AU2005277638A1 - Chemical compounds - Google Patents
Chemical compounds Download PDFInfo
- Publication number
- AU2005277638A1 AU2005277638A1 AU2005277638A AU2005277638A AU2005277638A1 AU 2005277638 A1 AU2005277638 A1 AU 2005277638A1 AU 2005277638 A AU2005277638 A AU 2005277638A AU 2005277638 A AU2005277638 A AU 2005277638A AU 2005277638 A1 AU2005277638 A1 AU 2005277638A1
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- tetrahydro
- benzimidazol
- piperazinyl
- 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 284
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 439
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 155
- 125000000217 alkyl group Chemical group 0.000 claims description 151
- -1 4-Amino-1 -piperidinyl Chemical group 0.000 claims description 117
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 101
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 95
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 77
- 125000003342 alkenyl group Chemical group 0.000 claims description 74
- 125000000304 alkynyl group Chemical group 0.000 claims description 74
- 150000001412 amines Chemical class 0.000 claims description 73
- 125000001188 haloalkyl group Chemical group 0.000 claims description 62
- 238000011282 treatment Methods 0.000 claims description 59
- 239000002253 acid Substances 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 40
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 39
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 35
- JQGOUNFVDYUKMM-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CN=C2C(N)CCCC2=C1 JQGOUNFVDYUKMM-UHFFFAOYSA-N 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical group 0.000 claims description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
- 150000003973 alkyl amines Chemical class 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 24
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims description 23
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 22
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
- 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
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 238000011321 prophylaxis Methods 0.000 claims description 17
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 16
- 238000006268 reductive amination reaction Methods 0.000 claims description 16
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 16
- JJDMKDXGNVJWCD-UHFFFAOYSA-N 1h-benzimidazole-4-carboxamide Chemical compound NC(=O)C1=CC=CC2=C1N=CN2 JJDMKDXGNVJWCD-UHFFFAOYSA-N 0.000 claims description 15
- 102000009410 Chemokine receptor Human genes 0.000 claims description 15
- 108050000299 Chemokine receptor Proteins 0.000 claims description 15
- 208000029523 Interstitial Lung disease Diseases 0.000 claims description 15
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 15
- 230000002757 inflammatory effect Effects 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- 201000004624 Dermatitis Diseases 0.000 claims description 14
- 201000004681 Psoriasis Diseases 0.000 claims description 14
- 125000004450 alkenylene group Chemical group 0.000 claims description 14
- 125000004419 alkynylene group Chemical group 0.000 claims description 14
- 208000026935 allergic disease Diseases 0.000 claims description 14
- 239000003814 drug Substances 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
- 206010061218 Inflammation Diseases 0.000 claims description 13
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 230000004054 inflammatory process Effects 0.000 claims description 13
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 13
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims description 12
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- JSBYJKOFWKQUFG-UHFFFAOYSA-N 2-benzyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound N1=C2C(N)CCCC2=CC=C1CC1=CC=CC=C1 JSBYJKOFWKQUFG-UHFFFAOYSA-N 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 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
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 208000032839 leukemia Diseases 0.000 claims description 8
- 210000001519 tissue Anatomy 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
- 208000011231 Crohn disease Diseases 0.000 claims description 7
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 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
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 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
- 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
- 208000024780 Urticaria Diseases 0.000 claims description 7
- 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
- 201000008937 atopic dermatitis Diseases 0.000 claims description 7
- 208000010668 atopic eczema Diseases 0.000 claims description 7
- 230000001363 autoimmune Effects 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
- 230000001404 mediated effect Effects 0.000 claims description 7
- 230000002956 necrotizing effect Effects 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 208000005987 polymyositis Diseases 0.000 claims description 7
- 208000017520 skin disease Diseases 0.000 claims description 7
- 230000005951 type IV hypersensitivity Effects 0.000 claims description 7
- 208000027930 type IV hypersensitivity disease Diseases 0.000 claims description 7
- 230000029663 wound healing Effects 0.000 claims description 7
- 208000006045 Spondylarthropathies 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
- 238000010322 bone marrow transplantation Methods 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
- 239000003937 drug carrier Substances 0.000 claims description 6
- 210000004072 lung Anatomy 0.000 claims description 6
- AIVVNDNIWAQWOH-UHFFFAOYSA-N n-methyl-n-[(4-piperazin-1-yl-1h-benzimidazol-2-yl)methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2N1CCNCC1 AIVVNDNIWAQWOH-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
- 239000002773 nucleotide Substances 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
- 201000005671 spondyloarthropathy Diseases 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- JKAGHWHIEIKQQE-HXUWFJFHSA-N (8r)-n-methyl-n-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@H]1C2=NC=CC=C2CCC1)CC(N(C1=2)C)=NC1=CC=CC=2N1CCN(C)CC1 JKAGHWHIEIKQQE-HXUWFJFHSA-N 0.000 claims description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- 229940044613 1-propanol Drugs 0.000 claims description 5
- QQRPHGDTDFELFZ-NRFANRHFSA-N 2-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]ethanol Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N(C)C(CN(CCO)[C@@H]1C3=NC=CC=C3CCC1)=N2 QQRPHGDTDFELFZ-NRFANRHFSA-N 0.000 claims description 5
- 208000035143 Bacterial infection Diseases 0.000 claims description 5
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 5
- RARYKEKXHDOFGV-UHFFFAOYSA-N n-methyl-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2N1CCN(C)CC1 RARYKEKXHDOFGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003729 nucleotide group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- WMXSCDKRBQLQHT-QFIPXVFZSA-N (8s)-n-ethyl-n-[[1-ethyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCN([C@@H]1C2=NC=CC=C2CCC1)CC(N(C1=2)CC)=NC1=CC=CC=2N1CCN(C)CC1 WMXSCDKRBQLQHT-QFIPXVFZSA-N 0.000 claims description 4
- WOUDZZACVGCCAB-NRFANRHFSA-N (8s)-n-ethyl-n-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCN([C@@H]1C2=NC=CC=C2CCC1)CC(N(C1=2)C)=NC1=CC=CC=2N1CCN(C)CC1 WOUDZZACVGCCAB-NRFANRHFSA-N 0.000 claims description 4
- UQUSGFGEARIPEG-IBGZPJMESA-N (8s)-n-methyl-n-[(1-methyl-7-piperazin-1-ylbenzimidazol-2-yl)methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N(C1=2)C)=NC1=CC=CC=2N1CCNCC1 UQUSGFGEARIPEG-IBGZPJMESA-N 0.000 claims description 4
- JKAGHWHIEIKQQE-FQEVSTJZSA-N (8s)-n-methyl-n-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC(N(C1=2)C)=NC1=CC=CC=2N1CCN(C)CC1 JKAGHWHIEIKQQE-FQEVSTJZSA-N 0.000 claims description 4
- FXPHCSJKYTUWQD-QFIPXVFZSA-N 3-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]propan-1-ol Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N(C)C(CN(CCCO)[C@@H]1C3=NC=CC=C3CCC1)=N2 FXPHCSJKYTUWQD-QFIPXVFZSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UOGDWUJAQURVRZ-UHFFFAOYSA-N n-(cyclopropylmethyl)-n-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CN(C)CCN1C1=CC=CC2=C1N(C)C(CN(CC1CC1)C1C3=NC=CC=C3CCC1)=N2 UOGDWUJAQURVRZ-UHFFFAOYSA-N 0.000 claims description 4
- HZYBDFKAVBAMFP-UHFFFAOYSA-N n-methyl-n-[[4-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound C1CCCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2N1CCN(C)CC1 HZYBDFKAVBAMFP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- JEHABMXQHSEKPF-NRFANRHFSA-N (8s)-n-[[1-ethyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=12N(CC)C(CN(C)[C@@H]3C4=NC=CC=C4CCC3)=NC2=CC=CC=1N1CCN(C)CC1 JEHABMXQHSEKPF-NRFANRHFSA-N 0.000 claims description 3
- PHRYNVIBEQXSSX-QFIPXVFZSA-N (8s)-n-[[1-methyl-7-(4-methylpiperazin-1-yl)benzimidazol-2-yl]methyl]-n-propyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCCN([C@@H]1C2=NC=CC=C2CCC1)CC(N(C1=2)C)=NC1=CC=CC=2N1CCN(C)CC1 PHRYNVIBEQXSSX-QFIPXVFZSA-N 0.000 claims description 3
- OKGPFTLYBPQBIX-CQSZACIVSA-N 1-[(2r)-4-benzoyl-2-methylpiperazin-1-yl]-2-(4-methoxy-1h-pyrrolo[2,3-b]pyridin-3-yl)ethane-1,2-dione Chemical compound C1=2C(OC)=CC=NC=2NC=C1C(=O)C(=O)N([C@@H](C1)C)CCN1C(=O)C1=CC=CC=C1 OKGPFTLYBPQBIX-CQSZACIVSA-N 0.000 claims description 3
- QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 claims description 3
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 claims description 3
- XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 claims description 3
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims description 3
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 claims description 3
- IBHARWXWOCPXCR-WELGVCPWSA-N [(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl (2-decoxy-3-dodecylsulfanylpropyl) hydrogen phosphate Chemical compound C1[C@H](N=[N+]=[N-])[C@@H](COP(O)(=O)OCC(CSCCCCCCCCCCCC)OCCCCCCCCCC)O[C@H]1N1C(=O)NC(=O)C(C)=C1 IBHARWXWOCPXCR-WELGVCPWSA-N 0.000 claims description 3
- UZYUJPSWCDMVEI-UHFFFAOYSA-N [2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]-1h-benzimidazol-4-yl]-piperazin-1-ylmethanone Chemical compound C1CCC2=CC=CN=C2C1N(C)CC(NC1=CC=C2)=NC1=C2C(=O)N1CCNCC1 UZYUJPSWCDMVEI-UHFFFAOYSA-N 0.000 claims description 3
- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 claims description 3
- 229960004748 abacavir Drugs 0.000 claims description 3
- 229960001997 adefovir Drugs 0.000 claims description 3
- 229960003205 adefovir dipivoxil Drugs 0.000 claims description 3
- 230000003064 anti-oxidating effect Effects 0.000 claims description 3
- 230000034303 cell budding Effects 0.000 claims description 3
- 229960005319 delavirdine Drugs 0.000 claims description 3
- 229960002656 didanosine Drugs 0.000 claims description 3
- XNHZXMPLVSJQFK-UHFFFAOYSA-O dimethyl-[[4-[[3-(4-methylphenyl)-8,9-dihydro-7h-benzo[7]annulene-6-carbonyl]amino]phenyl]methyl]-(oxan-4-yl)azanium Chemical compound C1=CC(C)=CC=C1C1=CC=C(CCCC(=C2)C(=O)NC=3C=CC(C[N+](C)(C)C4CCOCC4)=CC=3)C2=C1 XNHZXMPLVSJQFK-UHFFFAOYSA-O 0.000 claims description 3
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims description 3
- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 claims description 3
- 229960003804 efavirenz Drugs 0.000 claims description 3
- 229950010245 ibalizumab Drugs 0.000 claims description 3
- 229960001936 indinavir Drugs 0.000 claims description 3
- 239000002850 integrase inhibitor Substances 0.000 claims description 3
- 229940124524 integrase inhibitor Drugs 0.000 claims description 3
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 claims description 3
- 229960001627 lamivudine Drugs 0.000 claims description 3
- 229950004697 lasinavir Drugs 0.000 claims description 3
- 229940121292 leronlimab Drugs 0.000 claims description 3
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- VRRUCOIDXOAASA-UHFFFAOYSA-N tert-butyl 4-[2-(phenylmethoxycarbonylaminomethyl)-1h-benzimidazol-4-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC2=C1N=C(CNC(=O)OCC=1C=CC=CC=1)N2 VRRUCOIDXOAASA-UHFFFAOYSA-N 0.000 description 1
- LZRDHSFPLUWYAX-UHFFFAOYSA-N tert-butyl 4-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)CC1 LZRDHSFPLUWYAX-UHFFFAOYSA-N 0.000 description 1
- QYJVBVKFXDHFPQ-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)-n-methylcarbamate Chemical compound NCCN(C)C(=O)OC(C)(C)C QYJVBVKFXDHFPQ-UHFFFAOYSA-N 0.000 description 1
- PVPLWNKSNCRQIL-UHFFFAOYSA-N tert-butyl n-(2-oxo-2-piperazin-1-ylethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC(=O)N1CCNCC1 PVPLWNKSNCRQIL-UHFFFAOYSA-N 0.000 description 1
- XDJCYKMWJCYQJM-UHFFFAOYSA-N tert-butyl n-(3-hydroxypropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCO XDJCYKMWJCYQJM-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- NLJDBTZLVTWXRG-UHFFFAOYSA-N tert-butylazanium;iodide Chemical compound [I-].CC(C)(C)[NH3+] NLJDBTZLVTWXRG-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
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- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
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- 229910052721 tungsten Inorganic materials 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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- 230000029812 viral genome replication Effects 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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Landscapes
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- Emergency Medicine (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
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| US60192804P | 2004-08-16 | 2004-08-16 | |
| US60/601,928 | 2004-08-16 | ||
| PCT/US2005/028811 WO2006023400A2 (en) | 2004-08-16 | 2005-08-12 | Chemical compounds |
Publications (1)
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| AU2005277638A1 true AU2005277638A1 (en) | 2006-03-02 |
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| US7728026B2 (en) | 2005-04-11 | 2010-06-01 | Abbott Laboratories, Inc. | 2-substituted-1 h-benzimidazile-4-carboxamides are PARP inhibitors |
| US8318931B2 (en) | 2005-10-28 | 2012-11-27 | Ono Pharmaceutical Co., Ltd. | Chemokine receptor antagonists and use thereof |
| ES2407115T3 (es) | 2005-11-18 | 2013-06-11 | Ono Pharmaceutical Co., Ltd. | Compuesto que contiene un grupo básico y uso del mismo |
| 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 |
| US20090325992A1 (en) | 2006-07-31 | 2009-12-31 | Ono Pharmaceutical Co., Ltd. | Compound having cyclic group bound thereto through spiro binding and use thereof |
| GB0702695D0 (en) * | 2007-02-12 | 2007-03-21 | Ark Therapeutics Ltd | Production of vectors |
| CL2008002242A1 (es) * | 2007-07-31 | 2009-08-21 | Bayer Cropscience Ag | Compuestos derivados de n-cicloalquil-n-carboxamida, tiocarboxamida, biciclicas o derivados de carboximidamida n-sustituida; composicion fungicida; y metodo para controlar los hongos fitopatogenos de los cultivos. |
| WO2010098866A1 (en) | 2009-02-27 | 2010-09-02 | Supergen, Inc. | Cyclopentathiophene/cyclohexathiophene dna methyltransferase inhibitors |
| JP5541454B2 (ja) * | 2009-09-16 | 2014-07-09 | Ｊｓｒ株式会社 | 液晶配向剤および液晶表示素子 |
| JP5712524B2 (ja) * | 2009-10-28 | 2015-05-07 | Jsr株式会社 | 液晶配向剤および液晶表示素子 |
| MA34591B1 (fr) | 2010-10-06 | 2013-10-02 | Glaxosmithkline Llc | Dérivés de benzimidazole utilisés comme inhibiteurs de pi3 kinase |
| 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 |
| CN109069486A (zh) | 2015-12-14 | 2018-12-21 | X4 制药有限公司 | 治疗癌症的方法 |
| JP6864296B2 (ja) | 2015-12-14 | 2021-04-28 | 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 | がんを処置する方法 |
| WO2017112894A1 (en) | 2015-12-22 | 2017-06-29 | X4 Pharmaceuticals, Inc. | Methods for treating immunodeficiency disease |
| EP3440112A4 (en) | 2016-04-08 | 2019-10-09 | X4 Pharmaceuticals, Inc. | METHOD FOR THE TREATMENT OF CANCER |
| WO2017223243A1 (en) | 2016-06-21 | 2017-12-28 | X4 Pharmaceuticals, Inc. | Cxcr4 inhibitors and uses thereof |
| CN109640988A (zh) | 2016-06-21 | 2019-04-16 | X4 制药有限公司 | Cxcr4抑制剂及其用途 |
| JP7054529B2 (ja) | 2016-06-21 | 2022-04-14 | 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 | Ｃｘｃｒ４阻害剤およびその使用 |
| IL309069A (en) | 2017-02-21 | 2024-02-01 | Univ Emory | CXCR4 cytokine receptor modulators and related uses |
| JP7282786B2 (ja) * | 2017-09-25 | 2023-05-29 | シージーンテック （スーチョウ， チャイナ） カンパニー リミテッド | Ｃｘｃｒ４阻害剤としてのヘテロアリール化合物、それを用いた組成物及び方法 |
| 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 |
| EP3768256A4 (en) | 2018-03-19 | 2021-11-24 | Emory University | PANTROPIC ENTRY INHIBITORS |
| US10548889B1 (en) | 2018-08-31 | 2020-02-04 | X4 Pharmaceuticals, Inc. | Compositions of CXCR4 inhibitors and methods of preparation and use |
| CA3171250A1 (en) | 2020-03-10 | 2021-09-16 | E. Lynne KELLEY | Methods for treating neutropenia |
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| 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 |
| RU2006136381A (ru) * | 2004-03-15 | 2008-04-27 | Анормед, Инк. (Ca) | Способ получения антагониста cxcr4 |
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2005
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- 2005-08-12 RU RU2007105823/04A patent/RU2350604C2/ru not_active IP Right Cessation
- 2005-08-12 JP JP2007527895A patent/JP2008510006A/ja active Pending
- 2005-08-12 EP EP05786708A patent/EP1789045A2/en not_active Withdrawn
- 2005-08-12 MX MX2007001958A patent/MX2007001958A/es not_active Application Discontinuation
- 2005-08-12 AU AU2005277638A patent/AU2005277638A1/en not_active Abandoned
- 2005-08-12 US US11/573,729 patent/US20080045537A1/en not_active Abandoned
- 2005-08-12 WO PCT/US2005/028811 patent/WO2006023400A2/en not_active Ceased
- 2005-08-12 KR KR1020077005000A patent/KR20070042568A/ko not_active Withdrawn
- 2005-08-12 TW TW094127423A patent/TW200619217A/zh unknown
- 2005-08-12 CN CNA2005800351651A patent/CN101039672A/zh active Pending
- 2005-08-12 CA CA002577100A patent/CA2577100A1/en not_active Abandoned
- 2005-08-12 BR BRPI0514438-8A patent/BRPI0514438A/pt not_active IP Right Cessation
- 2005-08-12 PE PE2005000940A patent/PE20060646A1/es not_active Application Discontinuation
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2007
- 2007-02-05 IL IL181160A patent/IL181160A0/en unknown
- 2007-02-13 ZA ZA200701282A patent/ZA200701282B/xx unknown
- 2007-02-21 MA MA29700A patent/MA28814B1/fr unknown
- 2007-03-01 NO NO20071161A patent/NO20071161L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007001958A (es) | 2007-05-09 |
| AR050522A1 (es) | 2006-11-01 |
| ZA200701282B (en) | 2010-05-26 |
| US20080045537A1 (en) | 2008-02-21 |
| RU2350604C2 (ru) | 2009-03-27 |
| TW200619217A (en) | 2006-06-16 |
| RU2007105823A (ru) | 2008-09-27 |
| CN101039672A (zh) | 2007-09-19 |
| WO2006023400A3 (en) | 2006-06-08 |
| MA28814B1 (fr) | 2007-08-01 |
| BRPI0514438A (pt) | 2008-06-10 |
| WO2006023400A2 (en) | 2006-03-02 |
| JP2008510006A (ja) | 2008-04-03 |
| IL181160A0 (en) | 2007-07-04 |
| PE20060646A1 (es) | 2006-08-04 |
| EP1789045A2 (en) | 2007-05-30 |
| KR20070042568A (ko) | 2007-04-23 |
| NO20071161L (no) | 2007-05-14 |
| CA2577100A1 (en) | 2006-03-02 |
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