DE1493715A1 - Verfahren zur Herstellung von Diphenylpropylaminderivaten - Google Patents
Verfahren zur Herstellung von DiphenylpropylaminderivatenInfo
- Publication number
- DE1493715A1 DE1493715A1 DE19651493715 DE1493715A DE1493715A1 DE 1493715 A1 DE1493715 A1 DE 1493715A1 DE 19651493715 DE19651493715 DE 19651493715 DE 1493715 A DE1493715 A DE 1493715A DE 1493715 A1 DE1493715 A1 DE 1493715A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- compounds
- above meanings
- group
- benzyl
- 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
- 238000000034 method Methods 0.000 title claims description 20
- 230000008569 process Effects 0.000 title claims description 11
- KISZTEOELCMZPY-UHFFFAOYSA-N 3,3-diphenylpropylamine Chemical class C=1C=CC=CC=1C(CCN)C1=CC=CC=C1 KISZTEOELCMZPY-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- 229940051806 diphenylpropylamine derivative analgesics Drugs 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- HMMWEJUBAXMERM-UHFFFAOYSA-N 2,2-diphenylpropanal Chemical class C=1C=CC=CC=1C(C=O)(C)C1=CC=CC=C1 HMMWEJUBAXMERM-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000007514 bases Chemical class 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- -1 Diphenylpropylami n -d Chemical compound 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 230000009467 reduction Effects 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000002994 raw material 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
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- MXLSBQCNYIHJEL-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-1-hydroxypropan-2-one Chemical compound CC=1C=C(C=CC1C)C(C(C)=O)O MXLSBQCNYIHJEL-UHFFFAOYSA-N 0.000 description 1
- CBALKMGGDUMBIJ-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C(C)=C1 CBALKMGGDUMBIJ-UHFFFAOYSA-N 0.000 description 1
- HCYKFLKYGHKHGV-UHFFFAOYSA-N 2-(3,4-diethylphenyl)oxirane Chemical compound C(C)C=1C=C(C=CC1CC)C1CO1 HCYKFLKYGHKHGV-UHFFFAOYSA-N 0.000 description 1
- NATLVNNKDPMRAG-UHFFFAOYSA-N 2-(3,4-dimethylphenyl)-2-oxoacetaldehyde Chemical compound CC1=CC=C(C(=O)C=O)C=C1C NATLVNNKDPMRAG-UHFFFAOYSA-N 0.000 description 1
- GMFDVHPDGHUBBS-UHFFFAOYSA-N 2-(3,4-dimethylphenyl)oxirane Chemical compound C1=C(C)C(C)=CC=C1C1OC1 GMFDVHPDGHUBBS-UHFFFAOYSA-N 0.000 description 1
- LFOAGCXZPJZHOY-UHFFFAOYSA-N 2-amino-1-(3,4-dimethylphenyl)ethanol Chemical compound CC1=CC=C(C(O)CN)C=C1C LFOAGCXZPJZHOY-UHFFFAOYSA-N 0.000 description 1
- LYIIBVSRGJSHAV-UHFFFAOYSA-N 2-aminoacetaldehyde Chemical class NCC=O LYIIBVSRGJSHAV-UHFFFAOYSA-N 0.000 description 1
- DFSBSZYRJJTTDU-UHFFFAOYSA-N 2-chloro-1-(3,4-dimethylphenyl)ethanone Chemical compound CC1=CC=C(C(=O)CCl)C=C1C DFSBSZYRJJTTDU-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- IVVVCTZKFHPUMJ-UHFFFAOYSA-N 3-(3-methoxyphenyl)-3-(4-methoxyphenyl)propan-1-amine Chemical compound C1=CC(OC)=CC=C1C(CCN)C1=CC=CC(OC)=C1 IVVVCTZKFHPUMJ-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
- BMCQVJPMBSZWNA-UHFFFAOYSA-N 4-(3-amino-1-phenylpropyl)phenol Chemical compound C=1C=C(O)C=CC=1C(CCN)C1=CC=CC=C1 BMCQVJPMBSZWNA-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 229910000761 Aluminium amalgam Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- AXCXURFBTQDQEL-UHFFFAOYSA-N C(C)C=1C=C(C=CC1CC)C(C(C)=O)O Chemical compound C(C)C=1C=C(C=CC1CC)C(C(C)=O)O AXCXURFBTQDQEL-UHFFFAOYSA-N 0.000 description 1
- 206010011416 Croup infectious Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 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
- 244000309464 bull Species 0.000 description 1
- 230000002308 calcification Effects 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 201000010549 croup Diseases 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- ADWDNOJZWIDEOT-UHFFFAOYSA-N n-phenylaniline;hydrobromide Chemical compound [Br-].C=1C=CC=CC=1[NH2+]C1=CC=CC=C1 ADWDNOJZWIDEOT-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940045681 other alkylating agent in atc Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005406 washing Methods 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
- C07D213/38—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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0046262 | 1965-06-05 | ||
| DEF0047601 | 1965-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1493715A1 true DE1493715A1 (de) | 1969-06-19 |
Family
ID=25976808
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651493715 Pending DE1493715A1 (de) | 1965-06-05 | 1965-06-05 | Verfahren zur Herstellung von Diphenylpropylaminderivaten |
| DE19651545869 Pending DE1545869A1 (de) | 1965-06-05 | 1965-11-05 | Verfahren zur Herstellung von 3-Phenyl-3-pyridyl(2')-propylamin-derivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651545869 Pending DE1545869A1 (de) | 1965-06-05 | 1965-11-05 | Verfahren zur Herstellung von 3-Phenyl-3-pyridyl(2')-propylamin-derivaten |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3414578A (en:Method) |
| AT (8) | AT277980B (en:Method) |
| BE (1) | BE682140A (en:Method) |
| BR (1) | BR6680181D0 (en:Method) |
| CH (4) | CH464962A (en:Method) |
| DE (2) | DE1493715A1 (en:Method) |
| DK (1) | DK118407B (en:Method) |
| ES (1) | ES327479A1 (en:Method) |
| FI (1) | FI45184C (en:Method) |
| GB (1) | GB1124838A (en:Method) |
| IL (1) | IL25875A (en:Method) |
| NL (1) | NL6607736A (en:Method) |
| NO (1) | NO117860B (en:Method) |
| SE (1) | SE348457B (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4275198A (en) * | 1980-07-18 | 1981-06-23 | Carter-Wallace Inc. | Method for preparing basic dithienyl compounds |
-
1965
- 1965-06-05 DE DE19651493715 patent/DE1493715A1/de active Pending
- 1965-11-05 DE DE19651545869 patent/DE1545869A1/de active Pending
-
1966
- 1966-05-30 IL IL25875A patent/IL25875A/xx unknown
- 1966-06-02 CH CH1468468A patent/CH464962A/de unknown
- 1966-06-02 CH CH1468068A patent/CH464960A/de unknown
- 1966-06-02 CH CH797366A patent/CH465645A/de unknown
- 1966-06-02 SE SE07542/66A patent/SE348457B/xx unknown
- 1966-06-02 CH CH1468168A patent/CH464961A/de unknown
- 1966-06-02 FI FI661451A patent/FI45184C/fi active
- 1966-06-02 ES ES0327479A patent/ES327479A1/es not_active Expired
- 1966-06-03 AT AT01690/68A patent/AT277980B/de active
- 1966-06-03 NL NL6607736A patent/NL6607736A/xx unknown
- 1966-06-03 AT AT169168A patent/AT275500B/de active
- 1966-06-03 AT AT529166A patent/AT272310B/de active
- 1966-06-03 AT AT168968A patent/AT272312B/de active
- 1966-06-03 DK DK288666AA patent/DK118407B/da unknown
- 1966-06-03 AT AT169368A patent/AT275501B/de active
- 1966-06-03 AT AT169268A patent/AT272313B/de active
- 1966-06-03 AT AT169468A patent/AT272314B/de active
- 1966-06-03 AT AT168868A patent/AT272311B/de active
- 1966-06-03 BR BR180181/66A patent/BR6680181D0/pt unknown
- 1966-06-04 NO NO163304A patent/NO117860B/no unknown
- 1966-06-06 GB GB25044/66A patent/GB1124838A/en not_active Expired
- 1966-06-06 BE BE682140D patent/BE682140A/xx unknown
- 1966-10-27 US US589816A patent/US3414578A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FI45184C (fi) | 1972-04-10 |
| CH465645A (de) | 1968-11-30 |
| NO117860B (en:Method) | 1969-10-06 |
| BR6680181D0 (pt) | 1973-12-26 |
| AT272313B (de) | 1969-07-10 |
| ES327479A1 (es) | 1967-10-16 |
| CH464962A (de) | 1968-11-15 |
| US3414578A (en) | 1968-12-03 |
| AT275501B (de) | 1969-10-27 |
| CH464961A (de) | 1968-11-15 |
| AT272311B (de) | 1969-07-10 |
| DK118407B (da) | 1970-08-17 |
| BE682140A (en:Method) | 1966-12-06 |
| IL25875A (en) | 1970-04-20 |
| SE348457B (en:Method) | 1972-09-04 |
| AT272312B (de) | 1969-07-10 |
| CH464960A (de) | 1968-11-15 |
| NL6607736A (en:Method) | 1966-12-06 |
| DE1545869A1 (de) | 1969-12-04 |
| AT275500B (de) | 1969-10-27 |
| AT272310B (de) | 1969-07-10 |
| FI45184B (en:Method) | 1971-12-31 |
| GB1124838A (en) | 1968-08-21 |
| AT272314B (de) | 1969-07-10 |
| AT277980B (de) | 1970-01-12 |
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