SK4642002A3 - Bicyclic imidazo-5-yl-amine derivatives method for producing thereof, use thereof and pharmaceutical compositions containing said compounds - Google Patents
Bicyclic imidazo-5-yl-amine derivatives method for producing thereof, use thereof and pharmaceutical compositions containing said compounds Download PDFInfo
- Publication number
- SK4642002A3 SK4642002A3 SK464-2002A SK4642002A SK4642002A3 SK 4642002 A3 SK4642002 A3 SK 4642002A3 SK 4642002 A SK4642002 A SK 4642002A SK 4642002 A3 SK4642002 A3 SK 4642002A3
- Authority
- SK
- Slovakia
- Prior art keywords
- imidazo
- phenyl
- amine
- tert
- butyl
- Prior art date
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- 125000002619 bicyclic group Chemical group 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 543
- -1 4-morpholino, 1,1,3,3-tetramethylbutyl Chemical group 0.000 claims description 240
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 112
- 230000015572 biosynthetic process Effects 0.000 claims description 63
- 238000003786 synthesis reaction Methods 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 8
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- QVMNFBZORCNYHQ-UHFFFAOYSA-N n-[4-[6-(cyclohexylamino)-1h-imidazo[1,2-b][1,2,4]triazol-5-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=C(NC2CCCCC2)N2NC=NC2=N1 QVMNFBZORCNYHQ-UHFFFAOYSA-N 0.000 claims description 7
- UDXYXCDIVWOLNF-UHFFFAOYSA-N n-butyl-n-[5-(2-chloro-6-fluorophenyl)-1h-imidazo[1,2-b][1,2,4]triazol-6-yl]acetamide Chemical compound N1=C2N=CNN2C(N(C(C)=O)CCCC)=C1C1=C(F)C=CC=C1Cl UDXYXCDIVWOLNF-UHFFFAOYSA-N 0.000 claims description 7
- PKDNZDBWFVXULD-UHFFFAOYSA-N n-butyl-n-[6-(4-tert-butylphenyl)-2-methylimidazo[2,1-b][1,3]thiazol-5-yl]acetamide Chemical compound N1=C2SC(C)=CN2C(N(C(C)=O)CCCC)=C1C1=CC=C(C(C)(C)C)C=C1 PKDNZDBWFVXULD-UHFFFAOYSA-N 0.000 claims description 7
- ZVILOTMIJWAEMA-UHFFFAOYSA-N n-cyclohexyl-6-(2,5-dimethylphenyl)imidazo[2,1-b][1,3]thiazol-5-amine Chemical compound CC1=CC=C(C)C(C2=C(N3C=CSC3=N2)NC2CCCCC2)=C1 ZVILOTMIJWAEMA-UHFFFAOYSA-N 0.000 claims description 7
- DWYNLJQDBCJIRE-UHFFFAOYSA-N n-cyclohexyl-6-pyridin-2-ylimidazo[2,1-b][1,3]thiazol-5-amine Chemical compound C1CCCCC1NC1=C(C=2N=CC=CC=2)N=C2N1C=CS2 DWYNLJQDBCJIRE-UHFFFAOYSA-N 0.000 claims description 7
- XBFSPBUEYSJBMN-UHFFFAOYSA-N n-tert-butyl-n-[6-(2-methylphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]acetamide Chemical compound N1=C2SC=CN2C(N(C(=O)C)C(C)(C)C)=C1C1=CC=CC=C1C XBFSPBUEYSJBMN-UHFFFAOYSA-N 0.000 claims description 7
- BNPBSQNAZYSWGG-UHFFFAOYSA-N n-tert-butyl-n-[6-(4-methylphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]acetamide Chemical compound N1=C2SC=CN2C(N(C(=O)C)C(C)(C)C)=C1C1=CC=C(C)C=C1 BNPBSQNAZYSWGG-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- RGSQRYHTBPGBNU-UHFFFAOYSA-N 2-[6-cyclohexyl-5-(cyclohexylamino)imidazo[2,1-b][1,3]thiazol-3-yl]acetic acid Chemical compound C1CCCCC1NC=1N2C(CC(=O)O)=CSC2=NC=1C1CCCCC1 RGSQRYHTBPGBNU-UHFFFAOYSA-N 0.000 claims description 6
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
- SKSVTGFHNSNQBZ-UHFFFAOYSA-N 3-[5-(tert-butylamino)imidazo[2,1-b][1,3]thiazol-6-yl]phenol Chemical compound N1=C2SC=CN2C(NC(C)(C)C)=C1C1=CC=CC(O)=C1 SKSVTGFHNSNQBZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 6
- TYQLVLQKPSSXOW-UHFFFAOYSA-N n-cyclohexyl-6-(2,4-dimethylphenyl)imidazo[2,1-b][1,3]thiazol-5-amine Chemical compound CC1=CC(C)=CC=C1C1=C(NC2CCCCC2)N2C=CSC2=N1 TYQLVLQKPSSXOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 6
- LNNOABBVCVKLMY-UHFFFAOYSA-N 2-[5-(cyclohexylamino)-6-methylimidazo[2,1-b][1,3]thiazol-3-yl]acetic acid Chemical compound CC=1N=C2SC=C(CC(O)=O)N2C=1NC1CCCCC1 LNNOABBVCVKLMY-UHFFFAOYSA-N 0.000 claims description 5
- KEHFIZQNMNMELE-UHFFFAOYSA-N 2-[5-(tert-butylamino)-6-(furan-2-yl)imidazo[2,1-b][1,3]thiazol-3-yl]acetic acid Chemical compound N1=C2SC=C(CC(O)=O)N2C(NC(C)(C)C)=C1C1=CC=CO1 KEHFIZQNMNMELE-UHFFFAOYSA-N 0.000 claims description 5
- RXEGTWSFOIRZJH-UHFFFAOYSA-N 5-(2,5-dimethylphenyl)-n-(2,4,4-trimethylpentan-2-yl)-1h-imidazo[1,2-b][1,2,4]triazol-6-amine Chemical compound CC1=CC=C(C)C(C2=C(N3NC=NC3=N2)NC(C)(C)CC(C)(C)C)=C1 RXEGTWSFOIRZJH-UHFFFAOYSA-N 0.000 claims description 5
- VUNKPGIOBGHERL-UHFFFAOYSA-N n,6-dicyclohexylimidazo[2,1-b][1,3]thiazol-5-amine Chemical compound C1CCCCC1NC1=C(C2CCCCC2)N=C2N1C=CS2 VUNKPGIOBGHERL-UHFFFAOYSA-N 0.000 claims description 5
- UHJKVIKRLZEECP-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-6-pyridin-3-ylimidazo[2,1-b][1,3]thiazol-5-amine Chemical compound CC1=CC=CC(C)=C1NC1=C(C=2C=NC=CC=2)N=C2N1C=CS2 UHJKVIKRLZEECP-UHFFFAOYSA-N 0.000 claims description 5
- BNAPFJXCQUISEE-UHFFFAOYSA-N n-cyclohexyl-6-pyridin-4-ylimidazo[2,1-b][1,3]thiazol-5-amine Chemical compound C1CCCCC1NC1=C(C=2C=CN=CC=2)N=C2N1C=CS2 BNAPFJXCQUISEE-UHFFFAOYSA-N 0.000 claims description 5
- IWRXIBUAPAAHJE-UHFFFAOYSA-N n-tert-butyl-6-(2-methylphenyl)imidazo[2,1-b][1,3]thiazol-5-amine Chemical compound CC1=CC=CC=C1C1=C(NC(C)(C)C)N2C=CSC2=N1 IWRXIBUAPAAHJE-UHFFFAOYSA-N 0.000 claims description 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000001409 amidines Chemical class 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- 150000002527 isonitriles Chemical class 0.000 claims description 4
- YELSMCBMWVEJQK-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-5-(furan-2-yl)-1h-imidazo[1,2-b][1,2,4]triazol-6-amine Chemical compound CC1=CC=CC(C)=C1NC1=C(C=2OC=CC=2)N=C2N1NC=N2 YELSMCBMWVEJQK-UHFFFAOYSA-N 0.000 claims description 4
- ZRGYZZRVSFRLQD-UHFFFAOYSA-N n-tert-butyl-6-(4-methylphenyl)imidazo[2,1-b][1,3]thiazol-5-amine Chemical compound C1=CC(C)=CC=C1C1=C(NC(C)(C)C)N2C=CSC2=N1 ZRGYZZRVSFRLQD-UHFFFAOYSA-N 0.000 claims description 4
- HPZMQBYGFLVSBR-UHFFFAOYSA-N n-tert-butyl-6-(furan-2-yl)imidazo[2,1-b][1,3]thiazol-5-amine Chemical compound N1=C2SC=CN2C(NC(C)(C)C)=C1C1=CC=CO1 HPZMQBYGFLVSBR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
- RRZPHZNDSFKENS-UHFFFAOYSA-N n-tert-butyl-5-(2-methoxyphenyl)-1h-imidazo[1,2-b][1,2,4]triazol-6-amine Chemical compound COC1=CC=CC=C1C1=C(NC(C)(C)C)N2NC=NC2=N1 RRZPHZNDSFKENS-UHFFFAOYSA-N 0.000 claims description 3
- YFSNIIOBVMRDCA-UHFFFAOYSA-N n-tert-butyl-6-(2,3-dimethoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-amine Chemical compound COC1=CC=CC(C2=C(N3C=CSC3=N2)NC(C)(C)C)=C1OC YFSNIIOBVMRDCA-UHFFFAOYSA-N 0.000 claims description 3
- OPKDVXKVRODVTB-UHFFFAOYSA-N n-tert-butyl-6-(2-fluorophenyl)imidazo[2,1-b][1,3]thiazol-5-amine Chemical compound N1=C2SC=CN2C(NC(C)(C)C)=C1C1=CC=CC=C1F OPKDVXKVRODVTB-UHFFFAOYSA-N 0.000 claims description 3
- CDAVLFVNHWLDPV-UHFFFAOYSA-N n-tert-butyl-6-(3,4-dimethoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(NC(C)(C)C)N2C=CSC2=N1 CDAVLFVNHWLDPV-UHFFFAOYSA-N 0.000 claims description 3
- YSEOTLWBULXAAG-UHFFFAOYSA-N n-tert-butyl-6-methylimidazo[2,1-b][1,3]thiazol-5-amine Chemical compound S1C=CN2C(NC(C)(C)C)=C(C)N=C21 YSEOTLWBULXAAG-UHFFFAOYSA-N 0.000 claims description 3
- VBEGQGISJGICBS-UHFFFAOYSA-N n-tert-butyl-6-pyridin-2-ylimidazo[2,1-b][1,3]thiazol-5-amine Chemical compound N1=C2SC=CN2C(NC(C)(C)C)=C1C1=CC=CC=N1 VBEGQGISJGICBS-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 150000003233 pyrroles Chemical class 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- IEWRGYRCGQVEMJ-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)pyrrole Chemical compound ClC1=CC(Cl)=CC(N2C=CC=C2)=C1 IEWRGYRCGQVEMJ-UHFFFAOYSA-N 0.000 claims description 2
- LTOQUFIOYDCJFJ-UHFFFAOYSA-N 1-(4-chlorophenyl)pyrrole Chemical compound C1=CC(Cl)=CC=C1N1C=CC=C1 LTOQUFIOYDCJFJ-UHFFFAOYSA-N 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 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 description 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 2
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- NNXDJLDBAFGYGK-UHFFFAOYSA-N n-tert-butyl-5-(2,3-dimethoxyphenyl)-1h-imidazo[1,2-b][1,2,4]triazol-6-amine Chemical compound COC1=CC=CC(C2=C(N3NC=NC3=N2)NC(C)(C)C)=C1OC NNXDJLDBAFGYGK-UHFFFAOYSA-N 0.000 claims description 2
- VPNVFECJWAWSGE-UHFFFAOYSA-N n-tert-butyl-5-(2-methylphenyl)-1h-imidazo[1,2-b][1,2,4]triazol-6-amine Chemical compound CC1=CC=CC=C1C1=C(NC(C)(C)C)N2NC=NC2=N1 VPNVFECJWAWSGE-UHFFFAOYSA-N 0.000 claims description 2
- YLTNLWIFQBFPSB-UHFFFAOYSA-N n-tert-butyl-5-naphthalen-1-yl-1h-imidazo[1,2-b][1,2,4]triazol-6-amine Chemical compound C1=CC=C2C(C3=C(N4NC=NC4=N3)NC(C)(C)C)=CC=CC2=C1 YLTNLWIFQBFPSB-UHFFFAOYSA-N 0.000 claims description 2
- KROZLPZGYWISDQ-UHFFFAOYSA-N n-tert-butyl-6-(2-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-amine Chemical compound COC1=CC=CC=C1C1=C(NC(C)(C)C)N2C=CSC2=N1 KROZLPZGYWISDQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 238000010490 three component reaction Methods 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims 1
- PPPXRIUHKCOOMU-UHFFFAOYSA-N 1-(benzenesulfonyl)pyrrole Chemical compound C1=CC=CN1S(=O)(=O)C1=CC=CC=C1 PPPXRIUHKCOOMU-UHFFFAOYSA-N 0.000 claims 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims 1
- XZOPHRPAUNJURP-UHFFFAOYSA-N 5-ethyl-2-phenoxyphenol Chemical compound OC1=CC(CC)=CC=C1OC1=CC=CC=C1 XZOPHRPAUNJURP-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000004799 bromophenyl group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B40/00—Libraries per se, e.g. arrays, mixtures
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1999148436 DE19948436B4 (de) | 1999-10-08 | 1999-10-08 | Bicyclische Imidazo-5-aminderivate |
| DE19948434A DE19948434A1 (de) | 1999-10-08 | 1999-10-08 | Substanzbibliothek enthaltend bicyclische Imidazo-5-amine und/oder bicyclische Imidazo-3-amine |
| PCT/EP2000/009097 WO2001027118A2 (de) | 1999-10-08 | 2000-09-18 | Bicyclische imidazo-5-yl-aminderivate |
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| SK4642002A3 true SK4642002A3 (en) | 2002-09-10 |
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| SK464-2002A SK4642002A3 (en) | 1999-10-08 | 2000-09-18 | Bicyclic imidazo-5-yl-amine derivatives method for producing thereof, use thereof and pharmaceutical compositions containing said compounds |
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| JP (1) | JP2003511456A (ja) |
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| CN (1) | CN1211385C (ja) |
| AR (1) | AR030030A1 (ja) |
| AT (1) | ATE413403T1 (ja) |
| AU (1) | AU781227B2 (ja) |
| BR (1) | BR0014817A (ja) |
| CA (1) | CA2388476C (ja) |
| CO (1) | CO5200851A1 (ja) |
| CY (1) | CY1110416T1 (ja) |
| CZ (1) | CZ20021242A3 (ja) |
| DE (1) | DE50015443D1 (ja) |
| DK (1) | DK1218383T3 (ja) |
| ES (1) | ES2316388T3 (ja) |
| HK (1) | HK1047746A1 (ja) |
| HU (1) | HUP0203140A3 (ja) |
| IL (2) | IL149010A0 (ja) |
| MX (1) | MXPA02002837A (ja) |
| NO (1) | NO20021566L (ja) |
| PE (1) | PE20010638A1 (ja) |
| PL (1) | PL355019A1 (ja) |
| PT (1) | PT1218383E (ja) |
| RU (1) | RU2002110112A (ja) |
| SI (1) | SI1218383T1 (ja) |
| SK (1) | SK4642002A3 (ja) |
| UY (1) | UY26370A1 (ja) |
| WO (1) | WO2001027118A2 (ja) |
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| PL355019A1 (en) * | 1999-10-08 | 2004-03-22 | Grunenthal Gmbh | Bicyclic imidazo-5-yl-amine derivatives |
| US6380228B1 (en) | 2000-04-10 | 2002-04-30 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| DE10043845A1 (de) * | 2000-09-06 | 2002-03-14 | Gruenenthal Gmbh | Verfahren zur Messung der Aktivität der NO-Synthase |
| KR100647583B1 (ko) * | 2003-10-07 | 2006-11-17 | 삼성에스디아이 주식회사 | 이미다졸 고리 함유 화합물 및 이를 이용한 유기 전계발광 소자 |
| WO2006065788A2 (en) * | 2004-12-13 | 2006-06-22 | Glaxo Group Limited | Novel muscarinic acetylcholine receptor antagonists |
| US7923041B2 (en) * | 2005-02-03 | 2011-04-12 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| DE102006011574A1 (de) * | 2006-03-10 | 2007-10-31 | Grünenthal GmbH | Substituierte Imidazo[2,1-b]thiazol-Verbindungen und ihre Verwendung zur Herstellung von Arzneimitteln |
| AU2007267121A1 (en) * | 2006-05-31 | 2007-12-06 | Galapagos N.V. | Triazolopyrazine compounds useful for the treatment of degenerative & inflammatory diseases |
| US8227603B2 (en) * | 2006-08-01 | 2012-07-24 | Cytokinetics, Inc. | Modulating skeletal muscle |
| US20100173930A1 (en) * | 2006-08-01 | 2010-07-08 | Alex Muci | Certain Chemical Entities, Compositions and Methods |
| EP2995619B1 (en) * | 2006-08-02 | 2019-09-25 | Cytokinetics, Inc. | Certain chemical entities comprising imidazopyrimidines, compositions and methods |
| US8299248B2 (en) * | 2006-08-02 | 2012-10-30 | Cytokinetics, Incorporated | Certain 1H-imidazo[4,5-b]pyrazin-2(3H)-ones and 1H-imidazo[4,5-b]pyrazin-2-ols and methods for their use |
| US7851484B2 (en) * | 2007-03-30 | 2010-12-14 | Cytokinetics, Inc. | Certain chemical entities, compositions, and methods |
| CA2704645A1 (en) * | 2007-11-09 | 2009-05-14 | The Salk Institute For Biological Studies | Non-nucleoside reverse transcriptase inhibitors |
| PT2266990E (pt) * | 2008-04-15 | 2012-12-27 | Eisai R&D Man Co Ltd | Composto de 3-fenilpirazolo[5,1-b]tiazole |
| WO2010147898A2 (en) * | 2009-06-15 | 2010-12-23 | Rigel Pharmaceuticals, Inc. | Small molecule inhibitors of spleen tyrosine kinase (syk) |
| AR078521A1 (es) | 2009-10-08 | 2011-11-16 | Eisai R&D Man Co Ltd | Compuesto pirazolotiazol |
| KR101951220B1 (ko) | 2011-07-13 | 2019-02-22 | 싸이토키네틱스, 인코포레이티드 | 조합 als 치료법 |
| PL2841437T3 (pl) | 2012-04-26 | 2017-12-29 | Bristol-Myers Squibb Company | Pochodne imidazotiadiazolu i imidazopirazyny jako inhibitory receptora 4 (par4) aktywowanego proteazą do leczenia agregacji płytek |
| CA2871599A1 (en) | 2012-04-26 | 2013-10-31 | Bristol-Myers Squibb Company | Imidazothiadiazole and imidazopyridazine derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation |
| AU2013251683A1 (en) | 2012-04-26 | 2014-12-18 | Bristol-Myers Squibb Company | Imidazothiadiazole derivatives as protease activated receptor 4 (PAR4) inhibitors for treating platelet aggregation |
| US9598419B1 (en) | 2014-06-24 | 2017-03-21 | Universite De Montreal | Imidazotriazine and imidazodiazine compounds |
| US9617279B1 (en) | 2014-06-24 | 2017-04-11 | Bristol-Myers Squibb Company | Imidazooxadiazole compounds |
| KR102599388B1 (ko) * | 2017-09-01 | 2023-11-09 | 현대자동차주식회사 | 피드백 제어방법 및 시스템 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW274551B (ja) * | 1991-04-16 | 1996-04-21 | Takeda Pharm Industry Co Ltd | |
| PL355019A1 (en) * | 1999-10-08 | 2004-03-22 | Grunenthal Gmbh | Bicyclic imidazo-5-yl-amine derivatives |
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2000
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- 2000-09-18 KR KR1020027004442A patent/KR20020068515A/ko not_active Application Discontinuation
- 2000-09-18 CZ CZ20021242A patent/CZ20021242A3/cs unknown
- 2000-09-18 PT PT00967693T patent/PT1218383E/pt unknown
- 2000-09-18 MX MXPA02002837A patent/MXPA02002837A/es active IP Right Grant
- 2000-09-18 DK DK00967693T patent/DK1218383T3/da active
- 2000-09-18 WO PCT/EP2000/009097 patent/WO2001027118A2/de active IP Right Grant
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- 2000-09-18 CN CNB008163650A patent/CN1211385C/zh not_active Expired - Fee Related
- 2000-09-18 DE DE50015443T patent/DE50015443D1/de not_active Expired - Lifetime
- 2000-09-18 HU HU0203140A patent/HUP0203140A3/hu unknown
- 2000-09-18 AU AU77772/00A patent/AU781227B2/en not_active Ceased
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- 2000-09-18 SK SK464-2002A patent/SK4642002A3/sk not_active Application Discontinuation
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- 2000-09-18 RU RU2002110112/04A patent/RU2002110112A/ru not_active Application Discontinuation
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- 2000-10-02 CO CO00074644A patent/CO5200851A1/es not_active Application Discontinuation
- 2000-10-05 UY UY26370A patent/UY26370A1/es not_active Application Discontinuation
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2002
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- 2002-04-04 IL IL149010A patent/IL149010A/en not_active IP Right Cessation
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2003
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2009
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