FI56522C - Nytt foerfarande foer framstaellning av n-(trans-4-hydroksy-syklohexyl)-(2-amino-3,5-dibrom-benzyl)-amin - Google Patents
Nytt foerfarande foer framstaellning av n-(trans-4-hydroksy-syklohexyl)-(2-amino-3,5-dibrom-benzyl)-amin Download PDFInfo
- Publication number
- FI56522C FI56522C FI123273A FI123273A FI56522C FI 56522 C FI56522 C FI 56522C FI 123273 A FI123273 A FI 123273A FI 123273 A FI123273 A FI 123273A FI 56522 C FI56522 C FI 56522C
- Authority
- FI
- Finland
- Prior art keywords
- amino
- trans
- dibromo
- cyclohexyl
- hydroxy
- Prior art date
Links
- JBDGDEWWOUBZPM-UHFFFAOYSA-N 4-[(2-amino-3,5-dibromophenyl)methylamino]-1-cyclohexanol Chemical compound NC1=C(Br)C=C(Br)C=C1CNC1CCC(O)CC1 JBDGDEWWOUBZPM-UHFFFAOYSA-N 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- -1 N- (2-Amino-3,5-diboryl-benzylidene) -trans-4-amino-cyclohexanol Chemical compound 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 2
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NAIJZCXBMHHHDM-UHFFFAOYSA-N 2-(aminomethyl)-4,6-dibromoaniline Chemical compound NCC1=CC(Br)=CC(Br)=C1N NAIJZCXBMHHHDM-UHFFFAOYSA-N 0.000 description 1
- RCPAZWISSAVDEA-UHFFFAOYSA-N 2-amino-3,5-dibromobenzaldehyde Chemical compound NC1=C(Br)C=C(Br)C=C1C=O RCPAZWISSAVDEA-UHFFFAOYSA-N 0.000 description 1
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical compound NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 description 1
- QHFGYJWGASPRHW-UHFFFAOYSA-N 4-amino-3,5-dibromobenzaldehyde Chemical compound NC1=C(Br)C=C(C=O)C=C1Br QHFGYJWGASPRHW-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 group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- QNVKOSLOVOTXKF-PFWPSKEQSA-N chembl1514634 Chemical compound Cl.NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 QNVKOSLOVOTXKF-PFWPSKEQSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- VVNXEADCOVSAER-UHFFFAOYSA-N lithium sodium Chemical compound [Li].[Na] VVNXEADCOVSAER-UHFFFAOYSA-N 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
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GUQRKZPMVLRXLT-UHFFFAOYSA-N n-cyclohexylhydroxylamine Chemical class ONC1CCCCC1 GUQRKZPMVLRXLT-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 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
- 238000010992 reflux Methods 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
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2218647 | 1972-04-18 | ||
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| FI56522B FI56522B (fi) | 1979-10-31 |
| FI56522C true FI56522C (fi) | 1980-02-11 |
Family
ID=5842287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI123273A FI56522C (fi) | 1972-04-18 | 1973-04-17 | Nytt foerfarande foer framstaellning av n-(trans-4-hydroksy-syklohexyl)-(2-amino-3,5-dibrom-benzyl)-amin |
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 |
| SE415970B (sv) | 1980-11-17 |
| DE2218647A1 (de) | 1973-10-25 |
| FI56522B (fi) | 1979-10-31 |
| PL86344B1 (en, 2012) | 1976-05-31 |
| 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 |
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