GB1392677A

GB1392677A – 1,3-disubstituted 3-aroylpropanes and process for the preparation thereof
– Google Patents

GB1392677A – 1,3-disubstituted 3-aroylpropanes and process for the preparation thereof
– Google Patents
1,3-disubstituted 3-aroylpropanes and process for the preparation thereof

Info

Publication number
GB1392677A

GB1392677A
GB1912473A
GB1912473A
GB1392677A
GB 1392677 A
GB1392677 A
GB 1392677A
GB 1912473 A
GB1912473 A
GB 1912473A
GB 1912473 A
GB1912473 A
GB 1912473A
GB 1392677 A
GB1392677 A
GB 1392677A
Authority
GB
United Kingdom
Prior art keywords
formula
reacting
compound
hnr
amine
Prior art date
1972-04-22
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
GB1912473A
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.)

Istituto Luso Farmaco dItalia SpA

Original Assignee
Istituto Luso Farmaco dItalia SpA
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.)
1972-04-22
Filing date
1973-04-19
Publication date
1975-04-30

1973-04-19
Application filed by Istituto Luso Farmaco dItalia SpA
filed
Critical
Istituto Luso Farmaco dItalia SpA

1975-04-30
Publication of GB1392677A
publication
Critical
patent/GB1392677A/en

Status
Expired
legal-status
Critical
Current

Links

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Global Dossier

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Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms

C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms

C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms

C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings

C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C255/00—Carboxylic acid nitriles

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

C07C45/70—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 with functional groups containing oxygen only in singly bound form

C07C45/71—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 with functional groups containing oxygen only in singly bound form being hydroxy groups

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

C07D211/40—Oxygen atoms

C07D211/44—Oxygen atoms attached in position 4

C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4

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

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom

C07D303/02—Compounds containing oxirane rings

C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals

Abstract

1392677 1,3-Disubstituted-3-aroyl-propanes ISTITUTO LUSO FARMACO D’ITALIA SrL 19 April 1973 [22 April 1972 20 March 1973] 19124/73 Heading C2C The invention comprises compounds having the general formula (and pharmaceutically acceptable salts thereof) in both racemic and optically active forms in which Ar represents an aryl residue optionally substituted by halogen, polyhalo alkyl, or alkoxy; R1 is hydroxy, acyloxy, carbamoyloxy, alkylcarbamoyloxy, dialkylcarbamoyloxy, aroyloxy, alkoxy, aryloxy, cyano, -NB4R5 which is the residue of a secondary, tertiary or heterocyclic amine in which the N-atom and R4 and R5 form part of the ring; and is the residue of a secondary, tertiary or heterocyclic amine in which the N-atom and R2 and R3 form part of the ring. In the case where R1 = OH the compounds of the invention may be prepared by reacting a compound where X and Y represent halogen atoms with an alcoholate of an alkali metal or alkaline earth metal and reacting the resulting intermediate of the formula where ale is the residue of the alcoholate with an amine of the formula HNR2R3. When R1 is aryloxy, acyloxy or aroyloxy they may be prepared by reacting, a compound of Formula II with a metal salt of a phenol or of an aliphatic or aromatic carboxylic acid and reacting the intermediate of the formula with an amine of formula HNR2R3 or, when R1 is acyloxy or aryloxy, by reacting a compound of the formula with an aromatic or aliphatic carboxylic acid. When R1 is -NR2R3 the compounds of the invention may be prepared by reacting a compound of the Formula II with an excess of amine of formula HNR2R3 and R1 is -NR4R5 by reacting Formula II first with HNR4R5 and then with HNR2R3. Further preparations comprise brominating a compound of the formula and reacting the resulting intermediate of formula with a metallic salt of an alcohol, phenol or acid, with an amine HNR4R5 or with a metal cyanide; and when R1 is CN, by reacting a compound of the formula with a chloroamine of the formula The compounds of the invention exhibit analgesic and antiarrhythmic properties and are depressants of the central nervous system. They may be administered orally or by injection in admixture with a diluent or carriers.

GB1912473A
1972-04-22
1973-04-19
1,3-disubstituted 3-aroylpropanes and process for the preparation thereof

Expired

GB1392677A
(en)

Applications Claiming Priority (2)

Application Number
Priority Date
Filing Date
Title

IT2344472

1972-04-22

IT2188173

1973-03-20

Publications (1)

Publication Number
Publication Date

GB1392677A
true

GB1392677A
(en)

1975-04-30

Family
ID=26328026
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB1912473A
Expired

GB1392677A
(en)

1972-04-22
1973-04-19
1,3-disubstituted 3-aroylpropanes and process for the preparation thereof

Country Status (8)

Country
Link

US
(1)

US3951978A
(en)

JP
(1)

JPS4920140A
(en)

CA
(1)

CA977751A
(en)

DE
(1)

DE2320355A1
(en)

ES
(1)

ES413951A1
(en)

FR
(1)

FR2182995B1
(en)

GB
(1)

GB1392677A
(en)

NL
(1)

NL7305645A
(en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4126688A
(en)

*

1976-05-17
1978-11-21
Janssen Pharmaceutica N.V.
Antiemetic 1-(benzotriazolyl-alkyl)-piperidine derivatives

US4170653A
(en)

*

1976-05-19
1979-10-09
Ayerst McKenna and Harrison Limited
Antidepressant naphthyloxy piperidino and pyrrolidino propanol ethers

US4071552A
(en)

*

1976-05-19
1978-01-31
Ayerst Mckenna And Harrison Ltd.
Aryloxy aminobutanols, their preparation and use thereof

US4347382A
(en)

*

1980-04-15
1982-08-31
Burroughs Wellcome Co.
3H Labeled compounds

US4355179A
(en)

*

1980-04-14
1982-10-19
Burroughs Wellcome Co.
Radioactive nuclide labeled propiophenone compounds

US5236922A
(en)

*

1984-08-20
1993-08-17
Laboratoire L. Lafon
Method for treating depression using 1-(aminophenyl)-2-aminopropanone derivatives

CN1008735B
(en)

1984-11-02
1990-07-11
拜尔公司
Pyrrole ylmethyl-cyclopropyl-carbinol derivatives with replacement is a composition of active components

US4760146A
(en)

*

1986-02-18
1988-07-26
Pennwalt Corporation
Cyclohexene carboxylic esters and amides as antidysrhythmic agents

US5475138A
(en)

*

1994-07-07
1995-12-12
Pharm-Eco Laboratories Incorporated
Method preparing amino acid-derived diaminopropanols

AU2007254179B2
(en)

*

2006-05-18
2013-03-21
Pharmacyclics Llc
Intracellular kinase inhibitors

CN108691007B
(en)

*

2018-06-07
2020-11-03
南京大学
Method for producing metal single crystal particle

Family Cites Families (5)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US2997472A
(en)

*

1961-08-22

Certificate of correction

US2655542A
(en)

*

1952-04-17
1953-10-13
Upjohn Co
Aminoketones

NL127061C
(en)

*

1959-03-26

US3210368A
(en)

*

1964-09-29
1965-10-05
Ciba Geigy Corp
Certain 2-amino-4-aryl-5-n, n-disubstituted amino-lower alkyl-thiazole compounds

GB1171251A
(en)

*

1967-07-05
1969-11-19
British Drug Houses Ltd
Preparation of Piperazine Derivatives

1973

1973-04-18
US
US05/352,346
patent/US3951978A/en
not_active
Expired – Lifetime

1973-04-19
GB
GB1912473A
patent/GB1392677A/en
not_active
Expired

1973-04-19
NL
NL7305645A
patent/NL7305645A/xx
unknown

1973-04-20
FR
FR7314627A
patent/FR2182995B1/fr
not_active
Expired

1973-04-21
ES
ES413951A
patent/ES413951A1/en
not_active
Expired

1973-04-21
DE
DE2320355A
patent/DE2320355A1/en
active
Pending

1973-04-23
JP
JP48045197A
patent/JPS4920140A/ja
active
Pending

1973-04-24
CA
CA169,373A
patent/CA977751A/en
not_active
Expired

Also Published As

Publication number
Publication date

JPS4920140A
(en)

1974-02-22

FR2182995A1
(en)

1973-12-14

FR2182995B1
(en)

1976-12-03

AU5474273A
(en)

1974-10-24

DE2320355A1
(en)

1973-11-15

US3951978A
(en)

1976-04-20

CA977751A
(en)

1975-11-11

NL7305645A
(en)

1973-10-24

ES413951A1
(en)

1976-05-16

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Legal Events

Date
Code
Title
Description

1975-09-10
PS
Patent sealed [section 19, patents act 1949]

1978-11-22
PCNP
Patent ceased through non-payment of renewal fee

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