CA2579059A1 - Chemical compounds - Google Patents
Chemical compounds Download PDFInfo
- Publication number
- CA2579059A1 CA2579059A1 CA002579059A CA2579059A CA2579059A1 CA 2579059 A1 CA2579059 A1 CA 2579059A1 CA 002579059 A CA002579059 A CA 002579059A CA 2579059 A CA2579059 A CA 2579059A CA 2579059 A1 CA2579059 A1 CA 2579059A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- tetrahydro
- pyridin
- imidazo
- quinolinamine
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 275
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims abstract description 27
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims abstract description 25
- 208000031886 HIV Infections Diseases 0.000 claims abstract description 20
- 208000037357 HIV infectious disease Diseases 0.000 claims abstract description 20
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims abstract description 20
- 102000009410 Chemokine receptor Human genes 0.000 claims abstract description 17
- 108050000299 Chemokine receptor Proteins 0.000 claims abstract description 17
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims abstract description 14
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 156
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 128
- 125000003342 alkenyl group Chemical group 0.000 claims description 75
- 125000000304 alkynyl group Chemical group 0.000 claims description 75
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
- 238000006268 reductive amination reaction Methods 0.000 claims description 71
- 125000001188 haloalkyl group Chemical group 0.000 claims description 67
- -1 stavidine Chemical compound 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 55
- 238000011282 treatment Methods 0.000 claims description 42
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 39
- 239000003795 chemical substances by application Substances 0.000 claims description 38
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical group 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
- 230000000694 effects Effects 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 19
- 125000004043 oxo group Chemical group O=* 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 238000011321 prophylaxis Methods 0.000 claims description 17
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
- 238000005859 coupling reaction Methods 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 208000029523 Interstitial Lung disease Diseases 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 230000002757 inflammatory effect Effects 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
- 201000004624 Dermatitis Diseases 0.000 claims description 14
- 201000004681 Psoriasis Diseases 0.000 claims description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 14
- 208000026935 allergic disease Diseases 0.000 claims description 14
- 230000002708 enhancing effect Effects 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 230000009610 hypersensitivity Effects 0.000 claims description 14
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 14
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- 206010061218 Inflammation Diseases 0.000 claims description 13
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 230000004054 inflammatory process Effects 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 210000001519 tissue Anatomy 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 150000001412 amines Chemical group 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 12
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- FRHRAPSVOIMXJY-FQEVSTJZSA-N (8s)-n-methyl-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 FRHRAPSVOIMXJY-FQEVSTJZSA-N 0.000 claims description 10
- 125000004450 alkenylene group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004419 alkynylene group Chemical group 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- RTYCIUZFGNBFDO-NRFANRHFSA-N (8s)-n-[[5-(4-ethylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(CC)CCN1C1=CC=CC2=NC(CN(C)[C@@H]3C4=NC=CC=C4CCC3)=CN12 RTYCIUZFGNBFDO-NRFANRHFSA-N 0.000 claims description 9
- PTROCZWZGUYFHN-QHCPKHFHSA-N (8s)-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-(2-methylpropyl)-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CC(C)CN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 PTROCZWZGUYFHN-QHCPKHFHSA-N 0.000 claims description 9
- VLKZZNVOWQCIBI-QFIPXVFZSA-N (8s)-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-propyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCCN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 VLKZZNVOWQCIBI-QFIPXVFZSA-N 0.000 claims description 9
- SGMXLHJXSIULNM-QHCPKHFHSA-N (8s)-n-butyl-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCCCN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 SGMXLHJXSIULNM-QHCPKHFHSA-N 0.000 claims description 9
- QDYGAGPVZXUDBW-NRFANRHFSA-N (8s)-n-ethyl-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 QDYGAGPVZXUDBW-NRFANRHFSA-N 0.000 claims description 9
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 9
- 150000003973 alkyl amines Chemical group 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- FRHRAPSVOIMXJY-UHFFFAOYSA-N n-methyl-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 FRHRAPSVOIMXJY-UHFFFAOYSA-N 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- ZNYNQVPNMSPERK-QHCPKHFHSA-N (8s)-n-(cyclopropylmethyl)-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(CC3CC3)[C@@H]3C4=NC=CC=C4CCC3)=CN12 ZNYNQVPNMSPERK-QHCPKHFHSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 8
- 208000032839 leukemia Diseases 0.000 claims description 8
- RTYCIUZFGNBFDO-UHFFFAOYSA-N n-[[5-(4-ethylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(CC)CCN1C1=CC=CC2=NC(CN(C)C3C4=NC=CC=C4CCC3)=CN12 RTYCIUZFGNBFDO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002773 nucleotide Substances 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- GRGVJGVHZOIZFP-FQEVSTJZSA-N (8s)-n-[[5-(4-aminopiperidin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N1CCC(N)CC1 GRGVJGVHZOIZFP-FQEVSTJZSA-N 0.000 claims description 7
- QJSUPMMHOXHUJT-QFIPXVFZSA-N (8s)-n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-propan-2-yl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CC(C)N([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 QJSUPMMHOXHUJT-QFIPXVFZSA-N 0.000 claims description 7
- LLTLSDYWBUFMNN-MJGOQNOKSA-N (8s)-n-[[5-[(3r)-3-aminopyrrolidin-1-yl]imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N1CC[C@@H](N)C1 LLTLSDYWBUFMNN-MJGOQNOKSA-N 0.000 claims description 7
- RAGLHMFSABSZAL-ZYZRXSCRSA-N (8s)-n-methyl-n-[1-[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]ethyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)C(C)C(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 RAGLHMFSABSZAL-ZYZRXSCRSA-N 0.000 claims description 7
- KGGOEFQJWNRJEG-LBAQZLPGSA-N (8s)-n-methyl-n-[[5-[methyl-(1-methylpyrrolidin-3-yl)amino]imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N(C)C1CCN(C)C1 KGGOEFQJWNRJEG-LBAQZLPGSA-N 0.000 claims description 7
- VVCKQGVIFYLFLK-QFIPXVFZSA-N 3-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]propan-1-ol Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(CCCO)[C@@H]3C4=NC=CC=C4CCC3)=CN12 VVCKQGVIFYLFLK-QFIPXVFZSA-N 0.000 claims description 7
- 206010058284 Allergy to arthropod sting Diseases 0.000 claims description 7
- 206010002198 Anaphylactic reaction Diseases 0.000 claims description 7
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 7
- 208000035143 Bacterial infection Diseases 0.000 claims description 7
- 208000011231 Crohn disease Diseases 0.000 claims description 7
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 7
- 206010012442 Dermatitis contact Diseases 0.000 claims description 7
- 206010013700 Drug hypersensitivity Diseases 0.000 claims description 7
- 206010014954 Eosinophilic fasciitis Diseases 0.000 claims description 7
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 7
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 7
- 206010020751 Hypersensitivity Diseases 0.000 claims description 7
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 7
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
- 208000034624 Leukocytoclastic Cutaneous Vasculitis Diseases 0.000 claims description 7
- 208000032514 Leukocytoclastic vasculitis Diseases 0.000 claims description 7
- 208000019693 Lung disease Diseases 0.000 claims description 7
- 241000288894 Myotis Species 0.000 claims description 7
- 206010035664 Pneumonia Diseases 0.000 claims description 7
- 206010035742 Pneumonitis Diseases 0.000 claims description 7
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 7
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 7
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 7
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 7
- 208000006045 Spondylarthropathies Diseases 0.000 claims description 7
- 201000009594 Systemic Scleroderma Diseases 0.000 claims description 7
- 206010042953 Systemic sclerosis Diseases 0.000 claims description 7
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 7
- 206010052779 Transplant rejections Diseases 0.000 claims description 7
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 7
- 206010053613 Type IV hypersensitivity reaction Diseases 0.000 claims description 7
- 208000025865 Ulcer Diseases 0.000 claims description 7
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- 206010047115 Vasculitis Diseases 0.000 claims description 7
- 208000002029 allergic contact dermatitis Diseases 0.000 claims description 7
- 201000010105 allergic rhinitis Diseases 0.000 claims description 7
- 208000003455 anaphylaxis Diseases 0.000 claims description 7
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- 230000001363 autoimmune Effects 0.000 claims description 7
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 7
- 238000010322 bone marrow transplantation Methods 0.000 claims description 7
- 238000002512 chemotherapy Methods 0.000 claims description 7
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- 230000002327 eosinophilic effect Effects 0.000 claims description 7
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- 230000011132 hemopoiesis Effects 0.000 claims description 7
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- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- AQOBWZRQYWFSAW-UHFFFAOYSA-N n-methyl-n-[(5-piperazin-1-ylimidazo[1,2-a]pyridin-2-yl)methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N=C1C=CC=2)=CN1C=2N1CCNCC1 AQOBWZRQYWFSAW-UHFFFAOYSA-N 0.000 claims description 7
- MFPNAWHIPSNSRA-UHFFFAOYSA-N n-methyl-n-[[5-(4-propan-2-ylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C(C)C)CCN1C1=CC=CC2=NC(CN(C)C3C4=NC=CC=C4CCC3)=CN12 MFPNAWHIPSNSRA-UHFFFAOYSA-N 0.000 claims description 7
- JPTZJWVMCKRUDC-UHFFFAOYSA-N n-propan-2-yl-n-[[5-(4-propan-2-ylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C(C)C)CC(N=C1C=CC=2)=CN1C=2N1CCN(C(C)C)CC1 JPTZJWVMCKRUDC-UHFFFAOYSA-N 0.000 claims description 7
- 230000002956 necrotizing effect Effects 0.000 claims description 7
- 125000003729 nucleotide group Chemical group 0.000 claims description 7
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- 208000027930 type IV hypersensitivity disease Diseases 0.000 claims description 7
- 230000029663 wound healing Effects 0.000 claims description 7
- XCBGMXUKNZCYDY-RPWUZVMVSA-N (8s)-n-(cyclopropylmethyl)-n-[[5-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1[C@H](N(C)C)CCN1C1=CC=CC2=NC(CN(CC3CC3)[C@@H]3C4=NC=CC=C4CCC3)=CN12 XCBGMXUKNZCYDY-RPWUZVMVSA-N 0.000 claims description 6
- DUXQJVSQUNTORQ-PKTZIBPZSA-N (8s)-n-[[5-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]imidazo[1,2-a]pyridin-2-yl]methyl]-n-propan-2-yl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CC(C)N([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N1CC[C@@H](N(C)C)C1 DUXQJVSQUNTORQ-PKTZIBPZSA-N 0.000 claims description 6
- VMDADMFTSYKUBK-NRFANRHFSA-N (8s)-n-methyl-n-[[5-(4-methyl-1,4-diazepan-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N1CCCN(C)CC1 VMDADMFTSYKUBK-NRFANRHFSA-N 0.000 claims description 6
- OLNFUKUUTXMWRQ-NRFANRHFSA-N 2-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]ethanol Chemical compound C1CN(C)CCN1C1=CC=CC2=NC(CN(CCO)[C@@H]3C4=NC=CC=C4CCC3)=CN12 OLNFUKUUTXMWRQ-NRFANRHFSA-N 0.000 claims description 6
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 6
- 206010039710 Scleroderma Diseases 0.000 claims description 6
- WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 claims description 6
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- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 210000004072 lung Anatomy 0.000 claims description 6
- GMZLORPERFPBOQ-UHFFFAOYSA-N n-[[5-(3,5-dimethylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1C(C)NC(C)CN1C1=CC=CC2=NC(CN(C)C3C4=NC=CC=C4CCC3)=CN12 GMZLORPERFPBOQ-UHFFFAOYSA-N 0.000 claims description 6
- XWVHXXMWDHKKAN-UHFFFAOYSA-N n-[[5-(3-aminoazetidin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(N=C1C=CC=2)=CN1C=2N1CC(N)C1 XWVHXXMWDHKKAN-UHFFFAOYSA-N 0.000 claims description 6
- QJSUPMMHOXHUJT-UHFFFAOYSA-N n-[[5-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-propan-2-yl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C(C)C)CC(N=C1C=CC=2)=CN1C=2N1CCN(C)CC1 QJSUPMMHOXHUJT-UHFFFAOYSA-N 0.000 claims description 6
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 6
- CKNAQFVBEHDJQV-UHFFFAOYSA-N oltipraz Chemical compound S1SC(=S)C(C)=C1C1=CN=CC=N1 CKNAQFVBEHDJQV-UHFFFAOYSA-N 0.000 claims description 6
- 229950008687 oltipraz Drugs 0.000 claims description 6
- 210000002307 prostate Anatomy 0.000 claims description 6
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- UNJUOXFDBJBZSL-FQEVSTJZSA-N (8s)-n-[[5-(1,4-diazepan-1-yl)imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N1CCCNCC1 UNJUOXFDBJBZSL-FQEVSTJZSA-N 0.000 claims description 5
- GBXJUSLOSBALMG-YADHBBJMSA-N (8s)-n-[[5-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]imidazo[1,2-a]pyridin-2-yl]methyl]-n-ethyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCN([C@@H]1C2=NC=CC=C2CCC1)CC(N=C1C=CC=2)=CN1C=2N1CC[C@@H](N(C)C)C1 GBXJUSLOSBALMG-YADHBBJMSA-N 0.000 claims description 5
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| JP5257068B2 (ja) | 2006-05-16 | 2013-08-07 | 小野薬品工業株式会社 | 保護されていてもよい酸性基を含有する化合物およびその用途 |
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| US7767826B2 (en) * | 2007-10-05 | 2010-08-03 | Pharmatech International, Inc. | Process for the synthesis of L-(+)-ergothioneine |
| WO2009061856A1 (en) * | 2007-11-09 | 2009-05-14 | The Salk Instituite For Biological Studies | Non-nucleoside reverse transcriptase inhibitors |
| CN102675305B (zh) * | 2011-03-08 | 2014-11-12 | 中国科学院上海药物研究所 | 一类咪唑并吡啶类化合物及其制备方法和用途 |
| CN103570683B (zh) * | 2012-07-30 | 2018-04-17 | 中国科学院上海药物研究所 | 多取代胺类化合物及其制备方法和用途 |
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| TWI720451B (zh) | 2014-02-13 | 2021-03-01 | 美商英塞特控股公司 | 作為lsd1抑制劑之環丙胺 |
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| SG11201708047UA (en) * | 2015-04-03 | 2017-10-30 | Incyte Corp | Heterocyclic compounds as lsd1 inhibitors |
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| WO2019060860A1 (en) * | 2017-09-25 | 2019-03-28 | Suzhou Yunxuan Yiyao Keji Youxian Gongsi | HETEROARYL COMPOUNDS AS INHIBITORS OF CXCR4, COMPOSITION AND METHOD OF USE THEREOF |
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|---|---|---|---|---|
| NZ225152A (en) * | 1987-07-17 | 1990-04-26 | Janssen Pharmaceutica Nv | Heterocyclically substituted piperidinyl benzamides as pharmaceuticals |
| JP2004512336A (ja) * | 2000-09-15 | 2004-04-22 | アノーメッド インコーポレイティド | ケモカインレセプター結合複素環式化合物 |
| DE60143457D1 (de) * | 2000-09-15 | 2010-12-23 | Anormed Inc | Chemokin Rezeptor bindende heterozyklische Verbindungen |
| IL154227A0 (en) * | 2000-09-15 | 2003-07-31 | Anormed Inc | Chemokine receptor binding heterocyclic compounds |
| NZ524421A (en) * | 2000-09-15 | 2005-02-25 | Anormed Inc | Chemokine receptor binding heterocyclic compounds |
| CN1596255A (zh) * | 2001-12-21 | 2005-03-16 | 阿诺麦德股份有限公司 | 具有强效的与趋化因子受体结合的杂环化合物 |
| US7291631B2 (en) * | 2003-04-11 | 2007-11-06 | Genzyme Corporation | CXCR4 chemokine receptor binding compounds |
| MX2007002679A (es) * | 2004-09-02 | 2007-05-16 | Smithkline Beecham Corp | Compuestos quimicos. |
| JP2008514622A (ja) * | 2004-09-24 | 2008-05-08 | スミスクライン ビーチャム コーポレーション | 化合物 |
| JP2009507795A (ja) * | 2005-08-31 | 2009-02-26 | スミスクライン ビーチャム コーポレーション | 化合物 |
-
2005
- 2005-08-28 MX MX2007002679A patent/MX2007002679A/es not_active Application Discontinuation
- 2005-08-28 JP JP2007530353A patent/JP2008511669A/ja active Pending
- 2005-08-28 WO PCT/US2005/031099 patent/WO2006026703A2/en not_active Ceased
- 2005-08-28 EP EP05815072A patent/EP1799671A4/en not_active Withdrawn
- 2005-08-31 RU RU2007106779/04A patent/RU2351592C2/ru not_active IP Right Cessation
- 2005-08-31 KR KR1020077007349A patent/KR20070049682A/ko not_active Withdrawn
- 2005-08-31 CA CA002578746A patent/CA2578746A1/en not_active Abandoned
- 2005-08-31 AU AU2005279835A patent/AU2005279835A1/en not_active Abandoned
- 2005-08-31 MX MX2007002615A patent/MX2007002615A/es not_active Application Discontinuation
- 2005-08-31 EP EP05794929A patent/EP1784185A4/en not_active Withdrawn
- 2005-08-31 US US11/574,586 patent/US20070254910A1/en not_active Abandoned
- 2005-08-31 JP JP2007530352A patent/JP2008511668A/ja active Pending
- 2005-08-31 BR BRPI0514881-2A patent/BRPI0514881A/pt not_active IP Right Cessation
- 2005-08-31 WO PCT/US2005/031098 patent/WO2006028896A2/en not_active Ceased
- 2005-08-31 CA CA002579059A patent/CA2579059A1/en not_active Abandoned
- 2005-08-31 US US11/574,583 patent/US20070232615A1/en not_active Abandoned
- 2005-08-31 KR KR1020077007549A patent/KR20070053313A/ko not_active Withdrawn
- 2005-08-31 AU AU2005282753A patent/AU2005282753A1/en not_active Abandoned
- 2005-08-31 RU RU2007106780/04A patent/RU2352567C2/ru not_active IP Right Cessation
- 2005-09-01 AR ARP050103666A patent/AR051565A1/es not_active Application Discontinuation
- 2005-09-01 AR ARP050103665A patent/AR050302A1/es not_active Application Discontinuation
- 2005-09-01 PE PE2005001008A patent/PE20060656A1/es not_active Application Discontinuation
- 2005-09-01 PE PE2005001007A patent/PE20060712A1/es not_active Application Discontinuation
- 2005-09-02 TW TW094130018A patent/TW200621754A/zh unknown
- 2005-09-02 TW TW094130013A patent/TW200612921A/zh unknown
-
2007
- 2007-02-19 IL IL181419A patent/IL181419A0/en unknown
- 2007-03-14 NO NO20071366A patent/NO20071366L/no not_active Application Discontinuation
- 2007-03-15 NO NO20071418A patent/NO20071418L/no not_active Application Discontinuation
- 2007-03-23 MA MA29772A patent/MA28872B1/fr unknown
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