ES342933A1 - New piperidine derivatives the preparation and compositions containing same - Google Patents
New piperidine derivatives the preparation and compositions containing sameInfo
- Publication number
- ES342933A1 ES342933A1 ES342933A ES342933A ES342933A1 ES 342933 A1 ES342933 A1 ES 342933A1 ES 342933 A ES342933 A ES 342933A ES 342933 A ES342933 A ES 342933A ES 342933 A1 ES342933 A1 ES 342933A1
- Authority
- ES
- Spain
- Prior art keywords
- substituted
- prop
- acid
- ester
- ynyl
- 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
- 239000000203 mixture Substances 0.000 title abstract 2
- 150000003053 piperidines Chemical class 0.000 title 1
- -1 2-anilinoethyl Chemical group 0.000 abstract 7
- 150000007524 organic acids Chemical class 0.000 abstract 5
- 125000005907 alkyl ester group Chemical group 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 125000006197 2-benzoyl ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(=O)C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 238000006136 alcoholysis reaction Methods 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 230000000954 anitussive effect Effects 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 239000003434 antitussive agent Substances 0.000 abstract 1
- 229940124584 antitussives Drugs 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 150000002641 lithium Chemical class 0.000 abstract 1
- 239000007937 lozenge Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Novel compounds of the formula and their acid addition salts where R 1 is a C 7-9 alkyl group, a phenylalkyl group having not more than 4 carbon atoms in the alkyl radical, a 2-(N-alkanoylanilino) ethyl group having not more than 4 carbon atoms in the alkanoyl radical, a 2-anilinoethyl, 2-(N-allylanilino)ethyl, a 2-phenoxyethyl, a 2-benzoylethyl or a cinnamyl group and R 2 is a C 1-4 alkyl group are prepared (a) by reacting the alkyl metal derivative of a 1 .substituted-4-alkoxycarbonylpiperidine with a reactive ester of prop-2-yn-l-ol and an inorganic or an organic acid, (b) by subjecting a 1-substituted-4-(prop-2-ynyl)-4-cyanopiperidine to alcoholysis in one of the usual ways, (c) by reacting a 4-alkoxycarbonyl-4- (prop-2-ynyl)piperidine with a reactive ester of an alcohol of the formula R 1 OH and an inorganic or an organic acid or (d) by converting a 1 - substituted - 4 - (prop - 2 - ynyl)piperidine- 4-carboxylic acid into a C 1-4 alkyl ester by one of the usual methods (e.g. via the acid chloride) 1 - Substituted - 4 - alkoxycarbonylpiperidines are prepared by reacting 4-alkoxycarbonylpiperidines with a halo-compound of the formula R 1 HaI, where Hal is chlorine, bromine or iodine, to form a 1 - substituted - 4 - alkoxycarbonylpiperidinium halide which is then hydrogenated in the presence of rhodium on alumina to give a 1 -substituted - 4 -alkozyearbonylpiperidine. 1 - Substituted - 4 - cyano - 4 - (prop - 2 - ynyl)- piperidines are prepared by reacting piperidine- 4-carboxamide with a reactive ester of the alcohol R 1 OH and an inorganic or an organic acid to give a 1 -substituted-piperidine-4-carbox amide and dehydrating the latter with thionyl chloride to give a 1-substituted-4-cyanopiperidene which is then reacted with a reactive ester of prop-2-yn-l-ol and an inorganic or an organic acid. 1 - Substituted - 4 - (prop - 2 - ynyl)piperidine- 4-carboxylic acids are prepared by hydrolysing the corresponding nitriles and the acids are converted into 1 - substituted - 4 - prop - 2 - ynyl)- piperidine-4-carbonyl chlorides with thionyl chloride. 4 - (2 - Propynyl) - isonipecotinic acid C 1-4 alkyl ester is prepared by forming the lithium derivative of 1 - benzyloxycarbonyl - isonipecotinic acid C 1-4 alkyl ester (this alkyl ester is obtainable from isonipecotinic acid ethyl ester and chloroformic acid ethyl ester), treating the lithium-derivative with propargyl bromide and treating the resulting 1-benzyloxycarbonyl-4-(2- propynyl)isonipecotinic acid ethyl ester with HBr. Therapeutic compositions effective as analgesics and antitussives comprise at least one of the novel compounds of the above formula or an acceptable addition salt with an inorganic or an organic acid as the active component and can be administered as dragees, tablets, suppositories, lozenges, syrups and solutions for injection.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1019066 | 1966-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES342933A1 true ES342933A1 (en) | 1968-10-16 |
Family
ID=4360383
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES342934A Expired ES342934A1 (en) | 1966-07-13 | 1967-07-12 | New piperidine derivatives the preparation and compositions containing same |
| ES342936A Expired ES342936A1 (en) | 1966-07-13 | 1967-07-12 | New piperidine derivatives the preparation and compositions containing same |
| ES342935A Expired ES342935A1 (en) | 1966-07-13 | 1967-07-12 | New piperidine derivatives the preparation and compositions containing same |
| ES342933A Expired ES342933A1 (en) | 1966-07-13 | 1967-07-12 | New piperidine derivatives the preparation and compositions containing same |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES342934A Expired ES342934A1 (en) | 1966-07-13 | 1967-07-12 | New piperidine derivatives the preparation and compositions containing same |
| ES342936A Expired ES342936A1 (en) | 1966-07-13 | 1967-07-12 | New piperidine derivatives the preparation and compositions containing same |
| ES342935A Expired ES342935A1 (en) | 1966-07-13 | 1967-07-12 | New piperidine derivatives the preparation and compositions containing same |
Country Status (8)
| Country | Link |
|---|---|
| AT (4) | AT273122B (en) |
| BE (1) | BE701274A (en) |
| ES (4) | ES342934A1 (en) |
| FR (1) | FR6813M (en) |
| GB (1) | GB1203637A (en) |
| GR (1) | GR37586B (en) |
| NL (1) | NL6709699A (en) |
| SE (1) | SE330888B (en) |
-
1967
- 1967-07-12 SE SE1048667A patent/SE330888B/xx unknown
- 1967-07-12 AT AT745268A patent/AT273122B/en active
- 1967-07-12 GB GB32062/67A patent/GB1203637A/en not_active Expired
- 1967-07-12 NL NL6709699A patent/NL6709699A/xx unknown
- 1967-07-12 ES ES342934A patent/ES342934A1/en not_active Expired
- 1967-07-12 GR GR670137586A patent/GR37586B/en unknown
- 1967-07-12 ES ES342936A patent/ES342936A1/en not_active Expired
- 1967-07-12 AT AT745368A patent/AT273123B/en active
- 1967-07-12 BE BE701274D patent/BE701274A/xx unknown
- 1967-07-12 ES ES342935A patent/ES342935A1/en not_active Expired
- 1967-07-12 AT AT652667A patent/AT273119B/en active
- 1967-07-12 AT AT745468A patent/AT273124B/en active
- 1967-07-12 ES ES342933A patent/ES342933A1/en not_active Expired
- 1967-10-10 FR FR123852A patent/FR6813M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GR37586B (en) | 1969-06-21 |
| FR6813M (en) | 1969-03-24 |
| ES342935A1 (en) | 1968-10-16 |
| GB1203637A (en) | 1970-08-26 |
| AT273122B (en) | 1969-08-11 |
| NL6709699A (en) | 1968-01-15 |
| ES342934A1 (en) | 1968-11-16 |
| AT273123B (en) | 1969-08-11 |
| SE330888B (en) | 1970-12-07 |
| AT273119B (en) | 1969-08-11 |
| ES342936A1 (en) | 1969-01-16 |
| AT273124B (en) | 1969-08-11 |
| BE701274A (en) | 1968-01-12 |
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