DE1110159B - Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminonorcamphanderivate bzw. von deren Saeureadditionssalzen und quaternaeren Ammoniumverbindungen - Google Patents
Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminonorcamphanderivate bzw. von deren Saeureadditionssalzen und quaternaeren AmmoniumverbindungenInfo
- Publication number
- DE1110159B DE1110159B DEM42332A DEM0042332A DE1110159B DE 1110159 B DE1110159 B DE 1110159B DE M42332 A DEM42332 A DE M42332A DE M0042332 A DEM0042332 A DE M0042332A DE 1110159 B DE1110159 B DE 1110159B
- Authority
- DE
- Germany
- Prior art keywords
- heptane
- ether
- phenyl
- reaction
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 N-substituted amino Chemical group 0.000 title claims description 18
- 239000002253 acid Substances 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 12
- 150000003839 salts Chemical class 0.000 title claims description 10
- 150000003856 quaternary ammonium compounds Chemical class 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims 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 claims description 4
- 239000007868 Raney catalyst Substances 0.000 claims description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 150000003141 primary amines Chemical class 0.000 claims description 3
- 238000005956 quaternization reaction Methods 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 72
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000002585 base Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 12
- 239000000155 melt Substances 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 5
- 229910003446 platinum oxide Inorganic materials 0.000 description 5
- 239000002262 Schiff base Substances 0.000 description 4
- 150000004753 Schiff bases Chemical class 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000003555 analeptic effect Effects 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000002269 analeptic agent Substances 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ODUJIHDQKMHMCH-UHFFFAOYSA-N 1-(3-phenyl-2-bicyclo[2.2.1]heptanyl)pyrrolidine Chemical compound C1(=CC=CC=C1)C1C2CCC(C1N1CCCC1)C2 ODUJIHDQKMHMCH-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- PIAOLBVUVDXHHL-UHFFFAOYSA-N 2-nitroethenylbenzene Chemical class [O-][N+](=O)C=CC1=CC=CC=C1 PIAOLBVUVDXHHL-UHFFFAOYSA-N 0.000 description 1
- YESNBFAEPGJCQQ-UHFFFAOYSA-N 2-phenylbicyclo[2.2.1]heptan-3-amine Chemical compound NC1C(C2)CCC2C1C1=CC=CC=C1 YESNBFAEPGJCQQ-UHFFFAOYSA-N 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 208000003098 Ganglion Cysts Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 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 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- ASCLNDIFPOOYAH-UHFFFAOYSA-N N,N-diethyl-3-phenylbicyclo[2.2.1]heptan-2-amine Chemical compound C1(=CC=CC=C1)C1C2CCC(C1N(CC)CC)C2 ASCLNDIFPOOYAH-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-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
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000005400 Synovial Cyst Diseases 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
- 239000003929 acidic solution Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- JEPPYVOSGKWVSJ-UHFFFAOYSA-N bicyclo[2.2.1]heptan-3-amine Chemical class C1CC2C(N)CC1C2 JEPPYVOSGKWVSJ-UHFFFAOYSA-N 0.000 description 1
- WGHKYNDIOQMIQQ-UHFFFAOYSA-N bicyclo[2.2.1]heptan-4-amine;hydrochloride Chemical compound Cl.C1CC2CCC1(N)C2 WGHKYNDIOQMIQQ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- CTVMYAZECFXZLN-UHFFFAOYSA-N camfetamine Chemical compound CNC1C(C2)CCC2C1C1=CC=CC=C1 CTVMYAZECFXZLN-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- IKFBPFGUINLYQI-UHFFFAOYSA-N fencamfamin Chemical compound CCNC1C(C2)CCC2C1C1=CC=CC=C1 IKFBPFGUINLYQI-UHFFFAOYSA-N 0.000 description 1
- 235000015244 frankfurter Nutrition 0.000 description 1
- KGZLFTWMCMEEJR-UHFFFAOYSA-N heptane;hydrochloride Chemical compound Cl.CCCCCCC KGZLFTWMCMEEJR-UHFFFAOYSA-N 0.000 description 1
- WEUMBMDSCRAELE-UHFFFAOYSA-N heptane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCC WEUMBMDSCRAELE-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 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
- 238000004519 manufacturing process Methods 0.000 description 1
- LRPCLTPZMUIPFK-UHFFFAOYSA-N methane;sulfuric acid Chemical compound C.OS(O)(=O)=O LRPCLTPZMUIPFK-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 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
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- PIAOLBVUVDXHHL-VOTSOKGWSA-N β-nitrostyrene Chemical compound [O-][N+](=O)\C=C\C1=CC=CC=C1 PIAOLBVUVDXHHL-VOTSOKGWSA-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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
-
- 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
- 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM42332A DE1110159B (de) | 1959-08-01 | 1959-08-01 | Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminonorcamphanderivate bzw. von deren Saeureadditionssalzen und quaternaeren Ammoniumverbindungen |
| CH779260A CH385196A (de) | 1959-08-01 | 1960-07-08 | Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminonorcamphanderivate |
| BE593463A BE593463A (fr) | 1959-08-01 | 1960-07-27 | Procédé de préparation de dérivés N-substitués d'amino-norcamphane à activité analeptique. |
| GB2631360A GB913866A (en) | 1959-08-01 | 1960-07-28 | Improvements in or relating to amino-norcamphane compounds |
| SE743760A SE302957B (enrdf_load_stackoverflow) | 1959-08-01 | 1960-08-01 | |
| DEM46811A DE1201338B (de) | 1959-08-01 | 1960-10-13 | Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminobicyclo-heptanderivate bzw. von deren Saeureadditions-salzen und quaternaeren Ammonium-verbindungen |
| FR834659A FR978M (enrdf_load_stackoverflow) | 1959-08-01 | 1960-10-24 | |
| CH942461A CH419105A (de) | 1959-08-01 | 1961-08-11 | Verfahren zur Herstellung analeptisch wirksamer N-substituierter Amino-norcamphanderivate bzw. von deren Säureadditionssalzen und quaternären Ammoniumverbindungen |
| FR873190A FR25F (fr) | 1959-08-01 | 1961-09-14 | Dérivés d'amino norcamphane n-substitués a action analeptique. |
| GB35384/61A GB968714A (en) | 1959-08-01 | 1961-09-29 | Analeptically active n-substituted amino-norcamphane derivatives and their addition salts with acids and their quaternary ammonium compounds |
| US143578A US3164601A (en) | 1959-08-01 | 1961-10-09 | Analeptically active n-substituted aminonorcamphane derivatives and their acid addition salts and quaternary ammonium compounds |
| BE609074A BE609074R (fr) | 1959-08-01 | 1961-10-12 | Procédé de préparation de dérivés N-substitués d'amino-norcamphane à activité analeptique |
| SE10126/61A SE310175B (enrdf_load_stackoverflow) | 1959-08-01 | 1961-10-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM42332A DE1110159B (de) | 1959-08-01 | 1959-08-01 | Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminonorcamphanderivate bzw. von deren Saeureadditionssalzen und quaternaeren Ammoniumverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1110159B true DE1110159B (de) | 1961-07-06 |
Family
ID=7304304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM42332A Pending DE1110159B (de) | 1959-08-01 | 1959-08-01 | Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminonorcamphanderivate bzw. von deren Saeureadditionssalzen und quaternaeren Ammoniumverbindungen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE593463A (enrdf_load_stackoverflow) |
| CH (1) | CH385196A (enrdf_load_stackoverflow) |
| DE (1) | DE1110159B (enrdf_load_stackoverflow) |
| FR (1) | FR978M (enrdf_load_stackoverflow) |
| GB (1) | GB913866A (enrdf_load_stackoverflow) |
| SE (1) | SE302957B (enrdf_load_stackoverflow) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3164601A (en) * | 1959-08-01 | 1965-01-05 | Merck Ag E | Analeptically active n-substituted aminonorcamphane derivatives and their acid addition salts and quaternary ammonium compounds |
| DE1219478B (de) | 1960-12-23 | 1966-06-23 | Merck Ag E | Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminonorcamphanderivate bzw. von deren Saeureadditionssalzen und quartaeren Ammoniumverbindungen |
| US3308160A (en) * | 1963-06-26 | 1967-03-07 | Du Pont | 4-phenylbicyclo[2.2.2]octane-1-amines and salts thereof |
| US3341402A (en) * | 1965-01-15 | 1967-09-12 | Smith Kline French Lab | Anti-viral composition and method |
| US3362878A (en) * | 1966-08-01 | 1968-01-09 | Du Pont | Pharmaceutical compositions and methods utilizing substituted bicyclo[2.2.2]-octanes |
| DE2003744A1 (de) * | 1969-02-06 | 1970-09-03 | Colgate Palmolive Co | In 3- und 4-Stellung disubstituierte 3-Amino-2-bicyclo[2,2,2]zu-octan-2-ole und Verfahren zu deren Herstellung |
| DE19835766C2 (de) * | 1998-08-07 | 2003-07-03 | Bosch Gmbh Robert | Anordnung zum Beschalten eines elektrochemischen Sensors |
| RU2307826C1 (ru) * | 2006-05-30 | 2007-10-10 | Государственное образовательное учреждение высшего профессионального образования Волгоградский государственный технический университет (ВолгГТУ) | Способ получения n-(3-фенил-2-норкамфанил)-n-этиламина гидрохлорида |
| US11840495B2 (en) | 2020-12-23 | 2023-12-12 | The Broad Institute, Inc. | Compositions and methods related to di-substituted bicyclo[2.2.1] heptanamine-containing compounds |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1284421B (de) * | 1962-06-09 | 1968-12-05 | Knoll Ag | Bicyclisch substituierte Aminoalkane und Verfahren zu ihrer Herstellung |
| DE1298527B (de) * | 1962-06-09 | 1969-07-03 | Knoll Ag | Verfahren zur Herstellung bicyclisch substituierter Aminoalkane |
| WO2017048720A1 (en) | 2015-09-15 | 2017-03-23 | Praxis Biosciences, Llc | Prodrugs of fencamfamine |
-
1959
- 1959-08-01 DE DEM42332A patent/DE1110159B/de active Pending
-
1960
- 1960-07-08 CH CH779260A patent/CH385196A/de unknown
- 1960-07-27 BE BE593463A patent/BE593463A/fr unknown
- 1960-07-28 GB GB2631360A patent/GB913866A/en not_active Expired
- 1960-08-01 SE SE743760A patent/SE302957B/xx unknown
- 1960-10-24 FR FR834659A patent/FR978M/fr not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3164601A (en) * | 1959-08-01 | 1965-01-05 | Merck Ag E | Analeptically active n-substituted aminonorcamphane derivatives and their acid addition salts and quaternary ammonium compounds |
| DE1201338B (de) | 1959-08-01 | 1965-09-23 | Merck Ag E | Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminobicyclo-heptanderivate bzw. von deren Saeureadditions-salzen und quaternaeren Ammonium-verbindungen |
| DE1219478B (de) | 1960-12-23 | 1966-06-23 | Merck Ag E | Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminonorcamphanderivate bzw. von deren Saeureadditionssalzen und quartaeren Ammoniumverbindungen |
| US3308160A (en) * | 1963-06-26 | 1967-03-07 | Du Pont | 4-phenylbicyclo[2.2.2]octane-1-amines and salts thereof |
| US3341402A (en) * | 1965-01-15 | 1967-09-12 | Smith Kline French Lab | Anti-viral composition and method |
| US3362878A (en) * | 1966-08-01 | 1968-01-09 | Du Pont | Pharmaceutical compositions and methods utilizing substituted bicyclo[2.2.2]-octanes |
| DE2003744A1 (de) * | 1969-02-06 | 1970-09-03 | Colgate Palmolive Co | In 3- und 4-Stellung disubstituierte 3-Amino-2-bicyclo[2,2,2]zu-octan-2-ole und Verfahren zu deren Herstellung |
| DE19835766C2 (de) * | 1998-08-07 | 2003-07-03 | Bosch Gmbh Robert | Anordnung zum Beschalten eines elektrochemischen Sensors |
| RU2307826C1 (ru) * | 2006-05-30 | 2007-10-10 | Государственное образовательное учреждение высшего профессионального образования Волгоградский государственный технический университет (ВолгГТУ) | Способ получения n-(3-фенил-2-норкамфанил)-n-этиламина гидрохлорида |
| US11840495B2 (en) | 2020-12-23 | 2023-12-12 | The Broad Institute, Inc. | Compositions and methods related to di-substituted bicyclo[2.2.1] heptanamine-containing compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| GB913866A (en) | 1962-12-28 |
| BE593463A (fr) | 1961-01-27 |
| SE302957B (enrdf_load_stackoverflow) | 1968-08-12 |
| FR978M (enrdf_load_stackoverflow) | 1961-12-04 |
| CH385196A (de) | 1964-12-15 |
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