CA2575560A1 - Chemical compounds - Google Patents

Info

Publication number

CA2575560A1

CA2575560A1 CA002575560A CA2575560A CA2575560A1 CA 2575560 A1 CA2575560 A1 CA 2575560A1 CA 002575560 A CA002575560 A CA 002575560A CA 2575560 A CA2575560 A CA 2575560A CA 2575560 A1 CA2575560 A1 CA 2575560A1

Authority

CA

Canada

Prior art keywords

methyl

tetrahydro

benzimidazol

quinolinamine

het

Prior art date

2004-08-02

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 251
• 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims abstract description 24
• 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims abstract description 24
• 208000031886 HIV Infections Diseases 0.000 claims abstract description 19
• 208000037357 HIV infectious disease Diseases 0.000 claims abstract description 19
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims abstract description 19
• 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 13
• 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims abstract description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 176
• 238000002360 preparation method Methods 0.000 claims description 142
• 239000000203 mixture Substances 0.000 claims description 121
• -1 piperizinyl Chemical group 0.000 claims description 121
• 125000000217 alkyl group Chemical group 0.000 claims description 84
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 71
• 125000003342 alkenyl group Chemical group 0.000 claims description 56
• 125000000304 alkynyl group Chemical group 0.000 claims description 56
• 238000000034 method Methods 0.000 claims description 55
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 52
• 238000011282 treatment Methods 0.000 claims description 41
• 239000003795 chemical substances by application Substances 0.000 claims description 37
• 150000003839 salts Chemical class 0.000 claims description 33
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
• 125000001188 haloalkyl group Chemical group 0.000 claims description 31
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 150000002367 halogens Chemical group 0.000 claims description 31
• 125000001072 heteroaryl group Chemical group 0.000 claims description 24
• 239000012453 solvate Substances 0.000 claims description 24
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 23
• 201000010099 disease Diseases 0.000 claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims description 23
• VETGEHMWKIZMPG-UHFFFAOYSA-N n-methyl-n-[[1-[(1-methylpiperidin-3-yl)methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC1CCCN(C)C1 VETGEHMWKIZMPG-UHFFFAOYSA-N 0.000 claims description 21
• 150000001412 amines Chemical group 0.000 claims description 19
• 125000002883 imidazolyl group Chemical group 0.000 claims description 19
• OQMAUHRSKCHLHU-UHFFFAOYSA-N n-methyl-n-[[1-(pyridin-3-ylmethyl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC1=CC=CN=C1 OQMAUHRSKCHLHU-UHFFFAOYSA-N 0.000 claims description 19
• 238000006268 reductive amination reaction Methods 0.000 claims description 19
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 17
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• UPBCAKKETXMWBJ-UHFFFAOYSA-N n-[[1-(3-aminopropyl)benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CCCN UPBCAKKETXMWBJ-UHFFFAOYSA-N 0.000 claims description 17
• 230000008569 process Effects 0.000 claims description 17
• 238000011321 prophylaxis Methods 0.000 claims description 17
• 230000000694 effects Effects 0.000 claims description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
• 208000029523 Interstitial Lung disease Diseases 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 15
• 230000002757 inflammatory effect Effects 0.000 claims description 15
• 201000004624 Dermatitis Diseases 0.000 claims description 14
• 201000004681 Psoriasis Diseases 0.000 claims description 14
• 208000026935 allergic disease Diseases 0.000 claims description 14
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 14
• 230000002708 enhancing effect Effects 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
• 206010061218 Inflammation Diseases 0.000 claims description 13
• 206010028980 Neoplasm Diseases 0.000 claims description 13
• 125000002947 alkylene group Chemical group 0.000 claims description 13
• 230000004054 inflammatory process Effects 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• XHRXIYNWBWPAAC-AVRDEDQJSA-N (8s)-n-methyl-n-[[1-[[(3s)-piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCNC1 XHRXIYNWBWPAAC-AVRDEDQJSA-N 0.000 claims description 11
• 125000004450 alkenylene group Chemical group 0.000 claims description 11
• 125000004419 alkynylene group Chemical group 0.000 claims description 11
• 125000005724 cycloalkenylene group Chemical group 0.000 claims description 11
• 150000003973 alkyl amines Chemical group 0.000 claims description 10
• 239000003112 inhibitor Substances 0.000 claims description 10
• SAIRRLKOMQEJAC-UHFFFAOYSA-N n-methyl-n-[[1-[2-(1-methylpiperidin-2-yl)ethyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CCC1CCCCN1C SAIRRLKOMQEJAC-UHFFFAOYSA-N 0.000 claims description 10
• 125000003107 substituted aryl group Chemical group 0.000 claims description 10
• CGEYSKSKPCRPDK-UHFFFAOYSA-N n-methyl-n-[[1-(2-piperidin-1-ylethyl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CCN1CCCCC1 CGEYSKSKPCRPDK-UHFFFAOYSA-N 0.000 claims description 9
• SIQJINIEOSWWSC-UHFFFAOYSA-N n-methyl-n-[[1-(piperidin-4-ylmethyl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC1CCNCC1 SIQJINIEOSWWSC-UHFFFAOYSA-N 0.000 claims description 9
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
• 208000006673 asthma Diseases 0.000 claims description 8
• 208000035475 disorder Diseases 0.000 claims description 8
• 208000032839 leukemia Diseases 0.000 claims description 8
• AMJRGYWDPGQUFD-SREVYHEPSA-N n-[[1-[(z)-4-(dimethylamino)but-2-enyl]benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC=C2N(C\C=C/CN(C)C)C(CN(C)C3C4=NC=CC=C4CCC3)=NC2=C1 AMJRGYWDPGQUFD-SREVYHEPSA-N 0.000 claims description 8
• JEPDGRCNPREMJT-UHFFFAOYSA-N n-[[1-[3-(dimethylamino)propyl]benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC=C2N(CCCN(C)C)C(CN(C)C3C4=NC=CC=C4CCC3)=NC2=C1 JEPDGRCNPREMJT-UHFFFAOYSA-N 0.000 claims description 8
• IBMXMPNDZLRVME-UHFFFAOYSA-N n-methyl-n-[[1-[(1-methylazetidin-3-yl)methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC1CN(C)C1 IBMXMPNDZLRVME-UHFFFAOYSA-N 0.000 claims description 8
• 210000001519 tissue Anatomy 0.000 claims description 8
• QSKQVYGGIODIIN-BWKNWUBXSA-N (8s)-n-methyl-n-[[1-[[(3r)-1-propan-2-ylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1N(C(C)C)CCC[C@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@@H]1C2=NC=CC=C2CCC1 QSKQVYGGIODIIN-BWKNWUBXSA-N 0.000 claims description 7
• KNNLCWNQAVHYHR-FIPFOOKPSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-(pyridin-2-ylmethyl)piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C([C@@H](C1)CN2C3=CC=CC=C3N=C2CN(C)[C@@H]2C3=NC=CC=C3CCC2)CCN1CC1=CC=CC=N1 KNNLCWNQAVHYHR-FIPFOOKPSA-N 0.000 claims description 7
• OGKYHMHLZSDZND-RDPSFJRHSA-N 2-[(3s)-3-[[2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]benzimidazol-1-yl]methyl]piperidin-1-yl]ethanol Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCN(CCO)C1 OGKYHMHLZSDZND-RDPSFJRHSA-N 0.000 claims description 7
• ZGXWKJJTZYBTPX-OFVILXPXSA-N 3-[(3s)-3-[[2-[[methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]methyl]benzimidazol-1-yl]methyl]piperidin-1-yl]propan-1-ol Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCN(CCCO)C1 ZGXWKJJTZYBTPX-OFVILXPXSA-N 0.000 claims description 7
• 206010058284 Allergy to arthropod sting 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
• 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
• 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
• 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
• 230000001404 mediated effect Effects 0.000 claims description 7
• HEPWOFBXMDSUEO-UHFFFAOYSA-N n-[[1-(3-aminopropyl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC=C2N(CCCN)C(CNC3C4=NC=CC=C4CCC3)=NC2=C1 HEPWOFBXMDSUEO-UHFFFAOYSA-N 0.000 claims description 7
• BBOCVTVNQPABFO-UHFFFAOYSA-N n-[[1-[[4-(aminomethyl)phenyl]methyl]benzimidazol-2-yl]methyl]-n-methyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC1=CC=C(CN)C=C1 BBOCVTVNQPABFO-UHFFFAOYSA-N 0.000 claims description 7
• FFROZRURSWKTSQ-UHFFFAOYSA-N n-methyl-n-[[1-(1-methylpiperidin-4-yl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1C1CCN(C)CC1 FFROZRURSWKTSQ-UHFFFAOYSA-N 0.000 claims description 7
• CEZDJMFFDIZREC-UHFFFAOYSA-N n-methyl-n-[[1-(2-piperidin-2-ylethyl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CCC1CCCCN1 CEZDJMFFDIZREC-UHFFFAOYSA-N 0.000 claims description 7
• NTSBJKADBVYMSM-UHFFFAOYSA-N n-methyl-n-[[1-[(1-methylpyrrolidin-3-yl)methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC1CCN(C)C1 NTSBJKADBVYMSM-UHFFFAOYSA-N 0.000 claims description 7
• 230000002956 necrotizing effect Effects 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
• 230000001225 therapeutic effect Effects 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
• VETGEHMWKIZMPG-CVDCTZTESA-N (8s)-n-methyl-n-[[1-[[(3s)-1-methylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCN(C)C1 VETGEHMWKIZMPG-CVDCTZTESA-N 0.000 claims description 6
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 6
• PXSYBAMOAXOVKV-OFVILXPXSA-N 3-[[1-[[(3s)-1-methylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]propan-1-ol Chemical compound C1N(C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(CCCO)[C@@H]1C2=NC=CC=C2CCC1 PXSYBAMOAXOVKV-OFVILXPXSA-N 0.000 claims description 6
• 206010002198 Anaphylactic 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
• 208000003455 anaphylaxis 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
• 239000003937 drug carrier Substances 0.000 claims description 6
• 210000004072 lung Anatomy 0.000 claims description 6
• ASCHSOKJVZUWMP-UHFFFAOYSA-N n-[[1-(3-aminopropyl)benzimidazol-2-yl]methyl]-n-ethyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(CC)CC1=NC2=CC=CC=C2N1CCCN ASCHSOKJVZUWMP-UHFFFAOYSA-N 0.000 claims description 6
• LJLXFECAEZYHOF-UHFFFAOYSA-N n-methyl-n-[[1-(pyrrolidin-3-ylmethyl)benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC1CCNC1 LJLXFECAEZYHOF-UHFFFAOYSA-N 0.000 claims description 6
• SMYBYHLPPUNRDO-UHFFFAOYSA-N n-methyl-n-[[1-[3-(3-methylbutylamino)propyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC=C2N(CCCNCCC(C)C)C(CN(C)C3C4=NC=CC=C4CCC3)=NC2=C1 SMYBYHLPPUNRDO-UHFFFAOYSA-N 0.000 claims description 6
• CIPHJLFMKDPVDS-UHFFFAOYSA-N n-methyl-n-[[1-[3-(4-methylpiperazin-1-yl)propyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CCCN1CCN(C)CC1 CIPHJLFMKDPVDS-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
• 210000002307 prostate Anatomy 0.000 claims description 6
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• XHRXIYNWBWPAAC-GCJKJVERSA-N (8s)-n-methyl-n-[[1-[[(3r)-piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@@H]1CCCNC1 XHRXIYNWBWPAAC-GCJKJVERSA-N 0.000 claims description 5
• SUVTXSXXZWCMHL-NVQXNPDNSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-(2-methylpropyl)piperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1N(CC(C)C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@@H]1C2=NC=CC=C2CCC1 SUVTXSXXZWCMHL-NVQXNPDNSA-N 0.000 claims description 5
• QSKQVYGGIODIIN-OFVILXPXSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-propan-2-ylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1N(C(C)C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(C)[C@@H]1C2=NC=CC=C2CCC1 QSKQVYGGIODIIN-OFVILXPXSA-N 0.000 claims description 5
• RJUSPAJEXRXMFD-UHFFFAOYSA-N 2-[2,2-dimethyl-3-[2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]benzimidazol-1-yl]propyl]guanidine Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC(C)(C)CNC(N)=N RJUSPAJEXRXMFD-UHFFFAOYSA-N 0.000 claims description 5
• HNPRTVLVYBDBAL-HOFKKMOUSA-N 3-[[1-[[(3s)-1-propan-2-ylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]amino]propan-1-ol Chemical compound C1N(C(C)C)CCC[C@@H]1CN1C2=CC=CC=C2N=C1CN(CCCO)[C@@H]1C2=NC=CC=C2CCC1 HNPRTVLVYBDBAL-HOFKKMOUSA-N 0.000 claims description 5
• 206010039710 Scleroderma Diseases 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• OCODMMOTZUFEQM-UHFFFAOYSA-N n-(2-aminoethyl)-2-[2-[[methyl(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]benzimidazol-1-yl]acetamide Chemical compound C1CCC2=CC=CN=C2C1N(C)CC1=NC2=CC=CC=C2N1CC(=O)NCCN OCODMMOTZUFEQM-UHFFFAOYSA-N 0.000 claims description 5
• OQIOXYYMSVUMHC-UHFFFAOYSA-N n-[[1-[3-(dimethylamino)propyl]benzimidazol-2-yl]methyl]-n-propan-2-yl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1CCC2=CC=CN=C2C1N(C(C)C)CC1=NC2=CC=CC=C2N1CCCN(C)C OQIOXYYMSVUMHC-UHFFFAOYSA-N 0.000 claims description 5
• 125000003729 nucleotide group Chemical group 0.000 claims description 5
• CKNAQFVBEHDJQV-UHFFFAOYSA-N oltipraz Chemical compound S1SC(=S)C(C)=C1C1=CN=CC=N1 CKNAQFVBEHDJQV-UHFFFAOYSA-N 0.000 claims description 5
• 229950008687 oltipraz Drugs 0.000 claims description 5
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