GB856587A - Substituted piperidines - Google Patents
Substituted piperidinesInfo
- Publication number
- GB856587A GB856587A GB9664/57A GB966457A GB856587A GB 856587 A GB856587 A GB 856587A GB 9664/57 A GB9664/57 A GB 9664/57A GB 966457 A GB966457 A GB 966457A GB 856587 A GB856587 A GB 856587A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- alkyl
- sulphur
- phenyl
- oxygen
- 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
- 125000004432 carbon atom Chemical group C* 0.000 abstract 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- 239000005864 Sulphur Substances 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 239000001301 oxygen Substances 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000005250 alkyl acrylate group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000004792 aryl magnesium halides Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 125000003386 piperidinyl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 229910003870 O—Li Inorganic materials 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- 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
- C07D211/18—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- 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
- C07D211/18—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—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 substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention comprises compounds of the formula: <FORM:0856587/IV(b)/1> (wherein Ar is phenyl or naphthyl which may bear substituents unreactive to lithuim or magnesium under the conditions of forming the corresponding aryl-lithuim or aryl magnesium halide, Z is H or a carboxylic acyl radical having from 2 to 7 carbon atoms, R is an alkyl radical having at most 6 carbon atoms, n is zero or an integer from 1 to 8, X is a divalent aliphatic hydrocarbon radical having 2 to 6 carbon atoms and having its free valencies on different carbon atoms, A is oxygen or sulphur or a direct link between X and Ar1, X being saturated when A is oxygen or p sulphur, and Ar1 is phenyl which may be substituted) and non-toxic acid-addition salts thereof; and their preparation by reacting an appropriate N-(X-A-Ar1)-4-piperidone with an appropriate aryl lithuim or aryl magnesium halide and hydrolysing the N-(X-A-Ar1)-4-Ar-4-(O-Li or O-Mg halide)- piperidine so-obtained or acylating this metal derivative or the free hydroxy compound to form compounds of the general formula I wherein Z is hydrogen or acyl respectively. The acylation is preferably conducted with an acylanhydride, suitable acylating groups being alkanoyl, alkenoyl, alkoxyalkanoyl, carboxy-alkanoyl, benzoyl and furoyl. Preferred substituents for the radicals Ar and Ar1 are alkyl or alkoxy groups containing at most 6 carbon atoms. Examples are given and a list of saltforming organic and inorganic acids is provided. N-(X-A-Ar1)-4-piperidones bearing no alkyl substituents in the piperidine ring are prepared by reacting Ar1-A-X-NH2 with at least 2 molar equivalents of an alkyl acrylate to yield an N:N-bis-(carbalkoxyethyl)-N-(X-A-Ar1)-amine, heating this with a strong basic condensing agent in an inert solvent to form an N-(X-A-Ar1)-3-carbalkoxy -4-piperidone, and hydrolysing and decarboxylating this by refluxing with aqueous acid. Replacement of the alkyl acrylate by other alkyl 2-alkkenoates results in the formation of products containing one of more alkyl substituents in the piperidine ring via the corresponding intermediates. Specification 501,135 is referred to.ALSO:Pharmaceutical compositions contain as essential active ingredient compounds of the formula: <FORM:0856587/VI/1> (wherein Ar is phenyl or naphthyl which may be substituted, Z is H or a carboxylic acyl radical having from 2 to 7 carbon atoms, R is an alkyl radical having at most 6 carbon atoms, n is zero or an integer from 1 to 8, X is a divalent aliphatic hydrocarbon radical having 2 to 6 carbon atoms and having its free valencies on different carbon atoms, A is oxygen or sulphur or a direct link between X and Ar1, X being saturated when A is oxygen or sulphur, and Ar1 is phenyl which may be substituted) or non-toxic acid-addition salts thereof. The compositions may be in liquid or solid form, such as aqueous or aqueous-ethanolic solutions or tablets, powders or capsules, Specification 501,135 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US856587XA | 1956-04-02 | 1956-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB856587A true GB856587A (en) | 1960-12-21 |
Family
ID=22193104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9664/57A Expired GB856587A (en) | 1956-04-02 | 1957-03-25 | Substituted piperidines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB856587A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2027037A1 (en) * | 1968-12-24 | 1970-09-25 | Hoffmann La Roche | |
| FR2156470A2 (en) * | 1971-10-21 | 1973-06-01 | Synthelabo | 1-(3,3-diphenyl-1-propyl)-4-aryl-piperidines - as analgesics spasmolytic and anti-tussive agents |
| JPS4985074A (en) * | 1972-12-22 | 1974-08-15 | ||
| JPS5544068B1 (en) * | 1971-04-15 | 1980-11-10 |
-
1957
- 1957-03-25 GB GB9664/57A patent/GB856587A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2027037A1 (en) * | 1968-12-24 | 1970-09-25 | Hoffmann La Roche | |
| JPS5544068B1 (en) * | 1971-04-15 | 1980-11-10 | ||
| FR2156470A2 (en) * | 1971-10-21 | 1973-06-01 | Synthelabo | 1-(3,3-diphenyl-1-propyl)-4-aryl-piperidines - as analgesics spasmolytic and anti-tussive agents |
| JPS4985074A (en) * | 1972-12-22 | 1974-08-15 |
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