ES2548571T3 - Derivados de imidazo[2,1-b][1,3,4]tiadiazol - Google Patents

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Publication number

ES2548571T3

ES2548571T3 ES10715318.1T ES10715318T ES2548571T3 ES 2548571 T3 ES2548571 T3 ES 2548571T3 ES 10715318 T ES10715318 T ES 10715318T ES 2548571 T3 ES2548571 T3 ES 2548571T3

Authority

ES

Spain

Prior art keywords

optionally substituted

substituents selected

imidazo

alkyl

phenyl

Prior art date

2009-04-02

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.)

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• MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 197
• 125000001424 substituent group Chemical group 0.000 claims abstract description 149
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 81
• 125000003118 aryl group Chemical group 0.000 claims abstract description 66
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
• 239000001257 hydrogen Substances 0.000 claims abstract description 51
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 45
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 41
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 39
• 150000002148 esters Chemical class 0.000 claims abstract description 37
• 150000001408 amides Chemical class 0.000 claims abstract description 31
• 125000005843 halogen group Chemical group 0.000 claims abstract description 28
• 125000004429 atom Chemical group 0.000 claims abstract description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
• 150000003839 salts Chemical class 0.000 claims abstract description 25
• 125000004122 cyclic group Chemical group 0.000 claims abstract description 22
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 21
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 21
• 239000011737 fluorine Substances 0.000 claims abstract description 21
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 20
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 19
• 125000002619 bicyclic group Chemical group 0.000 claims abstract description 19
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 16
• 239000012453 solvate Substances 0.000 claims abstract description 16
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 9
• 150000001732 carboxylic acid derivatives Chemical group 0.000 claims abstract description 7
• 125000000172 C5-C10 aryl group Chemical group 0.000 claims abstract description 6
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims abstract description 3
• 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims abstract description 3
• 125000002843 carboxylic acid group Chemical group 0.000 claims abstract 4
• 238000009434 installation Methods 0.000 claims abstract 2
• 239000000203 mixture Substances 0.000 claims description 106
• -1 5- (2- (4- (2-Morpholinoethoxy) -3-methylphenyl) -6-methylimidazo [2,1-b] [1,3,4] thiadiazol-5-yl) -3- (trifluoromethyl) pyridine- 2-amine Chemical compound 0.000 claims description 78
• 238000006243 chemical reaction Methods 0.000 claims description 56
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 50
• 238000000034 method Methods 0.000 claims description 36
• 201000010099 disease Diseases 0.000 claims description 34
• 206010028980 Neoplasm Diseases 0.000 claims description 29
• 238000011282 treatment Methods 0.000 claims description 28
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 201000011510 cancer Diseases 0.000 claims description 21
• 230000008569 process Effects 0.000 claims description 19
• 208000035475 disorder Diseases 0.000 claims description 16
• 238000002360 preparation method Methods 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 14
• 150000002431 hydrogen Chemical class 0.000 claims description 13
• 239000002671 adjuvant Substances 0.000 claims description 12
• 239000003085 diluting agent Substances 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
• 229940124597 therapeutic agent Drugs 0.000 claims description 10
• 230000002062 proliferating effect Effects 0.000 claims description 8
• 201000001320 Atherosclerosis Diseases 0.000 claims description 7
• 208000020084 Bone disease Diseases 0.000 claims description 6
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 4
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 4
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 4
• 206010061218 Inflammation Diseases 0.000 claims description 4
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 4
• 208000009905 Neurofibromatoses Diseases 0.000 claims description 4
• 208000031481 Pathologic Constriction Diseases 0.000 claims description 4
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 208000026935 allergic disease Diseases 0.000 claims description 4
• 206010003246 arthritis Diseases 0.000 claims description 4
• 230000004663 cell proliferation Effects 0.000 claims description 4
• 239000013066 combination product Substances 0.000 claims description 4
• 229940127555 combination product Drugs 0.000 claims description 4
• 208000027866 inflammatory disease Diseases 0.000 claims description 4
• 230000004054 inflammatory process Effects 0.000 claims description 4
• 201000004931 neurofibromatosis Diseases 0.000 claims description 4
• 208000015768 polyposis Diseases 0.000 claims description 4
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 4
• 208000037803 restenosis Diseases 0.000 claims description 4
• 230000002792 vascular Effects 0.000 claims description 4
• AKQNKCWKASWGJF-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-(2-methylsulfanylpyrimidin-5-yl)imidazo[2,1-b][1,3,4]thiadiazole Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC=C2C1=CN=C(SC)N=C1 AKQNKCWKASWGJF-UHFFFAOYSA-N 0.000 claims description 3
• RWWQTLSCTIVVRI-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-(2-methylsulfinylpyrimidin-5-yl)imidazo[2,1-b][1,3,4]thiadiazole Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC=C2C1=CN=C(S(C)=O)N=C1 RWWQTLSCTIVVRI-UHFFFAOYSA-N 0.000 claims description 3
• RIEWWHCPDPFGRL-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-(2-piperazin-1-ylpyrimidin-5-yl)imidazo[2,1-b][1,3,4]thiadiazole Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC=C2C1=CN=C(N2CCNCC2)N=C1 RIEWWHCPDPFGRL-UHFFFAOYSA-N 0.000 claims description 3
• ZMXPAPWWMBZNTB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-(6-methoxypyridin-3-yl)-6-methylimidazo[2,1-b][1,3,4]thiadiazole Chemical compound C1=NC(OC)=CC=C1C1=C(C)N=C2N1N=C(C=1C=C(OC)C(OC)=CC=1)S2 ZMXPAPWWMBZNTB-UHFFFAOYSA-N 0.000 claims description 3
• OMOMOEILAGAXCG-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[6-piperazin-1-yl-5-(trifluoromethyl)pyridin-3-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC=C2C(C=C1C(F)(F)F)=CN=C1N1CCNCC1 OMOMOEILAGAXCG-UHFFFAOYSA-N 0.000 claims description 3
• 208000024827 Alzheimer disease Diseases 0.000 claims description 3
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 3
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 3
• 208000035473 Communicable disease Diseases 0.000 claims description 3
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 3
• 206010019842 Hepatomegaly Diseases 0.000 claims description 3
• 208000029462 Immunodeficiency disease Diseases 0.000 claims description 3
• 206010062016 Immunosuppression Diseases 0.000 claims description 3
• 208000012902 Nervous system disease Diseases 0.000 claims description 3
• 210000001744 T-lymphocyte Anatomy 0.000 claims description 3
• 108090000190 Thrombin Proteins 0.000 claims description 3
• 208000036142 Viral infection Diseases 0.000 claims description 3
• 230000004913 activation Effects 0.000 claims description 3
• 230000030833 cell death Effects 0.000 claims description 3
• 208000015114 central nervous system disease Diseases 0.000 claims description 3
• 230000001066 destructive effect Effects 0.000 claims description 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
• 230000007368 endocrine function Effects 0.000 claims description 3
• 239000005556 hormone Substances 0.000 claims description 3
• 229940088597 hormone Drugs 0.000 claims description 3
• 208000026278 immune system disease Diseases 0.000 claims description 3
• 230000001506 immunosuppresive effect Effects 0.000 claims description 3
• 208000019423 liver disease Diseases 0.000 claims description 3
• 230000007102 metabolic function Effects 0.000 claims description 3
• 210000000056 organ Anatomy 0.000 claims description 3
• 230000001575 pathological effect Effects 0.000 claims description 3
• 230000036262 stenosis Effects 0.000 claims description 3
• 208000037804 stenosis Diseases 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
• 229960004072 thrombin Drugs 0.000 claims description 3
• 238000002054 transplantation Methods 0.000 claims description 3
• 230000009385 viral infection Effects 0.000 claims description 3
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 2
• ZUQBOFLJCDUPLL-UHFFFAOYSA-N 2,5-bis(3,4-dimethoxyphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazole Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC(C)=C2C1=CC=C(OC)C(OC)=C1 ZUQBOFLJCDUPLL-UHFFFAOYSA-N 0.000 claims description 2
• RSFFPCCWMHUQLL-UHFFFAOYSA-N 2,5-bis(3,4-dimethoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazole Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC=C2C1=CC=C(OC)C(OC)=C1 RSFFPCCWMHUQLL-UHFFFAOYSA-N 0.000 claims description 2
• HUTMTGYICXIPIA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-(3-fluoro-4-methylsulfonylphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazole Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC(C)=C2C1=CC=C(S(C)(=O)=O)C(F)=C1 HUTMTGYICXIPIA-UHFFFAOYSA-N 0.000 claims description 2
• LZOMSHMFRHDKIM-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-(5-methoxypyridin-3-yl)imidazo[2,1-b][1,3,4]thiadiazole Chemical compound COC1=CN=CC(C=2N3N=C(SC3=NC=2)C=2C=C(OC)C(OC)=CC=2)=C1 LZOMSHMFRHDKIM-UHFFFAOYSA-N 0.000 claims description 2
• IAGZELQWGJLYMJ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC=C2C1=CN=C(N2CCN(C)CC2)N=C1 IAGZELQWGJLYMJ-UHFFFAOYSA-N 0.000 claims description 2
• TYUAFSOVSKDGIB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-[6-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)pyridin-3-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC=C2C(C=C1C(F)(F)F)=CN=C1N1CCN(C)CC1 TYUAFSOVSKDGIB-UHFFFAOYSA-N 0.000 claims description 2
• RSNYNBZETHZDBU-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-6-methyl-5-pyridin-3-ylimidazo[2,1-b][1,3,4]thiadiazole Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC(C)=C2C1=CC=CN=C1 RSNYNBZETHZDBU-UHFFFAOYSA-N 0.000 claims description 2
• NWZFUZORNWLJOQ-UHFFFAOYSA-N 2-(3-methoxy-4-piperidin-4-yloxyphenyl)-5-(6-methoxypyridin-3-yl)imidazo[2,1-b][1,3,4]thiadiazole Chemical compound C1=NC(OC)=CC=C1C1=CN=C2N1N=C(C=1C=C(OC)C(OC3CCNCC3)=CC=1)S2 NWZFUZORNWLJOQ-UHFFFAOYSA-N 0.000 claims description 2
• QWFJSMCERPTIKB-UHFFFAOYSA-N 5-[2-(3,4-dimethoxyphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazol-5-yl]-1h-pyridin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC(C)=C2C1=CC=C(O)N=C1 QWFJSMCERPTIKB-UHFFFAOYSA-N 0.000 claims description 2
• BYZDTGPFYDEWOP-UHFFFAOYSA-N 5-[2-(3,4-dimethoxyphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazol-5-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC(C)=C2C1=CN=C(N)C(C(F)(F)F)=C1 BYZDTGPFYDEWOP-UHFFFAOYSA-N 0.000 claims description 2
• AENJYOUQPLPPMH-UHFFFAOYSA-N 5-[2-(3,4-dimethoxyphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazol-5-yl]pyridine-2-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC(C)=C2C1=CC=C(C#N)N=C1 AENJYOUQPLPPMH-UHFFFAOYSA-N 0.000 claims description 2
• LQKQKJIRALJYEC-UHFFFAOYSA-N 5-[2-(3,4-dimethoxyphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazol-5-yl]pyrimidin-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC(C)=C2C1=CN=C(N)N=C1 LQKQKJIRALJYEC-UHFFFAOYSA-N 0.000 claims description 2
• NJNVCRQDBBXSPC-UHFFFAOYSA-N 5-[2-(3,4-dimethoxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]pyridine-2-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C(S1)=NN2C1=NC=C2C1=CC=C(C#N)N=C1 NJNVCRQDBBXSPC-UHFFFAOYSA-N 0.000 claims description 2
• QXVYXFLTVOHZHN-UHFFFAOYSA-N 5-[2-(3-methoxy-4-piperidin-4-yloxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound COC1=CC(C=2SC3=NC=C(N3N=2)C=2C=C(C(N)=NC=2)C(F)(F)F)=CC=C1OC1CCNCC1 QXVYXFLTVOHZHN-UHFFFAOYSA-N 0.000 claims description 2
• UAQOVZOKHHGSKX-UHFFFAOYSA-N 5-[5-(4-methylsulfonylphenyl)imidazo[2,1-b][1,3,4]thiadiazol-2-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C2N1N=C(C=1C=C(C(N)=NC=1)C(F)(F)F)S2 UAQOVZOKHHGSKX-UHFFFAOYSA-N 0.000 claims description 2
• USYWDCIKSBYJOL-UHFFFAOYSA-N 5-[5-(6-fluoropyridin-3-yl)imidazo[2,1-b][1,3,4]thiadiazol-2-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C(S1)=NN2C1=NC=C2C1=CC=C(F)N=C1 USYWDCIKSBYJOL-UHFFFAOYSA-N 0.000 claims description 2
• 208000012124 AIDS-related disease Diseases 0.000 claims description 2
• 208000006011 Stroke Diseases 0.000 claims description 2
• WJBBQRAWMLWHGB-UHFFFAOYSA-N methyl 4-[2-[6-amino-5-(trifluoromethyl)pyridin-3-yl]imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-2-methoxybenzoate Chemical compound C1=C(OC)C(C(=O)OC)=CC=C1C1=CN=C2N1N=C(C=1C=C(C(N)=NC=1)C(F)(F)F)S2 WJBBQRAWMLWHGB-UHFFFAOYSA-N 0.000 claims description 2
• KDUXFZBQLUGABF-UHFFFAOYSA-N n-[3-[5-[6-amino-5-(trifluoromethyl)pyridin-3-yl]imidazo[2,1-b][1,3,4]thiadiazol-2-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2SC3=NC=C(N3N=2)C=2C=C(C(N)=NC=2)C(F)(F)F)=C1 KDUXFZBQLUGABF-UHFFFAOYSA-N 0.000 claims description 2
• UJAVCRZZTZJNJN-UHFFFAOYSA-N n-[[3-[5-[6-amino-5-(trifluoromethyl)pyridin-3-yl]imidazo[2,1-b][1,3,4]thiadiazol-2-yl]phenyl]methyl]methanesulfonamide Chemical compound CS(=O)(=O)NCC1=CC=CC(C=2SC3=NC=C(N3N=2)C=2C=C(C(N)=NC=2)C(F)(F)F)=C1 UJAVCRZZTZJNJN-UHFFFAOYSA-N 0.000 claims description 2
• 230000000414 obstructive effect Effects 0.000 claims description 2
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
• 229940127557 pharmaceutical product Drugs 0.000 claims description 2
• XGDIPYSICGUMJK-UHFFFAOYSA-N tert-butyl 5-[5-[6-amino-5-(trifluoromethyl)pyridin-3-yl]imidazo[2,1-b][1,3,4]thiadiazol-2-yl]-2-oxospiro[1h-indole-3,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC21C1=CC(C=3SC4=NC=C(N4N=3)C=3C=C(C(N)=NC=3)C(F)(F)F)=CC=C1NC2=O XGDIPYSICGUMJK-UHFFFAOYSA-N 0.000 claims description 2
• 208000015181 infectious disease Diseases 0.000 claims 2
• 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 2
• YBPINIBANNZBJJ-UHFFFAOYSA-N 2,4-difluoro-n-[2-methoxy-5-(5-pyridazin-4-ylimidazo[2,1-b][1,3,4]thiadiazol-2-yl)pyridin-3-yl]benzenesulfonamide Chemical compound COC1=NC=C(C=2SC3=NC=C(N3N=2)C=2C=NN=CC=2)C=C1NS(=O)(=O)C1=CC=C(F)C=C1F YBPINIBANNZBJJ-UHFFFAOYSA-N 0.000 claims 1
• BRXLDWIKOGTBQT-UHFFFAOYSA-N 2-[4-[5-[6-amino-5-(trifluoromethyl)pyridin-3-yl]-6-methylimidazo[2,1-b][1,3,4]thiadiazol-2-yl]-2-methoxyphenoxy]-n,n-dimethylacetamide Chemical compound C1=C(OCC(=O)N(C)C)C(OC)=CC(C=2SC3=NC(C)=C(N3N=2)C=2C=C(C(N)=NC=2)C(F)(F)F)=C1 BRXLDWIKOGTBQT-UHFFFAOYSA-N 0.000 claims 1
• WTNIEFBGQTVEOI-UHFFFAOYSA-N 5-[2-(3-morpholin-4-ylsulfonylphenyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=CN=C2N1N=C(C=1C=C(C=CC=1)S(=O)(=O)N1CCOCC1)S2 WTNIEFBGQTVEOI-UHFFFAOYSA-N 0.000 claims 1
• IADDDQNVAOFGGG-UHFFFAOYSA-N 5-[2-(4-morpholin-4-ylsulfonylphenyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=CN=C2N1N=C(C=1C=CC(=CC=1)S(=O)(=O)N1CCOCC1)S2 IADDDQNVAOFGGG-UHFFFAOYSA-N 0.000 claims 1
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• 239000001433 sodium tartrate Substances 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 196
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 195
• 229910052796 boron Inorganic materials 0.000 description 107
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 101
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 94
• 239000000047 product Substances 0.000 description 93
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 85
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 83
• 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 79
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 68
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 67
• 239000002904 solvent Substances 0.000 description 66
• 239000007787 solid Substances 0.000 description 65
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 60
• 238000005160 1H NMR spectroscopy Methods 0.000 description 59
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