GB984119A - Substituted piperidines and methods for their preparation - Google Patents
Substituted piperidines and methods for their preparationInfo
- Publication number
- GB984119A GB984119A GB2224061A GB2224061A GB984119A GB 984119 A GB984119 A GB 984119A GB 2224061 A GB2224061 A GB 2224061A GB 2224061 A GB2224061 A GB 2224061A GB 984119 A GB984119 A GB 984119A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- general formula
- group
- compounds
- 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
Links
- 150000003053 piperidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000003638 chemical reducing agent Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 2
- -1 methylene dioxy Chemical group 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 2
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 2
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 abstract 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical class CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 abstract 1
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- 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
- C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
- C07D211/84—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 two 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 directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
-
- 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- 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
- C07D295/096—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0984119/C2/1> and their acid addition and quaternary ammonium salts, wherein R1 is hydrogen, methyl, ethyl or n-rpopyl; R2 is a straight or branched C2- 9 alkyl group; R1 and R2 may together form a ring provided by the group (CH2)4, (CH2)5 or (CH2)6; R3 is propyl; R4 and R5 and R6 are hydrogen, C1- 4 alkoxy or hydroxy or an ester thereof having 1-4 carbon atoms; R4 and R5 or R5 and R6 may together form a methylene dioxy or ethylene dioxy group; and n is an integer from 1 to 3, the preparation thereof by reacting an appropriate phenyl alkyl amine of the general formula <FORM:0984119/C2/2> either with an appropriate glutaric anhydride, acid, or ester thereof followed by reduction of the resulting glutarimide with lithium aluminium hydride or other such suitable reducing agent or with a substituted alkane of the formula <FORM:0984119/C2/3> wherein X represents halogen or hydroxyl or by reacting a piperidine of the formula <FORM:0984119/C2/4> with a phenyl alkyl halide of the formula <FORM:0984119/C2/5> or with a carboxylic acid of the general formula <FORM:0984119/C2/6> followed by reduction of the resulting glutarimide with lithium aluminium hydride or other suitable reducing agent; and pharmaceutical compositions containing the above compounds. Pharmaceutical compositions, having antihypertensive action, comprise the compounds of the invention and in association with a pharmaceutical carrier. The composition may be in the form of tablets, solutions for injection, encapsulated powders, or liquid compositions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU61676/60A AU248763B2 (en) | 1960-06-20 | Substituted piperidines and methods for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB984119A true GB984119A (en) | 1965-02-24 |
Family
ID=3746638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2224061A Expired GB984119A (en) | 1960-06-20 | 1961-06-20 | Substituted piperidines and methods for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB984119A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3965105A (en) * | 1975-01-20 | 1976-06-22 | Sterling Drug Inc. | Phenyl-lower-alkylamines |
| EP0007479A1 (en) * | 1978-07-08 | 1980-02-06 | BASF Aktiengesellschaft | N-Arylpropyl-substituted cyclic amines, fungicides containing these compounds, and process for the preparation thereof |
| US4593037A (en) * | 1984-07-26 | 1986-06-03 | Pfizer Inc. | 1,3-disubstituted piperidine compounds as neuroleptic agents |
| US4623728A (en) | 1984-07-26 | 1986-11-18 | Pfizer Inc. | Intermediates for 1,3-disubstituted piperidine compounds as neuroleptic agents |
| EP0339878A3 (en) * | 1988-04-25 | 1990-12-05 | Eli Lilly And Company | Propanamine derivatives |
| EP0529688A3 (en) * | 1988-08-31 | 1993-03-10 | Daiichi Pharmaceutical Co., Ltd. | Azaspiro n,m alkanes and diazaspiro n,m -alkanes |
| US5286723A (en) * | 1988-08-31 | 1994-02-15 | Daiichi Seiyaku Co., Ltd. | Spiro compound |
-
1961
- 1961-06-20 GB GB2224061A patent/GB984119A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3965105A (en) * | 1975-01-20 | 1976-06-22 | Sterling Drug Inc. | Phenyl-lower-alkylamines |
| EP0007479A1 (en) * | 1978-07-08 | 1980-02-06 | BASF Aktiengesellschaft | N-Arylpropyl-substituted cyclic amines, fungicides containing these compounds, and process for the preparation thereof |
| US4593037A (en) * | 1984-07-26 | 1986-06-03 | Pfizer Inc. | 1,3-disubstituted piperidine compounds as neuroleptic agents |
| US4623728A (en) | 1984-07-26 | 1986-11-18 | Pfizer Inc. | Intermediates for 1,3-disubstituted piperidine compounds as neuroleptic agents |
| EP0339878A3 (en) * | 1988-04-25 | 1990-12-05 | Eli Lilly And Company | Propanamine derivatives |
| EP0529688A3 (en) * | 1988-08-31 | 1993-03-10 | Daiichi Pharmaceutical Co., Ltd. | Azaspiro n,m alkanes and diazaspiro n,m -alkanes |
| US5286723A (en) * | 1988-08-31 | 1994-02-15 | Daiichi Seiyaku Co., Ltd. | Spiro compound |
| US5508428A (en) * | 1988-08-31 | 1996-04-16 | Daiichi Phamaceutical Co., Ltd. | Spiro compound |
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