GB1399015A - Fluoroalkylated phenylethylamine derivatives - Google Patents
Fluoroalkylated phenylethylamine derivativesInfo
- Publication number
- GB1399015A GB1399015A GB3969872A GB3969872A GB1399015A GB 1399015 A GB1399015 A GB 1399015A GB 3969872 A GB3969872 A GB 3969872A GB 3969872 A GB3969872 A GB 3969872A GB 1399015 A GB1399015 A GB 1399015A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alk
- hydrogen
- oxygen
- reaction
- hydroxy
- 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.)
- Expired
Links
- 150000007925 phenylethylamine derivatives Chemical class 0.000 title 1
- -1 fluoroalkyl radical Chemical class 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract 2
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 230000001813 broncholytic effect Effects 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 abstract 1
- 239000010931 gold Substances 0.000 abstract 1
- 229910052737 gold Inorganic materials 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000021 stimulant Substances 0.000 abstract 1
- 239000000375 suspending agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2143204A DE2143204C3 (de) | 1971-08-28 | 1971-08-28 | N-Fluoralkyl-phenylisopropylamin-Derivate und deren Salze, Verfahren zu deren Herstellung und Arzneimittel auf deren Basis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1399015A true GB1399015A (en) | 1975-06-25 |
Family
ID=5818084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3969872A Expired GB1399015A (en) | 1971-08-28 | 1972-08-25 | Fluoroalkylated phenylethylamine derivatives |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3911016A (cg-RX-API-DMAC7.html) |
| AT (1) | AT318558B (cg-RX-API-DMAC7.html) |
| CA (1) | CA1013770A (cg-RX-API-DMAC7.html) |
| CH (1) | CH587217A5 (cg-RX-API-DMAC7.html) |
| DD (1) | DD100704A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2143204C3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES405983A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2150787B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1399015A (cg-RX-API-DMAC7.html) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019507111A (ja) * | 2015-12-22 | 2019-03-14 | ゾゲニクス インターナショナル リミテッド | 代謝抵抗性フェンフルラミン類縁体およびその使用法 |
| US11406606B2 (en) | 2016-08-24 | 2022-08-09 | Zogenix International Limited | Formulation for inhibiting formation of 5-HT2B agonists and methods of using same |
| US11458111B2 (en) | 2017-09-26 | 2022-10-04 | Zogenix International Limited | Ketogenic diet compatible fenfluramine formulation |
| US11571397B2 (en) | 2018-05-11 | 2023-02-07 | Zogenix International Limited | Compositions and methods for treating seizure-induced sudden death |
| US11612574B2 (en) | 2020-07-17 | 2023-03-28 | Zogenix International Limited | Method of treating patients infected with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) |
| US11634377B2 (en) | 2015-12-22 | 2023-04-25 | Zogenix International Limited | Fenfluramine compositions and methods of preparing the same |
| US12097206B2 (en) | 2013-05-03 | 2024-09-24 | Katholieke Universiteit Leuven | Method for the treatment of Dravet Syndrome |
| US12144787B2 (en) | 2018-11-19 | 2024-11-19 | Zogenix International Limited | Method of treating patients with a mutation in cyclin-dependent kinase-like 5 (CDKL5) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2965655D1 (en) * | 1978-06-28 | 1983-07-21 | Beecham Group Plc | Secondary amines, their preparation, pharmaceutical compositions containing them and their use |
| US4845127A (en) * | 1978-07-03 | 1989-07-04 | Eli Lilly And Company | Phenethanolamines, compositions containing the same and method for effecting weight control |
| EP0198412B1 (de) * | 1985-04-16 | 1989-03-22 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Phenäthanolaminderivate |
| US5220068A (en) * | 1986-09-25 | 1993-06-15 | Chinoin Gyogyszer - Es Vegyeszeti Termekek Gyara Rt. | Psychostimulant agent |
| HU207280B (en) * | 1986-09-25 | 1993-03-29 | Chinoin Gyogyszer Es Vegyeszet | Process for producing new phenyl-alkyl-amines and pharmaceutical compositions containing them |
| EP0507154B1 (de) * | 1991-03-21 | 1996-05-08 | Willi Möller AG | Verfahren zur Bestimmung von Alkoholen und Verwendung einer Vorrichtung zur Alkoholbestimmung |
| US7022492B2 (en) * | 2003-12-15 | 2006-04-04 | Dade Behring Inc. | Ecstasy haptens and immunogens |
| US20050130243A1 (en) * | 2003-12-15 | 2005-06-16 | Zheng Yi F. | Assay for entactogens |
| US6991911B2 (en) * | 2003-12-15 | 2006-01-31 | Dade Behring Inc. | Assay for entactogens |
| US7115383B2 (en) * | 2004-03-22 | 2006-10-03 | Dade Behring Inc. | Assays for amphetamine and methamphetamine |
| US7037669B2 (en) * | 2004-03-22 | 2006-05-02 | Dade Behring Inc. | Assays for amphetamine and methamphetamine using stereospecific reagents |
| JP2008520666A (ja) * | 2004-11-22 | 2008-06-19 | マリンクロッド・インコーポレイテッド | ベンズフェタミン塩酸塩の精製方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3320319A (en) * | 1961-03-29 | 1967-05-16 | Degussa | 1-(aryl)-2-methyl-2-aliphatic amino-propanes |
| US3117160A (en) * | 1961-07-27 | 1964-01-07 | Pfizer & Co C | Aralkylamines |
| GB1050132A (cg-RX-API-DMAC7.html) * | 1963-03-01 | |||
| US3400155A (en) * | 1963-03-01 | 1968-09-03 | Hoechst Ag | N-(1-phenyl-propyl-(2))-n-aminoethyl-(2')-diphenylamines and the salts thereof |
| CH481110A (de) * | 1967-02-17 | 1969-11-15 | Geigy Ag J R | Verfahren zur Herstellung von 1,2,4,5-Tetrahydro-3-azepinen |
-
1971
- 1971-08-28 DE DE2143204A patent/DE2143204C3/de not_active Expired
-
1972
- 1972-07-26 DD DD164703A patent/DD100704A5/xx unknown
- 1972-07-27 US US275453A patent/US3911016A/en not_active Expired - Lifetime
- 1972-08-02 CH CH1142172A patent/CH587217A5/xx not_active IP Right Cessation
- 1972-08-17 FR FR7229432A patent/FR2150787B1/fr not_active Expired
- 1972-08-19 ES ES405983A patent/ES405983A1/es not_active Expired
- 1972-08-25 GB GB3969872A patent/GB1399015A/en not_active Expired
- 1972-08-28 CA CA150,380A patent/CA1013770A/en not_active Expired
- 1972-08-28 AT AT739872A patent/AT318558B/de not_active IP Right Cessation
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12097206B2 (en) | 2013-05-03 | 2024-09-24 | Katholieke Universiteit Leuven | Method for the treatment of Dravet Syndrome |
| JP2019507111A (ja) * | 2015-12-22 | 2019-03-14 | ゾゲニクス インターナショナル リミテッド | 代謝抵抗性フェンフルラミン類縁体およびその使用法 |
| US11325882B2 (en) | 2015-12-22 | 2022-05-10 | Zogenix International Limited | Metabolism resistant fenfluramine analogs and methods of using the same |
| US11634377B2 (en) | 2015-12-22 | 2023-04-25 | Zogenix International Limited | Fenfluramine compositions and methods of preparing the same |
| US11673852B2 (en) | 2015-12-22 | 2023-06-13 | Zogenix International Limited | Metabolism resistant fenfluramine analogs and methods of using the same |
| US11406606B2 (en) | 2016-08-24 | 2022-08-09 | Zogenix International Limited | Formulation for inhibiting formation of 5-HT2B agonists and methods of using same |
| US11759440B2 (en) | 2016-08-24 | 2023-09-19 | Zogenix International Limited | Formulation for inhibiting formation of 5-HT2B agonists and methods of using same |
| US11786487B2 (en) | 2016-08-24 | 2023-10-17 | Zogenix International Limited | Formulation for inhibiting formation of 5-HT2B agonists and methods of using same |
| US11458111B2 (en) | 2017-09-26 | 2022-10-04 | Zogenix International Limited | Ketogenic diet compatible fenfluramine formulation |
| US11571397B2 (en) | 2018-05-11 | 2023-02-07 | Zogenix International Limited | Compositions and methods for treating seizure-induced sudden death |
| US12144787B2 (en) | 2018-11-19 | 2024-11-19 | Zogenix International Limited | Method of treating patients with a mutation in cyclin-dependent kinase-like 5 (CDKL5) |
| US11612574B2 (en) | 2020-07-17 | 2023-03-28 | Zogenix International Limited | Method of treating patients infected with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) |
Also Published As
| Publication number | Publication date |
|---|---|
| DD100704A5 (cg-RX-API-DMAC7.html) | 1973-10-05 |
| DE2143204B2 (de) | 1979-02-01 |
| ES405983A1 (es) | 1975-09-16 |
| DE2143204C3 (de) | 1979-09-27 |
| FR2150787B1 (cg-RX-API-DMAC7.html) | 1975-10-17 |
| CA1013770A (en) | 1977-07-12 |
| US3911016A (en) | 1975-10-07 |
| FR2150787A1 (cg-RX-API-DMAC7.html) | 1973-04-13 |
| AT318558B (de) | 1974-10-25 |
| CH587217A5 (cg-RX-API-DMAC7.html) | 1977-04-29 |
| DE2143204A1 (de) | 1973-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |