HU186058B - Process for preparing moega-cyano-1, omega-diphenyl-azalkane derivatives - Google Patents
Process for preparing moega-cyano-1, omega-diphenyl-azalkane derivatives Download PDFInfo
- Publication number
- HU186058B HU186058B HU821109A HU110982A HU186058B HU 186058 B HU186058 B HU 186058B HU 821109 A HU821109 A HU 821109A HU 110982 A HU110982 A HU 110982A HU 186058 B HU186058 B HU 186058B
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- Hungary
- Prior art keywords
- formula
- omega
- cyano
- defined above
- obsession
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- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 50
- -1 methylenedioxy, ethylenedioxy Chemical group 0.000 claims description 37
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 29
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 15
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000004305 biphenyl Substances 0.000 claims description 12
- 230000002829 reductive effect Effects 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000005661 deetherification reaction Methods 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 6
- 239000003085 diluting agent Substances 0.000 claims 3
- 239000000945 filler Substances 0.000 claims 3
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 36
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- 239000000243 solution Substances 0.000 description 17
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 5
- XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 5
- 229940039750 aconitine Drugs 0.000 description 5
- STDXGNLCJACLFY-UHFFFAOYSA-N aconitine Natural products CCN1CC2(COC)C(O)CC(O)C34C5CC6(O)C(OC)C(O)C(OC(=O)C)(C5C6OC(=O)c7ccccc7)C(C(OC)C23)C14 STDXGNLCJACLFY-UHFFFAOYSA-N 0.000 description 5
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- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 5
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
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- BFDNZQUBFCYTIC-UHFFFAOYSA-N 1-bromotridecane Chemical compound CCCCCCCCCCCCCBr BFDNZQUBFCYTIC-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
- 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 2
- FVIXMJHVWQCIJN-UHFFFAOYSA-N 5-cyano-5-(3-methoxyphenyl)heptadecanoic acid Chemical compound CCCCCCCCCCCCC(CCCC(O)=O)(C#N)C1=CC=CC(OC)=C1 FVIXMJHVWQCIJN-UHFFFAOYSA-N 0.000 description 2
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
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- HRNUZLNPJAFQML-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-ethylethanamine Chemical compound CCNCCC1=CC=C(OC)C(OC)=C1 HRNUZLNPJAFQML-UHFFFAOYSA-N 0.000 description 1
- LFVQQGLSBGESDZ-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(3-methoxyphenyl)tetradecanenitrile Chemical compound CCCCCCCCCCCCC(CCCCl)(C#N)C1=CC=CC(OC)=C1 LFVQQGLSBGESDZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
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- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3114497 | 1981-04-10 | ||
| DE19813144150 DE3144150A1 (de) | 1981-04-10 | 1981-11-06 | (omega)-cyan-1,(omega)-diphenyl-azaalkan-derivate, ihre herstellung und diese enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU186058B true HU186058B (en) | 1985-05-28 |
Family
ID=25792602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU821109A HU186058B (en) | 1981-04-10 | 1982-04-09 | Process for preparing moega-cyano-1, omega-diphenyl-azalkane derivatives |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4438131A (enEXAMPLES) |
| EP (1) | EP0064158B1 (enEXAMPLES) |
| AU (1) | AU546383B2 (enEXAMPLES) |
| CA (1) | CA1184186A (enEXAMPLES) |
| CS (4) | CS238636B2 (enEXAMPLES) |
| DD (1) | DD201778A5 (enEXAMPLES) |
| DE (2) | DE3144150A1 (enEXAMPLES) |
| DK (1) | DK156513C (enEXAMPLES) |
| ES (4) | ES511260A0 (enEXAMPLES) |
| FI (1) | FI76550C (enEXAMPLES) |
| GB (1) | GB2100252B (enEXAMPLES) |
| GR (1) | GR75531B (enEXAMPLES) |
| HU (1) | HU186058B (enEXAMPLES) |
| IE (1) | IE54044B1 (enEXAMPLES) |
| MX (1) | MX9203501A (enEXAMPLES) |
| NO (1) | NO152129C (enEXAMPLES) |
| PH (1) | PH19739A (enEXAMPLES) |
| SG (1) | SG78584G (enEXAMPLES) |
| SU (1) | SU1308195A3 (enEXAMPLES) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3344755A1 (de) * | 1983-12-10 | 1985-06-20 | Basf Ag, 6700 Ludwigshafen | 1,7-diphenyl-3-methylaza-7-cyan-8-methyl-nonan zur verwendung bei der bekaempfung von krankheiten |
| DE3433383A1 (de) * | 1984-09-12 | 1986-03-20 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue phenyl-acetonitril-derivate |
| US4612329A (en) * | 1984-10-17 | 1986-09-16 | Hokuriku Pharmaceutical Co., Ltd. | Pharmaceutical alpha-aminoalkyl-alpha-alkylphenylacetonitriles |
| US4760089A (en) * | 1985-09-09 | 1988-07-26 | Smithkline Beckman Corporation | Irreversible dopamine-β-hydroxylase inhibitors |
| FR2588258B1 (fr) * | 1985-10-04 | 1989-12-15 | Adir | Nouveaux derives d'amino-5 valeronitrile, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
| DE3535950A1 (de) * | 1985-10-09 | 1987-04-09 | Basf Ag | Kombinationspraeparat |
| EP0271591B1 (de) * | 1986-12-13 | 1989-09-20 | BASF Aktiengesellschaft | Kombinationspräparat |
| DE3535949A1 (de) * | 1985-10-09 | 1987-04-09 | Basf Ag | Kombinationspraeparat |
| US4593042A (en) * | 1985-10-18 | 1986-06-03 | G. D. Searle & Co. | Bicyclo-substituted phenylacetonitrile derivatives |
| NZ217960A (en) * | 1985-10-18 | 1990-01-29 | Searle & Co | Bicyclo-substituted phenylacetonitriles and pharmaceutical compositions |
| DE3542994A1 (de) * | 1985-12-05 | 1987-06-11 | Basf Ag | Basisch substituierte phenylacetaldehyde, ihre herstellung und diese enthaltende arzneimittel |
| DE3603032A1 (de) * | 1986-01-31 | 1987-08-06 | Basf Ag | Basisch substituierte phenylacetonitrile, ihre herstellung und diese enthaltende arzneimittel |
| CS258534B1 (en) * | 1986-07-18 | 1988-08-16 | Ludvik Blaha | Derivatives of valeronitrile and method of their preparation |
| DE3634389A1 (de) * | 1986-10-09 | 1988-04-21 | Knoll Ag | Verwendung von anipamil |
| DE3642331A1 (de) * | 1986-12-11 | 1988-06-23 | Basf Ag | Basisch substituierte phenylacetonitrile, ihre herstellung und diese enthaltende arzneimittel |
| US5486539A (en) * | 1989-12-21 | 1996-01-23 | G. D. Searle & Co. | Method of using phenylacetonitrilealkylaminoalkyl-ortho-substituted aryl compounds as immunosuppressives |
| US5247119A (en) * | 1990-12-12 | 1993-09-21 | G. D. Searle & Co. | Phenylacetonitrilehydroxyalkylaminoalkyl-ortho-substituted aryl compounds as immunosuppressives |
| CS164891A3 (en) * | 1991-05-31 | 1992-12-16 | Vyzk Ustav Farm Biochem Sp | N-arylalkyl derivatives of 2-aminomethyl-1,4-benzodioxan, and process forpreparing thereof |
| DE4124252A1 (de) * | 1991-07-22 | 1993-01-28 | Knoll Ag | Verfahren zur herstellung einer sterilfiltrierbaren wirkstoffloesung |
| DE4234000A1 (de) * | 1992-10-09 | 1994-04-14 | Knoll Ag | Verfahren zur Racemattrennung von Anipamil |
| NZ582033A (en) * | 2007-06-20 | 2012-07-27 | Milestone Pharmaceuticals Inc | Short acting phenylalkylamine calcium channel blockers and uses thereof |
| US9504747B2 (en) | 2013-03-08 | 2016-11-29 | Novartis Ag | Lipids and lipid compositions for the delivery of active agents |
| US10124065B2 (en) * | 2013-03-08 | 2018-11-13 | Novartis Ag | Lipids and lipid compositions for the delivery of active agents |
| EP3169309B1 (en) | 2014-07-16 | 2023-05-10 | Novartis AG | Method of encapsulating a nucleic acid in a lipid nanoparticle host |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA916719A (en) | 1972-12-12 | Dengel Ferdinand | Basically substituted phenylacetonitriles and method for their preparation | |
| DE1154810B (de) | 1961-04-01 | 1963-09-26 | Knoll Ag | Verfahren zur Herstellung basisch substituierter Phenylacetonitrile |
| DE1643429A1 (de) * | 1967-09-20 | 1971-01-28 | Knoll Ag | Basisch substituierte Phenylacetonitrile und Verfahren zu deren Herstellung |
| GB1202500A (en) | 1967-12-08 | 1970-08-19 | Knoll Ag | Substituted phenylacetonitriles |
| GB1202750A (en) | 1967-12-11 | 1970-08-19 | Knoll Ag | Substituted phenylacetonitriles |
| DE2059985C3 (de) | 1970-12-05 | 1979-10-04 | Knoll Ag, 6700 Ludwigshafen | Rechtsdrehende, basisch substituierte Phenylacetonitrile, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE2059923C3 (de) | 1970-12-05 | 1979-01-25 | Knoll Ag, 6700 Ludwigshafen | l-a-Isopropyl-o-[(N-methyl-N-homoveratryl)v-aminopropyl] -3,4-dimethoxyphenylacetonitril, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel |
| DE2946545A1 (de) * | 1979-11-17 | 1981-05-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung der enantiomeren formen von 4-cyan-1-(n-methyl-n-(2'-((3'',4'',-dimethoxyphenyl))-aethyl)-amino)-5-methyl-4-(3',4',5'-trimethoxyphenyl)-hexan und dessen salzen |
-
1981
- 1981-11-06 DE DE19813144150 patent/DE3144150A1/de not_active Withdrawn
-
1982
- 1982-03-17 GR GR67618A patent/GR75531B/el unknown
- 1982-03-23 CA CA000399115A patent/CA1184186A/en not_active Expired
- 1982-03-30 US US06/363,501 patent/US4438131A/en not_active Expired - Lifetime
- 1982-03-31 DE DE8282102699T patent/DE3262516D1/de not_active Expired
- 1982-03-31 NO NO821085A patent/NO152129C/no unknown
- 1982-03-31 EP EP82102699A patent/EP0064158B1/de not_active Expired
- 1982-04-06 PH PH27104A patent/PH19739A/en unknown
- 1982-04-06 CS CS827839A patent/CS238636B2/cs unknown
- 1982-04-06 CS CS827838A patent/CS238635B2/cs unknown
- 1982-04-06 CS CS822458A patent/CS238621B2/cs unknown
- 1982-04-06 CS CS827837A patent/CS238634B2/cs unknown
- 1982-04-07 DD DD82238830A patent/DD201778A5/de not_active IP Right Cessation
- 1982-04-07 FI FI821252A patent/FI76550C/fi not_active IP Right Cessation
- 1982-04-07 DK DK159882A patent/DK156513C/da not_active IP Right Cessation
- 1982-04-07 ES ES511260A patent/ES511260A0/es active Granted
- 1982-04-08 IE IE856/82A patent/IE54044B1/en not_active IP Right Cessation
- 1982-04-08 GB GB8210449A patent/GB2100252B/en not_active Expired
- 1982-04-08 AU AU82490/82A patent/AU546383B2/en not_active Ceased
- 1982-04-09 HU HU821109A patent/HU186058B/hu not_active IP Right Cessation
- 1982-04-09 SU SU823419898A patent/SU1308195A3/ru active
-
1983
- 1983-04-15 ES ES521543A patent/ES521543A0/es active Granted
- 1983-04-15 ES ES521544A patent/ES8402261A1/es not_active Expired
- 1983-04-15 ES ES521545A patent/ES8402262A1/es not_active Expired
-
1984
- 1984-11-05 SG SG785/84A patent/SG78584G/en unknown
-
1992
- 1992-06-26 MX MX9203501A patent/MX9203501A/es unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |