GB1415256A - Alpha-aminomethylbenzyl alcohol derivatives - Google Patents
Alpha-aminomethylbenzyl alcohol derivativesInfo
- Publication number
- GB1415256A GB1415256A GB273373A GB273373A GB1415256A GB 1415256 A GB1415256 A GB 1415256A GB 273373 A GB273373 A GB 273373A GB 273373 A GB273373 A GB 273373A GB 1415256 A GB1415256 A GB 1415256A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- benzyl
- methyl
- substituted
- benzyloxy
- 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
- -1 Alpha-aminomethylbenzyl alcohol derivatives Chemical class 0.000 title abstract 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 12
- 150000001875 compounds Chemical class 0.000 abstract 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 4
- 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 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 3
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 3
- 235000019253 formic acid Nutrition 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- QISAUDWTBBNJIR-UHFFFAOYSA-N 2-phenylmethoxyacetyl chloride Chemical compound ClC(=O)COCC1=CC=CC=C1 QISAUDWTBBNJIR-UHFFFAOYSA-N 0.000 abstract 2
- 125000004442 acylamino group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical class BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 abstract 2
- FHYHAHSFIZKYIF-UHFFFAOYSA-N 2-[tert-butyl-[(4-nitrophenyl)methyl]amino]-1-phenylethanone Chemical compound C=1C=C([N+]([O-])=O)C=CC=1CN(C(C)(C)C)CC(=O)C1=CC=CC=C1 FHYHAHSFIZKYIF-UHFFFAOYSA-N 0.000 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- 229910010082 LiAlH Inorganic materials 0.000 abstract 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- 150000008062 acetophenones Chemical class 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000003938 benzyl alcohols Chemical class 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 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
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1312172A JPS5653537B2 (enrdf_load_stackoverflow) | 1972-02-05 | 1972-02-05 | |
| JP3941672A JPS49237A (enrdf_load_stackoverflow) | 1972-04-19 | 1972-04-19 | |
| JP5101372A JPS495934A (enrdf_load_stackoverflow) | 1972-05-23 | 1972-05-23 | |
| JP5292572A JPS497239A (enrdf_load_stackoverflow) | 1972-05-27 | 1972-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1415256A true GB1415256A (en) | 1975-11-26 |
Family
ID=27455937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB273373A Expired GB1415256A (en) | 1972-02-05 | 1973-01-18 | Alpha-aminomethylbenzyl alcohol derivatives |
Country Status (3)
| Country | Link |
|---|---|
| DK (1) | DK135578B (enrdf_load_stackoverflow) |
| FR (1) | FR2173993B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1415256A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0037740A3 (en) * | 1980-04-07 | 1982-05-12 | Yamanouchi Pharmaceutical Co. Ltd. | Solid microdose drug preparation |
| WO2009032764A1 (en) | 2007-08-28 | 2009-03-12 | Sepracor Inc. | Acetamide stereoisomer |
| EP2266590A2 (en) | 2002-02-22 | 2010-12-29 | Shire LLC | Active agent delivery sytems and methods for protecting and administering active agents |
| US8173829B2 (en) | 2007-08-28 | 2012-05-08 | Sunovion Pharmaceuticals Inc. | Carbamate stereoisomer |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3943173A (en) * | 1972-11-22 | 1976-03-09 | Smithkline Corporation | 3-Alkylamino- alpha-aminomethyl-4-hydroxybenzyl alcohols |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE739678A (fr) * | 1969-10-01 | 1970-04-01 | Amino-alcools et leur preparation |
-
1973
- 1973-01-18 GB GB273373A patent/GB1415256A/en not_active Expired
- 1973-02-02 DK DK55873A patent/DK135578B/da unknown
- 1973-02-05 FR FR7303981A patent/FR2173993B1/fr not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0037740A3 (en) * | 1980-04-07 | 1982-05-12 | Yamanouchi Pharmaceutical Co. Ltd. | Solid microdose drug preparation |
| EP2266590A2 (en) | 2002-02-22 | 2010-12-29 | Shire LLC | Active agent delivery sytems and methods for protecting and administering active agents |
| EP2316469A1 (en) | 2002-02-22 | 2011-05-04 | Shire LLC | Delivery system and methods for protecting and administering dextroamphetamine |
| EP2316468A1 (en) | 2002-02-22 | 2011-05-04 | Shire LLC | Delivery system and methods for protecting and administering dextroamphetamine |
| WO2009032764A1 (en) | 2007-08-28 | 2009-03-12 | Sepracor Inc. | Acetamide stereoisomer |
| US8173829B2 (en) | 2007-08-28 | 2012-05-08 | Sunovion Pharmaceuticals Inc. | Carbamate stereoisomer |
Also Published As
| Publication number | Publication date |
|---|---|
| DK135578C (enrdf_load_stackoverflow) | 1977-10-31 |
| DK135578B (da) | 1977-05-23 |
| FR2173993B1 (enrdf_load_stackoverflow) | 1976-12-03 |
| FR2173993A1 (enrdf_load_stackoverflow) | 1973-10-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| CTFF | Certificate filed |
Free format text: SPC/GB93/009, 930115 |
|
| PE20 | Patent expired after termination of 20 years |
Effective date: 19930116 |
|
| CTFR | Application for certificate rejected |
Free format text: SPC/GB93/009, 930908 |
|
| CTFR | Application for certificate rejected |
Free format text: SPC/GB93/009, 19930908 |