DK141501B - Analogifremgangsmåde til fremstilling af aminosubstituerede tetracykliske forbindelser eller syreadditionssalte eller kvaternære alkylammoniumsalte deraf. - Google Patents
Analogifremgangsmåde til fremstilling af aminosubstituerede tetracykliske forbindelser eller syreadditionssalte eller kvaternære alkylammoniumsalte deraf. Download PDFInfo
- Publication number
- DK141501B DK141501B DK235774AA DK235774A DK141501B DK 141501 B DK141501 B DK 141501B DK 235774A A DK235774A A DK 235774AA DK 235774 A DK235774 A DK 235774A DK 141501 B DK141501 B DK 141501B
- Authority
- DK
- Denmark
- Prior art keywords
- tribenzo
- tetrahydro
- compound
- general formula
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 60
- 239000002253 acid Substances 0.000 title claims description 11
- 150000003839 salts Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 125000005210 alkyl ammonium group Chemical group 0.000 title claims description 4
- 125000003277 amino group Chemical group 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 230000002829 reductive effect Effects 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 101150115538 nero gene Proteins 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 34
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 34
- 239000000203 mixture Substances 0.000 description 32
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- -1 p-bromophenylsulfonyl Chemical group 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 13
- 238000006722 reduction reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 150000003840 hydrochlorides Chemical class 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 229910004298 SiO 2 Inorganic materials 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 229910052987 metal hydride Inorganic materials 0.000 description 6
- 150000004681 metal hydrides Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 150000005671 trienes Chemical class 0.000 description 6
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- GPMBKTLUACIDNQ-UHFFFAOYSA-N N,N-dimethyl-14-thiatetracyclo[13.4.0.02,7.08,13]nonadeca-1(19),2(7),8,10,12,15,17-heptaen-4-amine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1CC(N(C)C)CC2 GPMBKTLUACIDNQ-UHFFFAOYSA-N 0.000 description 5
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 5
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 5
- 229960003147 reserpine Drugs 0.000 description 5
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 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 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- HMBYRDQQSGRBKS-UHFFFAOYSA-N 14-thiatetracyclo[13.4.0.02,7.08,13]nonadeca-1(19),2(7),8,10,12,15,17-heptaen-4-amine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1CC(N)CC2 HMBYRDQQSGRBKS-UHFFFAOYSA-N 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 150000002923 oximes Chemical group 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- USKZHEQYENVSMH-YDFGWWAZSA-N 1,3,5-Heptatriene Chemical compound C\C=C\C=C\C=C USKZHEQYENVSMH-YDFGWWAZSA-N 0.000 description 2
- OGWYSEYYVRQVON-UHFFFAOYSA-N 10-chloro-14-oxatetracyclo[13.4.0.02,7.08,13]nonadeca-1(19),2(7),8(13),9,11,15,17-heptaen-4-one Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1CCC(=O)C2 OGWYSEYYVRQVON-UHFFFAOYSA-N 0.000 description 2
- LWEAFPLTFMXYTF-UHFFFAOYSA-N 17-methyl-14-oxatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),2(7),8,10,12,16,18-heptaen-4-amine Chemical compound C12=CC=CC=C2OC2=CC(C)=CC=C2C2=C1CCC(N)C2 LWEAFPLTFMXYTF-UHFFFAOYSA-N 0.000 description 2
- OAHLQOHOFVFQJO-UHFFFAOYSA-N 18-chloro-N,N-dimethyl-14-oxatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),2(7),8,10,12,16,18-heptaen-4-amine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1CC(N(C)C)CC2 OAHLQOHOFVFQJO-UHFFFAOYSA-N 0.000 description 2
- TVQCEDVDEJJJBZ-UHFFFAOYSA-N 2-amino-1,2,3,4-tetrahydro-tribenzo(b,d,f)-oxepine Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1CC(N)CC2 TVQCEDVDEJJJBZ-UHFFFAOYSA-N 0.000 description 2
- DNVHBMZYUMNNPQ-UHFFFAOYSA-N 2-azido-1,2,3,4-tetrahydro-tribenzo(b,d,f)-oxepine Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1CC(N=[N+]=[N-])CC2 DNVHBMZYUMNNPQ-UHFFFAOYSA-N 0.000 description 2
- OSHFAZOPYSTYOK-UHFFFAOYSA-N 2-keto-1,2,3,4-tetrahydro-tribenzo(b,d,f)-oxepine Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1CC(=O)CC2 OSHFAZOPYSTYOK-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- 229910010084 LiAlH4 Inorganic materials 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- YLCBSQDZXZLURN-UHFFFAOYSA-N N,N,14-trimethyl-14-azatetracyclo[13.4.0.02,7.08,13]nonadeca-1(19),2(7),8,10,12,15,17-heptaen-4-amine Chemical compound C12=CC=CC=C2N(C)C2=CC=CC=C2C2=C1CC(N(C)C)CC2 YLCBSQDZXZLURN-UHFFFAOYSA-N 0.000 description 2
- XOUKATHDTROITC-UHFFFAOYSA-N N,N-dimethyl-14-oxatetracyclo[13.4.0.02,7.08,13]nonadeca-1(19),2(7),8,10,12,15,17-heptaen-4-amine Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1CC(N(C)C)CC2 XOUKATHDTROITC-UHFFFAOYSA-N 0.000 description 2
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002825 nitriles Chemical group 0.000 description 2
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000006268 reductive amination reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- KWTSXDURSIMDCE-UHFFFAOYSA-N 1-phenylpropan-2-amine Chemical compound CC(N)CC1=CC=CC=C1 KWTSXDURSIMDCE-UHFFFAOYSA-N 0.000 description 1
- SFSNITSBOBIVIG-UHFFFAOYSA-N 10-methyl-14-oxatetracyclo[13.4.0.02,7.08,13]nonadeca-1(19),2(7),8(13),9,11,15,17-heptaen-4-one Chemical compound C12=CC(C)=CC=C2OC2=CC=CC=C2C2=C1CCC(=O)C2 SFSNITSBOBIVIG-UHFFFAOYSA-N 0.000 description 1
- XFFBGRCZGWAYCT-UHFFFAOYSA-N 14-methyl-14-azatetracyclo[13.4.0.02,7.08,13]nonadeca-1(19),2(7),8,10,12,15,17-heptaen-4-amine Chemical compound C12=CC=CC=C2N(C)C2=CC=CC=C2C2=C1CC(N)CC2 XFFBGRCZGWAYCT-UHFFFAOYSA-N 0.000 description 1
- YXKXNGZYRILUKO-UHFFFAOYSA-N 14-methyl-14-azatetracyclo[13.4.0.02,7.08,13]nonadeca-1(19),8,10,12,15,17-hexaen-4-amine Chemical compound CN1C2=CC=CC=C2C2CCC(N)CC2C2=CC=CC=C12 YXKXNGZYRILUKO-UHFFFAOYSA-N 0.000 description 1
- GVMNVXIYFBDGQR-UHFFFAOYSA-N 14-methyl-4-piperidin-1-yl-14-azatetracyclo[13.4.0.02,7.08,13]nonadeca-1(19),2(7),8,10,12,15,17-heptaene Chemical compound C12=CC=CC=C2N(C)C2=CC=CC=C2C(CC2)=C1CC2N1CCCCC1 GVMNVXIYFBDGQR-UHFFFAOYSA-N 0.000 description 1
- IJOBWDOYRCWDEW-UHFFFAOYSA-N 14-thiatetracyclo[13.4.0.02,7.08,13]nonadeca-1(19),2(7),8,10,12,15,17-heptaen-4-one Chemical compound C12=CC=CC=C2SC2=CC=CC=C2C2=C1CC(=O)CC2 IJOBWDOYRCWDEW-UHFFFAOYSA-N 0.000 description 1
- NPMGMYXPOQNMLA-UHFFFAOYSA-N 17-methyl-14-oxatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),2(7),8,10,12,16,18-heptaen-4-one Chemical compound C12=CC=CC=C2OC2=CC(C)=CC=C2C2=C1CCC(=O)C2 NPMGMYXPOQNMLA-UHFFFAOYSA-N 0.000 description 1
- ZGPPFIZIJFVMSG-UHFFFAOYSA-N 18-chloro-14-oxatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),2(7),8,10,12,16,18-heptaen-4-amine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1CC(N)CC2 ZGPPFIZIJFVMSG-UHFFFAOYSA-N 0.000 description 1
- WLICLIPHZLDJFZ-UHFFFAOYSA-N 18-chloro-14-oxatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),2(7),8,10,12,16,18-heptaen-4-one Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C2=C1CC(=O)CC2 WLICLIPHZLDJFZ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ZUIUDKSRNXAJFW-UHFFFAOYSA-N 2-hydroxy-1,2,3,4-tetrahydro-tribenzo(b,d,f)-oxepine Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1CC(O)CC2 ZUIUDKSRNXAJFW-UHFFFAOYSA-N 0.000 description 1
- KGSQSQUMYYPPCF-UHFFFAOYSA-N 2-mesyloxy-1,2,3,4-tetrahydro-tribenzo(b,d,f)-oxepine Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C2=C1CC(OS(=O)(=O)C)CC2 KGSQSQUMYYPPCF-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 238000006824 Eschweiler-Clarke methylation reaction Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- KKEIIYDENQRDAR-UHFFFAOYSA-N N,N,10-trimethyl-14-oxatetracyclo[13.4.0.02,7.08,13]nonadeca-1(19),2(7),8(13),9,11,15,17-heptaen-4-amine Chemical compound C12=CC=CC=C2OC2=CC=C(C)C=C2C2=C1CC(N(C)C)CC2 KKEIIYDENQRDAR-UHFFFAOYSA-N 0.000 description 1
- ZNQWFPKQOWSHSN-UHFFFAOYSA-N N,N,17,18-tetramethyl-14-oxatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),2(7),8,10,12,16,18-heptaen-4-amine Chemical compound C12=CC(C)=C(C)C=C2OC2=CC=CC=C2C2=C1CC(N(C)C)CC2 ZNQWFPKQOWSHSN-UHFFFAOYSA-N 0.000 description 1
- MRXDCMZJADVHFH-UHFFFAOYSA-N N,N,17-trimethyl-14-oxatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),2(7),8,10,12,16,18-heptaen-4-amine Chemical compound C12=CC=C(C)C=C2OC2=CC=CC=C2C2=C1CC(N(C)C)CC2 MRXDCMZJADVHFH-UHFFFAOYSA-N 0.000 description 1
- QPCKBCIYAPYPDZ-UHFFFAOYSA-N N,N-dimethyl-17-(trifluoromethyl)-14-oxatetracyclo[13.4.0.02,7.08,13]nonadeca-1(15),2(7),8,10,12,16,18-heptaen-4-amine Chemical compound C12=CC=C(C(F)(F)F)C=C2OC2=CC=CC=C2C2=C1CC(N(C)C)CC2 QPCKBCIYAPYPDZ-UHFFFAOYSA-N 0.000 description 1
- 229910020886 NaBH2 Inorganic materials 0.000 description 1
- 229910020889 NaBH3 Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 150000008064 anhydrides 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
- 239000002585 base Substances 0.000 description 1
- QQQCGYCZORNOOS-UHFFFAOYSA-N benzo[b][1]benzoxepine Chemical compound C1=CC2=CC=CC=C2OC2=CC=CC=C21 QQQCGYCZORNOOS-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- CHVJITGCYZJHLR-UHFFFAOYSA-N cyclohepta-1,3,5-triene Chemical compound C1C=CC=CC=C1 CHVJITGCYZJHLR-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- NKRNGKIEDAVMHL-UHFFFAOYSA-L dihydroxy(dioxo)chromium;pyridine Chemical compound O[Cr](O)(=O)=O.C1=CC=NC=C1 NKRNGKIEDAVMHL-UHFFFAOYSA-L 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- USKZHEQYENVSMH-UHFFFAOYSA-N hepta-1,3,5-triene Chemical compound CC=CC=CC=C USKZHEQYENVSMH-UHFFFAOYSA-N 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 238000003328 mesylation reaction Methods 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 230000003470 muricidal effect Effects 0.000 description 1
- 239000003773 muricide Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- PZHNNJXWQYFUTD-UHFFFAOYSA-N phosphorus triiodide Chemical compound IP(I)I PZHNNJXWQYFUTD-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 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 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7306069 | 1973-05-02 | ||
| NL7306069A NL7306069A (en, 2012) | 1973-05-02 | 1973-05-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141501B true DK141501B (da) | 1980-03-31 |
| DK141501C DK141501C (en, 2012) | 1980-09-22 |
Family
ID=19818770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK235774AA DK141501B (da) | 1973-05-02 | 1974-04-30 | Analogifremgangsmåde til fremstilling af aminosubstituerede tetracykliske forbindelser eller syreadditionssalte eller kvaternære alkylammoniumsalte deraf. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3950425A (en, 2012) |
| JP (1) | JPS5035153A (en, 2012) |
| BE (1) | BE814467A (en, 2012) |
| CH (3) | CH619683A5 (en, 2012) |
| DE (1) | DE2420964A1 (en, 2012) |
| DK (1) | DK141501B (en, 2012) |
| ES (1) | ES425809A1 (en, 2012) |
| FR (1) | FR2227870B1 (en, 2012) |
| GB (1) | GB1461834A (en, 2012) |
| HU (1) | HU170767B (en, 2012) |
| IE (1) | IE39229B1 (en, 2012) |
| NL (1) | NL7306069A (en, 2012) |
| SE (2) | SE403373B (en, 2012) |
| ZA (1) | ZA742542B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4054572A (en) * | 1973-04-26 | 1977-10-18 | Akzona Incorporated | Hexahydro pyridine [1,2d] dibenza [b,f] (1,4)-diazepines |
| US4016161A (en) * | 1974-04-24 | 1977-04-05 | Akzona Incorporated | Amino-substituted 1,2,3,4,10,146-hexahydro-pyridino[1,2-a]dibenzo[c,f]azepines |
| US4038299A (en) * | 1975-05-30 | 1977-07-26 | Syntex (U.S.A.) Inc. | 2-Substituted-5-oxo-5H-dibenzo [a,d] -cycloheptene esters |
| CA1087174A (en) * | 1976-12-08 | 1980-10-07 | Atsuyuki Kojima | Tetracyclic compounds and production thereof |
| SE7902647L (sv) * | 1979-03-23 | 1980-09-24 | Astra Laekemedel Ab | Nya spirocykoalkylaminer |
| NL8003141A (nl) * | 1980-05-30 | 1982-01-04 | Akzo Nv | Biologisch aktieve tricyclische aminen. |
| US5264577A (en) * | 1992-04-22 | 1993-11-23 | Warner-Lambert Company | Cyclic amino acids and derivatives thereof |
| PL199016B1 (pl) † | 2002-06-20 | 2008-08-29 | Adamed Sp Z Oo | Sposób wytwarzania olanzapiny |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE361306B (en, 2012) * | 1971-06-11 | 1973-10-29 | Astra Laekemedel Ab |
-
1973
- 1973-05-02 NL NL7306069A patent/NL7306069A/xx not_active Application Discontinuation
-
1974
- 1974-04-19 GB GB1734374A patent/GB1461834A/en not_active Expired
- 1974-04-22 ZA ZA00742542A patent/ZA742542B/xx unknown
- 1974-04-22 IE IE855/74A patent/IE39229B1/xx unknown
- 1974-04-24 US US05/463,636 patent/US3950425A/en not_active Expired - Lifetime
- 1974-04-30 SE SE7405804A patent/SE403373B/xx unknown
- 1974-04-30 HU HU74AO00000383A patent/HU170767B/hu unknown
- 1974-04-30 CH CH592274A patent/CH619683A5/de not_active IP Right Cessation
- 1974-04-30 DE DE2420964A patent/DE2420964A1/de not_active Withdrawn
- 1974-04-30 DK DK235774AA patent/DK141501B/da unknown
- 1974-04-30 ES ES425809A patent/ES425809A1/es not_active Expired
- 1974-05-01 JP JP49049234A patent/JPS5035153A/ja active Pending
- 1974-05-02 FR FR7415284A patent/FR2227870B1/fr not_active Expired
- 1974-05-02 BE BE143849A patent/BE814467A/xx unknown
-
1977
- 1977-01-13 SE SE7700287A patent/SE424322B/xx unknown
-
1978
- 1978-06-21 CH CH675678A patent/CH615412A5/de not_active IP Right Cessation
- 1978-06-21 CH CH675778A patent/CH616141A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7306069A (en, 2012) | 1974-11-05 |
| DK141501C (en, 2012) | 1980-09-22 |
| US3950425A (en) | 1976-04-13 |
| HU170767B (hu) | 1977-09-28 |
| FR2227870A1 (en, 2012) | 1974-11-29 |
| IE39229B1 (en) | 1978-08-30 |
| CH619683A5 (en, 2012) | 1980-10-15 |
| FR2227870B1 (en, 2012) | 1978-07-21 |
| SE403373B (sv) | 1978-08-14 |
| DE2420964A1 (de) | 1974-11-21 |
| ZA742542B (en) | 1975-04-30 |
| BE814467A (fr) | 1974-11-04 |
| SE424322B (sv) | 1982-07-12 |
| ES425809A1 (es) | 1976-07-01 |
| IE39229L (en) | 1974-11-02 |
| SE7700287L (sv) | 1977-01-13 |
| JPS5035153A (en, 2012) | 1975-04-03 |
| CH616141A5 (en, 2012) | 1980-03-14 |
| CH615412A5 (en, 2012) | 1980-01-31 |
| GB1461834A (en) | 1977-01-19 |
| AU6828074A (en) | 1975-10-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| He et al. | Metal-free photocatalyzed aerobic oxidative C sp3–H functionalization of glycine derivatives: One-step generation of quinoline-fused lactones | |
| NO320970B1 (no) | Piperazin- og piperidinforbindelse, fremgangsmate for fremstilling derav, farmasoytiske sammensetninger som innbefatter slike forbindelser, fremgangsmate for fremstilling av de nevnte farmasoytiske sammensetninger, samt anvendelse av disse for behandling av CNS-forstyrrelser | |
| EP0908458B1 (en) | Substituted pyridylmethylpiperazine and piperidine derivatives, their preparation and their use for treating central nervous system (CNS) disorders | |
| Cava et al. | An improved photochemical aporphine synthesis: New syntheses of dicentrine and cassameridine | |
| SU688127A3 (ru) | Способ получени фенилэтиламинов или их солей | |
| NO342589B1 (no) | Fremgangsmåte for fremstilling av tetrazol-metansulfonsyresalter og ny forbindelse som anvendes i denne | |
| DK141501B (da) | Analogifremgangsmåde til fremstilling af aminosubstituerede tetracykliske forbindelser eller syreadditionssalte eller kvaternære alkylammoniumsalte deraf. | |
| NZ522017A (en) | A pyridine-1-oxide derivative, and process for its transformation into pharmaceutically effective compounds | |
| JPH01100167A (ja) | ２−［（４−ピペリジル）メチル］−１，２，３，４−テトラヒドロイソキノリン誘導体 | |
| CN105503903A (zh) | 苯并恶唑并恶嗪酮类化合物的制备方法及其中间体和晶型 | |
| FI63014C (fi) | Foer framstaellning av nya farmakologiskt aktiva aminobensocykloheptenderivat och deras salter avsedda 5-hydroxi- och 5-oxo-6,7,8,9-tetrahydroaminobensocykloheptenderivat och deras salter | |
| EP1233961B1 (de) | Verfahren zur herstellung von 5-(1-piperazinyl)-benzofuran-2-carboxamid durch übergansmetall-katalysierte aminierung | |
| Le Gall et al. | Electrosynthesis of α‐aminonitriles: anodic cyanation of N‐substituted tetrahydroquinolines and N‐phenylpiperidines | |
| US3271396A (en) | Pyrido-quinazoline derivatives | |
| Huckle et al. | 4-Amino-2, 3, 4, 5-tetrahydro-1-benzoxepin-5-ols, 4-amino-2, 3, 4, 5-tetrahydro-1-benzothiepin-5-ols, and related compounds | |
| FI76075B (fi) | Foerfarande foer framstaellning av farmaceutiskt vaerdefulla bensazepinderivat. | |
| WO2006046131A1 (en) | Tetralin histamine-3 receptor antagonists | |
| Barluenga et al. | 2-Aza 1, 3-dienes: a new and simple method for the synthesis of functionalized pyridine derivatives | |
| DK142322B (da) | Analogifremgangsmåde til fremstilling af aminosubstituerede piperidinderivater. | |
| CZ294957B6 (cs) | Způsob přípravy substituované imidazopyridinové sloučeniny | |
| MXPA06015267A (es) | Antagonistas diazabiciclicos del receptor histamina-3. | |
| US4062840A (en) | Amino-substituted 1,2,3,4-tetrahydro-9H-tribenzo[b,d,f]azepines | |
| ELDERFIELD et al. | SYNTHESIS OF 1-AMINOPHENAZINES AND CONVERSION OF THEM TO POTENTIAL ANTIMALARIALS1 | |
| CN116396272B (zh) | 一种2,5-二氢吡咯烷类衍生物及消旋尼古丁的制备方法 | |
| US4054572A (en) | Hexahydro pyridine [1,2d] dibenza [b,f] (1,4)-diazepines |