GB1294733A

GB1294733A – 4-aryl-4-hydroxypiperidine derivatives and processes for the preparation thereof
– Google Patents

GB1294733A – 4-aryl-4-hydroxypiperidine derivatives and processes for the preparation thereof
– Google Patents
4-aryl-4-hydroxypiperidine derivatives and processes for the preparation thereof

Info

Publication number
GB1294733A

GB1294733A
GB39975/70A
GB3997570A
GB1294733A
GB 1294733 A
GB1294733 A
GB 1294733A
GB 39975/70 A
GB39975/70 A
GB 39975/70A
GB 3997570 A
GB3997570 A
GB 3997570A
GB 1294733 A
GB1294733 A
GB 1294733A
Authority
GB
United Kingdom
Prior art keywords
phenyl
general formula
methyl
oxo
prepared
Prior art date
1969-09-03
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
GB39975/70A
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.)

Janssen Pharmaceutica NV

Original Assignee
Janssen Pharmaceutica NV
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.)
1969-09-03
Filing date
1970-08-19
Publication date
1972-11-01

1970-08-19
Application filed by Janssen Pharmaceutica NV
filed
Critical
Janssen Pharmaceutica NV

1972-11-01
Publication of GB1294733A
publication
Critical
patent/GB1294733A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

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

C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member

C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member 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

C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C17/00—Preparation of halogenated hydrocarbons

C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction

C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups

C07C271/06—Esters of carbamic acids

C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms

C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms

C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings

C07D211/02—Preparation by ring-closure or hydrogenation

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

C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member

C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member 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

C07D211/74—Oxygen atoms

Abstract

1294733 4 – Phenyl – 1 – (4,4 – diphenylbutyl)- 4-hydroxy-piperidines JANSSEN PHARMACEUTICA NV 19 Aug 1970 [3 Sept 1969] 39975/70 Heading C2C Novel 4 – phenyl – 1 – (4,4 – diphenylbutyl). 4-hydroxy-piperidines of the general formula wherein R is a hydrogen atom or a methyl group, Ar 1 is a halophenyl group, Ar 2 is a phenyl or halophenyl group and Ar 3 is a phenyl, C 1-5 alkyl-phenyl, trifluoromethyl-phenyl, halophenyl, dihalophehyl, C 1-5 alkyl-halophenyl or trifluoromethyl-halophenyl group, and therapeutically acceptable acid addition salts thereof are prepared by heating a reactive ester of a 4,4- diphenyl-butan-1-ol of the general formula Ar 1 Ar 2 CH(CH 2 ) 3 OH with a 4-phenyl-4-hydroxypiperidine of the general formula followed optionally by salification of the product. 4-Phenyl-4-hydroxypiperidines of the third general formula above are prepared by condensing a 1-alkoxycarbonyl-4-oxo-piperidine of the general formula with a phenyl magnesium bromide of the general formula BrMgAr 3 under Grignard conditions and heating the resulting 1-alkoxycarbonyl-4-phenyl-4-hydroxypiperidine of the general formula with an alkali. Methyl 3-methyl-4-oxo-1-piperidine-carboxylate is prepared by reacting dimethyl 3,31-(benzyl-imino)-dipropionate and methyl chloroformate, cyclizing the resulting methyl N,N – bis – [2 – (methoxycarbonyl)ethyl] – carbamate in the presence of sodium methoxide, reacting the dimethyl 4-oxo-1,3-piperidinedicarboxylate so obtained with methyl iodide in the presence of sodium hydride and heating the resulting dimethyl 3-methyl-4-oxo-1,3-piperidinedicarboxylate with aqueous oxalic acid. 4,4- Diphenyl-butan-1-yl chlorides of the general formula Ar 1 Ar 2 CH(CH 2 ) 3 Cl are prepared by hydrogenating a 4-chloro-1,1-diphenyl-1-butene of the general formula Ar 1 Ar 2 C = CH(CH 2 ) 2 Cl in the presence of palladium. Pharmaceutical compositions having central nervous system depressant activity comprise, as active ingredient, a 4-phenyl-1-(4,4-diphenylbutyl)-4-hydroxy-piperidine of the first general formula above or a therapeutically acceptable acid addition salt thereof, in admixture with a therapeutically acceptable carrier therefor.

GB39975/70A
1969-09-03
1970-08-19
4-aryl-4-hydroxypiperidine derivatives and processes for the preparation thereof

Expired

GB1294733A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US85501669A

1969-09-03
1969-09-03

Publications (1)

Publication Number
Publication Date

GB1294733A
true

GB1294733A
(en)

1972-11-01

Family
ID=25320131
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB39975/70A
Expired

GB1294733A
(en)

1969-09-03
1970-08-19
4-aryl-4-hydroxypiperidine derivatives and processes for the preparation thereof

Country Status (22)

Country
Link

US
(1)

US3575990A
(en)

JP
(1)

JPS4932543B1
(en)

AT
(1)

AT299201B
(en)

BE
(1)

BE755589A
(en)

BR
(1)

BR6915392D0
(en)

CH
(1)

CH520671A
(en)

CS
(1)

CS159779B2
(en)

DE
(1)

DE2040231C3
(en)

DK
(1)

DK127424B
(en)

ES
(1)

ES383006A1
(en)

FI
(1)

FI51176C
(en)

FR
(1)

FR2068536B1
(en)

GB
(1)

GB1294733A
(en)

IL
(1)

IL35211A
(en)

IT
(1)

IT1040516B
(en)

NL
(1)

NL172446C
(en)

NO
(1)

NO131173C
(en)

PL
(1)

PL71070B1
(en)

RO
(1)

RO57021A
(en)

SE
(1)

SE354066B
(en)

YU
(1)

YU34354B
(en)

ZA
(1)

ZA706024B
(en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4039676A
(en)

*

1975-06-23
1977-08-02
Ciba-Geigy Corporation
2-piperidinoalkyl-1,4-benzodioxans

US4129655A
(en)

*

1976-04-26
1978-12-12
Ciba-Geigy Corporation
Neuroleptic 2-piperidinoalkyl-1,4-benzodioxans

US4383999A
(en)

*

1981-05-26
1983-05-17
Smithkline Beckman Corporation
Inhibition of GABA uptake by N-substituted azaheterocyclic carboxylic acids and their esters

US4514414A
(en)

*

1982-10-25
1985-04-30
Smithkline Beckman Corporation
N-Substituted pyrrolidineacetic acids and their esters

IL90858A
(en)

*

1988-07-07
1994-08-26
Rhone Poulenc Sante
Derivatives of (AZA) naphthalensultam, their preparation and compositions containing them

DE102004036349A1
(en)

*

2004-07-27
2006-03-23
Grünenthal GmbH

Substituted 3-phenylpiperidine derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

GB931788A
(en)

*

1960-01-14
1963-07-17
Sandoz Ltd
Improvements in or relating to benzhydryl esters

0

BE
BE755589D
patent/BE755589A/en
not_active
IP Right Cessation

1969

1969-09-03
US
US855016A
patent/US3575990A/en
not_active
Expired – Lifetime

1969-12-19
BR
BR215392/69A
patent/BR6915392D0/en
unknown

1970

1970-08-13
DE
DE2040231A
patent/DE2040231C3/en
not_active
Expired

1970-08-18
NL
NLAANVRAGE7012199,A
patent/NL172446C/en
not_active
IP Right Cessation

1970-08-19
GB
GB39975/70A
patent/GB1294733A/en
not_active
Expired

1970-08-24
CS
CS5805A
patent/CS159779B2/cs
unknown

1970-08-24
ES
ES383006A
patent/ES383006A1/en
not_active
Expired

1970-08-27
FR
FR707031281A
patent/FR2068536B1/fr
not_active
Expired

1970-08-28
CH
CH1293670A
patent/CH520671A/en
not_active
IP Right Cessation

1970-08-31
AT
AT788670A
patent/AT299201B/en
not_active
IP Right Cessation

1970-09-01
YU
YU2188/70A
patent/YU34354B/en
unknown

1970-09-01
IT
IT53154/70A
patent/IT1040516B/en
active

1970-09-02
IL
IL35211A
patent/IL35211A/en
unknown

1970-09-02
NO
NO3360/70A
patent/NO131173C/no
unknown

1970-09-02
ZA
ZA706024A
patent/ZA706024B/en
unknown

1970-09-02
FI
FI702426A
patent/FI51176C/en
active

1970-09-02
SE
SE11923/70A
patent/SE354066B/xx
unknown

1970-09-02
RO
RO64358A
patent/RO57021A/ro
unknown

1970-09-02
PL
PL1970142947A
patent/PL71070B1/pl
unknown

1970-09-03
JP
JP45077475A
patent/JPS4932543B1/ja
active
Pending

1970-09-03
DK
DK452570AA
patent/DK127424B/en
not_active
IP Right Cessation

Also Published As

Publication number
Publication date

RO57021A
(en)

1974-12-11

NL7012199A
(en)

1971-03-05

AT299201B
(en)

1972-06-12

NO131173B
(en)

1975-01-06

FI51176C
(en)

1976-11-10

FI51176B
(en)

1976-08-02

NO131173C
(en)

1975-04-16

US3575990A
(en)

1971-04-20

YU218870A
(en)

1978-12-31

JPS4932543B1
(en)

1974-08-31

DE2040231C3
(en)

1979-04-12

FR2068536A1
(en)

1971-08-27

SE354066B
(en)

1973-02-26

ES383006A1
(en)

1973-07-01

DE2040231A1
(en)

1971-03-18

CS159779B2
(en)

1975-01-31

BE755589A
(en)

1971-03-02

IT1040516B
(en)

1979-12-20

NL172446C
(en)

1983-09-01

YU34354B
(en)

1979-07-10

DK127424B
(en)

1973-11-05

ZA706024B
(en)

1972-04-26

IL35211A0
(en)

1970-11-30

DE2040231B2
(en)

1978-08-10

FR2068536B1
(en)

1973-07-13

CH520671A
(en)

1972-03-31

IL35211A
(en)

1973-11-28

PL71070B1
(en)

1974-04-30

BR6915392D0
(en)

1973-01-16

NL172446B
(en)

1983-04-05

Similar Documents

Publication
Publication Date
Title

GB1299669A
(en)

1972-12-13

6,7-benzomorphans and their preparation

GB1294763A
(en)

1972-11-01

3-oxo-2,3-dihydro-1,4-benzoxazine derivatives

GB1294733A
(en)

1972-11-01

4-aryl-4-hydroxypiperidine derivatives and processes for the preparation thereof

ES454063A1
(en)

1978-03-01

Novel benzylalcohol derivatives and processes for preparing the same

IL42384A
(en)

1976-12-31

N-benzhydryl-n'-p-hydroxybenzyl-piperazines and processes for their manufacture and pharmaceutical compositions containing them

GB997637A
(en)

1965-07-07

Substituted 2-cyclopropylmethyl-6,7-benzmorphans

GB1325354A
(en)

1973-08-01

Imidazolidinone derivatives process for their production and preparations containing same

GB1351526A
(en)

1974-05-01

Tropan-3-ol derivatives and processes for their preparation

GB1220599A
(en)

1971-01-27

New furazan derivatives, processes for their production and compositions containing them

GB1221407A
(en)

1971-02-03

0,2,3,4-tetrahydro-7-substituted-6-sulfamyl-4-quinazolinones, process for preparing the same and pharmaceutical compositions comprising the same

YU65092A
(en)

1994-11-15

PROCESS FOR THE PRODUCTION OF SUCCINYLCHOLINE HALOGENIDES

GB1047267A
(en)

US3052685A
(en)

1962-09-04

Diphenyl 4-piperidyl carbinol andits acid-addition salts

GB1467761A
(en)

1977-03-23

Phenoxypropylamine derivatives and preparation thereof

GB1218793A
(en)

1971-01-13

New butoxydimethylbenzamides and a process for their preparation

GB1310606A
(en)

1973-03-21

Adamantylcarboxamidophenylacetic acid derivatives their preparation and compositions containing them

GB1187501A
(en)

1970-04-08

Novel Bis-(p-Chloro-Phenoxy)-Acetic Acid Esters, the Preparation thereof and Compositions Containing them

GB1377610A
(en)

1974-12-18

5-piperidine-4-spiro- oxazolidinones method for their preparation and applications thereof

GB1440380A
(en)

1976-06-23

Pyrrolidine derivatives

GB1141266A
(en)

1969-01-29

Novel n-[substituted-3-pyrrolidinyl]-phthalimides and process for the preparation thereof

GB1202110A
(en)

1970-08-12

Novel quinoline derivatives and their preparation

GB1199040A
(en)

1970-07-15

Diisoeugenol Derivatives

GB1270120A
(en)

1972-04-12

Pyrimidine carboxylic acid ester derivatives

GB1164496A
(en)

1969-09-17

0-Oxaphenanthridine Derivatives and Method for the Preparation

ES350475A1
(en)

1969-05-01

Benzoic acid esters of 1-phenyl-1-benzyl-2-methyl-3-dimethylamino-propanol

Legal Events

Date
Code
Title
Description

1973-03-14
PS
Patent sealed [section 19, patents act 1949]

1990-09-19
PE20
Patent expired after termination of 20 years

Download PDF in English

None