SU1561823A3 - Способ получени производных циклического амина или их кислотно-аддитивных солей - Google Patents
Способ получени производных циклического амина или их кислотно-аддитивных солей Download PDFInfo
- Publication number
- SU1561823A3 SU1561823A3 SU884355736A SU4355736A SU1561823A3 SU 1561823 A3 SU1561823 A3 SU 1561823A3 SU 884355736 A SU884355736 A SU 884355736A SU 4355736 A SU4355736 A SU 4355736A SU 1561823 A3 SU1561823 A3 SU 1561823A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- oxo
- tetrahydro
- found
- group
- Prior art date
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- -1 derivatives of cyclic amine Chemical class 0.000 title claims abstract description 88
- 150000003839 salts Chemical class 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 4
- 239000000654 additive Substances 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 25
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 11
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 6
- 125000005605 benzo group Chemical group 0.000 claims abstract description 5
- 125000002541 furyl group Chemical group 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims abstract description 3
- 125000006239 protecting group Chemical group 0.000 claims abstract 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims abstract 2
- 230000010933 acylation Effects 0.000 claims abstract 2
- 238000005917 acylation reaction Methods 0.000 claims abstract 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 125000001041 indolyl group Chemical group 0.000 claims abstract 2
- 230000000269 nucleophilic effect Effects 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 241001331845 Equus asinus x caballus Species 0.000 claims 1
- 239000013256 coordination polymer Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 150000001721 carbon Chemical class 0.000 abstract description 2
- 125000005956 isoquinolyl group Chemical group 0.000 abstract description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 107
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 42
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 39
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 13
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 13
- 125000005936 piperidyl group Chemical group 0.000 description 13
- 125000005999 2-bromoethyl group Chemical group 0.000 description 12
- MQKFSXLBPPCAGR-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydro-2h-isoquinolin-1-one Chemical compound C1CNC(=O)C2=C1C=C(OC)C(OC)=C2 MQKFSXLBPPCAGR-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 11
- 229910001868 water Inorganic materials 0.000 description 11
- JPVUTECGMCLYRL-UHFFFAOYSA-N 2h-3-benzazepine Chemical compound C1=NCC=C2C=CC=CC2=C1 JPVUTECGMCLYRL-UHFFFAOYSA-N 0.000 description 10
- CKQQMPJQZXIYMJ-UHFFFAOYSA-N dihydrate;dihydrochloride Chemical compound O.O.Cl.Cl CKQQMPJQZXIYMJ-UHFFFAOYSA-N 0.000 description 10
- 150000004800 hydroisoquinoline derivatives Chemical class 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 7
- VJMMQXGTLJIMBF-UHFFFAOYSA-N CC1C(NCCC2=C1C=C(C(=C2)OC)OC)=O Chemical compound CC1C(NCCC2=C1C=C(C(=C2)OC)OC)=O VJMMQXGTLJIMBF-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- MWVMYAWMFTVYED-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC=CC=C21 MWVMYAWMFTVYED-UHFFFAOYSA-N 0.000 description 5
- YWPMKTWUFVOFPL-UHFFFAOYSA-N 3,4-dihydro-2h-isoquinolin-1-one Chemical compound C1=CC=C2C(=O)NCCC2=C1 YWPMKTWUFVOFPL-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000004682 monohydrates Chemical class 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- WNLPAQFDNAVWLM-UHFFFAOYSA-N 2-(2-bromoethyl)-6-methoxynaphthalene Chemical compound C1=C(CCBr)C=CC2=CC(OC)=CC=C21 WNLPAQFDNAVWLM-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- ZWTYJECJAVZKCP-UHFFFAOYSA-N 6-(3-chloropropoxy)-1,2-dimethoxynaphthalene Chemical compound C1=C(OCCCCl)C=CC2=C(OC)C(OC)=CC=C21 ZWTYJECJAVZKCP-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229940086542 triethylamine Drugs 0.000 description 4
- STBYRSZXHDPASK-UHFFFAOYSA-N 1-(chloromethyl)-2-methylnaphthalene Chemical compound C1=CC=CC2=C(CCl)C(C)=CC=C21 STBYRSZXHDPASK-UHFFFAOYSA-N 0.000 description 3
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 3
- ILNORVYPALJEIR-UHFFFAOYSA-N 2-(3-chloropropoxy)-6-methoxynaphthalene Chemical compound C1=C(OCCCCl)C=CC2=CC(OC)=CC=C21 ILNORVYPALJEIR-UHFFFAOYSA-N 0.000 description 3
- UUBMEXYWOOFYLX-UHFFFAOYSA-N 2-ethyl-6,7-dimethoxy-3,4-dihydroisoquinolin-1-one Chemical compound COC1=C(OC)C=C2C(=O)N(CC)CCC2=C1 UUBMEXYWOOFYLX-UHFFFAOYSA-N 0.000 description 3
- HIBYPMTYUSTJDC-UHFFFAOYSA-N 3-(1h-indol-3-yl)propyl benzenesulfonate Chemical compound C=1NC2=CC=CC=C2C=1CCCOS(=O)(=O)C1=CC=CC=C1 HIBYPMTYUSTJDC-UHFFFAOYSA-N 0.000 description 3
- LTAGXVMHLFYRNK-UHFFFAOYSA-N 4-(2-bromoethyl)-1,2-dimethoxybenzene Chemical compound COC1=CC=C(CCBr)C=C1OC LTAGXVMHLFYRNK-UHFFFAOYSA-N 0.000 description 3
- DYMLFDZJSPKPHA-UHFFFAOYSA-N 5-(3-chloropropoxy)-1,3-benzodioxole Chemical compound ClCCCOC1=CC=C2OCOC2=C1 DYMLFDZJSPKPHA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- JFGRUDGEXXULMZ-UHFFFAOYSA-N C1CNC(=O)C(OC)(OC)C2=CC=CC=C21 Chemical compound C1CNC(=O)C(OC)(OC)C2=CC=CC=C21 JFGRUDGEXXULMZ-UHFFFAOYSA-N 0.000 description 3
- DCGIEIRGPBYBHD-UHFFFAOYSA-N Cl.C1=NCC=C2C=CC=CC2=C1 Chemical compound Cl.C1=NCC=C2C=CC=CC2=C1 DCGIEIRGPBYBHD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- QDPWXIAIQNRHGP-UHFFFAOYSA-N 10,10a-dihydro-[1,4,2]dioxazolo[2,3-b]isoquinolin-5-one Chemical compound C1ON2C(C3=CC=CC=C3CC2O1)=O QDPWXIAIQNRHGP-UHFFFAOYSA-N 0.000 description 2
- UBBLWCUYCWLFDQ-UHFFFAOYSA-N 2,3-dimethoxy-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC=C2C(=O)N(OC)C(OC)CC2=C1 UBBLWCUYCWLFDQ-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
- YGLDQFWPUCURIP-UHFFFAOYSA-N 3h-3-benzazepine Chemical compound C1=CNC=CC2=CC=CC=C21 YGLDQFWPUCURIP-UHFFFAOYSA-N 0.000 description 2
- YZGFLHYYILUCCS-UHFFFAOYSA-N 4-methoxyisoquinoline Chemical compound C1=CC=C2C(OC)=CN=CC2=C1 YZGFLHYYILUCCS-UHFFFAOYSA-N 0.000 description 2
- WIUVXEAALLSOQN-UHFFFAOYSA-N 6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-one Chemical compound C1=C2C(=O)N(C)CCC2=CC2=C1OCO2 WIUVXEAALLSOQN-UHFFFAOYSA-N 0.000 description 2
- VSOJKDUWYQCWFM-UHFFFAOYSA-N 7,8-dihydro-6h-[1,3]dioxolo[4,5-g]isoquinolin-5-one Chemical compound C1=C2C(=O)NCCC2=CC2=C1OCO2 VSOJKDUWYQCWFM-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VISFHOLIBPBFOB-UHFFFAOYSA-N C1OC2=CC=C3CCNC(C3=C2O1)=O Chemical compound C1OC2=CC=C3CCNC(C3=C2O1)=O VISFHOLIBPBFOB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- BDIZBBGNYDRCCA-UHFFFAOYSA-N N-methylcorydaldine Chemical compound C1CN(C)C(=O)C2=C1C=C(OC)C(OC)=C2 BDIZBBGNYDRCCA-UHFFFAOYSA-N 0.000 description 2
- 101100513046 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) eth-1 gene Proteins 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- IZCQDRVQVRENLX-UHFFFAOYSA-N dihydrate;trihydrochloride Chemical compound O.O.Cl.Cl.Cl IZCQDRVQVRENLX-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 230000010247 heart contraction Effects 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- XTBAPWCYTNCZTO-UHFFFAOYSA-N isoindol-1-one Chemical compound C1=CC=C2C(=O)N=CC2=C1 XTBAPWCYTNCZTO-UHFFFAOYSA-N 0.000 description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 2
- IYRMNDOLPONSCJ-UHFFFAOYSA-N isoquinolin-2-ium;chloride Chemical compound Cl.C1=NC=CC2=CC=CC=C21 IYRMNDOLPONSCJ-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000002604 ultrasonography Methods 0.000 description 2
- GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
- JZPDDOYOZALHFK-UHFFFAOYSA-N 1,2,3,4-tetrahydro-3-benzazepin-5-one Chemical compound O=C1CNCCC2=CC=CC=C12 JZPDDOYOZALHFK-UHFFFAOYSA-N 0.000 description 1
- JKEAOQHKFOPGKZ-UHFFFAOYSA-N 1,2,3,4-tetrahydro-3-benzazepin-5-one;hydrochloride Chemical compound Cl.O=C1CNCCC2=CC=CC=C12 JKEAOQHKFOPGKZ-UHFFFAOYSA-N 0.000 description 1
- FMRFUKZPHGBWHF-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-1-ol Chemical compound C1=CC=C2C(O)NCCC2=C1 FMRFUKZPHGBWHF-UHFFFAOYSA-N 0.000 description 1
- GYIYVTGAOWHWRI-UHFFFAOYSA-N 1,2,3,5-tetrahydro-3-benzazepin-4-one Chemical compound C1CNC(=O)CC2=CC=CC=C21 GYIYVTGAOWHWRI-UHFFFAOYSA-N 0.000 description 1
- DNUITAQGHRBVBX-UHFFFAOYSA-N 1,2-dimethoxy-4-propoxybenzene Chemical compound CCCOC1=CC=C(OC)C(OC)=C1 DNUITAQGHRBVBX-UHFFFAOYSA-N 0.000 description 1
- ORZMSMCZBZARKY-UHFFFAOYSA-N 1,3,2$l^{6}-benzodioxathiole 2,2-dioxide Chemical compound C1=CC=C2OS(=O)(=O)OC2=C1 ORZMSMCZBZARKY-UHFFFAOYSA-N 0.000 description 1
- UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 description 1
- IAZCKSJRRRXZEY-UHFFFAOYSA-N 1-(2-bromoethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCBr)C=C1 IAZCKSJRRRXZEY-UHFFFAOYSA-N 0.000 description 1
- OSPSTFKEHOVIGO-UHFFFAOYSA-N 1-(3-chloropropoxy)-3,5-dimethoxybenzene Chemical compound COC1=CC(OC)=CC(OCCCCl)=C1 OSPSTFKEHOVIGO-UHFFFAOYSA-N 0.000 description 1
- WYBOTXNKQGURAB-UHFFFAOYSA-N 1-(3-chloropropoxy)-3-methoxybenzene Chemical compound COC1=CC=CC(OCCCCl)=C1 WYBOTXNKQGURAB-UHFFFAOYSA-N 0.000 description 1
- YHHSOJRBOXOGFK-UHFFFAOYSA-N 1-(3-chloropropoxy)-3-methylbenzene Chemical compound CC1=CC=CC(OCCCCl)=C1 YHHSOJRBOXOGFK-UHFFFAOYSA-N 0.000 description 1
- SJZQJMFKQYZZAT-UHFFFAOYSA-N 1-(3-chloropropoxy)-4-methoxybenzene Chemical compound COC1=CC=C(OCCCCl)C=C1 SJZQJMFKQYZZAT-UHFFFAOYSA-N 0.000 description 1
- ZBAUZCCUGCBNMC-UHFFFAOYSA-N 1-(4-bromobutoxy)naphthalene Chemical compound C1=CC=C2C(OCCCCBr)=CC=CC2=C1 ZBAUZCCUGCBNMC-UHFFFAOYSA-N 0.000 description 1
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- QPVWDIOTNVVIDY-UHFFFAOYSA-N 2-(3-chloropropoxy)naphthalene Chemical compound C1=CC=CC2=CC(OCCCCl)=CC=C21 QPVWDIOTNVVIDY-UHFFFAOYSA-N 0.000 description 1
- REMQCPAKPUSPHJ-UHFFFAOYSA-N 2-(4-bromobutoxy)naphthalene Chemical class C1=CC=CC2=CC(OCCCCBr)=CC=C21 REMQCPAKPUSPHJ-UHFFFAOYSA-N 0.000 description 1
- GHTCEOPJYODOQF-UHFFFAOYSA-N 2-(4-bromobutyl)thiophene Chemical compound BrCCCCC1=CC=CS1 GHTCEOPJYODOQF-UHFFFAOYSA-N 0.000 description 1
- RUHJZSZTSCSTCC-UHFFFAOYSA-N 2-(bromomethyl)naphthalene Chemical compound C1=CC=CC2=CC(CBr)=CC=C21 RUHJZSZTSCSTCC-UHFFFAOYSA-N 0.000 description 1
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- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
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- AKPSLMUFDIXDJJ-UHFFFAOYSA-N 4-(bromomethyl)-1,2-dimethoxybenzene Chemical compound COC1=CC=C(CBr)C=C1OC AKPSLMUFDIXDJJ-UHFFFAOYSA-N 0.000 description 1
- NEBQMYHKOREVAL-UHFFFAOYSA-N 4-ethyl-1,2-dimethoxybenzene Chemical compound CCC1=CC=C(OC)C(OC)=C1 NEBQMYHKOREVAL-UHFFFAOYSA-N 0.000 description 1
- LQFPSYSAHKWJOU-UHFFFAOYSA-N 6,7,8,10-tetrahydro-[1,3]dioxolo[4,5-i][3]benzazepin-9-one Chemical compound C1OC=2C=CC3=C(CC(NCC3)=O)C2O1 LQFPSYSAHKWJOU-UHFFFAOYSA-N 0.000 description 1
- HQVFWMFRDZKLPB-UHFFFAOYSA-N 6,7,8,9-tetrahydro-[1,3]dioxolo[4,5-h]isoquinoline Chemical compound C1CNCC2=C(OCO3)C3=CC=C21 HQVFWMFRDZKLPB-UHFFFAOYSA-N 0.000 description 1
- NXUKTYWRHAAITI-UHFFFAOYSA-N 6-thiophen-2-ylhexyl methanesulfonate Chemical compound CS(=O)(=O)OCCCCCCC1=CC=CS1 NXUKTYWRHAAITI-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YBULLAOMWCZBJI-UHFFFAOYSA-N ClCCCOC1=CC=CC2=C(C(=CC=C12)OC)OC Chemical compound ClCCCOC1=CC=CC2=C(C(=CC=C12)OC)OC YBULLAOMWCZBJI-UHFFFAOYSA-N 0.000 description 1
- MYEIDJPOUKASEC-UHFFFAOYSA-N Dihydrosafrole Chemical compound CCCC1=CC=C2OCOC2=C1 MYEIDJPOUKASEC-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001328813 Methles Species 0.000 description 1
- MMTUALAWHUAUBU-UHFFFAOYSA-N N1CC(CCCC1)N1CCC2=C(C(C1=O)C)C=C(C(=C2)OC)OC Chemical compound N1CC(CCCC1)N1CCC2=C(C(C1=O)C)C=C(C(=C2)OC)OC MMTUALAWHUAUBU-UHFFFAOYSA-N 0.000 description 1
- 241000746935 Nolina Species 0.000 description 1
- IKFSULRGAJACBS-UHFFFAOYSA-N O.Cl.Cl.Cl.Cl.Cl.Cl Chemical compound O.Cl.Cl.Cl.Cl.Cl.Cl IKFSULRGAJACBS-UHFFFAOYSA-N 0.000 description 1
- 102000006463 Talin Human genes 0.000 description 1
- 108010083809 Talin Proteins 0.000 description 1
- 235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- XEKAUTDWPYQNFU-UHFFFAOYSA-N chlorane Chemical compound Cl.Cl.Cl XEKAUTDWPYQNFU-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- HNWWAWKDVFVJRG-UHFFFAOYSA-N hydron;6-hydroxy-1h-pyridin-2-one;chloride Chemical compound Cl.OC1=CC=CC(=O)N1 HNWWAWKDVFVJRG-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- UTKNBHYJLFLZRD-UHFFFAOYSA-N isoquinolin-2-ium;hydroxide Chemical compound [OH-].C1=[NH+]C=CC2=CC=CC=C21 UTKNBHYJLFLZRD-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 101150006061 neur gene Proteins 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- PFEJJYZYEFRQEA-NKWVEPMBSA-N pyr-Pro-OH Natural products OC(=O)[C@H]1CCCN1C(=O)[C@@H]1CCC(=O)N1 PFEJJYZYEFRQEA-NKWVEPMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- CVQPQLRQAKXFFF-UHFFFAOYSA-N trihydrate;trihydrochloride Chemical compound O.O.O.Cl.Cl.Cl CVQPQLRQAKXFFF-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D401/06—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 only aliphatic carbon atoms
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero 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
- C07D405/14—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 three or more hetero rings
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Peptides Or Proteins (AREA)
- Gears, Cams (AREA)
- Valve-Gear Or Valve Arrangements (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873717561 DE3717561A1 (de) | 1987-05-25 | 1987-05-25 | Indol-, isochinolin- und benzazepinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1561823A3 true SU1561823A3 (ru) | 1990-04-30 |
Family
ID=6328351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU884355736A SU1561823A3 (ru) | 1987-05-25 | 1988-05-24 | Способ получени производных циклического амина или их кислотно-аддитивных солей |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0292840B1 (enExample) |
| JP (1) | JP2634190B2 (enExample) |
| KR (1) | KR960009432B1 (enExample) |
| AT (1) | ATE126225T1 (enExample) |
| AU (1) | AU607765B2 (enExample) |
| CA (2) | CA1287226C (enExample) |
| DD (1) | DD284678A5 (enExample) |
| DE (2) | DE3717561A1 (enExample) |
| DK (1) | DK282188A (enExample) |
| ES (1) | ES2076147T3 (enExample) |
| FI (1) | FI94343C (enExample) |
| GR (1) | GR3017550T3 (enExample) |
| HU (1) | HU198201B (enExample) |
| IE (1) | IE68842B1 (enExample) |
| IL (1) | IL86477A (enExample) |
| IN (1) | IN169514B (enExample) |
| NO (1) | NO171017C (enExample) |
| NZ (1) | NZ224756A (enExample) |
| PT (1) | PT87567B (enExample) |
| SU (1) | SU1561823A3 (enExample) |
| ZA (1) | ZA883680B (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3640641A1 (de) * | 1986-11-28 | 1988-07-14 | Thomae Gmbh Dr K | Neue heteroaromatische aminderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
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| BRPI1010831A2 (pt) | 2009-05-12 | 2016-04-05 | Addex Pharmaceuticals Sa | derivados de 1,2,4-triazolo[4,3-a]piridina e seu como moduladores alostéricos positivos de receptores de mglur2 |
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| ES2860298T3 (es) | 2014-01-21 | 2021-10-04 | Janssen Pharmaceutica Nv | Combinaciones que comprenden moduladores alostéricos positivos del receptor glutamatérgico metabotrópico de subtipo 2 y su uso |
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|---|---|---|---|---|
| DE2639718C2 (de) * | 1976-09-03 | 1987-03-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | 1-[6,7-Dimethoxy-3,4-dihydro-2H-isochinolin-1-on-2-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-äthyl)-amino]-propan, dessen physiologisch verträgliche Säureadditionssalze und diese Verbindungen enthaltende Arzneimittel |
| DE3119874A1 (de) * | 1981-05-19 | 1982-12-09 | Dr. Karl Thomae Gmbh, 7950 Biberach | "benzazepinderivate, ihre herstellung und ihre verwendung als arzneimittel" |
| DE3418271A1 (de) * | 1984-05-17 | 1985-11-21 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue benzazepinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE3418270A1 (de) * | 1984-05-17 | 1985-11-21 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue aminotetralinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE3541811A1 (de) * | 1985-11-27 | 1987-06-04 | Thomae Gmbh Dr K | Neue cyclische aminderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
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| IL89156A (en) * | 1988-07-12 | 1993-05-13 | Synthelabo | Derivatives of 2-((4-piperidinyl) methyl)- 1,2,3,4- tetrahydroisoquinoline, their preparation and their application in therapeutics |
| FR2686339B1 (fr) * | 1992-01-22 | 1994-03-11 | Adir Cie | Nouveaux amides et sulfonamides naphtaleniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
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1987
- 1987-05-25 DE DE19873717561 patent/DE3717561A1/de not_active Ceased
-
1988
- 1988-05-17 EP EP88107867A patent/EP0292840B1/de not_active Expired - Lifetime
- 1988-05-19 IN IN400/CAL/88A patent/IN169514B/en unknown
- 1988-05-20 CA CA000567453A patent/CA1287226C/en not_active Expired - Lifetime
- 1988-05-20 CA CA000567464A patent/CA1330993C/en not_active Expired - Fee Related
- 1988-05-20 DD DD88315962A patent/DD284678A5/de not_active IP Right Cessation
- 1988-05-23 NZ NZ224756A patent/NZ224756A/xx unknown
- 1988-05-23 FI FI882418A patent/FI94343C/fi not_active IP Right Cessation
- 1988-05-24 IE IE155988A patent/IE68842B1/en not_active IP Right Cessation
- 1988-05-24 ZA ZA883680A patent/ZA883680B/xx unknown
- 1988-05-24 PT PT87567A patent/PT87567B/pt not_active IP Right Cessation
- 1988-05-24 ES ES88107867T patent/ES2076147T3/es not_active Expired - Lifetime
- 1988-05-24 KR KR88006072A patent/KR960009432B1/ko not_active Expired - Fee Related
- 1988-05-24 NO NO882258A patent/NO171017C/no unknown
- 1988-05-24 AU AU16562/88A patent/AU607765B2/en not_active Ceased
- 1988-05-24 IL IL86477A patent/IL86477A/xx unknown
- 1988-05-24 AT AT88107867T patent/ATE126225T1/de not_active IP Right Cessation
- 1988-05-24 DE DE3854280T patent/DE3854280D1/de not_active Expired - Fee Related
- 1988-05-24 HU HU882647A patent/HU198201B/hu not_active IP Right Cessation
- 1988-05-24 DK DK282188A patent/DK282188A/da not_active Application Discontinuation
- 1988-05-24 JP JP63126910A patent/JP2634190B2/ja not_active Expired - Lifetime
- 1988-05-24 SU SU884355736A patent/SU1561823A3/ru active
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1995
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