)C1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(C)C1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 NEUMLGPDQCGFRQ-UHFFFAOYSA-N 0.000 claims 2
- BDBMXZYSQPZBDO-UHFFFAOYSA-N CN(C)C1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound CN(C)C1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 BDBMXZYSQPZBDO-UHFFFAOYSA-N 0.000 claims 2
- FCXKVQKTKYLYSV-UHFFFAOYSA-N CN(C)C1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound CN(C)C1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 FCXKVQKTKYLYSV-UHFFFAOYSA-N 0.000 claims 2
- FFFFYYJAUNLWIC-UHFFFAOYSA-N CN(C)CCN(C)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(C)CCN(C)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 FFFFYYJAUNLWIC-UHFFFAOYSA-N 0.000 claims 2
- XNBXXQLTGLBFFF-UHFFFAOYSA-N CN(C)CCNC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(C)CCNC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 XNBXXQLTGLBFFF-UHFFFAOYSA-N 0.000 claims 2
- KUZIOXPXTPPIHI-UHFFFAOYSA-N CN(C)Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(C)Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 KUZIOXPXTPPIHI-UHFFFAOYSA-N 0.000 claims 2
- MUOYLTSWAGEMFE-UHFFFAOYSA-N CN(C1CCOCC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(C1CCOCC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 MUOYLTSWAGEMFE-UHFFFAOYSA-N 0.000 claims 2
- YVQQZLAGZGPMNG-UHFFFAOYSA-N CN(CC(=O)N(C)C)Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(CC(=O)N(C)C)Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 YVQQZLAGZGPMNG-UHFFFAOYSA-N 0.000 claims 2
- FZTGZPORPORKSK-UHFFFAOYSA-N CN(CC(=O)N(C)C)Cc1nc2cc(F)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(CC(=O)N(C)C)Cc1nc2cc(F)c3NC(=O)NC4(CCCCC4)c3c2o1 FZTGZPORPORKSK-UHFFFAOYSA-N 0.000 claims 2
- CLXVYTMNUHFYGZ-UHFFFAOYSA-N CN(CC1CCOCC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(CC1CCOCC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 CLXVYTMNUHFYGZ-UHFFFAOYSA-N 0.000 claims 2
- RQRAZBCPWDTVMS-UHFFFAOYSA-N CN(CC1CCOCC1)Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(CC1CCOCC1)Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 RQRAZBCPWDTVMS-UHFFFAOYSA-N 0.000 claims 2
- YYMRHMHLMILANH-UHFFFAOYSA-N CN(CCC(=O)N(C)C)Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(CCC(=O)N(C)C)Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 YYMRHMHLMILANH-UHFFFAOYSA-N 0.000 claims 2
- HPWLVIKNZMWHMW-UHFFFAOYSA-N CN(CCN1CCOCC1)Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(CCN1CCOCC1)Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 HPWLVIKNZMWHMW-UHFFFAOYSA-N 0.000 claims 2
- SVTCDTKVIMHMRG-UHFFFAOYSA-N CN(CCO)Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN(CCO)Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 SVTCDTKVIMHMRG-UHFFFAOYSA-N 0.000 claims 2
- ZNOKDBUVMGEYJK-UHFFFAOYSA-N CN(Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)CC(F)(F)F Chemical compound CN(Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)CC(F)(F)F ZNOKDBUVMGEYJK-UHFFFAOYSA-N 0.000 claims 2
- FFOMIGKVFKWKMB-UHFFFAOYSA-N CN(Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)CC1(C)COC1 Chemical compound CN(Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)CC1(C)COC1 FFOMIGKVFKWKMB-UHFFFAOYSA-N 0.000 claims 2
- BAGVSIJIMODSFE-UHFFFAOYSA-N CN1CCC(CC1)OCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN1CCC(CC1)OCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 BAGVSIJIMODSFE-UHFFFAOYSA-N 0.000 claims 2
- DPTFWRSCJAYLAY-UHFFFAOYSA-N CN1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CN1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 DPTFWRSCJAYLAY-UHFFFAOYSA-N 0.000 claims 2
- IPEVSUSIIMIGSO-UHFFFAOYSA-N CN1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound CN1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 IPEVSUSIIMIGSO-UHFFFAOYSA-N 0.000 claims 2
- OVBBNIXJCLXVIX-UHFFFAOYSA-N CN1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1(C)C Chemical compound CN1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1(C)C OVBBNIXJCLXVIX-UHFFFAOYSA-N 0.000 claims 2
- UHWSIPIWDVZPCY-UHFFFAOYSA-N CN1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1=O Chemical compound CN1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1=O UHWSIPIWDVZPCY-UHFFFAOYSA-N 0.000 claims 2
- FWFHFHJNFQXKCB-UHFFFAOYSA-N CNCCN(C)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CNCCN(C)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 FWFHFHJNFQXKCB-UHFFFAOYSA-N 0.000 claims 2
- VXEHXUUJMQYUEP-UHFFFAOYSA-N COC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCC(F)(F)CC4)c3c2o1 Chemical compound COC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCC(F)(F)CC4)c3c2o1 VXEHXUUJMQYUEP-UHFFFAOYSA-N 0.000 claims 2
- RVFLBXLYJNCZLB-UHFFFAOYSA-N COC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 RVFLBXLYJNCZLB-UHFFFAOYSA-N 0.000 claims 2
- WOXPQDGTEUVKPX-UHFFFAOYSA-N COC1(C)CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound COC1(C)CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 WOXPQDGTEUVKPX-UHFFFAOYSA-N 0.000 claims 2
- YMQGYGNCIPZINZ-UHFFFAOYSA-N COC1CCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COC1CCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 YMQGYGNCIPZINZ-UHFFFAOYSA-N 0.000 claims 2
- ARGKNCNIOPDUPF-UHFFFAOYSA-N COC1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COC1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 ARGKNCNIOPDUPF-UHFFFAOYSA-N 0.000 claims 2
- KNVPZEWSXMALEI-UHFFFAOYSA-N COC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound COC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 KNVPZEWSXMALEI-UHFFFAOYSA-N 0.000 claims 2
- ATCSRJSULPXISI-UHFFFAOYSA-N COC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound COC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 ATCSRJSULPXISI-UHFFFAOYSA-N 0.000 claims 2
- XGNZFUAGLNUMQL-UHFFFAOYSA-N COC1CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound COC1CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 XGNZFUAGLNUMQL-UHFFFAOYSA-N 0.000 claims 2
- XZYPHHPBEPRXCN-UHFFFAOYSA-N COC1CN(Cc2nc3cc(F)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound COC1CN(Cc2nc3cc(F)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 XZYPHHPBEPRXCN-UHFFFAOYSA-N 0.000 claims 2
- LERDESJWAYKMII-UHFFFAOYSA-N COCC1(CCOCC1)NC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COCC1(CCOCC1)NC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 LERDESJWAYKMII-UHFFFAOYSA-N 0.000 claims 2
- OUGCKETVVKRZEC-UHFFFAOYSA-N COCC1(CCOCC1)NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COCC1(CCOCC1)NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 OUGCKETVVKRZEC-UHFFFAOYSA-N 0.000 claims 2
- JNLDRTLPGIFSAO-UHFFFAOYSA-N COCC1CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound COCC1CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 JNLDRTLPGIFSAO-UHFFFAOYSA-N 0.000 claims 2
- BDEURKVDTJZGOE-UHFFFAOYSA-N COCCN1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COCCN1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 BDEURKVDTJZGOE-UHFFFAOYSA-N 0.000 claims 2
- KSHKBKWJDOALKZ-UHFFFAOYSA-N COCCNC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COCCNC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 KSHKBKWJDOALKZ-UHFFFAOYSA-N 0.000 claims 2
- BGIJVHSZAJOXOK-UHFFFAOYSA-N COCCNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COCCNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 BGIJVHSZAJOXOK-UHFFFAOYSA-N 0.000 claims 2
- TYHBCTKWGDGDJW-UHFFFAOYSA-N COCCNCc1nc2cc(F)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COCCNCc1nc2cc(F)c3NC(=O)NC4(CCCCC4)c3c2o1 TYHBCTKWGDGDJW-UHFFFAOYSA-N 0.000 claims 2
- KTOBLQFRGCNHNC-UHFFFAOYSA-N COCCOC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound COCCOC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 KTOBLQFRGCNHNC-UHFFFAOYSA-N 0.000 claims 2
- OASAOHGJWXCSMO-UHFFFAOYSA-N COCCOCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COCCOCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 OASAOHGJWXCSMO-UHFFFAOYSA-N 0.000 claims 2
- VHYQTCJNGUSZLD-UHFFFAOYSA-N COCCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COCCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 VHYQTCJNGUSZLD-UHFFFAOYSA-N 0.000 claims 2
- BWCGYWIASOYHLX-LBPRGKRZSA-N COC[C@@H]1CCCN1C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COC[C@@H]1CCCN1C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 BWCGYWIASOYHLX-LBPRGKRZSA-N 0.000 claims 2
- GTZXIJDBOPPRMB-GFCCVEGCSA-N COC[C@@H]1CCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COC[C@@H]1CCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 GTZXIJDBOPPRMB-GFCCVEGCSA-N 0.000 claims 2
- HEYZQXUNFNWJGC-CYBMUJFWSA-N COC[C@@H]1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound COC[C@@H]1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 HEYZQXUNFNWJGC-CYBMUJFWSA-N 0.000 claims 2
- ZJNVLQGURPOTKA-CYBMUJFWSA-N COC[C@H]1CCCN1Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COC[C@H]1CCCN1Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 ZJNVLQGURPOTKA-CYBMUJFWSA-N 0.000 claims 2
- GTZXIJDBOPPRMB-LBPRGKRZSA-N COC[C@H]1CCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COC[C@H]1CCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 GTZXIJDBOPPRMB-LBPRGKRZSA-N 0.000 claims 2
- CZTSYXORDMTSPA-UHFFFAOYSA-N COCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 CZTSYXORDMTSPA-UHFFFAOYSA-N 0.000 claims 2
- WDWRKOLWNQJXDH-CYBMUJFWSA-N CO[C@@H]1CCCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound CO[C@@H]1CCCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 WDWRKOLWNQJXDH-CYBMUJFWSA-N 0.000 claims 2
- YMQGYGNCIPZINZ-LLVKDONJSA-N CO[C@@H]1CCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CO[C@@H]1CCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 YMQGYGNCIPZINZ-LLVKDONJSA-N 0.000 claims 2
- KNVPZEWSXMALEI-GFCCVEGCSA-N CO[C@@H]1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound CO[C@@H]1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 KNVPZEWSXMALEI-GFCCVEGCSA-N 0.000 claims 2
- YMQGYGNCIPZINZ-NSHDSACASA-N CO[C@H]1CCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CO[C@H]1CCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 YMQGYGNCIPZINZ-NSHDSACASA-N 0.000 claims 2
- KNVPZEWSXMALEI-LBPRGKRZSA-N CO[C@H]1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound CO[C@H]1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 KNVPZEWSXMALEI-LBPRGKRZSA-N 0.000 claims 2
- QQZQSCCFCMZLEB-UHFFFAOYSA-N COc1ccc(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)c(OC)c1 Chemical compound COc1ccc(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)c(OC)c1 QQZQSCCFCMZLEB-UHFFFAOYSA-N 0.000 claims 2
- DEOSPVFPBZLHMZ-UHFFFAOYSA-N Cc1ccc(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)cn1 Chemical compound Cc1ccc(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)cn1 DEOSPVFPBZLHMZ-UHFFFAOYSA-N 0.000 claims 2
- ABZSBYHWNCSIHL-UHFFFAOYSA-N Cc1nc2cc(Cl)c3NC(=O)NC4(CCC(C)(C)CC4)c3c2o1 Chemical compound Cc1nc2cc(Cl)c3NC(=O)NC4(CCC(C)(C)CC4)c3c2o1 ABZSBYHWNCSIHL-UHFFFAOYSA-N 0.000 claims 2
- YXZJDVODZKCVNW-UHFFFAOYSA-N Cc1nc2cc(Cl)c3NC(=O)NC4(CCC(F)(F)CC4)c3c2o1 Chemical compound Cc1nc2cc(Cl)c3NC(=O)NC4(CCC(F)(F)CC4)c3c2o1 YXZJDVODZKCVNW-UHFFFAOYSA-N 0.000 claims 2
- YRVJRPWICRHMFX-UHFFFAOYSA-N Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 YRVJRPWICRHMFX-UHFFFAOYSA-N 0.000 claims 2
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims 2
- RAMBIRYOZCDNFX-UHFFFAOYSA-N ClCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound ClCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 RAMBIRYOZCDNFX-UHFFFAOYSA-N 0.000 claims 2
- BNADDZLMSJPFFQ-UHFFFAOYSA-N Clc1cc2nc(CN3CCC(=O)CC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN3CCC(=O)CC3)oc2c2c1NC(=O)NC21CCCCC1 BNADDZLMSJPFFQ-UHFFFAOYSA-N 0.000 claims 2
- REPXNUHCTZPERY-UHFFFAOYSA-N Clc1cc2nc(CN3CCC(CC3)OCC3CC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN3CCC(CC3)OCC3CC3)oc2c2c1NC(=O)NC21CCCCC1 REPXNUHCTZPERY-UHFFFAOYSA-N 0.000 claims 2
- AVWKZPRTPDVMNP-UHFFFAOYSA-N Clc1cc2nc(CN3CCC4(CCOC4)CC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN3CCC4(CCOC4)CC3)oc2c2c1NC(=O)NC21CCCCC1 AVWKZPRTPDVMNP-UHFFFAOYSA-N 0.000 claims 2
- ZVOXRCPYKCLIRP-UHFFFAOYSA-N Clc1cc2nc(CN3CCC4(COC4)CC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN3CCC4(COC4)CC3)oc2c2c1NC(=O)NC21CCCCC1 ZVOXRCPYKCLIRP-UHFFFAOYSA-N 0.000 claims 2
- YCRYGJBEJYNUEB-UHFFFAOYSA-N Clc1cc2nc(CN3CCCC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN3CCCC3)oc2c2c1NC(=O)NC21CCCCC1 YCRYGJBEJYNUEB-UHFFFAOYSA-N 0.000 claims 2
- VEDWYQAUJRRZGQ-UHFFFAOYSA-N Clc1cc2nc(CN3CCNCC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN3CCNCC3)oc2c2c1NC(=O)NC21CCCCC1 VEDWYQAUJRRZGQ-UHFFFAOYSA-N 0.000 claims 2
- BLPRCWYYFVZWGB-UHFFFAOYSA-N Clc1cc2nc(CN3CCOC4(CCCC4)C3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN3CCOC4(CCCC4)C3)oc2c2c1NC(=O)NC21CCCCC1 BLPRCWYYFVZWGB-UHFFFAOYSA-N 0.000 claims 2
- GWECUNZFOJPUBU-UHFFFAOYSA-N Clc1cc2nc(CN3CCOCC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN3CCOCC3)oc2c2c1NC(=O)NC21CCCCC1 GWECUNZFOJPUBU-UHFFFAOYSA-N 0.000 claims 2
- NOIMHMBKUJDEEE-UHFFFAOYSA-N Clc1cc2nc(CNC3(CCOCC3)C3CC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNC3(CCOCC3)C3CC3)oc2c2c1NC(=O)NC21CCCCC1 NOIMHMBKUJDEEE-UHFFFAOYSA-N 0.000 claims 2
- BFELRVJQWWUGTP-UHFFFAOYSA-N Clc1cc2nc(CNC3CC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNC3CC3)oc2c2c1NC(=O)NC21CCCCC1 BFELRVJQWWUGTP-UHFFFAOYSA-N 0.000 claims 2
- WGNUHKDOAXYCRK-UHFFFAOYSA-N Clc1cc2nc(CNC3CCCOC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNC3CCCOC3)oc2c2c1NC(=O)NC21CCCCC1 WGNUHKDOAXYCRK-UHFFFAOYSA-N 0.000 claims 2
- GYIAWVVUTARCCR-UHFFFAOYSA-N Clc1cc2nc(CNC3CCCOCC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNC3CCCOCC3)oc2c2c1NC(=O)NC21CCCCC1 GYIAWVVUTARCCR-UHFFFAOYSA-N 0.000 claims 2
- LVSFYXBIARTPQI-UHFFFAOYSA-N Clc1cc2nc(CNC3CCOCC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNC3CCOCC3)oc2c2c1NC(=O)NC21CCCCC1 LVSFYXBIARTPQI-UHFFFAOYSA-N 0.000 claims 2
- UFKZZNTVEBUUQC-UHFFFAOYSA-N Clc1cc2nc(CNCC3CCCCN3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNCC3CCCCN3)oc2c2c1NC(=O)NC21CCCCC1 UFKZZNTVEBUUQC-UHFFFAOYSA-N 0.000 claims 2
- TUILLJVVSKGXBH-UHFFFAOYSA-N Clc1cc2nc(CNCC3CCCCO3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNCC3CCCCO3)oc2c2c1NC(=O)NC21CCCCC1 TUILLJVVSKGXBH-UHFFFAOYSA-N 0.000 claims 2
- POUDEVAPECAQTG-UHFFFAOYSA-N Clc1cc2nc(CNCC3CCOC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNCC3CCOC3)oc2c2c1NC(=O)NC21CCCCC1 POUDEVAPECAQTG-UHFFFAOYSA-N 0.000 claims 2
- PEIYUCCFPHVXEI-UHFFFAOYSA-N Clc1cc2nc(CNCC3CCOCC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNCC3CCOCC3)oc2c2c1NC(=O)NC21CCCCC1 PEIYUCCFPHVXEI-UHFFFAOYSA-N 0.000 claims 2
- IDTFMMZCUIPMSS-UHFFFAOYSA-N Clc1cc2nc(CNCC3COC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNCC3COC3)oc2c2c1NC(=O)NC21CCCCC1 IDTFMMZCUIPMSS-UHFFFAOYSA-N 0.000 claims 2
- POUDEVAPECAQTG-LBPRGKRZSA-N Clc1cc2nc(CNC[C@@H]3CCOC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNC[C@@H]3CCOC3)oc2c2c1NC(=O)NC21CCCCC1 POUDEVAPECAQTG-LBPRGKRZSA-N 0.000 claims 2
- POUDEVAPECAQTG-GFCCVEGCSA-N Clc1cc2nc(CNC[C@H]3CCOC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNC[C@H]3CCOC3)oc2c2c1NC(=O)NC21CCCCC1 POUDEVAPECAQTG-GFCCVEGCSA-N 0.000 claims 2
- JFJDDWJFBCUKMS-UHFFFAOYSA-N Clc1cc2nc(CNCc3ccccn3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNCc3ccccn3)oc2c2c1NC(=O)NC21CCCCC1 JFJDDWJFBCUKMS-UHFFFAOYSA-N 0.000 claims 2
- WZSZFTWIOHGMJI-UHFFFAOYSA-N Clc1cc2nc(CNCc3cnco3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNCc3cnco3)oc2c2c1NC(=O)NC21CCCCC1 WZSZFTWIOHGMJI-UHFFFAOYSA-N 0.000 claims 2
- RHQOXOLGJJMUPG-UHFFFAOYSA-N Clc1cc2nc(CNCc3cocn3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNCc3cocn3)oc2c2c1NC(=O)NC21CCCCC1 RHQOXOLGJJMUPG-UHFFFAOYSA-N 0.000 claims 2
- MAIMOHJSHDMMMC-UHFFFAOYSA-N Clc1cc2nc(CNCc3ncccn3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNCc3ncccn3)oc2c2c1NC(=O)NC21CCCCC1 MAIMOHJSHDMMMC-UHFFFAOYSA-N 0.000 claims 2
- FTAWPMDZYMRMDZ-UHFFFAOYSA-N Clc1cc2nc(CNCc3ncco3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNCc3ncco3)oc2c2c1NC(=O)NC21CCCCC1 FTAWPMDZYMRMDZ-UHFFFAOYSA-N 0.000 claims 2
- WGNUHKDOAXYCRK-GFCCVEGCSA-N Clc1cc2nc(CN[C@@H]3CCCOC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN[C@@H]3CCCOC3)oc2c2c1NC(=O)NC21CCCCC1 WGNUHKDOAXYCRK-GFCCVEGCSA-N 0.000 claims 2
- IOIUPJUTDZQTPQ-LLVKDONJSA-N Clc1cc2nc(CN[C@@H]3CCOC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN[C@@H]3CCOC3)oc2c2c1NC(=O)NC21CCCCC1 IOIUPJUTDZQTPQ-LLVKDONJSA-N 0.000 claims 2
- OCTDCRPAJJRVMI-UHFFFAOYSA-N Clc1cc2nc(COC3CCOCC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(COC3CCOCC3)oc2c2c1NC(=O)NC21CCCCC1 OCTDCRPAJJRVMI-UHFFFAOYSA-N 0.000 claims 2
- ULLGOTMRFOXPBC-UHFFFAOYSA-N Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)N1CCNCC1 Chemical compound Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)N1CCNCC1 ULLGOTMRFOXPBC-UHFFFAOYSA-N 0.000 claims 2
- GEMPSKPTBAOTIY-UHFFFAOYSA-N Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)N1CCOCC1 Chemical compound Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)N1CCOCC1 GEMPSKPTBAOTIY-UHFFFAOYSA-N 0.000 claims 2
- VFCCQPBNFFIXPF-UHFFFAOYSA-N Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)NC1CCCOC1 Chemical compound Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)NC1CCCOC1 VFCCQPBNFFIXPF-UHFFFAOYSA-N 0.000 claims 2
- XHLPARWUEBPBCR-NSHDSACASA-N Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)NC[C@@H]1CCOC1 Chemical compound Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)NC[C@@H]1CCOC1 XHLPARWUEBPBCR-NSHDSACASA-N 0.000 claims 2
- XHLPARWUEBPBCR-LLVKDONJSA-N Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)NC[C@H]1CCOC1 Chemical compound Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)NC[C@H]1CCOC1 XHLPARWUEBPBCR-LLVKDONJSA-N 0.000 claims 2
- DIPUAEGDQZALTE-SNVBAGLBSA-N Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)N[C@@H]1CCOC1 Chemical compound Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)N[C@@H]1CCOC1 DIPUAEGDQZALTE-SNVBAGLBSA-N 0.000 claims 2
- DIPUAEGDQZALTE-JTQLQIEISA-N Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)N[C@H]1CCOC1 Chemical compound Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C(=O)N[C@H]1CCOC1 DIPUAEGDQZALTE-JTQLQIEISA-N 0.000 claims 2
- 101100407335 Dictyostelium discoideum pde7 gene Proteins 0.000 claims 2
- WTPGBIMYJVNIMF-UHFFFAOYSA-N FC(F)(CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)C1CCC1 Chemical compound FC(F)(CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)C1CCC1 WTPGBIMYJVNIMF-UHFFFAOYSA-N 0.000 claims 2
- PJXVEUVUERTMKY-UHFFFAOYSA-N FC(F)(F)CN1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound FC(F)(F)CN1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 PJXVEUVUERTMKY-UHFFFAOYSA-N 0.000 claims 2
- GQMNBSMLPDTZHE-UHFFFAOYSA-N FC(F)(F)CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound FC(F)(F)CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 GQMNBSMLPDTZHE-UHFFFAOYSA-N 0.000 claims 2
- FERXUDICJXZUFQ-UHFFFAOYSA-N FC(F)(F)OCCNC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound FC(F)(F)OCCNC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 FERXUDICJXZUFQ-UHFFFAOYSA-N 0.000 claims 2
- ZFYKZUADYWSKFR-UHFFFAOYSA-N FC(F)(F)OCCNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound FC(F)(F)OCCNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 ZFYKZUADYWSKFR-UHFFFAOYSA-N 0.000 claims 2
- FXUHNPVUBJAIPV-UHFFFAOYSA-N FC(F)CN1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound FC(F)CN1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 FXUHNPVUBJAIPV-UHFFFAOYSA-N 0.000 claims 2
- AEDOPYXQFKYVOX-UHFFFAOYSA-N FC(F)CN1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound FC(F)CN1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 AEDOPYXQFKYVOX-UHFFFAOYSA-N 0.000 claims 2
- BDKYXQINXVXUQV-UHFFFAOYSA-N FC1(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)COC1 Chemical compound FC1(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)COC1 BDKYXQINXVXUQV-UHFFFAOYSA-N 0.000 claims 2
- KETBOQMSAUFRIM-UHFFFAOYSA-N FC1(F)CCC(CC1)NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound FC1(F)CCC(CC1)NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 KETBOQMSAUFRIM-UHFFFAOYSA-N 0.000 claims 2
- AGYWJFDCNBZPIW-QWRGUYRKSA-N FC1(F)CCC2(CC1)NC(=O)Nc1c(Cl)cc3nc(CN4C[C@@H]5C[C@H]4CO5)oc3c21 Chemical compound FC1(F)CCC2(CC1)NC(=O)Nc1c(Cl)cc3nc(CN4C[C@@H]5C[C@H]4CO5)oc3c21 AGYWJFDCNBZPIW-QWRGUYRKSA-N 0.000 claims 2
- UDQPIOGEZNKKGQ-UHFFFAOYSA-N FC1(F)CCCC1NC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound FC1(F)CCCC1NC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 UDQPIOGEZNKKGQ-UHFFFAOYSA-N 0.000 claims 2
- RWDMMFIFMTXZFQ-UHFFFAOYSA-N FC1(F)CCCC1NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound FC1(F)CCCC1NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 RWDMMFIFMTXZFQ-UHFFFAOYSA-N 0.000 claims 2
- YOQDMRCFFAZKBM-UHFFFAOYSA-N FC1(F)CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound FC1(F)CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 YOQDMRCFFAZKBM-UHFFFAOYSA-N 0.000 claims 2
- PERBXBZQQBYHBX-UHFFFAOYSA-N FC1(F)CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound FC1(F)CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 PERBXBZQQBYHBX-UHFFFAOYSA-N 0.000 claims 2
- FXOJBFWVDYFKTE-UHFFFAOYSA-N FC1(F)CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound FC1(F)CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 FXOJBFWVDYFKTE-UHFFFAOYSA-N 0.000 claims 2
- UKLWEBWVTVVMPY-UHFFFAOYSA-N FC1CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound FC1CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 UKLWEBWVTVVMPY-UHFFFAOYSA-N 0.000 claims 2
- AJNFBAIHADAWNK-UHFFFAOYSA-N FC1COCCC1NC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound FC1COCCC1NC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 AJNFBAIHADAWNK-UHFFFAOYSA-N 0.000 claims 2
- XMKOORKSNUTGNW-UHFFFAOYSA-N FC1COCCC1NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound FC1COCCC1NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 XMKOORKSNUTGNW-UHFFFAOYSA-N 0.000 claims 2
- URSXNTNLKASGEZ-UHFFFAOYSA-N FCCN1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound FCCN1CCN(CC1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 URSXNTNLKASGEZ-UHFFFAOYSA-N 0.000 claims 2
- QASXPHDAPNNZEO-UHFFFAOYSA-N Fc1cc2nc(CN3CCC(F)(F)CC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Fc1cc2nc(CN3CCC(F)(F)CC3)oc2c2c1NC(=O)NC21CCCCC1 QASXPHDAPNNZEO-UHFFFAOYSA-N 0.000 claims 2
- JVNSAWOWPRIODC-UHFFFAOYSA-N Fc1ccc(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)nc1 Chemical compound Fc1ccc(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)nc1 JVNSAWOWPRIODC-UHFFFAOYSA-N 0.000 claims 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- KRLFQTNEFPAEGU-UHFFFAOYSA-N NC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound NC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 KRLFQTNEFPAEGU-UHFFFAOYSA-N 0.000 claims 2
- FPPMEESKCOHHEZ-UHFFFAOYSA-N OC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound OC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 FPPMEESKCOHHEZ-UHFFFAOYSA-N 0.000 claims 2
- JIETXOFEZXENGP-UHFFFAOYSA-N OC(CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)C(F)F Chemical compound OC(CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)C(F)F JIETXOFEZXENGP-UHFFFAOYSA-N 0.000 claims 2
- NMKKRAHQVWPZLC-UHFFFAOYSA-N OC(CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)C1CCCCC1 Chemical compound OC(CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1)C1CCCCC1 NMKKRAHQVWPZLC-UHFFFAOYSA-N 0.000 claims 2
- WJCJDNRIFLOPIS-UHFFFAOYSA-N OC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 Chemical compound OC1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CC1 WJCJDNRIFLOPIS-UHFFFAOYSA-N 0.000 claims 2
- KNEOCLBAATXIHG-UHFFFAOYSA-N OCC(F)(F)CNC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound OCC(F)(F)CNC(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 KNEOCLBAATXIHG-UHFFFAOYSA-N 0.000 claims 2
- NRBUQVASCARKOK-UHFFFAOYSA-N OCC(F)(F)CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound OCC(F)(F)CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 NRBUQVASCARKOK-UHFFFAOYSA-N 0.000 claims 2
- YUFJWCJHSIBZQT-UHFFFAOYSA-N OCC1(CCCC1)NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound OCC1(CCCC1)NCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 YUFJWCJHSIBZQT-UHFFFAOYSA-N 0.000 claims 2
- MTVPLYXTIRHFHB-UHFFFAOYSA-N OCC1CCCCN1Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound OCC1CCCCN1Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 MTVPLYXTIRHFHB-UHFFFAOYSA-N 0.000 claims 2
- IRFAEOLIIXNBBT-UHFFFAOYSA-N OCCNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound OCCNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 IRFAEOLIIXNBBT-UHFFFAOYSA-N 0.000 claims 2
- STDRATZIMUEVRF-GFCCVEGCSA-N OC[C@H]1CCCN1Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound OC[C@H]1CCCN1Cc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 STDRATZIMUEVRF-GFCCVEGCSA-N 0.000 claims 2
- RPCFFJCTDBENEF-UHFFFAOYSA-N OCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound OCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 RPCFFJCTDBENEF-UHFFFAOYSA-N 0.000 claims 2
- NBTCIFXNFOEVRV-LLVKDONJSA-N O[C@@H]1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound O[C@@H]1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 NBTCIFXNFOEVRV-LLVKDONJSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 2
- YNBLKTCWYSIBJX-UHFFFAOYSA-N [1,3]oxazolo[5,4-f]quinazoline Chemical compound N1=CN=CC2=C(OC=N3)C3=CC=C21 YNBLKTCWYSIBJX-UHFFFAOYSA-N 0.000 claims 2
- 230000007000 age related cognitive decline Effects 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 230000006870 function Effects 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims 2
- XJLSEXAGTJCILF-UHFFFAOYSA-N nipecotic acid Chemical compound OC(=O)C1CCCNC1 XJLSEXAGTJCILF-UHFFFAOYSA-N 0.000 claims 2
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims 2
- 230000002093 peripheral effect Effects 0.000 claims 2
- SRJOCJYGOFTFLH-UHFFFAOYSA-M piperidine-4-carboxylate Chemical compound [O-]C(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-M 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 230000019491 signal transduction Effects 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 230000009529 traumatic brain injury Effects 0.000 claims 2
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 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 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 208000029483 Acquired immunodeficiency Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- PXTPVHZZLWRZEP-UHFFFAOYSA-N CC(=O)Nc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CC(=O)Nc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 PXTPVHZZLWRZEP-UHFFFAOYSA-N 0.000 claims 1
- HJCJEJTYZLAKMJ-UHFFFAOYSA-N CC(C)CC1CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CCO1 Chemical compound CC(C)CC1CN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CCO1 HJCJEJTYZLAKMJ-UHFFFAOYSA-N 0.000 claims 1
- BNXHKKQWPUVYBB-UHFFFAOYSA-N CC(C)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CC(C)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 BNXHKKQWPUVYBB-UHFFFAOYSA-N 0.000 claims 1
- OCMMQYFWBWWQEY-UHFFFAOYSA-N CC1(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CCOC1 Chemical compound CC1(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)CCOC1 OCMMQYFWBWWQEY-UHFFFAOYSA-N 0.000 claims 1
- LLSIHFXPTCEMII-CYBMUJFWSA-N CCO[C@@H]1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound CCO[C@@H]1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 LLSIHFXPTCEMII-CYBMUJFWSA-N 0.000 claims 1
- YQJIUULRBMPDKE-UHFFFAOYSA-N CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CNCc1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 YQJIUULRBMPDKE-UHFFFAOYSA-N 0.000 claims 1
- GIFDLSSUWJWKLZ-UHFFFAOYSA-N COCCN(C)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COCCN(C)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 GIFDLSSUWJWKLZ-UHFFFAOYSA-N 0.000 claims 1
- ZQPJAEZSTXFUTP-UHFFFAOYSA-N COCCN(CCOC)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound COCCN(CCOC)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 ZQPJAEZSTXFUTP-UHFFFAOYSA-N 0.000 claims 1
- HEYZQXUNFNWJGC-ZDUSSCGKSA-N COC[C@H]1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 Chemical compound COC[C@H]1CCN(Cc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)C1 HEYZQXUNFNWJGC-ZDUSSCGKSA-N 0.000 claims 1
- SLZWOBGLJVSADN-GFCCVEGCSA-N CO[C@@H]1CCCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 Chemical compound CO[C@@H]1CCCN(C1)C(=O)c1nc2cc(Cl)c3NC(=O)NC4(CCCCC4)c3c2o1 SLZWOBGLJVSADN-GFCCVEGCSA-N 0.000 claims 1
- RZOCFOSQLRKLCI-UHFFFAOYSA-N COc1cncc(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)c1 Chemical compound COc1cncc(CNCc2nc3cc(Cl)c4NC(=O)NC5(CCCCC5)c4c3o2)c1 RZOCFOSQLRKLCI-UHFFFAOYSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- FBJBNJIKBFSJAW-UHFFFAOYSA-N Clc1cc2nc(CN3CC4CC3CO4)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN3CC4CC3CO4)oc2c2c1NC(=O)NC21CCCCC1 FBJBNJIKBFSJAW-UHFFFAOYSA-N 0.000 claims 1
- HABJOTATQRKJQJ-UHFFFAOYSA-N Clc1cc2nc(CN3CCN(CC3)C3COC3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN3CCN(CC3)C3COC3)oc2c2c1NC(=O)NC21CCCCC1 HABJOTATQRKJQJ-UHFFFAOYSA-N 0.000 claims 1
- FBJBNJIKBFSJAW-RYUDHWBXSA-N Clc1cc2nc(CN3C[C@@H]4C[C@H]3CO4)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN3C[C@@H]4C[C@H]3CO4)oc2c2c1NC(=O)NC21CCCCC1 FBJBNJIKBFSJAW-RYUDHWBXSA-N 0.000 claims 1
- FBJBNJIKBFSJAW-VXGBXAGGSA-N Clc1cc2nc(CN3C[C@H]4C[C@@H]3CO4)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CN3C[C@H]4C[C@@H]3CO4)oc2c2c1NC(=O)NC21CCCCC1 FBJBNJIKBFSJAW-VXGBXAGGSA-N 0.000 claims 1
- OBIOXMJYZCQLHB-UHFFFAOYSA-N Clc1cc2nc(CNCc3ccno3)oc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2nc(CNCc3ccno3)oc2c2c1NC(=O)NC21CCCCC1 OBIOXMJYZCQLHB-UHFFFAOYSA-N 0.000 claims 1
- MEVWUXDIWVHIRR-UHFFFAOYSA-N Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C1CC1 Chemical compound Clc1cc2nc(oc2c2c1NC(=O)NC21CCCCC1)C1CC1 MEVWUXDIWVHIRR-UHFFFAOYSA-N 0.000 claims 1
- HKLXTALRPUIMMS-UHFFFAOYSA-N Clc1cc2ncoc2c2c1NC(=O)NC21CCCCC1 Chemical compound Clc1cc2ncoc2c2c1NC(=O)NC21CCCCC1 HKLXTALRPUIMMS-UHFFFAOYSA-N 0.000 claims 1
- 208000015943 Coeliac disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 102000008130 Cyclic AMP-Dependent Protein Kinases Human genes 0.000 claims 1
- 108010049894 Cyclic AMP-Dependent Protein Kinases Proteins 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000012661 Dyskinesia Diseases 0.000 claims 1
- GMPHIQUOCYTWMS-NSHDSACASA-N FC1(F)CCC2(CC1)NC(=O)Nc1c(Cl)cc3nc(CNC[C@@H]4CCOC4)oc3c21 Chemical compound FC1(F)CCC2(CC1)NC(=O)Nc1c(Cl)cc3nc(CNC[C@@H]4CCOC4)oc3c21 GMPHIQUOCYTWMS-NSHDSACASA-N 0.000 claims 1
- GMPHIQUOCYTWMS-LLVKDONJSA-N FC1(F)CCC2(CC1)NC(=O)Nc1c(Cl)cc3nc(CNC[C@H]4CCOC4)oc3c21 Chemical compound FC1(F)CCC2(CC1)NC(=O)Nc1c(Cl)cc3nc(CNC[C@H]4CCOC4)oc3c21 GMPHIQUOCYTWMS-LLVKDONJSA-N 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 208000023661 Haematological disease Diseases 0.000 claims 1
- 208000016988 Hemorrhagic Stroke Diseases 0.000 claims 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 1
- 208000032382 Ischaemic stroke Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 206010061296 Motor dysfunction Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 102000001253 Protein Kinase Human genes 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 102000040945 Transcription factor Human genes 0.000 claims 1
- 108091023040 Transcription factor Proteins 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- PBIUUJCEMUAWJJ-UHFFFAOYSA-N azetidine-3-carbonitrile Chemical compound N#CC1CNC1 PBIUUJCEMUAWJJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 208000018300 basal ganglia disease Diseases 0.000 claims 1
- 102000023732 binding proteins Human genes 0.000 claims 1
- 108091008324 binding proteins Proteins 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000002491 encephalomyelitis Diseases 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 150000002240 furans Chemical class 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- 230000003483 hypokinetic effect Effects 0.000 claims 1
- 230000001900 immune effect Effects 0.000 claims 1
- 208000000509 infertility Diseases 0.000 claims 1
- 230000036512 infertility Effects 0.000 claims 1
- 231100000535 infertility Toxicity 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 208000020658 intracerebral hemorrhage Diseases 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 230000007074 memory dysfunction Effects 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000007658 neurological function Effects 0.000 claims 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 1
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
- 125000006308 propyl amino group Chemical group 0.000 claims 1
- 108060006633 protein kinase Proteins 0.000 claims 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-M pyrazine-2-carboxylate Chemical compound [O-]C(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-M 0.000 claims 1
- JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 230000004044 response Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- PYEZYNAHBMWJFR-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical compound N1=CC=C2S[C]=CC2=C1 PYEZYNAHBMWJFR-UHFFFAOYSA-N 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 230000000472 traumatic effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762531802P | 2017-07-12 | 2017-07-12 | |
| US62/531,802 | 2017-07-12 | ||
| PCT/US2018/041565 WO2019014305A1 (en) | 2017-07-12 | 2018-07-11 | SUBSTITUTED BENZOXAZOLE AND BENZOFURAN COMPOUNDS AS PDE7 INHIBITORS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020526546A JP2020526546A (ja) | 2020-08-31 |
| JP2020526546A5 true JP2020526546A5 (enExample) | 2021-08-12 |
| JP7213863B2 JP7213863B2 (ja) | 2023-01-27 |
Family
ID=63036485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020501229A Active JP7213863B2 (ja) | 2017-07-12 | 2018-07-11 | Ｐｄｅ７阻害剤としての置換ベンゾオキサゾール及びベンゾフラン化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US11685745B2 (enExample) |
| EP (1) | EP3652180B1 (enExample) |
| JP (1) | JP7213863B2 (enExample) |
| KR (1) | KR102640696B1 (enExample) |
| CN (1) | CN111094293B (enExample) |
| AU (1) | AU2018300091B2 (enExample) |
| CA (1) | CA3069432A1 (enExample) |
| MX (1) | MX2020000295A (enExample) |
| WO (1) | WO2019014305A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3652180B1 (en) | 2017-07-12 | 2023-11-29 | Dart NeuroScience, LLC | Substituted benzoxazole and benzofuran compounds as pde7 inhibitors |
| JP2022541954A (ja) * | 2019-07-17 | 2022-09-28 | 小野薬品工業株式会社 | Ｋｄｍ５阻害活性を有する化合物およびその医薬用途 |
| CN112574202B (zh) * | 2020-12-11 | 2021-11-09 | 台州学院 | 一种螺喹唑啉-2-酮类衍生物及其制备方法和应用 |
| CA3264002A1 (en) * | 2022-08-18 | 2024-02-22 | Mitodicure Gmbh | USE OF A THERAPEUTIC AGENT WITH PHOSPHODIESTERASE-7 INHIBITING ACTIVITY FOR THE TREATMENT AND PREVENTION OF DISEASES ASSOCIATED WITH CHRONIC FATIGUE, EXHAUSTION AND/OR EXERCISE INTOLERANCE |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| US7491742B2 (en) | 1999-10-21 | 2009-02-17 | Merck Patent Gmbh | Imidazole derivatives as phosphodiesterase VII inhibitors |
| DE19953025A1 (de) | 1999-11-04 | 2001-05-10 | Merck Patent Gmbh | Pyrrolderivate als Phosphodiesterase VII-Hemmer |
| DE19953024A1 (de) | 1999-11-04 | 2001-05-10 | Merck Patent Gmbh | Isoxazolderivate als Phosphodiesterase VII-Hemmer |
| DE19953414A1 (de) | 1999-11-06 | 2001-05-10 | Merck Patent Gmbh | Imidazopyridinderivate als Phospodiesterase VII-Hemmer |
| DE19954707A1 (de) | 1999-11-13 | 2001-05-17 | Merck Patent Gmbh | Imidazolverbindungen als Phosphodiesterase VII-Hemmer |
| US20030138815A1 (en) | 2000-04-28 | 2003-07-24 | Franz-Werner Kluxen | Splice variant of camp phosphodiesterase type7(pde7a3) |
| GB0015095D0 (en) | 2000-06-20 | 2000-08-09 | Celltech Chiroscience Ltd | Chemical compounds |
| CN100430401C (zh) | 2000-07-11 | 2008-11-05 | Amr科技公司 | 新的4-苯基取代的四氢异喹啉类化合物及其治疗用途 |
| US9931318B2 (en) | 2003-04-08 | 2018-04-03 | Dart Neuroscience (Cayman) Ltd. | Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation |
| US7868015B2 (en) | 2000-08-10 | 2011-01-11 | Cold Spring Harbor Laboratory | Phosphodiesesterase 4 inhibitors for the treatment of a cognitive deficit |
| PT1355669E (pt) | 2000-08-10 | 2012-01-02 | Cold Spring Harbor Lab | Treino cognitivo aumentado |
| AP1699A (en) * | 2001-03-21 | 2006-12-26 | Warner Lambert Co | New spirotricyclic derivatives and their use as phosphodiesterase-7 inhibitors |
| US6815448B2 (en) * | 2001-05-07 | 2004-11-09 | Wyeth | Azaheterocyclylmethyl derivatives of 7,8-dihydro-1,6,9-trioxa-3-aza-cyclopenta[a]naphthalene as 5-HT1A antagonists |
| EP1400244A1 (en) | 2002-09-17 | 2004-03-24 | Warner-Lambert Company LLC | New spirocondensed quinazolinones and their use as phosphodiesterase inhibitors |
| PT1775298E (pt) | 2004-07-01 | 2013-06-12 | Daiichi Sankyo Co Ltd | Derivado de tienopirazol com atividade inibidora da pde 7 |
| WO2006092691A1 (en) | 2005-03-01 | 2006-09-08 | Pfizer Limited | Use of pde7 inhibitors for the treatment of neuropathic pain |
| AU2006321349A1 (en) * | 2005-12-02 | 2007-06-07 | Pfizer Limited | Spirocyclic quinazoline derivatives as PDE7 inhibitors |
| AU2008254907A1 (en) | 2007-05-15 | 2008-11-27 | Helicon Therapeutics, Inc. | Methods of identifying genes involved in memory formation using small interfering RNA(siRNA) |
| CA2687944A1 (en) | 2007-05-24 | 2008-11-27 | Pfizer Limited | Spirocyclic quinazoline derivatives and their use as pde7 inhibitors |
| EP3652180B1 (en) | 2017-07-12 | 2023-11-29 | Dart NeuroScience, LLC | Substituted benzoxazole and benzofuran compounds as pde7 inhibitors |
-
2018
- 2018-07-11 EP EP18746513.3A patent/EP3652180B1/en active Active
- 2018-07-11 CN CN201880058047.XA patent/CN111094293B/zh active Active
- 2018-07-11 JP JP2020501229A patent/JP7213863B2/ja active Active
- 2018-07-11 US US16/629,922 patent/US11685745B2/en active Active
- 2018-07-11 CA CA3069432A patent/CA3069432A1/en active Pending
- 2018-07-11 KR KR1020207003770A patent/KR102640696B1/ko active Active
- 2018-07-11 MX MX2020000295A patent/MX2020000295A/es unknown
- 2018-07-11 AU AU2018300091A patent/AU2018300091B2/en active Active
- 2018-07-11 WO PCT/US2018/041565 patent/WO2019014305A1/en not_active Ceased
-
2023
- 2023-06-15 US US18/210,382 patent/US12319702B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2877146C (en) | Substituted thiophene- and furan-fused azolopyrimidine-5-(6h)-one compounds | |
| CN112867712B (zh) | 作为泛素特异性蛋白酶抑制剂的羧酰胺 | |
| CN111655695B (zh) | 作为pde1抑制剂的取代的呋喃并嘧啶化合物 | |
| JP2021503004A (ja) | 置換インドール化合物 | |
| JP2020526546A5 (enExample) | ||
| US12319702B2 (en) | Substituted benzoxazole and benzofuran compounds as PDE7 inhibitors | |
| AU2009212338A1 (en) | Furo-and Thieno[3,2-c] Pyridines | |
| CN115151534A (zh) | 白细胞介素-1受体相关激酶(irak)/fms样受体酪氨酸激酶(flt3)的抑制剂、其药物产品及其方法 | |
| JP2021504380A5 (enExample) | ||
| KR20220097434A (ko) | 톨 수용체 억제제로서의 치환된 피라졸 화합물 | |
| JP2025503463A (ja) | ブルトン型チロシンキナーゼ（ｂｔｋ）阻害剤をｅ３リガーゼリガンドにコンジュゲートすることによるｂｔｋの分解及び使用方法 | |
| TWI864633B (zh) | 作為iap拮抗劑的三環雜環化合物 | |
| AU2019286312B2 (en) | New isoxazolyl ether derivatives as GABA A alpha5 PAM | |
| CN118488947A (zh) | 稠环取代的六元杂环化合物及其制法和用途 | |
| AU2024286124A1 (en) | Bifunctional azines conjogates as selective degraders of smarca2 and therapeutic uses thereof | |
| RU2800160C2 (ru) | Новые производные простого эфира изоксазолила в качестве пам гамк a альфа5 |