RU2013105450A - Новые производные гомопиперзина в качестве ингибиторов протеинтирозинкиназ и их фармацевтическое применение - Google Patents
Новые производные гомопиперзина в качестве ингибиторов протеинтирозинкиназ и их фармацевтическое применение Download PDFInfo
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- RU2013105450A RU2013105450A RU2013105450/04A RU2013105450A RU2013105450A RU 2013105450 A RU2013105450 A RU 2013105450A RU 2013105450/04 A RU2013105450/04 A RU 2013105450/04A RU 2013105450 A RU2013105450 A RU 2013105450A RU 2013105450 A RU2013105450 A RU 2013105450A
- Authority
- RU
- Russia
- Prior art keywords
- diazaspiro
- pyrrolo
- pyrimidin
- nonan
- methanone
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title 1
- -1 cyano, hydroxy Chemical group 0.000 claims abstract 64
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 40
- 150000001875 compounds Chemical class 0.000 claims abstract 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 31
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract 27
- 229910052736 halogen Inorganic materials 0.000 claims abstract 18
- 150000002367 halogens Chemical group 0.000 claims abstract 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 18
- 239000001257 hydrogen Substances 0.000 claims abstract 18
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 12
- 150000002431 hydrogen Chemical group 0.000 claims abstract 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
- 125000003118 aryl group Chemical group 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 125000003342 alkenyl group Chemical group 0.000 claims 13
- 125000000304 alkynyl group Chemical group 0.000 claims 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 10
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 208000023275 Autoimmune disease Diseases 0.000 claims 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 206010012438 Dermatitis atopic Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000004681 Psoriasis Diseases 0.000 claims 4
- 201000008937 atopic dermatitis Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 201000006417 multiple sclerosis Diseases 0.000 claims 4
- 208000017520 skin disease Diseases 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims 3
- 208000011231 Crohn disease Diseases 0.000 claims 3
- 201000004624 Dermatitis Diseases 0.000 claims 3
- 208000002249 Diabetes Complications Diseases 0.000 claims 3
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 3
- 241001303601 Rosacea Species 0.000 claims 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 3
- 125000004946 alkenylalkyl group Chemical group 0.000 claims 3
- 125000005038 alkynylalkyl group Chemical group 0.000 claims 3
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 208000010928 autoimmune thyroid disease Diseases 0.000 claims 3
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 208000030533 eye disease Diseases 0.000 claims 3
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims 3
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims 3
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims 3
- 210000000987 immune system Anatomy 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 230000002458 infectious effect Effects 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 208000032839 leukemia Diseases 0.000 claims 3
- 206010025135 lupus erythematosus Diseases 0.000 claims 3
- 208000002780 macular degeneration Diseases 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- 201000004700 rosacea Diseases 0.000 claims 3
- VIJCSROECFZLKA-UHFFFAOYSA-N (5-methyl-1h-pyrazol-3-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound N1N=C(C)C=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 VIJCSROECFZLKA-UHFFFAOYSA-N 0.000 claims 2
- DNLYKIBLZSHIRI-UHFFFAOYSA-N (5-methyl-1h-pyrazol-3-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound N1N=C(C)C=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 DNLYKIBLZSHIRI-UHFFFAOYSA-N 0.000 claims 2
- HIAZHBYRJBITLA-UHFFFAOYSA-N 1h-imidazol-5-yl-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound C=1NC=NC=1C(=O)N(C1)CCN(C=2C=3C=CNC=3N=CN=2)CC21CC2 HIAZHBYRJBITLA-UHFFFAOYSA-N 0.000 claims 2
- ZKZWUNHNOIHYGY-UHFFFAOYSA-N 1h-imidazol-5-yl-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound C=1NC=NC=1C(=O)N1CCCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 ZKZWUNHNOIHYGY-UHFFFAOYSA-N 0.000 claims 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- 125000005324 aryloxy alkyloxy group Chemical group 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 206010023332 keratitis Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- HZMNSCPCLOAADH-UHFFFAOYSA-N (1-phenylcyclopropyl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound C1CC1(C=1C=CC=CC=1)C(=O)N(C1)CCN(C=2C=3C=CNC=3N=CN=2)CC21CC2 HZMNSCPCLOAADH-UHFFFAOYSA-N 0.000 claims 1
- UMZMVIHVPPGAEF-UHFFFAOYSA-N (2,3-dimethoxyphenyl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound COC1=CC=CC(C(=O)N2CC3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1OC UMZMVIHVPPGAEF-UHFFFAOYSA-N 0.000 claims 1
- CIMQNOZEUKUAPE-UHFFFAOYSA-N (2,5-dimethylpyrazol-3-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound CN1N=C(C)C=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 CIMQNOZEUKUAPE-UHFFFAOYSA-N 0.000 claims 1
- IDVKHQGJCUQGDA-UHFFFAOYSA-N (2,5-dimethylpyrazol-3-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound CN1N=C(C)C=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 IDVKHQGJCUQGDA-UHFFFAOYSA-N 0.000 claims 1
- PUHZAQXQFPAMSD-UHFFFAOYSA-N (2-chlorophenyl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound ClC1=CC=CC=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 PUHZAQXQFPAMSD-UHFFFAOYSA-N 0.000 claims 1
- WIWRPGLMUZSAKL-UHFFFAOYSA-N (2-chlorophenyl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound ClC1=CC=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 WIWRPGLMUZSAKL-UHFFFAOYSA-N 0.000 claims 1
- GWXVWAVDSYEYPS-UHFFFAOYSA-N (2-fluorophenyl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound FC1=CC=CC=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 GWXVWAVDSYEYPS-UHFFFAOYSA-N 0.000 claims 1
- AMUAFMVUIRXNNS-UHFFFAOYSA-N (2-methoxypyridin-3-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound COC1=NC=CC=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 AMUAFMVUIRXNNS-UHFFFAOYSA-N 0.000 claims 1
- CXHTYRFGMIXAFZ-UHFFFAOYSA-N (2-methylphenyl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound CC1=CC=CC=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 CXHTYRFGMIXAFZ-UHFFFAOYSA-N 0.000 claims 1
- AHIYFSIDLZEJPL-UHFFFAOYSA-N (2-methylphenyl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound CC1=CC=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 AHIYFSIDLZEJPL-UHFFFAOYSA-N 0.000 claims 1
- RQVHOQOLHIPUEN-UHFFFAOYSA-N (2-methylpyridin-3-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound CC1=NC=CC=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 RQVHOQOLHIPUEN-UHFFFAOYSA-N 0.000 claims 1
- CZLBVCVCIKFBAJ-UHFFFAOYSA-N (2-methylpyridin-3-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound CC1=NC=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 CZLBVCVCIKFBAJ-UHFFFAOYSA-N 0.000 claims 1
- KJBZCGGZULYOCO-UHFFFAOYSA-N (2-methylpyridin-4-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound C1=NC(C)=CC(C(=O)N2CC3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 KJBZCGGZULYOCO-UHFFFAOYSA-N 0.000 claims 1
- FAAJQZNAGDCIMI-UHFFFAOYSA-N (2-methylpyridin-4-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound C1=NC(C)=CC(C(=O)N2C3(CC3)CN(CCC2)C=2C=3C=CNC=3N=CN=2)=C1 FAAJQZNAGDCIMI-UHFFFAOYSA-N 0.000 claims 1
- JDHPUMKMIAARIK-CQSZACIVSA-N (2r)-1-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonane-8-carbonyl]pyrrolidine-2-carbonitrile Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)CN1C(=O)N1CCC[C@@H]1C#N JDHPUMKMIAARIK-CQSZACIVSA-N 0.000 claims 1
- JDHPUMKMIAARIK-AWEZNQCLSA-N (2s)-1-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonane-8-carbonyl]pyrrolidine-2-carbonitrile Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)CN1C(=O)N1CCC[C@H]1C#N JDHPUMKMIAARIK-AWEZNQCLSA-N 0.000 claims 1
- MLBGYNJQRALAPI-UHFFFAOYSA-N (3,5-dimethoxyphenyl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound COC1=CC(OC)=CC(C(=O)N2CC3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 MLBGYNJQRALAPI-UHFFFAOYSA-N 0.000 claims 1
- FFCLCQAAWRYFNU-UHFFFAOYSA-N (3,5-dimethyl-1,2-oxazol-4-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound CC1=NOC(C)=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 FFCLCQAAWRYFNU-UHFFFAOYSA-N 0.000 claims 1
- ROIOPWDUNBZLAT-UHFFFAOYSA-N (3,5-dimethyl-1,2-oxazol-4-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound CC1=NOC(C)=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 ROIOPWDUNBZLAT-UHFFFAOYSA-N 0.000 claims 1
- GZBVZGCHDBQKDP-UHFFFAOYSA-N (3-chlorophenyl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound ClC1=CC=CC(C(=O)N2CC3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 GZBVZGCHDBQKDP-UHFFFAOYSA-N 0.000 claims 1
- CKPWLXQDULJNMK-UHFFFAOYSA-N (3-chlorophenyl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound ClC1=CC=CC(C(=O)N2C3(CC3)CN(CCC2)C=2C=3C=CNC=3N=CN=2)=C1 CKPWLXQDULJNMK-UHFFFAOYSA-N 0.000 claims 1
- SQWISDWIVXFEKR-UHFFFAOYSA-N (3-ethyl-4,5-dihydro-1,2-oxazol-5-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound C1C(CC)=NOC1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 SQWISDWIVXFEKR-UHFFFAOYSA-N 0.000 claims 1
- SPAAIIIEXZELRQ-UHFFFAOYSA-N (3-methyl-1,2-oxazol-4-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound CC1=NOC=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 SPAAIIIEXZELRQ-UHFFFAOYSA-N 0.000 claims 1
- CPYRGZVNRRNJIU-UHFFFAOYSA-N (3-methyl-1,2-oxazol-4-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound CC1=NOC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 CPYRGZVNRRNJIU-UHFFFAOYSA-N 0.000 claims 1
- JQMBCKAMLFJMBB-UHFFFAOYSA-N (3-methyl-1,2-oxazol-5-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound O1N=C(C)C=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 JQMBCKAMLFJMBB-UHFFFAOYSA-N 0.000 claims 1
- RYFRNGJOTICOPE-UHFFFAOYSA-N (3-methyl-1,2-thiazol-5-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound S1N=C(C)C=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 RYFRNGJOTICOPE-UHFFFAOYSA-N 0.000 claims 1
- JXZSVITXTJYYGO-UHFFFAOYSA-N (3-methyl-1,2-thiazol-5-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound S1N=C(C)C=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 JXZSVITXTJYYGO-UHFFFAOYSA-N 0.000 claims 1
- KMEWCPJCUBXZSH-UHFFFAOYSA-N (3-methylimidazol-4-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound CN1C=NC=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 KMEWCPJCUBXZSH-UHFFFAOYSA-N 0.000 claims 1
- HZCASOOJBJYHQL-UHFFFAOYSA-N (3-methylimidazol-4-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound CN1C=NC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 HZCASOOJBJYHQL-UHFFFAOYSA-N 0.000 claims 1
- QOYZGVMSDVXFLE-UHFFFAOYSA-N (3-methylpyridin-4-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound CC1=CN=CC=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 QOYZGVMSDVXFLE-UHFFFAOYSA-N 0.000 claims 1
- URSLSNQGIZMBSX-UHFFFAOYSA-N (3-methylpyridin-4-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound CC1=CN=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 URSLSNQGIZMBSX-UHFFFAOYSA-N 0.000 claims 1
- CWEMDCYMQJBEIZ-UHFFFAOYSA-N (4-amino-1,2,5-oxadiazol-3-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound NC1=NON=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 CWEMDCYMQJBEIZ-UHFFFAOYSA-N 0.000 claims 1
- FUYSRNWXOSZVMS-UHFFFAOYSA-N (4-chlorophenyl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 FUYSRNWXOSZVMS-UHFFFAOYSA-N 0.000 claims 1
- MKNYWGXTYRTGPU-UHFFFAOYSA-N (4-chlorophenyl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 MKNYWGXTYRTGPU-UHFFFAOYSA-N 0.000 claims 1
- UAPZYDKCISXBMD-UHFFFAOYSA-N (4-fluorophenyl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 UAPZYDKCISXBMD-UHFFFAOYSA-N 0.000 claims 1
- OZUXIANABJCPAV-UHFFFAOYSA-N (4-methoxythiophen-2-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound COC1=CSC(C(=O)N2CC3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 OZUXIANABJCPAV-UHFFFAOYSA-N 0.000 claims 1
- WKKDRZOHSVCUTQ-UHFFFAOYSA-N (4-methyl-1,3-oxazol-5-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound N1=COC(C(=O)N2CC3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1C WKKDRZOHSVCUTQ-UHFFFAOYSA-N 0.000 claims 1
- UKYVCXCVEOAAPZ-UHFFFAOYSA-N (4-methyl-1,3-oxazol-5-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound N1=COC(C(=O)N2C3(CC3)CN(CCC2)C=2C=3C=CNC=3N=CN=2)=C1C UKYVCXCVEOAAPZ-UHFFFAOYSA-N 0.000 claims 1
- YYAMEIPEECDPFU-UHFFFAOYSA-N (4-methyl-1h-pyrrol-2-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound CC1=CNC(C(=O)N2C3(CC3)CN(CCC2)C=2C=3C=CNC=3N=CN=2)=C1 YYAMEIPEECDPFU-UHFFFAOYSA-N 0.000 claims 1
- NFOADZYWXJCNPU-UHFFFAOYSA-N (4-methylpyridin-3-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound CC1=CC=NC=C1C(=O)N1CC2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 NFOADZYWXJCNPU-UHFFFAOYSA-N 0.000 claims 1
- UOIFQHVXTCWLIZ-UHFFFAOYSA-N (4-methylpyridin-3-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound CC1=CC=NC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CCC1 UOIFQHVXTCWLIZ-UHFFFAOYSA-N 0.000 claims 1
- GADMYKNGDQCNQJ-UHFFFAOYSA-N (4-methylthiadiazol-5-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound N1=NSC(C(=O)N2CC3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1C GADMYKNGDQCNQJ-UHFFFAOYSA-N 0.000 claims 1
- YPDWYVPPLASDMY-UHFFFAOYSA-N (4-methylthiadiazol-5-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound N1=NSC(C(=O)N2C3(CC3)CN(CCC2)C=2C=3C=CNC=3N=CN=2)=C1C YPDWYVPPLASDMY-UHFFFAOYSA-N 0.000 claims 1
- GHBSEPZTCBOPRV-UHFFFAOYSA-N (5-chloro-1h-1,2,4-triazol-3-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound N1C(Cl)=NC(C(=O)N2CC3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=N1 GHBSEPZTCBOPRV-UHFFFAOYSA-N 0.000 claims 1
- YUYUHOLHMDENDF-UHFFFAOYSA-N (5-chloro-1h-1,2,4-triazol-3-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound N1C(Cl)=NC(C(=O)N2C3(CC3)CN(CCC2)C=2C=3C=CNC=3N=CN=2)=N1 YUYUHOLHMDENDF-UHFFFAOYSA-N 0.000 claims 1
- QNPUUVINTOITBB-UHFFFAOYSA-N (5-fluoropyridin-3-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound FC1=CN=CC(C(=O)N2CC3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 QNPUUVINTOITBB-UHFFFAOYSA-N 0.000 claims 1
- XLJZXACOKNMACD-UHFFFAOYSA-N (5-fluoropyridin-3-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound FC1=CN=CC(C(=O)N2C3(CC3)CN(CCC2)C=2C=3C=CNC=3N=CN=2)=C1 XLJZXACOKNMACD-UHFFFAOYSA-N 0.000 claims 1
- AFVLIVYQEFQFNS-UHFFFAOYSA-N (5-methyl-1,2-oxazol-3-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound O1C(C)=CC(C(=O)N2CC3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=N1 AFVLIVYQEFQFNS-UHFFFAOYSA-N 0.000 claims 1
- NODDZULLAUOZOH-UHFFFAOYSA-N (5-methyl-1,2-oxazol-3-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound O1C(C)=CC(C(=O)N2C3(CC3)CN(CCC2)C=2C=3C=CNC=3N=CN=2)=N1 NODDZULLAUOZOH-UHFFFAOYSA-N 0.000 claims 1
- MKJLTHSGTKCEFT-UHFFFAOYSA-N (5-methyl-1,2-oxazol-4-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound O1N=CC(C(=O)N2CC3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1C MKJLTHSGTKCEFT-UHFFFAOYSA-N 0.000 claims 1
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- VIZKLZUPUCRISP-UHFFFAOYSA-N (5-methyl-1,2-thiazol-4-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound S1N=CC(C(=O)N2C3(CC3)CN(CCC2)C=2C=3C=CNC=3N=CN=2)=C1C VIZKLZUPUCRISP-UHFFFAOYSA-N 0.000 claims 1
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- DGALRVDETBRHJK-UHFFFAOYSA-N (5-methyl-1h-pyrazol-4-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound N1N=CC(C(=O)N2CC3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1C DGALRVDETBRHJK-UHFFFAOYSA-N 0.000 claims 1
- NQHGJYINHULTFT-UHFFFAOYSA-N (5-methyl-1h-pyrazol-4-yl)-[8-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,8-diazaspiro[2.6]nonan-4-yl]methanone Chemical compound N1N=CC(C(=O)N2C3(CC3)CN(CCC2)C=2C=3C=CNC=3N=CN=2)=C1C NQHGJYINHULTFT-UHFFFAOYSA-N 0.000 claims 1
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- CXJGLZBXUCNNSG-UHFFFAOYSA-N 1h-pyrazol-4-yl-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound C1=NNC=C1C(=O)N(C1)CCN(C=2C=3C=CNC=3N=CN=2)CC21CC2 CXJGLZBXUCNNSG-UHFFFAOYSA-N 0.000 claims 1
- KVXOVHTUZOWJSY-UHFFFAOYSA-N 1h-pyrazol-5-yl-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.6]nonan-8-yl]methanone Chemical compound C1=CNN=C1C(=O)N(C1)CCN(C=2C=3C=CNC=3N=CN=2)CC21CC2 KVXOVHTUZOWJSY-UHFFFAOYSA-N 0.000 claims 1
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- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
Classifications
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36309510P | 2010-07-09 | 2010-07-09 | |
| US61/363,095 | 2010-07-09 | ||
| PCT/DK2011/000080 WO2012003829A1 (en) | 2010-07-09 | 2011-07-08 | Novel homopiperazine derivatives as protein tyrosine kinase inhibitors and pharmaceutical use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2013105450A true RU2013105450A (ru) | 2014-08-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2013105450/04A RU2013105450A (ru) | 2010-07-09 | 2011-07-08 | Новые производные гомопиперзина в качестве ингибиторов протеинтирозинкиназ и их фармацевтическое применение |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9586961B2 (https=) |
| EP (1) | EP2590981B1 (https=) |
| JP (1) | JP2013533868A (https=) |
| CN (1) | CN102985425A (https=) |
| RU (1) | RU2013105450A (https=) |
| TW (1) | TW201204732A (https=) |
| WO (1) | WO2012003829A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104072499A (zh) * | 2013-03-29 | 2014-10-01 | 黄传满 | 哌嗪取代嘧啶类化合物及其用途 |
| CN103242321A (zh) * | 2013-05-21 | 2013-08-14 | 苏州科捷生物医药有限公司 | 苄基哌嗪类化合物及其抗肿瘤用途 |
| CN103396414B (zh) * | 2013-07-16 | 2015-06-03 | 浙江医药高等专科学校 | 咪唑取代的噻唑并环己烷类化合物、及其抗肿瘤用途 |
| MX368464B (es) * | 2013-12-05 | 2019-10-02 | Pfizer | Acrilamidas de pirrolo[2,3-d]pirimidinilo, pirrolo[2,3-b]pirazinil o y pirrolo[2,3-d]piridinilo. |
| AR101214A1 (es) * | 2014-07-22 | 2016-11-30 | Bayer Cropscience Ag | Ciano-cicloalquilpenta-2,4-dienos, ciano-cicloalquilpent-2-en-4-inas, ciano-heterociclilpenta-2,4-dienos y ciano-heterociclilpent-2-en-4-inas sustituidos como principios activos contra el estrés abiótico de plantas |
| CN105712998B (zh) * | 2014-12-05 | 2019-12-13 | 上海润诺生物科技有限公司 | 氮杂吲哚类衍生物、其制备方法及其在医药上的应用 |
| CN109689663B (zh) * | 2016-09-14 | 2023-04-14 | 詹森药业有限公司 | Menin-mll相互作用的螺二环抑制剂 |
| CN110291090A (zh) * | 2017-01-20 | 2019-09-27 | 利奥制药有限公司 | 作为新型jak激酶抑制剂的双环胺 |
| CN110248663A (zh) * | 2017-02-03 | 2019-09-17 | 利奥制药有限公司 | 作为新型JAK激酶抑制剂的5-(7H-吡咯并[2,3-d]嘧啶-4-基)-5-氮杂螺[2.5]辛烷-8-甲酸衍生物 |
| CN108069986B (zh) * | 2017-12-08 | 2018-10-02 | 牡丹江医学院 | 一种治疗角膜炎的活性药物及其制备方法 |
| WO2020092015A1 (en) | 2018-11-02 | 2020-05-07 | University Of Rochester | Therapeutic mitigation of epithelial infection |
| CN114599364A (zh) | 2019-09-05 | 2022-06-07 | 因赛特公司 | 用于减少特应性皮炎瘙痒的鲁索替尼制剂 |
| US11992490B2 (en) | 2019-10-16 | 2024-05-28 | Incyte Corporation | Use of JAK1 inhibitors for the treatment of cutaneous lupus erythematosus and Lichen planus (LP) |
| JP7554829B2 (ja) | 2019-12-19 | 2024-09-20 | ヤンセン ファーマシューティカ エヌ．ベー． | 置換直鎖スピロ誘導体 |
Family Cites Families (9)
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| PA8474101A1 (es) * | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| BR9911365A (pt) * | 1998-06-19 | 2001-03-13 | Pfizer Prod Inc | Compostos pirrolo[2,3-d]pirimidina |
| WO2005117909A2 (en) | 2004-04-23 | 2005-12-15 | Exelixis, Inc. | Kinase modulators and methods of use |
| PL2049529T3 (pl) | 2006-07-14 | 2011-01-31 | Merck Sharp & Dohme | Podstawione związki diazepanowe - antagoniści receptora oreksyny |
| RU2009140319A (ru) * | 2007-04-02 | 2011-05-10 | Палау Фарма С.А. (Es) | Производные пирролпиримидина |
| WO2009017838A2 (en) | 2007-08-01 | 2009-02-05 | Exelixis, Inc. | Combinations of jak-2 inhibitors and other agents |
| EP2188289B1 (en) * | 2007-08-08 | 2015-10-28 | Lexicon Pharmaceuticals, Inc. | (7h-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazines as kinase inhibitors for the treatment of cancer and inflammation |
| UY31631A1 (es) | 2008-02-06 | 2009-09-30 | Nuevos derivados de 7-fenil-7h-pirrolo-[2,3d]-pirimidin-2-il-amino, sales de los mismos, procesos para su preparacion, composiciones farmacéuticas que los comprenden y aplicaciones | |
| NZ588830A (en) | 2008-04-22 | 2012-11-30 | Portola Pharm Inc | Inhibitors of protein kinases |
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- 2011-07-08 RU RU2013105450/04A patent/RU2013105450A/ru not_active Application Discontinuation
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- 2011-07-08 EP EP11738151.7A patent/EP2590981B1/en not_active Not-in-force
Also Published As
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|---|---|
| CN102985425A (zh) | 2013-03-20 |
| EP2590981B1 (en) | 2014-09-03 |
| WO2012003829A1 (en) | 2012-01-12 |
| TW201204732A (en) | 2012-02-01 |
| EP2590981A1 (en) | 2013-05-15 |
| US20130172325A1 (en) | 2013-07-04 |
| US9586961B2 (en) | 2017-03-07 |
| JP2013533868A (ja) | 2013-08-29 |
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