DD143776A5 - Verfahren zur herstellung von isochinolinverbindungen - Google Patents

Verfahren zur herstellung von isochinolinverbindungen Download PDF

Info

Publication number: DD143776A5
Authority: DD; German Democratic Republic
Prior art keywords: methyl; isoquinoline; hydrogen; acetyl; hexahydroindolo
Prior art date: 1978-05-23

Application number

DD79213066A

Other languages

German (de)

English (en)

Inventor

David Ch Horwell

David E Tupper

Original Assignee

Lilly Industries Ltd

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.)

1978-05-23

Filing date

1979-05-22

Publication date

1980-09-10

1979-05-22 Application filed by Lilly Industries Ltd filed Critical Lilly Industries Ltd

1980-09-10 Publication of DD143776A5 publication Critical patent/DD143776A5/de

Links

150000002537 isoquinolines Chemical class 0.000 title description 6
238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 42
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
239000001257 hydrogen Substances 0.000 claims abstract description 27
150000003839 salts Chemical class 0.000 claims abstract description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052736 halogen Chemical group 0.000 claims abstract description 8
150000002367 halogens Chemical group 0.000 claims abstract description 8
239000000126 substance Substances 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims abstract description 3
150000002431 hydrogen Chemical group 0.000 claims abstract 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 67
-1 isoquinoline compound Chemical class 0.000 claims description 17
238000000034 method Methods 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Chemical group 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000002168 alkylating agent Substances 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
230000002140 halogenating effect Effects 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims 1
210000003169 central nervous system Anatomy 0.000 abstract description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
208000035475 disorder Diseases 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
239000011541 reaction mixture Substances 0.000 description 23
239000000243 solution Substances 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
235000019439 ethyl acetate Nutrition 0.000 description 18
239000004480 active ingredient Substances 0.000 description 17
229940093499 ethyl acetate Drugs 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
238000002425 crystallisation Methods 0.000 description 13
230000008025 crystallization Effects 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
239000000047 product Substances 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000003814 drug Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
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
125000000753 cycloalkyl group Chemical group 0.000 description 5
239000008101 lactose Substances 0.000 description 5
230000003595 spectral effect Effects 0.000 description 5
CSBMIOWIGHJSON-BTJKTKAUSA-N (z)-but-2-enedioic acid;isoquinoline Chemical compound OC(=O)\C=C/C(O)=O.C1=NC=CC2=CC=CC=C21 CSBMIOWIGHJSON-BTJKTKAUSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-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
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
230000029936 alkylation Effects 0.000 description 4
238000005804 alkylation reaction Methods 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000002585 base Substances 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
239000011976 maleic acid Substances 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
VVONYSXZFDCKPH-UHFFFAOYSA-N 7h-isoquinolin-8-one Chemical compound C1=NC=C2C(=O)CC=CC2=C1 VVONYSXZFDCKPH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
102000003946 Prolactin Human genes 0.000 description 3
108010057464 Prolactin Proteins 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229940079593 drug Drugs 0.000 description 3
UJYGDMFEEDNVBF-UHFFFAOYSA-N ergocornin Chemical compound C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)C(C)C)C(C)C)C2)=C3C2=CNC3=C1 UJYGDMFEEDNVBF-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
150000002923 oximes Chemical class 0.000 description 3
239000008177 pharmaceutical agent Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
229940097325 prolactin Drugs 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000008107 starch Substances 0.000 description 3
229940032147 starch Drugs 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
239000003826 tablet Substances 0.000 description 3
GXEXLSDIVMVEFZ-UHFFFAOYSA-N 2-nitroprop-1-ene Chemical compound CC(=C)[N+]([O-])=O GXEXLSDIVMVEFZ-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 2
241001465754 Metazoa Species 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
238000005882 aldol condensation reaction Methods 0.000 description 2
238000005899 aromatization reaction Methods 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
FIMJSWFMQJGVAM-UHFFFAOYSA-N chloroform;hydrate Chemical compound O.ClC(Cl)Cl FIMJSWFMQJGVAM-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000008021 deposition Effects 0.000 description 2
125000005594 diketone group Chemical group 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000003921 oil Substances 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
GFXRUGFDOWPHNT-YFHOEESVSA-N (Z)-2-isoquinolin-1-ylbut-2-enedioic acid Chemical compound C1(=NC=CC2=CC=CC=C12)/C(=C/C(=O)O)/C(=O)O GFXRUGFDOWPHNT-YFHOEESVSA-N 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
ZYVORBSWPVDTCX-UHFFFAOYSA-N 1,2,2a,3-tetrahydrobenzo[cd]indole Chemical compound C1=CCC2CNC3=CC=CC1=C32 ZYVORBSWPVDTCX-UHFFFAOYSA-N 0.000 description 1
SCIJKNGXUCXAQB-UHFFFAOYSA-N 1,2,3,5-tetrahydroinden-4-one Chemical compound O=C1CC=CC2=C1CCC2 SCIJKNGXUCXAQB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ISVJYSRTVAYNMI-UHFFFAOYSA-N 1,4-dihydroindol-5-one Chemical compound C1=CC(=O)CC2=C1NC=C2 ISVJYSRTVAYNMI-UHFFFAOYSA-N 0.000 description 1
INOGLHRUEYDAHX-UHFFFAOYSA-N 1-chlorobenzotriazole Chemical compound C1=CC=C2N(Cl)N=NC2=C1 INOGLHRUEYDAHX-UHFFFAOYSA-N 0.000 description 1
LBMFWYCMCHRLBU-YTXUZFAGSA-N 2-[(6ar,9s)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]acetonitrile Chemical compound C1=CC(C2C[C@@H](CC#N)CN([C@@H]2C2)C)=C3C2=CNC3=C1 LBMFWYCMCHRLBU-YTXUZFAGSA-N 0.000 description 1
XMBCIDWARZDYSD-UHFFFAOYSA-N 2-nitrobut-1-ene Chemical compound CCC(=C)[N+]([O-])=O XMBCIDWARZDYSD-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

DD79213066A 1978-05-23 1979-05-22 Verfahren zur herstellung von isochinolinverbindungen DD143776A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB2135578		1978-05-23
GB7912970		1979-04-12

Publications (1)

Publication Number	Publication Date
DD143776A5 true DD143776A5 (de)	1980-09-10

Family

ID=26255289

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79213066A DD143776A5 (de)	1978-05-23	1979-05-22	Verfahren zur herstellung von isochinolinverbindungen

Country Status (24)

Country	Link
US (3)	US4245095A (fr)
EP (1)	EP0005646B1 (fr)
AR (1)	AR223177A1 (fr)
AU (1)	AU525554B2 (fr)
BG (1)	BG30326A3 (fr)
CA (1)	CA1118423A (fr)
CH (1)	CH641802A5 (fr)
DD (1)	DD143776A5 (fr)
DE (1)	DE2962784D1 (fr)
DK (1)	DK209279A (fr)
EG (1)	EG14314A (fr)
ES (1)	ES480849A1 (fr)
FI (1)	FI64595C (fr)
FR (1)	FR2453860A1 (fr)
GB (1)	GB2031409B (fr)
HU (1)	HU180494B (fr)
IL (1)	IL57344A (fr)
MX (1)	MX5565E (fr)
NZ (1)	NZ190513A (fr)
PL (1)	PL121298B1 (fr)
PT (1)	PT69645A (fr)
RO (1)	RO77552A (fr)
SU (1)	SU1072808A3 (fr)
YU (1)	YU120079A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3207775A1 (de) *	1981-03-13	1982-09-23	Sandoz-Patent-GmbH, 7850 Lörrach	Verfahren zur herstellung von mutterkornalkaloiden
DE3402392A1 (de)	1984-01-25	1985-08-01	Sandoz-Patent-GmbH, 7850 Lörrach	Neue ergolinderivate, deren herstellung und deren verwendung
GB8419278D0 (en) *	1984-07-27	1984-08-30	Lilly Industries Ltd	Pharmaceutical compounds
DE4033496A1 (de) *	1990-10-20	1992-04-23	Sandoz Ag	Neue ergolinderivate, ihre herstellung und verwendung

1979
- 1979-05-21 IL IL57344A patent/IL57344A/xx unknown
- 1979-05-21 AR AR276600A patent/AR223177A1/es active
- 1979-05-21 CH CH473279A patent/CH641802A5/fr not_active IP Right Cessation
- 1979-05-22 PL PL1979215772A patent/PL121298B1/pl unknown
- 1979-05-22 HU HU79LI342A patent/HU180494B/hu unknown
- 1979-05-22 CA CA000327987A patent/CA1118423A/fr not_active Expired
- 1979-05-22 EP EP79300906A patent/EP0005646B1/fr not_active Expired
- 1979-05-22 BG BG043692A patent/BG30326A3/xx unknown
- 1979-05-22 AU AU47288/79A patent/AU525554B2/en not_active Ceased
- 1979-05-22 DE DE7979300906T patent/DE2962784D1/de not_active Expired
- 1979-05-22 MX MX797993U patent/MX5565E/es unknown
- 1979-05-22 EG EG305/79A patent/EG14314A/xx active
- 1979-05-22 DD DD79213066A patent/DD143776A5/de unknown
- 1979-05-22 DK DK209279A patent/DK209279A/da unknown
- 1979-05-22 FI FI791615A patent/FI64595C/fi not_active IP Right Cessation
- 1979-05-22 NZ NZ190513A patent/NZ190513A/xx unknown
- 1979-05-22 PT PT69645A patent/PT69645A/pt unknown
- 1979-05-22 FR FR7912963A patent/FR2453860A1/fr active Granted
- 1979-05-22 YU YU01200/79A patent/YU120079A/xx unknown
- 1979-05-22 SU SU792765898A patent/SU1072808A3/ru active
- 1979-05-23 RO RO7997619A patent/RO77552A/fr unknown
- 1979-05-23 ES ES480849A patent/ES480849A1/es not_active Expired
- 1979-08-21 GB GB7929052A patent/GB2031409B/en not_active Expired
1980
- 1980-02-01 US US06/117,735 patent/US4245095A/en not_active Ceased
- 1980-04-18 US US06/141,752 patent/US4277480A/en not_active Expired - Lifetime
1981
- 1981-08-17 US US06/293,588 patent/USRE31194E/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
USRE31194E (en)	1983-03-29
EG14314A (en)	1983-12-31
AR223177A1 (es)	1981-07-31
FR2453860B1 (fr)	1982-02-19
GB2031409B (en)	1982-12-08
DE2962784D1 (en)	1982-07-01
YU120079A (en)	1983-06-30
PT69645A (en)	1979-06-01
CH641802A5 (fr)	1984-03-15
FI64595B (fi)	1983-08-31
SU1072808A3 (ru)	1984-02-07
FI64595C (fi)	1983-12-12
DK209279A (da)	1979-11-24
US4245095A (en)	1981-01-13
US4277480A (en)	1981-07-07
EP0005646A1 (fr)	1979-11-28
HU180494B (en)	1983-03-28
ES480849A1 (es)	1980-02-01
CA1118423A (fr)	1982-02-16
MX5565E (es)	1983-10-14
PL215772A1 (fr)	1980-07-14
GB2031409A (en)	1980-04-23
AU525554B2 (en)	1982-11-11
IL57344A (en)	1982-05-31
RO77552A (fr)	1982-02-01
FI791615A7 (fi)	1979-11-24
FR2453860A1 (fr)	1980-11-07
EP0005646B1 (fr)	1982-05-12
AU4728879A (en)	1979-11-29
IL57344A0 (en)	1979-09-30
BG30326A3 (bg)	1981-05-15
PL121298B1 (en)	1982-04-30
NZ190513A (en)	1982-03-30

Publication	Publication Date	Title
DE60014079T2 (de)	2006-03-02	Substituierte heterocyclisch kondensierte Gammacarboline
EP0657426B1 (fr)	1998-07-22	Dérivés tricycliques de pyrrole
DE3885357T2 (de)	1994-03-24	Anellierte Indolderivate.
DE69732090T2 (de)	2005-12-29	Indol-2,3-dione-3-oxim derivate
DE2609486A1 (de)	1977-05-12	Imidazo eckige klammer auf 1,5-a eckige klammer zu eckige klammer auf 1,4 eckige klammer zu diazepin-verbindungen und verfahren zu ihrer herstellung
KR100277481B1 (ko)	2001-02-01	이사틴옥심 유도체 및 그를 이용한 치료방법
EP0161218B1 (fr)	1991-06-26	Benzo-(pyrano et thiopyrano)pyridines
DE69819166T2 (de)	2004-07-22	8-substituierte-9h-1,3-dioxolo/4,5-h//2,3/benzodiazepin derivate als ampa/kainate-rezeptor-hemmer
DE3780015T2 (de)	1993-01-21	Kondensierte heterocyclische tetrahydroaminochinolinole und verwandte verbindungen, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel.
DD143776A5 (de)	1980-09-10	Verfahren zur herstellung von isochinolinverbindungen
DD210456A5 (de)	1984-06-13	Verfahren zur herstellung von pyrazolopyridin-verbindungen
EP0155903A1 (fr)	1985-09-25	Indolophénanthridines, leur préparation et leur utilisation
DE2125926A1 (de)	1972-01-27	Indoldenvate
DE3300522C2 (fr)	1992-01-09
DE3020267C2 (fr)	1989-06-22
AT374201B (de)	1984-03-26	Verfahren zur herstellung von neuen isochinolinverbindungen
EP0399159A2 (fr)	1990-11-28	Dérivés de quinoléine
DE2548737A1 (de)	1976-05-26	6-phenyl-spiro- eckige klammer auf cyclopropan-1,4'- eckige klammer auf 4h eckige klammer zu -s-triazolo eckige klammer auf 4,3-a eckige klammer zu - eckige klammer auf 1,4 eckige klammer zu benzodiazepine eckige klammer zu und verfahren zu deren herstellung
EP0072029A2 (fr)	1983-02-16	Triazolobenzazépines, procédé et intermédiaires pour leur fabrication et médicaments les contenant
AT395154B (de)	1992-10-12	Verfahren zur herstellung von neuen imidazo(1,5-a)(1,4)diazepinverbindungen
KR830000603B1 (ko)	1983-03-17	이소퀴놀린 유도체의 제조방법
AT395155B (de)	1992-10-12	Verfahren zur herstellung von neuen imidazo(1,5-a)(1,4)diazepinverbindungen
AT395152B (de)	1992-10-12	Verfahren zur herstellung von neuen imidazo (1,5-a)(1,4)diazepinverbindungen
DE2435041A1 (de)	1976-02-05	Neue 8-substituierte 6-aryl-4h-striazolo- eckige klammer auf 3,4c eckige klammer zu-thieno- eckige klammer auf 2,3e eckige klammer zu -1,4-diazepine, verfahren zu ihrer herstellung, ihre verwendung in arzneimitteln sowie zwischenprodukte und verfahren zur herstellung dieser zwischenprodukte
DE2445430C3 (fr)	1979-01-18