FI57106C - Foerfarande foer framstaellning av dibenso(c,f)-pyrazino(1,2-a)-azepinderivat - Google Patents
Foerfarande foer framstaellning av dibenso(c,f)-pyrazino(1,2-a)-azepinderivat Download PDFInfo
- Publication number
- FI57106C FI57106C FI750327A FI750327A FI57106C FI 57106 C FI57106 C FI 57106C FI 750327 A FI750327 A FI 750327A FI 750327 A FI750327 A FI 750327A FI 57106 C FI57106 C FI 57106C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- pyrazino
- compound
- halogen
- hydroxy group
- Prior art date
Links
- 229910052799 carbon Inorganic materials 0.000 title description 2
- 238000005057 refrigeration Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application 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
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
- -1 HgSO 4 Chemical class 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 230000000794 anti-serotonin Effects 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 239000003420 antiserotonin agent Substances 0.000 description 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical compound I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 229960002510 mandelic acid Drugs 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- XDJWZONZDVNKDU-UHFFFAOYSA-N 1314-24-5 Chemical compound O=POP=O XDJWZONZDVNKDU-UHFFFAOYSA-N 0.000 description 1
- ZWKWKJWRIYGQFD-UHFFFAOYSA-N 2-(1-aminoethyl)phenol Chemical class CC(N)C1=CC=CC=C1O ZWKWKJWRIYGQFD-UHFFFAOYSA-N 0.000 description 1
- QOJSLQLVPIFIPI-UHFFFAOYSA-N 2-[hydroxy(methyl)amino]-1-phenylethanol Chemical compound CN(O)CC(O)C1=CC=CC=C1 QOJSLQLVPIFIPI-UHFFFAOYSA-N 0.000 description 1
- KUSNCWLQRVMIRN-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-methyl-2-phenylethanamine Chemical compound ClCCN(C)CC(Cl)C1=CC=CC=C1 KUSNCWLQRVMIRN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- VDTUYUBSYHHRNO-BTJKTKAUSA-N C(\C=C/C(=O)O)(=O)O.C1=NC=CN2C1=CC=CC=C2 Chemical compound C(\C=C/C(=O)O)(=O)O.C1=NC=CN2C1=CC=CC=C2 VDTUYUBSYHHRNO-BTJKTKAUSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- ZCTYHONEGJTYQV-UHFFFAOYSA-N N-methylphenylethanolamine Chemical compound CNCC(O)C1=CC=CC=C1 ZCTYHONEGJTYQV-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000007655 dibenzoazepines Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- MXXMJJSIJDMYJZ-UHFFFAOYSA-N n-(2-phenylethyl)hydroxylamine Chemical class ONCCC1=CC=CC=C1 MXXMJJSIJDMYJZ-UHFFFAOYSA-N 0.000 description 1
- BYNBGYXIPZXLDD-UHFFFAOYSA-N n-chloro-n-methyl-2-phenylethanamine Chemical compound CN(Cl)CCC1=CC=CC=C1 BYNBGYXIPZXLDD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- WUCAUKBKDNXQEK-UHFFFAOYSA-N pyrazino[1,2-a]azepine Chemical compound C1=CC=CC=C2C=NC=CN21 WUCAUKBKDNXQEK-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/04—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7401807 | 1974-02-09 | ||
| NLAANVRAGE7401807,A NL179906C (nl) | 1974-02-09 | 1974-02-09 | Werkwijze voor het bereiden van 1,2,3,4,10,14b-hexahydrodibenzo(c,f)pyrazino (1,2-a)azepine derivaten. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI750327A7 FI750327A7 (en, 2012) | 1975-08-10 |
| FI57106B FI57106B (fi) | 1980-02-29 |
| FI57106C true FI57106C (fi) | 1980-06-10 |
Family
ID=19820725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI750327A FI57106C (fi) | 1974-02-09 | 1975-02-06 | Foerfarande foer framstaellning av dibenso(c,f)-pyrazino(1,2-a)-azepinderivat |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US4025513A (en, 2012) |
| JP (1) | JPS5315520B2 (en, 2012) |
| CA (1) | CA1084490A (en, 2012) |
| CH (1) | CH613705A5 (en, 2012) |
| DE (1) | DE2505239A1 (en, 2012) |
| DK (1) | DK150144C (en, 2012) |
| ES (1) | ES434533A1 (en, 2012) |
| FI (1) | FI57106C (en, 2012) |
| FR (1) | FR2260579B1 (en, 2012) |
| GB (2) | GB1498633A (en, 2012) |
| HU (1) | HU169018B (en, 2012) |
| NL (1) | NL179906C (en, 2012) |
| SE (1) | SE418745B (en, 2012) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4217452A (en) | 1974-02-09 | 1980-08-12 | Akzona Incorporated | Synthesis for the preparation of tetracyclic compounds |
| NL179906C (nl) | 1974-02-09 | 1986-12-01 | Akzo Nv | Werkwijze voor het bereiden van 1,2,3,4,10,14b-hexahydrodibenzo(c,f)pyrazino (1,2-a)azepine derivaten. |
| JPS5655174U (en, 2012) * | 1979-10-06 | 1981-05-14 | ||
| DE3368634D1 (en) * | 1982-03-05 | 1987-02-05 | Beecham Group Plc | Pentacyclic compounds |
| US4515792A (en) * | 1982-09-30 | 1985-05-07 | Ciba-Geigy Corporation | Tetracyclic heterocycles and antidepressant compositions thereof |
| GB2138016B (en) * | 1983-04-05 | 1986-10-29 | Bostik Ltd | Adhesive bonding |
| PT95522B (pt) * | 1989-10-05 | 1997-08-29 | Sankyo Co | Processo para a preparacao de novos compostos tetraciclicos com accao anti-alergica e anti-asmatica e de composicoes farmaceuticas que os contem |
| EP0539164A1 (en) * | 1991-10-23 | 1993-04-28 | Sankyo Company Limited | Nitrogen-containing tetracyclic compounds having anti-allergic and anti-asthmatic activities, their preparation and use |
| DE4305659A1 (de) * | 1993-02-24 | 1994-08-25 | Heumann Pharma Gmbh & Co | Verfahren zur Herstellung von 1,2,3,4,10,14b-Hexahydro-2-methyl-dibenzo[c,f]pyrazino[1,2-a]azepin und seiner Salze |
| EP1017695A4 (en) * | 1997-09-26 | 2002-01-16 | Univ Monash | RESOLUTION OF OPTICALLY ACTIVE COMPOUNDS |
| YU74201A (sh) | 1999-04-19 | 2004-05-12 | Teva Pharmaceutical Industries Ltd. | Nova sinteza prstena piperazina |
| WO2001025185A1 (fr) | 1999-09-30 | 2001-04-12 | Sumika Fine Chemicals Co., Ltd. | Procede de production de derive de piperazine |
| WO2009128057A2 (en) | 2008-04-18 | 2009-10-22 | UNIVERSITY COLLEGE DUBLIN, NATIONAL UNIVERSITY OF IRELAND, DUBLIN et al | Psycho-pharmaceuticals |
| CN102649779A (zh) * | 2012-04-20 | 2012-08-29 | 山东鲁药制药有限公司 | 一种药物中间体1-甲基-3-苯基哌嗪的合成方法 |
| CN102911793B (zh) * | 2012-10-04 | 2013-10-23 | 盐城师范学院 | 一种功能化碱性离子液体及其在生物柴油制备中的应用 |
| CN102876466B (zh) * | 2012-10-05 | 2013-10-23 | 盐城师范学院 | 一种碱性离子液体催化酯交换反应的方法 |
| CN104892608B (zh) * | 2015-06-29 | 2017-06-20 | 山西康宝生物制品股份有限公司 | 一种米氮醇的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3190893A (en) * | 1961-02-17 | 1965-06-22 | Kefalas As | Method of producing 9, 10-dihydroanthracenes |
| CH420150A (de) * | 1961-12-18 | 1966-09-15 | Siegfried Ag | Verfahren zur Herstellung von 10-Aminoalkyl-5,5-dialkylacridanen |
| NL129434C (en, 2012) * | 1966-03-12 | |||
| US3808208A (en) * | 1970-02-02 | 1974-04-30 | Dow Chemical Co | P-benzodithino(dioxino)(2,3,-b)pyrazines |
| NL176458C (nl) * | 1972-09-23 | 1985-04-16 | Akzo Nv | Werkwijze ter bereiding van een farmaceutisch preparaat en werkwijze voor de bereiding van daartoe geschikte actieve stoffen. |
| NL179906C (nl) | 1974-02-09 | 1986-12-01 | Akzo Nv | Werkwijze voor het bereiden van 1,2,3,4,10,14b-hexahydrodibenzo(c,f)pyrazino (1,2-a)azepine derivaten. |
| DE2457971A1 (de) * | 1974-12-07 | 1976-06-10 | Merck Patent Gmbh | Verfahren zur herstellung von 2-acyl4-oxo-pyrazino-isochinolin-derivaten |
-
1974
- 1974-02-09 NL NLAANVRAGE7401807,A patent/NL179906C/xx active Search and Examination
-
1975
- 1975-01-28 GB GB39732/76A patent/GB1498633A/en not_active Expired
- 1975-01-28 GB GB3670/75A patent/GB1498632A/en not_active Expired
- 1975-01-30 DK DK032375A patent/DK150144C/da not_active IP Right Cessation
- 1975-02-06 FI FI750327A patent/FI57106C/fi not_active IP Right Cessation
- 1975-02-06 CH CH143875A patent/CH613705A5/xx not_active IP Right Cessation
- 1975-02-06 US US05/547,680 patent/US4025513A/en not_active Expired - Lifetime
- 1975-02-07 ES ES434533A patent/ES434533A1/es not_active Expired
- 1975-02-07 FR FR7503954A patent/FR2260579B1/fr not_active Expired
- 1975-02-07 DE DE19752505239 patent/DE2505239A1/de active Granted
- 1975-02-07 HU HUAO404A patent/HU169018B/hu unknown
- 1975-02-07 JP JP1615675A patent/JPS5315520B2/ja not_active Expired
- 1975-02-07 SE SE7501365A patent/SE418745B/xx not_active IP Right Cessation
- 1975-02-10 CA CA219,742A patent/CA1084490A/en not_active Expired
-
1979
- 1979-08-08 US US06/064,812 patent/US4254031A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FI57106B (fi) | 1980-02-29 |
| DK150144C (da) | 1987-10-19 |
| DE2505239C2 (en, 2012) | 1988-11-03 |
| JPS5315520B2 (en, 2012) | 1978-05-25 |
| DE2505239A1 (de) | 1975-08-14 |
| SE418745B (sv) | 1981-06-22 |
| GB1498633A (en) | 1978-01-25 |
| FI750327A7 (en, 2012) | 1975-08-10 |
| GB1498632A (en) | 1978-01-25 |
| CH613705A5 (en, 2012) | 1979-10-15 |
| FR2260579A1 (en, 2012) | 1975-09-05 |
| FR2260579B1 (en, 2012) | 1977-07-08 |
| US4254031A (en) | 1981-03-03 |
| DK150144B (da) | 1986-12-15 |
| DK32375A (en, 2012) | 1975-09-29 |
| US4025513A (en) | 1977-05-24 |
| NL179906C (nl) | 1986-12-01 |
| SE7501365L (en, 2012) | 1975-08-11 |
| JPS50108299A (en, 2012) | 1975-08-26 |
| HU169018B (en, 2012) | 1976-09-28 |
| CA1084490A (en) | 1980-08-26 |
| ES434533A1 (es) | 1976-12-01 |
| NL7401807A (nl) | 1975-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired | ||
| MA | Patent expired |
Owner name: AKZO N.V. |