UA77042C2 - Substituted 4-tetrahydroquinolines, use thereof as medicament, a medicament containing them - Google Patents
Substituted 4-tetrahydroquinolines, use thereof as medicament, a medicament containing them Download PDFInfo
- Publication number
- UA77042C2 UA77042C2 UA20040705310A UA20040705310A UA77042C2 UA 77042 C2 UA77042 C2 UA 77042C2 UA 20040705310 A UA20040705310 A UA 20040705310A UA 20040705310 A UA20040705310 A UA 20040705310A UA 77042 C2 UA77042 C2 UA 77042C2
- Authority
- UA
- Ukraine
- Prior art keywords
- methyl
- dichloro
- tetrahydroisoquinolin
- atoms
- uphenyl
- Prior art date
Links
- 239000003814 drug Substances 0.000 title abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 166
- 238000011282 treatment Methods 0.000 claims abstract description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 230000002265 prevention Effects 0.000 claims abstract description 19
- 201000010099 disease Diseases 0.000 claims abstract description 15
- 230000006378 damage Effects 0.000 claims abstract description 8
- 210000000056 organ Anatomy 0.000 claims abstract description 8
- 230000035939 shock Effects 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 279
- -1 K12 radical Chemical class 0.000 claims description 168
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 152
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 124
- 125000004437 phosphorous atom Chemical group 0.000 claims description 119
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 113
- 229910052757 nitrogen Inorganic materials 0.000 claims description 107
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 76
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 62
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 60
- 150000001408 amides Chemical class 0.000 claims description 55
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 51
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 51
- 239000004202 carbamide Substances 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 43
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 42
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 41
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 41
- 230000007958 sleep Effects 0.000 claims description 39
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 38
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 37
- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 35
- 150000003254 radicals Chemical class 0.000 claims description 34
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 32
- 229940080818 propionamide Drugs 0.000 claims description 32
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims description 31
- KNWWGBNAUNTSRV-UHFFFAOYSA-N 4-methylpiperazine-1-carboxylic acid Chemical compound CN1CCN(C(O)=O)CC1 KNWWGBNAUNTSRV-UHFFFAOYSA-N 0.000 claims description 30
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 30
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 229910052796 boron Inorganic materials 0.000 claims description 25
- 229940126601 medicinal product Drugs 0.000 claims description 25
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 claims description 24
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 24
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims description 24
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 claims description 24
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 23
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 23
- WFCLWJHOKCQYOQ-UHFFFAOYSA-N 1-acetylpiperidine-4-carboxylic acid Chemical compound CC(=O)N1CCC(C(O)=O)CC1 WFCLWJHOKCQYOQ-UHFFFAOYSA-N 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 22
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 21
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 20
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 19
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 18
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 18
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 17
- SUGDSKDKCOFIQN-UHFFFAOYSA-N 1-methylsulfonylpiperidine-4-carboxylic acid Chemical compound CS(=O)(=O)N1CCC(C(O)=O)CC1 SUGDSKDKCOFIQN-UHFFFAOYSA-N 0.000 claims description 16
- IMBBXSASDSZJSX-UHFFFAOYSA-N 4-Carboxypyrazole Chemical compound OC(=O)C=1C=NNC=1 IMBBXSASDSZJSX-UHFFFAOYSA-N 0.000 claims description 16
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 16
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 claims description 16
- HCKNAJXCHMACDN-UHFFFAOYSA-N 1-methylpiperidine-4-carboxylic acid Chemical compound CN1CCC(C(O)=O)CC1 HCKNAJXCHMACDN-UHFFFAOYSA-N 0.000 claims description 15
- ZPXGMXNPRXENML-UHFFFAOYSA-N 5-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-2-hydroxybenzoic acid Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(O)C(C(O)=O)=C1 ZPXGMXNPRXENML-UHFFFAOYSA-N 0.000 claims description 15
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000002883 imidazolyl group Chemical group 0.000 claims description 15
- 125000002971 oxazolyl group Chemical group 0.000 claims description 15
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 15
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 15
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 15
- 125000000335 thiazolyl group Chemical group 0.000 claims description 15
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 14
- ROCHTQWNNZUYOK-UHFFFAOYSA-N 3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzoic acid Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(C(O)=O)=C1 ROCHTQWNNZUYOK-UHFFFAOYSA-N 0.000 claims description 14
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 14
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 14
- 125000003386 piperidinyl group Chemical group 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000001425 triazolyl group Chemical group 0.000 claims description 14
- OGVXGNOUQNLCAU-UHFFFAOYSA-N 4-(4-bromophenyl)-6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(Br)C=C1 OGVXGNOUQNLCAU-UHFFFAOYSA-N 0.000 claims description 13
- 229940057054 1,3-dimethylurea Drugs 0.000 claims description 12
- NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical compound OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 claims description 12
- IOOWDXMXZBYKLR-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole-4-carboxylic acid Chemical compound CC1=NNC(C)=C1C(O)=O IOOWDXMXZBYKLR-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229960003966 nicotinamide Drugs 0.000 claims description 12
- 235000005152 nicotinamide Nutrition 0.000 claims description 12
- 239000011570 nicotinamide Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- LUVXGUJFNMUWEZ-UHFFFAOYSA-N 1,2-dimethylimidazole-4-sulfonic acid Chemical compound CC1=NC(S(O)(=O)=O)=CN1C LUVXGUJFNMUWEZ-UHFFFAOYSA-N 0.000 claims description 11
- QETVYTNAHZLDNS-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzenesulfonamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(S(N)(=O)=O)C=C1 QETVYTNAHZLDNS-UHFFFAOYSA-N 0.000 claims description 10
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- ITSVCLWKVUKMHH-UHFFFAOYSA-N 3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)aniline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(N)=C1 ITSVCLWKVUKMHH-UHFFFAOYSA-N 0.000 claims description 9
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 9
- XGMDYIYCKWMWLY-UHFFFAOYSA-N 2,2,2-trifluoroethanesulfonic acid Chemical compound OS(=O)(=O)CC(F)(F)F XGMDYIYCKWMWLY-UHFFFAOYSA-N 0.000 claims description 8
- VDVWTJFVFQVCFN-UHFFFAOYSA-N 2,5-dimethyl-1h-pyrrole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=C(C)N1 VDVWTJFVFQVCFN-UHFFFAOYSA-N 0.000 claims description 8
- WLQPUTXHTCZSFK-UHFFFAOYSA-N 5-bromothiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)S1 WLQPUTXHTCZSFK-UHFFFAOYSA-N 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 8
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- SELDCFUFDZPRLP-UHFFFAOYSA-N 1,4-dimethylpyrrole-2-carboxylic acid Chemical compound CC=1C=C(C(O)=O)N(C)C=1 SELDCFUFDZPRLP-UHFFFAOYSA-N 0.000 claims description 7
- CHHASAIQKXOAOX-UHFFFAOYSA-N 1-(2,2-dimethylpropoxy)-2,2-dimethylpropane Chemical compound CC(C)(C)COCC(C)(C)C CHHASAIQKXOAOX-UHFFFAOYSA-N 0.000 claims description 7
- OOPDWMLXBWNOLH-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzoic acid Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(C(O)=O)C=C1 OOPDWMLXBWNOLH-UHFFFAOYSA-N 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 7
- 230000000302 ischemic effect Effects 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- UNNPAFDYRLETBW-UHFFFAOYSA-N 3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzenesulfonamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(S(N)(=O)=O)=C1 UNNPAFDYRLETBW-UHFFFAOYSA-N 0.000 claims description 6
- JTXNWYHSDXNOAG-UHFFFAOYSA-N 4-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]morpholine Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1N1CCOCC1 JTXNWYHSDXNOAG-UHFFFAOYSA-N 0.000 claims description 6
- WOSRCHOJUSCXJV-UHFFFAOYSA-N 6,8-dichloro-2-cyclopropyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C2CC2)CC1C1=CC=CC=C1 WOSRCHOJUSCXJV-UHFFFAOYSA-N 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- XMYPFIYRTAOIFI-UHFFFAOYSA-N 2-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)aniline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC=C1N XMYPFIYRTAOIFI-UHFFFAOYSA-N 0.000 claims description 5
- ATZPMMXKZFAFOP-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)aniline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(N)C=C1 ATZPMMXKZFAFOP-UHFFFAOYSA-N 0.000 claims description 5
- SNWGRRCTCGASCN-UHFFFAOYSA-N 4-nitro-1h-pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CN1 SNWGRRCTCGASCN-UHFFFAOYSA-N 0.000 claims description 5
- XSGVEJDBLQQXST-UHFFFAOYSA-N 5-chloro-1,3-dimethylpyrazole-4-sulfonic acid Chemical class CC1=NN(C)C(Cl)=C1S(O)(=O)=O XSGVEJDBLQQXST-UHFFFAOYSA-N 0.000 claims description 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 150000004702 methyl esters Chemical class 0.000 claims description 5
- HWHOOFAFSRSPOT-UHFFFAOYSA-N 2-chloro-5-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzenesulfonamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(Cl)C(S(N)(=O)=O)=C1 HWHOOFAFSRSPOT-UHFFFAOYSA-N 0.000 claims description 4
- LJCWTVCXFOSCRP-UHFFFAOYSA-N 4-(3-bromophenyl)-6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(Br)=C1 LJCWTVCXFOSCRP-UHFFFAOYSA-N 0.000 claims description 4
- BYEHLECXGQISFM-UHFFFAOYSA-N 6,8-dichloro-2-methyl-4-(4-pyrrolidin-1-ylphenyl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1N1CCCC1 BYEHLECXGQISFM-UHFFFAOYSA-N 0.000 claims description 4
- SHBPZIGBKLSQFG-UHFFFAOYSA-N 6,8-dichloro-2-methyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC=C1 SHBPZIGBKLSQFG-UHFFFAOYSA-N 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 230000004663 cell proliferation Effects 0.000 claims description 4
- 230000002093 peripheral effect Effects 0.000 claims description 4
- 230000000241 respiratory effect Effects 0.000 claims description 4
- 230000029058 respiratory gaseous exchange Effects 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 206010041235 Snoring Diseases 0.000 claims description 3
- 201000011040 acute kidney failure Diseases 0.000 claims description 3
- 208000020832 chronic kidney disease Diseases 0.000 claims description 3
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 230000004060 metabolic process Effects 0.000 claims description 3
- 201000002859 sleep apnea Diseases 0.000 claims description 3
- ZTWFDFFSPSWCEP-UHFFFAOYSA-N 2,4-dimethyl-4-phenyl-1,3-dihydroisoquinoline Chemical compound C1N(C)CC2=CC=CC=C2C1(C)C1=CC=CC=C1 ZTWFDFFSPSWCEP-UHFFFAOYSA-N 0.000 claims description 2
- ZBINDVNASLJSJF-UHFFFAOYSA-N 2,6-dimethyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(C)=CC=C2CN(C)CC1C1=CC=CC=C1 ZBINDVNASLJSJF-UHFFFAOYSA-N 0.000 claims description 2
- SUYOCKAQLJWIGF-UHFFFAOYSA-N 2,8-dimethyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC(C)=C2CN(C)CC1C1=CC=CC=C1 SUYOCKAQLJWIGF-UHFFFAOYSA-N 0.000 claims description 2
- SCROJUWBHGENKF-UHFFFAOYSA-N 2-butyl-4-phenyl-3,4-dihydro-1h-isoquinolin-8-amine Chemical compound C12=CC=CC(N)=C2CN(CCCC)CC1C1=CC=CC=C1 SCROJUWBHGENKF-UHFFFAOYSA-N 0.000 claims description 2
- QKUVNSGJPHVOHY-UHFFFAOYSA-N 2-ethyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(CC)CC1C1=CC=CC=C1 QKUVNSGJPHVOHY-UHFFFAOYSA-N 0.000 claims description 2
- NNVATDBGKYTMIL-UHFFFAOYSA-N 2-methyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC=C2CN(C)CC1C1=CC=CC=C1 NNVATDBGKYTMIL-UHFFFAOYSA-N 0.000 claims description 2
- ZZYPDSKOTDXNJI-UHFFFAOYSA-N 2-methyl-8-nitro-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC=CC([N+]([O-])=O)=C2CN(C)CC1C1=CC=CC=C1 ZZYPDSKOTDXNJI-UHFFFAOYSA-N 0.000 claims description 2
- WALQZRTZISWWJK-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-methyl-3,4-dihydro-1h-isoquinolin-8-amine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=C(Cl)C=C1Cl WALQZRTZISWWJK-UHFFFAOYSA-N 0.000 claims description 2
- IRZHQDDIUQJKJQ-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-methyl-3,4-dihydro-1h-isoquinolin-8-amine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=C(Cl)C(Cl)=C1 IRZHQDDIUQJKJQ-UHFFFAOYSA-N 0.000 claims description 2
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- 159000000000 sodium salts Chemical class 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/10—Laxatives
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Gastroenterology & Hepatology (AREA)
- Nutrition Science (AREA)
- Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10159714 | 2001-12-05 | ||
| PCT/EP2002/012990 WO2003048129A1 (de) | 2001-12-05 | 2002-11-20 | Substituierte 4-phenyltetrahydroisochinoline, verfahren zu ihrer herstellung, ihre verwendung als medikament, sowie sie enthaltendes medikament |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA77042C2 true UA77042C2 (en) | 2006-10-16 |
Family
ID=7708117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040705310A UA77042C2 (en) | 2001-12-05 | 2002-11-20 | Substituted 4-tetrahydroquinolines, use thereof as medicament, a medicament containing them |
Country Status (34)
| Country | Link |
|---|---|
| EP (1) | EP1453810B1 (sr) |
| JP (1) | JP4510457B2 (sr) |
| KR (1) | KR20050044724A (sr) |
| CN (1) | CN100497314C (sr) |
| AR (1) | AR037620A1 (sr) |
| AT (1) | ATE425968T1 (sr) |
| AU (1) | AU2002356689B2 (sr) |
| BR (1) | BR0214753A (sr) |
| CA (1) | CA2469385A1 (sr) |
| CO (1) | CO5580748A2 (sr) |
| DE (1) | DE50213372D1 (sr) |
| DK (1) | DK1453810T3 (sr) |
| EC (1) | ECSP045138A (sr) |
| ES (1) | ES2324528T3 (sr) |
| HK (1) | HK1072597A1 (sr) |
| HR (1) | HRP20040507A2 (sr) |
| HU (1) | HUP0600854A2 (sr) |
| IL (1) | IL162316A0 (sr) |
| MA (1) | MA27147A1 (sr) |
| MX (1) | MXPA04005343A (sr) |
| MY (1) | MY157371A (sr) |
| NO (1) | NO326650B1 (sr) |
| NZ (1) | NZ533322A (sr) |
| OA (1) | OA12740A (sr) |
| PE (1) | PE20030726A1 (sr) |
| PL (1) | PL369313A1 (sr) |
| PT (1) | PT1453810E (sr) |
| RS (1) | RS48004A (sr) |
| RU (1) | RU2298003C2 (sr) |
| TN (1) | TNSN04100A1 (sr) |
| TW (1) | TWI281860B (sr) |
| UA (1) | UA77042C2 (sr) |
| WO (1) | WO2003048129A1 (sr) |
| ZA (1) | ZA200403711B (sr) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10312963A1 (de) * | 2003-03-24 | 2004-10-07 | Aventis Pharma Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| TW200526626A (en) | 2003-09-13 | 2005-08-16 | Astrazeneca Ab | Chemical compounds |
| DE102004046492A1 (de) * | 2004-09-23 | 2006-03-30 | Sanofi-Aventis Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| US20060111393A1 (en) * | 2004-11-22 | 2006-05-25 | Molino Bruce F | 4-Phenyl substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin |
| DE102005001411A1 (de) * | 2005-01-12 | 2006-07-27 | Sanofi-Aventis Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| BRPI0607756A2 (pt) | 2005-02-18 | 2010-05-18 | Astrazeneca Ab | composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, método para inibição de dna girase bacteriana e/ou topoisomerase iv em um animal de sangue quente, uso de um composto ou um sal farmaceuticamente aceitável do mesmo, e, processo para preparar compostos ou sais farmaceuticamente aceitáveis dos mesmos |
| US20080269214A1 (en) * | 2005-03-04 | 2008-10-30 | Astrazeneca Ab | Pyrrole Derivatives as Dna Gyrase and Topoisomerase Inhibitors |
| DE102005044817A1 (de) * | 2005-09-20 | 2007-03-22 | Sanofi-Aventis Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| DE102006012545A1 (de) | 2006-03-18 | 2007-09-27 | Sanofi-Aventis | Substituierte 2-Amino-4-phenyl-dihydrochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| WO2018129556A1 (en) * | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| WO2010078449A2 (en) * | 2008-12-31 | 2010-07-08 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| US10543207B2 (en) | 2008-12-31 | 2020-01-28 | Ardelyx, Inc. | Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| KR20120034644A (ko) | 2009-05-12 | 2012-04-12 | 알바니 몰레큘라 리써치, 인크. | 아릴, 헤테로아릴, 및 헤테로사이클 치환된 테트라하이드로이소퀴놀린 및 이의 용도 |
| CA2880432C (en) * | 2012-08-21 | 2023-03-14 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| HUE044550T2 (hu) | 2013-04-12 | 2019-11-28 | Ardelyx Inc | NHE-3 megkötõ vegyületek és foszfát transzport gátlási módszerek |
| CN103788084A (zh) * | 2014-03-02 | 2014-05-14 | 湖南华腾制药有限公司 | 四氢异喹啉衍生物及其合成方法 |
| CN106536502B (zh) * | 2014-07-25 | 2019-03-05 | 大正制药株式会社 | 被杂芳基取代的苯基四氢异喹啉化合物 |
| JP6903923B2 (ja) * | 2016-01-22 | 2021-07-14 | 大正製薬株式会社 | ヘテロアリールで置換されたフェニルテトラヒドロイソキノリン化合物を有効成分として含有する医薬 |
| CN110267944B (zh) | 2017-01-09 | 2024-03-08 | 阿德利克斯股份有限公司 | 可用于治疗胃肠道病症的化合物 |
| JP2020505333A (ja) | 2017-01-09 | 2020-02-20 | アルデリックス， インコーポレイテッド | Ｎｈｅ媒介性アンチポートの阻害薬 |
| IL303799A (en) * | 2020-12-18 | 2023-08-01 | Shanghai Jemincare Pharmaceutical Co Ltd | TETRAHYDROISOQUINOLINE COMPOUND IN SUBSTITUTE BENZOHETROCYCLE |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19951702A1 (de) * | 1999-10-27 | 2001-05-03 | Aventis Pharma Gmbh | Verwendung von 2-Amino-3,4-dihydro-chinazolinen zur Herstellung eines Medikaments zur Behandlung oder Prophylaxe von durch ischämischen Zuständen bewirkten Krankheiten |
| ES2304984T3 (es) * | 1999-11-03 | 2008-11-01 | Amr Technology, Inc. | Tetra-hidroisoquinolinas de sustitucion arilica y heteroarilica y su utilizacion para bloquear la recaptacion de norepinefrina, dopamina y serotonina. |
| AU784280B2 (en) * | 1999-11-03 | 2006-03-02 | Albany Molecular Research, Inc. | 4-phenyl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin |
| EP1113007A1 (en) * | 1999-12-24 | 2001-07-04 | Pfizer Inc. | Tetrahydroisoquinoline compounds as estrogen agonists/antagonists |
| DE10019062A1 (de) * | 2000-04-18 | 2001-10-25 | Merck Patent Gmbh | 2-Guanidino-4-aryl-chinazoline als NHE-3 Inhibitoren |
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2002
- 2002-11-20 PL PL02369313A patent/PL369313A1/xx not_active Application Discontinuation
- 2002-11-20 RS YU48004A patent/RS48004A/sr unknown
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- 2002-11-20 IL IL16231602A patent/IL162316A0/xx unknown
- 2002-11-20 CN CNB028278879A patent/CN100497314C/zh not_active Expired - Fee Related
- 2002-11-20 AT AT02804183T patent/ATE425968T1/de not_active IP Right Cessation
- 2002-11-20 PT PT02804183T patent/PT1453810E/pt unknown
- 2002-11-20 EP EP02804183A patent/EP1453810B1/de not_active Expired - Lifetime
- 2002-11-20 HU HU0600854A patent/HUP0600854A2/hu unknown
- 2002-11-20 OA OA1200400166A patent/OA12740A/en unknown
- 2002-11-20 CA CA002469385A patent/CA2469385A1/en not_active Abandoned
- 2002-11-20 AU AU2002356689A patent/AU2002356689B2/en not_active Ceased
- 2002-11-20 DE DE50213372T patent/DE50213372D1/de not_active Expired - Lifetime
- 2002-11-20 UA UA20040705310A patent/UA77042C2/uk unknown
- 2002-11-20 WO PCT/EP2002/012990 patent/WO2003048129A1/de active Application Filing
- 2002-11-20 RU RU2004120295/04A patent/RU2298003C2/ru not_active IP Right Cessation
- 2002-11-20 ES ES02804183T patent/ES2324528T3/es not_active Expired - Lifetime
- 2002-11-20 DK DK02804183T patent/DK1453810T3/da active
- 2002-11-20 MX MXPA04005343A patent/MXPA04005343A/es active IP Right Grant
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- 2002-11-20 JP JP2003549321A patent/JP4510457B2/ja not_active Expired - Fee Related
- 2002-11-26 PE PE2002001138A patent/PE20030726A1/es not_active Application Discontinuation
- 2002-12-03 TW TW091134977A patent/TWI281860B/zh not_active IP Right Cessation
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2004
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- 2004-05-25 NO NO20042158A patent/NO326650B1/no not_active IP Right Cessation
- 2004-06-03 CO CO04052088A patent/CO5580748A2/es not_active Application Discontinuation
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2005
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