ZA200405982B - Pyrrolopyrimidine and pyrrolopyridine derivatives substituted with cyclic amino group. - Google Patents
Pyrrolopyrimidine and pyrrolopyridine derivatives substituted with cyclic amino group. Download PDFInfo
- Publication number
- ZA200405982B ZA200405982B ZA200405982A ZA200405982A ZA200405982B ZA 200405982 B ZA200405982 B ZA 200405982B ZA 200405982 A ZA200405982 A ZA 200405982A ZA 200405982 A ZA200405982 A ZA 200405982A ZA 200405982 B ZA200405982 B ZA 200405982B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- pyrrolo
- dimethyl
- piperidin
- salkyl
- Prior art date
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- 125000003277 amino group Chemical group 0.000 title claims description 96
- 125000004122 cyclic group Chemical group 0.000 title claims description 96
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical group C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 title claims description 30
- KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical group C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 title claims description 11
- -1 saturated cyclic amine Chemical class 0.000 claims description 206
- 229910052739 hydrogen Inorganic materials 0.000 claims description 161
- 239000001257 hydrogen Substances 0.000 claims description 161
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 91
- 150000002431 hydrogen Chemical class 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 44
- 150000004677 hydrates Chemical class 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 42
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 40
- 150000002367 halogens Chemical class 0.000 claims description 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 125000004076 pyridyl group Chemical group 0.000 claims description 23
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 22
- 150000004944 pyrrolopyrimidines Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000005557 antagonist Substances 0.000 claims description 4
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 54
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 26
- 125000001246 bromo group Chemical group Br* 0.000 claims 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims 10
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 10
- 150000002148 esters Chemical class 0.000 claims 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 3
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 claims 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 2
- MGVNSMKDNCTMGY-UHFFFAOYSA-N 1-[1-(2,4-dibromophenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carbonitrile Chemical compound C12=NC(C)=CC(N3CCC(CC3)C#N)=C2C(C)=CN1C1=CC=C(Br)C=C1Br MGVNSMKDNCTMGY-UHFFFAOYSA-N 0.000 claims 1
- HDLXAJBKOSQRAS-UHFFFAOYSA-N 1-[1-(2,4-dichlorophenyl)-2,3,6-trimethylpyrrolo[2,3-b]pyridin-4-yl]piperidine-3-carbonitrile Chemical compound CC1=C(C)C2=C(N3CC(CCC3)C#N)C=C(C)N=C2N1C1=CC=C(Cl)C=C1Cl HDLXAJBKOSQRAS-UHFFFAOYSA-N 0.000 claims 1
- LTLJVEBSOOFJMA-UHFFFAOYSA-N 1-[1-(2,4-dichlorophenyl)-2,3,6-trimethylpyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carbonitrile Chemical compound CC1=C(C)C2=C(N3CCC(CC3)C#N)C=C(C)N=C2N1C1=CC=C(Cl)C=C1Cl LTLJVEBSOOFJMA-UHFFFAOYSA-N 0.000 claims 1
- LKZAEXTVJAYNMD-UHFFFAOYSA-N 1-[1-(2,6-dibromo-4-chlorophenyl)-2,3,6-trimethylpyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carbonitrile Chemical compound CC1=C(C)C2=C(N3CCC(CC3)C#N)C=C(C)N=C2N1C1=C(Br)C=C(Cl)C=C1Br LKZAEXTVJAYNMD-UHFFFAOYSA-N 0.000 claims 1
- MIXVUYODFGYIIS-UHFFFAOYSA-N 1-[1-(2,6-dibromo-4-propan-2-ylphenyl)-2,3,6-trimethylpyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carbonitrile Chemical compound BrC1=CC(C(C)C)=CC(Br)=C1N1C2=NC(C)=CC(N3CCC(CC3)C#N)=C2C(C)=C1C MIXVUYODFGYIIS-UHFFFAOYSA-N 0.000 claims 1
- CFIJLSZQATYTHY-UHFFFAOYSA-N 1-[1-(4-bromo-2,6-dimethylphenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidine-3-carbonitrile Chemical compound C12=NC(C)=CC(N3CC(CCC3)C#N)=C2C(C)=CN1C1=C(C)C=C(Br)C=C1C CFIJLSZQATYTHY-UHFFFAOYSA-N 0.000 claims 1
- AQLJEXFJKCOLFF-UHFFFAOYSA-N 1-[1-(4-chloro-2,6-dimethylphenyl)-2,3,6-trimethylpyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carbonitrile Chemical compound CC1=C(C)C2=C(N3CCC(CC3)C#N)C=C(C)N=C2N1C1=C(C)C=C(Cl)C=C1C AQLJEXFJKCOLFF-UHFFFAOYSA-N 0.000 claims 1
- XKEJIPYRXPSDSZ-UHFFFAOYSA-N 1-[1-(4-chloro-2,6-dimethylphenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carbonitrile Chemical compound C12=NC(C)=CC(N3CCC(CC3)C#N)=C2C(C)=CN1C1=C(C)C=C(Cl)C=C1C XKEJIPYRXPSDSZ-UHFFFAOYSA-N 0.000 claims 1
- HXBOZUOTSHPQGM-UHFFFAOYSA-N 1-[1-[1-(4-bromo-2,6-dimethylphenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]ethane-1,2-diol Chemical compound C12=NC(C)=CC(N3CCC(CC3)C(O)CO)=C2C(C)=CN1C1=C(C)C=C(Br)C=C1C HXBOZUOTSHPQGM-UHFFFAOYSA-N 0.000 claims 1
- GWWYMRBDNHGASK-UHFFFAOYSA-N 1-[1-[2-bromo-4-(trifluoromethyl)phenyl]-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carbonitrile Chemical compound C12=NC(C)=CC(N3CCC(CC3)C#N)=C2C(C)=CN1C1=CC=C(C(F)(F)F)C=C1Br GWWYMRBDNHGASK-UHFFFAOYSA-N 0.000 claims 1
- UBQCWWKXQTWSKR-UHFFFAOYSA-N 1-[1-[7-(4-bromo-2,6-dimethylphenyl)-2,5,6-trimethylpyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl]ethanol Chemical compound C1CC(C(O)C)CCN1C1=NC(C)=NC2=C1C(C)=C(C)N2C1=C(C)C=C(Br)C=C1C UBQCWWKXQTWSKR-UHFFFAOYSA-N 0.000 claims 1
- VRSVQZKQWJBBMK-UHFFFAOYSA-N 1-[1-[7-(4-chloro-2,6-dimethylphenyl)-2,5,6-trimethylpyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl]ethanol Chemical compound C1CC(C(O)C)CCN1C1=NC(C)=NC2=C1C(C)=C(C)N2C1=C(C)C=C(Cl)C=C1C VRSVQZKQWJBBMK-UHFFFAOYSA-N 0.000 claims 1
- ASDIAGHLEYKJHH-UHFFFAOYSA-N 1-[2,3,6-trimethyl-1-(2,4,5-tribromophenyl)pyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carbonitrile Chemical compound CC1=C(C)C2=C(N3CCC(CC3)C#N)C=C(C)N=C2N1C1=CC(Br)=C(Br)C=C1Br ASDIAGHLEYKJHH-UHFFFAOYSA-N 0.000 claims 1
- QDSSCAURYMAEFJ-UHFFFAOYSA-N 1-[2,3,6-trimethyl-1-(2,4,6-tribromophenyl)pyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carbonitrile Chemical compound CC1=C(C)C2=C(N3CCC(CC3)C#N)C=C(C)N=C2N1C1=C(Br)C=C(Br)C=C1Br QDSSCAURYMAEFJ-UHFFFAOYSA-N 0.000 claims 1
- DLUUYIAQWRKXHP-UHFFFAOYSA-N 1-[3,6-dimethyl-1-(2,4,5-tribromophenyl)pyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carbonitrile Chemical compound C12=NC(C)=CC(N3CCC(CC3)C#N)=C2C(C)=CN1C1=CC(Br)=C(Br)C=C1Br DLUUYIAQWRKXHP-UHFFFAOYSA-N 0.000 claims 1
- BVPGDIGXFRHSOC-UHFFFAOYSA-N 1-[3,6-dimethyl-1-(2,4,6-tribromophenyl)pyrrolo[2,3-b]pyridin-4-yl]piperidine-4-carbonitrile Chemical compound C12=NC(C)=CC(N3CCC(CC3)C#N)=C2C(C)=CN1C1=C(Br)C=C(Br)C=C1Br BVPGDIGXFRHSOC-UHFFFAOYSA-N 0.000 claims 1
- HKHJQXCPYCGKAD-UHFFFAOYSA-N 1-[7-(4-bromo-2,6-diethylphenyl)-2,5-dimethylpyrrolo[2,3-d]pyrimidin-4-yl]piperidine-3-carbonitrile Chemical compound CCC1=CC(Br)=CC(CC)=C1N1C2=NC(C)=NC(N3CC(CCC3)C#N)=C2C(C)=C1 HKHJQXCPYCGKAD-UHFFFAOYSA-N 0.000 claims 1
- QTEKZKBLFLXAON-UHFFFAOYSA-N 1-[7-(4-bromo-2,6-dimethylphenyl)-2,5,6-trimethylpyrrolo[2,3-d]pyrimidin-4-yl]piperidine-3-carbonitrile Chemical compound CC1=C(C)C2=C(N3CC(CCC3)C#N)N=C(C)N=C2N1C1=C(C)C=C(Br)C=C1C QTEKZKBLFLXAON-UHFFFAOYSA-N 0.000 claims 1
- VMLFTDFVFBRLTL-UHFFFAOYSA-N 1-[7-(4-bromo-2,6-dimethylphenyl)-2,5,6-trimethylpyrrolo[2,3-d]pyrimidin-4-yl]pyrrolidine-3-carbonitrile Chemical compound CC1=C(C)C2=C(N3CC(CC3)C#N)N=C(C)N=C2N1C1=C(C)C=C(Br)C=C1C VMLFTDFVFBRLTL-UHFFFAOYSA-N 0.000 claims 1
- IBFBWKGXWGVBJA-UHFFFAOYSA-N 1-[7-(4-bromo-2,6-dimethylphenyl)-2,5-dimethylpyrrolo[2,3-d]pyrimidin-4-yl]azepane-4-carbonitrile Chemical compound C12=NC(C)=NC(N3CCC(CCC3)C#N)=C2C(C)=CN1C1=C(C)C=C(Br)C=C1C IBFBWKGXWGVBJA-UHFFFAOYSA-N 0.000 claims 1
- TWAJCMRSSAYRLO-UHFFFAOYSA-N 1-[7-(4-bromo-2,6-dimethylphenyl)-2,5-dimethylpyrrolo[2,3-d]pyrimidin-4-yl]piperidine-4-carbonitrile Chemical compound C12=NC(C)=NC(N3CCC(CC3)C#N)=C2C(C)=CN1C1=C(C)C=C(Br)C=C1C TWAJCMRSSAYRLO-UHFFFAOYSA-N 0.000 claims 1
- XKUVKDVHDROZBE-UHFFFAOYSA-N 1-[7-[2,6-dibromo-4-(trifluoromethyl)phenyl]-2,5,6-trimethylpyrrolo[2,3-d]pyrimidin-4-yl]piperidine-3-carbonitrile Chemical compound CC1=C(C)C2=C(N3CC(CCC3)C#N)N=C(C)N=C2N1C1=C(Br)C=C(C(F)(F)F)C=C1Br XKUVKDVHDROZBE-UHFFFAOYSA-N 0.000 claims 1
- WYAMKPADTZURPG-UHFFFAOYSA-N 2-[1-[1-(2,4-dibromophenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]acetonitrile Chemical compound C12=NC(C)=CC(N3CCC(CC#N)CC3)=C2C(C)=CN1C1=CC=C(Br)C=C1Br WYAMKPADTZURPG-UHFFFAOYSA-N 0.000 claims 1
- ZMBRIOFYOCHDHE-UHFFFAOYSA-N 2-[1-[1-(2,4-dichlorophenyl)-2,3,6-trimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-3-yl]ethanol Chemical compound CC1=C(C)C2=C(N3CC(CCO)CCC3)C=C(C)N=C2N1C1=CC=C(Cl)C=C1Cl ZMBRIOFYOCHDHE-UHFFFAOYSA-N 0.000 claims 1
- QXNYABHUACQZBI-UHFFFAOYSA-N 2-[1-[1-(2,4-dichlorophenyl)-2,3,6-trimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]acetonitrile Chemical compound CC1=C(C)C2=C(N3CCC(CC#N)CC3)C=C(C)N=C2N1C1=CC=C(Cl)C=C1Cl QXNYABHUACQZBI-UHFFFAOYSA-N 0.000 claims 1
- SCFCLXHRLULCGM-UHFFFAOYSA-N 2-[1-[1-(2,6-dibromo-4-chlorophenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]ethanol Chemical compound C12=NC(C)=CC(N3CCC(CCO)CC3)=C2C(C)=CN1C1=C(Br)C=C(Cl)C=C1Br SCFCLXHRLULCGM-UHFFFAOYSA-N 0.000 claims 1
- QYFGOSXQSPHJLD-UHFFFAOYSA-N 2-[1-[1-(2,6-dibromo-4-propan-2-ylphenyl)-2,3,6-trimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]acetonitrile Chemical compound BrC1=CC(C(C)C)=CC(Br)=C1N1C2=NC(C)=CC(N3CCC(CC#N)CC3)=C2C(C)=C1C QYFGOSXQSPHJLD-UHFFFAOYSA-N 0.000 claims 1
- HSIPWAIJVKVXIB-UHFFFAOYSA-N 2-[1-[1-(2,6-dibromo-4-propan-2-ylphenyl)-2,3,6-trimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]ethanol Chemical compound BrC1=CC(C(C)C)=CC(Br)=C1N1C2=NC(C)=CC(N3CCC(CCO)CC3)=C2C(C)=C1C HSIPWAIJVKVXIB-UHFFFAOYSA-N 0.000 claims 1
- SDZNYWPOJYYOBN-UHFFFAOYSA-N 2-[1-[1-(2,6-dibromo-4-propan-2-ylphenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]acetonitrile Chemical compound BrC1=CC(C(C)C)=CC(Br)=C1N1C2=NC(C)=CC(N3CCC(CC#N)CC3)=C2C(C)=C1 SDZNYWPOJYYOBN-UHFFFAOYSA-N 0.000 claims 1
- ZORBZVDVNRTURS-UHFFFAOYSA-N 2-[1-[1-(2,6-dibromo-4-propan-2-ylphenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]ethanol Chemical compound BrC1=CC(C(C)C)=CC(Br)=C1N1C2=NC(C)=CC(N3CCC(CCO)CC3)=C2C(C)=C1 ZORBZVDVNRTURS-UHFFFAOYSA-N 0.000 claims 1
- YFWVVTZMAJWQCF-UHFFFAOYSA-N 2-[1-[1-(2-bromo-4-propan-2-ylphenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]ethanol Chemical compound BrC1=CC(C(C)C)=CC=C1N1C2=NC(C)=CC(N3CCC(CCO)CC3)=C2C(C)=C1 YFWVVTZMAJWQCF-UHFFFAOYSA-N 0.000 claims 1
- GBMWKBFGKAFXAO-UHFFFAOYSA-N 2-[1-[1-(4-bromo-2,6-dichlorophenyl)-2,3,6-trimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]ethanol Chemical compound CC1=C(C)C2=C(N3CCC(CCO)CC3)C=C(C)N=C2N1C1=C(Cl)C=C(Br)C=C1Cl GBMWKBFGKAFXAO-UHFFFAOYSA-N 0.000 claims 1
- RMDXFCFGULPTPV-UHFFFAOYSA-N 2-[1-[1-(4-bromo-2,6-dichlorophenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]acetonitrile Chemical compound C12=NC(C)=CC(N3CCC(CC#N)CC3)=C2C(C)=CN1C1=C(Cl)C=C(Br)C=C1Cl RMDXFCFGULPTPV-UHFFFAOYSA-N 0.000 claims 1
- KTBHZFJQSJNLKJ-UHFFFAOYSA-N 2-[1-[1-(4-bromo-2,6-dichlorophenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]ethanol Chemical compound C12=NC(C)=CC(N3CCC(CCO)CC3)=C2C(C)=CN1C1=C(Cl)C=C(Br)C=C1Cl KTBHZFJQSJNLKJ-UHFFFAOYSA-N 0.000 claims 1
- JCAYVXVGQSUSOX-UHFFFAOYSA-N 2-[1-[1-(4-bromo-2,6-dimethylphenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]acetonitrile Chemical compound C12=NC(C)=CC(N3CCC(CC#N)CC3)=C2C(C)=CN1C1=C(C)C=C(Br)C=C1C JCAYVXVGQSUSOX-UHFFFAOYSA-N 0.000 claims 1
- XBCWTGJYPAZRSC-UHFFFAOYSA-N 2-[1-[1-(4-bromo-2,6-dimethylphenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]ethanol Chemical compound C12=NC(C)=CC(N3CCC(CCO)CC3)=C2C(C)=CN1C1=C(C)C=C(Br)C=C1C XBCWTGJYPAZRSC-UHFFFAOYSA-N 0.000 claims 1
- ATUNWBVIJXIRQT-UHFFFAOYSA-N 2-[1-[1-(4-methoxy-2,6-dimethylphenyl)-2,3,6-trimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]acetonitrile Chemical compound CC1=CC(OC)=CC(C)=C1N1C2=NC(C)=CC(N3CCC(CC#N)CC3)=C2C(C)=C1C ATUNWBVIJXIRQT-UHFFFAOYSA-N 0.000 claims 1
- DLTSRPJDTXDDNX-UHFFFAOYSA-N 2-[1-[1-(4-methoxy-2,6-dimethylphenyl)-3,6-dimethylpyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]acetonitrile Chemical compound CC1=CC(OC)=CC(C)=C1N1C2=NC(C)=CC(N3CCC(CC#N)CC3)=C2C(C)=C1 DLTSRPJDTXDDNX-UHFFFAOYSA-N 0.000 claims 1
- USNPZJXBJGHNMP-UHFFFAOYSA-N 2-[1-[2,3,6-trimethyl-1-(2,4,6-tribromophenyl)pyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]ethanol Chemical compound CC1=C(C)C2=C(N3CCC(CCO)CC3)C=C(C)N=C2N1C1=C(Br)C=C(Br)C=C1Br USNPZJXBJGHNMP-UHFFFAOYSA-N 0.000 claims 1
- DDDIQFPNSQUDMN-UHFFFAOYSA-N 2-[1-[2,3,6-trimethyl-1-(2,4,6-trichlorophenyl)pyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]acetonitrile Chemical compound CC1=C(C)C2=C(N3CCC(CC#N)CC3)C=C(C)N=C2N1C1=C(Cl)C=C(Cl)C=C1Cl DDDIQFPNSQUDMN-UHFFFAOYSA-N 0.000 claims 1
- IRLMOEJUDHQVJP-UHFFFAOYSA-N 2-[1-[2,3,6-trimethyl-1-(2,4,6-trichlorophenyl)pyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl]ethanol Chemical compound CC1=C(C)C2=C(N3CCC(CCO)CC3)C=C(C)N=C2N1C1=C(Cl)C=C(Cl)C=C1Cl IRLMOEJUDHQVJP-UHFFFAOYSA-N 0.000 claims 1
- VLRSDFNGLBXMNU-UHFFFAOYSA-N 2-[1-[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl]acetonitrile Chemical compound CC1=C(C)C2=C(N3CCC(CC#N)CC3)N=C(C)N=C2N1C1=C(C)C=C(C)C=C1C VLRSDFNGLBXMNU-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Neurosurgery (AREA)
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- Biomedical Technology (AREA)
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- Vascular Medicine (AREA)
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- Nitrogen Condensed Heterocyclic Rings (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002383667 | 2002-12-26 |
Publications (1)
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| ZA200405982B true ZA200405982B (en) | 2005-09-02 |
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| ZA200405982A ZA200405982B (en) | 2002-12-26 | 2004-07-27 | Pyrrolopyrimidine and pyrrolopyridine derivatives substituted with cyclic amino group. |
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| US (3) | US20050209253A1 (ko) |
| EP (2) | EP1787992B1 (ko) |
| JP (1) | JP4181126B2 (ko) |
| KR (2) | KR100688395B1 (ko) |
| CN (1) | CN1692115A (ko) |
| AR (1) | AR042667A1 (ko) |
| AT (2) | ATE430151T1 (ko) |
| AU (1) | AU2003292550B8 (ko) |
| BR (1) | BR0307587A (ko) |
| CA (1) | CA2485556C (ko) |
| CL (1) | CL2003002762A1 (ko) |
| DE (2) | DE60319951T2 (ko) |
| EA (1) | EA200401060A1 (ko) |
| ES (2) | ES2325596T3 (ko) |
| HR (1) | HRP20040724A2 (ko) |
| MX (1) | MXPA04008081A (ko) |
| MY (1) | MY141200A (ko) |
| NO (1) | NO20043508L (ko) |
| PL (1) | PL371810A1 (ko) |
| TW (1) | TWI270549B (ko) |
| UA (1) | UA77265C2 (ko) |
| WO (1) | WO2004058767A1 (ko) |
| ZA (1) | ZA200405982B (ko) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE602005000676T2 (de) | 2004-01-06 | 2007-11-22 | Taisho Pharmaceutical Co., Ltd. | Triazacyclopenta[cd]indenderivate |
| US7557111B2 (en) * | 2004-01-06 | 2009-07-07 | Taisho Pharmaceutical Co., Ltd. | Substituted thieno[3,2-d]pyrimidines as CRF receptor antagonists |
| JP4742273B2 (ja) | 2004-01-06 | 2011-08-10 | 大正製薬株式会社 | ピロロピリミジン及びピロロトリアジン誘導体 |
| JP2007526906A (ja) * | 2004-03-05 | 2007-09-20 | 大正製薬株式会社 | ピロロピリミジン誘導体 |
| BRPI0512514A (pt) * | 2004-06-25 | 2008-03-11 | Taisho Pharmaceutical Co Ltd | composto, antagonista para receptores de crf, e, uso de um composto |
| JP2007161585A (ja) * | 2004-06-25 | 2007-06-28 | Taisho Pharmaceut Co Ltd | 環状アミノ基で置換されているピロロピリミジン及びピロロピリジン誘導体 |
| DE102004042607A1 (de) * | 2004-09-03 | 2006-03-09 | Bayer Healthcare Ag | Substituierte Phenylaminothiazole und ihre Verwendung |
| DE102006042143A1 (de) * | 2006-09-08 | 2008-03-27 | Bayer Healthcare Aktiengesellschaft | Neue substituierte Bipyridin-Derivate und ihre Verwendung |
| DE102006056739A1 (de) * | 2006-12-01 | 2008-06-05 | Bayer Healthcare Ag | Substituierte 4-Amino-3,5-dicyano-2-thiopyridine und ihre Verwendung |
| DE102006056740A1 (de) * | 2006-12-01 | 2008-06-05 | Bayer Healthcare Ag | Cyclisch substituierte 3,5-Dicyano-2-thiopyridine und ihre Verwendung |
| EA020466B1 (ru) | 2007-06-04 | 2014-11-28 | Синерджи Фармасьютикалз Инк. | Агонисты гуанилатциклазы, пригодные для лечения желудочно-кишечных нарушений, воспаления, рака и других заболеваний |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| DE102007035367A1 (de) | 2007-07-27 | 2009-01-29 | Bayer Healthcare Ag | Substituierte Aryloxazole und ihre Verwendung |
| DE102007036076A1 (de) | 2007-08-01 | 2009-02-05 | Bayer Healthcare Aktiengesellschaft | Dipeptoid-Produgs und ihre Verwendung |
| DE102007061764A1 (de) * | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Anellierte Cyanopyridine und ihre Verwendung |
| DE102007061763A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Substituierte azabicyclische Verbindungen und ihre Verwendung |
| DE102008013587A1 (de) * | 2008-03-11 | 2009-09-17 | Bayer Schering Pharma Aktiengesellschaft | Heteroaryl-substituierte Dicyanopyridine und ihre Verwendung |
| CL2009001152A1 (es) | 2008-05-13 | 2009-10-16 | Array Biopharma Inc | Compuestos derivados de n-(4-(cicloalquilo nitrogenado-1-il)-1h-pirrolo[2,3-b]piridin-3-il)amida, inhibidores de cinasa; proceso de preparacion; composicion farmaceutica; y su uso para el tratamiento de una enfermedad proliferativa. |
| EP2297104B1 (de) * | 2008-05-29 | 2013-08-07 | Bayer Intellectual Property GmbH | 2-alkoxy-substituierte dicyanopyridine und ihre verwendung |
| CA2726917C (en) | 2008-06-04 | 2018-06-26 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| CA2730603C (en) | 2008-07-16 | 2019-09-24 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| DE102008062567A1 (de) | 2008-12-16 | 2010-06-17 | Bayer Schering Pharma Aktiengesellschaft | Dipeptoid-Prodrugs und ihre Verwendung |
| DE102009006602A1 (de) * | 2009-01-29 | 2010-08-05 | Bayer Schering Pharma Aktiengesellschaft | Alkylamino-substituierte Dicyanopyridine und deren Aminosäureester-Prodrugs |
| DE102010030688A1 (de) | 2010-06-30 | 2012-01-05 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Dicyanopyridine und ihre Verwendung |
| US20120058983A1 (en) | 2010-09-02 | 2012-03-08 | Bayer Pharma Aktiengesellschaft | Adenosine A1 agonists for the treatment of glaucoma and ocular hypertension |
| KR20140059164A (ko) | 2011-03-15 | 2014-05-15 | 트라이우스 테라퓨틱스, 아이엔씨. | 트라이사이클릭 자이라제 억제제 |
| EP2970384A1 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| CA2905435A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| BR112015019412A8 (pt) | 2013-04-11 | 2019-11-12 | Hoffmann La Roche | inibidores de bace1, seus usos, e composição farmacêutica |
| SG11201509029PA (en) * | 2013-05-02 | 2015-12-30 | Hoffmann La Roche | Pyrrolo[2,3-d]pyrimidine derivatives as cb2 receptor agonists |
| CN114829362A (zh) * | 2019-12-10 | 2022-07-29 | 成都倍特药业股份有限公司 | 一种可用作shp2抑制剂的含氮杂原子的六元并五元芳环衍生物 |
| CN114646700B (zh) * | 2022-03-01 | 2023-10-20 | 浙江国邦药业有限公司 | 一种（s）-吡咯烷-2-甲腈盐酸盐的检测方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6765008B1 (en) | 1992-12-17 | 2004-07-20 | Pfizer Inc | Pyrrolopyrimidines as CRF antagonists |
| US5646152A (en) | 1994-06-15 | 1997-07-08 | Pfizer Inc. | Methods of administering CRF antagonists |
| PL181895B1 (pl) | 1994-06-16 | 2001-10-31 | Pfizer | Nowe pirazolo-i pirolopirydyny _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ PL PL PL PL |
| ES2203937T3 (es) * | 1997-03-26 | 2004-04-16 | Taisho Pharmaceutical Co., Ltd | Derivados de 4-tetrahidropiridilpirimidina. |
| AU756702B2 (en) * | 1999-03-11 | 2003-01-23 | Taisho Pharmaceutical Co., Ltd. | Carbamoyl tetrahydropyridine derivatives |
| AR028782A1 (es) * | 2000-07-05 | 2003-05-21 | Taisho Pharmaceutical Co Ltd | Derivados heterociclicos tetrahidropiridino o piperidino |
| DE602005000676T2 (de) * | 2004-01-06 | 2007-11-22 | Taisho Pharmaceutical Co., Ltd. | Triazacyclopenta[cd]indenderivate |
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2003
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- 2003-12-24 PL PL03371810A patent/PL371810A1/xx not_active Application Discontinuation
- 2003-12-24 ES ES06019987T patent/ES2325596T3/es not_active Expired - Lifetime
- 2003-12-24 KR KR1020047013348A patent/KR100688395B1/ko not_active IP Right Cessation
- 2003-12-24 JP JP2004562918A patent/JP4181126B2/ja not_active Expired - Fee Related
- 2003-12-24 AT AT06019987T patent/ATE430151T1/de not_active IP Right Cessation
- 2003-12-24 CA CA002485556A patent/CA2485556C/en not_active Expired - Fee Related
- 2003-12-24 US US10/504,981 patent/US20050209253A1/en not_active Abandoned
- 2003-12-24 MY MYPI20034990A patent/MY141200A/en unknown
- 2003-12-24 CN CNA2003801004264A patent/CN1692115A/zh active Pending
- 2003-12-24 UA UA20040907464A patent/UA77265C2/uk unknown
- 2003-12-24 BR BR0307587-7A patent/BR0307587A/pt not_active IP Right Cessation
- 2003-12-24 AU AU2003292550A patent/AU2003292550B8/en not_active Ceased
- 2003-12-24 DE DE60319951T patent/DE60319951T2/de not_active Expired - Lifetime
- 2003-12-24 EA EA200401060A patent/EA200401060A1/ru unknown
- 2003-12-24 KR KR1020067025000A patent/KR100808756B1/ko not_active IP Right Cessation
- 2003-12-24 MX MXPA04008081A patent/MXPA04008081A/es active IP Right Grant
- 2003-12-24 EP EP03768186A patent/EP1467997B8/en not_active Expired - Lifetime
- 2003-12-24 ES ES03768186T patent/ES2302949T3/es not_active Expired - Lifetime
- 2003-12-24 AT AT03768186T patent/ATE390426T1/de not_active IP Right Cessation
- 2003-12-24 DE DE60327477T patent/DE60327477D1/de not_active Expired - Lifetime
- 2003-12-26 CL CL200302762A patent/CL2003002762A1/es unknown
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2004
- 2004-07-27 ZA ZA200405982A patent/ZA200405982B/en unknown
- 2004-08-10 HR HR20040724A patent/HRP20040724A2/hr not_active Application Discontinuation
- 2004-08-23 NO NO20043508A patent/NO20043508L/no not_active Application Discontinuation
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2008
- 2008-04-21 US US12/106,873 patent/US7932259B2/en not_active Expired - Fee Related
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- 2010-11-22 US US12/951,556 patent/US8455511B2/en not_active Expired - Fee Related
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