JP2004529132A5 - - Google Patents
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- JP2004529132A5 JP2004529132A5 JP2002576237A JP2002576237A JP2004529132A5 JP 2004529132 A5 JP2004529132 A5 JP 2004529132A5 JP 2002576237 A JP2002576237 A JP 2002576237A JP 2002576237 A JP2002576237 A JP 2002576237A JP 2004529132 A5 JP2004529132 A5 JP 2004529132A5
- Authority
- JP
- Japan
- Prior art keywords
- dimethoxy
- ethyl
- isoquinolin
- dihydro
- urea
- 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
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- 150000001875 compounds Chemical class 0.000 claims 23
- -1 [1,8] naphthyridin-4-yl Chemical group 0.000 claims 19
- 239000004202 carbamide Substances 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 4
- 206010019280 Heart failures Diseases 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 206010012289 Dementia Diseases 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 208000002815 pulmonary hypertension Diseases 0.000 claims 3
- 230000002792 vascular Effects 0.000 claims 3
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims 2
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 2
- 208000002177 Cataract Diseases 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims 2
- 108010036949 Cyclosporine Proteins 0.000 claims 2
- 206010011878 Deafness Diseases 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- 208000002249 Diabetes Complications Diseases 0.000 claims 2
- 206010012655 Diabetic complications Diseases 0.000 claims 2
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 2
- 208000003782 Raynaud disease Diseases 0.000 claims 2
- 208000012322 Raynaud phenomenon Diseases 0.000 claims 2
- 208000001647 Renal Insufficiency Diseases 0.000 claims 2
- 206010038419 Renal colic Diseases 0.000 claims 2
- 206010063897 Renal ischaemia Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 claims 2
- 229940116211 Vasopressin antagonist Drugs 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 238000002399 angioplasty Methods 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 206010003119 arrhythmia Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 201000005008 bacterial sepsis Diseases 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 238000007675 cardiac surgery Methods 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 208000007451 chronic bronchitis Diseases 0.000 claims 2
- 208000020832 chronic kidney disease Diseases 0.000 claims 2
- 229960001265 ciclosporin Drugs 0.000 claims 2
- 231100000867 compulsive behavior Toxicity 0.000 claims 2
- 239000012050 conventional carrier Substances 0.000 claims 2
- 229930182912 cyclosporin Natural products 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000010370 hearing loss Effects 0.000 claims 2
- 231100000888 hearing loss Toxicity 0.000 claims 2
- 208000016354 hearing loss disease Diseases 0.000 claims 2
- 201000001881 impotence Diseases 0.000 claims 2
- 208000001286 intracranial vasospasm Diseases 0.000 claims 2
- 201000006370 kidney failure Diseases 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 208000031225 myocardial ischemia Diseases 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 208000007232 portal hypertension Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 201000004240 prostatic hypertrophy Diseases 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 230000035939 shock Effects 0.000 claims 2
- 208000007056 sickle cell anemia Diseases 0.000 claims 2
- 125000005504 styryl group Chemical group 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 230000006016 thyroid dysfunction Effects 0.000 claims 2
- 238000002054 transplantation Methods 0.000 claims 2
- 238000007631 vascular surgery Methods 0.000 claims 2
- 239000003038 vasopressin antagonist Substances 0.000 claims 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical group C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 1
- RFPPNJDJUXZQMC-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-6-methoxy-2-[2-[(2-methylquinolin-4-yl)carbamoylamino]ethyl]-n-propyl-3,4-dihydro-1h-isoquinoline-7-carboxamide Chemical compound C=1C(C)=NC2=CC=CC=C2C=1NC(=O)NCCN1CCC=2C=C(OC)C(C(=O)NCCC)=CC=2C1CC1=CC=C(Cl)C(Cl)=C1 RFPPNJDJUXZQMC-UHFFFAOYSA-N 0.000 claims 1
- LUXJJPBWULBAJN-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-6-methoxy-n,n-dimethyl-2-[2-[(2-methylquinolin-4-yl)carbamoylamino]ethyl]-3,4-dihydro-1h-isoquinoline-7-carboxamide Chemical compound C1=2C=C(C(=O)N(C)C)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CC1=CC=C(Cl)C(Cl)=C1 LUXJJPBWULBAJN-UHFFFAOYSA-N 0.000 claims 1
- PHRXGIDEEJSNTP-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-6-methoxy-n-methyl-2-[2-[(2-methylquinolin-4-yl)carbamoylamino]ethyl]-3,4-dihydro-1h-isoquinoline-7-carboxamide Chemical compound C=1C(C)=NC2=CC=CC=C2C=1NC(=O)NCCN1CCC=2C=C(OC)C(C(=O)NC)=CC=2C1CC1=CC=C(Cl)C(Cl)=C1 PHRXGIDEEJSNTP-UHFFFAOYSA-N 0.000 claims 1
- XOIVNJHHLSAOEI-UHFFFAOYSA-N 1-[2-(1-benzyl-5,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-3-quinolin-4-ylurea Chemical compound C=1C=NC2=CC=CC=C2C=1NC(=O)NCCN1CCC=2C(OC)=CC=C(OC)C=2C1CC1=CC=CC=C1 XOIVNJHHLSAOEI-UHFFFAOYSA-N 0.000 claims 1
- KTOSUZZARDNXEK-UHFFFAOYSA-N 1-[2-(1-benzyl-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CC1=CC=CC=C1 KTOSUZZARDNXEK-UHFFFAOYSA-N 0.000 claims 1
- MQEJLJNQXYVUFF-MUUNZHRXSA-N 1-[2-[(1r)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H]1C2=CC(OC)=C(OC)C=C2CCN1CCNC(=O)NC1=CC(C)=NC2=CC=CC=C12 MQEJLJNQXYVUFF-MUUNZHRXSA-N 0.000 claims 1
- QGNVFJPVQOKCIM-HHHXNRCGSA-N 1-[2-[(1r)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H]1C2=CC(OC)=C(OC)C=C2CCN1CCNC(=O)NC1=CC=NC2=CC=CC=C12 QGNVFJPVQOKCIM-HHHXNRCGSA-N 0.000 claims 1
- WLZQSCSPTZZOMK-MUUNZHRXSA-N 1-[2-[(1r)-1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C([C@H]1N(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)CCC=2C=C(C(=CC=21)OC)OC)C1=CC=C(F)C=C1 WLZQSCSPTZZOMK-MUUNZHRXSA-N 0.000 claims 1
- GKRDMWCAKIQXQU-UHFFFAOYSA-N 1-[2-[1-(1,3-benzodioxol-5-ylmethyl)-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=C2OCOC2=CC(CC2N(CCNC(=O)NC=3C4=CC=CC=C4N=C(C)C=3)CCC=3C=C(C(=CC=32)OC)OC)=C1 GKRDMWCAKIQXQU-UHFFFAOYSA-N 0.000 claims 1
- QUFCEURLAKMOKZ-UHFFFAOYSA-N 1-[2-[1-[(2,5-dimethoxyphenyl)methyl]-5,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound COC1=CC=C(OC)C(CC2C3=C(OC)C=CC(OC)=C3CCN2CCNC(=O)NC=2C3=CC=CC=C3N=CC=2)=C1 QUFCEURLAKMOKZ-UHFFFAOYSA-N 0.000 claims 1
- NEUKZVFYJQBISH-UHFFFAOYSA-N 1-[2-[1-[(2,5-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-pyridin-4-ylurea Chemical compound COC1=CC=C(OC)C(CC2C3=CC(OC)=C(OC)C=C3CCN2CCNC(=O)NC=2C=CN=CC=2)=C1 NEUKZVFYJQBISH-UHFFFAOYSA-N 0.000 claims 1
- HDKOEMTWLBMZQD-UHFFFAOYSA-N 1-[2-[1-[(2,5-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound COC1=CC=C(OC)C(CC2C3=CC(OC)=C(OC)C=C3CCN2CCNC(=O)NC=2C3=CC=CC=C3N=CC=2)=C1 HDKOEMTWLBMZQD-UHFFFAOYSA-N 0.000 claims 1
- RFGAOISXGBDMGY-UHFFFAOYSA-N 1-[2-[1-[(2,6-dichlorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CC1=C(Cl)C=CC=C1Cl RFGAOISXGBDMGY-UHFFFAOYSA-N 0.000 claims 1
- VQVRTCJAZFRVAX-UHFFFAOYSA-N 1-[2-[1-[(3,4-difluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(F)C(F)=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)NC1=CC=NC=C1 VQVRTCJAZFRVAX-UHFFFAOYSA-N 0.000 claims 1
- ROCPYVNBCOHYOW-UHFFFAOYSA-N 1-[2-[1-[(3,4-difluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=CC=2)C1CC1=CC=C(F)C(F)=C1 ROCPYVNBCOHYOW-UHFFFAOYSA-N 0.000 claims 1
- DNKAIBBVRRUCHR-UHFFFAOYSA-N 1-[2-[1-[(3,4-difluorophenyl)methyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CC1=CC=C(F)C(F)=C1 DNKAIBBVRRUCHR-UHFFFAOYSA-N 0.000 claims 1
- MEUSKRITIACWPZ-UHFFFAOYSA-N 1-[2-[1-[(3,4-difluorophenyl)methyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=CC=2)C1CC1=CC=C(F)C(F)=C1 MEUSKRITIACWPZ-UHFFFAOYSA-N 0.000 claims 1
- VRUFFLAKHXKOCI-UHFFFAOYSA-N 1-[2-[1-[(3,4-dimethoxyphenyl)methyl]-5,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=C(OC)C=CC(OC)=C2CCN1CCNC(=O)NC1=CC=NC2=CC=CC=C12 VRUFFLAKHXKOCI-UHFFFAOYSA-N 0.000 claims 1
- OZLRIYYGYVYMMI-UHFFFAOYSA-N 1-[2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-pyridin-4-ylurea Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CCNC(=O)NC1=CC=NC=C1 OZLRIYYGYVYMMI-UHFFFAOYSA-N 0.000 claims 1
- QGNVFJPVQOKCIM-UHFFFAOYSA-N 1-[2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CCNC(=O)NC1=CC=NC2=CC=CC=C12 QGNVFJPVQOKCIM-UHFFFAOYSA-N 0.000 claims 1
- OCRHZJCCOVNLHO-UHFFFAOYSA-N 1-[2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-4,4-dimethyl-1,3-dihydroisoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2C(C)(C)CN1CCNC(=O)NC1=CC=NC2=CC=CC=C12 OCRHZJCCOVNLHO-UHFFFAOYSA-N 0.000 claims 1
- YJTXTLQNEIGRSQ-UHFFFAOYSA-N 1-[2-[1-[(3,4-dimethoxyphenyl)methyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(OC)C(OC)=CC=1CC1C=2C(OC)=CC(OC)=CC=2CCN1CCNC(=O)NC1=CC=NC=C1 YJTXTLQNEIGRSQ-UHFFFAOYSA-N 0.000 claims 1
- UIECUNILNQGGNZ-UHFFFAOYSA-N 1-[2-[1-[(3,4-dimethoxyphenyl)methyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=CC=2)C1CC1=CC=C(OC)C(OC)=C1 UIECUNILNQGGNZ-UHFFFAOYSA-N 0.000 claims 1
- OWBLVDZBFUEHPW-UHFFFAOYSA-N 1-[2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C=1C(C)=NC2=CC=CC=C2C=1NC(=O)NCCN1CCC2=CC(OC)=CC=C2C1CC1=CC=C(OC)C(OC)=C1 OWBLVDZBFUEHPW-UHFFFAOYSA-N 0.000 claims 1
- ZJKNYLSMSOPXOE-UHFFFAOYSA-N 1-[2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-pyridin-4-ylurea Chemical compound C=1C=NC=CC=1NC(=O)NCCN1CCC2=CC(OC)=CC=C2C1CC1=CC=C(OC)C(OC)=C1 ZJKNYLSMSOPXOE-UHFFFAOYSA-N 0.000 claims 1
- UDHCPEXYMISIIN-UHFFFAOYSA-N 1-[2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C=1C=NC2=CC=CC=C2C=1NC(=O)NCCN1CCC2=CC(OC)=CC=C2C1CC1=CC=C(OC)C(OC)=C1 UDHCPEXYMISIIN-UHFFFAOYSA-N 0.000 claims 1
- NJZTUXSCSSGVCL-UHFFFAOYSA-N 1-[2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-7-phenylmethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OCC=3C=CC=CC=3)=C(OC)C=C2CCN1CCNC(=O)NC1=CC(C)=NC2=CC=CC=C12 NJZTUXSCSSGVCL-UHFFFAOYSA-N 0.000 claims 1
- ISWYYYFVLWUNKT-UHFFFAOYSA-N 1-[2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1CCNC(=O)NC1=CC(C)=NC2=CC=CC=C12 ISWYYYFVLWUNKT-UHFFFAOYSA-N 0.000 claims 1
- UVOKHAODNWXOOV-UHFFFAOYSA-N 1-[2-[1-[(3-fluoro-4-methoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=C(F)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CCNC(=O)NC1=CC(C)=NC2=CC=CC=C12 UVOKHAODNWXOOV-UHFFFAOYSA-N 0.000 claims 1
- HKLUFKBITIIEIA-UHFFFAOYSA-N 1-[2-[1-[(3-fluoro-4-methoxyphenyl)methyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CC1=CC=C(OC)C(F)=C1 HKLUFKBITIIEIA-UHFFFAOYSA-N 0.000 claims 1
- ATMKZRUZWHMMPY-UHFFFAOYSA-N 1-[2-[1-[(4-chlorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(Cl)C=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)NC1=CC=NC=C1 ATMKZRUZWHMMPY-UHFFFAOYSA-N 0.000 claims 1
- ORSOGNBISVHNNV-UHFFFAOYSA-N 1-[2-[1-[(4-chlorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=CC=2)C1CC1=CC=C(Cl)C=C1 ORSOGNBISVHNNV-UHFFFAOYSA-N 0.000 claims 1
- WLZQSCSPTZZOMK-UHFFFAOYSA-N 1-[2-[1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CC1=CC=C(F)C=C1 WLZQSCSPTZZOMK-UHFFFAOYSA-N 0.000 claims 1
- IHPGIUGQRMJAMJ-UHFFFAOYSA-N 1-[2-[1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-pyrrolidin-1-ylpyridin-4-yl)urea Chemical compound C=1C=C(F)C=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)NC(C=1)=CC=NC=1N1CCCC1 IHPGIUGQRMJAMJ-UHFFFAOYSA-N 0.000 claims 1
- UVXNPDXMWNAWLY-UHFFFAOYSA-N 1-[2-[1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(5,6,7,8-tetrahydroquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C=3CCCCC=3N=CC=2)C1CC1=CC=C(F)C=C1 UVXNPDXMWNAWLY-UHFFFAOYSA-N 0.000 claims 1
- NZJLTTPPHKWCCD-UHFFFAOYSA-N 1-[2-[1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(7-methyl-1,8-naphthyridin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=C(C)N=C3N=CC=2)C1CC1=CC=C(F)C=C1 NZJLTTPPHKWCCD-UHFFFAOYSA-N 0.000 claims 1
- ZUIMCAJQNYQHEC-UHFFFAOYSA-N 1-[2-[1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-[2-(n-methylanilino)pyridin-4-yl]urea Chemical compound C=1C=C(F)C=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)NC(C=1)=CC=NC=1N(C)C1=CC=CC=C1 ZUIMCAJQNYQHEC-UHFFFAOYSA-N 0.000 claims 1
- QSCMGGAUXQSOBW-UHFFFAOYSA-N 1-[2-[1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(F)C=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)NC1=CC=NC=C1 QSCMGGAUXQSOBW-UHFFFAOYSA-N 0.000 claims 1
- QDBTYGGDJBGFRP-UHFFFAOYSA-N 1-[2-[1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=CC=2)C1CC1=CC=C(F)C=C1 QDBTYGGDJBGFRP-UHFFFAOYSA-N 0.000 claims 1
- SXOLGZSJYMSVIZ-UHFFFAOYSA-N 1-[2-[1-[(4-fluorophenyl)methyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CC1=CC=C(F)C=C1 SXOLGZSJYMSVIZ-UHFFFAOYSA-N 0.000 claims 1
- RJSQZTPLUCJHMY-UHFFFAOYSA-N 1-[2-[1-[(4-fluorophenyl)methyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=CC=2)C1CC1=CC=C(F)C=C1 RJSQZTPLUCJHMY-UHFFFAOYSA-N 0.000 claims 1
- MTZYDBVBDQNBKM-PKNBQFBNSA-N 1-[2-[1-[(e)-2-(2,4-difluorophenyl)ethenyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1\C=C\C1=CC=C(F)C=C1F MTZYDBVBDQNBKM-PKNBQFBNSA-N 0.000 claims 1
- JUNVRDOMJRARAL-DHZHZOJOSA-N 1-[2-[1-[(e)-2-(2,5-difluorophenyl)ethenyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1\C=C\C1=CC(F)=CC=C1F JUNVRDOMJRARAL-DHZHZOJOSA-N 0.000 claims 1
- VKQLEIRHPPMCKE-UHFFFAOYSA-N 1-[2-[1-[2-(2,3-difluorophenyl)ethyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CCC1=CC=CC(F)=C1F VKQLEIRHPPMCKE-UHFFFAOYSA-N 0.000 claims 1
- QIGQQWYZLWWODQ-UHFFFAOYSA-N 1-[2-[1-[2-(2,4-difluorophenyl)ethyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CCC1=CC=C(F)C=C1F QIGQQWYZLWWODQ-UHFFFAOYSA-N 0.000 claims 1
- DVQVIKJCHOJWHO-UHFFFAOYSA-N 1-[2-[1-[2-(2,4-difluorophenyl)ethyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CCC1=CC=C(F)C=C1F DVQVIKJCHOJWHO-UHFFFAOYSA-N 0.000 claims 1
- CQSDVWQVMYZYDR-UHFFFAOYSA-N 1-[2-[1-[2-(2,4-difluorophenyl)ethyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=CC=2)C1CCC1=CC=C(F)C=C1F CQSDVWQVMYZYDR-UHFFFAOYSA-N 0.000 claims 1
- QOASOYQYNFSWQE-UHFFFAOYSA-N 1-[2-[1-[2-(2,5-difluorophenyl)ethyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CCC1=CC(F)=CC=C1F QOASOYQYNFSWQE-UHFFFAOYSA-N 0.000 claims 1
- PQTNBDKYTJTDHA-UHFFFAOYSA-N 1-[2-[1-[2-(3,4-difluorophenyl)ethyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CCC1=CC=C(F)C(F)=C1 PQTNBDKYTJTDHA-UHFFFAOYSA-N 0.000 claims 1
- XPWUBFIAZOORKB-UHFFFAOYSA-N 1-[2-[1-[2-(3,4-difluorophenyl)ethyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CCC1=CC=C(F)C(F)=C1 XPWUBFIAZOORKB-UHFFFAOYSA-N 0.000 claims 1
- BUNQYJQKVYFSMP-UHFFFAOYSA-N 1-[2-[1-[2-(3,4-difluorophenyl)ethyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=CC=2)C1CCC1=CC=C(F)C(F)=C1 BUNQYJQKVYFSMP-UHFFFAOYSA-N 0.000 claims 1
- VZKLNAOSSVMIIP-UHFFFAOYSA-N 1-[2-[1-[2-(3,4-dimethoxyphenyl)ethyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=C(OC)C(OC)=CC=C1CCC1C2=CC(OC)=C(OC)C=C2CCN1CCNC(=O)NC1=CC(C)=NC2=CC=CC=C12 VZKLNAOSSVMIIP-UHFFFAOYSA-N 0.000 claims 1
- CKNITIJUFATYRA-UHFFFAOYSA-N 1-[2-[1-[2-(4-fluorophenyl)ethyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CCC1=CC=C(F)C=C1 CKNITIJUFATYRA-UHFFFAOYSA-N 0.000 claims 1
- CBJSOSSLXHWJES-UHFFFAOYSA-N 1-[2-[1-[2-(4-fluorophenyl)ethyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CCC1=CC=C(F)C=C1 CBJSOSSLXHWJES-UHFFFAOYSA-N 0.000 claims 1
- JFOHOACMTXTFEJ-UHFFFAOYSA-N 1-[2-[1-[2-(4-fluorophenyl)ethyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=CC=2)C1CCC1=CC=C(F)C=C1 JFOHOACMTXTFEJ-UHFFFAOYSA-N 0.000 claims 1
- UIWBDXPKPMRUIC-UHFFFAOYSA-N 1-[2-[1-[2-[2,5-bis(trifluoromethyl)phenyl]ethyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CCC1=CC(C(F)(F)F)=CC=C1C(F)(F)F UIWBDXPKPMRUIC-UHFFFAOYSA-N 0.000 claims 1
- LDPHFEZLYIPCAR-UHFFFAOYSA-N 1-[2-[1-[2-[3,5-bis(trifluoromethyl)phenyl]ethyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 LDPHFEZLYIPCAR-UHFFFAOYSA-N 0.000 claims 1
- AGYGNQJZSMAYCK-UHFFFAOYSA-N 1-[2-[1-[[3-fluoro-5-(trifluoromethyl)phenyl]methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CC1=CC(F)=CC(C(F)(F)F)=C1 AGYGNQJZSMAYCK-UHFFFAOYSA-N 0.000 claims 1
- OGJRMTDWDPHNLA-UHFFFAOYSA-N 1-[2-[5-[(3,4-dimethoxyphenyl)methyl]-7,8-dihydro-5h-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]ethyl]-3-pyridin-4-ylurea Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OCO3)=C3C=C2CCN1CCNC(=O)NC1=CC=NC=C1 OGJRMTDWDPHNLA-UHFFFAOYSA-N 0.000 claims 1
- RYQFRZDZAAGEAL-UHFFFAOYSA-N 1-[2-[5-[(3,4-dimethoxyphenyl)methyl]-7,8-dihydro-5h-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OCO3)=C3C=C2CCN1CCNC(=O)NC1=CC=NC2=CC=CC=C12 RYQFRZDZAAGEAL-UHFFFAOYSA-N 0.000 claims 1
- KOHVVQNLIYTZBA-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-(1-phenylethyl)-3,4-dihydro-1H-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound COC=1C=C2CCN(C(C2=CC=1OC)C(C)C1=CC=CC=C1)CCNC(=O)NC1=CC(=NC2=CC=CC=C12)C KOHVVQNLIYTZBA-UHFFFAOYSA-N 0.000 claims 1
- SBGOWFVEWSGPNI-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-(1-phenylpropyl)-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C=1C=NC2=CC=CC=C2C=1NC(=O)NCCN1CCC2=CC(OC)=C(OC)C=C2C1C(CC)C1=CC=CC=C1 SBGOWFVEWSGPNI-UHFFFAOYSA-N 0.000 claims 1
- OOZPDPSTPKVOQC-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-(naphthalen-2-ylmethyl)-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-pyridin-4-ylurea Chemical compound C=1C=C2C=CC=CC2=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)NC1=CC=NC=C1 OOZPDPSTPKVOQC-UHFFFAOYSA-N 0.000 claims 1
- ZHOSPFFVKPOPTJ-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-(naphthalen-2-ylmethyl)-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=CC=CC2=CC(CC3N(CCNC(=O)NC=4C5=CC=CC=C5N=CC=4)CCC=4C=C(C(=CC=43)OC)OC)=CC=C21 ZHOSPFFVKPOPTJ-UHFFFAOYSA-N 0.000 claims 1
- VOBDGADYLJSQPZ-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-(phenoxymethyl)-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-pyridin-4-ylurea Chemical compound C=1C=CC=CC=1OCC1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)NC1=CC=NC=C1 VOBDGADYLJSQPZ-UHFFFAOYSA-N 0.000 claims 1
- LJYYFKIXGYSZTR-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CC1=CC(OC)=C(OC)C(OC)=C1 LJYYFKIXGYSZTR-UHFFFAOYSA-N 0.000 claims 1
- KTCVYHHPHGRXRO-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-[(3-methoxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-pyridin-4-ylurea Chemical compound COC1=CC=CC(CC2C3=CC(OC)=C(OC)C=C3CCN2CCNC(=O)NC=2C=CN=CC=2)=C1 KTCVYHHPHGRXRO-UHFFFAOYSA-N 0.000 claims 1
- YWNUIEDREMLAOK-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-[(3-methoxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound COC1=CC=CC(CC2C3=CC(OC)=C(OC)C=C3CCN2CCNC(=O)NC=2C3=CC=CC=C3N=CC=2)=C1 YWNUIEDREMLAOK-UHFFFAOYSA-N 0.000 claims 1
- PYSORJMROMESFH-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-pyridin-4-ylurea Chemical compound C1=CC(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CCNC(=O)NC1=CC=NC=C1 PYSORJMROMESFH-UHFFFAOYSA-N 0.000 claims 1
- JMECTUAHBMBUMN-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=CC(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CCNC(=O)NC1=CC=NC2=CC=CC=C12 JMECTUAHBMBUMN-UHFFFAOYSA-N 0.000 claims 1
- NTEQZNRTVXKHSY-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-[2-(2-methoxyphenyl)ethyl]-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound COC1=CC=CC=C1CCC1C2=CC(OC)=C(OC)C=C2CCN1CCNC(=O)NC1=CC(C)=NC2=CC=CC=C12 NTEQZNRTVXKHSY-UHFFFAOYSA-N 0.000 claims 1
- DXPHYORWDGJTMP-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-[2-(3-methoxyphenyl)ethyl]-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound COC1=CC=CC(CCC2C3=CC(OC)=C(OC)C=C3CCN2CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)=C1 DXPHYORWDGJTMP-UHFFFAOYSA-N 0.000 claims 1
- QTUGAYVLCTUHJW-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-[2-(4-methoxyphenyl)ethyl]-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=CC(OC)=CC=C1CCC1C2=CC(OC)=C(OC)C=C2CCN1CCNC(=O)NC1=CC(C)=NC2=CC=CC=C12 QTUGAYVLCTUHJW-UHFFFAOYSA-N 0.000 claims 1
- NXGWOZNOESUIFY-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-[2-[4-(trifluoromethyl)phenyl]ethyl]-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CCC1=CC=C(C(F)(F)F)C=C1 NXGWOZNOESUIFY-UHFFFAOYSA-N 0.000 claims 1
- GDRFTSSCPQFDMJ-UHFFFAOYSA-N 1-[2-[6-[(3,4-dimethoxyphenyl)methyl]-3,6,8,9-tetrahydro-2h-[1,4]dioxino[2,3-g]isoquinolin-7-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OCCO3)=C3C=C2CCN1CCNC(=O)NC1=CC=NC2=CC=CC=C12 GDRFTSSCPQFDMJ-UHFFFAOYSA-N 0.000 claims 1
- UNIVFGNNMJOQMT-UHFFFAOYSA-N 1-[2-[benzyl(methyl)amino]-6-methylpyridin-4-yl]-3-[2-[1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]urea Chemical compound C=1C=C(F)C=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)NC(C=1)=CC(C)=NC=1N(C)CC1=CC=CC=C1 UNIVFGNNMJOQMT-UHFFFAOYSA-N 0.000 claims 1
- NQKNPCBWMNVULG-UHFFFAOYSA-N 1-[2-[benzyl(methyl)amino]pyridin-4-yl]-3-[2-[1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]urea Chemical compound C=1C=C(F)C=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)NC(C=1)=CC=NC=1N(C)CC1=CC=CC=C1 NQKNPCBWMNVULG-UHFFFAOYSA-N 0.000 claims 1
- UEPRSRNLTSBHIS-UHFFFAOYSA-N 1-[3-(1-benzyl-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)propyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CC1=CC=CC=C1 UEPRSRNLTSBHIS-UHFFFAOYSA-N 0.000 claims 1
- JZPDLPMIPSBUPV-UHFFFAOYSA-N 1-[3-(1-benzyl-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)propyl]-3-quinolin-4-ylurea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCCNC(=O)NC=2C3=CC=CC=C3N=CC=2)C1CC1=CC=CC=C1 JZPDLPMIPSBUPV-UHFFFAOYSA-N 0.000 claims 1
- GDYATDNVHQVGNK-UHFFFAOYSA-N 1-[3-[1-[(3,4-dimethoxyphenyl)methyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]propyl]-3-(2-methylquinolin-4-yl)urea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCCNC(=O)NC=2C3=CC=CC=C3N=C(C)C=2)C1CC1=CC=C(OC)C(OC)=C1 GDYATDNVHQVGNK-UHFFFAOYSA-N 0.000 claims 1
- ODYVHJFICQAALM-UHFFFAOYSA-N 1-[3-[1-[(3,4-dimethoxyphenyl)methyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]propyl]-3-quinolin-4-ylurea Chemical compound C1=2C(OC)=CC(OC)=CC=2CCN(CCCNC(=O)NC=2C3=CC=CC=C3N=CC=2)C1CC1=CC=C(OC)C(OC)=C1 ODYVHJFICQAALM-UHFFFAOYSA-N 0.000 claims 1
- BDLRQSBAXSMVCV-UHFFFAOYSA-N 1-[3-[1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]propyl]-3-quinolin-4-ylurea Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCCNC(=O)NC=2C3=CC=CC=C3N=CC=2)C1CC1=CC=C(F)C=C1 BDLRQSBAXSMVCV-UHFFFAOYSA-N 0.000 claims 1
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- LLMWYJYBLHQIFV-UHFFFAOYSA-N 1-[3-[6,7-dimethoxy-1-(1-phenylethyl)-3,4-dihydro-1H-isoquinolin-2-yl]propyl]-3-quinolin-4-ylurea Chemical compound COC=1C=C2CCN(C(C2=CC=1OC)C(C)C1=CC=CC=C1)CCCNC(=O)NC1=CC=NC2=CC=CC=C12 LLMWYJYBLHQIFV-UHFFFAOYSA-N 0.000 claims 1
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- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 239000005541 ACE inhibitor Substances 0.000 claims 1
- 200000000007 Arterial disease Diseases 0.000 claims 1
- DPERKYKAEPJHCQ-UHFFFAOYSA-N C(C1=CC=CC=C1)(C1=CC=CC=C1)C1N(CCC2=CC(=C(C=C12)OC)OC)CCNC(=O)NC1=CC=NC=C1.C(C1=CC=CC=C1)(C1=CC=CC=C1)C1N(CCC2=C(C=CC(=C12)OC)OC)CCNC(=O)NC1=CC=NC2=CC=CC=C12 Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)C1N(CCC2=CC(=C(C=C12)OC)OC)CCNC(=O)NC1=CC=NC=C1.C(C1=CC=CC=C1)(C1=CC=CC=C1)C1N(CCC2=C(C=CC(=C12)OC)OC)CCNC(=O)NC1=CC=NC2=CC=CC=C12 DPERKYKAEPJHCQ-UHFFFAOYSA-N 0.000 claims 1
- CPUNJYIDTRWYQE-UHFFFAOYSA-N COC=1C=C2CCN(C(C2=CC1OC)C(C)C1=CC=CC=C1)CCNC(=O)NC1=CC=NC2=CC=CC=C12.COC=1C=C2CCN(C(C2=CC1OC)C(C)C1=CC=CC=C1)CCNC(=O)NC1=CC=NC=C1 Chemical compound COC=1C=C2CCN(C(C2=CC1OC)C(C)C1=CC=CC=C1)CCNC(=O)NC1=CC=NC2=CC=CC=C12.COC=1C=C2CCN(C(C2=CC1OC)C(C)C1=CC=CC=C1)CCNC(=O)NC1=CC=NC=C1 CPUNJYIDTRWYQE-UHFFFAOYSA-N 0.000 claims 1
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
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- 206010030113 Oedema Diseases 0.000 claims 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims 1
- 206010037423 Pulmonary oedema Diseases 0.000 claims 1
- 102000050488 Urotensin II Human genes 0.000 claims 1
- 108010018369 Urotensin II Proteins 0.000 claims 1
- 102000012327 Urotensin II receptors Human genes 0.000 claims 1
- 108050002984 Urotensin II receptors Proteins 0.000 claims 1
- 230000005856 abnormality Effects 0.000 claims 1
- 239000000674 adrenergic antagonist Substances 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
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- 229940126317 angiotensin II receptor antagonist Drugs 0.000 claims 1
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- 239000005557 antagonist Substances 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
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- 229940079593 drug Drugs 0.000 claims 1
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- 239000002308 endothelin receptor antagonist Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
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- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims 1
- 239000002904 solvent Chemical class 0.000 claims 1
- HFNHAPQMXICKCF-USJMABIRSA-N urotensin-ii Chemical compound N([C@@H](CC(O)=O)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@@H](C(C)C)C(O)=O)C(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](N)CCC(O)=O)[C@@H](C)O HFNHAPQMXICKCF-USJMABIRSA-N 0.000 claims 1
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| PCT/EP2002/003131 WO2002076979A1 (en) | 2001-03-27 | 2002-03-20 | 1,2,3,4-tetrahydroisoquinolines derivatives as urotensin ii receptor antagonists |
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| AT (1) | ATE300533T1 (enExample) |
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| PT1243262E (pt) | 2001-03-20 | 2006-10-31 | Sanol Arznei Schwarz Gmbh | Nova utilizacao de uma classe de compostos peptideos para o tratamento da dor inflamatoria nao neuropatica |
| DE60100055T2 (de) | 2001-03-21 | 2003-07-24 | Schwarz Pharma Ag | Neue Verwendung einer Klasse von Peptidverbindungen zur Behandlung von Allodynie oder andere Arten von chronischen oder Phantomschmerzen |
| CA2478909A1 (en) * | 2002-03-13 | 2003-09-25 | Duane D. Miller | Substituted tetrahydroisoquinoline compounds, methods of making, and their use |
| KR20050043967A (ko) * | 2002-09-17 | 2005-05-11 | 액테리온 파마슈티칼 리미티드 | 1-피리딘-4-일-요소 유도체 |
| EP1594439A2 (en) | 2003-02-13 | 2005-11-16 | Albert Einstein College Of Medicine Of Yeshiva University | REGULATION OF FOOD INTAKE AND GLUCOSE PRODUCTION BY MODULATION OF LONG-CHAIN FATTY ACYL-CoA LEVELS IN THE HYPOTHALAMUS |
| EP1631565A1 (en) * | 2003-05-07 | 2006-03-08 | Actelion Pharmaceuticals Ltd. | Piperazine-alkyl-ureido derivatives |
| CN1784394A (zh) * | 2003-05-08 | 2006-06-07 | 埃科特莱茵药品有限公司 | 新型哌啶衍生物 |
| CN1856305B (zh) * | 2003-09-26 | 2010-04-28 | 埃科特莱茵药品有限公司 | 用作尾加压素ⅱ拮抗剂的吡啶衍生物 |
| ATE428413T1 (de) | 2003-12-02 | 2009-05-15 | Sanol Arznei Schwarz Gmbh | Neue verwendung von peptidverbindungen zur behandlung ovn zentralen neuropathischen schmerzen |
| EP1604655A1 (en) | 2004-06-09 | 2005-12-14 | Schwarz Pharma Ag | Novel use of peptide compounds for treating pain in trigeminal neuralgia |
| EA014055B1 (ru) | 2004-08-27 | 2010-08-30 | Шварц Фарма Аг | Применение пептидных соединений для лечения боли при раке кости, а также боли, вызванной химиотерапией и нуклеозидами |
| CN101039930B (zh) | 2004-10-12 | 2010-08-11 | 埃科特莱茵药品有限公司 | 作为结晶硫酸盐的1-[2-(4-甲苯基-4-羟基-哌啶-1-基)-乙基]-3-(2-甲基-喹啉-4-基)-脲 |
| WO2006126255A1 (ja) * | 2005-05-24 | 2006-11-30 | Daito Chemix Corporation | Ｎ－（２－ブロモエチル）カルバミン酸ｔｅｒｔ－ブチルの製造方法 |
| TW200804347A (en) * | 2006-01-10 | 2008-01-16 | Janssen Pharmaceutica Nv | Urotensin II receptor antagonists |
| US20070196510A1 (en) * | 2006-02-17 | 2007-08-23 | Gerber Michael J | Method for treating resistant hypertension |
| WO2007144195A2 (en) | 2006-06-15 | 2007-12-21 | Schwarz Pharma Ag | Pharmaceutical composition with synergistic anticonvulsant effect |
| CL2007002097A1 (es) * | 2006-07-20 | 2008-01-18 | Smithkline Beecham Corp | Compuestos derivados de pirrolidina o morfolina antagonistas de urotensina ii; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar insuficiencia cardiaca congestiva, insuficiencia cardiaca isquemica, angina, isquemia del miocardio, vejiga hiperactiva, asma y/o copd, entre otras. |
| JP5313881B2 (ja) * | 2007-04-04 | 2013-10-09 | 興和株式会社 | テトラヒドロイソキノリン化合物 |
| ES2397764T3 (es) * | 2008-04-01 | 2013-03-11 | Abbott Gmbh & Co. Kg | Tetrahidroisoquinolinas, composiciones farmacéuticas que las contienen, y su uso en terapia |
| LT2960244T (lt) | 2008-10-31 | 2016-11-25 | Shionogi & Co., Ltd. | Cefalosporinas, turintis katecholio grupę |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| CN102378574B (zh) | 2009-03-30 | 2013-11-20 | 转化技术制药公司 | 取代的偶氮蒽衍生物、药物组合物及其使用方法 |
| US20100312480A1 (en) * | 2009-04-24 | 2010-12-09 | Hansteen Fredrik | Method for monitoring fluid flow in a multi-layered system |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8853196B2 (en) | 2011-08-05 | 2014-10-07 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| TWI537262B (zh) * | 2011-08-17 | 2016-06-11 | 美國禮來大藥廠 | 供治療糖尿病使用之新穎１，２，３，４－四氫喹啉衍生物 |
| CA2853254A1 (en) | 2011-11-18 | 2013-05-23 | Abbvie Inc. | N-substituted aminobenzocycloheptene, aminotetraline, aminoindane and phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| EP3498701B1 (en) * | 2012-12-21 | 2023-02-22 | Epizyme Inc | Prmt5 inhibitors and uses thereof |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| MX2016004936A (es) | 2013-10-17 | 2016-12-20 | Abbvie Deutschland | Derivados de aminocromano, aminotiocromano y amino-1,2,3,4-tetrahi droquinilina, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| CA2924699A1 (en) | 2013-10-17 | 2015-04-23 | AbbVie Deutschland GmbH & Co. KG | Aminotetraline and aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| JP7065951B2 (ja) | 2017-09-22 | 2022-05-12 | ジュビラント エピパッド エルエルシー | Ｐａｄ阻害剤としての複素環式化合物 |
| WO2019077631A1 (en) | 2017-10-18 | 2019-04-25 | Jubilant Biosys Limited | IMIDAZO-PYRIDINE COMPOUNDS FOR USE AS PAD INHIBITORS |
| EP3707135A1 (en) | 2017-11-06 | 2020-09-16 | Jubilant Prodel LLC | Pyrimidine derivatives as inhibitors of pd1/pd-l1 activation |
| IL274762B2 (en) | 2017-11-24 | 2023-10-01 | Jubilant Episcribe Llc | Novel heterocyclic compounds as prmt5 inhibitors |
| US11466012B2 (en) * | 2018-01-10 | 2022-10-11 | Allinky Biopharma | Tetrahydroisoquinoline compounds |
| WO2019175897A1 (en) | 2018-03-13 | 2019-09-19 | Jubilant Biosys Limited | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
| CN110755434B (zh) * | 2018-07-27 | 2022-03-15 | 中国医学科学院药物研究所 | 化合物palosuran防治骨骼肌萎缩等疾病的用途 |
| US12024521B2 (en) * | 2020-06-30 | 2024-07-02 | Prosetta Biosciences, Inc. | Isoquinoline derivatives, methods of synthesis and uses thereof |
| CN115677579B (zh) * | 2022-11-02 | 2024-05-24 | 上海药坦药物研究开发有限公司 | 四氢罂粟碱及其中间体的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI97540C (fi) | 1989-11-06 | 1997-01-10 | Sanofi Sa | Menetelmä terapeuttisesti käyttökelpoisten, aromaattisesti substituoitujen piperidiini- ja piperatsiinijohdannaisten valmistamiseksi |
| CA2061260A1 (en) | 1991-02-27 | 1992-08-28 | Kiyofumi Ishikawa | Isoquinoline derivatives |
| AUPP003197A0 (en) | 1997-09-03 | 1997-11-20 | Fujisawa Pharmaceutical Co., Ltd. | New heterocyclic compounds |
| EP1200395B1 (en) | 1999-07-28 | 2006-03-29 | Kirin Beer Kabushiki Kaisha | Urea derivatives as inhibitors of ccr-3 receptor |
| ES2225297T3 (es) | 1999-12-21 | 2005-03-16 | Smithkline Beecham Corporation | Antagonistas del receptor de urotensina ii. |
| ATE249831T1 (de) * | 1999-12-21 | 2003-10-15 | Smithkline Beecham Corp | Carboxamidderivate von pyrrolidine und piperidine als urotensin-ii rezeptorantagonisten |
| AU2441801A (en) | 1999-12-21 | 2001-07-03 | Smithkline Beecham Corporation | Urotensin-ii receptor antagonists |
| AU2001266346A1 (en) | 2000-06-28 | 2002-01-08 | Takeda Chemical Industries Ltd. | Biphenyl compound |
| WO2002002530A1 (en) | 2000-07-04 | 2002-01-10 | Takeda Chemical Industries, Ltd. | Gpr14 antagonist |
-
2002
- 2002-03-20 US US10/471,724 patent/US6815451B2/en not_active Expired - Fee Related
- 2002-03-20 DE DE60205234T patent/DE60205234T2/de not_active Expired - Fee Related
- 2002-03-20 BR BR0207715-9A patent/BR0207715A/pt not_active IP Right Cessation
- 2002-03-20 ES ES02730036T patent/ES2246399T3/es not_active Expired - Lifetime
- 2002-03-20 KR KR10-2003-7012299A patent/KR20040016844A/ko not_active Withdrawn
- 2002-03-20 AT AT02730036T patent/ATE300533T1/de not_active IP Right Cessation
- 2002-03-20 CA CA002441790A patent/CA2441790A1/en not_active Abandoned
- 2002-03-20 MX MXPA03008639A patent/MXPA03008639A/es active IP Right Grant
- 2002-03-20 CN CNB028059417A patent/CN1288148C/zh not_active Expired - Fee Related
- 2002-03-20 IL IL15709302A patent/IL157093A0/xx unknown
- 2002-03-20 EP EP02730036A patent/EP1379523B1/en not_active Expired - Lifetime
- 2002-03-20 JP JP2002576237A patent/JP2004529132A/ja not_active Abandoned
- 2002-03-20 HU HU0402508A patent/HUP0402508A2/hu unknown
- 2002-03-20 NZ NZ527276A patent/NZ527276A/en unknown
- 2002-03-20 WO PCT/EP2002/003131 patent/WO2002076979A1/en not_active Ceased
-
2003
- 2003-09-23 NO NO20034230A patent/NO20034230D0/no not_active Application Discontinuation
-
2004
- 2004-07-13 US US10/889,182 patent/US20040242564A1/en not_active Abandoned
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