NO833778L - 1,3,4,6,7,11b-heksahydro-7-aryl-2h-pyrazino(2,1-alfa)isokinoliner og fremgangsmaate ved fremstilling derav - Google Patents
1,3,4,6,7,11b-heksahydro-7-aryl-2h-pyrazino(2,1-alfa)isokinoliner og fremgangsmaate ved fremstilling deravInfo
- Publication number
- NO833778L NO833778L NO833778A NO833778A NO833778L NO 833778 L NO833778 L NO 833778L NO 833778 A NO833778 A NO 833778A NO 833778 A NO833778 A NO 833778A NO 833778 L NO833778 L NO 833778L
- Authority
- NO
- Norway
- Prior art keywords
- pyrazino
- hexahydro
- cis
- phenyl
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000002537 isoquinolines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- -1 aralkanoyl Chemical group 0.000 claims abstract description 10
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000002252 acyl group Chemical group 0.000 claims abstract 3
- 125000004423 acyloxy group Chemical group 0.000 claims abstract 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 230000003287 optical effect Effects 0.000 claims description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- 150000004678 hydrides Chemical class 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000012380 dealkylating agent Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000007336 electrophilic substitution reaction Methods 0.000 claims 2
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 claims 1
- 150000001470 diamides Chemical class 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000001430 anti-depressive effect Effects 0.000 abstract description 5
- 239000000935 antidepressant agent Substances 0.000 abstract description 5
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- 230000001713 cholinergic effect Effects 0.000 abstract description 3
- 229940005513 antidepressants Drugs 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 74
- 239000007787 solid Substances 0.000 description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
- 239000000203 mixture Substances 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 38
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 238000001914 filtration Methods 0.000 description 31
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 238000010992 reflux Methods 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 239000007789 gas Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 15
- 239000000284 extract Substances 0.000 description 12
- 229910000085 borane Inorganic materials 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- MXKNYRDCLVGGJD-JYRWABTFSA-N (7s,11br)-2-methyl-7-phenyl-1,3,4,6,7,11b-hexahydropyrazino[2,1-a]isoquinoline;dihydrochloride Chemical compound Cl.Cl.C1([C@@H]2CN3CCN(C[C@H]3C3=CC=CC=C32)C)=CC=CC=C1 MXKNYRDCLVGGJD-JYRWABTFSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000002026 chloroform extract Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- FJTRNUFGAQCIKT-UHFFFAOYSA-N isoquinoline-3,4-dione Chemical compound C1=CC=C2C(=O)C(=O)N=CC2=C1 FJTRNUFGAQCIKT-UHFFFAOYSA-N 0.000 description 6
- GACFTYIPBQCTQB-UHFFFAOYSA-N isoquinoline;dihydrochloride Chemical compound Cl.Cl.C1=NC=CC2=CC=CC=C21 GACFTYIPBQCTQB-UHFFFAOYSA-N 0.000 description 6
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 5
- JWDCLQHNIUCQJT-OALUTQOASA-N (7s,11br)-2-methyl-7-phenyl-1,3,4,6,7,11b-hexahydropyrazino[2,1-a]isoquinoline Chemical compound C1([C@@H]2CN3CCN(C[C@H]3C3=CC=CC=C32)C)=CC=CC=C1 JWDCLQHNIUCQJT-OALUTQOASA-N 0.000 description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- MFQHFXGAXMXPCO-DLBZAZTESA-N (7s,11bs)-2-methyl-7-phenyl-1,6,7,11b-tetrahydropyrazino[2,1-a]isoquinoline-3,4-dione Chemical compound C1([C@@H]2CN3[C@@H](C4=CC=CC=C42)CN(C(C3=O)=O)C)=CC=CC=C1 MFQHFXGAXMXPCO-DLBZAZTESA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 230000020335 dealkylation Effects 0.000 description 3
- 238000006900 dealkylation reaction Methods 0.000 description 3
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- DSJUYVRAFKJQER-UHFFFAOYSA-N 1-(chloromethyl)-4-phenyl-3,4-dihydroisoquinoline;hydrochloride Chemical compound Cl.C12=CC=CC=C2C(CCl)=NCC1C1=CC=CC=C1 DSJUYVRAFKJQER-UHFFFAOYSA-N 0.000 description 2
- OXSDPKKYPZJMAR-UHFFFAOYSA-N 2-chloro-n-(1,1-diphenylethyl)acetamide Chemical compound C=1C=CC=CC=1C(NC(=O)CCl)(C)C1=CC=CC=C1 OXSDPKKYPZJMAR-UHFFFAOYSA-N 0.000 description 2
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- 102000030621 adenylate cyclase Human genes 0.000 description 2
- 108060000200 adenylate cyclase Proteins 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
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- 230000004048 modification Effects 0.000 description 2
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- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
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- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 238000006172 aromatic nitration reaction Methods 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 229960005426 doxepin Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000000537 electroencephalography Methods 0.000 description 1
- 238000007345 electrophilic aromatic substitution reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- PLIGPBGDXASWPX-UHFFFAOYSA-N iprindole Chemical compound C1CCCCCC2=C1N(CCCN(C)C)C1=CC=CC=C12 PLIGPBGDXASWPX-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960000582 mepyramine Drugs 0.000 description 1
- 229960003955 mianserin Drugs 0.000 description 1
- UYHHYORUPUOBTL-IRXDYDNUSA-N n-methyl-1-[(1r,4s)-4-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methanamine Chemical compound C1([C@@H]2CN[C@H](C3=CC=CC=C32)CNC)=CC=CC=C1 UYHHYORUPUOBTL-IRXDYDNUSA-N 0.000 description 1
- ABSPXUAYPUJLBV-SZKOKKDDSA-N n-methyl-1-[(1r,4s)-4-phenyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methanamine;dihydrochloride Chemical compound Cl.Cl.C1([C@@H]2CN[C@H](C3=CC=CC=C32)CNC)=CC=CC=C1 ABSPXUAYPUJLBV-SZKOKKDDSA-N 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
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
- 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
- A61P25/24—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (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)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/435,132 US4517187A (en) | 1982-10-18 | 1982-10-18 | 1,3,4,6,7-11b-Hexahydro-7-phenyl-2H-pyrazino[2,1-a]isoquinolines methods of preparation, and use as antidepressants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO833778L true NO833778L (no) | 1984-04-24 |
Family
ID=23727113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO833778A NO833778L (no) | 1982-10-18 | 1983-10-17 | 1,3,4,6,7,11b-heksahydro-7-aryl-2h-pyrazino(2,1-alfa)isokinoliner og fremgangsmaate ved fremstilling derav |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4517187A (fi) |
| EP (1) | EP0107825B1 (fi) |
| JP (1) | JPS5989680A (fi) |
| KR (1) | KR870000622B1 (fi) |
| AT (1) | ATE32720T1 (fi) |
| AU (1) | AU1955583A (fi) |
| CA (1) | CA1219874A (fi) |
| DE (1) | DE3375784D1 (fi) |
| DK (1) | DK477783A (fi) |
| FI (1) | FI833784A (fi) |
| IL (1) | IL69586A (fi) |
| NO (1) | NO833778L (fi) |
| NZ (1) | NZ205425A (fi) |
| ZA (1) | ZA836448B (fi) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4782058A (en) * | 1985-04-26 | 1988-11-01 | Pennwalt Corporation | 1,3,4,6,7,11b-Hexahydro-6-phenyl-2H-pyrazino-(2,1-a)isoquinolines, for anti-histamine or anti-depression treatment |
| US4678791A (en) * | 1985-05-07 | 1987-07-07 | Pennwalt Corporation | 6-phenyl-1,2-3,4,4a,5-6,10b-octahydrobenz(h)isoquinolines useful for treating depression |
| US4772705A (en) * | 1985-07-25 | 1988-09-20 | Pennwalt Corporation | Processes for the preparation of trans 1,3,4,6,7,11b-hexahydro-7-aryl-2H-pyrazinol[2,1-a]isoquinolines |
| WO1990008148A1 (en) * | 1989-01-23 | 1990-07-26 | Pfizer Inc. | Bis-aza-bicyclic anxiolytic agents |
| CN1068327C (zh) * | 1994-09-30 | 2001-07-11 | 辉瑞大药厂 | 2,7－取代的八氢－1H－吡啶并[1,2－a]吡嗪衍生物 |
| CA2953040A1 (en) * | 2014-08-27 | 2016-03-03 | F. Hoffmann-La Roche Ag | Substituted pyrazino[2,1-a]isoquinoline derivatives for the treatment of cns disorders |
| MX2022004739A (es) * | 2019-10-31 | 2022-07-19 | Holosmedic | Compuesto novedoso y composicion farmaceutica para prevencion o tratamiento de cancer que comprende el mismo. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1050901A (fi) * | 1964-02-06 | |||
| US3684813A (en) * | 1970-04-08 | 1972-08-15 | Sterling Drug Inc | Hexahydropyrazinoisoquinolines |
| DE2441261A1 (de) * | 1974-08-28 | 1976-03-18 | Merck Patent Gmbh | Ringsubstituierte pyrazino-isochinolin-derivat und verfahren zu ihrer herstellung |
| US4162319A (en) * | 1974-08-28 | 1979-07-24 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Ring substituted pyrazino-isoquinoline derivatives and their preparation |
-
1982
- 1982-10-18 US US06/435,132 patent/US4517187A/en not_active Expired - Fee Related
-
1983
- 1983-08-26 CA CA000435430A patent/CA1219874A/en not_active Expired
- 1983-08-29 IL IL69586A patent/IL69586A/xx unknown
- 1983-08-30 NZ NZ205425A patent/NZ205425A/en unknown
- 1983-08-31 ZA ZA836448A patent/ZA836448B/xx unknown
- 1983-09-26 AU AU19555/83A patent/AU1955583A/en not_active Abandoned
- 1983-10-07 DE DE8383110044T patent/DE3375784D1/de not_active Expired
- 1983-10-07 EP EP83110044A patent/EP0107825B1/en not_active Expired
- 1983-10-07 AT AT83110044T patent/ATE32720T1/de not_active IP Right Cessation
- 1983-10-13 JP JP58190025A patent/JPS5989680A/ja active Pending
- 1983-10-17 DK DK477783A patent/DK477783A/da not_active Application Discontinuation
- 1983-10-17 NO NO833778A patent/NO833778L/no unknown
- 1983-10-17 FI FI833784A patent/FI833784A/fi not_active Application Discontinuation
- 1983-10-18 KR KR1019830004928A patent/KR870000622B1/ko active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5989680A (ja) | 1984-05-23 |
| FI833784A0 (fi) | 1983-10-17 |
| KR870000622B1 (ko) | 1987-03-26 |
| EP0107825A1 (en) | 1984-05-09 |
| FI833784A (fi) | 1984-04-19 |
| DK477783A (da) | 1984-04-19 |
| ATE32720T1 (de) | 1988-03-15 |
| CA1219874A (en) | 1987-03-31 |
| NZ205425A (en) | 1986-05-09 |
| IL69586A0 (en) | 1983-11-30 |
| KR840006656A (ko) | 1984-12-01 |
| DE3375784D1 (en) | 1988-04-07 |
| DK477783D0 (da) | 1983-10-17 |
| IL69586A (en) | 1986-07-31 |
| ZA836448B (en) | 1984-07-25 |
| AU1955583A (en) | 1984-05-03 |
| EP0107825B1 (en) | 1988-03-02 |
| US4517187A (en) | 1985-05-14 |
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