CA2242494A1 - Novel n-substituted 4-((4'-aminobenzoyl)-oxymethyl)-piperidines having gastric prokinetic properties - Google Patents
Novel n-substituted 4-((4'-aminobenzoyl)-oxymethyl)-piperidines having gastric prokinetic propertiesInfo
- Publication number
- CA2242494A1 CA2242494A1 CA002242494A CA2242494A CA2242494A1 CA 2242494 A1 CA2242494 A1 CA 2242494A1 CA 002242494 A CA002242494 A CA 002242494A CA 2242494 A CA2242494 A CA 2242494A CA 2242494 A1 CA2242494 A1 CA 2242494A1
- Authority
- CA
- Canada
- Prior art keywords
- 6alkyl
- hydrogen
- alk
- 6alkyloxy
- substituted
- 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
- 230000002496 gastric effect Effects 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract 9
- 239000001257 hydrogen Substances 0.000 abstract 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 5
- -1 C5-6cycloalkanone Chemical group 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 abstract 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 abstract 1
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 abstract 1
- 125000000815 N-oxide group Chemical group 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000006735 deficit Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 230000030136 gastric emptying Effects 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
This invention concerns the compounds of formula (I) the N-oxide forms, the pharmaceutically acceptable acid addition salts and the stereochemically isomeric forms thereof, wherein R1 is C1-6alkyloxy, C2-6alkenyloxy or C2-6alkynyloxy; R2 is hydrogen or C1-6alkyloxy, or when taken together R1 and R2 may form a bivalent radical of formula wherein in said bivalent radicals one or two hydrogen atoms may be substituted with C1-6alkyl, R3 is hydrogen or halo;
L is C3-6cycloalkyl, C5-6cycloalkanone, C2-6alkenyl optionally substituted with aryl, or L is a radical of formula -Alk-R4, -Alk-NR5R6, 1-R6-4-piperidinyl, Alk-X-R7, -Alk-Y-C(=O)-R9 or -Alk-Y-C(=O)-NR11R12, wherein each Alk is C1-12alkanediyl; R4 is hydrogen, C1-6alkylsulfonylamino, C3-6cycloalkyl, C3-6cycloalkanone, Ar-, di(Ar)methyl, Ar-oxy- or Het1; R5 is hydrogen or C1-6alkyl; R6 is Het2;
R7 is hydrogen, C1-6alkyl, hydroxyC1-6alkyl, C3-6cycloalkyl or Ar or Het2; X
is O, S, SO2 or NR8; said R8 being hydrogen, C1-6alkyl or Ar; R9 is hydrogen, C1-6alkyl, C3-6cycloalkyl, Ar, ArC1-6alkyl, di(Ar)methyl, C1-6alkyloxy or hydroxy; Y is NR10 or a direct bond; said R10 being hydrogen, C1-6alkyl or Ar; R11 and R12 each independently are hydrogen, C1-6alkyl, C3-6cycloalkyl, Ar or ArC1-6alkyl, or R11 and R12 combined with the nitrogen atom bearing R11 and R12 may form a pyrrolidinyl or piperidinyl ring both being optionally substituted with C1-6alkyl, amino or mono or di(C1-6alkyl)amino, or said R11 and R12 combined with the nitrogen bearing R11 and R12 may form a piperazinyl or 4-morpholinyl radical both being optionally substituted with C1-6alkyl. Processes for preparing said products, formulations comprising said products and their use as a medicine are disclosed, in particular for treating conditions which are related to impairment of gastric emptying.
L is C3-6cycloalkyl, C5-6cycloalkanone, C2-6alkenyl optionally substituted with aryl, or L is a radical of formula -Alk-R4, -Alk-NR5R6, 1-R6-4-piperidinyl, Alk-X-R7, -Alk-Y-C(=O)-R9 or -Alk-Y-C(=O)-NR11R12, wherein each Alk is C1-12alkanediyl; R4 is hydrogen, C1-6alkylsulfonylamino, C3-6cycloalkyl, C3-6cycloalkanone, Ar-, di(Ar)methyl, Ar-oxy- or Het1; R5 is hydrogen or C1-6alkyl; R6 is Het2;
R7 is hydrogen, C1-6alkyl, hydroxyC1-6alkyl, C3-6cycloalkyl or Ar or Het2; X
is O, S, SO2 or NR8; said R8 being hydrogen, C1-6alkyl or Ar; R9 is hydrogen, C1-6alkyl, C3-6cycloalkyl, Ar, ArC1-6alkyl, di(Ar)methyl, C1-6alkyloxy or hydroxy; Y is NR10 or a direct bond; said R10 being hydrogen, C1-6alkyl or Ar; R11 and R12 each independently are hydrogen, C1-6alkyl, C3-6cycloalkyl, Ar or ArC1-6alkyl, or R11 and R12 combined with the nitrogen atom bearing R11 and R12 may form a pyrrolidinyl or piperidinyl ring both being optionally substituted with C1-6alkyl, amino or mono or di(C1-6alkyl)amino, or said R11 and R12 combined with the nitrogen bearing R11 and R12 may form a piperazinyl or 4-morpholinyl radical both being optionally substituted with C1-6alkyl. Processes for preparing said products, formulations comprising said products and their use as a medicine are disclosed, in particular for treating conditions which are related to impairment of gastric emptying.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96200525 | 1996-02-29 | ||
| EP96200525.2 | 1996-02-29 | ||
| PCT/EP1997/000585 WO1997031897A1 (en) | 1996-02-29 | 1997-02-07 | Novel n-substituted 4-((4'-aminobenzoyl)-oxymethyl)-piperidines having gastric prokinetic properties |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2242494A1 true CA2242494A1 (en) | 1997-09-04 |
| CA2242494C CA2242494C (en) | 2006-05-23 |
Family
ID=36481478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002242494A Expired - Lifetime CA2242494C (en) | 1996-02-29 | 1997-02-07 | Novel n-substituted 4-((4'-aminobenzoyl)-oxymethyl)-piperidines having gastric prokinetic properties |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2242494C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7966111B2 (en) | 2009-10-15 | 2011-06-21 | Airbiquity, Inc. | Centralized management of motor vehicle software applications and services |
| US9730254B2 (en) | 2009-10-15 | 2017-08-08 | Airbiquity Inc. | Efficient headunit communication integration |
| US11004277B2 (en) | 2012-06-08 | 2021-05-11 | Airbiquity Inc. | Assessment of electronic sensor data to remotely identify a motor vehicle and monitor driver behavior |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110082127A (en) | 2008-10-28 | 2011-07-18 | 에어비퀴티 인코포레이티드. | Purchase of a piece of music being played on a radio in a vehicle |
| US8942888B2 (en) | 2009-10-15 | 2015-01-27 | Airbiquity Inc. | Extensible scheme for operating vehicle head unit as extended interface for mobile device |
| US8831823B2 (en) | 2009-10-15 | 2014-09-09 | Airbiquity Inc. | Centralized management of motor vehicle software applications and services |
| US9002574B2 (en) | 2009-10-15 | 2015-04-07 | Airbiquity Inc. | Mobile integration platform (MIP) integrated handset application proxy (HAP) |
-
1997
- 1997-02-07 CA CA002242494A patent/CA2242494C/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7966111B2 (en) | 2009-10-15 | 2011-06-21 | Airbiquity, Inc. | Centralized management of motor vehicle software applications and services |
| US8050817B2 (en) | 2009-10-15 | 2011-11-01 | Airbiquity Inc. | Centralized management of motor vehicle software applications and services |
| US9730254B2 (en) | 2009-10-15 | 2017-08-08 | Airbiquity Inc. | Efficient headunit communication integration |
| US10159098B2 (en) | 2009-10-15 | 2018-12-18 | Airbiquity Inc. | Efficient headunit communication integration |
| US11004277B2 (en) | 2012-06-08 | 2021-05-11 | Airbiquity Inc. | Assessment of electronic sensor data to remotely identify a motor vehicle and monitor driver behavior |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2242494C (en) | 2006-05-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20170207 |