AU2005282753A1 - Chemical compounds - Google Patents
Chemical compounds Download PDFInfo
- Publication number
- AU2005282753A1 AU2005282753A1 AU2005282753A AU2005282753A AU2005282753A1 AU 2005282753 A1 AU2005282753 A1 AU 2005282753A1 AU 2005282753 A AU2005282753 A AU 2005282753A AU 2005282753 A AU2005282753 A AU 2005282753A AU 2005282753 A1 AU2005282753 A1 AU 2005282753A1
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- imidazo
- tetrahydro
- pyridin
- 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 description 275
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 248
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 179
- 125000000217 alkyl group Chemical group 0.000 claims description 157
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 108
- -1 -Racycloalkyl Chemical group 0.000 claims description 84
- 125000003342 alkenyl group Chemical group 0.000 claims description 75
- 125000000304 alkynyl group Chemical group 0.000 claims description 75
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 71
- 238000006268 reductive amination reaction Methods 0.000 claims description 69
- 125000001188 haloalkyl group Chemical group 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 43
- 238000011282 treatment Methods 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 41
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 39
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 39
- 239000003795 chemical substances by application Substances 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 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 33
- 230000000694 effects Effects 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims description 26
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 208000031886 HIV Infections Diseases 0.000 claims description 19
- 208000037357 HIV infectious disease Diseases 0.000 claims description 19
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 125000004043 oxo group Chemical group O=* 0.000 claims description 19
- 238000005859 coupling reaction Methods 0.000 claims description 17
- 235000019441 ethanol Nutrition 0.000 claims description 17
- 238000011321 prophylaxis Methods 0.000 claims description 17
- 102000009410 Chemokine receptor Human genes 0.000 claims description 16
- 108050000299 Chemokine receptor Proteins 0.000 claims description 16
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
- 201000004624 Dermatitis Diseases 0.000 claims description 15
- 208000029523 Interstitial Lung disease Diseases 0.000 claims description 15
- 208000026935 allergic disease Diseases 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 229960004756 ethanol Drugs 0.000 claims description 15
- 230000009610 hypersensitivity Effects 0.000 claims description 15
- 230000002757 inflammatory effect Effects 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- 201000004681 Psoriasis Diseases 0.000 claims description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 14
- 230000002708 enhancing effect Effects 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 14
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 13
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 13
- 206010061218 Inflammation Diseases 0.000 claims description 13
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 150000001412 amines Chemical group 0.000 claims description 13
- 230000008878 coupling Effects 0.000 claims description 13
- 238000010168 coupling process Methods 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 201000000596 systemic lupus erythematosus Diseases 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
- 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
- 125000006552 (C3-C8) cycloalkyl group Chemical group 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
- 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
- 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 8
- 206010020751 Hypersensitivity Diseases 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 8
- 208000010668 atopic eczema Diseases 0.000 claims description 8
- 208000032839 leukemia Diseases 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
- 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
- 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
- 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
- 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
- 206010039710 Scleroderma 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
- 208000025865 Ulcer Diseases 0.000 claims description 7
- 208000024780 Urticaria Diseases 0.000 claims description 7
- 206010047115 Vasculitis Diseases 0.000 claims description 7
- 201000010105 allergic rhinitis Diseases 0.000 claims description 7
- 208000003455 anaphylaxis Diseases 0.000 claims description 7
- 201000008937 atopic dermatitis Diseases 0.000 claims description 7
- 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
- 201000001981 dermatomyositis Diseases 0.000 claims description 7
- 230000002327 eosinophilic effect Effects 0.000 claims description 7
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 claims description 7
- 208000024908 graft versus host disease Diseases 0.000 claims description 7
- 230000011132 hemopoiesis Effects 0.000 claims description 7
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 claims description 7
- 201000006362 hypersensitivity vasculitis Diseases 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 7
- 210000004072 lung Anatomy 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 230000002956 necrotizing effect Effects 0.000 claims description 7
- 125000003729 nucleotide group Chemical group 0.000 claims description 7
- 208000005987 polymyositis Diseases 0.000 claims description 7
- 208000017520 skin disease Diseases 0.000 claims description 7
- 201000005671 spondyloarthropathy Diseases 0.000 claims description 7
- 230000029663 wound healing Effects 0.000 claims description 7
- 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 6
- 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 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 206010012442 Dermatitis contact Diseases 0.000 claims description 6
- 208000019693 Lung disease Diseases 0.000 claims description 6
- 206010053613 Type IV hypersensitivity reaction 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
- 208000002029 allergic contact dermatitis Diseases 0.000 claims description 6
- 210000004556 brain Anatomy 0.000 claims description 6
- 210000000481 breast Anatomy 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 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
- 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
- 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 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
- 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 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 230000005951 type IV hypersensitivity Effects 0.000 claims description 6
- 208000027930 type IV hypersensitivity disease Diseases 0.000 claims description 6
- 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 5
- 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 5
- 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 5
- 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 5
- 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 5
- UOFZOCCQDPJRLD-PKTZIBPZSA-N (8s)-n-[[5-[(3r)-3-(dimethylamino)pyrrolidin-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=2N1CC[C@@H](N(C)C)C1 UOFZOCCQDPJRLD-PKTZIBPZSA-N 0.000 claims description 5
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 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 5
- 239000000126 substance Substances 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 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 4
- LXPJSHZFBKHPQH-PKTZIBPZSA-N (8s)-n-[[5-[(3r)-3-(diethylamino)pyrrolidin-1-yl]imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1[C@H](N(CC)CC)CCN1C1=CC=CC2=NC(CN(C)[C@@H]3C4=NC=CC=C4CCC3)=CN12 LXPJSHZFBKHPQH-PKTZIBPZSA-N 0.000 claims description 4
- 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 4
- 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 4
- 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 4
- 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 4
- 229940044613 1-propanol Drugs 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- JPVKWRVSRZEMDF-UHFFFAOYSA-N n,n,n'-trimethyl-n'-[2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]imidazo[1,2-a]pyridin-5-yl]ethane-1,2-diamine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=CN2C(N(C)CCN(C)C)=CC=CC2=N1 JPVKWRVSRZEMDF-UHFFFAOYSA-N 0.000 claims description 4
- BABAEMPTYIHDCU-UHFFFAOYSA-N n-[[5-[4-[(dimethylamino)methyl]phenyl]imidazo[1,2-a]pyridin-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC(CN(C)C)=CC=C1C1=CC=CC2=NC(CN(C)C3C4=NC=CC=C4CCC3)=CN12 BABAEMPTYIHDCU-UHFFFAOYSA-N 0.000 claims description 4
- 239000012038 nucleophile Substances 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
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Landscapes
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| US60/610,765 | 2004-09-17 | ||
| PCT/US2005/031098 WO2006028896A2 (en) | 2004-09-02 | 2005-08-31 | Chemical compounds |
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| US20100280010A1 (en) * | 2006-01-25 | 2010-11-04 | Kristjan Gudmundsson | Chemical compounds |
| US8618122B2 (en) | 2006-05-16 | 2013-12-31 | Ono Pharmaceutical Co., Ltd. | Compound having acidic group which may be protected, and use thereof |
| EP2055705A4 (en) | 2006-07-31 | 2014-08-20 | Ono Pharmaceutical Co | COMPOUND WITH A CYCLIC GROUP BOUND BY A SPIRO BINDING THEREOF AND APPLY THEREOF |
| US7767826B2 (en) * | 2007-10-05 | 2010-08-03 | Pharmatech International, Inc. | Process for the synthesis of L-(+)-ergothioneine |
| EP2217069A4 (en) * | 2007-11-09 | 2012-03-14 | Salk Inst For Biological Studi | INHIBITORS OF NON-NUCLEOSIDE INHIBITORS OF THE REVERSE TRANSCRIPTASE |
| 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 |
| PT3105226T (pt) | 2014-02-13 | 2019-11-06 | Incyte Corp | Ciclopropilaminas como inibidores de lsd1 |
| ME03654B (me) | 2014-02-13 | 2020-07-20 | Incyte Corp | Ciklopropilamini kao lsd1 inhibitori |
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| AU2016243939B2 (en) * | 2015-04-03 | 2020-09-03 | Incyte Holdings Corporation | Heterocyclic compounds as LSD1 inhibitors |
| KR102710120B1 (ko) | 2015-08-12 | 2024-09-27 | 인사이트 홀딩스 코포레이션 | Lsd1 저해제의 염 |
| CA3008272A1 (en) | 2015-12-14 | 2017-06-22 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
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| WO2017106291A1 (en) * | 2015-12-15 | 2017-06-22 | Bristol-Myers Squibb Company | Cxcr4 receptor antagonists |
| EP3393468B1 (en) | 2015-12-22 | 2022-09-14 | X4 Pharmaceuticals, Inc. | Methods for treating immunodeficiency disease |
| JP2019510785A (ja) | 2016-04-08 | 2019-04-18 | エックス４ ファーマシューティカルズ， インコーポレイテッド | 癌を処置する方法 |
| CA3027498A1 (en) | 2016-06-21 | 2017-12-28 | X4 Pharmaceuticals, Inc. | Cxcr4 inhibitors and uses thereof |
| US10988465B2 (en) | 2016-06-21 | 2021-04-27 | X4 Pharmaceuticals, Inc. | CXCR4 inhibitors and uses thereof |
| WO2017223243A1 (en) * | 2016-06-21 | 2017-12-28 | X4 Pharmaceuticals, Inc. | Cxcr4 inhibitors and uses thereof |
| WO2018156595A1 (en) | 2017-02-21 | 2018-08-30 | Emory University | Chemokine cxcr4 receptor modulators and uses related thereto |
| US11396501B2 (en) * | 2017-09-25 | 2022-07-26 | Cgenetech (Suzhou, China) Co., Ltd. | Heteroaryl compounds as CXCR4 inhibitors, composition and method using the same |
| KR102678977B1 (ko) * | 2017-09-25 | 2024-06-28 | 씨젠테크 (쑤저우, 차이나) 컴퍼니 리미티드 | Cxcr4 저해제로서 헤테로아릴 화합물, 그 조성물 및 이용 방법 |
| US11649235B2 (en) | 2018-03-19 | 2023-05-16 | Emory University | Pan-tropic entry inhibitors |
| US10548889B1 (en) | 2018-08-31 | 2020-02-04 | X4 Pharmaceuticals, Inc. | Compositions of CXCR4 inhibitors and methods of preparation and use |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
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| EP1317445B1 (en) * | 2000-09-15 | 2009-03-11 | Anormed Inc. | Chemokine receptor binding heterocyclic compounds |
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- 2005-08-31 BR BRPI0514881-2A patent/BRPI0514881A/pt not_active IP Right Cessation
- 2005-08-31 JP JP2007530352A patent/JP2008511668A/ja active Pending
- 2005-08-31 MX MX2007002615A patent/MX2007002615A/es not_active Application Discontinuation
- 2005-09-01 AR ARP050103666A patent/AR051565A1/es not_active Application Discontinuation
- 2005-09-01 PE PE2005001008A patent/PE20060656A1/es not_active Application Discontinuation
- 2005-09-01 AR ARP050103665A patent/AR050302A1/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
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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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