GB2010270A - Novel "soft" anticholinergic agents exhibiting anti-secretory activity - Google Patents

Novel "soft" anticholinergic agents exhibiting anti-secretory activity

Info

Publication number
GB2010270A
GB2010270A GB7848850A GB7848850A GB2010270A GB 2010270 A GB2010270 A GB 2010270A GB 7848850 A GB7848850 A GB 7848850A GB 7848850 A GB7848850 A GB 7848850A GB 2010270 A GB2010270 A GB 2010270A
Authority
GB
United Kingdom
Prior art keywords
atoms
halogen
image
alkoxy
secretory activity
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.)
Granted
Application number
GB7848850A
Other versions
GB2010270B (en
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.)
Interx Research Corp
Original Assignee
Interx Research Corp
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 Interx Research Corp filed Critical Interx Research Corp
Publication of GB2010270A publication Critical patent/GB2010270A/en
Application granted granted Critical
Publication of GB2010270B publication Critical patent/GB2010270B/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C07D295/08—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 singly bound oxygen or sulfur atoms
    • C07D295/084—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/90—Benzo [c] furans; Hydrogenated benzo [c] furans with an oxygen atom in position 1 and a nitrogen atom in position 3, or vice versa
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Hydrogenated Pyridines (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Compounds of general formula I or II: <IMAGE> are disclosed, wherein <IMAGE> represents tertiary amine <IMAGE> an unsaturated amine and R2, R3 and R4 (which may be the same or different, but at least two of them must be other than H and together they must contain at least five C-atoms) each represents hydrogen, C1-C8 alkyl or alkoxy, cycloalkyl cycloalkenyl, alkoxyalkyl, acyloxyalkyl, haloalkyl or carboxyalkyl each having up to 8 C atoms, alkenylphenyl having unto 8 C-atoms in the alkenyl moiety, aryl (optionally substituted by halogen, C1-C4 alkoxy, acyloxy, nitro, carboxyl or carboethoxy), -CH2, -CH2OCOR1 (wherein R1 is as defined below or -CH2ONO2), -OH, halogen, -OCOR1 (wherein R1 is as defined below) or - ONO2; or R2 is as hereinbefore defined and R3, R4 and the carbon atoms to which they are attached form a cyclo-alkyl group having up to 8 carbon atoms, or the groups represented by R2, R3 and R4 and the carbon atom to which they are attached form a fused polycarbocylic ring or a polyheterocyclic ring; and R1 is as defined by R2, R3 or R4; X is -O- or -S- and Y is halogen or another anion. The compounds possess anticholinergic anti- secretory activity, while exhibiting low toxicity following therapeutic application.
GB7848850A 1977-12-16 1978-12-18 Soft anticholinergic agents exhibiting antisecretory activity Expired GB2010270B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US86121077A 1977-12-16 1977-12-16

Publications (2)

Publication Number Publication Date
GB2010270A true GB2010270A (en) 1979-06-27
GB2010270B GB2010270B (en) 1982-10-20

Family

ID=25335183

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7848850A Expired GB2010270B (en) 1977-12-16 1978-12-18 Soft anticholinergic agents exhibiting antisecretory activity

Country Status (15)

Country Link
JP (1) JPS5498711A (en)
AR (1) AR222478A1 (en)
AT (1) AT366380B (en)
AU (1) AU531835B2 (en)
CA (1) CA1102345A (en)
DE (1) DE2854308A1 (en)
DK (1) DK534178A (en)
ES (1) ES476048A1 (en)
FR (1) FR2422624A1 (en)
GB (1) GB2010270B (en)
IE (1) IE48012B1 (en)
IT (1) IT1101735B (en)
NL (1) NL7812257A (en)
NO (1) NO148776C (en)
SE (1) SE436027B (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0053307A1 (en) * 1980-11-29 1982-06-09 CELAMERCK GmbH &amp; Co. KG Imidazole and triazole pesticides
EP0112067A2 (en) * 1982-11-18 1984-06-27 Shionogi & Co., Ltd. Phthalidylammonium compounds and their production, and their use in the production of 1-phthalidyl-5-fluorouracil derivatives and formulations containing such derivatives
US4824676A (en) * 1984-10-11 1989-04-25 Schering Corporation Physiological means of enhancing transdermal delivery of drugs
US5008111A (en) * 1984-10-11 1991-04-16 Schering Corporation Physiological means of enhancing transdermal delivery of drugs
FR2703046A1 (en) * 1993-03-26 1994-09-30 Poudres & Explosifs Ste Nale Process for the preparation of alpha -monohalogenated haloglyoxalates and oxalates and new alpha -monohalogenated haloglyoxalates and oxalates
EP1674068A1 (en) 1996-02-19 2006-06-28 Acrux DDS Pty Ltd Dermal penetration enhancers and drug delivery systems involving same
WO2006128255A1 (en) 2005-06-03 2006-12-07 Acrux Dds Pty Ltd Method and composition for transdermal drug delivery
EP1968945A2 (en) * 2005-12-30 2008-09-17 Ranbaxy Laboratories Limited Muscarinic receptor antagonists
WO2009055860A1 (en) 2007-11-02 2009-05-07 Acrux Dds Pty Ltd Transdermal delivery system
WO2015021954A1 (en) 2013-08-13 2015-02-19 Epinamics Gmbh Aerosol dispenser for transdermally acting pharmaceutical compositions
CN110041264A (en) * 2019-04-11 2019-07-23 贺州学院 A kind of adamantyl glyoxaline ion liquid and preparation method thereof

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5962505A (en) * 1998-08-31 1999-10-05 Bobrove; Arthur M. Method for treating hot flashes in humans
US6433003B1 (en) 1999-04-23 2002-08-13 Arthur M. Bobrove Method for treating hyperhidrosis in mammals
AR044134A1 (en) * 2003-05-02 2005-08-24 Novartis Ag DERIVATIVES OF QUINUCLIDINE, PREPARATION METHOD AND PHARMACEUTICAL COMPOSITIONS.
EP2903614B1 (en) * 2012-10-05 2021-09-29 Sphaera Pharma Pte. Ltd Novel compounds, their synthesis and their uses

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL101555C (en) * 1955-03-19
BE798253A (en) * 1973-04-16 1973-10-16 Bekaert Sa Nv SEATING
US3998815A (en) * 1974-06-24 1976-12-21 Interx Research Corporation 1-hydrocarbonoyloxymethyl-3-carbamoyl or 3-carboethoxy-pyridinium salts

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0053307A1 (en) * 1980-11-29 1982-06-09 CELAMERCK GmbH &amp; Co. KG Imidazole and triazole pesticides
EP0112067A2 (en) * 1982-11-18 1984-06-27 Shionogi & Co., Ltd. Phthalidylammonium compounds and their production, and their use in the production of 1-phthalidyl-5-fluorouracil derivatives and formulations containing such derivatives
EP0112067A3 (en) * 1982-11-18 1985-08-14 Shionogi & Co., Ltd. Phthalidylammonium compounds and their production, and their use in the production of 1-phthalidyl-5-fluorouracil derivatives and formulations containing such derivatives
US4824676A (en) * 1984-10-11 1989-04-25 Schering Corporation Physiological means of enhancing transdermal delivery of drugs
US5008111A (en) * 1984-10-11 1991-04-16 Schering Corporation Physiological means of enhancing transdermal delivery of drugs
FR2703046A1 (en) * 1993-03-26 1994-09-30 Poudres & Explosifs Ste Nale Process for the preparation of alpha -monohalogenated haloglyoxalates and oxalates and new alpha -monohalogenated haloglyoxalates and oxalates
EP1674068A1 (en) 1996-02-19 2006-06-28 Acrux DDS Pty Ltd Dermal penetration enhancers and drug delivery systems involving same
WO2006128255A1 (en) 2005-06-03 2006-12-07 Acrux Dds Pty Ltd Method and composition for transdermal drug delivery
EP1968945A2 (en) * 2005-12-30 2008-09-17 Ranbaxy Laboratories Limited Muscarinic receptor antagonists
WO2009055860A1 (en) 2007-11-02 2009-05-07 Acrux Dds Pty Ltd Transdermal delivery system
WO2015021954A1 (en) 2013-08-13 2015-02-19 Epinamics Gmbh Aerosol dispenser for transdermally acting pharmaceutical compositions
DE102013013397A1 (en) 2013-08-13 2015-03-12 Epinamics Gmbh Aerosol dispenser for transdermal pharmaceutical compositions
CN110041264A (en) * 2019-04-11 2019-07-23 贺州学院 A kind of adamantyl glyoxaline ion liquid and preparation method thereof

Also Published As

Publication number Publication date
ATA901478A (en) 1981-08-15
SE436027B (en) 1984-11-05
AR222478A1 (en) 1981-05-29
DE2854308A1 (en) 1979-06-21
CA1102345A (en) 1981-06-02
NO148776C (en) 1983-12-14
IE48012B1 (en) 1984-09-05
SE7812911L (en) 1979-06-17
NO148776B (en) 1983-09-05
AU531835B2 (en) 1983-09-08
GB2010270B (en) 1982-10-20
NL7812257A (en) 1979-06-19
IT7830735A0 (en) 1978-12-12
AU4264678A (en) 1979-06-21
FR2422624B1 (en) 1983-10-14
AT366380B (en) 1982-04-13
ES476048A1 (en) 1979-11-01
IE782499L (en) 1979-06-16
IT1101735B (en) 1985-10-07
JPS5498711A (en) 1979-08-03
NO784229L (en) 1979-06-19
FR2422624A1 (en) 1979-11-09
DK534178A (en) 1979-06-17

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Legal Events

Date Code Title Description
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
PCNP Patent ceased through non-payment of renewal fee