GB922600A - Ortho-tertiary-butyl phenolethers - Google Patents
Ortho-tertiary-butyl phenolethersInfo
- Publication number
- GB922600A GB922600A GB16171/60A GB1617160A GB922600A GB 922600 A GB922600 A GB 922600A GB 16171/60 A GB16171/60 A GB 16171/60A GB 1617160 A GB1617160 A GB 1617160A GB 922600 A GB922600 A GB 922600A
- Authority
- GB
- United Kingdom
- Prior art keywords
- butyl
- tert
- methyl
- phenol
- group
- 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 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- -1 hydroxy, amino Chemical group 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 abstract 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical class CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 abstract 1
- 230000000994 depressogenic effect Effects 0.000 abstract 1
- 125000005265 dialkylamine group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 abstract 1
- YOMFVLRTMZWACQ-UHFFFAOYSA-N ethyltrimethylammonium Chemical compound CC[N+](C)(C)C YOMFVLRTMZWACQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical class CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229960000482 pethidine Drugs 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
- 210000002820 sympathetic nervous system Anatomy 0.000 abstract 1
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises ortho tert. butyl ethylamines of the general formula <FORM:0922600/IV(a)/1> where R1 and R2, which may be the same or different, represent a hydrogen atom or an alkyl group containing 1-4 carbon atoms or a phenethyl group, or R1 and R2 together with a nitrogen atom form a heterocyclic ring, R3 represents a hydrogen atom or an alkyl group containing 1-4 carbon atoms, R4 and R5 may be a hydrogen or an alkyl group containing 1-4 carbon atoms or an alkoxy, hydroxy, amino or acylamino group, together with the acid addition salts and quaternary compounds derived by quaternisation with a compound R6X where R6 represents an alkyl group and X represents the anion associated with the quaternary compound. The compounds may be prepared by (1) reacting the substituted o-tert. butyl phenol with a b -dialkylamino alkyl halide, (2) by converting the phenol to the phenol ether containing a reactive group in the b -position, such as halo or p-toluene sulphonyloxy group, which is subsequently reacted with an alkyl or dialkyl-amine or (3) by converting the phenol to the a -cyanoalkyl ether which is subsequently reduced and the primary amino group converted to a secondary or tertiary amino group if desired. Examples describe the preparation of 2-(b -diethylaminoethoxy)-4-methyl-, 2-(b -aminoethoxy)-4-methyl-, 2-(b -phenethylaminoethoxy)- 4-methyl-, 4-acetamido-2-(b -diethylaminoethoxy)- and 2-(b -diethylaminoethoxy)- 4-hydroxytert. butyl benzene and 2-(2-t. butyl-5-methylphenoxy)-ethyl-triethylammonium iodide, 2-(b - phenethylamino-ethoxy)-4-methyl-tert. butyl benzene isethionate, 2-(2-t. butyl-5-hydroxy-4-methylphenoxy)- ethyl triethylammonium iodide, 2-(2-t. butyl-4-methoxy phenoxy) ethyl trimethylammonium isethionate and 2-(b -N-piperidino-ethoxy)-tert. butyl benzene citrate. A further list of compounds falling within the general formula is also given. The above compounds and their acid addition salts have central nervous depressant and analgesic properties while the quaternary salts have long-acting local anaesthetic and sympathetic nervous system blocking properties. The pharmacological properties are compared with those of pethidine and chloropromazine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16171/60A GB922600A (en) | 1960-05-06 | 1960-05-06 | Ortho-tertiary-butyl phenolethers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16171/60A GB922600A (en) | 1960-05-06 | 1960-05-06 | Ortho-tertiary-butyl phenolethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB922600A true GB922600A (en) | 1963-04-03 |
Family
ID=10072459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16171/60A Expired GB922600A (en) | 1960-05-06 | 1960-05-06 | Ortho-tertiary-butyl phenolethers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB922600A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3408387A (en) * | 1964-09-30 | 1968-10-29 | Ici Ltd | Amidoaroxyalkanolamines |
| EP0062596A1 (en) * | 1981-04-06 | 1982-10-13 | Cortial S.A. | Derivatives of 4-aminoethoxy-5-isopropyl-2-methyl phenol, process for their preparation and their use as medicines |
| WO1988003756A1 (en) * | 1986-11-21 | 1988-06-02 | A/S Cheminova | Amino-alkylated hydroxy compounds and their use as fungicides |
| US6887871B2 (en) | 2000-02-23 | 2005-05-03 | Astrazeneca Ab | Use of phenylheteroakylamine derivatives |
| US6900243B2 (en) | 2000-02-23 | 2005-05-31 | Astrazeneca Ab | Phenylheteroalkylamine derivatives |
| US6953797B2 (en) | 2000-02-23 | 2005-10-11 | Astrazeneca Ab | Use of phenylheteroalkylamine derivatives |
| US7223794B2 (en) | 2001-07-31 | 2007-05-29 | Astrazeneca Ab | Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase |
-
1960
- 1960-05-06 GB GB16171/60A patent/GB922600A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3408387A (en) * | 1964-09-30 | 1968-10-29 | Ici Ltd | Amidoaroxyalkanolamines |
| EP0062596A1 (en) * | 1981-04-06 | 1982-10-13 | Cortial S.A. | Derivatives of 4-aminoethoxy-5-isopropyl-2-methyl phenol, process for their preparation and their use as medicines |
| WO1988003756A1 (en) * | 1986-11-21 | 1988-06-02 | A/S Cheminova | Amino-alkylated hydroxy compounds and their use as fungicides |
| EP0269363A3 (en) * | 1986-11-21 | 1989-11-23 | A/S Cheminova | Amino-alkylated hydroxy compounds and their use as fungicides |
| US6887871B2 (en) | 2000-02-23 | 2005-05-03 | Astrazeneca Ab | Use of phenylheteroakylamine derivatives |
| US6900243B2 (en) | 2000-02-23 | 2005-05-31 | Astrazeneca Ab | Phenylheteroalkylamine derivatives |
| US6953797B2 (en) | 2000-02-23 | 2005-10-11 | Astrazeneca Ab | Use of phenylheteroalkylamine derivatives |
| US7223794B2 (en) | 2001-07-31 | 2007-05-29 | Astrazeneca Ab | Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase |
| WO2003011210A3 (en) * | 2001-07-31 | 2007-10-25 | Astrazeneca Ab | Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES8104280A1 (en) | Tetrahydropyridine and tetrahydropiperidine derivatives, their acid addition salts, processes for their preparation and pharmaceutical compositions containing them. | |
| GB922600A (en) | Ortho-tertiary-butyl phenolethers | |
| GB1392674A (en) | Dopamine derivatives | |
| GB1178371A (en) | Polymers of Piperidine Derivatives | |
| GB1062713A (en) | 4'-hydroxy-4'-piperidyl-ketones | |
| GB830709A (en) | Improvements in or relating to piperidine-carboxamide derivatives | |
| GB1108040A (en) | Derivatives of oripavine and thebaine | |
| GB945068A (en) | Fungicidal and bactericidal compositions | |
| GB1144039A (en) | New naphthyl- and tetrahydronaphthyl-formamidines | |
| ES334038A1 (en) | Procedure for preparing a quaternary ammonium halide. (Machine-translation by Google Translate, not legally binding) | |
| GB823191A (en) | New phenthiazine derivatives and processes for their preparation | |
| GB984119A (en) | Substituted piperidines and methods for their preparation | |
| GB1528862A (en) | 1,4-disubstituted piperazine derivatives and process for their preparation | |
| GB1014918A (en) | 3-(3-hydroxyphenyl)-1-phenacyl-piperidine compounds and their preparation | |
| GB959993A (en) | Camphor derivatives | |
| ES477709A1 (en) | Benzothiazepines | |
| GB1098983A (en) | Isoxazole compounds, their non-toxic salts, and the preparation thereof | |
| ES250754A1 (en) | PROCEDURE FOR OBTAINING PHENOLIC ETHERS OF ACILAMINE | |
| GB1187198A (en) | Substituted Anilides and preparation thereof | |
| ES275437A1 (en) | Amino-alkylidene-dibenzocycloheptene derivatives | |
| GB1223889A (en) | Process for the preparation of aziridine derivatives | |
| GB932016A (en) | Process for the preparation of boric phenthiazines | |
| GB1142610A (en) | Ketoxime ethers | |
| GB835860A (en) | A method of producing pharmaceutically active tropinyl ethers | |
| GB1078890A (en) | Novel 1-cycloalkenyl-piperidines and process for the manufacture thereof |