CA2575560A1

CA2575560A1 - Chemical compounds

Chemical compounds Download PDF

Info

Publication number: CA2575560A1
Authority: CA; Canada
Prior art keywords: methyl; tetrahydro; benzimidazol; quinolinamine; het
Prior art date: 2004-08-02
Legal status : Abandoned

Application number

CA002575560A

Other languages

English (en)

French (fr)

Inventor

Kristjan Gudmundsson

John Franklin Miller

Elizabeth Madalena Turner

Current Assignee

SmithKline Beecham Corp

Original Assignee

Individual

Priority date

2004-08-02

Filing date

2005-07-29

Publication date

2006-02-23

2005-07-29 Application filed by Individual filed Critical Individual

2006-02-23 Publication of CA2575560A1 publication Critical patent/CA2575560A1/en

Status Abandoned legal-status Critical Current

Links

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
OVVVPNSGDFVCAW-HOFKKMOUSA-N (8s)-n-[[1-[[(3s)-1-propan-2-ylpiperidin-3-yl]methyl]benzimidazol-2-yl]methyl]-n-propyl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCCN([C@@H]1C2=NC=CC=C2CCC1)CC1=NC2=CC=CC=C2N1C[C@H]1CCCN(C(C)C)C1 OVVVPNSGDFVCAW-HOFKKMOUSA-N 0.000 claims description 4
KSHLOXFXDIORRL-CUBQBAPOSA-N (8s)-n-methyl-n-[[1-[[(3s)-1-(pyridin-4-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=NC=C1 KSHLOXFXDIORRL-CUBQBAPOSA-N 0.000 claims description 4
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