CA3020305A1 - Imidazo [1,5-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders - Google Patents
Imidazo [1,5-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders Download PDFInfo
- Publication number
- CA3020305A1 CA3020305A1 CA3020305A CA3020305A CA3020305A1 CA 3020305 A1 CA3020305 A1 CA 3020305A1 CA 3020305 A CA3020305 A CA 3020305A CA 3020305 A CA3020305 A CA 3020305A CA 3020305 A1 CA3020305 A1 CA 3020305A1
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- CA
- Canada
- Prior art keywords
- compound
- cycloalkyl
- alkyl
- membered
- psi
- 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.)
- Abandoned
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- HYQUTQMHYJEWLG-UHFFFAOYSA-N N=1C=2N(C=CC=1C(=O)N)C=NC=2 Chemical class N=1C=2N(C=CC=1C(=O)N)C=NC=2 HYQUTQMHYJEWLG-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000011282 treatment Methods 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 477
- 238000000034 method Methods 0.000 claims abstract description 469
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 41
- 208000035475 disorder Diseases 0.000 claims abstract description 36
- 208000009829 Lewy Body Disease Diseases 0.000 claims abstract description 29
- 201000002832 Lewy body dementia Diseases 0.000 claims abstract description 27
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 24
- 208000015872 Gaucher disease Diseases 0.000 claims abstract description 22
- 208000001089 Multiple system atrophy Diseases 0.000 claims abstract description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 244
- -1 C1-4haloalkoxyl Chemical group 0.000 claims description 167
- 229910052736 halogen Inorganic materials 0.000 claims description 100
- 150000002367 halogens Chemical class 0.000 claims description 99
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 82
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 77
- 125000001424 substituent group Chemical group 0.000 claims description 69
- 125000000623 heterocyclic group Chemical group 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 55
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 52
- 125000003545 alkoxy group Chemical group 0.000 claims description 50
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 47
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 47
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 47
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims description 26
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 23
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 21
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 19
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 17
- 125000002541 furyl group Chemical group 0.000 claims description 17
- 125000002883 imidazolyl group Chemical group 0.000 claims description 17
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 15
- 125000002971 oxazolyl group Chemical group 0.000 claims description 15
- 125000000335 thiazolyl group Chemical group 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 12
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 11
- 206010012289 Dementia Diseases 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 8
- 208000020925 Bipolar disease Diseases 0.000 claims description 7
- 206010030348 Open-Angle Glaucoma Diseases 0.000 claims description 7
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 7
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
- 206010015037 epilepsy Diseases 0.000 claims description 7
- 208000024714 major depressive disease Diseases 0.000 claims description 7
- 201000006417 multiple sclerosis Diseases 0.000 claims description 7
- 208000030761 polycystic kidney disease Diseases 0.000 claims description 7
- 201000000980 schizophrenia Diseases 0.000 claims description 7
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 7
- 201000009273 Endometriosis Diseases 0.000 claims description 6
- 208000034578 Multiple myelomas Diseases 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 241000282414 Homo sapiens Species 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 4
- 125000004970 halomethyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 177
- 150000002894 organic compounds Chemical class 0.000 abstract description 33
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 544
- 239000007787 solid Substances 0.000 description 445
- 238000004128 high performance liquid chromatography Methods 0.000 description 255
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 242
- 239000000243 solution Substances 0.000 description 120
- 238000005160 1H NMR spectroscopy Methods 0.000 description 118
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 78
- 238000005481 NMR spectroscopy Methods 0.000 description 76
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- 239000000706 filtrate Substances 0.000 description 64
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 53
- 229910052938 sodium sulfate Inorganic materials 0.000 description 52
- 235000011152 sodium sulphate Nutrition 0.000 description 52
- 239000007832 Na2SO4 Substances 0.000 description 51
- 101150041968 CDC13 gene Proteins 0.000 description 50
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 50
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 150000003857 carboxamides Chemical class 0.000 description 34
- 238000010898 silica gel chromatography Methods 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- OOXIEUXBOSSXJM-UHFFFAOYSA-N 2-cyclopropylpropan-2-amine Chemical compound CC(C)(N)C1CC1 OOXIEUXBOSSXJM-UHFFFAOYSA-N 0.000 description 32
- 239000003921 oil Substances 0.000 description 32
- 239000012074 organic phase Substances 0.000 description 32
- 235000019198 oils Nutrition 0.000 description 31
- IXCXVGWKYIDNOS-BYPYZUCNSA-N (1s)-1-cyclopropylethanamine Chemical compound C[C@H](N)C1CC1 IXCXVGWKYIDNOS-BYPYZUCNSA-N 0.000 description 28
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 28
- 239000004698 Polyethylene Substances 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 25
- 238000002360 preparation method Methods 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 125000003636 chemical group Chemical group 0.000 description 24
- 239000012044 organic layer Substances 0.000 description 24
- 150000001408 amides Chemical class 0.000 description 21
- 239000003814 drug Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000012267 brine Substances 0.000 description 18
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- LJGQUFKFKWJNJR-UHFFFAOYSA-N ClC1=NC=2N(C(=C1)C)C=NC=2C(=O)OCC Chemical compound ClC1=NC=2N(C(=C1)C)C=NC=2C(=O)OCC LJGQUFKFKWJNJR-UHFFFAOYSA-N 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
- 239000012230 colorless oil Substances 0.000 description 15
- 230000008878 coupling Effects 0.000 description 15
- 238000010168 coupling process Methods 0.000 description 15
- 238000005859 coupling reaction Methods 0.000 description 15
- NJMORFFDAXJHHM-UHFFFAOYSA-N ethyl 4-amino-1h-imidazole-5-carboxylate Chemical compound CCOC(=O)C=1NC=NC=1N NJMORFFDAXJHHM-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- PXELQDUJCLEIOT-UHFFFAOYSA-N ClC1=NC=2N(C(=C1)C)C=NC=2C(=O)O Chemical compound ClC1=NC=2N(C(=C1)C)C=NC=2C(=O)O PXELQDUJCLEIOT-UHFFFAOYSA-N 0.000 description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 229940079593 drug Drugs 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 125000003342 alkenyl group Chemical group 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 12
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 125000003710 aryl alkyl group Chemical group 0.000 description 11
- 125000005842 heteroatom Chemical group 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 238000002953 preparative HPLC Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- FRDAKAYQSQLWRW-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-fluorophenyl)ethanamine Chemical compound FC(F)(F)C(N)C1=CC=C(F)C=C1 FRDAKAYQSQLWRW-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 229910000024 caesium carbonate Inorganic materials 0.000 description 9
- 125000002993 cycloalkylene group Chemical group 0.000 description 9
- 239000002552 dosage form Substances 0.000 description 9
- 125000003226 pyrazolyl group Chemical group 0.000 description 9
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 8
- VUGCBIWQHSRQBZ-UHFFFAOYSA-N 2-methylbut-3-yn-2-amine Chemical compound CC(C)(N)C#C VUGCBIWQHSRQBZ-UHFFFAOYSA-N 0.000 description 8
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 150000008282 halocarbons Chemical class 0.000 description 8
- 150000004045 organic chlorine compounds Chemical class 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 229940124530 sulfonamide Drugs 0.000 description 8
- 230000001225 therapeutic effect Effects 0.000 description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 125000002755 pyrazolinyl group Chemical group 0.000 description 7
- 125000006413 ring segment Chemical group 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- NLLGFYPSWCMUIV-UHFFFAOYSA-N (3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1 NLLGFYPSWCMUIV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000003368 amide group Chemical group 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
- 125000002636 imidazolinyl group Chemical group 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002674 ointment Substances 0.000 description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 description 6
- 125000005968 oxazolinyl group Chemical group 0.000 description 6
- 125000004043 oxo group Chemical group O=* 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 description 6
- 125000002769 thiazolinyl group Chemical group 0.000 description 6
- 125000005881 triazolinyl group Chemical group 0.000 description 6
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- A61P7/06—Antianaemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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Applications Claiming Priority (3)
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| US201662318936P | 2016-04-06 | 2016-04-06 | |
| US62/318,936 | 2016-04-06 | ||
| PCT/US2017/026282 WO2017176961A1 (en) | 2016-04-06 | 2017-04-06 | Imidazo [1,5-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
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| CA3020305A1 true CA3020305A1 (en) | 2017-10-12 |
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| EP (1) | EP3440083A4 (enExample) |
| JP (1) | JP7046827B2 (enExample) |
| CA (1) | CA3020305A1 (enExample) |
| MX (1) | MX2018012208A (enExample) |
| WO (1) | WO2017176961A1 (enExample) |
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| KR20230104752A9 (ko) | 2016-04-06 | 2024-11-15 | 비알 - 알&디 인베스트먼츠, 에스.에이. | 피라졸로[1,5-a]피리미디닐 카르복스아미드 화합물및 의학적 장애의 치료에서의 그의 용도 |
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| JP7164774B2 (ja) | 2016-05-05 | 2022-11-02 | ビアル－アール・アンド・ディ・インベストメンツ・ソシエダーデ・アノニマ | 置換イミダゾ［１，２－ｂ］ピリダジン、置換イミダゾ［１，５－ｂ］ピリダジン、関連化合物、および医学的障害の治療におけるその使用 |
| EP3452455A4 (en) | 2016-05-05 | 2019-11-13 | Lysosomal Therapeutics Inc. | SUBSTITUTED IMDAZO [1,2-] PYRIDINES, SUBSTITUTED IMIDAZO [1,2-] PYRAZINES, RELATED COMPOUNDS AND THEIR USE IN THE TREATMENT OF ILLNESSES |
| WO2017192929A1 (en) | 2016-05-05 | 2017-11-09 | Lysosomal Therapeutics Inc. | SUBSTITUTED PYRROLO[1,2-α]TRIAZINES AND RELATED COMPOUNDS AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS |
| JP2021506920A (ja) | 2017-12-21 | 2021-02-22 | リソソーマル・セラピューティクス・インコーポレイテッドＬｙｓｏｓｏｍａｌ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｉｎｃ． | 結晶性の置換シクロヘキシルピラゾロ［１，５−ａ］ピリミジニルカルボキサミド化合物およびその治療的使用 |
-
2017
- 2017-04-06 US US16/091,316 patent/US10787454B2/en active Active
- 2017-04-06 EP EP17779798.2A patent/EP3440083A4/en not_active Withdrawn
- 2017-04-06 JP JP2018552716A patent/JP7046827B2/ja active Active
- 2017-04-06 MX MX2018012208A patent/MX2018012208A/es unknown
- 2017-04-06 WO PCT/US2017/026282 patent/WO2017176961A1/en not_active Ceased
- 2017-04-06 CA CA3020305A patent/CA3020305A1/en not_active Abandoned
- 2017-08-16 US US15/678,476 patent/US9920061B2/en active Active
-
2020
- 2020-08-10 US US16/989,254 patent/US11453675B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2017176961A1 (en) | 2017-10-12 |
| US10787454B2 (en) | 2020-09-29 |
| JP2019510794A (ja) | 2019-04-18 |
| EP3440083A4 (en) | 2019-09-18 |
| US20190119283A1 (en) | 2019-04-25 |
| US20170349599A1 (en) | 2017-12-07 |
| JP7046827B2 (ja) | 2022-04-04 |
| US11453675B2 (en) | 2022-09-27 |
| EP3440083A1 (en) | 2019-02-13 |
| MX2018012208A (es) | 2019-03-28 |
| US20210309661A1 (en) | 2021-10-07 |
| US9920061B2 (en) | 2018-03-20 |
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