GB1410783A - N-substituted 4-amidopyridines tetrahydropyridines and piperidines - Google Patents

N-substituted 4-amidopyridines tetrahydropyridines and piperidines

Info

Publication number
GB1410783A
GB1410783A GB272172A GB272172A GB1410783A GB 1410783 A GB1410783 A GB 1410783A GB 272172 A GB272172 A GB 272172A GB 272172 A GB272172 A GB 272172A GB 1410783 A GB1410783 A GB 1410783A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
radical
alkylene
reacting
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
GB272172A
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.)
John Wyeth and Brother Ltd
Original Assignee
John Wyeth and Brother 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.)
Filing date
Publication date
Application filed by John Wyeth and Brother Ltd filed Critical John Wyeth and Brother Ltd
Priority to GB272172A priority Critical patent/GB1410783A/en
Publication of GB1410783A publication Critical patent/GB1410783A/en
Expired legal-status Critical Current

Links

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
    • C07D211/36—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1410783 Substituted 4-amidopiperidines JOHN WYETH & BRO Ltd 22 Jan 1973 [20 Jan 1972] 2721/72 Heading C2C The invention comprises novel compounds having the general Formula I in which II represents a ring system of the Formula IIa, IIb or IIc A represents a direct bond, a C 1 -C 6 alkylene radical, a mono- or di-keto C 1 -C 6 alkylene radical, a hydroxy-C 1 -C 6 alkylene radical, a radical -OCH 2 CH(OH)CH 2 - or -O-(C 1 -C 6 alkylene)-; W represents one of the following radicals-1, 2, 3, 4-tetrahydronaphthyl, naphthyl, indenyl, indolyl, benzo-[b]-thienyl, piperidyl, pyrimidinyl, quinolyl, benzo-1,4-dioxanyl, and benzindolyl any of which may be substituted, and when A is or -O-(lower alkylene)-, W may also represent phenyl and when A is other than lower alkylene W may be a C 5 -C 7 cycloalkyl radical or a pyridyl radical; R represents an optionally substituted aryl C 1 -C 6 alkyl group, C 5 -C 7 cycloalkyl group or a C 1 -C 6 alkyl group; R<SP>1</SP> represents hydrogen or C 1 -C 6 alkyl; R<SP>2</SP> represents an optionally substituted aryl group and X- denotes an ion and the acid addition and quaternary ammonium salts of those compounds having ring systems IIb or IIc. The compounds of the invention may be prepared by (a) when the compounds have ring system II(a) or II(b), acylating a compound of Formula V in which the ring system has Formula Va or Vc with a reactive derivative of an acid of general Formula RCO 2 H, or with an acid of said formula in the presence of a known condensing agent, e.g. a carbodiimide, or with said acid after first activating the amino function, e.g. as phosphazo derivative; (b) reacting a compound of general Formula VIa, VIb or VIc with an agent of formula W-A-Y in which W and A are as defined above and Y is a halogen atom or similar replaceable group or atom, e.g. a tosyl group, or with a compound of formula W-A<SP>1</SP>-H wherein A<SP>1</SP> represents an epoxy substituted lower alkenyl radical or a radical of Formula IX when the product has chain A is an hydroxy lower alkylene or radical or with a compound of formula W-B wherein B is a straight or branched chain alkenyl radical, preferably a vinyl radical, to give a compound of Formula I in which A is a straight or branched chain alkylene radical, (d) a Mannich reaction between an aldehyde, a compound of Formula VIb-VIc and a compound of formula W-H or a derivative thereof in which chain A has been at least partially formed and contains a site of the type known to participate in the Mannich reaction; (e) reacting a compound of Formula XIIa or XIIb wherein T is a known precursor of W with another molecule known for the formation of W ; (f) reacting a compound of formula W-A-OH in which A is C 1 -C 6 alkylene with a compound of Formula VIb or VIc in the presence of a catalyst, e.g. Raney nickel; (g) reacting a compound of formula W-H with an acidhalide of Formula XVII to obtain a compound of Formula I in which A is (h) by treating a compound of Formula III under mild conditions so as to remove the group R<SP>4</SP>, hydrogenolysis may be used in which case other reducible functions may also be reduced during the reaction; (i) Fischer indole synthesis on a compound of Formula XIX to produce a product of Formula I in which W is an optionally substituted indole; (j) reacting a compound of formula W-H wherein W is an unsubstituted piperidyl radical and the H is attached to the nitrogen atom thereof with a compound Hal-A-Hal where A is C 1 -C 6 alkylene and Hal is halogen and a compound of Formula VIa-VIc to produce a compound of Formula I in which W is a piperidyl radical. Methods are disclosed for the synthesis of the intermediates referred to above without examples being provided. Pharmaceutical compositions having analgesic, anti-oxotremorine, hypotensive, anti-inflammatory, central nervous system or blood platelet aggregation inhibition activity for oral, intramuscular, intraperitoneal or subcutaneous administration comprise a compound of Formula I together with a pharmaceutically acceptable carrier.
GB272172A 1972-01-20 1972-01-20 N-substituted 4-amidopyridines tetrahydropyridines and piperidines Expired GB1410783A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB272172A GB1410783A (en) 1972-01-20 1972-01-20 N-substituted 4-amidopyridines tetrahydropyridines and piperidines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB272172A GB1410783A (en) 1972-01-20 1972-01-20 N-substituted 4-amidopyridines tetrahydropyridines and piperidines

Publications (1)

Publication Number Publication Date
GB1410783A true GB1410783A (en) 1975-10-22

Family

ID=9744635

Family Applications (1)

Application Number Title Priority Date Filing Date
GB272172A Expired GB1410783A (en) 1972-01-20 1972-01-20 N-substituted 4-amidopyridines tetrahydropyridines and piperidines

Country Status (1)

Country Link
GB (1) GB1410783A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0013894A1 (en) * 1979-01-15 1980-08-06 Roche Diagnostics GmbH Arylethers, process for their preparation and medicines containing them
US4361562A (en) 1979-08-10 1982-11-30 Sandoz Ltd. 3-Aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them
US4460586A (en) * 1981-01-16 1984-07-17 Sandoz Ltd. 2-Cyano-4-(2-hydroxy-3-substituted-aminopropoxy) indoles
EP0396282A2 (en) * 1989-04-20 1990-11-07 Boc, Inc. N-aryl-N-[4-(heterocyclicalkyl) piperidinyl]amides and pharmaceutical compositions and methods employing such compounds
US5001135A (en) * 1989-02-10 1991-03-19 Glaxo Group Limited Indole derivatives
USRE34201E (en) * 1989-04-20 1993-03-23 Anaquest, Inc. N-aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides and pharmaceutical compositions and methods employing such compounds
WO1993025528A1 (en) * 1992-06-08 1993-12-23 Richter Gedeon Vegyészeti Gyár Rt. Novel aminopropanol derivatives, pharmaceutical compositions containing them and process for preparing same
JP2014514362A (en) * 2011-05-12 2014-06-19 プロテオステイシス セラピューティクス，インコーポレイテッド Proteostasis regulator
US9850262B2 (en) 2013-11-12 2017-12-26 Proteostasis Therapeutics, Inc. Proteasome activity enhancing compounds

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0013894A1 (en) * 1979-01-15 1980-08-06 Roche Diagnostics GmbH Arylethers, process for their preparation and medicines containing them
US4361562A (en) 1979-08-10 1982-11-30 Sandoz Ltd. 3-Aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them
US4460586A (en) * 1981-01-16 1984-07-17 Sandoz Ltd. 2-Cyano-4-(2-hydroxy-3-substituted-aminopropoxy) indoles
US5001135A (en) * 1989-02-10 1991-03-19 Glaxo Group Limited Indole derivatives
USRE34201E (en) * 1989-04-20 1993-03-23 Anaquest, Inc. N-aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides and pharmaceutical compositions and methods employing such compounds
EP0396282A3 (en) * 1989-04-20 1992-01-08 Boc, Inc. N-aryl-N-[4-(heterocyclicalkyl) piperidinyl]amides and pharmaceutical compositions and methods employing such compounds
EP0396282A2 (en) * 1989-04-20 1990-11-07 Boc, Inc. N-aryl-N-[4-(heterocyclicalkyl) piperidinyl]amides and pharmaceutical compositions and methods employing such compounds
WO1993025528A1 (en) * 1992-06-08 1993-12-23 Richter Gedeon Vegyészeti Gyár Rt. Novel aminopropanol derivatives, pharmaceutical compositions containing them and process for preparing same
JP2014514362A (en) * 2011-05-12 2014-06-19 プロテオステイシス セラピューティクス，インコーポレイテッド Proteostasis regulator
US9556166B2 (en) 2011-05-12 2017-01-31 Proteostasis Therapeutics, Inc. Proteostasis regulators
US10532996B2 (en) 2011-05-12 2020-01-14 Proteostasis Therapeutics, Inc. Proteostasis regulators
US12180189B2 (en) 2011-05-12 2024-12-31 Kineta, Inc. Proteostasis regulators
US9850262B2 (en) 2013-11-12 2017-12-26 Proteostasis Therapeutics, Inc. Proteasome activity enhancing compounds
US11242361B2 (en) 2013-11-12 2022-02-08 Proteostasis Therapeutics, Inc. Proteasome activity enhancing compounds
US11958873B2 (en) 2013-11-12 2024-04-16 Kineta, Inc. Proteasome activity enhancing compounds

Similar Documents

Publication Publication Date Title
JPH0764815B2 (en) Compounds used in pharmaceutical compositions
GB1218570A (en) Indoles
GB1410783A (en) N-substituted 4-amidopyridines tetrahydropyridines and piperidines
GB1189064A (en) Indole Derivatives
KR100747425B1 (en) Substituted N-benzyl-indol-3-yl glyoxylic acid derivatives with antitumor effect
US2824875A (en) Certificate of correction
HU9400869D0 (en) New indol derivatives pharmaceutical compositions containing them, and process for producing them
US3655674A (en) 3-(2-(4-cyclohexanecarboxamido-1-piperidyl)ethyl)indole
AU4294900A (en) Use of cell membrane penetrating indigoid bisindole derivatives
GB1374414A (en) 1-acyl-3-amino-alkyl-indoles and their preparation
PT100801A (en) PROCESS FOR THE PREPARATION OF UTILITY SYNTHETIC ARIL-POLYAMINS AS ANTAGONISTS OF NEUROTRANSMITTERS AMINOACIDES AND COMPOUNDS OBTAINED
KR960703135A (en) New compound and its preparation
KR930016423A (en) Heterocyclic derivatives
US3518274A (en) Phenyl substituted n-(2-aminoethyl)-n-benzylamides
GB1481813A (en) Substituted thiazolinylidenyl ketones and their pharmaceutical compositions
GB1301243A (en)
KR940701407A (en) Hydroxyazido Derivatives and Related Compounds as Renin Inhibitors
PT87734B (en) METHOD FOR PREPARING NEW TRIPEPTIDES WITH VACUUM POLYCYCLIC STRUCTURE AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM
Coxworth Alkaloids of the Calabar bean
JPH0572903B2 (en)
US3903093A (en) 2-({62 -Alkyl thioethyl)-6,7-benzomorphans
US3906099A (en) 1,2,3,4-Tetra hydro-3-aminomethylisoquinolines in the treatment of mental depression
US3682926A (en) Tetrahydroiso quinolinecarboxamides
GB1393979A (en) Piperidine derivatives
GB1501475A (en) Piperidinobutyrophenone derivatives

Legal Events

Date Code Title Description
PS Patent sealed
746 Register noted 'licences of right' (sect. 46/1977)
PCNP Patent ceased through non-payment of renewal fee