JP2018507167A5 - - Google Patents
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- Publication number
- JP2018507167A5 JP2018507167A5 JP2017529681A JP2017529681A JP2018507167A5 JP 2018507167 A5 JP2018507167 A5 JP 2018507167A5 JP 2017529681 A JP2017529681 A JP 2017529681A JP 2017529681 A JP2017529681 A JP 2017529681A JP 2018507167 A5 JP2018507167 A5 JP 2018507167A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- pyrazolo
- pyrazin
- pentan
- alkyl
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 249
- 150000001875 compounds Chemical class 0.000 claims description 109
- -1 cyclopropylidene Chemical group 0.000 claims description 72
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 58
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000008194 pharmaceutical composition Substances 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 125000005227 alkyl sulfonate group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 210000004027 cell Anatomy 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 101100062121 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cyc-1 gene Proteins 0.000 claims description 6
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 4
- 125000002393 azetidinyl group Chemical group 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 230000000968 intestinal effect Effects 0.000 claims description 4
- 206010025135 lupus erythematosus Diseases 0.000 claims description 4
- HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 claims description 4
- 229960000951 mycophenolic acid Drugs 0.000 claims description 4
- HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 208000017520 skin disease Diseases 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- UYDZAZNDTNXIDX-OAHLLOKOSA-N (2R)-2-methyl-3-[4-[4-(1-pentan-3-ylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-6-yl]pyrazol-1-yl]propan-1-ol Chemical compound C[C@@H](CO)CN1N=CC(=C1)C=1N=C(C=2N(C=1)N=CC=2)C=1C=NN(C=1)C(CC)CC UYDZAZNDTNXIDX-OAHLLOKOSA-N 0.000 claims description 2
- BNGZGHJLRLYZLX-XPCCGILXSA-N (2R)-3-[4-[4-[1-(1,1,1-trifluorobutan-2-yl)pyrazol-4-yl]pyrazolo[1,5-a]pyrazin-6-yl]pyrazol-1-yl]propane-1,2-diol Chemical compound CCC(N1C=C(C=N1)C1=NC(=CN2N=CC=C12)C1=CN(C[C@@H](O)CO)N=C1)C(F)(F)F BNGZGHJLRLYZLX-XPCCGILXSA-N 0.000 claims description 2
- IHZCYGIKKXIIOQ-QAPCUYQASA-N (2R)-3-[4-[4-[1-[(3S)-2,2-difluoropentan-3-yl]pyrazol-4-yl]pyrazolo[1,5-a]pyrazin-6-yl]pyrazol-1-yl]propane-1,2-diol Chemical compound FC(C)([C@H](CC)N1N=CC(=C1)C=1C=2N(C=C(N=1)C=1C=NN(C=1)C[C@H](CO)O)N=CC=2)F IHZCYGIKKXIIOQ-QAPCUYQASA-N 0.000 claims description 2
- ITIFSOSGXOSPND-DUSLRRAJSA-N (2R)-3-[4-[4-[1-[1-(3,3-difluorocyclobutyl)propyl]pyrazol-4-yl]pyrazolo[1,5-a]pyrazin-6-yl]pyrazol-1-yl]propane-1,2-diol Chemical compound FC1(CC(C1)C(CC)N1N=CC(=C1)C=1C=2N(C=C(N=1)C=1C=NN(C=1)C[C@H](CO)O)N=CC=2)F ITIFSOSGXOSPND-DUSLRRAJSA-N 0.000 claims description 2
- UYDZAZNDTNXIDX-HNNXBMFYSA-N (2S)-2-methyl-3-[4-[4-(1-pentan-3-ylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-6-yl]pyrazol-1-yl]propan-1-ol Chemical compound C[C@H](CO)CN1N=CC(=C1)C=1N=C(C=2N(C=1)N=CC=2)C=1C=NN(C=1)C(CC)CC UYDZAZNDTNXIDX-HNNXBMFYSA-N 0.000 claims description 2
- BIQLFOVHGXFGRI-GOSISDBHSA-N (3R)-4-[4-[4-(1-pentan-3-ylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-6-yl]pyrazol-1-yl]butane-1,3-diol Chemical compound CCC(CC)N1N=CC(=C1)C=1C=2N(C=C(N=1)C=1C=NN(C=1)C[C@@H](CCO)O)N=CC=2 BIQLFOVHGXFGRI-GOSISDBHSA-N 0.000 claims description 2
- BIQLFOVHGXFGRI-SFHVURJKSA-N (3S)-4-[4-[4-(1-pentan-3-ylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-6-yl]pyrazol-1-yl]butane-1,3-diol Chemical compound CCC(CC)N1C=C(C=N1)C1=NC(=CN2N=CC=C12)C1=CN(C[C@@H](O)CCO)N=C1 BIQLFOVHGXFGRI-SFHVURJKSA-N 0.000 claims description 2
- VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- KITCYDCXSZDXLF-UHFFFAOYSA-N 1-[2-[4-[4-(1-pentan-3-ylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-6-yl]pyrazol-1-yl]ethyl]piperazin-2-one Chemical compound CCC(CC)N1C=C(C=N1)C1=NC(=CN2N=CC=C12)C1=CN(CCN2CCNCC2=O)N=C1 KITCYDCXSZDXLF-UHFFFAOYSA-N 0.000 claims description 2
- OANLOJFGMDFXLE-UHFFFAOYSA-N 2-[4-[4-(1-pentan-3-ylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-6-yl]pyrazol-1-yl]propane-1,3-diol Chemical compound CCC(CC)N1C=C(C=N1)C1=NC(=CN2N=CC=C12)C1=CN(N=C1)C(CO)CO OANLOJFGMDFXLE-UHFFFAOYSA-N 0.000 claims description 2
- NGAAOEYVYQJXJR-UHFFFAOYSA-N 2-[4-[6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-4-yl]pyrazol-1-yl]butan-1-ol Chemical compound CCC(CO)N1C=C(C=N1)C1=NC(=CN2N=CC=C12)C1=CN(C)N=C1 NGAAOEYVYQJXJR-UHFFFAOYSA-N 0.000 claims description 2
- LNWZSEFHRUUIPB-UHFFFAOYSA-N 2-[4-[6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-4-yl]pyrazol-1-yl]butanoic acid Chemical compound CCC(N1C=C(C=N1)C1=NC(=CN2N=CC=C12)C1=CN(C)N=C1)C(O)=O LNWZSEFHRUUIPB-UHFFFAOYSA-N 0.000 claims description 2
- VHBISBSNGUVGTR-UHFFFAOYSA-N 2-[4-[6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-4-yl]pyrazol-1-yl]cyclopentan-1-ol Chemical compound CN1N=CC(=C1)C=1N=C(C=2N(C=1)N=CC=2)C=1C=NN(C=1)C1C(CCC1)O VHBISBSNGUVGTR-UHFFFAOYSA-N 0.000 claims description 2
- NAGSKGCXMWXMFR-UHFFFAOYSA-N 2-[4-[6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-4-yl]pyrazol-1-yl]propan-1-ol Chemical compound CN1N=CC(=C1)C=1N=C(C=2N(C=1)N=CC=2)C=1C=NN(C=1)C(CO)C NAGSKGCXMWXMFR-UHFFFAOYSA-N 0.000 claims description 2
- NJJAFIJJCFMWSU-UHFFFAOYSA-N 3-[4-[4-(1-pentan-3-ylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-6-yl]pyrazol-1-yl]propan-1-ol Chemical compound CCC(CC)N1N=CC(=C1)C=1C=2N(C=C(N=1)C=1C=NN(C=1)CCCO)N=CC=2 NJJAFIJJCFMWSU-UHFFFAOYSA-N 0.000 claims description 2
- PBBVBJNUBYULHP-UHFFFAOYSA-N 3-[4-[6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-4-yl]pyrazol-1-yl]pentan-1-ol Chemical compound CN1N=CC(=C1)C=1N=C(C=2N(C=1)N=CC=2)C=1C=NN(C=1)C(CCO)CC PBBVBJNUBYULHP-UHFFFAOYSA-N 0.000 claims description 2
- OUPNAKMUTDMSBJ-UHFFFAOYSA-N 4-(1-cycloheptylpyrazol-4-yl)-6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrazine Chemical compound CN1C=C(C=N1)C1=CN2N=CC=C2C(=N1)C1=CN(N=C1)C1CCCCCC1 OUPNAKMUTDMSBJ-UHFFFAOYSA-N 0.000 claims description 2
- XENRQMHKPAIYOY-UHFFFAOYSA-N 4-[1-(1-ethoxyethyl)pyrazol-4-yl]-6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrazine Chemical compound CCOC(C)N1C=C(C=N1)C1=NC(=CN2N=CC=C12)C1=CN(C)N=C1 XENRQMHKPAIYOY-UHFFFAOYSA-N 0.000 claims description 2
- KRTPHJWJOAAJKP-UHFFFAOYSA-N 4-[1-(1-methylcyclopentyl)pyrazol-4-yl]-6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrazine Chemical compound CN1C=C(C=N1)C1=CN2N=CC=C2C(=N1)C1=CN(N=C1)C1(C)CCCC1 KRTPHJWJOAAJKP-UHFFFAOYSA-N 0.000 claims description 2
- CIJCUJJBEHAVNW-UHFFFAOYSA-N 4-[1-(2-methylcycloheptyl)pyrazol-4-yl]-6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrazine Chemical compound CN1N=CC(=C1)C=1N=C(C=2N(C=1)N=CC=2)C=1C=NN(C=1)C1C(CCCCC1)C CIJCUJJBEHAVNW-UHFFFAOYSA-N 0.000 claims description 2
- IRPRWEJXPIFLLK-UHFFFAOYSA-N 4-[1-(3-methylpentan-3-yl)pyrazol-4-yl]-6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrazine Chemical compound CN1N=CC(=C1)C=1N=C(C=2N(C=1)N=CC=2)C=1C=NN(C=1)C(CC)(CC)C IRPRWEJXPIFLLK-UHFFFAOYSA-N 0.000 claims description 2
- 108020004491 Antisense DNA Proteins 0.000 claims description 2
- 108020005544 Antisense RNA Proteins 0.000 claims description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 229940123587 Cell cycle inhibitor Drugs 0.000 claims description 2
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 2
- 229930105110 Cyclosporin A Natural products 0.000 claims description 2
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical group CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 2
- 108010036949 Cyclosporine Proteins 0.000 claims description 2
- 208000002633 Febrile Neutropenia Diseases 0.000 claims description 2
- 206010016654 Fibrosis Diseases 0.000 claims description 2
- 206010020751 Hypersensitivity Diseases 0.000 claims description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 2
- 102000014150 Interferons Human genes 0.000 claims description 2
- 108010050904 Interferons Proteins 0.000 claims description 2
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
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- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims description 2
- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
- OLPLCLUQAIDUNC-UHFFFAOYSA-N [2-[4-[6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyrazin-4-yl]pyrazol-1-yl]cyclopentyl]methanol Chemical compound CN1C=C(C=N1)C1=CN2N=CC=C2C(=N1)C1=CN(N=C1)C1CCCC1CO OLPLCLUQAIDUNC-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
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- 230000002280 anti-androgenic effect Effects 0.000 claims description 2
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- 229960000485 methotrexate Drugs 0.000 claims description 2
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- IDINUJSAMVOPCM-INIZCTEOSA-N n-[(1s)-2-[4-(3-aminopropylamino)butylamino]-1-hydroxy-2-oxoethyl]-7-(diaminomethylideneamino)heptanamide Chemical compound NCCCNCCCCNC(=O)[C@H](O)NC(=O)CCCCCCN=C(N)N IDINUJSAMVOPCM-INIZCTEOSA-N 0.000 claims description 2
- 229960002009 naproxen Drugs 0.000 claims description 2
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
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- 210000000056 organ Anatomy 0.000 claims description 2
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- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 2
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| WO2017156493A1 (en) | 2016-03-11 | 2017-09-14 | Denali Therapeutics Inc. | Compounds, compositions, and methods |
| PL3227297T3 (pl) | 2014-12-05 | 2021-10-25 | Array Biopharma, Inc. | 4,6 podstawione-pyrazolo[1,5-a]pirazyny jako inhibitory kinaz janusowych |
| RU2718902C2 (ru) * | 2016-02-24 | 2020-04-15 | Пфайзер Инк. | Производные пиразоло[1,5-а]пиразин-4-ила в качестве jak-ингибиторов |
| PE20190395A1 (es) | 2016-06-16 | 2019-03-13 | Denali Therapeutics Inc | Pirimidin-2-ilamino-1h-pirazoles como inhibidores de lrrk2 para el uso en el tratamiento de trastornos neurodegenerativos |
| GB201617758D0 (en) * | 2016-10-20 | 2016-12-07 | Almac Discovery Limited | Pharmaceutical compounds |
| CA3049136C (en) | 2017-01-18 | 2022-06-14 | Array Biopharma Inc. | Substituted pyrazolo[1,5-a]pyrazine compounds as ret kinase inhibitors |
| WO2018217946A1 (en) * | 2017-05-24 | 2018-11-29 | Denali Therapeutics Inc. | Compounds, compositions and methods |
| EP3668858A1 (en) | 2017-08-14 | 2020-06-24 | Pfizer Inc | Pyrazolo[1,5-a]pyrazin-4-yl and related derivatives |
| CA3087354C (en) | 2018-01-18 | 2023-01-03 | Array Biopharma Inc. | Substituted pyrrolo[2,3-d]pyrimidines compounds as ret kinase inhibitors |
| WO2019143994A1 (en) | 2018-01-18 | 2019-07-25 | Array Biopharma Inc. | Substituted pyrazolyl[4,3-c]pyridinecompounds as ret kinase inhibitors |
| CA3087578C (en) | 2018-01-18 | 2023-08-08 | Array Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidine compounds as ret kinase inhibitors |
| CN112996794A (zh) | 2018-09-10 | 2021-06-18 | 阿雷生物药品公司 | 作为ret激酶抑制剂的稠合杂环化合物 |
| JP7256291B2 (ja) * | 2019-04-12 | 2023-04-11 | プライムジーン（ベイジン）カンパニー リミテッド | ピラゾロピラジン誘導の化合物、医薬組成物およびその使用 |
| KR102503349B1 (ko) | 2019-05-14 | 2023-02-23 | 프로벤션 바이오, 인코포레이티드 | 제1형 당뇨병을 예방하기 위한 방법 및 조성물 |
| CN113150012B (zh) * | 2020-01-22 | 2023-03-24 | 浙江海正药业股份有限公司 | 吡唑并[1,5-a]吡嗪类衍生物及其制备方法和用途 |
| WO2021198980A1 (en) | 2020-04-04 | 2021-10-07 | Pfizer Inc. | Methods of treating coronavirus disease 2019 |
| US12006366B2 (en) | 2020-06-11 | 2024-06-11 | Provention Bio, Inc. | Methods and compositions for preventing type 1 diabetes |
| IL312782A (en) * | 2021-11-12 | 2024-07-01 | Soter Biopharma Pte Ltd | Pyrazolo fused ring compound and use thereof |
| WO2024235167A1 (zh) * | 2023-05-12 | 2024-11-21 | 海南康哲美丽科技有限公司 | 一种吡唑并吡嗪类化合物及其晶型的制备方法 |
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| DE102007032349A1 (de) * | 2007-07-11 | 2009-01-15 | Bayer Healthcare Ag | Imidazo-, Pyrazolopyrazine und Imidazotriazine und ihre Verwendung |
| KR101790255B1 (ko) * | 2009-12-23 | 2017-10-26 | 다케다 야쿠힌 고교 가부시키가이샤 | Ｓｙｋ 억제제로서의 융합된 헤테로방향족 피롤리디논 |
| EP2526102B1 (en) * | 2010-01-22 | 2017-03-08 | Fundación Centro Nacional de Investigaciones Oncológicas Carlos III | Inhibitors of PI3 kinase |
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| US20110241987A1 (en) * | 2010-04-01 | 2011-10-06 | Smart Technologies Ulc | Interactive input system and information input method therefor |
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| CN103987713A (zh) * | 2011-10-12 | 2014-08-13 | 阵列生物制药公司 | 5,7-取代的咪唑并[1,2-c]嘧啶 |
| WO2013143663A1 (en) * | 2012-03-28 | 2013-10-03 | Merck Patent Gmbh | Bicyclic pyrazinone derivatives |
| PL3227297T3 (pl) | 2014-12-05 | 2021-10-25 | Array Biopharma, Inc. | 4,6 podstawione-pyrazolo[1,5-a]pirazyny jako inhibitory kinaz janusowych |
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