FI62531C - Foerfarande foer framstaellning av terapeutiskt anvaendbart 3-yan-n-(n n-dimetylamino-propyl)-iminodibensyl och syraadd itonssalter daerav - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbart 3-yan-n-(n n-dimetylamino-propyl)-iminodibensyl och syraadd itonssalter daerav Download PDFInfo
- Publication number
- FI62531C FI62531C FI772675A FI772675A FI62531C FI 62531 C FI62531 C FI 62531C FI 772675 A FI772675 A FI 772675A FI 772675 A FI772675 A FI 772675A FI 62531 C FI62531 C FI 62531C
- Authority
- FI
- Finland
- Prior art keywords
- compound
- formula
- acid
- iminodibenzyl
- dimethylaminopropyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 10
- 230000001225 therapeutic effect Effects 0.000 title description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
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- 239000000243 solution Substances 0.000 description 33
- -1 N, N-dimethylamino-propyl Chemical group 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 210000004129 prosencephalon Anatomy 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 210000003568 synaptosome Anatomy 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D223/28—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a single bond between positions 10 and 11
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1287676 | 1976-10-12 | ||
| CH1287676A CH623574A5 (en, 2012) | 1976-10-12 | 1976-10-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI772675A7 FI772675A7 (fi) | 1978-04-13 |
| FI62531B FI62531B (fi) | 1982-09-30 |
| FI62531C true FI62531C (fi) | 1983-01-10 |
Family
ID=4387222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI772675A FI62531C (fi) | 1976-10-12 | 1977-09-09 | Foerfarande foer framstaellning av terapeutiskt anvaendbart 3-yan-n-(n n-dimetylamino-propyl)-iminodibensyl och syraadd itonssalter daerav |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4138482A (en, 2012) |
| JP (1) | JPS5346991A (en, 2012) |
| AR (1) | AR216106A1 (en, 2012) |
| AT (1) | AT362378B (en, 2012) |
| AU (1) | AU512561B2 (en, 2012) |
| BE (1) | BE859569A (en, 2012) |
| CA (1) | CA1075688A (en, 2012) |
| CH (4) | CH623574A5 (en, 2012) |
| DE (1) | DE2745280C2 (en, 2012) |
| DK (1) | DK153786C (en, 2012) |
| ES (1) | ES463133A1 (en, 2012) |
| FI (1) | FI62531C (en, 2012) |
| FR (1) | FR2367749A1 (en, 2012) |
| GB (1) | GB1583590A (en, 2012) |
| GR (1) | GR66109B (en, 2012) |
| HK (1) | HK26384A (en, 2012) |
| HU (1) | HU173607B (en, 2012) |
| IE (1) | IE45709B1 (en, 2012) |
| IL (1) | IL53074A (en, 2012) |
| IT (1) | IT1143697B (en, 2012) |
| LU (1) | LU78280A1 (en, 2012) |
| MC (1) | MC1169A1 (en, 2012) |
| MY (1) | MY8500097A (en, 2012) |
| NL (1) | NL183943C (en, 2012) |
| NO (1) | NO145135C (en, 2012) |
| NZ (1) | NZ185378A (en, 2012) |
| PH (1) | PH13371A (en, 2012) |
| PT (1) | PT67142B (en, 2012) |
| SE (1) | SE427557B (en, 2012) |
| SG (1) | SG60983G (en, 2012) |
| YU (1) | YU40482B (en, 2012) |
| ZA (1) | ZA775974B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4505909A (en) * | 1980-09-17 | 1985-03-19 | Bernstein Joel E | Method and composition for treating and preventing irritation of the eyes |
| US4370324A (en) * | 1980-09-17 | 1983-01-25 | Bernstein Joel E | Method and composition for treating and preventing irritation of the eyes |
| JPH03129724U (en, 2012) * | 1990-04-09 | 1991-12-26 | ||
| US10639313B2 (en) | 2017-09-01 | 2020-05-05 | Ndsu Research Foundation | Compound for inhibition of delta-5-desaturase (D5D) and treatment of cancer and inflammation |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK34863C (da) * | 1924-09-12 | 1925-08-17 | Carl Christian Marius Nielsen | Anordning ved Bagagebærere til Cykler, Motorcykler og lignende. |
| DK93077C (da) * | 1958-12-06 | 1962-03-26 | Geigy Ag J R | Fremgangsmåde til fremstilling af 5H-dibenzo[b,f]azepinforbindelser eller 10,11-dihydroforbindelser heraf eller salte heraf. |
| DE1161278B (de) * | 1958-12-06 | 1964-01-16 | J R Geigy A G Basel (Schweiz) | Verfahren zur Herstellung von Azepinderivaten und deren Salzen. |
| CH375360A (de) * | 1959-01-12 | 1964-02-29 | Geigy Ag J R | Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen |
| FR84219E (fr) | 1963-01-14 | 1964-12-24 | Rhone Poulenc Sa | Nouveau procédé d'aminoalcoylation d'amines hétérocycliques |
| FR1359676A (fr) * | 1963-01-14 | 1964-04-30 | Rhone Poulenc Sa | Nouveau procédé d'aminoalcoylation d'amines hétérocycliques |
-
1976
- 1976-10-12 CH CH1287676A patent/CH623574A5/de not_active IP Right Cessation
-
1977
- 1977-09-09 FI FI772675A patent/FI62531C/fi not_active IP Right Cessation
- 1977-09-16 NL NLAANVRAGE7710194,A patent/NL183943C/xx not_active IP Right Cessation
- 1977-09-19 YU YU2209/77A patent/YU40482B/xx unknown
- 1977-09-30 IT IT7728172A patent/IT1143697B/it active
- 1977-10-04 CA CA288,106A patent/CA1075688A/en not_active Expired
- 1977-10-05 ZA ZA00775974A patent/ZA775974B/xx unknown
- 1977-10-05 AU AU29391/77A patent/AU512561B2/en not_active Expired
- 1977-10-06 IL IL7753074A patent/IL53074A/xx unknown
- 1977-10-07 IE IE2051/77A patent/IE45709B1/en unknown
- 1977-10-07 PH PH20315A patent/PH13371A/en unknown
- 1977-10-07 DE DE2745280A patent/DE2745280C2/de not_active Expired
- 1977-10-07 NZ NZ185378A patent/NZ185378A/xx unknown
- 1977-10-10 MC MC771263A patent/MC1169A1/xx unknown
- 1977-10-10 FR FR7730429A patent/FR2367749A1/fr active Granted
- 1977-10-10 LU LU7778280A patent/LU78280A1/xx unknown
- 1977-10-10 HU HU77HO2017A patent/HU173607B/hu not_active IP Right Cessation
- 1977-10-11 NO NO77773473A patent/NO145135C/no unknown
- 1977-10-11 ES ES77463133A patent/ES463133A1/es not_active Expired
- 1977-10-11 GB GB42276/77A patent/GB1583590A/en not_active Expired
- 1977-10-11 SE SE7711433A patent/SE427557B/xx not_active IP Right Cessation
- 1977-10-11 AT AT726177A patent/AT362378B/de active
- 1977-10-11 US US05/840,790 patent/US4138482A/en not_active Expired - Lifetime
- 1977-10-11 DK DK451477A patent/DK153786C/da active
- 1977-10-11 GR GR54557A patent/GR66109B/el unknown
- 1977-10-11 BE BE181609A patent/BE859569A/xx not_active IP Right Cessation
- 1977-10-11 PT PT67142A patent/PT67142B/pt unknown
- 1977-10-12 AR AR269561A patent/AR216106A1/es active
- 1977-10-12 JP JP12157377A patent/JPS5346991A/ja active Granted
-
1980
- 1980-11-14 CH CH846980A patent/CH625227A5/de not_active IP Right Cessation
- 1980-11-14 CH CH847080A patent/CH627169A5/de not_active IP Right Cessation
- 1980-11-14 CH CH846880A patent/CH625226A5/de not_active IP Right Cessation
-
1983
- 1983-09-28 SG SG609/83A patent/SG60983G/en unknown
-
1984
- 1984-03-22 HK HK263/84A patent/HK26384A/xx unknown
-
1985
- 1985-12-30 MY MY97/85A patent/MY8500097A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: F. HOFFMANN-LA ROCHE AG |