NO123950B - - Google Patents
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- Publication number
- NO123950B NO123950B NO168102A NO16810267A NO123950B NO 123950 B NO123950 B NO 123950B NO 168102 A NO168102 A NO 168102A NO 16810267 A NO16810267 A NO 16810267A NO 123950 B NO123950 B NO 123950B
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- ether
- water
- mixture
- ethyl
- Prior art date
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- IVCGJOSPVGENCT-UHFFFAOYSA-N 1h-pyrrolo[2,3-f]quinoline Chemical class N1=CC=CC2=C(NC=C3)C3=CC=C21 IVCGJOSPVGENCT-UHFFFAOYSA-N 0.000 claims description 4
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 192
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 133
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
- 239000000243 solution Substances 0.000 description 79
- 239000000203 mixture Substances 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 65
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 65
- 238000002844 melting Methods 0.000 description 56
- 230000008018 melting Effects 0.000 description 56
- 239000011541 reaction mixture Substances 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000002274 desiccant Substances 0.000 description 33
- 239000012259 ether extract Substances 0.000 description 30
- 238000000605 extraction Methods 0.000 description 30
- -1 3-(N-amino-2-p-chlorophenyl-aminoethyl)-pyridine Chemical compound 0.000 description 28
- 238000010992 reflux Methods 0.000 description 28
- 238000003756 stirring Methods 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- 239000002585 base Substances 0.000 description 25
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 22
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 18
- 238000001914 filtration Methods 0.000 description 18
- 230000001476 alcoholic effect Effects 0.000 description 17
- 238000001035 drying Methods 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 14
- 238000005406 washing Methods 0.000 description 13
- 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 12
- 238000001816 cooling Methods 0.000 description 12
- 239000012065 filter cake Substances 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- 235000010288 sodium nitrite Nutrition 0.000 description 11
- 238000001256 steam distillation Methods 0.000 description 11
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 239000012258 stirred mixture Substances 0.000 description 10
- 239000011701 zinc Substances 0.000 description 10
- 229910052725 zinc Inorganic materials 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000739 antihistaminic agent Substances 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000003513 alkali Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- DFOCNGTYLLIUMY-UHFFFAOYSA-N 1-(3-chloro-4-methylphenyl)-1-[2-(6-methylpyridin-3-yl)ethyl]hydrazine Chemical compound NN(CCC=1C=CC(=NC1)C)C1=CC(=C(C=C1)C)Cl DFOCNGTYLLIUMY-UHFFFAOYSA-N 0.000 description 3
- PSKSGVYXCCVLRN-UHFFFAOYSA-N 1-(3-chlorophenyl)-1-[2-(6-methylpyridin-3-yl)ethyl]hydrazine Chemical compound NN(CCC=1C=CC(=NC1)C)C1=CC(=CC=C1)Cl PSKSGVYXCCVLRN-UHFFFAOYSA-N 0.000 description 3
- WCTGYFWVYBPRGF-UHFFFAOYSA-N 8-chloro-2-methyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CCC1=CC=C(C)N=C1 WCTGYFWVYBPRGF-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000001387 anti-histamine Effects 0.000 description 3
- 229940125715 antihistaminic agent Drugs 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
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000932 sedative agent Substances 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UZLMUZNFTLEJCB-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-1-[2-(6-methylpyridin-3-yl)ethyl]hydrazine Chemical compound NN(CCC=1C=CC(=NC1)C)C1=CC(=C(C=C1)Cl)Cl UZLMUZNFTLEJCB-UHFFFAOYSA-N 0.000 description 2
- VVXMWUPOTBTLFS-UHFFFAOYSA-N 1-(4-bromophenyl)-1-[2-(6-methylpyridin-3-yl)ethyl]hydrazine Chemical compound NN(CCC=1C=CC(=NC1)C)C1=CC=C(C=C1)Br VVXMWUPOTBTLFS-UHFFFAOYSA-N 0.000 description 2
- OBSRPRDPJRYYCJ-UHFFFAOYSA-N 1-(4-chloro-3-methylphenyl)-1-[2-(6-methylpyridin-3-yl)ethyl]hydrazine Chemical compound CC1=NC=C(CCN(N)C2=CC(C)=C(Cl)C=C2)C=C1 OBSRPRDPJRYYCJ-UHFFFAOYSA-N 0.000 description 2
- KVJQCPLFFDQLAE-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-(2-pyridin-3-ylethyl)hydrazine Chemical compound NN(CCC=1C=NC=CC1)C1=CC=C(C=C1)Cl KVJQCPLFFDQLAE-UHFFFAOYSA-N 0.000 description 2
- YLCSXUFYAITZNI-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-[2-(6-methylpyridin-3-yl)ethyl]hydrazine Chemical compound C1=NC(C)=CC=C1CCN(N)C1=CC=C(Cl)C=C1 YLCSXUFYAITZNI-UHFFFAOYSA-N 0.000 description 2
- YYLRIKJTTJUYKH-UHFFFAOYSA-N 3,4-dichloro-N-[2-(6-methylpyridin-3-yl)ethyl]aniline Chemical compound ClC=1C=C(C=CC1Cl)NCCC=1C=CC(=NC1)C YYLRIKJTTJUYKH-UHFFFAOYSA-N 0.000 description 2
- CDPANQNDRJGXBA-UHFFFAOYSA-N 3-chloro-4-methyl-N-[2-(6-methylpyridin-3-yl)ethyl]aniline Chemical compound ClC=1C=C(C=CC1C)NCCC=1C=CC(=NC1)C CDPANQNDRJGXBA-UHFFFAOYSA-N 0.000 description 2
- GLLXMWHRHHGOJA-UHFFFAOYSA-N 3-methyl-N-[2-(6-methylpyridin-3-yl)ethyl]aniline Chemical compound CC=1C=C(C=CC1)NCCC=1C=CC(=NC1)C GLLXMWHRHHGOJA-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
- BAGBJDAEDJUIPC-UHFFFAOYSA-N 4-chloro-2-methyl-N-[2-(6-methylpyridin-3-yl)ethyl]aniline Chemical compound ClC1=CC(=C(C=C1)NCCC=1C=CC(=NC1)C)C BAGBJDAEDJUIPC-UHFFFAOYSA-N 0.000 description 2
- GYRLUWCDFYCBRF-UHFFFAOYSA-N 4-chloro-3-methyl-N-[2-(6-methylpyridin-3-yl)ethyl]aniline Chemical compound ClC1=C(C=C(C=C1)NCCC=1C=CC(=NC1)C)C GYRLUWCDFYCBRF-UHFFFAOYSA-N 0.000 description 2
- MTPAWVOOQNRJLS-UHFFFAOYSA-N 4-chloro-n-(2-pyridin-3-ylethyl)aniline Chemical compound C1=CC(Cl)=CC=C1NCCC1=CC=CN=C1 MTPAWVOOQNRJLS-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- VTKZTRPPURXIRX-UHFFFAOYSA-N 8-chloro-2-methyl-5-(2-pyridin-3-ylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CCC1=CC=CN=C1 VTKZTRPPURXIRX-UHFFFAOYSA-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- ZUOGTLCZINBJEV-UHFFFAOYSA-N N-(3,4-dichlorophenyl)-N-[2-(6-methylpyridin-3-yl)ethyl]nitrous amide Chemical compound N(=O)N(CCC=1C=CC(=NC1)C)C1=CC(=C(C=C1)Cl)Cl ZUOGTLCZINBJEV-UHFFFAOYSA-N 0.000 description 2
- GAVHLPRQAGQQIZ-UHFFFAOYSA-N N-(3-chlorophenyl)-N-[2-(6-methylpyridin-3-yl)ethyl]nitrous amide Chemical compound N(=O)N(CCC=1C=CC(=NC1)C)C1=CC(=CC=C1)Cl GAVHLPRQAGQQIZ-UHFFFAOYSA-N 0.000 description 2
- VJQHOYVLHYOFQE-UHFFFAOYSA-N N-(4-bromophenyl)-N-[2-(6-methylpyridin-3-yl)ethyl]nitrous amide Chemical compound CC1=NC=C(C=C1)CCN(C1=CC=C(C=C1)Br)N=O VJQHOYVLHYOFQE-UHFFFAOYSA-N 0.000 description 2
- BDYDGSGMJKUBON-UHFFFAOYSA-N N-(4-chloro-3-methylphenyl)-N-[2-(6-methylpyridin-3-yl)ethyl]nitrous amide Chemical compound N(=O)N(CCC=1C=CC(=NC1)C)C1=CC(=C(C=C1)Cl)C BDYDGSGMJKUBON-UHFFFAOYSA-N 0.000 description 2
- KXDZUJPEEKYFCF-UHFFFAOYSA-N N-(4-chlorophenyl)-N-(2-pyridin-3-ylethyl)nitrous amide Chemical compound N(=O)N(CCC=1C=NC=CC1)C1=CC=C(C=C1)Cl KXDZUJPEEKYFCF-UHFFFAOYSA-N 0.000 description 2
- LDFSGQYIUXSSSJ-UHFFFAOYSA-N N-(4-chlorophenyl)-N-[2-(6-methylpyridin-3-yl)ethyl]nitrous amide Chemical compound CC1=NC=C(C=C1)CCN(N=O)C1=CC=C(C=C1)Cl LDFSGQYIUXSSSJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000009935 nitrosation Effects 0.000 description 2
- 238000007034 nitrosation reaction Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XEKJENRJCYALFH-UHFFFAOYSA-N 1-(3-methylphenyl)-1-[2-(6-methylpyridin-3-yl)ethyl]hydrazine Chemical compound NN(CCC=1C=CC(=NC1)C)C1=CC(=CC=C1)C XEKJENRJCYALFH-UHFFFAOYSA-N 0.000 description 1
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
- ZKDOPVZRQPOILA-UHFFFAOYSA-N 2,7,8-trimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=C(C)C=C1N2CCC1=CC=C(C)N=C1 ZKDOPVZRQPOILA-UHFFFAOYSA-N 0.000 description 1
- FIXBEWPJUGFHOF-UHFFFAOYSA-N 2,8,9-trimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=C(C)C(C)=CC=C1N2CCC1=CC=C(C)N=C1 FIXBEWPJUGFHOF-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RQKFYFNZSHWXAW-UHFFFAOYSA-N 3-chloro-p-toluidine Chemical compound CC1=CC=C(N)C=C1Cl RQKFYFNZSHWXAW-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- DPZYLEIWHTWHCU-UHFFFAOYSA-N 3-ethenylpyridine Chemical compound C=CC1=CC=CN=C1 DPZYLEIWHTWHCU-UHFFFAOYSA-N 0.000 description 1
- BSPGIYWSXHSTSE-UHFFFAOYSA-N 4-bromo-N-[2-(6-methylpyridin-3-yl)ethyl]aniline Chemical compound BrC1=CC=C(C=C1)NCCC=1C=CC(=NC1)C BSPGIYWSXHSTSE-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- HIHCTGNZNHSZPP-UHFFFAOYSA-N 4-chloro-3-methylaniline Chemical compound CC1=CC(N)=CC=C1Cl HIHCTGNZNHSZPP-UHFFFAOYSA-N 0.000 description 1
- REWTVEJXHXEYFW-UHFFFAOYSA-N 4-chloro-N-[2-(6-methylpyridin-3-yl)ethyl]aniline Chemical compound ClC1=CC=C(NCCC2=CN=C(C=C2)C)C=C1 REWTVEJXHXEYFW-UHFFFAOYSA-N 0.000 description 1
- NDRMMXJIUIBLRB-UHFFFAOYSA-N 7-chloro-2,8-dimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=C(Cl)C=C1N2CCC1=CC=C(C)N=C1 NDRMMXJIUIBLRB-UHFFFAOYSA-N 0.000 description 1
- QEMPEDFSDYTWEF-UHFFFAOYSA-N 7-chloro-2-methyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC=C(Cl)C=C1N2CCC1=CC=C(C)N=C1 QEMPEDFSDYTWEF-UHFFFAOYSA-N 0.000 description 1
- TZGDTVFCMRLOMM-UHFFFAOYSA-N 8-chloro-2,7-dimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(Cl)=C(C)C=C1N2CCC1=CC=C(C)N=C1 TZGDTVFCMRLOMM-UHFFFAOYSA-N 0.000 description 1
- XGGILFZLGXIRFW-UHFFFAOYSA-N 8-chloro-2-methyl-5-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1h-pyrido[4,3-b]indole;dihydrochloride Chemical compound Cl.Cl.C1N(C)CCC2=C1C1=CC(Cl)=CC=C1N2CCC1=CC=C(C)N=C1 XGGILFZLGXIRFW-UHFFFAOYSA-N 0.000 description 1
- WMDNXNVKDYMBGY-UHFFFAOYSA-N 8-methyl-5-[2-(6-methylpyridin-3-yl)ethyl]-1,2,3,4-tetrahydropyrido[4,3-b]indole;dihydrochloride Chemical compound Cl.Cl.C1=2CCNCC=2C2=CC(C)=CC=C2N1CCC1=CC=C(C)N=C1 WMDNXNVKDYMBGY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010002199 Anaphylactic shock Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000003326 anti-histaminergic effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 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
- 239000012298 atmosphere Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 210000004013 groin Anatomy 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54945566A | 1966-05-12 | 1966-05-12 | |
| US628530A US3409628A (en) | 1966-05-12 | 1967-04-05 | 5-(3-pyridylethyl)pyridoindole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123950B true NO123950B (en:Method) | 1972-02-07 |
Family
ID=27069138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO168102A NO123950B (en:Method) | 1966-05-12 | 1967-05-11 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3409628A (en:Method) |
| BE (1) | BE698183A (en:Method) |
| CH (1) | CH494234A (en:Method) |
| DE (1) | DE1695187A1 (en:Method) |
| DK (1) | DK123655B (en:Method) |
| ES (1) | ES340412A1 (en:Method) |
| FI (1) | FI48093C (en:Method) |
| FR (2) | FR7024M (en:Method) |
| GB (3) | GB1173997A (en:Method) |
| IL (1) | IL27956A (en:Method) |
| NL (1) | NL6706671A (en:Method) |
| NO (1) | NO123950B (en:Method) |
| SE (1) | SE342231B (en:Method) |
| YU (1) | YU94367A (en:Method) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4696930A (en) * | 1985-04-12 | 1987-09-29 | Hoffmann-La Roche Inc. | N-(heteroarylalkyl)acylanilide derivatives as antiarrhythmic agents |
| RU2339637C1 (ru) * | 2007-04-05 | 2008-11-27 | Андрей Александрович Иващенко | Блокаторы гистаминного рецептора для фармацевтических композиций, обладающих противоаллергическим и аутоиммунным действием |
| CA2700160A1 (en) * | 2007-09-20 | 2009-03-26 | D2E, Llc | Fluoro-containing derivatives of hydrogenated pyrido[4,3-b]indoles with neuroprotective and cognition enhancing properties, process for preparing, and use |
| RU2007139634A (ru) | 2007-10-25 | 2009-04-27 | Сергей Олегович Бачурин (RU) | Новые тиазол-, триазол- или оксадиазол-содержащие тетрациклические соединения |
| WO2009082268A2 (ru) * | 2007-12-21 | 2009-07-02 | Alla Chem, Llc | ЛИГАНДЫ α-АДРЕНОЦЕПТОРОВ, ДОПАМИНОВЫХ, ГИСТАМИНОВЫХ, ИМИДАЗОЛИНОВЫХ И СЕРОТОНИНОВЫХ РЕЦЕПТОРОВ И ИХ ПРИМЕНЕНИЕ |
| US9063126B2 (en) * | 2008-09-29 | 2015-06-23 | Abbvie Inc. | Indole and indoline derivatives and methods of use thereof |
| US9625475B2 (en) * | 2008-09-29 | 2017-04-18 | Abbvie Inc. | Indole and indoline derivatives and methods of use thereof |
| WO2010067085A2 (en) | 2008-12-12 | 2010-06-17 | Wista Laboratories Ltd. | Synthesis of 9-(arylalkyl)-1,2,3,4-tetrahydro-υ-carboline and analogues and intermediates |
| US9162980B2 (en) | 2009-01-09 | 2015-10-20 | Board Of Regents Of The University Of Texas System | Anti-depression compounds |
| US8362277B2 (en) | 2009-01-09 | 2013-01-29 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| US9962368B2 (en) | 2009-01-09 | 2018-05-08 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| CN107595841A (zh) * | 2009-01-09 | 2018-01-19 | 得克萨斯州大学系统董事会 | 前神经原性化合物 |
| BRPI1006602A2 (pt) | 2009-04-29 | 2019-01-15 | Medivation Technologies Inc | composto, método para modular um receptor de histamina em um indivíduo, composição farmacêutica, kit e método para tratar um distúrbio cognitivo ou um distúrbio induzido por pelo menos um sintoma associado com a alteração da cognição |
| AU2010282990B2 (en) | 2009-04-29 | 2015-11-05 | Medivation Technologies, Inc. | Pyrido [4, 3-b] indoles and methods of use |
| WO2011008312A2 (en) | 2009-07-14 | 2011-01-20 | Abbott Laboratories | Indole and indoline derivatives and methods of use thereof |
| EP2590647B1 (en) | 2010-07-07 | 2017-11-08 | Board of Regents of the University of Texas System | Pro-neurogenic compounds |
| US8791132B2 (en) | 2011-02-18 | 2014-07-29 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| CA2882826A1 (en) | 2012-08-24 | 2014-02-27 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| WO2015070237A1 (en) | 2013-11-11 | 2015-05-14 | Board Of Regents Of The University Of Texas System | Neuroprotective chemicals and methods for identifying and using same |
| WO2015070234A2 (en) | 2013-11-11 | 2015-05-14 | Board Of Regents Of The University Of Texas System | Neuroprotective compounds and use thereof |
| US12084440B2 (en) * | 2021-02-01 | 2024-09-10 | Bigespas Ltd. | Polymorph of latrepirdine dihydrochloride |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2786059A (en) * | 1951-04-30 | 1957-03-19 | Schenley Ind Inc | Derivatives of 2-nu-methyl-1, 2, 3, 4-tetrahydro-gamma-carbolines |
-
1967
- 1967-04-05 US US628530A patent/US3409628A/en not_active Expired - Lifetime
- 1967-05-02 CH CH632467A patent/CH494234A/de not_active IP Right Cessation
- 1967-05-05 DE DE19671695187 patent/DE1695187A1/de active Pending
- 1967-05-09 FR FR105641A patent/FR7024M/fr not_active Expired
- 1967-05-09 BE BE698183D patent/BE698183A/xx unknown
- 1967-05-09 FR FR105640A patent/FR1522686A/fr not_active Expired
- 1967-05-10 IL IL27956A patent/IL27956A/en unknown
- 1967-05-11 NO NO168102A patent/NO123950B/no unknown
- 1967-05-11 ES ES340412A patent/ES340412A1/es not_active Expired
- 1967-05-11 GB GB21874/67A patent/GB1173997A/en not_active Expired
- 1967-05-11 GB GB29346/69A patent/GB1173999A/en not_active Expired
- 1967-05-11 YU YU00943/67A patent/YU94367A/xx unknown
- 1967-05-11 GB GB29345/69A patent/GB1173998A/en not_active Expired
- 1967-05-11 DK DK249367AA patent/DK123655B/da unknown
- 1967-05-12 SE SE6699/67A patent/SE342231B/xx unknown
- 1967-05-12 NL NL6706671A patent/NL6706671A/xx unknown
- 1967-05-12 FI FI671366A patent/FI48093C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| YU94367A (en) | 1974-08-31 |
| GB1173997A (en) | 1969-12-10 |
| SE342231B (en:Method) | 1972-01-31 |
| BE698183A (en:Method) | 1967-11-09 |
| FR1522686A (fr) | 1968-04-26 |
| CH494234A (de) | 1970-07-31 |
| FR7024M (en:Method) | 1969-06-09 |
| FI48093B (en:Method) | 1974-02-28 |
| ES340412A1 (es) | 1968-06-01 |
| GB1173999A (en) | 1969-12-10 |
| FI48093C (fi) | 1974-06-10 |
| GB1173998A (en) | 1969-12-10 |
| NL6706671A (en:Method) | 1967-11-13 |
| DK123655B (da) | 1972-07-17 |
| US3409628A (en) | 1968-11-05 |
| IL27956A (en) | 1972-06-28 |
| DE1695187A1 (de) | 1971-04-08 |
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