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GB1111338A - Aralkyl substituted resorcinols

GB1111338A - Aralkyl substituted resorcinols - Google PatentsAralkyl substituted resorcinols Info

Publication number: GB1111338A
Authority: GB; United Kingdom
Prior art keywords: hydrogen; alkyl; group; carbon; phenyl
Prior art date: 1964-07-24
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

Application number

GB34310/66A

Inventor

George Harry Lord

Arthur Hedley Wragg

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Fisons Pharmaceuticals Ltd

Original Assignee

Fisons Pharmaceuticals Ltd

Priority date (The priority date 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 date listed.)

1964-07-24

Filing date

1964-07-24

Publication date

1968-04-24

1964-07-24 Application filed by Fisons Pharmaceuticals Ltd filed Critical Fisons Pharmaceuticals Ltd

1968-04-24 Publication of GB1111338A publication Critical patent/GB1111338A/en

Status Expired legal-status Critical Current

Links

125000003710 aryl alkyl group Chemical group 0.000 title abstract 2
150000005207 1,3-dihydroxybenzenes Chemical class 0.000 title 1
229910052739 hydrogen Inorganic materials 0.000 abstract 7
239000001257 hydrogen Substances 0.000 abstract 7
150000002431 hydrogen Chemical class 0.000 abstract 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
125000000217 alkyl group Chemical group 0.000 abstract 3
150000001875 compounds Chemical class 0.000 abstract 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
239000002253 acid Substances 0.000 abstract 2
125000002947 alkylene group Chemical group 0.000 abstract 2
125000004432 carbon atom Chemical group C* 0.000 abstract 2
-1 p - tolyl Chemical group 0.000 abstract 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
150000001350 alkyl halides Chemical class 0.000 abstract 1
230000003569 amebicidal effect Effects 0.000 abstract 1
239000011230 binding agent Substances 0.000 abstract 1
229910052799 carbon Inorganic materials 0.000 abstract 1
239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
229910052801 chlorine Inorganic materials 0.000 abstract 1
239000000460 chlorine Substances 0.000 abstract 1
239000012050 conventional carrier Substances 0.000 abstract 1
239000003085 diluting agent Substances 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
125000000623 heterocyclic group Chemical group 0.000 abstract 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
150000002440 hydroxy compounds Chemical class 0.000 abstract 1
125000000468 ketone group Chemical group 0.000 abstract 1
150000002576 ketones Chemical class 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
125000001624 naphthyl group Chemical group 0.000 abstract 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
239000000825 pharmaceutical preparation Substances 0.000 abstract 1
150000003839 salts Chemical class 0.000 abstract 1
125000001424 substituent group Chemical group 0.000 abstract 1
239000011701 zinc Substances 0.000 abstract 1
229910052725 zinc Inorganic materials 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Novel compounds of the formula <FORM:1111338/C2/1> where one of R2 and R3 is a group -OR7, R7 and R1 being hydrogen, alkyl, or a group R8 NR9R10, where R8 is alkylene, and R9 and R10 are H or alkyl or form a saturated heterocyclic ring at least one of R1 and R7 being a group R8NR9R10, R4 and R5 and the other of R2 and R3 are hydrogen, alkyl, aralkyl or halogen, R6 is naphthyl, phenyl, or alkyl- and/or halo-substituted phenyl and Y is a carbon-carbon bond or a group containing carbon and hydrogen only, at least one of R4, R5 the other of R2 and R3 or the substituents on R6 being other than hydrogen if Y contains less than 2 carbon atoms and acid addition salts thereof are produced by the reduction of the corresponding ketone which has a keto group adjacent to Y. The reduction is preferably effected by zinc and concentrated hydrochloric acid, and if a free hydroxy compound is initially formed, it may be alkylated using an alkyl halide e.g. in the presence of an acid-binding agent in acetone solution. Exemplified compounds have R1 and R7 as hydrogen, methyl, hexyl, b -diethylaminoethyl, b - N - morpholinoethyl and b -N-piperidinoethyl, R4 as hydrogen, R5 as hydrogen or chlorine and R6 as phenyl, p-chlorophenyl, p - tolyl or p - ethylphenyl, and Y as the various alkylene groups having 2 to 9 carbon atoms. Pharmaceutical preparations having amoebicidal properties contain the above compounds together with conventional carriers and diluents.

GB34310/66A 1964-07-24 1964-07-24 Aralkyl substituted resorcinols Expired GB1111338A (en) Applications Claiming Priority (1) Application Number Priority Date Filing Date Title GB29814/64A GB1111336A (en) 1964-07-24 1964-07-24 Aryl ketones Publications (1) Publication Number Publication Date GB1111338A true GB1111338A (en) 1968-04-24 Family ID=10297608 Family Applications (3) Application Number Title Priority Date Filing Date GB34310/66A Expired GB1111338A (en) 1964-07-24 1964-07-24 Aralkyl substituted resorcinols GB29814/64A Expired GB1111336A (en) 1964-07-24 1964-07-24 Aryl ketones GB34309/66A Expired GB1111337A (en) 1964-07-24 1964-07-24 Substituted aralkyl alcohols Family Applications After (2) Application Number Title Priority Date Filing Date GB29814/64A Expired GB1111336A (en) 1964-07-24 1964-07-24 Aryl ketones GB34309/66A Expired GB1111337A (en) 1964-07-24 1964-07-24 Substituted aralkyl alcohols Country Status (4) Cited By (5) * Cited by examiner, â Cited by third party Publication number Priority date Publication date Assignee Title US4732896A (en) * 1981-12-24 1988-03-22 Delalande S.A. Aromatic derivatives comprising an aminoalkoxy chain, the salts thereof, the process for preparing these derivatives and salts and the application thereof in therapeutics US4945099A (en) * 1987-01-12 1990-07-31 Eli Lilly And Company Anti-inflammatory agents US5098613A (en) * 1987-01-12 1992-03-24 Eli Lilly And Company Anti-inflammatory agents US5294613A (en) * 1987-01-12 1994-03-15 Eli Lilly And Company Method of treating endotoxic shock in mammals EP0600717A1 (en) * 1992-11-30 1994-06-08 Sankyo Company Limited Phenoxyalkylamines, -pyrrolidines and -piperidines for the treatment and prevention of circulatory diseases and psychosis Families Citing this family (6) * Cited by examiner, â Cited by third party Publication number Priority date Publication date Assignee Title FR2518992A1 (en) * 1981-12-24 1983-07-01 Delalande Sa 1-Amino-omega-aryloxy substd. ethane and propane derivs. - with calcium antagonising activity e.g. for treating angina FR2537970B1 (en) * 1982-12-15 1986-08-14 Delalande Sa NOVEL AMINOALKOXY AROMATIC DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR APPLICATION IN THERAPEUTICS CA1315279C (en) * 1987-01-12 1993-03-30 Nancy Grace Bollinger Anti-inflammatory agents DE3825559A1 (en) * 1988-07-28 1990-02-01 Basf Ag P-HYDROXIPHENONE DERIVATIVES AND THEIR USE CA2051501C (en) * 1990-09-20 2004-02-17 Robert J. Dinerstein 1-phenyl-3-phenyl-2-propyne-1-ones as calcium uptake inhibitors FR2670205A1 (en) * 1990-12-06 1992-06-12 Rhone Poulenc Agrochimie 2,6-ALKOXYPENYL ALKYLCETONE AND DERIVATIVES HERBICIDES.

1964
- 1964-07-24 GB GB34310/66A patent/GB1111338A/en not_active Expired
- 1964-07-24 GB GB29814/64A patent/GB1111336A/en not_active Expired
- 1964-07-24 GB GB34309/66A patent/GB1111337A/en not_active Expired
1965
- 1965-07-20 CH CH1016165A patent/CH441370A/en unknown
- 1965-07-22 DE DE19651493729 patent/DE1493729A1/en active Pending
- 1965-07-23 FR FR25801A patent/FR5003M/fr not_active Expired
- 1965-07-23 FR FR25802A patent/FR1499864A/en not_active Expired

Cited By (7) * Cited by examiner, â Cited by third party Publication number Priority date Publication date Assignee Title US4732896A (en) * 1981-12-24 1988-03-22 Delalande S.A. Aromatic derivatives comprising an aminoalkoxy chain, the salts thereof, the process for preparing these derivatives and salts and the application thereof in therapeutics US4945099A (en) * 1987-01-12 1990-07-31 Eli Lilly And Company Anti-inflammatory agents US5098613A (en) * 1987-01-12 1992-03-24 Eli Lilly And Company Anti-inflammatory agents US5294613A (en) * 1987-01-12 1994-03-15 Eli Lilly And Company Method of treating endotoxic shock in mammals EP0600717A1 (en) * 1992-11-30 1994-06-08 Sankyo Company Limited Phenoxyalkylamines, -pyrrolidines and -piperidines for the treatment and prevention of circulatory diseases and psychosis AU666590B2 (en) * 1992-11-30 1996-02-15 Sankyo Company Limited Alpha, omega-diarylalkane derivatives, their preparation and their use in the treatment and prevention of circulatory diseases and psychosis US5556864A (en) * 1992-11-30 1996-09-17 Sankyo Company, Limited Î±-Ï-diarylalkane compounds serotonin-2 receptor agonists Also Published As Similar Documents Publication Publication Date Title GB1111338A (en) 1968-04-24 Aralkyl substituted resorcinols GB961037A (en) 1964-06-17 Pyrazolones and processes for their preparation GB1111989A (en) 1968-05-01 2',3'-dideoxyriboside-2',3'-olefins GB1069797A (en) 1967-05-24 ÂªÂ-aminoketone derivatives ES320729A1 (en) 1966-05-16 Procedure for the synthesis of new derivatives of antranilic acid. (Machine-translation by Google Translate, not legally binding) ES389473A1 (en) 1974-12-16 Derivatives of 3-aminocarbonyl-2-oxazolidinone and their process of preparation GB1070139A (en) 1967-05-24 Novel imidazothiazole derivatives and a process for preparation thereof GB1069342A (en) 1967-05-17 Derivatives of 5-aryloxyoxazolidines GB1121140A (en) 1968-07-24 Process for preparing 3-aminoisoxazole derivatives ES274329A1 (en) 1962-06-01 Procedure for the preparation of new compounds of 1,5-benzodioxepano (Machine-translation by Google Translate, not legally binding) ES385774A1 (en) 1973-11-16 Procedure for the preparation of new 2- (5-nitro-2- furil) -the (3,2-d) pyrimidines. (Machine-translation by Google Translate, not legally binding) GB1114694A (en) 1968-05-22 Diazaspiro[4,5]decan-1,3-dione derivatives GB1109502A (en) 1968-04-10 Substituted n-benzyl-ethylenediamines ES419739A1 (en) 1976-05-01 2-aryl-amino-imidazoline-2 compounds GB1082466A (en) 1967-09-06 2-benzamidophenylalkanoic acid derivatives and their preparation GB1044778A (en) 1966-10-05 Colour photography GB1104323A (en) 1968-02-21 3-phenylpyrrole derivatives and process for preparing the same GB1325944A (en) 1973-08-08 Bisoxalic acid diamides GB1085083A (en) 1967-09-27 Improvements in or relating to benzimidazoles and the manufacture thereof GB1058193A (en) 1967-02-08 -a-carboline derivatives GB1085997A (en) 1967-10-04 Manufacturing method of imidazolidinone derivatives ES321807A1 (en) 1966-06-16 Procedure for the synthesis of new derivatives of 1,2,3,6-tetrahidropiridina. (Machine-translation by Google Translate, not legally binding) ES364726A1 (en) 1970-12-16 Procedure for the preparation of new derivatives of paminoalquil-bencensulfonamida. (Machine-translation by Google Translate, not legally binding) ES364723A1 (en) 1970-12-16 Procedure for the preparation of new derivatives of paminoalquil-bencensulfonamida. (Machine-translation by Google Translate, not legally binding) GB842323A (en) 1960-07-27 Aminoguanidine derivatives

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