PL86344B1 - - Google Patents
Download PDFInfo
- Publication number
- PL86344B1 PL86344B1 PL16196373A PL16196373A PL86344B1 PL 86344 B1 PL86344 B1 PL 86344B1 PL 16196373 A PL16196373 A PL 16196373A PL 16196373 A PL16196373 A PL 16196373A PL 86344 B1 PL86344 B1 PL 86344B1
- Authority
- PL
- Poland
- Prior art keywords
- trans
- amino
- acid addition
- reductions
- amine
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- -1 2-amino-3,5-dibromobenzyl Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 2
- 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 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 1
- RKTQEVMZBCBOSB-UHFFFAOYSA-N 4-aminocyclohexan-1-ol;hydron;chloride Chemical compound Cl.NC1CCC(O)CC1 RKTQEVMZBCBOSB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 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
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 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
- 239000003054 catalyst Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722218647 DE2218647A1 (de) | 1972-04-18 | 1972-04-18 | Neues verfahren zur herstellung von n-(trans-4-hydroxy-cyclohexyl)-(2-amino3,5-dibrom-benzyl)-amin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL86344B1 true PL86344B1 (en, 2012) | 1976-05-31 |
Family
ID=5842287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL16196373A PL86344B1 (en, 2012) | 1972-04-18 | 1973-04-17 |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS554096B2 (en, 2012) |
| AT (1) | AT321270B (en, 2012) |
| BG (1) | BG22807A3 (en, 2012) |
| CA (1) | CA1003441A (en, 2012) |
| CH (1) | CH575907A5 (en, 2012) |
| CS (1) | CS174876B2 (en, 2012) |
| DD (1) | DD107261A5 (en, 2012) |
| DE (1) | DE2218647A1 (en, 2012) |
| DK (2) | DK139515C (en, 2012) |
| ES (2) | ES413827A1 (en, 2012) |
| FI (1) | FI56522C (en, 2012) |
| HU (1) | HU165758B (en, 2012) |
| NO (1) | NO137086C (en, 2012) |
| PL (1) | PL86344B1 (en, 2012) |
| RO (1) | RO65104A (en, 2012) |
| SE (2) | SE415970B (en, 2012) |
| SU (1) | SU458976A3 (en, 2012) |
| YU (1) | YU35573B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2223193C3 (de) * | 1972-05-12 | 1975-05-28 | Dr. Karl Thomae Gmbh, 7950 Biberach | Verfahren zur Herstellung von 2-Amino-benzylaminen |
| US4020104A (en) * | 1976-09-20 | 1977-04-26 | The Upjohn Company | Process for isomerizing cis,cis- and cis,trans-isomers of di-(p-aminocyclohexyl)methane to the corresponding trans,trans-isomer |
| DE2720867C2 (de) * | 1977-05-10 | 1979-05-31 | Kernforschungsanlage Juelich Gmbh, 5170 Juelich | Verfahren zur quantitativen Abtrennung von Uran aus Proben natürlichen Wassers |
| ATE22069T1 (de) * | 1983-06-29 | 1986-09-15 | Heumann Ludwig & Co Gmbh | Verfahren zur herstellung von 2-amino-3,5dibrombenzylaminen. |
| IT1216837B (it) * | 1987-01-07 | 1990-03-14 | Erregierre Ind Chim | Sali della n-(trans-p-idrossi-cicloesil)-(2ammino-3,5-dibromo) benzilammina dotati di attivita' mucolitica. |
| HU207834B (en) * | 1989-12-22 | 1993-06-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing n-/2-amino-3,5-dibromo-benzyl/-trans-4-amino-cyclohexanol |
-
1972
- 1972-04-18 DE DE19722218647 patent/DE2218647A1/de active Pending
-
1973
- 1973-03-14 RO RO7416173A patent/RO65104A/ro unknown
- 1973-03-22 DD DD16964973A patent/DD107261A5/xx unknown
- 1973-04-06 AT AT302573A patent/AT321270B/de not_active IP Right Cessation
- 1973-04-13 CH CH537473A patent/CH575907A5/xx not_active IP Right Cessation
- 1973-04-13 CS CS264873A patent/CS174876B2/cs unknown
- 1973-04-16 BG BG023331A patent/BG22807A3/xx unknown
- 1973-04-16 YU YU101773A patent/YU35573B/xx unknown
- 1973-04-16 HU HUTO000903 patent/HU165758B/hu unknown
- 1973-04-16 JP JP4298973A patent/JPS554096B2/ja not_active Expired
- 1973-04-16 SU SU1911298A patent/SU458976A3/ru active
- 1973-04-17 FI FI123273A patent/FI56522C/fi active
- 1973-04-17 ES ES413827A patent/ES413827A1/es not_active Expired
- 1973-04-17 SE SE7305489A patent/SE415970B/sv unknown
- 1973-04-17 DK DK212473A patent/DK139515C/da not_active IP Right Cessation
- 1973-04-17 PL PL16196373A patent/PL86344B1/pl unknown
- 1973-04-17 CA CA168,938A patent/CA1003441A/en not_active Expired
- 1973-04-17 NO NO162073A patent/NO137086C/no unknown
- 1973-12-04 ES ES421120A patent/ES421120A1/es not_active Expired
-
1975
- 1975-12-08 SE SE7513808A patent/SE421613B/xx not_active IP Right Cessation
-
1976
- 1976-12-17 DK DK570776A patent/DK570776A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DK570776A (da) | 1976-12-17 |
| JPS4914443A (en, 2012) | 1974-02-07 |
| BG22807A3 (bg) | 1977-04-20 |
| FI56522C (fi) | 1980-02-11 |
| SE415970B (sv) | 1980-11-17 |
| DE2218647A1 (de) | 1973-10-25 |
| FI56522B (fi) | 1979-10-31 |
| NO137086B (no) | 1977-09-19 |
| AT321270B (de) | 1975-03-25 |
| HU165758B (en, 2012) | 1974-10-28 |
| SE7513808L (sv) | 1975-12-08 |
| ES421120A1 (es) | 1976-06-16 |
| DK139515C (da) | 1979-08-20 |
| CH575907A5 (en, 2012) | 1976-05-31 |
| YU35573B (en) | 1981-04-30 |
| NO137086C (no) | 1977-12-28 |
| SU458976A3 (ru) | 1975-01-30 |
| ES413827A1 (es) | 1976-01-16 |
| CA1003441A (en) | 1977-01-11 |
| DD107261A5 (en, 2012) | 1974-07-20 |
| YU101773A (en) | 1980-10-31 |
| SE421613B (sv) | 1982-01-18 |
| RO65104A (fr) | 1979-08-15 |
| DK139515B (da) | 1979-03-05 |
| JPS554096B2 (en, 2012) | 1980-01-29 |
| CS174876B2 (en, 2012) | 1977-04-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2627491A (en) | Penicillin salts of substituted alkylene diamines | |
| US2916490A (en) | Ocjhs | |
| US2739981A (en) | Diamines and salts thereof | |
| JPS5943459B2 (ja) | Ｎ−アルキルピペリジン誘導体 | |
| US3117128A (en) | Certificate of correction | |
| DE2803582A1 (de) | Neue tetralinderivate, ihre herstellung und verwendung | |
| EP0165422B1 (de) | Neue substituierte Bis(4-aminophenyl)sulfone, ihre Herstellung und ihre Verwendung als Arzneimittel | |
| US2975180A (en) | 4, 7-diamino-2-aryl-6-pteridinecarboxamides | |
| DD242407A5 (de) | Verfahren zur herstellung von imidazoderivaten | |
| CH445512A (de) | Verfahren zur Herstellung von neuen Indolderivaten | |
| US2868833A (en) | Aliphatic diamines and salts thereof | |
| PL86344B1 (en, 2012) | ||
| US2830987A (en) | Derivatives of phenthiazine | |
| DE1807887A1 (de) | 2,7-Diamino-6-arylpyrido [2,3-d] pyrimidinverbindungen und Verfahren zu ihrer Herstellung | |
| CH637373A5 (en) | Process for preparing novel 2-aminotetralins | |
| US3306909A (en) | 3-carbamoyl-1,5-diphenyl-2,4-pyrrolidinediones | |
| US3813407A (en) | Process for the preparation of 1-hydroxy-2-(1,1-difluoroalkyl)benzimidazoles and 1-hydroxy-2-(1,1-difluoroalkyl)-1h-imidazo(4,5-b)pyridines | |
| US3306903A (en) | 1-aminopyridyl-4-(phenyl or pyridyl)-piperazines and intermediates | |
| SU552896A3 (ru) | Способ получени -арилсульфонил- "(3-азабициклоалкил)мочевин или их солей | |
| CA1112648A (en) | 2-[3,4-disubstituted-phenylimino]-imidazolidines | |
| US3337539A (en) | Tetraethoxy-1, 2, 3, 4-tetrahydroisoquinoline derivatives and salts thereof | |
| US3272816A (en) | 7-amino-2, 4-dioxo-1, 2, 3, 4-tetrahydropyrido[2, 3-d]pyrimidines | |
| PL97091B1 (pl) | Sposob wytwarzania nowych podstawionych n-/2-pirolidynyloalkilo/benzamidow | |
| US2554186A (en) | Para-amino hydroxybenzamides | |
| Taylor Jr | Pteridines. VIII. The Synthesis of 2, 4-Bis-(alkylamino)-6, 7-diphenylpteridines |