JP2009221205A5 - - Google Patents
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- Publication number
- JP2009221205A5 JP2009221205A5 JP2009110392A JP2009110392A JP2009221205A5 JP 2009221205 A5 JP2009221205 A5 JP 2009221205A5 JP 2009110392 A JP2009110392 A JP 2009110392A JP 2009110392 A JP2009110392 A JP 2009110392A JP 2009221205 A5 JP2009221205 A5 JP 2009221205A5
- Authority
- JP
- Japan
- Prior art keywords
- indole
- carboxamide
- morpholin
- sulfonyl
- bromo
- 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
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- 125000000753 cycloalkyl group Chemical group 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 14
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 10
- -1 (aminocarbonyl) -3- (morpholin-4-ylsulfonyl) -1H-indole-5-carboxylate Chemical compound 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 7
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 4
- AOEOFSMAYKZDGD-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2,3-dihydro-1h-inden-1-yl)morpholine-2-carboxamide Chemical compound C1CC2=CC=CC=C2C1NC(=O)C(C1)OCCN1S(=O)(=O)C1=C(C(=O)N)NC2=CC=C(Br)C=C21 AOEOFSMAYKZDGD-UHFFFAOYSA-N 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- ISMBKJOFRDHUEK-UHFFFAOYSA-N (2-carbamoyl-3-morpholin-4-ylsulfonyl-1h-indol-5-yl) methanesulfonate Chemical compound C12=CC(OS(=O)(=O)C)=CC=C2NC(C(N)=O)=C1S(=O)(=O)N1CCOCC1 ISMBKJOFRDHUEK-UHFFFAOYSA-N 0.000 claims 1
- YEHZLTRBZWGIKK-UHFFFAOYSA-N 1-morpholin-4-ylsulfonylindole-2-carboxamide Chemical compound NC(=O)C1=CC2=CC=CC=C2N1S(=O)(=O)N1CCOCC1 YEHZLTRBZWGIKK-UHFFFAOYSA-N 0.000 claims 1
- JBCWXEDCYISNIJ-UHFFFAOYSA-N 3-(3-benzylpiperidin-1-yl)sulfonyl-5-chloro-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Cl)C=C2C=1S(=O)(=O)N(C1)CCCC1CC1=CC=CC=C1 JBCWXEDCYISNIJ-UHFFFAOYSA-N 0.000 claims 1
- RRFUFVAFDHNUSM-UHFFFAOYSA-N 3-(3-hydroxyazetidin-1-yl)sulfonyl-5-iodo-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(I)C=C2C=1S(=O)(=O)N1CC(O)C1 RRFUFVAFDHNUSM-UHFFFAOYSA-N 0.000 claims 1
- NVJJBPAWEMXLMX-UHFFFAOYSA-N 3-(4-acetylpiperazin-1-yl)sulfonyl-5-chloro-1h-indole-2-carboxamide Chemical compound C1CN(C(=O)C)CCN1S(=O)(=O)C1=C(C(N)=O)NC2=CC=C(Cl)C=C12 NVJJBPAWEMXLMX-UHFFFAOYSA-N 0.000 claims 1
- JWQGLPQMPIWPKQ-UHFFFAOYSA-N 3-(4-benzylpiperazin-1-yl)sulfonyl-5-chloro-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Cl)C=C2C=1S(=O)(=O)N(CC1)CCN1CC1=CC=CC=C1 JWQGLPQMPIWPKQ-UHFFFAOYSA-N 0.000 claims 1
- XAQDXLCTHDKRAI-UHFFFAOYSA-N 3-(azetidin-1-ylsulfonyl)-5-bromo-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N1CCC1 XAQDXLCTHDKRAI-UHFFFAOYSA-N 0.000 claims 1
- CQIBAQUOQBVTGN-UHFFFAOYSA-N 3-(azetidin-1-ylsulfonyl)-5-chloro-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Cl)C=C2C=1S(=O)(=O)N1CCC1 CQIBAQUOQBVTGN-UHFFFAOYSA-N 0.000 claims 1
- RBLJXUJZGKQZPF-UHFFFAOYSA-N 3-(azetidin-1-ylsulfonyl)-5-methoxy-1h-indole-2-carboxamide Chemical compound C12=CC(OC)=CC=C2NC(C(N)=O)=C1S(=O)(=O)N1CCC1 RBLJXUJZGKQZPF-UHFFFAOYSA-N 0.000 claims 1
- OVBCPNXFQRHAMT-FQEVSTJZSA-N 3-[(2s)-2-(phenoxymethyl)morpholin-4-yl]sulfonyl-7-(pyridin-4-ylmethylamino)-1h-indole-2-carboxamide Chemical compound C1=CC=C2C(S(=O)(=O)N3C[C@@H](COC=4C=CC=CC=4)OCC3)=C(C(=O)N)NC2=C1NCC1=CC=NC=C1 OVBCPNXFQRHAMT-FQEVSTJZSA-N 0.000 claims 1
- IYHAQCNPVUXRAI-UHFFFAOYSA-N 3-[(3-benzyl-1-oxa-8-azaspiro[4.5]decan-8-yl)sulfonyl]-5-chloro-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Cl)C=C2C=1S(=O)(=O)N(CC1)CCC1(OC1)CC1CC1=CC=CC=C1 IYHAQCNPVUXRAI-UHFFFAOYSA-N 0.000 claims 1
- KZHRPFUTQSSJBE-UHFFFAOYSA-N 3-[(7-benzyl-2,7-diazaspiro[4.4]nonan-2-yl)sulfonyl]-5-bromo-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCC1(C1)CCN1CC1=CC=CC=C1 KZHRPFUTQSSJBE-UHFFFAOYSA-N 0.000 claims 1
- MUGUDMNLPFNAQF-UHFFFAOYSA-N 3-[2-(3-benzylpyrrolidine-1-carbonyl)morpholin-4-yl]sulfonyl-5-bromo-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCOC1C(=O)N(C1)CCC1CC1=CC=CC=C1 MUGUDMNLPFNAQF-UHFFFAOYSA-N 0.000 claims 1
- MTYRLPSQQNKYAS-UHFFFAOYSA-N 3-[2-(4-benzylpiperazine-1-carbonyl)morpholin-4-yl]sulfonyl-5-bromo-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCOC1C(=O)N(CC1)CCN1CC1=CC=CC=C1 MTYRLPSQQNKYAS-UHFFFAOYSA-N 0.000 claims 1
- MBRUGKWBJSTANX-UHFFFAOYSA-N 3-[2-(azepane-1-carbonyl)morpholin-4-yl]sulfonyl-5-bromo-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCOC1C(=O)N1CCCCCC1 MBRUGKWBJSTANX-UHFFFAOYSA-N 0.000 claims 1
- WGNVYVFZSJTMSZ-UHFFFAOYSA-N 3-[2-[2-(1,3-benzothiazol-2-yl)pyrrolidine-1-carbonyl]morpholin-4-yl]sulfonyl-5-bromo-1h-indole-2-carboxamide Chemical compound C1=CC=C2SC(C3CCCN3C(=O)C3OCCN(C3)S(=O)(=O)C=3C4=CC(Br)=CC=C4NC=3C(=O)N)=NC2=C1 WGNVYVFZSJTMSZ-UHFFFAOYSA-N 0.000 claims 1
- NOKGMVYVOHQJRT-UHFFFAOYSA-N 3-[[2-(1-benzofuran-2-yl)-1-oxa-8-azaspiro[4.5]decan-8-yl]sulfonyl]-5-chloro-1h-indole-2-carboxamide Chemical compound C1=CC=C2OC(C3CCC4(CCN(CC4)S(=O)(=O)C=4C5=CC(Cl)=CC=C5NC=4C(=O)N)O3)=CC2=C1 NOKGMVYVOHQJRT-UHFFFAOYSA-N 0.000 claims 1
- TZKCGGDSNIAOTN-UHFFFAOYSA-N 3-morpholin-4-ylsulfonyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=CC=C2C=1S(=O)(=O)N1CCOCC1 TZKCGGDSNIAOTN-UHFFFAOYSA-N 0.000 claims 1
- JAZVOBCHQUTMDH-UHFFFAOYSA-N 3-morpholin-4-ylsulfonyl-5-(1,3-thiazol-2-yl)-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(C=3SC=CN=3)C=C2C=1S(=O)(=O)N1CCOCC1 JAZVOBCHQUTMDH-UHFFFAOYSA-N 0.000 claims 1
- KAGBSOQIBBXENC-UHFFFAOYSA-N 3-morpholin-4-ylsulfonyl-5-(1h-pyrrol-2-yl)-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(C=3NC=CC=3)C=C2C=1S(=O)(=O)N1CCOCC1 KAGBSOQIBBXENC-UHFFFAOYSA-N 0.000 claims 1
- RQSZDLAFSUUHRP-UHFFFAOYSA-N 3-morpholin-4-ylsulfonyl-5-(2-phenylethyl)-1h-indole-2-carboxamide Chemical compound C1=C2C(S(=O)(=O)N3CCOCC3)=C(C(=O)N)NC2=CC=C1CCC1=CC=CC=C1 RQSZDLAFSUUHRP-UHFFFAOYSA-N 0.000 claims 1
- XTZHLPUTPHINGK-UHFFFAOYSA-N 3-morpholin-4-ylsulfonyl-5-(2-phenylethynyl)-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(C#CC=3C=CC=CC=3)C=C2C=1S(=O)(=O)N1CCOCC1 XTZHLPUTPHINGK-UHFFFAOYSA-N 0.000 claims 1
- SLGNPJAIDFICGP-UHFFFAOYSA-N 3-morpholin-4-ylsulfonyl-5-[(2,2,2-trifluoroacetyl)amino]-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(NC(=O)C(F)(F)F)C=C2C=1S(=O)(=O)N1CCOCC1 SLGNPJAIDFICGP-UHFFFAOYSA-N 0.000 claims 1
- ATJXRQUNMXDJBI-UHFFFAOYSA-N 3-morpholin-4-ylsulfonyl-5-nitro-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C([N+]([O-])=O)C=C2C=1S(=O)(=O)N1CCOCC1 ATJXRQUNMXDJBI-UHFFFAOYSA-N 0.000 claims 1
- IVKJJTLXSYYIAB-UHFFFAOYSA-N 3-morpholin-4-ylsulfonyl-5-propan-2-yloxy-1h-indole-2-carboxamide Chemical compound C12=CC(OC(C)C)=CC=C2NC(C(N)=O)=C1S(=O)(=O)N1CCOCC1 IVKJJTLXSYYIAB-UHFFFAOYSA-N 0.000 claims 1
- JXFWMXQWUGXFTD-UHFFFAOYSA-N 3-morpholin-4-ylsulfonyl-5-propoxy-1h-indole-2-carboxamide Chemical compound C12=CC(OCCC)=CC=C2NC(C(N)=O)=C1S(=O)(=O)N1CCOCC1 JXFWMXQWUGXFTD-UHFFFAOYSA-N 0.000 claims 1
- FNMGVDUOBJKKAX-UHFFFAOYSA-N 3-morpholin-4-ylsulfonyl-5-pyridin-3-yl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(C=3C=NC=CC=3)C=C2C=1S(=O)(=O)N1CCOCC1 FNMGVDUOBJKKAX-UHFFFAOYSA-N 0.000 claims 1
- OLYOEGWFUNWSMF-UHFFFAOYSA-N 3-morpholin-4-ylsulfonyl-5-thiophen-2-yl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(C=3SC=CC=3)C=C2C=1S(=O)(=O)N1CCOCC1 OLYOEGWFUNWSMF-UHFFFAOYSA-N 0.000 claims 1
- ZBLWFCIIHLPMKI-UHFFFAOYSA-N 3-morpholin-4-ylsulfonyl-5-thiophen-3-yl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(C3=CSC=C3)C=C2C=1S(=O)(=O)N1CCOCC1 ZBLWFCIIHLPMKI-UHFFFAOYSA-N 0.000 claims 1
- JVRRGJZWNZDGEX-UHFFFAOYSA-N 3-morpholin-4-ylsulfonyl-7-(pyridin-4-ylmethylamino)-1h-indole-2-carboxamide Chemical compound C1=CC=C2C(S(=O)(=O)N3CCOCC3)=C(C(=O)N)NC2=C1NCC1=CC=NC=C1 JVRRGJZWNZDGEX-UHFFFAOYSA-N 0.000 claims 1
- HBFXUOQPARKSLD-UHFFFAOYSA-N 4,5-dibromo-3-morpholin-4-ylsulfonyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C(Br)=C2C=1S(=O)(=O)N1CCOCC1 HBFXUOQPARKSLD-UHFFFAOYSA-N 0.000 claims 1
- BEKHKDNSGSMOQK-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(1,2,3,4-tetrahydronaphthalen-2-ylmethyl)morpholine-2-carboxamide Chemical compound C1CC2=CC=CC=C2CC1CNC(=O)C(C1)OCCN1S(=O)(=O)C1=C(C(=O)N)NC2=CC=C(Br)C=C21 BEKHKDNSGSMOQK-UHFFFAOYSA-N 0.000 claims 1
- QRDUEQGKMQDVHK-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(1,2-diphenylethyl)morpholine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCOC1C(=O)NC(C=1C=CC=CC=1)CC1=CC=CC=C1 QRDUEQGKMQDVHK-UHFFFAOYSA-N 0.000 claims 1
- GCDSRNUXMDFBAE-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(1,4-dioxan-2-ylmethyl)morpholine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCOC1C(=O)NCC1COCCO1 GCDSRNUXMDFBAE-UHFFFAOYSA-N 0.000 claims 1
- QVMASHOLPSONNC-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(1-methoxypropan-2-yl)morpholine-2-carboxamide Chemical compound C1COC(C(=O)NC(C)COC)CN1S(=O)(=O)C1=C(C(N)=O)NC2=CC=C(Br)C=C12 QVMASHOLPSONNC-UHFFFAOYSA-N 0.000 claims 1
- OLGQPWOWVIAAPM-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(1-phenylcyclopropyl)morpholine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCOC1C(=O)NC1(C=2C=CC=CC=2)CC1 OLGQPWOWVIAAPM-UHFFFAOYSA-N 0.000 claims 1
- UNCPTNYTGPWAMP-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(1-phenylethyl)morpholine-2-carboxamide Chemical compound C1N(S(=O)(=O)C=2C3=CC(Br)=CC=C3NC=2C(N)=O)CCOC1C(=O)NC(C)C1=CC=CC=C1 UNCPTNYTGPWAMP-UHFFFAOYSA-N 0.000 claims 1
- YHJLTYHTFZRTKT-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2,2,3,3,4,4,4-heptafluorobutyl)morpholine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N1CCOC(C(=O)NCC(F)(F)C(F)(F)C(F)(F)F)C1 YHJLTYHTFZRTKT-UHFFFAOYSA-N 0.000 claims 1
- HRZSMWWNOKJDTJ-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2,2-dimethylpropyl)morpholine-2-carboxamide Chemical compound C1COC(C(=O)NCC(C)(C)C)CN1S(=O)(=O)C1=C(C(N)=O)NC2=CC=C(Br)C=C12 HRZSMWWNOKJDTJ-UHFFFAOYSA-N 0.000 claims 1
- XXCNDMSBINMSHM-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2,2-diphenylethyl)morpholine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCOC1C(=O)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 XXCNDMSBINMSHM-UHFFFAOYSA-N 0.000 claims 1
- KIYKWWQRXUTRAX-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2,3-dihydro-1h-inden-2-yl)morpholine-2-carboxamide Chemical compound C1C2=CC=CC=C2CC1NC(=O)C(C1)OCCN1S(=O)(=O)C1=C(C(=O)N)NC2=CC=C(Br)C=C21 KIYKWWQRXUTRAX-UHFFFAOYSA-N 0.000 claims 1
- LUYGRYORWWMEGW-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2,3-dihydro-1h-inden-2-ylmethyl)morpholine-2-carboxamide Chemical compound C1C2=CC=CC=C2CC1CNC(=O)C(C1)OCCN1S(=O)(=O)C1=C(C(=O)N)NC2=CC=C(Br)C=C21 LUYGRYORWWMEGW-UHFFFAOYSA-N 0.000 claims 1
- MEZZWFFSYZTZCL-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2-cyclohexylethyl)morpholine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCOC1C(=O)NCCC1CCCCC1 MEZZWFFSYZTZCL-UHFFFAOYSA-N 0.000 claims 1
- JKKMPNLSOMOXHT-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2-hydroxy-2,3-dihydro-1h-inden-1-yl)morpholine-2-carboxamide Chemical compound OC1CC2=CC=CC=C2C1NC(=O)C(C1)OCCN1S(=O)(=O)C1=C(C(=O)N)NC2=CC=C(Br)C=C21 JKKMPNLSOMOXHT-UHFFFAOYSA-N 0.000 claims 1
- AFJICAGJZCKIQI-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2-methoxyethyl)morpholine-2-carboxamide Chemical compound C1COC(C(=O)NCCOC)CN1S(=O)(=O)C1=C(C(N)=O)NC2=CC=C(Br)C=C12 AFJICAGJZCKIQI-UHFFFAOYSA-N 0.000 claims 1
- FYKJZHWCPYKVNH-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2-phenoxyethyl)morpholine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCOC1C(=O)NCCOC1=CC=CC=C1 FYKJZHWCPYKVNH-UHFFFAOYSA-N 0.000 claims 1
- PSABPMJAXRYHNY-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2-phenylethyl)morpholine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCOC1C(=O)NCCC1=CC=CC=C1 PSABPMJAXRYHNY-UHFFFAOYSA-N 0.000 claims 1
- DRHSSMHDIUWMQV-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2-phenylpropyl)morpholine-2-carboxamide Chemical compound C1N(S(=O)(=O)C=2C3=CC(Br)=CC=C3NC=2C(N)=O)CCOC1C(=O)NCC(C)C1=CC=CC=C1 DRHSSMHDIUWMQV-UHFFFAOYSA-N 0.000 claims 1
- OIHLRPAXOLPGTO-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2-tert-butylsulfanylethyl)morpholine-2-carboxamide Chemical compound C1COC(C(=O)NCCSC(C)(C)C)CN1S(=O)(=O)C1=C(C(N)=O)NC2=CC=C(Br)C=C12 OIHLRPAXOLPGTO-UHFFFAOYSA-N 0.000 claims 1
- PQGCABIODIKPGG-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(2-thiophen-2-ylethyl)morpholine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCOC1C(=O)NCCC1=CC=CS1 PQGCABIODIKPGG-UHFFFAOYSA-N 0.000 claims 1
- ZPZVLHPFKFKCKP-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(3,3-diphenylpropyl)morpholine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCOC1C(=O)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 ZPZVLHPFKFKCKP-UHFFFAOYSA-N 0.000 claims 1
- CWXWNCLWOHMQDB-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(3-butoxypropyl)morpholine-2-carboxamide Chemical compound C1COC(C(=O)NCCCOCCCC)CN1S(=O)(=O)C1=C(C(N)=O)NC2=CC=C(Br)C=C12 CWXWNCLWOHMQDB-UHFFFAOYSA-N 0.000 claims 1
- BQZCJIMIKBYSPZ-UHFFFAOYSA-N 4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]-n-(3-ethoxypropyl)morpholine-2-carboxamide Chemical compound C1COC(C(=O)NCCCOCC)CN1S(=O)(=O)C1=C(C(N)=O)NC2=CC=C(Br)C=C12 BQZCJIMIKBYSPZ-UHFFFAOYSA-N 0.000 claims 1
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- PYVOYTNMHYKHMU-UHFFFAOYSA-N n-benzyl-4-[(5-bromo-2-carbamoyl-1h-indol-3-yl)sulfonyl]morpholine-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Br)C=C2C=1S(=O)(=O)N(C1)CCOC1C(=O)NCC1=CC=CC=C1 PYVOYTNMHYKHMU-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 0 CC=C=Cc1c2c(S(**)(=O)=O)c(C(*)=O)[n]c2ccc1 Chemical compound CC=C=Cc1c2c(S(**)(=O)=O)c(C(*)=O)[n]c2ccc1 0.000 description 1
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| AU2003261415C1 (en) * | 2002-08-09 | 2010-01-14 | Merck Sharp & Dohme Corp. | Tyrosine kinase inhibitors |
| WO2004014300A2 (en) * | 2002-08-09 | 2004-02-19 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| SE0302811D0 (sv) * | 2003-10-23 | 2003-10-23 | Astrazeneca Ab | Novel compounds |
| JO2724B1 (en) | 2004-08-19 | 2013-09-15 | افينتس فارماسوتيكالز انك | 3-Alternative-5 -6-Amino Alkyl Indole-2-Carboxyl Acid Amide and Related Isotopes as Casein Kinase Inhibitors |
| US8957070B2 (en) | 2005-04-20 | 2015-02-17 | Takeda Pharmaceutical Company Limited | Glucokinase activator compounds, methods of activating glucokinase and methods of treating diabetes and obesity |
| AU2006262016A1 (en) * | 2005-06-28 | 2007-01-04 | Merck & Co., Inc. | Non-nucleoside reverse transcriptase inhibitors |
| AR055343A1 (es) * | 2005-06-30 | 2007-08-22 | Smithkline Beecham Corp | Derivados de indolcarboxamida inhibidores de quinasas ikk2 |
| US20090131494A1 (en) * | 2005-08-11 | 2009-05-21 | Williams Theresa M | Non-Nucleoside Reverse Transcriptase Inhibitors |
| EP2123644B1 (en) | 2007-03-07 | 2014-12-17 | Takeda Pharmaceutical Company Limited | Benzoxazepine derivatives and use thereof |
| US8642067B2 (en) | 2007-04-02 | 2014-02-04 | Allergen, Inc. | Methods and compositions for intraocular administration to treat ocular conditions |
| CA2758071C (en) | 2009-04-06 | 2018-01-09 | Agios Pharmaceuticals, Inc. | Pyruvate kinase m2 modulators, therapeutic compositions and related methods of use |
| WO2010138490A1 (en) * | 2009-05-26 | 2010-12-02 | Exelixis, Inc. | Benzoxazepines as inhibitors of mtor and methods of their use and manufacture |
| ES2618630T3 (es) * | 2009-06-29 | 2017-06-21 | Agios Pharmaceuticals, Inc. | Composiciones terapéuticas y métodos de uso relacionados |
| TWI598337B (zh) | 2009-06-29 | 2017-09-11 | 阿吉歐斯製藥公司 | 治療化合物及組成物 |
| WO2012083246A1 (en) | 2010-12-17 | 2012-06-21 | Agios Pharmaceuticals, Inc. | Novel n- (4- (azetidine - 1 - carbonyl) phenyl) - (hetero - ) arylsulfonamide derivatives as pyruvate kinase m2 (pmk2) modulators |
| ES2569712T3 (es) | 2010-12-21 | 2016-05-12 | Agios Pharmaceuticals, Inc. | Activadores de PKM2 bicíclicos |
| TWI549947B (zh) | 2010-12-29 | 2016-09-21 | 阿吉歐斯製藥公司 | 治療化合物及組成物 |
| AU2012245971A1 (en) * | 2011-04-21 | 2013-10-17 | Piramal Enterprises Limited | A crystalline form of a salt of a morpholino sulfonyl indole derivative and a process for its preparation |
| SMT202400081T1 (it) | 2011-05-03 | 2024-03-13 | Agios Pharmaceuticals Inc | Attivatori della piruvato chinasi per uso in terapia |
| US9181231B2 (en) | 2011-05-03 | 2015-11-10 | Agios Pharmaceuticals, Inc | Pyruvate kinase activators for use for increasing lifetime of the red blood cells and treating anemia |
| US8748446B2 (en) | 2012-03-03 | 2014-06-10 | Nanoquantum Sciences, Inc. | Halogenated compounds for photodynamic therapy |
| US20150119394A1 (en) * | 2012-03-28 | 2015-04-30 | Merck Sharp & Dohme Corp. | Insulin-Like Growth Factor-1 Receptor Inhibitors |
| DK2970265T3 (en) * | 2013-03-15 | 2018-10-01 | Plexxikon Inc | HETEROCYCLIC COMPOUNDS AND APPLICATIONS THEREOF |
| WO2014139144A1 (en) | 2013-03-15 | 2014-09-18 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
| US20140303121A1 (en) | 2013-03-15 | 2014-10-09 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| CA2989111C (en) | 2015-06-11 | 2023-10-03 | Agios Pharmaceuticals, Inc. | Methods of using pyruvate kinase activators |
| US10717735B2 (en) | 2017-10-13 | 2020-07-21 | Plexxikon Inc. | Solid forms of a compound for modulating kinases |
| US20250340532A1 (en) * | 2022-06-02 | 2025-11-06 | Xizang Haisco Pharmaceutical Co., Ltd. | Heterocyclic compound ccr4 inhibitor and user thereof |
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| US3209011A (en) * | 1963-10-07 | 1965-09-28 | Upjohn Co | 3-[(alkylcarbamoyl) sulfamoyl]-1-alkylindole-2-carboxylic acids and esters thereof |
| FR1410699A (fr) | 1963-10-07 | 1965-09-10 | Upjohn Co | Nouveaux indols |
| US3180875A (en) * | 1963-10-07 | 1965-04-27 | Upjohn Co | Derivatives of 3, 3'-dithiobis[indole-2-carboxylic acid] dihydrazides |
| BR8204028A (pt) | 1981-07-16 | 1983-07-05 | Du Pont | Composto herbicida composicao adequada e processo para controlar o crescimento de vegetacao indesejada |
| US5527819A (en) * | 1991-09-06 | 1996-06-18 | Merck & Co., Inc. | Inhibitors of HIV reverse transcriptase |
| CN1119856A (zh) * | 1993-02-24 | 1996-04-03 | 麦克公司 | Hiv逆转录酶抑制剂 |
| ATE243203T1 (de) | 1995-04-04 | 2003-07-15 | Texas Biotechnology Corp | Thienyl-, furyl-, pyrrolyl- und biphenylsulfonamide und derivate zur modulation der endothelin-aktivität |
| JP2002511852A (ja) * | 1997-05-07 | 2002-04-16 | スージェン・インコーポレーテッド | 蛋白質キナーゼ活性の調節剤としての２−インドリノン誘導体 |
| GB9902455D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| WO2003035621A1 (en) | 2001-10-22 | 2003-05-01 | The Research Foundation Of State University Of New York | Protein kinase and phosphatase inhibitors, methods for designing them, and methods of using them |
| WO2004014300A2 (en) | 2002-08-09 | 2004-02-19 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| AU2003261415C1 (en) * | 2002-08-09 | 2010-01-14 | Merck Sharp & Dohme Corp. | Tyrosine kinase inhibitors |
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2003
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- 2003-08-05 AT AT03784961T patent/ATE482938T1/de not_active IP Right Cessation
- 2003-08-05 CA CA2494962A patent/CA2494962C/en not_active Expired - Fee Related
- 2003-08-05 EP EP03784961A patent/EP1534695B1/en not_active Expired - Lifetime
- 2003-08-05 US US10/523,285 patent/US7560546B2/en not_active Expired - Lifetime
- 2003-08-05 DE DE60334386T patent/DE60334386D1/de not_active Expired - Lifetime
- 2003-08-05 WO PCT/US2003/024643 patent/WO2004014851A2/en not_active Ceased
- 2003-08-05 JP JP2004527799A patent/JP4332112B2/ja not_active Expired - Fee Related
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2009
- 2009-02-13 US US12/378,473 patent/US20090186871A1/en not_active Abandoned
- 2009-04-30 JP JP2009110392A patent/JP5261275B2/ja not_active Expired - Fee Related
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