GB2010270A - Novel "soft" anticholinergic agents exhibiting anti-secretory activity - Google Patents
Novel "soft" anticholinergic agents exhibiting anti-secretory activityInfo
- 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
Links
- 230000001262 anti-secretory effect Effects 0.000 title abstract 2
- 230000001747 exhibiting effect Effects 0.000 title abstract 2
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 title 1
- 239000000812 cholinergic antagonist Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 229910004679 ONO2 Inorganic materials 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 230000001078 anti-cholinergic effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 231100000053 low toxicity Toxicity 0.000 abstract 1
- -1 nitro, carboxyl Chemical group 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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.
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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053307A1 (en) * | 1980-11-29 | 1982-06-09 | CELAMERCK GmbH & Co. KG | Imidazole and triazole pesticides |
| 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 |
| 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)
| 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. |
| WO2014054058A2 (en) * | 2012-10-05 | 2014-04-10 | Sphaera Pharma Pvt. Ltd. | Novel compounds, their synthesis and their uses |
Family Cites Families (3)
| 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 |
-
1978
- 1978-11-29 DK DK534178A patent/DK534178A/en not_active Application Discontinuation
- 1978-12-12 IT IT30735/78A patent/IT1101735B/en active
- 1978-12-15 NO NO784229A patent/NO148776C/en unknown
- 1978-12-15 AR AR274836A patent/AR222478A1/en active
- 1978-12-15 JP JP15601378A patent/JPS5498711A/en active Pending
- 1978-12-15 ES ES476048A patent/ES476048A1/en not_active Expired
- 1978-12-15 SE SE7812911A patent/SE436027B/en unknown
- 1978-12-15 DE DE19782854308 patent/DE2854308A1/en not_active Withdrawn
- 1978-12-18 IE IE2499/78A patent/IE48012B1/en unknown
- 1978-12-18 GB GB7848850A patent/GB2010270B/en not_active Expired
- 1978-12-18 CA CA318,112A patent/CA1102345A/en not_active Expired
- 1978-12-18 FR FR7835596A patent/FR2422624A1/en active Granted
- 1978-12-18 NL NL7812257A patent/NL7812257A/en not_active Application Discontinuation
- 1978-12-18 AU AU42646/78A patent/AU531835B2/en not_active Expired
- 1978-12-18 AT AT0901478A patent/AT366380B/en active
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053307A1 (en) * | 1980-11-29 | 1982-06-09 | CELAMERCK GmbH & Co. KG | Imidazole and triazole pesticides |
| 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 |
|---|---|
| ES476048A1 (en) | 1979-11-01 |
| FR2422624A1 (en) | 1979-11-09 |
| GB2010270B (en) | 1982-10-20 |
| JPS5498711A (en) | 1979-08-03 |
| NO148776B (en) | 1983-09-05 |
| NO784229L (en) | 1979-06-19 |
| NO148776C (en) | 1983-12-14 |
| AU531835B2 (en) | 1983-09-08 |
| AR222478A1 (en) | 1981-05-29 |
| AT366380B (en) | 1982-04-13 |
| IE782499L (en) | 1979-06-16 |
| FR2422624B1 (en) | 1983-10-14 |
| IT7830735A0 (en) | 1978-12-12 |
| ATA901478A (en) | 1981-08-15 |
| IT1101735B (en) | 1985-10-07 |
| DK534178A (en) | 1979-06-17 |
| SE436027B (en) | 1984-11-05 |
| SE7812911L (en) | 1979-06-17 |
| NL7812257A (en) | 1979-06-19 |
| IE48012B1 (en) | 1984-09-05 |
| CA1102345A (en) | 1981-06-02 |
| AU4264678A (en) | 1979-06-21 |
| DE2854308A1 (en) | 1979-06-21 |
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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 |