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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- Engineering & Computer Science (AREA)
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- General Chemical & Material Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Neurosurgery (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3020305A1 true CA3020305A1 (en) | 2017-10-12 |
Family
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| CA3020305A Abandoned CA3020305A1 (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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|---|---|
| US (3) | US10787454B2 (OSRAM) |
| EP (1) | EP3440083A4 (OSRAM) |
| JP (1) | JP7046827B2 (OSRAM) |
| CA (1) | CA3020305A1 (OSRAM) |
| MX (1) | MX2018012208A (OSRAM) |
| WO (1) | WO2017176961A1 (OSRAM) |
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| DK3215511T3 (da) | 2014-11-06 | 2024-05-13 | Bial R&D Invest S A | Substituerede pyrazolo(1,5-a)pyrimidiner og deres anvendelse i behandlingen af medicinske lidelser |
| CA2966581A1 (en) | 2014-11-06 | 2016-05-12 | Lysosomal Therapeutics Inc. | Substituted pyrrolo[1,2-a]pyrimidines and their use in the treatment of medical disorders |
| ES2958391T3 (es) | 2014-11-06 | 2024-02-08 | Bial R&D Invest S A | Imidazo[1,5-a]pirimidinas sustituidas y su uso en el tratamiento de trastornos médicos |
| WO2017176960A1 (en) | 2016-04-06 | 2017-10-12 | Lysosomal Therapeutics Inc. | Pyrazolo[1,5-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| JP7046827B2 (ja) | 2016-04-06 | 2022-04-04 | 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 | イミダゾ［１，５－ａ］ピリミジニルカルボキサミド化合物および医学的障害の処置におけるその使用 |
| WO2017176962A1 (en) | 2016-04-06 | 2017-10-12 | Lysosomal Therapeutics, Inc. | Pyrrolo[1,2-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| US11345698B2 (en) | 2016-05-05 | 2022-05-31 | Bial—R&D Investments, S.A. | Substituted imidazo[1,2-a]pyridines, substituted imidazo[1,2-a]pyrazines, related compounds, and their use in the treatment of medical disorders |
| BR112018072552A8 (pt) | 2016-05-05 | 2023-03-14 | Lysosomal Therapeutics Inc | Compostos de imidazo [1,2-b]piridazinas e imidazo [1,5-b] piridazinas substituídas, composição farmacêutica que os compreende e seu uso no tratamento de distúrbios médicos |
| CN116283995B (zh) * | 2022-09-08 | 2023-12-29 | 华中科技大学同济医学院附属同济医院 | 一种脂酰辅酶a合成酶短链家族成员3的激动剂及其应用 |
| CN116514665B (zh) * | 2023-05-09 | 2025-01-28 | 南京优氟医药科技有限公司 | 一种(r)-2,2,2-三氟-1-苯乙胺盐酸盐的制备方法 |
| WO2025146216A1 (zh) * | 2024-01-05 | 2025-07-10 | 成都赜灵生物医药科技有限公司 | 六并五氮杂环酰胺类化合物及其用途 |
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2017
- 2017-04-06 JP JP2018552716A patent/JP7046827B2/ja not_active Expired - Fee Related
- 2017-04-06 EP EP17779798.2A patent/EP3440083A4/en not_active Withdrawn
- 2017-04-06 CA CA3020305A patent/CA3020305A1/en not_active Abandoned
- 2017-04-06 WO PCT/US2017/026282 patent/WO2017176961A1/en not_active Ceased
- 2017-04-06 US US16/091,316 patent/US10787454B2/en active Active
- 2017-04-06 MX MX2018012208A patent/MX2018012208A/es unknown
- 2017-08-16 US US15/678,476 patent/US9920061B2/en active Active
-
2020
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| Publication number | Publication date |
|---|---|
| US20210309661A1 (en) | 2021-10-07 |
| JP2019510794A (ja) | 2019-04-18 |
| MX2018012208A (es) | 2019-03-28 |
| US11453675B2 (en) | 2022-09-27 |
| US20190119283A1 (en) | 2019-04-25 |
| WO2017176961A1 (en) | 2017-10-12 |
| US10787454B2 (en) | 2020-09-29 |
| US20170349599A1 (en) | 2017-12-07 |
| EP3440083A4 (en) | 2019-09-18 |
| JP7046827B2 (ja) | 2022-04-04 |
| EP3440083A1 (en) | 2019-02-13 |
| US9920061B2 (en) | 2018-03-20 |
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