CH479552A - Procédé pour la préparation de cétimines - Google Patents
Procédé pour la préparation de cétiminesInfo
- Publication number
- CH479552A CH479552A CH421068A CH421068A CH479552A CH 479552 A CH479552 A CH 479552A CH 421068 A CH421068 A CH 421068A CH 421068 A CH421068 A CH 421068A CH 479552 A CH479552 A CH 479552A
- Authority
- CH
- Switzerland
- Prior art keywords
- radical
- alkyl
- phenyl
- amino
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 34
- 238000002360 preparation method Methods 0.000 title claims description 10
- 150000004658 ketimines Chemical class 0.000 title claims description 8
- -1 cycloalkyl radical Chemical class 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 16
- 150000002466 imines Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 3
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001342 alkaline earth metals 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
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 150000002168 ethanoic acid esters Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- QNIUWWCDBYUWGZ-UHFFFAOYSA-N 2-(benzenecarboximidoyl)-4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1C(=N)C1=CC=CC=C1 QNIUWWCDBYUWGZ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 5
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YIBUYDHSWMGPBG-UHFFFAOYSA-N 2-(benzenecarboximidoyl)-4-chloro-n-methylaniline Chemical compound CNC1=CC=C(Cl)C=C1C(=N)C1=CC=CC=C1 YIBUYDHSWMGPBG-UHFFFAOYSA-N 0.000 description 3
- OWVWEVNXXMKHJO-UHFFFAOYSA-N 2-(benzenecarboximidoyl)-4-methylaniline Chemical compound CC1=CC=C(N)C(C(=N)C=2C=CC=CC=2)=C1 OWVWEVNXXMKHJO-UHFFFAOYSA-N 0.000 description 3
- QYRDWARBHMCOAG-UHFFFAOYSA-N 2-amino-5-chlorobenzonitrile Chemical compound NC1=CC=C(Cl)C=C1C#N QYRDWARBHMCOAG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001557 benzodiazepines Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- DLGOLDCIEHQIMN-UHFFFAOYSA-N 2-(benzenecarboximidoyl)aniline Chemical compound NC1=CC=CC=C1C(=N)C1=CC=CC=C1 DLGOLDCIEHQIMN-UHFFFAOYSA-N 0.000 description 2
- PJBFHGHMMOGYNF-UHFFFAOYSA-N 2-amino-3-ethoxy-3-oxopropanoic acid;hydrochloride Chemical compound Cl.CCOC(=O)C(N)C(O)=O PJBFHGHMMOGYNF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 2
- 230000009920 chelation Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 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
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
- OZLMBXPYRDASTP-UHFFFAOYSA-N 2-amino-5-methylbenzonitrile Chemical compound CC1=CC=C(N)C(C#N)=C1 OZLMBXPYRDASTP-UHFFFAOYSA-N 0.000 description 1
- VQXZNIHTQSKYQH-UHFFFAOYSA-N 3-o-amino 1-o-ethyl propanedioate Chemical compound CCOC(=O)CC(=O)ON VQXZNIHTQSKYQH-UHFFFAOYSA-N 0.000 description 1
- BJGINSGODPCLGI-UHFFFAOYSA-N 3-o-amino 1-o-methyl propanedioate Chemical compound COC(=O)CC(=O)ON BJGINSGODPCLGI-UHFFFAOYSA-N 0.000 description 1
- JPLVBKVYAXTTCU-UHFFFAOYSA-N 4-chloro-2-pentanimidoylaniline Chemical compound CCCCC(=N)C1=CC(Cl)=CC=C1N JPLVBKVYAXTTCU-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100231508 Caenorhabditis elegans ceh-5 gene Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- WLTCKEHCTUYJGI-UHFFFAOYSA-N Diethyl aminomalonate Chemical compound CCOC(=O)C(N)C(=O)OCC WLTCKEHCTUYJGI-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- JINBYESILADKFW-UHFFFAOYSA-N aminomalonic acid Chemical compound OC(=O)C(N)C(O)=O JINBYESILADKFW-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000004792 aryl magnesium halides Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 1
- 229940052299 calcium chloride dihydrate Drugs 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- RFRXWABRBNUAHS-UHFFFAOYSA-N ethyl 2-(methylideneamino)acetate Chemical compound CCOC(=O)CN=C RFRXWABRBNUAHS-UHFFFAOYSA-N 0.000 description 1
- NFOQQJRPUGIFHN-UHFFFAOYSA-N ethyl 2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepine-3-carboxylate Chemical compound C12=CC=CC=C2NC(=O)C(C(=O)OCC)N=C1C1=CC=CC=C1 NFOQQJRPUGIFHN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000000879 imine group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 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
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940035677 psycholeptics Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
- Perforating, Stamping-Out Or Severing By Means Other Than Cutting (AREA)
- Devices For Post-Treatments, Processing, Supply, Discharge, And Other Processes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR978360A FR1497456A (fr) | 1964-06-15 | 1964-06-15 | Ortho-amino aryl cétimines, composés hétérocycliques qui s'y rattachent et prépaation de ces divers corps |
| FR12886A FR91403E (fr) | 1964-06-15 | 1965-04-12 | Ortho-amino aryl cétimines, composés hétérocycliques qui s'y rattachent et préparation de ces divers corps |
| CH830765A CH485741A (fr) | 1964-06-15 | 1965-06-15 | Procédé de préparation de dérivés de benzodiazépines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH479552A true CH479552A (fr) | 1969-10-15 |
Family
ID=26163072
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH421068A CH479552A (fr) | 1964-06-15 | 1965-06-15 | Procédé pour la préparation de cétimines |
| CH830765A CH485741A (fr) | 1964-06-15 | 1965-06-15 | Procédé de préparation de dérivés de benzodiazépines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH830765A CH485741A (fr) | 1964-06-15 | 1965-06-15 | Procédé de préparation de dérivés de benzodiazépines |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3516988A (en, 2012) |
| AT (2) | AT284084B (en, 2012) |
| BE (1) | BE665401A (en, 2012) |
| BR (1) | BR6570433D0 (en, 2012) |
| CA (2) | CA958708A (en, 2012) |
| CH (2) | CH479552A (en, 2012) |
| DE (2) | DE1795832C3 (en, 2012) |
| DK (3) | DK138493B (en, 2012) |
| FI (2) | FI47986C (en, 2012) |
| FR (3) | FR1497456A (en, 2012) |
| GB (3) | GB1117061A (en, 2012) |
| IL (2) | IL23712A (en, 2012) |
| MY (3) | MY7100179A (en, 2012) |
| NL (2) | NL155545B (en, 2012) |
| NO (1) | NO120115B (en, 2012) |
| SE (2) | SE386891B (en, 2012) |
| YU (3) | YU100565A (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2008612A1 (de) * | 1969-03-13 | 1970-10-01 | F. Hoffmann-La Roche & Co Ag, Basel (Schweiz) | Benzodiazepin-Derivate |
| FR2012061A1 (en) * | 1969-06-30 | 1970-03-13 | Sandoz Sa | Quinazolinone derivs - with antiphlogistic props |
| GB1538164A (en) * | 1976-05-05 | 1979-01-10 | Clin Midy | Benzodiazepine derivatives |
| FR2470116A1 (fr) * | 1979-11-27 | 1981-05-29 | Synthelabo | Derives benzylideniques, leur preparation et leur application en therapeutique |
| JPS6019753A (ja) * | 1983-07-13 | 1985-01-31 | Shionogi & Co Ltd | オルト−（モノ置換アミノ）フエニルイミン類およびその製造法 |
| JPS6038380A (ja) * | 1983-08-11 | 1985-02-27 | Shionogi & Co Ltd | １−ピペリジニル−１，４−ベンゾジアゼピン類の改良合成法 |
| US6277844B1 (en) | 1998-09-14 | 2001-08-21 | Sydney Spector | Compound for selective treatment of malignant cells by inhibiting cell cycle progression, decreasing Bcl2, and increasing apoptosis |
| EP1398033B1 (en) * | 1999-04-30 | 2009-06-17 | The Regents Of The University Of Michigan | Use of benzodiazepines for treating autoimmune diseases, inflammations, neoplasies, viral infections and atherosclerosis |
| WO2002098865A2 (fr) * | 2001-06-07 | 2002-12-12 | Neuro3D | Inhibiteurs des phosphodiesterases des nucleotides cycliques, preparation et utilisations de ces inhibiteurs |
| WO2017214442A1 (en) | 2016-06-08 | 2017-12-14 | President And Fellows Of Harvard College | Methods and compositions for reducing tactile dysfunction and anxiety associated with autism spectrum disorder, rett syndrome, and fragile x syndrome |
| WO2019226808A1 (en) | 2018-05-22 | 2019-11-28 | President And Fellows Of Harvard College | Compositions and methods for reducing tactile dysfunction, anxiety, and social impairment |
| EP3801512A4 (en) | 2018-05-29 | 2022-01-19 | President and Fellows of Harvard College | COMPOSITIONS AND METHODS FOR REDUCING TOUCH DYSFUNCTION, ANXIETY AND SOCIAL DISABILITY |
| WO2020198275A1 (en) | 2019-03-25 | 2020-10-01 | President And Fellows Of Harvard College | Compositions and methods for reducing tactile dysfunction, anxiety, and social impairment |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3410844A (en) * | 1966-03-14 | 1968-11-12 | American Home Prod | 2, 3, 4, 5-tetrahydro-2-oxo-1h-1, 4-benzodiazepine-3-carboxylic acid, esters and related compounds |
-
1964
- 1964-06-15 FR FR978360A patent/FR1497456A/fr not_active Expired
- 1964-09-14 FR FR988058A patent/FR4206M/fr not_active Expired
-
1965
- 1965-04-12 FR FR12886A patent/FR91403E/fr not_active Expired
- 1965-06-11 IL IL23712A patent/IL23712A/xx unknown
- 1965-06-11 IL IL32140A patent/IL32140A/xx unknown
- 1965-06-14 GB GB25133/65A patent/GB1117061A/en not_active Expired
- 1965-06-14 FI FI651408A patent/FI47986C/fi active
- 1965-06-14 BE BE665401A patent/BE665401A/xx unknown
- 1965-06-14 SE SE7003514*3A patent/SE386891B/xx unknown
- 1965-06-14 DE DE1795832A patent/DE1795832C3/de not_active Expired
- 1965-06-14 SE SE07800/65A patent/SE336341B/xx unknown
- 1965-06-14 DE DE1518764A patent/DE1518764C3/de not_active Expired
- 1965-06-14 GB GB51366/67A patent/GB1117063A/en not_active Expired
- 1965-06-14 GB GB42698/67A patent/GB1117062A/en not_active Expired
- 1965-06-15 YU YU01005/65A patent/YU100565A/xx unknown
- 1965-06-15 AT AT08973/67A patent/AT284084B/de active
- 1965-06-15 CH CH421068A patent/CH479552A/fr not_active IP Right Cessation
- 1965-06-15 NL NL6507637.A patent/NL155545B/xx not_active IP Right Cessation
- 1965-06-15 DK DK300165AA patent/DK138493B/da unknown
- 1965-06-15 CH CH830765A patent/CH485741A/fr not_active IP Right Cessation
- 1965-06-15 YU YU100/65A patent/YU32996B/xx unknown
- 1965-06-15 AT AT543065A patent/AT268285B/de active
- 1965-06-15 BR BR170433/65A patent/BR6570433D0/pt unknown
- 1965-06-15 NO NO158505A patent/NO120115B/no unknown
-
1968
- 1968-02-19 US US706713A patent/US3516988A/en not_active Expired - Lifetime
- 1968-02-27 YU YU454/68A patent/YU35570B/xx unknown
-
1969
- 1969-09-16 FI FI692643A patent/FI51586C/fi active
-
1970
- 1970-01-22 DK DK29870AA patent/DK125856B/da unknown
-
1971
- 1971-05-10 DK DK223471AA patent/DK129126B/da unknown
- 1971-12-31 MY MY1971179A patent/MY7100179A/xx unknown
- 1971-12-31 MY MY1971181A patent/MY7100181A/xx unknown
- 1971-12-31 MY MY1971180A patent/MY7100180A/xx unknown
-
1972
- 1972-09-18 CA CA958708A patent/CA958708A/en not_active Expired
- 1972-09-18 CA CA958707A patent/CA958707A/en not_active Expired
-
1975
- 1975-01-13 NL NL7500364.A patent/NL155828B/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: SANOFI S.A. |
|
| PL | Patent ceased |