GB1319040A - 2,2,-diaryl-4-4-aryl-4-hydroxy-piperidino butyramides - Google Patents

2,2,-diaryl-4-4-aryl-4-hydroxy-piperidino butyramides

Info

Publication number
GB1319040A
GB1319040A GB1683971A GB1683971A GB1319040A GB 1319040 A GB1319040 A GB 1319040A GB 1683971 A GB1683971 A GB 1683971A GB 1683971 A GB1683971 A GB 1683971A GB 1319040 A GB1319040 A GB 1319040A
Authority
GB
United Kingdom
Prior art keywords
methyl
chloro
fluorophenyl
hydroxy
bis
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
Application number
GB1683971A
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.)
Filing date
Publication date
Application filed by Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV
Publication of GB1319040A publication Critical patent/GB1319040A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/64—Acyl halides
    • C07C57/76—Acyl halides containing halogen outside the carbonyl halide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
    • C07C59/115—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups containing halogen
    • 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

Abstract

1319040 4 - (4 - Hydroxypiperidino)butyramides JANSSEN PHARMACEUTICA NV 25 May 1971 [1 June 1970 30 March 1971] 16839/71 Heading C2C The invention comprises novel 4-(4-hydroxypiperidino)butyramides of the Formulµ and therapeutically acceptable addition salts thereof wherein R is H or CH 3 , Ar 1 is phenyl or halophenyl, Ar 2 is phenyl or halophenyl, R 5 is H or CH 3 and -N=2 is 1-pyrrolidinyl, piperidino optionally substituted by CH 3 , morpholino, 2,6-di-(C 1-6 alkyl)morpholino, N(CH 2 CH = CH 2 ) 2 , -NR 3 R 4 in which R 3 is C 1-6 alkyl or benzyl and R 4 is C 1-6 alkyl; -N=Z 1 is NH 2 or -NH- (C 1-6 alkyl); -N=Z 2 is -N(C 1-6 alkyl) 2 ; and Ar 3 is phenyl or substituted phenyl; provided that when R 5 is CH 3 then -N = Z is other than N(CH 2 CH=CH 2 ) 2 ; and their preparation. The compounds are prepared by reacting the appropriate 4-(Ar 3 )-4-hydroxy-3R-piperidines with compounds of the formula or with compounds of the formula or with tetrahydrofuran derivatives of the formulµ wherein AN is a suitable anion, which are obtained by reacting compounds of the formula Ar 1 Ar 2 C.(COCl)CH 2 CH 2 Br with compounds of the formula HN=Z 1 or H-N=Z, or when R<SP>5</SP> is CH 3 , by reacting with the appropriate acids of the formula HAN. Other intermediates and starting materials are: 4 - bromo - 2,2 - diphenylbutyric acid, and the acid chloride thereof, 2,2-bis-(p-fluorophenyl)acetonitrile, 4 - bromo - 2,2 - bis-(pfluorophenyl)butyronitrile, 2,2 - bis - (p - fluorophenyl) - 4 - hydroxybutyric acid γ - lactone, 4 - bromo - 2,2 - bis - (p - fluorophenyl)butyric acid and the acid chloride thereof. 4-bromo-2- (p - fluorophenyl) - 2 - phenylbutyrylchloride, 4 - chloro - 2,2 - diphenylbutyramide, tetrahydro - 4 - methyl - 3,3 - diphenyl - 2 - furanimine hydrochloride, 2 - bromo - 2 - (p - fluorophenyl)acetonitrile, 3 - cyano - 2 - methyl- 3,3 - diphenylpropionic acid chloride, N-(tetrahydro - 3,3 - diphenyl - 2 - furylidene)methylamine, 4 - chloro - N - methyl - 2,2 - diphenylbutyramide, 4 - chloro - N - methyl - 2,2- bis - (p - fluorophenyl)butyramide, 4 - chloro- N - ethyl - 2,2 - diphenylbutyramide, 4- chloro- N - methyl - 2 - (p - fluorophenyl) - 2 - phenylbutyramide, 4 - chloro - 2,2 - bis - (p - fluorophenyl)butyramide, 4 - chloro - 2 - (p - fluorophenyl) - 2 - phenylbutyramide, N,N - dimethyl - 2,2 - diphenyl - 4 - pentenamide, 1 - (2,2 - diphenyl - 4 - pentenoyl)pyrrolidine, 4 - hydroxy - N, N - dimethyl - 2,2 - diphenylbutyramide, 4 - chloro - N,N - dimethyl - 2,2- diphenylbutyramide, methyl N,N - bis - [2- (methoxycarbonyl)ethyl]carbamate, dimethyl 4 - oxo - 1,3 - piperidinedicarboxylate, dimethyl- 3 - methyl - 4 - oxo - 1,3 - piperidinedicarboxylate, methyl - 3 - methyl - 4 - oxo - 1 - piperidinecarboxylate, 1 - ethoxy - carbonyl - 4 - (4- bromophenyl) - 4 - hydroxypiperidine, 1- ethoxycarbonyl - 4 - hydroxy - 4 - (3,4,5 - trimethylphenyl)piperidine, methyl 4 - (p - chlorophenyl) - 4 - hydroxy - 3 - methyl - 1 - piperidinecarboxylate, methyl 4 - (4 - chloro - 3 - trifluoromethylphenyl) - 4 - hydroxy - 3 - methylpiperinecarboxylate, 4 - (4 - bromophenyl) - 4- hydroxypiperidine, 4 - hydroxy - 4 - (3,4,5- trimethylphenyl)piperidine, α,dl - 4 - (p - chlorophenyl) - 3 - methyl - 4 - piperidinol, α-(+) - 4- (4 - chloro - 3 - trifluoromethylphenyl) - 3- methyl - 4 - piperidinol hydrochloride, 4- hydroxy - 4 - (3,5 - dimethylphenyl)piperidine, α - (+) - 3 - methyl - 4 - (p - tolyl) - 4 - piperidinol and α - (+) - 4 - (p - methoxyphenyl)- 3-methyl-4-piperidinol. Pharmaceutical compositions, suitable for oral or parenteral administration, contain the above novel compounds and pharmaceutically acceptable diluents or carriers. The compounds possess anti-diarrheal and analgesic activities.
GB1683971A 1970-06-01 1971-05-25 2,2,-diaryl-4-4-aryl-4-hydroxy-piperidino butyramides Expired GB1319040A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US4253070A 1970-06-01 1970-06-01
US12960771A 1971-03-30 1971-03-30

Publications (1)

Publication Number Publication Date
GB1319040A true GB1319040A (en) 1973-05-31

Family

ID=26719340

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1683971A Expired GB1319040A (en) 1970-06-01 1971-05-25 2,2,-diaryl-4-4-aryl-4-hydroxy-piperidino butyramides

Country Status (18)

Country Link
JP (1) JPS5754508B1 (en)
AT (1) AT312606B (en)
BE (1) BE767798A (en)
CH (2) CH549015A (en)
CS (1) CS171232B2 (en)
DE (2) DE2126559C3 (en)
DK (1) DK137382B (en)
ES (1) ES391633A1 (en)
FI (1) FI54472C (en)
FR (1) FR2100711B1 (en)
GB (1) GB1319040A (en)
HK (1) HK78076A (en)
HU (1) HU166420B (en)
IL (1) IL36949A (en)
NL (1) NL173848C (en)
NO (1) NO133547C (en)
PL (1) PL81548B1 (en)
SE (1) SE369418B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5585374A (en) * 1992-08-05 1996-12-17 John Wyeth Brother, Limited Amide derivatives
EP2266590A2 (en) 2002-02-22 2010-12-29 Shire LLC Active agent delivery sytems and methods for protecting and administering active agents
CN110357808A (en) * 2019-06-13 2019-10-22 上海上药新亚药业有限公司 A kind of crystallization processes of loperamide hydrochloride

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6190691B1 (en) 1994-04-12 2001-02-20 Adolor Corporation Methods for treating inflammatory conditions
US5962477A (en) 1994-04-12 1999-10-05 Adolor Corporation Screening methods for cytokine inhibitors
US5434158A (en) * 1994-04-26 1995-07-18 Merck & Co., Inc. Spiro-substituted azacycles as neurokinin-3 antagonists
GB9502644D0 (en) * 1995-02-10 1995-03-29 Zeneca Ltd Heterocyclic derivatives
US5849761A (en) 1995-09-12 1998-12-15 Regents Of The University Of California Peripherally active anti-hyperalgesic opiates
US6573282B1 (en) 1995-09-12 2003-06-03 Adolor Corporation Peripherally active anti-hyperalgesic opiates
WO1997024325A1 (en) * 1995-12-28 1997-07-10 Takeda Chemical Industries, Ltd. DIPHENYLMETHANE DERIVATIVES AS MIP-1α/RANTES RECEPTOR ANTAGONISTS

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5585374A (en) * 1992-08-05 1996-12-17 John Wyeth Brother, Limited Amide derivatives
EP2266590A2 (en) 2002-02-22 2010-12-29 Shire LLC Active agent delivery sytems and methods for protecting and administering active agents
EP2316468A1 (en) 2002-02-22 2011-05-04 Shire LLC Delivery system and methods for protecting and administering dextroamphetamine
EP2316469A1 (en) 2002-02-22 2011-05-04 Shire LLC Delivery system and methods for protecting and administering dextroamphetamine
CN110357808A (en) * 2019-06-13 2019-10-22 上海上药新亚药业有限公司 A kind of crystallization processes of loperamide hydrochloride

Also Published As

Publication number Publication date
DK137382B (en) 1978-02-27
JPS5754508B1 (en) 1982-11-18
IL36949A0 (en) 1971-07-28
NL7106829A (en) 1971-12-03
DK137382C (en) 1978-08-07
NO133547C (en) 1976-05-19
CS171232B2 (en) 1976-10-31
NO133547B (en) 1976-02-09
FI54472B (en) 1978-08-31
FI54472C (en) 1978-12-11
HK78076A (en) 1976-12-17
DE2126559A1 (en) 1972-10-05
PL81548B1 (en) 1975-08-30
DE2126559B2 (en) 1981-02-26
DE2126559C3 (en) 1982-01-14
FR2100711B1 (en) 1974-09-27
IL36949A (en) 1974-07-31
HU166420B (en) 1975-03-28
DE2167193C2 (en) 1983-05-19
AT312606B (en) 1974-01-10
NL173848C (en) 1984-03-16
BE767798A (en) 1971-11-29
FR2100711A1 (en) 1972-03-24
CH549015A (en) 1974-05-15
CH553182A (en) 1974-08-30
SE369418B (en) 1974-08-26
ES391633A1 (en) 1975-09-16

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
PE20 Patent expired after termination of 20 years
746B Proceeding under section 46(3) patents act 1977