HRP20151126T1 - DERIVATI IMIDAZO[2,1-b][1,3,4]TIADIAZOLA - Google Patents
DERIVATI IMIDAZO[2,1-b][1,3,4]TIADIAZOLA Download PDFInfo
- Publication number
- HRP20151126T1 HRP20151126T1 HRP20151126TT HRP20151126T HRP20151126T1 HR P20151126 T1 HRP20151126 T1 HR P20151126T1 HR P20151126T T HRP20151126T T HR P20151126TT HR P20151126 T HRP20151126 T HR P20151126T HR P20151126 T1 HRP20151126 T1 HR P20151126T1
- Authority
- HR
- Croatia
- Prior art keywords
- imidazo
- phenyl
- optionally substituted
- substituents selected
- alkyl
- Prior art date
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- UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical class N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 title 1
- 125000001424 substituent group Chemical group 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 201000010099 disease Diseases 0.000 claims 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 11
- 150000001408 amides Chemical class 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 150000002148 esters Chemical class 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 201000001320 Atherosclerosis Diseases 0.000 claims 4
- 208000020084 Bone disease Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 239000003085 diluting agent Substances 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 238000000034 method Methods 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 2
- 125000000172 C5-C10 aryl group Chemical group 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims 2
- 208000017701 Endocrine disease Diseases 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims 2
- 206010019842 Hepatomegaly Diseases 0.000 claims 2
- 208000029462 Immunodeficiency disease Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000009905 Neurofibromatoses Diseases 0.000 claims 2
- 208000031481 Pathologic Constriction Diseases 0.000 claims 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- -1 R 21 Chemical compound 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 230000006044 T cell activation Effects 0.000 claims 2
- 108090000190 Thrombin Proteins 0.000 claims 2
- 208000036142 Viral infection Diseases 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 2
- 230000030833 cell death Effects 0.000 claims 2
- 230000004663 cell proliferation Effects 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 230000001066 destructive effect Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000030172 endocrine system disease Diseases 0.000 claims 2
- 239000005556 hormone Substances 0.000 claims 2
- 229940088597 hormone Drugs 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 230000001506 immunosuppresive effect Effects 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 208000030159 metabolic disease Diseases 0.000 claims 2
- 230000002503 metabolic effect Effects 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 201000004931 neurofibromatosis Diseases 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 208000015768 polyposis Diseases 0.000 claims 2
- 230000002980 postoperative effect Effects 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 2
- 208000037804 stenosis Diseases 0.000 claims 2
- 230000036262 stenosis Effects 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 229960004072 thrombin Drugs 0.000 claims 2
- 238000002054 transplantation Methods 0.000 claims 2
- 210000005167 vascular cell Anatomy 0.000 claims 2
- 230000009385 viral infection Effects 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
- 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- ZOLVBLFHQQAYHY-UHFFFAOYSA-N 5-[2-(3-methoxy-4-piperidin-4-yloxyphenyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]pyrimidin-2-amine Chemical compound COC1=CC(C=2SC3=NC=C(N3N=2)C=2C=NC(N)=NC=2)=CC=C1OC1CCNCC1 ZOLVBLFHQQAYHY-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
- OCSQYJPBIKNLOZ-UHFFFAOYSA-N 5-[2-[3-methoxy-4-(2-morpholin-4-ylethoxy)phenyl]-6-methylimidazo[2,1-b][1,3,4]thiadiazol-5-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound COC1=CC(C=2SC3=NC(C)=C(N3N=2)C=2C=C(C(N)=NC=2)C(F)(F)F)=CC=C1OCCN1CCOCC1 OCSQYJPBIKNLOZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- JNIZCLWHOMQGII-UHFFFAOYSA-N 5-[5-[6-amino-5-(trifluoromethyl)pyridin-3-yl]imidazo[2,1-b][1,3,4]thiadiazol-2-yl]spiro[1h-indole-3,4'-piperidine]-2-one Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=CN=C2N1N=C(C=1C=C3C4(CCNCC4)C(=O)NC3=CC=1)S2 JNIZCLWHOMQGII-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 208000012124 AIDS-related disease Diseases 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- COSJKQBNMDCKKT-UHFFFAOYSA-N COC=1C=C(C=CC=1OC)C1=NN2C(S1)=NC=C2C=1C=NC(=NC=1)N1CCN(CC1)C(=O)O Chemical class COC=1C=C(C=CC=1OC)C1=NN2C(S1)=NC=C2C=1C=NC(=NC=1)N1CCN(CC1)C(=O)O COSJKQBNMDCKKT-UHFFFAOYSA-N 0.000 claims 1
- 208000027771 Obstructive airways disease Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 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 1
- 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 1
- DHYKYBOWIVIKSA-UHFFFAOYSA-N tert-butyl n-[2-[4-[5-[6-amino-5-(trifluoromethyl)pyridin-3-yl]-6-methylimidazo[2,1-b][1,3,4]thiadiazol-2-yl]-2-methoxyphenoxy]ethyl]carbamate Chemical compound C1=C(OCCNC(=O)OC(C)(C)C)C(OC)=CC(C=2SC3=NC(C)=C(N3N=2)C=2C=C(C(N)=NC=2)C(F)(F)F)=C1 DHYKYBOWIVIKSA-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/433—Thidiazoles
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Claims (14)
1. Spoj s formulom I,
[image]
pri čemu:
R1 predstavlja:
(i) aril supstituiran s jednim ili više supstituenata odabranih od A1; ili
(ii) heteroaril proizvoljno supstituiran s jednim ili više supstituenata odabranih od A2;
R2 predstavlja vodik ili C1-3 alkil proizvoljno supstituiran s jednim ili više fluoro atoma;
R3 predstavlja aril ili heteroaril, svaki od kojih je proizvoljno supstituiran s jednim ili više supstituenata izabranih redom od A3 i A4;
svaki A1, A2, A3 i A4 neovisno predstavlja, svaki puta kada se ovdje koristi:
(i) Q1;
(ii) C1-12 alkil ili heterocikloalkil, od kojih su oba proizvoljno supstituirana s jednim ili više supstituenata izabranih od =O, =S, =N(R10a) i Q2; ili
(iii) aril ili heteroaril, od kojih su oba proizvoljno supstituirana s jednim ili više supstituenata izabranih od Q3;
svaki Q1, Q2 i Q3 neovisno predstavlja, svaki puta kada se ovdje koristi: halo, -CN, -NO2, -N(R10a)R11a, -OR10a, -C(=Y)-R10a, -C(=Y)-OR10a, -C(=Y)N(R10a)R11a, -OC(=Y)-R10a, -OC(=Y)-OR10a, -OC(=Y)N(R10a)R11a, -OS(O)2OR10a, -OP(=Y)(OR10a)(OR11a), -OP(OR10a)(OR11a), -N(R12a)C(=Y)R11a, -N(R12a)C(=Y)OR11a, -N(R12a)C(=Y)N(R10a)R11a, -NR12aS(O)2R10a, -NR12aS(O)2N(R10a)R11a, -S(O)2N(R10a)R11a, -SC(=Y)R10a, -SC(=Y)OR10a, -SC(=Y)N(R10a)R11a, -S(O)2R10a, -SR10a, -S(O)R10a, -S(O)2OR10a, C1-12 alkil, heterocikloalkil (navedene dvije posljednje skupine su proizvoljno supstituirane s jednim ili više supstituenata izabranih od =O, =S, =N(R20) i E1), aril ili heteroaril (navedene dvije posljednje skupine su proizvoljno supstituirane s jednim ili više supstituenata izabranih od E2);
svaki R10a, R11a i R12a neovisno predstavlja, svaki puta kada se ovdje koristi, vodik, C1-12 alkil, heterocikloalkil (navedene dvije posljednje skupine su proizvoljno supstituirane s jednim ili više supstituenata izabranih od =O, =S, =N(R20) i E3), aril ili heteroaril (navedene dvije posljednje skupine su proizvoljno supstituirane s jednim ili više supstituenata izabranih od E4); ili
bilo koji relevantni par R10a, R11a i R12a može biti povezan zajedno tako da tvori 4- do 20-člani prsten, koji proizvoljno sadrži jedan ili više heteroatoma, proizvoljno sadrži jedno ili više nezasićenja, i koji prsten je proizvoljno supstituiran s jednim ili više supstituenata izabranih od =O, =S, =N(R20) i E5;
svaki E1, E2, E3, E4 i E5 neovisno predstavlja, svaki puta kada se ovdje koristi:
(i) Q4;
(ii) C1-12 alkil ili heterocikloalkil, od kojih su oba proizvoljno supstituirana s jednim ili više supstituenata izabranih od =O i Q5; ili
(iii) aril ili heteroaril, od kojih su oba proizvoljno supstituirana s jednim ili više supstituenata izabranih od Q6;
svaki Q4, Q5 i Q6 neovisno predstavlja, svaki puta kada se ovdje koristi: halo, -CN, -NO2, -N(R20)R21, -OR20, -C(=Y)-R20, -C(=Y)-OR20, -C(=Y)N(R20)R21, -OC(=Y)-R20, -OC(=Y)-OR20, -OC(=Y)N(R20)R21, -OS(O)2OR20, -OP(=Y)(OR20)(OR21), -OP(OR20)(OR21), -N(R22)C(=Y)R21, -N(R22)C(=Y)OR21, -N(R22)C(=Y)N(R20)R21, -NR22S(O)2R20, -NR22S(O)2N(R20)R21, -S(O)2N(R20)R21, -SC(=Y)R20, -SC(=Y)OR20, -SC(=Y)N(R20)R21, -S(O)2R20, -SR20, -S(O)R20, -S(O)2OR20, C1-12 alkil, heterocikloalkil (navedene dvije posljednje skupine su proizvoljno supstituirane s jednim ili više supstituenata izabranih od =O i J1), aril ili heteroaril (navedene dvije posljednje skupine su proizvoljno supstituirane s jednim ili više supstituenata izabranih od J2);
svaki Y neovisno predstavlja, svaki puta kada se ovdje koristi, =O, =S ili =NR23;
svaki R20, R21, R22 i R23 neovisno predstavlja, svaki puta kada se ovdje koristi, vodik, C1-6 alkil, heterocikloalkil (navedene dvije posljednje skupine su proizvoljno supstituirane s jednim ili više supstituenata izabranih od J3 i =O), aril ili heteroaril (navedene dvije posljednje skupine su proizvoljno supstituirane s jednim ili više supstituenata izabranih od J4); ili
bilo koji relevantni par R20, R21 i R22, može biti povezan zajedno tako da tvori 4- do 20-člani prsten, koji proizvoljno sadrži jedan ili više heteroatoma, proizvoljno sadrži jedno ili više nezasićenja, i koji prsten je proizvoljno supstituiran s jednim ili više supstituenata izabranih od J5 i =O;
svaki J1, J2, J3, J4 i J5 neovisno predstavlja, svaki puta kada se ovdje koristi:
(i) Q7;
(ii) C1-6 alkil ili heterocikloalkil, od kojih su oba proizvoljno supstituirana s jednim ili više supstituenata izabranih od =O i Q8; ili
(iii) aril ili heteroaril, od kojih su oba proizvoljno supstituirana s jednim ili više supstituenata izabranih od Q9;
svaki Q7, Q8 i Q9 neovisno predstavlja, svaki puta kada se ovdje koristi: halo, -CN, -N(R50)R51, -OR50, -C(=Ya)-R50, -C(=Ya)-OR50, -C(=Ya)N(R50)R51, -N(R52)C(=Ya)R51, -NR52S(O)2R50, -S(O)2R50, -SR50, -S(O)R50 ili C1-6 alkil proizvoljno supstituiran s jednim ili više fluoro atoma;
svaki Ya neovisno predstavlja, svaki puta kada se ovdje koristi, =O, =S ili =NR53;
svaki R50, R51, R52 i R53 neovisno predstavlja, svaki puta kada se ovdje koristi, vodik ili C1-6 alkil proizvoljno supstituiran s jednim ili više supstituenata izabranih od fluoro, -OR60 i -N(R61)R62; ili
bilo koji relevantni par R50, R51 i R52 može biti povezan zajedno tako da tvori, 3- do 8-člani prsten, koji proizvoljno sadrži jedan ili više heteroatoma, proizvoljno sadrži jedno ili više nezasićenja, i koji prsten je proizvoljno supstituiran s jednim ili više supstituenata izabranih od =O i C1-3 alkila;
R60, R61 i R62 neovisno predstavljaju vodik ili C1-6 alkil proizvoljno supstituiran s jednim ili više fluoro atoma;
ili farmaceutski prihvatljiv ester, amid, solvat ili njihova sol,
pri čemu arilna skupina je, neovisno pri svakom pojavljivanju, skupina C6-10 aril; pri čemu heteroarilna skupina je, neovisno pri svakom pojavljivanju, monociklička, biciklička ili triciklička 5- do 10-člana heteroarilna skupina koja sadrži jedan ili više heteroatoma odabranih od N, O i S, u kojoj je najmanje jedan od prstenova aromatski;
pri čemu heterocikloalkil skupina je, neovisno pri svakom pojavljivanju, nearomatska 5- do 10-člana monociklička ili biciklička heterocikloalkil skupina u kojoj je najmanje jedan od atoma u prstenastom sustavu odabran od N, O i S;
pri čemu farmaceutski prihvatljiv ester je spoj koji sadrži karboksilnu kiselinu s formulom I u kojoj je jedna ili više od navedenih skupina karboksilne kiseline derivatizirana tako da tvori C1-6 alkil, C5-10 aril i/ili C5-10 aril-C1-6 alkil ester; i farmaceutski prihvatljiv amid je spoj koji sadrži karboksilnu kiselinu s formulom I u kojoj je jedna ili više od navedenih skupina karboksilne kiseline derivatizirana tako da tvori amid s formulom -C(O)N(Rz1)Rz2, u kojoj Rz1 i Rz2 neovisno predstavljaju C1-6 alkil, C5-10 aril i/ili C5-10 aril-C1-6 alkil;
pod uvjetom da kada R2 predstavlja H, tada:
(I) kada R1 predstavlja 4-klorofenil, tada R3 ne predstavlja nesupstituirani fenil ili 4-klorofenil;
(II) kada R1 predstavlja 4-metoksifenil, tada R3 ne predstavlja 4-klorofenil ili nesupstituirani fenil.
2. Spoj prema zahtjevu 1, naznačen time da, R1 predstavlja fenil supstituiran s jednim ili više supstituenata odabranih od A1; i/ili R1 predstavlja heteroaril proizvoljno supstituiran s jednim ili više supstituenata odabranih od A2.
3. Spoj prema zahtjevu 1 ili zahtjevu 2, naznačen time da aromatske skupine koje su definirane s R1 i/ili R3 su supstituirane.
4. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da su R1 i/ili R3 supstituirani s jednim ili dva supstituenta smještena na para i/ili meta položaju.
5. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da A1, A2, A3 i A4 neovisno predstavljaju Q1 ili mogu alternativno predstavljati C1-6 alkil ili heterocikloalkil, od kojih su oba proizvoljno supstituirana s jednim ili više Q2 supstituenata; svaki Q1, Q2 i Q3 neovisno predstavlja C1-6 alkil (proizvoljno supstituiran s jednim ili više fluoro atoma), 5- ili 6-članu heterocikloalkil skupinu (proizvoljno supstituiranu s jednim ili više supstituenata odabranih od E1), -SR10a, -S(O)R10a, -NR12aS(O)2R10a, -C(=Y)-N(R10a)R11a, -S(O)2N(R10a)R11a, -N(R12a)C(=Y)R11a, halo, -CN, -OR10a, -N(R10a)R11a, -C(=Y)OR10a ili -S(O)2R10a; svaki R10a, R11a i R12a neovisno predstavlja vodik, C1-3 alkil ili heterocikloalkil, navedene dvije posljednje skupine su proizvoljno supstituirane s jednim ili više supstituenata izabranih od E3; ili R10a može predstavljati aril ili heteroaril; ili R10a i R11a mogu biti povezani zajedno tako da tvore 5- ili 6-člani prsten koji proizvoljno sadrži jedan dodatni heteroatom (navedeni prsten može biti supstituiran s jednim ili više E5 supstituenata); R12a predstavlja C1-3 alkil ili vodik; svaki E1, E2, E3, E4 i E5 neovisno predstavlja C1-6 alkil, heterocikloalkil (navedene dvije posljednje skupine su proizvoljno supstituirane s jednim ili više supstituenata izabranih od =O i Q5) ili Q4; svaki Q4, Q5 i Q1 neovisno predstavljaju halo, -C(=Y)-OR20, -N(R20)R21, - C(=Y)N(R20)R21 ili -N(R22)C(=Y)OR21; svaki Y neovisno predstavlja =O; R20 i R21 neovisno predstavljaju vodik ili C1-4 alkil; ili R20 i R21, kada su spojeni na isti atom dušika su zajedno vezani tako da tvore 5- ili 6-člani prsten, koji proizvoljno sadrži dodatni heteroatom; i/ili R22 predstavlja vodik.
6. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da je spoj s formulom I odabran iz skupine koja sadrži:
2-(3,4-Dimetoksi-fenil)-5-(3-fluoro-4-metansulfonil-fenil)-6-metil-imidazo[2,1-b][1,3,4]tiadiazol;
5-[2-(3,4-Dimetoksi-fenil)-6-metil-imidazo[2,1-b][1,3,4]tiadiazol-5-il]-piridin-2-karbonitril;
5-[2-(3,4-Dimetoksi-fenil)-6-metil-imidazo[2,1-b][1,3,4]tiadiazol-5-il]-3-trifluorometil-piridin-2-ilamin;
2-(3,4-Dimetoksi-fenil)-6-metil-5-piridin-3-il-imidazo[2,1-b][1,3,4]tiadiazol;
2-(3,4-Dimetoksi-fenil)-5-(6-metoksi-piridin-3-il)-6-metil-imidazo[2,1-b][1,3,4]tiadiazol;
2,5-Bis-(3,4-dimetoksi-fenil)-6-metil-imidazo[2,1-b][1,3,4]tiadiazol;
5-[2-(3,4-Dimetoksi-fenil)-6-metil-imidazo[2,1-b][1,3,4]tiadiazol-5-il]-pirimidin-2-ilamin;
5-[2-(3,4-Dimetoksi-fenil)-6-metil-imidazo[2,1-b][1,3,4]tiadiazol-5-il]-piridin-2-ol;
tert-Butil 2-(4-(5-(6-amino-5-(trifluorometil)piridin-3-il)-6-metilimidazo-[2,1-b][1,3,4]tiadiazol-2-il)-2-metoksifenoksi)etilkarbamat;
2-(4-(5-(6-amino-5-(trifluorometil)piridin-3-il)-6-metilimidazo[2,1-b][1,3,4]tiadiazol-2-il)-2-metoksifenoksi)-N,N-dimetilacetamid;
5-(2-(4-(2-morfolinoetoksi)-3-metoksifenil)-6-metilimidazo[2,1-b][1,3,4]tiadiazol-5-il)-3-(trifluorometil)piridin-2-amin;
5-{2-[3-Metoksi-4-(piperidin-4-iloksi)-fenil]-imidazo[2,1-b][1,3,4]tiadiazol-5-il}-3-trifluorometil-piridin-2-ilamin;
2-[3-Metoksi-4-(piperidin-4-iloksi)-fenil]-5-(6-metoksi-piridin-3-il)-imidazo[2,1-b][1,3,4]tiadiazol;
tert-butil ester 4-{4-[5-(2-Amino-pirimidin-5-il)-imidazo[2,1-b][1,3,4]tiadiazol-2-il]-2-metoksi-fenoksi}-piperidin-1-karboksilne kiseline;
5-{2-[3-Metoksi-4-(piperidin-4-iloksi)-fenil]-imidazo[2,1-b][1,3,4]tiadiazol-5-il}-pirimidin-2-ilamin;
2,5-Bis-(3,4-dimetoksi-fenil)-imidazo[2,1-b][1,3,4]tiadiazol;
5-[2-(3,4-Dimetoksi-fenil)-imidazo[2,1-b][1,3,4]tiadiazol-5-il]-piridin-2-karbonitril;
tert-butil ester 4-{5-[2-(3,4-Dimetoksi-fenil)-imidazo[2,1-b][1,3,4]tiadiazol-5-il]-pirimidin-2-il}-piperazin-1-karboksilne kiseline;
2-(3,4-Dimetoksi-fenil)-5-(2-piperazin-1-il-pirimidin-5-il)-imidazo[2,1-b][1,3,4]tiadiazol;
2-(3,4-Dimetoksi-fenil)-5-[2-(4-metil-piperazin-1-il)-pirimidin-5-il]-imidazo[2,1-b][1,3,4]tiadiazol;
2-(3,4-Dimetoksi-fenil)-5-(6-piperazin-1-il-5-trifluorometil-piridin-3-il)-imidazo[2,1-b][1,3,4]tiadiazol;
2-(3,4-Dimetoksi-fenil)-5-[6-(4-metil-piperazin-1-il)-5-trifluorometil-piridin-3-il]-imidazo[2,1-b][1,3,4]tiadiazol;
2-(3,4-Dimetoksi-fenil)-5-(2-metilsulfanil-pirimidin-5-il)-imidazo[2,1-b][1, 3,4]tiadiazol;
2-(3,4-Dimetoksi-fenil)-5-(2-metansulfinil-pirimidin-5-il)-imidazo[2,1-b][1,3,4]tiadiazol;
2-(3,4-dimetoksifenil)-5-(5-metoksipiridin-3-il)imidazo[2,1-b][1,3,4]tiadiazol;
N-{3-[5-(6-Amino-5-trifluorometil-piridin-3-il)-imidazo[2,1-b][1,3,4]tiadiazol-2-il]-fenil}-metansulfonamid;
N-{3-[5-(6-Amino-5-trifluorometil-piridin-3-il)-imidazo[2,1-b][1,3,4]tiadiazol-2-il]-benzil}-metansulfonamid;
5-[2-(1'-(tert-butoksikarbonil)-2-okso-1,2-dihidrospiro[indol-3,4'-piperidin]-5-il)-imidazo[2,1-b][1,3,4]tiadiazol-5-il]-3-trifluorometil-piridin-2-ilamin;
5-[2-(2-okso-1,2-dihidrospiro[indol-3,4'-piperidin]-5-il)-imidazo[2,1-b][1,3,4]tiadiazol-5-il]-3-trifluorometil-piridin-2-ilamin;
5-{2-[4-(morfolin-4-sulfonil)-fenil]-imidazo[2,1-b][1,3,4]tiadiazol-5-il}-3-trifluorometil-piridin-2-ilamin;
5-{2-[3-(Morfolin-4-sulfonil)-fenil]-imidazo[2,1-b][1,3,4]tiadiazol-5-il}-3-trifluorometil-piridin-2-ilamin;
2,4-Difluoro-N-[2-metoksi-5-(5-piridazin-4-il-imidazo[2,1-b][1,3,4]tiadiazol-2-il)-piridin-3-il]-benzensulfonamid;
5-[5-(4-Metansulfonil-fenil)-imidazo[2,1-b][1,3,4]tiadiazol-2-il]-3-trifluorometil-piridin-2-ilamin;
5-[5-(6-Fluoro-piridin-3-il)-imidazo[2,1-b][1,3,4]tiadiazol-2-il]-3-trifluorometil-piridin-2-ilamin; i
metil ester 4-[2-(6-Amino-5-trifluorometil-piridin-3-il)-imidazo[2,1-b][1,3,4]tiadiazol-5-il]-2-metoksi-benzojeve kiseline.
7. Spoj s formulom I, ili farmaceutski prihvatljiv ester, amid, solvat ili njihova sol, kao što je definirano u bilo kojem od zahtjeva 1 do 6 naznačen time da je za uporabu kao lijek.
8. Farmaceutska formulacija naznačena time da sadrži spoj s formulom I, ili farmaceutski prihvatljiv ester, amid, solvat ili njihova sol, kao što je definirano u bilo kojem od zahtjeva 1 do 6 u smjesi s farmaceutski prihvatljivim pomoćnim sredstvom, razrjeđivačem ili nosačem.
9. Spoj, ili farmaceutski prihvatljiv ester, amid, solvat ili njihova sol, kao što je definirano u bilo kojem od zahtjeva 1 do 6 ali bez uvjeta, naznačena time da je za uporabu za liječenje bolesti, pri čemu je bolest odabrana iz skupine koju čine rak, imunološki poremećaj, kardiovaskularna bolest, virusna infekcija, upala, poremećaj metabolizma/endokrine funkcije, neurološki poremećaj, opstruktivna bolest dišnih puteva, alergijska bolest, upalna bolest, imunosupresivni poremećaj, poremećaj obično povezan s presađivanjem organa, bolest povezana s AIDS-om, benigna hiperplazija prostate, obiteljska adenomatoza, polipoza, neurofibromatoza, psorijaza, koštani poremećaj, ateroskleroza, proliferacija glatkih vaskularnih stanica povezana s aterosklerozom, plućna fibroza, artritis glomerulonefritis i post-operativna stenoza, restenoza, udar, dijabetes, hepatomegalija, Alzheimerova bolest, cistična fibroza, bolest vezana uz hormone, poremećaj imunodeficijencije, destruktivni poremećaj kostiju, zarazna bolest, stanje povezano s odumiranjem stanica, trombinom izazvana agregacija pločica, kronična mijelogena leukemija, bolest jetre, patološko imunološko stanje koje uključuje aktivaciju T stanica, poremećaji CNS, te druge povezane bolesti.
10. Uporaba spoja s formulom I, ili farmaceutski prihvatljivog estera, amida, solvata ili njihove soli, kao što je definirano u bilo kojem od zahtjeva 1 do 6 ali bez uvjeta, naznačena time da je za proizvodnju lijeka za liječenje bolesti, pri čemu je bolest odabrana iz skupine koju čine rak, imunološki poremećaj, kardiovaskularna bolest, virusna infekcija, upala, poremećaj metabolizma/endokrine funkcije, neurološki poremećaj, opstruktivna bolest dišnih puteva, alergijska bolest, upalna bolest, imunosupresivni poremećaj, poremećaj obično povezan s presađivanjem organa, bolest povezana s AIDS-om, benigna hiperplazija prostate, obiteljska adenomatoza, polipoza, neurofibromatoza, psorijaza, koštani poremećaj, ateroskleroza, proliferacija glatkih vaskularnih stanica povezana s aterosklerozom, plućna fibroza, artritis glomerulonefritis i post-operativna stenoza, restenoza, udar, dijabetes, hepatomegalija, Alzheimerova bolest, cistična fibroza, bolest vezana uz hormone, poremećaj imunodeficijencije, destruktivni poremećaj kostiju, zarazna bolest, stanje povezano s odumiranjem stanica, trombinom izazvana agregacija pločica, kronična mijelogena leukemija, bolest jetre, patološko imunološko stanje koje uključuje aktivaciju T stanica, poremećaji CNS, te druge povezane bolesti.
11. Kombinirani proizvod naznačen time da sadrži:
(A) spoj s formulom I, ili farmaceutski prihvatljiv ester, amid, solvat ili njegovu sol, kao što je definirano u bilo kojem od zahtjeva 1 do 6 ali bez uvjeta; i
(B) drugo terapijsko sredstvo koje je korisno u liječenju raka i/ili proliferativne bolesti,
pri čemu je svaka od komponenata (A) i (B) formulirana u smjesi s farmaceutski prihvatljivim pomoćnim sredstvom, razrjeđivačem ili nosačem.
12. Postupak za pripremanje spoja s formulom I kao što je definirano u zahtjevu 1, naznačen time da postupak sadrži:
(i) reakciju odgovarajućeg spoja formule II,
[image]
pri čemu L1 predstavlja prikladnu izlaznu skupinu, i R1 i R2 su kao što je definirano u zahtjevu 1, sa spojem s formulom III,
L2-R3 III
pri čemu L2 predstavlja prikladnu izlaznu skupinu, i R3 je kao što je definirano u zahtjevu 1;
(ii) reakciju spoja s formulom IV,
[image]
pri čemu L3 predstavlja prikladnu izlaznu skupinu, i R2 i R3 su kao što je definirano u zahtjevu 1, sa spojem s formulom V,
R1-L4 V
pri čemu L4 predstavlja prikladnu izlaznu skupinu;
(iii) za spojeve s formulom I u kojoj, kako je prikladno, postoji prisutan supstituent Q1 do Q6, u kojoj takve skupine predstavljaju -OR10a ili -OR20, u kojoj R10a i R20 ne predstavljaju vodik, reakciju odgovarajućeg spoja formule I u kojoj postoji prisutan Q1 do Q6, koji predstavlja -OR10a i -OR20 (kako je prikladno), u kojoj R10a i R20 do predstavljaju vodik, sa spojem s formulom VI,
Rx-L5 VI
pri čemu L5 predstavlja prikladnu izlaznu skupinu i Rx predstavlja R10a ili R20 (kako je prikladno), pod uvjetom da ne predstavljaju vodik.
13. Postupak za pripremanje farmaceutske formulacije kao što je definirano u zahtjevu 8, naznačen time da postupak sadrži dovođenje u doticaj spoja s formulom I, ili farmaceutski prihvatljivog estera, amida, solvata ili njihove soli, kao što je definirano u bilo kojem od zahtjeva 1 do 6, s farmaceutski prihvatljivim pomoćnim sredstvom, razrjeđivačem ili nosačem.
14. Postupak za pripremanje kombiniranog proizvoda kao što je definirano u zahtjevu 11, naznačen time da postupak sadrži dovođenje u doticaj spoja s formulom I, ili farmaceutski prihvatljivog estera, amida, solvata ili njihove soli, kao što je definirano u bilo kojem od zahtjeva 1 do 6 ali bez uvjeta, s drugim terapijskim sredstvom koje je korisno u liječenju raka i/ili proliferativne bolesti, te najmanje jednim farmaceutski prihvatljivim pomoćnim sredstvom, razrjeđivačem ili nosačem.
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| PCT/GB2010/000674 WO2010112874A1 (en) | 2009-04-02 | 2010-04-01 | Imidazo [2, 1-b] [ 1, 3, 4 ] thiadiazole derivatives |
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Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0821913D0 (en) | 2008-12-02 | 2009-01-07 | Price & Co | Antibacterial compounds |
| WO2011121317A1 (en) | 2010-04-01 | 2011-10-06 | Centro Nacional De Investigaciones Oncologicas (Cnio) | Imidazo [2,1-b] [1,3,4] thiadiazoles as protein or lipid kinase inhibitors |
| AU2011260097B2 (en) | 2010-06-01 | 2015-01-22 | Summit (Oxford) Limited | Compounds for the treatment of clostridium difficile associated disease |
| GB2480815A (en) * | 2010-06-01 | 2011-12-07 | Summit Corp Plc | Compounds for the treatment of clostridium difficile-associated disease |
| WO2012020215A1 (en) | 2010-08-09 | 2012-02-16 | Centro Nacional De Investigaciones Oncológicas (Cnio) | Amino- imidazolothiadiazoles for use as protein or lipid kinase inhibitors |
| WO2012020217A1 (en) | 2010-08-09 | 2012-02-16 | Centro Nacional De Investigaciones Oncológicas (Cnio) | Amino- imidazolothiadiazoles for use as protein or lipid kinase inhibitors |
| EA022623B1 (ru) | 2010-10-06 | 2016-02-29 | ГЛАКСОСМИТКЛАЙН ЭлЭлСи | Производные бензимидазола в качестве ингибиторов pi3-киназ |
| TWI617559B (zh) | 2010-12-22 | 2018-03-11 | 江蘇恆瑞醫藥股份有限公司 | ２－芳基咪唑并［１，２－ｂ］嗒．２－苯基咪唑并［１，２－ａ］吡啶，和２－苯基咪唑并［１，２－ａ］吡衍生物 |
| PT2710018T (pt) | 2011-05-19 | 2022-03-01 | Fundacion Del Sector Publico Estatal Centro Nac De Investigaciones Oncologicas Carlos Iii F S P Cnio | Compostos macrocíclicos como inibidores de proteína quinases |
| KR101399484B1 (ko) | 2011-07-14 | 2014-05-29 | 한국화학연구원 | 허피스바이러스 엑소뉴클리에이즈 활성 억제 물질을 유효성분으로 함유하는 항허피스바이러스용 약학적 조성물 |
| KR20170047341A (ko) | 2014-08-29 | 2017-05-04 | 씨에이치디아이 파운데이션, 인코포레이티드 | 헌팅틴 단백질을 영상화하기 위한 프로브 |
| MX2017002703A (es) | 2014-08-29 | 2018-01-16 | Chdi Foundation Inc | Sondas para la proyección de imagen de la proteína huntingtina. |
| TWI811428B (zh) * | 2018-08-21 | 2023-08-11 | 日商杏林製藥股份有限公司 | 雙環雜芳香環衍生物 |
| CA3113233A1 (en) | 2018-09-18 | 2020-03-26 | Nikang Therapeutics, Inc. | Fused tricyclic ring derivatives as src homology-2 phosphatase inhibitors |
| BR112022007404A2 (pt) | 2019-10-21 | 2022-07-05 | Novartis Ag | Compostos e composições para o tratamento de doenças parasíticas |
| EP4210697A1 (en) * | 2020-09-14 | 2023-07-19 | The University of Sussex | Small molecule inhibitors of lemur tyrosine kinase 3 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1464259A (en) | 1975-10-03 | 1977-02-09 | Pfizer Ltd | Imidazo-thiazole and -thiadiazole sulphonamides and their use as therapeutic agents |
| NO811630L (no) | 1980-05-29 | 1981-11-30 | Bayer Ag | Imidazoazolalkensyreamider, nye mellomprodukter for deres fremstilling, deres fremstilling og deres anvendelse som legemiddel |
| DE3208437A1 (de) | 1982-03-09 | 1983-09-15 | Bayer Ag, 5090 Leverkusen | Imidazothiadiazolalkencarbonsaeureamide, neue zwischenprodukte zu ihrer herstellung, ihre herstellung und ihre verwendung in arzneimitteln |
| IT1269176B (it) | 1994-01-11 | 1997-03-21 | Isagro Srl | Eterobicicli ad attivita' fungicida |
| WO1997011075A1 (en) | 1995-09-22 | 1997-03-27 | Takeda Chemical Industries, Ltd. | Triazole compounds, their production and use |
| CA2411928A1 (en) * | 2000-08-09 | 2002-02-14 | Agouron Pharmaceuticals, Inc. | Pyrazole-thiazole compounds, pharmaceutical compositions containing them, and methods of their use for inhibiting cyclindependent kinases |
| CA2364985A1 (en) * | 2001-12-14 | 2003-06-14 | John W. Gillard | Imidazo(2,1-b)thiadiazole sulfonamides |
| MXPA05006478A (es) | 2002-12-18 | 2005-09-08 | Vertex Pharma | Triazolopiridazinas como inhibidores de proteinas cinasas. |
| PA8595001A1 (es) | 2003-03-04 | 2004-09-28 | Pfizer Prod Inc | Nuevos compuestos heteroaromaticos condensados que son inhibidores del factor de crecimiento transforante (tgf) |
| EP1636242A1 (en) | 2003-06-13 | 2006-03-22 | Aegera Therapeutics Inc. | Acylated imidazo (2,1-b) -1,3,4,-thiadia zole-2-sulfonamides, and uses thereof |
| CA2527903A1 (en) * | 2003-06-13 | 2004-12-23 | Aegera Therapeutics, Inc. | Imidazo[2,1-b]-1,3,4-thiadiazole sulfoxides and sulfones |
| SE0402735D0 (sv) | 2004-11-09 | 2004-11-09 | Astrazeneca Ab | Novel compounds |
| CA2610695A1 (en) | 2005-06-01 | 2006-12-07 | Ucb Pharma, S.A. | 2-oxo-1-pyrrolidine derivatives and their therapeutic use on the central nervous system |
| US20070049591A1 (en) | 2005-08-25 | 2007-03-01 | Kalypsys, Inc. | Inhibitors of MAPK/Erk Kinase |
| US7750000B2 (en) | 2005-09-02 | 2010-07-06 | Bayer Schering Pharma Ag | Substituted imidazo[1,2b]pyridazines as kinase inhibitors, their preparation and use as medicaments |
| NZ568666A (en) | 2005-11-30 | 2011-09-30 | Vertex Pharma | [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazole derivative as inhibitors of c-Met |
| KR20090033833A (ko) | 2006-04-13 | 2009-04-06 | 에게라 쎄라퓨틱스 인코포레이티드 | 신경병증성 통증의 치료를 위한 이미다조［2，1―ｂ］―1，3，4―티아디아졸―2―술폰아미드 화합물의 이용 |
| WO2007129044A1 (en) | 2006-05-03 | 2007-11-15 | Astrazeneca Ab | Thiazole derivatives and their use as anti-tumour agents |
| WO2007136736A2 (en) | 2006-05-19 | 2007-11-29 | Codon Devices, Inc. | Methods for nucleic acid sorting and synthesis |
| EP2029593A1 (en) | 2006-05-22 | 2009-03-04 | AstraZeneca AB | Indole derivatives |
| ES2549862T3 (es) | 2006-08-30 | 2015-11-02 | Cellzome Limited | Derivados de triazol como inhibidores de quinasa |
| CN101594909A (zh) * | 2006-09-07 | 2009-12-02 | 比奥根艾迪克Ma公司 | 用于治疗炎性病症、细胞增殖性失调、免疫失调的irak调节剂 |
| WO2008060578A2 (en) | 2006-11-15 | 2008-05-22 | Cytovia, Inc. | 3-aryl-6-aryl-[1,2,4] triazolo[3,4-b][1,3,4] thiadiazoles and related compounds as activators of caspases and inducers of apoptosis and the use thereof |
| CN101037445A (zh) | 2007-04-14 | 2007-09-19 | 西北师范大学 | 一种具有潜在生物活性的咪唑并[2，1－b]－1，3，4－噻二唑衍生物及其合成方法 |
| MX2009012066A (es) | 2007-05-09 | 2009-11-19 | Novartis Ag | Imidazopirinas sustituidas como inhibidoras de cinasa de lipido p13k. |
| PE20090717A1 (es) | 2007-05-18 | 2009-07-18 | Smithkline Beecham Corp | Derivados de quinolina como inhibidores de la pi3 quinasa |
| JP2010528991A (ja) | 2007-05-21 | 2010-08-26 | エスジーエックス ファーマシューティカルズ、インコーポレイテッド | 複素環式キナーゼ調節因子 |
| WO2009019708A2 (en) * | 2007-08-09 | 2009-02-12 | Urifer Ltd | Pharmaceutical compositions and methods for the treatment of cancer |
| HUE025976T2 (en) * | 2007-09-27 | 2016-05-30 | Fund Centro Nac De Investig Oncologicas Carlos Iii | Imidazolothiadiazoles for use as protein kinase inhibitors |
| EP2211615A4 (en) | 2007-10-22 | 2010-10-13 | Glaxosmithkline Llc | PYRIDOSULFONAMIDE DERIVATIVES AS PI3 KINASE INHIBITORS |
| JP2011529456A (ja) | 2008-07-29 | 2011-12-08 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | イミダゾチアジアゾール誘導体 |
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2010
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- 2010-04-01 ES ES10715318.1T patent/ES2548571T3/es active Active
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- 2010-04-01 SI SI201031054T patent/SI2414369T1/sl unknown
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