GB1355449A - Phenethylaralkylamine compounds and their preparation - Google Patents
Phenethylaralkylamine compounds and their preparationInfo
- Publication number
- GB1355449A GB1355449A GB149472A GB149472A GB1355449A GB 1355449 A GB1355449 A GB 1355449A GB 149472 A GB149472 A GB 149472A GB 149472 A GB149472 A GB 149472A GB 1355449 A GB1355449 A GB 1355449A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- alkyl
- compounds
- hydrogen
- bromophenethyl
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 15
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- -1 C 1-4 perfluoroacyl Chemical group 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 238000000034 method Methods 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 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 abstract 1
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-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-IWFBPKFRSA-N 0.000 abstract 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- NCHOFHFPNJXIDO-UHFFFAOYSA-N 1-[2-[2-(4-bromophenyl)ethyl]phenyl]-n-methylmethanamine Chemical compound CNCC1=CC=CC=C1CCC1=CC=C(Br)C=C1 NCHOFHFPNJXIDO-UHFFFAOYSA-N 0.000 abstract 1
- TXJKWMIIGZPMKR-UHFFFAOYSA-N 2-[2-[2-(4-bromophenyl)ethyl]phenyl]-n-methylethanamine Chemical compound CNCCC1=CC=CC=C1CCC1=CC=C(Br)C=C1 TXJKWMIIGZPMKR-UHFFFAOYSA-N 0.000 abstract 1
- CPZGLCNJDMZKBA-UHFFFAOYSA-N 2-[2-[2-(4-bromophenyl)ethyl]phenyl]ethanamine Chemical compound NCCC1=CC=CC=C1CCC1=CC=C(Br)C=C1 CPZGLCNJDMZKBA-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical compound C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 229920001774 Perfluoroether Polymers 0.000 abstract 1
- 238000006434 Ritter amidation reaction Methods 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- ICBXUSUXJDRLMA-UHFFFAOYSA-N [2-[2-(4-bromophenyl)ethyl]phenyl]methanamine Chemical compound NCC1=CC=CC=C1CCC1=CC=C(Br)C=C1 ICBXUSUXJDRLMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 125000001118 alkylidene group Chemical group 0.000 abstract 1
- 239000003416 antiarrhythmic agent Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 abstract 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 238000011905 homologation Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002636 imidazolinyl group Chemical group 0.000 abstract 1
- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 abstract 1
- 230000001035 methylating effect Effects 0.000 abstract 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002757 morpholinyl group Chemical group 0.000 abstract 1
- GFGRRRKNHSDLAO-UHFFFAOYSA-N n,n-dimethyl-1,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(N(C)C)CCC1=CC=CC=C1 GFGRRRKNHSDLAO-UHFFFAOYSA-N 0.000 abstract 1
- KWZGBHZJTIEOAJ-UHFFFAOYSA-N n-methyl-1-[2-(2-phenylethyl)phenyl]methanamine Chemical compound CNCC1=CC=CC=C1CCC1=CC=CC=C1 KWZGBHZJTIEOAJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Cell Electrode Carriers And Collectors (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10688971A | 1971-01-15 | 1971-01-15 | |
| US20570871A | 1971-12-07 | 1971-12-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1355449A true GB1355449A (en) | 1974-06-05 |
Family
ID=26804135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB149472A Expired GB1355449A (en) | 1971-01-15 | 1972-01-12 | Phenethylaralkylamine compounds and their preparation |
Country Status (18)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0250254A1 (en) * | 1986-06-20 | 1987-12-23 | McNeilab, Inc. | Cis & trans stilbenes and their composition for the treatment of hypertension |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH386443A (de) * | 1959-12-16 | 1965-01-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen tetrasubstituierten Alkylendiaminen |
| US3719712A (en) * | 1969-09-29 | 1973-03-06 | Merck & Co Inc | 2-phenylethynyl-benzyl-amines |
-
1972
- 1972-01-03 NO NO724A patent/NO135027C/no unknown
- 1972-01-03 SE SE7200013A patent/SE388603B/xx unknown
- 1972-01-04 FI FI11/72A patent/FI54701C/fi active
- 1972-01-06 NL NL7200202A patent/NL7200202A/xx not_active Application Discontinuation
- 1972-01-10 IL IL38528A patent/IL38528A/xx unknown
- 1972-01-11 IE IE42/72A patent/IE35972B1/xx unknown
- 1972-01-11 PH PH13180A patent/PH11341A/en unknown
- 1972-01-11 CA CA132,195A patent/CA1008884A/en not_active Expired
- 1972-01-11 AU AU37796/72A patent/AU469273B2/en not_active Expired
- 1972-01-12 GB GB149472A patent/GB1355449A/en not_active Expired
- 1972-01-12 HU HUME1457A patent/HU165402B/hu unknown
- 1972-01-13 AR AR240071A patent/AR192907A1/es active
- 1972-01-13 CH CH1417275A patent/CH573392A5/xx not_active IP Right Cessation
- 1972-01-13 ES ES398855A patent/ES398855A1/es not_active Expired
- 1972-01-13 CH CH54872A patent/CH572889A5/xx not_active IP Right Cessation
- 1972-01-14 FR FR7201242A patent/FR2121849B1/fr not_active Expired
- 1972-01-14 BE BE778049A patent/BE778049A/xx unknown
- 1972-01-14 DE DE2201804A patent/DE2201804C3/de not_active Expired
- 1972-01-17 JP JP627572A patent/JPS5425015B1/ja active Pending
-
1974
- 1974-11-12 PH PH16506A patent/PH11987A/en unknown
- 1974-12-13 ES ES432918A patent/ES432918A1/es not_active Expired
-
1975
- 1975-02-10 SE SE7501439A patent/SE398344B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0250254A1 (en) * | 1986-06-20 | 1987-12-23 | McNeilab, Inc. | Cis & trans stilbenes and their composition for the treatment of hypertension |
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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 |