CH497389A - Verfahren zur Herstellung basisch substituierter Phenylacetonitrile - Google Patents
Verfahren zur Herstellung basisch substituierter PhenylacetonitrileInfo
- Publication number
- CH497389A CH497389A CH1079566A CH1079566A CH497389A CH 497389 A CH497389 A CH 497389A CH 1079566 A CH1079566 A CH 1079566A CH 1079566 A CH1079566 A CH 1079566A CH 497389 A CH497389 A CH 497389A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- molecular weight
- low molecular
- hydrogen
- phenylacetonitrile
- Prior art date
Links
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 239000003218 coronary vasodilator agent Substances 0.000 title abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000007962 benzene acetonitriles Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- -1 methylene dioxy group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 abstract description 2
- 208000001953 Hypotension Diseases 0.000 abstract 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- HNJWKRMESUMDQE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1 HNJWKRMESUMDQE-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- VFXFHWXYUVPJIL-UHFFFAOYSA-N 5-chloro-2-propan-2-yl-2-[3-(trifluoromethyl)phenyl]pentanenitrile Chemical compound ClCCCC(C(C)C)(C#N)C1=CC=CC(C(F)(F)F)=C1 VFXFHWXYUVPJIL-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- WIOOTMZLCZPTDW-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)ethylazanium;chloride Chemical compound Cl.COC1=CC=C(CCN)C=C1OC WIOOTMZLCZPTDW-UHFFFAOYSA-N 0.000 description 1
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 1
- ILKMEIJZBXEJCL-UHFFFAOYSA-N 3-methyl-2-[3-(trifluoromethyl)phenyl]butanenitrile Chemical compound CC(C)C(C#N)C1=CC=CC(C(F)(F)F)=C1 ILKMEIJZBXEJCL-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Jib Cranes (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH824769A CH486425A (de) | 1965-07-31 | 1966-07-26 | Verfahren zur Herstellung basisch substituierter Phenylacetonitrile |
| CH56470A CH487853A (de) | 1965-07-31 | 1966-07-26 | Verfahren zur Herstellung basisch substituierter Phenylacetonitrile |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK0056774 | 1965-07-31 | ||
| US55595566A | 1966-06-08 | 1966-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH497389A true CH497389A (de) | 1970-10-15 |
Family
ID=25984100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1079566A CH497389A (de) | 1965-07-31 | 1966-07-26 | Verfahren zur Herstellung basisch substituierter Phenylacetonitrile |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE684868A (enrdf_load_stackoverflow) |
| BR (1) | BR6681685D0 (enrdf_load_stackoverflow) |
| CH (1) | CH497389A (enrdf_load_stackoverflow) |
| DE (1) | DE1493904A1 (enrdf_load_stackoverflow) |
| DK (1) | DK120241B (enrdf_load_stackoverflow) |
| FI (1) | FI45187C (enrdf_load_stackoverflow) |
| FR (3) | FR313F (enrdf_load_stackoverflow) |
| GB (1) | GB1090609A (enrdf_load_stackoverflow) |
| NL (1) | NL146797B (enrdf_load_stackoverflow) |
| NO (1) | NO118111B (enrdf_load_stackoverflow) |
| SE (1) | SE352886B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3468863D1 (en) * | 1984-06-15 | 1988-02-25 | Heumann Ludwig & Co Gmbh | Method for the preparation of phenylacetonitrile substituted by a basic radical |
| DE3642331A1 (de) * | 1986-12-11 | 1988-06-23 | Basf Ag | Basisch substituierte phenylacetonitrile, ihre herstellung und diese enthaltende arzneimittel |
| HRP20140801T1 (hr) * | 2007-06-20 | 2014-11-21 | Milestone Pharmaceuticals Inc. | Kratkodjelujuä†i fenilalkilaminski blokatori kalcijevih kanala i njihova uporaba |
-
1965
- 1965-07-31 DE DE19651493904 patent/DE1493904A1/de not_active Withdrawn
-
1966
- 1966-07-20 GB GB3256866A patent/GB1090609A/en not_active Expired
- 1966-07-26 CH CH1079566A patent/CH497389A/de not_active IP Right Cessation
- 1966-07-29 SE SE1037466A patent/SE352886B/xx unknown
- 1966-07-29 FI FI201866A patent/FI45187C/fi active
- 1966-07-29 BR BR18168566A patent/BR6681685D0/pt unknown
- 1966-07-29 DK DK395466A patent/DK120241B/da unknown
- 1966-07-29 NO NO16410666A patent/NO118111B/no unknown
- 1966-07-29 NL NL666610730A patent/NL146797B/xx unknown
- 1966-07-29 FR FR313D patent/FR313F/fr not_active Expired
- 1966-07-29 BE BE684868D patent/BE684868A/xx unknown
-
1967
- 1967-06-08 FR FR1553708D patent/FR1553708A/fr not_active Expired
- 1967-09-08 FR FR120463A patent/FR7508M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR6681685D0 (pt) | 1973-10-25 |
| FI45187B (enrdf_load_stackoverflow) | 1971-12-31 |
| FR7508M (enrdf_load_stackoverflow) | 1969-12-15 |
| DE1593921A1 (de) | 1970-10-01 |
| NO118111B (enrdf_load_stackoverflow) | 1969-11-10 |
| FR313F (enrdf_load_stackoverflow) | 1970-05-20 |
| FR1553708A (enrdf_load_stackoverflow) | 1969-01-17 |
| NL6610730A (enrdf_load_stackoverflow) | 1967-02-01 |
| DE1593921B2 (de) | 1976-01-15 |
| FI45187C (fi) | 1972-04-10 |
| DE1493904A1 (de) | 1969-06-19 |
| NL146797B (nl) | 1975-08-15 |
| SE352886B (enrdf_load_stackoverflow) | 1973-01-15 |
| BE684868A (enrdf_load_stackoverflow) | 1967-01-30 |
| DK120241B (da) | 1971-05-03 |
| GB1090609A (en) | 1967-11-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |