MXPA03008639A - Derivados de 1,2,3,4-tetrahidroisoquinolinas. - Google Patents
Derivados de 1,2,3,4-tetrahidroisoquinolinas.Info
- Publication number
- MXPA03008639A MXPA03008639A MXPA03008639A MXPA03008639A MXPA03008639A MX PA03008639 A MXPA03008639 A MX PA03008639A MX PA03008639 A MXPA03008639 A MX PA03008639A MX PA03008639 A MXPA03008639 A MX PA03008639A MX PA03008639 A MXPA03008639 A MX PA03008639A
- Authority
- MX
- Mexico
- Prior art keywords
- dimethoxy
- ethyl
- dihydro
- urea
- isoquinolin
- Prior art date
Links
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 108050002984 Urotensin II receptors Proteins 0.000 title claims description 10
- 102000012327 Urotensin II receptors Human genes 0.000 title claims description 10
- 239000002464 receptor antagonist Substances 0.000 title description 6
- 229940044551 receptor antagonist Drugs 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 137
- 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 abstract description 33
- 108010018369 Urotensin II Proteins 0.000 claims abstract description 32
- 102000050488 Urotensin II Human genes 0.000 claims abstract description 32
- 239000005557 antagonist Substances 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 239000004202 carbamide Substances 0.000 claims description 136
- -1 naphthalene-1-yl Chemical group 0.000 claims description 133
- 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 description 55
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 12
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 9
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000002904 solvent Chemical class 0.000 claims description 7
- 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 description 6
- 208000006673 asthma Diseases 0.000 claims description 6
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- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 5
- 206010012289 Dementia Diseases 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 230000002792 vascular Effects 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
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- 206010020772 Hypertension Diseases 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 4
- 210000000056 organ Anatomy 0.000 claims description 4
- JJOCORBINXKKOT-UHFFFAOYSA-N quinolin-4-ylcarbamic acid Chemical compound C1=CC=C2C(NC(=O)O)=CC=NC2=C1 JJOCORBINXKKOT-UHFFFAOYSA-N 0.000 claims description 4
- 102000005962 receptors Human genes 0.000 claims description 4
- 108020003175 receptors Proteins 0.000 claims description 4
- 125000005504 styryl group Chemical group 0.000 claims description 4
- WRAIHDHZUDJXLN-UHFFFAOYSA-N 2-[1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]ethylurea Chemical compound FC1=CC=C(CC2N(CCC3=CC(=C(C=C23)OC)OC)CCNC(=O)N)C=C1 WRAIHDHZUDJXLN-UHFFFAOYSA-N 0.000 claims description 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 description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 200000000007 Arterial disease Diseases 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 201000004569 Blindness Diseases 0.000 claims description 3
- 201000006474 Brain Ischemia Diseases 0.000 claims description 3
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010010904 Convulsion Diseases 0.000 claims description 3
- 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 description 3
- 108010036949 Cyclosporine Proteins 0.000 claims description 3
- 206010011878 Deafness Diseases 0.000 claims description 3
- 206010012335 Dependence Diseases 0.000 claims description 3
- 208000002249 Diabetes Complications Diseases 0.000 claims description 3
- 206010012655 Diabetic complications Diseases 0.000 claims description 3
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 3
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 3
- 208000002193 Pain Diseases 0.000 claims description 3
- 206010037423 Pulmonary oedema Diseases 0.000 claims description 3
- 208000003782 Raynaud disease Diseases 0.000 claims description 3
- 208000012322 Raynaud phenomenon Diseases 0.000 claims description 3
- 208000001647 Renal Insufficiency Diseases 0.000 claims description 3
- 206010038419 Renal colic Diseases 0.000 claims description 3
- 206010063897 Renal ischaemia Diseases 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 claims description 3
- 206010001902 amaurosis Diseases 0.000 claims description 3
- 238000002399 angioplasty Methods 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 206010003119 arrhythmia Diseases 0.000 claims description 3
- 206010006451 bronchitis Diseases 0.000 claims description 3
- 238000007675 cardiac surgery Methods 0.000 claims description 3
- 206010008118 cerebral infarction Diseases 0.000 claims description 3
- 208000007451 chronic bronchitis Diseases 0.000 claims description 3
- 208000020832 chronic kidney disease Diseases 0.000 claims description 3
- 229960001265 ciclosporin Drugs 0.000 claims description 3
- 230000010370 hearing loss Effects 0.000 claims description 3
- 231100000888 hearing loss Toxicity 0.000 claims description 3
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- 201000001881 impotence Diseases 0.000 claims description 3
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- 230000000877 morphologic effect Effects 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
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- 208000005333 pulmonary edema Diseases 0.000 claims description 3
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 3
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 208000013223 septicemia Diseases 0.000 claims description 3
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- 230000006016 thyroid dysfunction Effects 0.000 claims description 3
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- 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 description 2
- 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 description 2
- 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 description 2
- DSWDMGXSJASKJF-UHFFFAOYSA-N 1-[2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7,8-trimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-quinolin-4-ylurea Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=C(OC)C(OC)=C(OC)C=C2CCN1CCNC(=O)NC1=CC=NC2=CC=CC=C12 DSWDMGXSJASKJF-UHFFFAOYSA-N 0.000 claims description 2
- VJYPCWGHWWMOMC-UHFFFAOYSA-N 1-[2-[1-[(3,4-dimethoxyphenyl)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(OC)=C1 VJYPCWGHWWMOMC-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- MQCIVCWSROTVHN-UHFFFAOYSA-N 1-[2-[6,7-dimethoxy-1-(1-phenylpropyl)-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-3-pyridin-4-ylurea Chemical compound C=1C=CC=CC=1C(CC)C(C1=CC(OC)=C(OC)C=C1CC1)N1CCNC(=O)NC1=CC=NC=C1 MQCIVCWSROTVHN-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- UTGYUSGELCNAIM-UHFFFAOYSA-N 1-[3-[1-[(3,4-difluorophenyl)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(F)=C1 UTGYUSGELCNAIM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
- 229940118365 Endothelin receptor antagonist Drugs 0.000 claims description 2
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004321 azepin-2-yl group Chemical group [H]N1C([H])=C([H])C([H])=C([H])C([H])=C1* 0.000 claims description 2
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- 229910052760 oxygen Inorganic materials 0.000 claims description 2
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- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 2
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- ICJVRPQWEPOSOL-UHFFFAOYSA-N pyridin-4-ylurea Chemical compound NC(=O)NC1=CC=NC=C1 ICJVRPQWEPOSOL-UHFFFAOYSA-N 0.000 claims description 2
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- ATFLTLDVBOARQX-UHFFFAOYSA-N 1-[2-(1-benzyl-5,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-3-pyridin-4-ylurea Chemical compound C=1C=NC=CC=1NC(=O)NCCN1CCC=2C(OC)=CC=C(OC)C=2C1CC1=CC=CC=C1 ATFLTLDVBOARQX-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
- ZHRRVNQMIWYGDS-UHFFFAOYSA-N 1-[2-[1-[(3-fluoro-4-methoxyphenyl)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(F)=C1 ZHRRVNQMIWYGDS-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
- 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
- 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
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- 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
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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- Biomedical Technology (AREA)
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- Diabetes (AREA)
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- Urology & Nephrology (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP0103422 | 2001-03-27 | ||
| EP0109845 | 2001-08-27 | ||
| PCT/EP2002/003131 WO2002076979A1 (en) | 2001-03-27 | 2002-03-20 | 1,2,3,4-tetrahydroisoquinolines derivatives as urotensin ii receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA03008639A true MXPA03008639A (es) | 2005-03-07 |
Family
ID=29421788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA03008639A MXPA03008639A (es) | 2001-03-27 | 2002-03-20 | Derivados de 1,2,3,4-tetrahidroisoquinolinas. |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6815451B2 (enExample) |
| EP (1) | EP1379523B1 (enExample) |
| JP (1) | JP2004529132A (enExample) |
| KR (1) | KR20040016844A (enExample) |
| CN (1) | CN1288148C (enExample) |
| AT (1) | ATE300533T1 (enExample) |
| BR (1) | BR0207715A (enExample) |
| CA (1) | CA2441790A1 (enExample) |
| DE (1) | DE60205234T2 (enExample) |
| ES (1) | ES2246399T3 (enExample) |
| HU (1) | HUP0402508A2 (enExample) |
| IL (1) | IL157093A0 (enExample) |
| MX (1) | MXPA03008639A (enExample) |
| NO (1) | NO20034230D0 (enExample) |
| NZ (1) | NZ527276A (enExample) |
| WO (1) | WO2002076979A1 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (9)
| 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
Also Published As
| Publication number | Publication date |
|---|---|
| US20040242564A1 (en) | 2004-12-02 |
| US6815451B2 (en) | 2004-11-09 |
| HUP0402508A2 (hu) | 2005-03-29 |
| IL157093A0 (en) | 2004-02-08 |
| CN1494542A (zh) | 2004-05-05 |
| CA2441790A1 (en) | 2002-10-03 |
| WO2002076979A8 (en) | 2003-11-06 |
| NO20034230L (no) | 2003-09-23 |
| NZ527276A (en) | 2004-11-26 |
| BR0207715A (pt) | 2004-03-23 |
| EP1379523B1 (en) | 2005-07-27 |
| EP1379523A1 (en) | 2004-01-14 |
| ATE300533T1 (de) | 2005-08-15 |
| DE60205234D1 (de) | 2005-09-01 |
| WO2002076979A1 (en) | 2002-10-03 |
| US20040110744A1 (en) | 2004-06-10 |
| JP2004529132A (ja) | 2004-09-24 |
| KR20040016844A (ko) | 2004-02-25 |
| NO20034230D0 (no) | 2003-09-23 |
| CN1288148C (zh) | 2006-12-06 |
| ES2246399T3 (es) | 2006-02-16 |
| DE60205234T2 (de) | 2006-05-24 |
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