DD270911A5 - Verfahren zur herstellung von neuen heteroaromatischen aminderivaten - Google Patents

Verfahren zur herstellung von neuen heteroaromatischen aminderivaten Download PDF

Info

Publication number: DD270911A5
Authority: DD; German Democratic Republic
Prior art keywords: methyl; propyl; amino; oxo; group
Prior art date: 1986-11-28

Application number

DD87309530A

Other languages

German (de)

English (en)

Inventor

Andreas Bomhard

Joachim Heider

Manfred Psiorz

Norbert Hauel

Berthold Narr

Klaus Noll

Christian Lillie

Walter Kobinger

Willi Diederen

Original Assignee

��K@��@��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-11-28

Filing date

1987-11-26

Publication date

1989-08-16

1987-11-26 Application filed by ��K@��@��@��k�� filed Critical ��K@��@��@��k��

1989-08-16 Publication of DD270911A5 publication Critical patent/DD270911A5/de

Links

238000000034 method Methods 0.000 title claims description 24
230000008569 process Effects 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 10
150000001412 amines Chemical class 0.000 title description 3
-1 heteroaromatic amine Chemical class 0.000 claims abstract description 90
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims abstract description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
229910052799 carbon Inorganic materials 0.000 claims abstract description 5
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract 2
125000005605 benzo group Chemical group 0.000 claims description 62
150000001875 compounds Chemical class 0.000 claims description 52
150000003254 radicals Chemical class 0.000 claims description 33
239000002253 acid Substances 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
238000006243 chemical reaction Methods 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 18
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 16
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 15
230000009467 reduction Effects 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 13
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
230000001681 protective effect Effects 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
238000009835 boiling Methods 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 7
238000003776 cleavage reaction Methods 0.000 claims description 7
229910052987 metal hydride Inorganic materials 0.000 claims description 7
150000004681 metal hydrides Chemical class 0.000 claims description 7
150000007522 mineralic acids Chemical class 0.000 claims description 7
150000007524 organic acids Chemical class 0.000 claims description 7
235000005985 organic acids Nutrition 0.000 claims description 7
230000002829 reductive effect Effects 0.000 claims description 7
230000007017 scission Effects 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
229910052717 sulfur Inorganic materials 0.000 claims description 6
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 5
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 5
229910000085 borane Inorganic materials 0.000 claims description 5
230000000269 nucleophilic effect Effects 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 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
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
150000001204 N-oxides Chemical class 0.000 claims description 2
125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000002071 phenylalkoxy group Chemical group 0.000 claims description 2
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000003396 thiol group Chemical class [H]S* 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
239000011593 sulfur Substances 0.000 claims 2
101100070530 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) het-6 gene Proteins 0.000 claims 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims 1
125000005530 alkylenedioxy group Chemical group 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 85
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 46
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
239000000741 silica gel Substances 0.000 description 29
229910002027 silica gel Inorganic materials 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
239000000460 chlorine Substances 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
238000002844 melting Methods 0.000 description 22
230000008018 melting Effects 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
238000006722 reduction reaction Methods 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
XTBAPWCYTNCZTO-UHFFFAOYSA-N 1H-isoindolone Natural products C1=CC=C2C(=O)N=CC2=C1 XTBAPWCYTNCZTO-UHFFFAOYSA-N 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 8
BJBFQRYCWBPPMP-UHFFFAOYSA-N 6,7-dimethoxy-2-[3-(methylamino)propyl]-3,4-dihydroisoquinolin-1-one Chemical compound COC1=C(OC)C=C2C(=O)N(CCCNC)CCC2=C1 BJBFQRYCWBPPMP-UHFFFAOYSA-N 0.000 description 7
230000000875 corresponding effect Effects 0.000 description 7
239000012362 glacial acetic acid Substances 0.000 description 7
239000012280 lithium aluminium hydride Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000013543 active substance Substances 0.000 description 6
239000012298 atmosphere Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 6
230000000144 pharmacologic effect Effects 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
HNHVRXLXBXIYNJ-UHFFFAOYSA-N 4,5-dimethoxy-7a-[3-(methylamino)propyl]-3ah-isoindole-1,3-dione Chemical compound C1=CC(OC)=C(OC)C2C(=O)NC(=O)C21CCCNC HNHVRXLXBXIYNJ-UHFFFAOYSA-N 0.000 description 5
229920002261 Corn starch Polymers 0.000 description 5
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
239000008120 corn starch Substances 0.000 description 5
229940093915 gynecological organic acid Drugs 0.000 description 5
239000008101 lactose Substances 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000001267 polyvinylpyrrolidone Substances 0.000 description 5
229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
230000009090 positive inotropic effect Effects 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
239000000600 sorbitol Substances 0.000 description 5
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
241000700199 Cavia porcellus Species 0.000 description 4
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000002585 base Substances 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
229910052796 boron Inorganic materials 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
125000002541 furyl group Chemical group 0.000 description 4
210000002837 heart atrium Anatomy 0.000 description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000010992 reflux Methods 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
YWPMKTWUFVOFPL-UHFFFAOYSA-N 3,4-dihydro-2h-isoquinolin-1-one Chemical compound C1=CC=C2C(=O)NCCC2=C1 YWPMKTWUFVOFPL-UHFFFAOYSA-N 0.000 description 3
BOTFMNQFIBSYCP-UHFFFAOYSA-N 3-(5-oxo-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-yl)propanal Chemical compound C1=C2C(=O)N(CCC=O)CCC2=CC2=C1OCO2 BOTFMNQFIBSYCP-UHFFFAOYSA-N 0.000 description 3
206010019280 Heart failures Diseases 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
230000001077 hypotensive effect Effects 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
208000031225 myocardial ischemia Diseases 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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
238000011282 treatment Methods 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
XQZUHTDYDIRXPP-UHFFFAOYSA-N 3-(2-bromoethyl)thiophene Chemical compound BrCCC=1C=CSC=1 XQZUHTDYDIRXPP-UHFFFAOYSA-N 0.000 description 2
BIPHTPAACXRHRW-UHFFFAOYSA-N 3-(6,7-dimethyl-1,3-dioxo-7ah-isoindol-3a-yl)propanal Chemical compound C1=CC(C)=C(C)C2C(=O)NC(=O)C21CCC=O BIPHTPAACXRHRW-UHFFFAOYSA-N 0.000 description 2
BYAFKVRZEGMBQD-UHFFFAOYSA-N 6,7-dihydro-[1,3]dioxolo[4,5-g]isoindol-8-one Chemical compound C1=C2OCOC2=C2C(=O)NCC2=C1 BYAFKVRZEGMBQD-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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239000003463 adsorbent Substances 0.000 description 1
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239000003708 ampul Substances 0.000 description 1
238000010009 beating Methods 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
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KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
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150000002366 halogen compounds Chemical class 0.000 description 1
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150000002431 hydrogen Chemical class 0.000 description 1
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RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
230000000297 inotrophic effect Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229960001375 lactose Drugs 0.000 description 1
229940057948 magnesium stearate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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DJIJZMRJLJLWGR-UHFFFAOYSA-N n-methyl-3-pyridin-2-ylpropan-1-amine Chemical compound CNCCCC1=CC=CC=N1 DJIJZMRJLJLWGR-UHFFFAOYSA-N 0.000 description 1
BUCBPAXMXLVROO-UHFFFAOYSA-N n-methyl-3-pyridin-4-ylpropan-1-amine Chemical compound CNCCCC1=CC=NC=C1 BUCBPAXMXLVROO-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
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TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
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230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
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239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- 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
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/10—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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
- 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
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen 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
- C07D401/02—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
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
- 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
- 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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Indole Compounds (AREA)

DD87309530A 1986-11-28 1987-11-26 Verfahren zur herstellung von neuen heteroaromatischen aminderivaten DD270911A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863640641 DE3640641A1 (de)	1986-11-28	1986-11-28	Neue heteroaromatische aminderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
DD270911A5 true DD270911A5 (de)	1989-08-16

Family

ID=6314973

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87309530A DD270911A5 (de)	1986-11-28	1987-11-26	Verfahren zur herstellung von neuen heteroaromatischen aminderivaten

Country Status (15)

Country	Link
US (2)	US4912115A (no)
EP (1)	EP0269968A3 (no)
JP (1)	JPS63150276A (no)
KR (1)	KR880006230A (no)
AU (1)	AU600995B2 (no)
DD (1)	DD270911A5 (no)
DE (1)	DE3640641A1 (no)
DK (1)	DK625087A (no)
FI (1)	FI875233A7 (no)
HU (1)	HU206208B (no)
IL (1)	IL84612A (no)
NO (1)	NO874955L (no)
NZ (1)	NZ222718A (no)
PT (1)	PT86227B (no)
ZA (1)	ZA878914B (no)

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US5250538A (en) *	1990-02-13	1993-10-05	Novo Nordisk A/S	Indole derivatives and their use
DK37790A (da) *	1990-02-13	1991-08-14	Novo Nordisk As	Indolderivater, deres fremstilling og anvendelse
FR2660657B1 (fr) *	1990-04-09	1993-05-07	Adir	Nouveaux derives du 3-aminochromane, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
US5273994A (en) *	1990-04-09	1993-12-28	Adir Et Compagnie	3-aminochroman compounds
JP2807577B2 (ja) *	1990-06-15	1998-10-08	エーザイ株式会社	環状アミド誘導体
FR2675802B1 (fr) *	1991-04-26	1993-12-24	Rhone Poulenc Rorer Sa	Antiserotonines, leur preparation et les medicaments les contenant.
US7151102B2 (en)	2000-10-30	2006-12-19	Kudos Pharmaceuticals Limited	Phthalazinone derivatives
DE60218458T2 (de)	2001-05-08	2007-11-15	Kudos Pharmaceuticals Ltd.	Isochinolinon derivate als parp inhibitoren
US7196085B2 (en)	2002-04-30	2007-03-27	Kudos Pharmaceuticals Limited	Phthalazinone derivatives
GB0305681D0 (en)	2003-03-12	2003-04-16	Kudos Pharm Ltd	Phthalazinone derivatives
US7449464B2 (en)	2003-03-12	2008-11-11	Kudos Pharmaceuticals Limited	Phthalazinone derivatives
FR2853649B1 (fr) *	2003-04-09	2006-07-14	Servier Lab	Nouveaux derives d'isoquinoleine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
GB0419072D0 (en)	2004-08-26	2004-09-29	Kudos Pharm Ltd	Phthalazinone derivatives
GB0521373D0 (en)	2005-10-20	2005-11-30	Kudos Pharm Ltd	Pthalazinone derivatives
US20090023727A1 (en) *	2007-07-05	2009-01-22	Muhammad Hashim Javaid	Phthalazinone derivatives
AU2008299721A1 (en)	2007-09-14	2009-03-19	Astrazeneca Ab	Phthalazinone derivatives
AU2008313467B2 (en)	2007-10-17	2013-08-29	Kudos Pharmaceuticals Limited	4- [3- (4-cyclopropanecarbonyl-piperazine-1-carbonyl) -4 -fluoro-benzyl] -2H-phthalazin-1-one
AR070221A1 (es)	2008-01-23	2010-03-25	Astrazeneca Ab	Derivados de ftalazinona inhibidores de polimerasas, composiciones farmaceuticas que los contienen y usos de los mismos para prevenir y/o tratar tumores cancerigenos,lesiones isquemicas y otras enfermedades asociadas.
BR122021018683B1 (pt) *	2008-10-07	2022-11-16	Kudos Pharmaceuticals Limited	Formulação farmacêutica de 4-[3-(4-ciclopropanocarbonil- piperazina-1-carbonil)-4-flúor- benzil]-2h-ftalazin-1-ona, uso de um polímero de matriz, forma de dosagem e método para produzir uma dispersão amorfa sólida
FR2941695B1 (fr) *	2009-02-04	2011-02-18	Servier Lab	Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable
US9745291B2 (en) *	2012-12-21	2017-08-29	Epizyme, Inc.	PRMT5 inhibitors containing a dihydro- or tetrahydroisoquinoline and uses thereof
US8993555B2 (en)	2012-12-21	2015-03-31	Epizyme, Inc.	PRMT5 inhibitors and uses thereof
US10653693B2 (en)	2014-08-04	2020-05-19	Epizyme, Inc.	PRMT5 inhibitors and uses thereof
US20240254132A1 (en) *	2021-07-16	2024-08-01	Denali Therapeutics Inc.	Compounds, compositions and methods

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US3919202A (en) *	1971-08-06	1975-11-11	Sterling Drug Inc	3-(Substituted amino)-1H-isoindoles
DE2345423A1 (de) *	1973-09-08	1975-03-20	Thomae Gmbh Dr K	Neue substituierte phenylaethylaminderivate, deren saeureadditionssalze, diese enthaltende arzneimittel sowie verfahren zu deren herstellung
US4118494A (en) *	1974-08-14	1978-10-03	Hoechst Aktiengesellschaft	Substituted 3,4-dihydro-2H-isoquinolin-1-thiones
US4087541A (en) *	1975-03-06	1978-05-02	Boehringer Ingelheim Gmbh	2-(Aralkylaminoalkyl)phthalimidines
AT352135B (de) *	1975-07-30	1979-09-10	Thomae Gmbh Dr K	Verfahren zur herstellung neuer homophthalimide und ihrer salze
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
CH645628A5 (en) *	1977-01-01	1984-10-15	Thomae Gmbh Dr K	Phenylethylamines
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FR2546886B2 (fr) *	1983-06-06	1986-05-16	Adir	Derives d'acides isoindoledicarboxyliques, leur preparation et compositions pharmaceutiques les contenant
DE3717561A1 (de) *	1987-05-25	1988-12-08	Thomae Gmbh Dr K	Indol-, isochinolin- und benzazepinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung

1986
- 1986-11-28 DE DE19863640641 patent/DE3640641A1/de not_active Withdrawn
1987
- 1987-11-21 EP EP19870117201 patent/EP0269968A3/de not_active Withdrawn
- 1987-11-25 US US07/125,626 patent/US4912115A/en not_active Expired - Fee Related
- 1987-11-26 DD DD87309530A patent/DD270911A5/de not_active IP Right Cessation
- 1987-11-26 PT PT86227A patent/PT86227B/pt not_active IP Right Cessation
- 1987-11-26 IL IL84612A patent/IL84612A/xx unknown
- 1987-11-27 HU HU875359A patent/HU206208B/hu not_active IP Right Cessation
- 1987-11-27 NO NO874955A patent/NO874955L/no unknown
- 1987-11-27 DK DK625087A patent/DK625087A/da not_active Application Discontinuation
- 1987-11-27 AU AU81876/87A patent/AU600995B2/en not_active Ceased
- 1987-11-27 KR KR870013414A patent/KR880006230A/ko not_active Withdrawn
- 1987-11-27 NZ NZ222718A patent/NZ222718A/xx unknown
- 1987-11-27 FI FI875233A patent/FI875233A7/fi not_active IP Right Cessation
- 1987-11-27 JP JP62299612A patent/JPS63150276A/ja active Pending
- 1987-11-27 ZA ZA878914A patent/ZA878914B/xx unknown
1991
- 1991-05-07 US US07/696,677 patent/US5116986A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DK625087D0 (da)	1987-11-27
HUT48619A (en)	1989-06-28
DE3640641A1 (de)	1988-07-14
FI875233A7 (fi)	1988-05-29
PT86227A (de)	1987-12-01
US5116986A (en)	1992-05-26
NO874955D0 (no)	1987-11-27
IL84612A0 (en)	1988-04-29
HU206208B (en)	1992-09-28
ZA878914B (en)	1989-07-26
FI875233A0 (fi)	1987-11-27
AU600995B2 (en)	1990-08-30
NO874955L (no)	1988-05-30
KR880006230A (ko)	1988-07-22
PT86227B (pt)	1990-11-07
AU8187687A (en)	1988-06-02
EP0269968A3 (de)	1990-10-17
EP0269968A2 (de)	1988-06-08
DK625087A (da)	1988-05-29
NZ222718A (en)	1990-05-28
IL84612A (en)	1992-03-29
US4912115A (en)	1990-03-27
JPS63150276A (ja)	1988-06-22

Legal Events

Date	Code	Title	Description
1999-09-30	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
JP2634190B2 (ja)	1997-07-23	新環状アミン誘導体及びこれらの化合物を含む薬学的組成物
US4737495A (en)	1988-04-12	(2H)-3-benzazepin-2-ones, their pharmaceutical compositions and their pharmaceutical uses
EP0269968A2 (de)	1988-06-08	Heteroaromatische Aminderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE69413542T2 (de)	1999-03-25	Perhydroisoindolderivate als substanz p antagonisten
EP0555824A1 (de)	1993-08-18	N-alpha-arylsulfonylierte Benzimidazolyl-alaninamid Derivate, diese enthaltende Arzneimittel sowie Verfahren zu ihrer Herstellung
DE10343098A1 (de)	2005-04-14	Tetrahydrochinoxaline und ihre Verwendung
EP0259793B1 (de)	1992-07-01	Neue Naphthylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE3418271A1 (de)	1985-11-21	Neue benzazepinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
EP0224794B1 (de)	1990-09-12	Neue cyclische Aminderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE10201240A1 (de)	2003-07-24	Substituierte Alkyluracile und ihre Verwendung
EP0068240B1 (de)	1985-09-25	2-Acylaminomethyl-1,4-benzodiazepin-Verbindungen sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0146787B1 (de)	1988-08-17	Indolderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
EP0109636B1 (de)	1989-01-18	Benzazepinderivate, ihre Herstellung und ihre Verwendung als Arzneimittel
DD247898A5 (de)	1987-07-22	Neue heteroaromatische aminderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE3531504A1 (de)	1987-03-12	3-aminomethylpyrrol-1-yl-alkylamine und diese verbindungen enthaltende therapeutische mittel
DE19957156A1 (de)	2001-05-31	Substituierte 1,2,3,4,5,6-Hexahydro-2,6-methano-3-benzazocine und ihre Verwendung als Arzneimittel
AT375079B (de)	1984-06-25	Verfahren zur herstellung von neuen trans-2,3,4,4a ,5,9b-hexahydro-1h-pyrido(4,3-b)indolen und ihren pharmazeutisch annehmbaren salzen
DE3522552A1 (de)	1987-01-02	Neue heteroaromatische aminderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE1620378A1 (de)	1970-03-26	Verfahren zur Herstellung neuer heterocyclischer Verbindungen