DE1111209B - Verfahren zur Herstellung eines neuen Phenylalkylolamins mit hustenreizstillenden Eigenschaften - Google Patents
Verfahren zur Herstellung eines neuen Phenylalkylolamins mit hustenreizstillenden EigenschaftenInfo
- Publication number
- DE1111209B DE1111209B DEL33685A DEL0033685A DE1111209B DE 1111209 B DE1111209 B DE 1111209B DE L33685 A DEL33685 A DE L33685A DE L0033685 A DEL0033685 A DE L0033685A DE 1111209 B DE1111209 B DE 1111209B
- Authority
- DE
- Germany
- Prior art keywords
- phenylalkylolamine
- new
- phenyl
- preparation
- dimethyl
- 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 7
- 230000000954 anitussive effect Effects 0.000 title claims description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- -1 lithium Hydrogenated aluminum hydride Chemical class 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 206010011224 Cough Diseases 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000003434 antitussive agent Substances 0.000 description 4
- 229940124584 antitussives Drugs 0.000 description 4
- 229960004126 codeine Drugs 0.000 description 4
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 4
- AKNNEGZIBPJZJG-MSOLQXFVSA-N (-)-noscapine Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2[C@@H]1[C@@H]1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-MSOLQXFVSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- YFAKHWQTDGNFFU-UHFFFAOYSA-N [2-[(dimethylamino)methyl]-2-phenylbutyl] benzoate Chemical compound C=1C=CC=CC=1C(CC)(CN(C)C)COC(=O)C1=CC=CC=C1 YFAKHWQTDGNFFU-UHFFFAOYSA-N 0.000 description 3
- AKNNEGZIBPJZJG-UHFFFAOYSA-N alpha-noscapine Natural products CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000003533 narcotic effect Effects 0.000 description 3
- PLPRGLOFPNJOTN-UHFFFAOYSA-N narcotine Natural products COc1ccc2C(OC(=O)c2c1OC)C3Cc4c(CN3C)cc5OCOc5c4OC PLPRGLOFPNJOTN-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- YQSHYGCCYVPRDI-UHFFFAOYSA-N (4-propan-2-ylphenyl)methanamine Chemical compound CC(C)C1=CC=C(CN)C=C1 YQSHYGCCYVPRDI-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001071864 Lethrinus laticaudis Species 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-n-butyl-N-methylamine Natural products CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- PGEAEAYLSCKCCO-UHFFFAOYSA-N benzene;n-methylmethanamine Chemical compound CNC.C1=CC=CC=C1 PGEAEAYLSCKCCO-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960003782 dextromethorphan hydrobromide Drugs 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- MXWOWJHBMBNVQZ-UHFFFAOYSA-N ethyl 2-carbonochloridoyl-2-phenylbutanoate Chemical compound C(=O)(OCC)C(C(=O)Cl)(CC)C1=CC=CC=C1 MXWOWJHBMBNVQZ-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 210000000867 larynx Anatomy 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB22992/58A GB863223A (en) | 1958-07-17 | 1958-07-17 | N,n-dimethyl-2-phenyl-2-benzoyloxymethylbutylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1111209B true DE1111209B (de) | 1961-07-20 |
Family
ID=10188366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEL33685A Pending DE1111209B (de) | 1958-07-17 | 1959-07-09 | Verfahren zur Herstellung eines neuen Phenylalkylolamins mit hustenreizstillenden Eigenschaften |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE580501A (enrdf_load_stackoverflow) |
| CH (1) | CH381709A (enrdf_load_stackoverflow) |
| DE (1) | DE1111209B (enrdf_load_stackoverflow) |
| ES (1) | ES250851A1 (enrdf_load_stackoverflow) |
| FR (1) | FR147M (enrdf_load_stackoverflow) |
| GB (1) | GB863223A (enrdf_load_stackoverflow) |
| NL (1) | NL109182C (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1622230B1 (de) * | 1968-02-02 | 1970-10-15 | Metz App Werke Inh Paul Metz | Automatisches Blitzlichtgeraet |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2588556B1 (fr) * | 1985-10-11 | 1988-01-08 | Sanofi Sa | Derives du naphtalene substitues par un groupement (omega-amino) alcanol a activite antimicrobienne, leur preparation et les compositions les contenant |
| FR2613719B1 (fr) * | 1987-04-10 | 1991-03-22 | Sanofi Sa | Derives aromatiques, leur preparation et leur utilisation comme antimicrobiens |
-
0
- BE BE580501D patent/BE580501A/xx unknown
- NL NL109182D patent/NL109182C/xx active
-
1958
- 1958-07-17 GB GB22992/58A patent/GB863223A/en not_active Expired
-
1959
- 1959-07-09 DE DEL33685A patent/DE1111209B/de active Pending
- 1959-07-14 CH CH7575859A patent/CH381709A/de unknown
- 1959-07-16 ES ES0250851A patent/ES250851A1/es not_active Expired
-
1960
- 1960-08-08 FR FR835249A patent/FR147M/fr active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1622230B1 (de) * | 1968-02-02 | 1970-10-15 | Metz App Werke Inh Paul Metz | Automatisches Blitzlichtgeraet |
Also Published As
| Publication number | Publication date |
|---|---|
| NL109182C (enrdf_load_stackoverflow) | |
| CH381709A (de) | 1964-09-15 |
| ES250851A1 (es) | 1959-12-01 |
| GB863223A (en) | 1961-03-22 |
| BE580501A (enrdf_load_stackoverflow) | |
| FR147M (fr) | 1961-02-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1670616C3 (de) | 14-Hydroxydihydronormorphinverbindungen und Verfahren zu ihrer Herstellung | |
| DE928345C (de) | Verfahren zur Herstellung von 10-(3'-Pyrrolidino-propyl)-phenthiazin und seinen Salzen bzw. seinen quaternaeren Ammoniumverbindungen | |
| DE60133584T2 (de) | 4-arylpiperidine als opioidrezeptorbindende agenzien | |
| DE2257715C2 (de) | N-substituierte 6-Methylen-6-desoxy-14-hydroxydihydronormorphinderivate | |
| DE69530205T2 (de) | Heterocyclisch kondensierte morphinoid-derivate | |
| EP0105210B1 (de) | Isochinolinderivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung | |
| DE1200831B (de) | Verfahren zur Herstellung von Thioxanthenderivaten | |
| DD143254A5 (de) | Verfahren zur herstellung von tetrahydroisochinolin-derivaten | |
| DE1111209B (de) | Verfahren zur Herstellung eines neuen Phenylalkylolamins mit hustenreizstillenden Eigenschaften | |
| CH640507A5 (en) | Process for preparing novel 1-aryloxy-2-hydroxy-3-aminopropanes | |
| DE2534963A1 (de) | Piperazino-pyrimidine und diese verbindungen enthaltende arzneimittel | |
| DE1075621B (de) | Verfahren zur Herstellung von Phenthiazmderivaten | |
| DE2264938A1 (de) | 3-arylaminocarbonyl-4-hydroxy-benzo eckige klammer auf b eckige klammer zu thiacyclohex(3)en-1,1-dioxide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| DE1518311B1 (de) | N-(2-Diaethylaminoaethyl)-2-methoxy-3,4- bzw. 4,5-methylendioxybenzamid und deren pharmakologisch nicht giftige Saeureadditionssalze | |
| AT211824B (de) | Verfahren zur Herstellung des neuen N,N-Dimethyl-2-phenyl-2-benzoyloxymethylbutylamins und seiner Salze | |
| DE1966215A1 (de) | Verfahren zur Herstellung von heterocyclischen Benzamiden | |
| DE2233088A1 (de) | Benzomorphanderivate | |
| DE69619861T2 (de) | 3-(2h)-pyridazinon derivate und diese verbindungen enthaltende pharmazeutische zusammensetzungen | |
| DE1518311C (de) | N (2 Diathylaminoathyl) 2 methoxy 3,4 bzw 4,5 methylendioxybenzamid und deren pharmakologisch nicht giftige Saureadditions salze | |
| DE1695785A1 (de) | Neue,substituierte 2-Aminomethylbenzofuranverbindungen und Verfahren zu deren Herstellung | |
| DE1168434B (de) | Verfahren zur Herstellung von 10-(3'-Piperazinopropyl)-phenthiazinverbindungen | |
| AT300763B (de) | Verfahren zur Herstellung von neuen 5-(1'-Hydroxy-2'-arylalkyl-oder -aryloxyalkylaminoäthyl)-salicylamiden und deren Säureadditionssalzen | |
| AT220150B (de) | Verfahren zur Herstellung von neuen, substituierten Piperidinen | |
| DE2241730A1 (de) | Neue phenothiazinderivate | |
| DE1793706C3 (de) | Verfahren zur Herstellung von N-(2-Diäthylaminoäthyl)-2-methoxy-3,4-bzw. -4,5-methylendioxybenzamid und deren pharmakologisch nicht giftigen Säureadditionssalzen |