ZA200201649B

ZA200201649B - Fused pyrrolecarboxamides: GABA brain receptor ligands.

Fused pyrrolecarboxamides: GABA brain receptor ligands. Download PDF

Info

Publication number: ZA200201649B
Authority: ZA; South Africa
Prior art keywords: alkyl; carboxamide; amino; phenyl; oxo
Prior art date: 1999-08-31

Application number

ZA200201649A

Other languages

English (en)

Inventor

Pamela Albaugh

Kenneth Shaw

Alan Hutchison

Original Assignee

Neurogen Corp

Priority date

1999-08-31

Filing date

2002-02-27

Publication date

2003-05-28

2002-02-27 Application filed by Neurogen Corp filed Critical Neurogen Corp

2003-05-28 Publication of ZA200201649B publication Critical patent/ZA200201649B/en

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BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 title claims description 66
229960003692 gamma aminobutyric acid Drugs 0.000 title claims description 64
239000003446 ligand Substances 0.000 title description 9
RLOQBKJCOAXOLR-UHFFFAOYSA-N 1h-pyrrole-2-carboxamide Chemical class NC(=O)C1=CC=CN1 RLOQBKJCOAXOLR-UHFFFAOYSA-N 0.000 title description 6
210000004556 brain Anatomy 0.000 title description 4
125000000217 alkyl group Chemical group 0.000 claims description 445
150000001875 compounds Chemical class 0.000 claims description 246
239000001257 hydrogen Chemical group 0.000 claims description 206
229910052739 hydrogen Inorganic materials 0.000 claims description 206
-1 hydroxy, amino, benzyl Chemical group 0.000 claims description 171
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 145
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 142
125000003545 alkoxy group Chemical group 0.000 claims description 138
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 134
229910052736 halogen Inorganic materials 0.000 claims description 124
150000002367 halogens Chemical group 0.000 claims description 124
150000002431 hydrogen Chemical group 0.000 claims description 105
102000005962 receptors Human genes 0.000 claims description 69
108020003175 receptors Proteins 0.000 claims description 69
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 67
125000001424 substituent group Chemical group 0.000 claims description 63
229910052799 carbon Inorganic materials 0.000 claims description 60
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 53
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 51
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 39
125000004122 cyclic group Chemical group 0.000 claims description 39
229910052757 nitrogen Inorganic materials 0.000 claims description 36
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
125000000753 cycloalkyl group Chemical group 0.000 claims description 33
125000004043 oxo group Chemical group O=* 0.000 claims description 30
125000004093 cyano group Chemical group *C#N 0.000 claims description 26
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
229940049706 benzodiazepine Drugs 0.000 claims description 24
238000000034 method Methods 0.000 claims description 24
125000004663 dialkyl amino group Chemical group 0.000 claims description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 22
239000001301 oxygen Substances 0.000 claims description 22
229910052760 oxygen Inorganic materials 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 22
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
125000004076 pyridyl group Chemical group 0.000 claims description 20
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 18
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 18
230000000694 effects Effects 0.000 claims description 17
125000001072 heteroaryl group Chemical group 0.000 claims description 16
239000008194 pharmaceutical composition Substances 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 15
208000019901 Anxiety disease Diseases 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
231100000252 nontoxic Toxicity 0.000 claims description 13
230000003000 nontoxic effect Effects 0.000 claims description 13
125000003282 alkyl amino group Chemical group 0.000 claims description 11
230000036506 anxiety Effects 0.000 claims description 11
238000003556 assay Methods 0.000 claims description 11
125000002883 imidazolyl group Chemical group 0.000 claims description 11
208000019116 sleep disease Diseases 0.000 claims description 11
125000002947 alkylene group Chemical group 0.000 claims description 10
208000035475 disorder Diseases 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
150000001721 carbon Chemical group 0.000 claims description 9
208000010877 cognitive disease Diseases 0.000 claims description 9
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 8
238000000338 in vitro Methods 0.000 claims description 8
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000001041 indolyl group Chemical group 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
208000028698 Cognitive impairment Diseases 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000000842 isoxazolyl group Chemical group 0.000 claims description 6
125000003226 pyrazolyl group Chemical group 0.000 claims description 6
125000002098 pyridazinyl group Chemical group 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
125000000168 pyrrolyl group Chemical group 0.000 claims description 6
125000000335 thiazolyl group Chemical group 0.000 claims description 6
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
125000001786 isothiazolyl group Chemical group 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000002757 morpholinyl group Chemical group 0.000 claims description 5
125000002971 oxazolyl group Chemical group 0.000 claims description 5
125000003386 piperidinyl group Chemical group 0.000 claims description 5
150000003857 carboxamides Chemical class 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
125000003884 phenylalkyl group Chemical group 0.000 claims description 4
LSGKMZLPZFPAIN-UHFFFAOYSA-N 1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 claims description 3
125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 3
125000004193 piperazinyl group Chemical group 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
208000020685 sleep-wake disease Diseases 0.000 claims description 3
125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
AKWIAIDKXNKXDI-UHFFFAOYSA-N 1h-pyrrole-3-carboxamide Chemical compound NC(=O)C=1C=CNC=1 AKWIAIDKXNKXDI-UHFFFAOYSA-N 0.000 claims 21
230000008484 agonism Effects 0.000 claims 10
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 8
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 8
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 8
230000008485 antagonism Effects 0.000 claims 5
230000001717 pathogenic effect Effects 0.000 claims 4
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 3
TTXOHSURMRJLRU-UHFFFAOYSA-N 1h-pyrrole-3-carboxamide;hydrochloride Chemical compound Cl.NC(=O)C=1C=CNC=1 TTXOHSURMRJLRU-UHFFFAOYSA-N 0.000 claims 2
125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 2
125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 2
DJVCEDWZYTVJGQ-UHFFFAOYSA-N 4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1CCC(=O)C2=C1NC=C2C(=O)N DJVCEDWZYTVJGQ-UHFFFAOYSA-N 0.000 claims 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
KMAKOBLIOCQGJP-UHFFFAOYSA-N indole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CNC2=C1 KMAKOBLIOCQGJP-UHFFFAOYSA-N 0.000 claims 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 2
ILZGSELSFLCNAF-UHFFFAOYSA-N 1,2,3,3a,4,5-hexahydrocyclohepta[b]pyrrole-3-carboxamide Chemical compound N1C=2C(C(C1)C(=O)N)CCC=CC2 ILZGSELSFLCNAF-UHFFFAOYSA-N 0.000 claims 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
XCKPUFSDEYHSKM-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-indole-3-carboxamide Chemical compound C1=CCC2C(C(=O)N)CNC2=C1 XCKPUFSDEYHSKM-UHFFFAOYSA-N 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
XERBBQHVHYAUSF-UHFFFAOYSA-N 4-oxo-n-[4-(2-pyrrolidin-1-ylethoxy)pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC1=CN=CC=C1OCCN1CCCC1 XERBBQHVHYAUSF-UHFFFAOYSA-N 0.000 claims 1
WWFOZLVQVJLJPC-UHFFFAOYSA-N 4-oxo-n-[4-(2-pyrrolidin-1-ylethoxy)pyridin-3-yl]-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound C=1NC=2CCCCC(=O)C=2C=1C(=O)NC1=CN=CC=C1OCCN1CCCC1 WWFOZLVQVJLJPC-UHFFFAOYSA-N 0.000 claims 1
GXJPJPSEZPJCLB-UHFFFAOYSA-N 4-oxo-n-[4-(2-pyrrolidin-1-ylethoxy)pyridin-3-yl]-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide;hydrochloride Chemical compound Cl.C=1NC=2CCCCC(=O)C=2C=1C(=O)NC1=CN=CC=C1OCCN1CCCC1 GXJPJPSEZPJCLB-UHFFFAOYSA-N 0.000 claims 1
FJJDVLBBBKSGJX-UHFFFAOYSA-N 4-oxo-n-[4-(2-pyrrolidin-1-ylethyl)phenyl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC(C=C1)=CC=C1CCN1CCCC1 FJJDVLBBBKSGJX-UHFFFAOYSA-N 0.000 claims 1
NVHWFYGQNCBPGV-UHFFFAOYSA-N 4-oxo-n-[4-[2-(2-pyrrolidin-1-ylethoxy)ethoxy]pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC1=CN=CC=C1OCCOCCN1CCCC1 NVHWFYGQNCBPGV-UHFFFAOYSA-N 0.000 claims 1
NCEAEUVGVIMDTB-UHFFFAOYSA-N 4-oxo-n-[4-[2-(propan-2-ylamino)ethoxy]phenyl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCCNC(C)C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 NCEAEUVGVIMDTB-UHFFFAOYSA-N 0.000 claims 1
IQUBJCDKEDETJG-UHFFFAOYSA-N 4-oxo-n-[4-[2-(propan-2-ylamino)ethoxy]pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound CC(C)NCCOC1=CC=NC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 IQUBJCDKEDETJG-UHFFFAOYSA-N 0.000 claims 1
DRAQIHXURAGEAM-UHFFFAOYSA-N 4-oxo-n-[4-[2-(propylamino)ethoxy]pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound CCCNCCOC1=CC=NC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 DRAQIHXURAGEAM-UHFFFAOYSA-N 0.000 claims 1
MLWALNIOJBDNPP-UHFFFAOYSA-N 4-oxo-n-[4-[3-(pentylamino)propoxy]phenyl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=CC(OCCCNCCCCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 MLWALNIOJBDNPP-UHFFFAOYSA-N 0.000 claims 1
BCFRNHUICWULJW-UHFFFAOYSA-N 4-oxo-n-[4-[3-(propylamino)propoxy]pyridin-3-yl]-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound CCCNCCCOC1=CC=NC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 BCFRNHUICWULJW-UHFFFAOYSA-N 0.000 claims 1
102100025514 ATP-dependent 6-phosphofructokinase, platelet type Human genes 0.000 claims 1
101710125293 ATP-dependent 6-phosphofructokinase, platelet type Proteins 0.000 claims 1
BHHMEPQOZNPFJD-UHFFFAOYSA-N C(C)OC1=NC=C(C(=C1)C)NC(=O)C1=CNC=2CCCC(C12)=O.CN(C(C)=O)CCNC1=NC=C(C=C1)NC(=O)C1=CNC=2CCCC(C12)=O Chemical compound C(C)OC1=NC=C(C(=C1)C)NC(=O)C1=CNC=2CCCC(C12)=O.CN(C(C)=O)CCNC1=NC=C(C=C1)NC(=O)C1=CNC=2CCCC(C12)=O BHHMEPQOZNPFJD-UHFFFAOYSA-N 0.000 claims 1
SDFDKKZWRHKDIR-UHFFFAOYSA-N C1CCCCC2=C1NC=C2C(=O)N Chemical compound C1CCCCC2=C1NC=C2C(=O)N SDFDKKZWRHKDIR-UHFFFAOYSA-N 0.000 claims 1
NUROHLOTVUVTSF-UHFFFAOYSA-N N-[2-(4-aminophenoxy)ethyl]thiophene-2-sulfonamide Chemical compound C1=CC(N)=CC=C1OCCNS(=O)(=O)C1=CC=CS1 NUROHLOTVUVTSF-UHFFFAOYSA-N 0.000 claims 1
150000001408 amides Chemical class 0.000 claims 1
YZHJISPIBWKWGY-UHFFFAOYSA-N cp-615,003 Chemical compound C1=C(F)C(OCCNCCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 YZHJISPIBWKWGY-UHFFFAOYSA-N 0.000 claims 1
FZORYZWSOORCGE-UHFFFAOYSA-N cyclohepta[b]pyrrole-3-carboxamide Chemical compound N1=C2C(C(=C1)C(=O)N)=CC=CC=C2 FZORYZWSOORCGE-UHFFFAOYSA-N 0.000 claims 1
125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims 1
BXCAIEPEDZJRPP-UHFFFAOYSA-N ethyl 2-[2-fluoro-4-[(4-oxo-1,5,6,7-tetrahydroindole-3-carbonyl)amino]phenoxy]acetate Chemical compound C1=C(F)C(OCC(=O)OCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 BXCAIEPEDZJRPP-UHFFFAOYSA-N 0.000 claims 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims 1
ODANAPRZCJKFHZ-UHFFFAOYSA-N n-[2-fluoro-4-[2-(2-methylpropylamino)ethoxy]phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound FC1=CC(OCCNCC(C)C)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 ODANAPRZCJKFHZ-UHFFFAOYSA-N 0.000 claims 1
UOOKATMZXWBBBK-UHFFFAOYSA-N n-[2-fluoro-4-[2-(propylamino)ethoxy]phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound FC1=CC(OCCNCCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 UOOKATMZXWBBBK-UHFFFAOYSA-N 0.000 claims 1
NTLYJLVDKNDSEP-UHFFFAOYSA-N n-[3-[2-(butylamino)ethoxy]phenyl]-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound CCCCNCCOC1=CC=CC(NC(=O)C=2C=3C(=O)CCCCC=3NC=2)=C1 NTLYJLVDKNDSEP-UHFFFAOYSA-N 0.000 claims 1
MXYCJMSEVPUSDL-UHFFFAOYSA-N n-[3-[2-(cyclopropylmethylamino)ethoxy]phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C=1NC=2CCCC(=O)C=2C=1C(=O)NC(C=1)=CC=CC=1OCCNCC1CC1 MXYCJMSEVPUSDL-UHFFFAOYSA-N 0.000 claims 1
DUJLLRDLZUMEDZ-UHFFFAOYSA-N n-[3-[2-[(4-methylcyclohexyl)amino]ethoxy]phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1CC(C)CCC1NCCOC1=CC=CC(NC(=O)C=2C=3C(=O)CCCC=3NC=2)=C1 DUJLLRDLZUMEDZ-UHFFFAOYSA-N 0.000 claims 1
KQABIIKCRNCCAH-UHFFFAOYSA-N n-[3-[3-(3-bicyclo[2.2.1]heptanylamino)propoxy]phenyl]-4-oxo-5,6,7,8-tetrahydro-1h-cyclohepta[b]pyrrole-3-carboxamide Chemical compound C1CCCC(=O)C2=C1NC=C2C(=O)NC1=CC=CC(OCCCNC2C3CCC(C3)C2)=C1 KQABIIKCRNCCAH-UHFFFAOYSA-N 0.000 claims 1
MOQGIRNTJOWSNQ-UHFFFAOYSA-N n-[3-fluoro-4-[2-(propylamino)ethoxy]phenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide;hydrochloride Chemical compound Cl.C1=C(F)C(OCCNCCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 MOQGIRNTJOWSNQ-UHFFFAOYSA-N 0.000 claims 1
JTNAVINOLPDSFE-UHFFFAOYSA-N n-[4-[(1-methylpyrrolidin-3-yl)methoxy]pyridin-3-yl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1N(C)CCC1COC1=CC=NC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 JTNAVINOLPDSFE-UHFFFAOYSA-N 0.000 claims 1
RUJBUPHBSVIIQL-UHFFFAOYSA-N n-[4-[2-(1-methylpyrrolidin-2-yl)ethoxy]pyridin-3-yl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound CN1CCCC1CCOC1=CC=NC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 RUJBUPHBSVIIQL-UHFFFAOYSA-N 0.000 claims 1
GRTYKDIGLIYUFW-UHFFFAOYSA-N n-[4-[2-(butylamino)ethoxy]-3-fluorophenyl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound C1=C(F)C(OCCNCCCC)=CC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 GRTYKDIGLIYUFW-UHFFFAOYSA-N 0.000 claims 1
QKYNOJCFMJGAHL-UHFFFAOYSA-N n-[4-[2-(butylamino)ethoxy]pyridin-3-yl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide Chemical compound CCCCNCCOC1=CC=NC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 QKYNOJCFMJGAHL-UHFFFAOYSA-N 0.000 claims 1
FLKXMJLRIAXPHS-UHFFFAOYSA-N n-[4-[2-(butylamino)ethoxy]pyridin-3-yl]-4-oxo-1,5,6,7-tetrahydroindole-3-carboxamide;hydrochloride Chemical compound Cl.CCCCNCCOC1=CC=NC=C1NC(=O)C1=CNC2=C1C(=O)CCC2 FLKXMJLRIAXPHS-UHFFFAOYSA-N 0.000 claims 1
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