US3153046A - New alkyl-piperidines - Google Patents

New alkyl-piperidines Download PDF

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US3153046A
US3153046A US111490A US11149061A US3153046A US 3153046 A US3153046 A US 3153046A US 111490 A US111490 A US 111490A US 11149061 A US11149061 A US 11149061A US 3153046 A US3153046 A US 3153046A
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acid
grams
methanol
pyridylmethanol
lauryl
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Hoffmann Karl
Sury Ernst
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BASF Corp
Novartis Corp
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Ciba Geigy Corp
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    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—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
    • C07D211/20—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

Definitions

  • the present invention concerns di-alkyl-piperidylmethanols of the formula in which Pi represents a piperidyl radical, R, and R alkyl radicals containing from 4 to. 16 carbon atoms, and their acid addition salts and quaternary ammonium salts.
  • R and K may be different but they are preferably identical.
  • the piperidyl radical which is connected with vthe radical of the molecule in positions 2,3 or 4 and preferably in position 3 or 4,,may be substituted by lower alkyl groups in any position, for instance methyl, ethyl, propyl, butyl; especially it is substituted at the nitrogen atom by lower alkyl or hydroxyalkyl groups.
  • Suitable substituents at the nitrogen are for instance methyl, ethyl or propyl, hydroxyethyl or hydroxypropyl.
  • quaternary ammonium salts areabove all lower alkyl-ammonium salts, the anion bei'ng selected from the group consisting of mineral acids, for instance hydrohalic acids, such as hydrochloric acid,
  • hydrobromic acid or hydroiodic acid or sulfuric acid or of organic sulfonic acids, for instance lower alkyl sulfonic acids such as methane or ethane sulfonic acid or aryl sulfonic acids, such as benzene sulfonic acid, p-toluene sulfonic acid, p-bromobenz'ene sulfonic acid.
  • lower alkyl sulfonic acids such as methane or ethane sulfonic acid or aryl sulfonic acids, such as benzene sulfonic acid, p-toluene sulfonic acid, p-bromobenz'ene sulfonic acid.
  • the new compounds possess valuable properties. Inter alia they have fungicidal and especially antibacterial properties, for example against Micr osporum audouini, Trichophyton interdigitalis and Staphylococcus aureus and they. act against tubercle bacilli and can therefore be used as disinfectants, preservatives or medicaments for the treatment of'bacterial infections, for example such as, have been caused by the abovementioned organisms.
  • R, and R have the above meaning and Py represents an unsubstituted or lower alkyl substituted pyridyl radical, can be treated with a hydrogenating agent.
  • the hydrogenation can be carried out with an agent knownto be suitable for hydrogenating a pyridine ring.
  • the hydrogenation is carried out with hydrogen in the presence of a catalyst of a metal of the eighth group of the Periodic System, preferably a noble metal catalyst such as platinum or palladium, for example with platinum in glacial acetic acid or palladium carbon in alcohol or isopropanol, or in the presence of cobalt or nickel (Raney or Rupe).
  • a catalyst of a metal of the eighth group of the Periodic System preferably a noble metal catalyst such as platinum or palladium, for example with platinum in glacial acetic acid or palladium carbon in alcohol or isopropanol, or in the presence of cobalt or nickel (Raney or Rupe).
  • a secondary alkyl-piperidine compound obtained by the present process can be converted into a tertiary compound in the known manner. It can, for example, by
  • a tertiary amino compound obtained by the present process can be quaternated in the conventional manner, preferably with a reactive ester of a lower alkanol, such as an ester thereof with a mineral acid or an organic sulfonic acid as mentioned above, for example a hydrohalic acid, sulfuric acid or an arylsulfonic acid.
  • a reactive ester of a lower alkanol such as an ester thereof with a mineral acid or an organic sulfonic acid as mentioned above, for example a hydrohalic acid, sulfuric acid or an arylsulfonic acid.
  • the new compounds are obtained in the form of their bases or salts. From the salts the free bases can be prepared in the known manner.
  • an alkyl pyridine of the formula preparation of therapeutically useful salts yields salts, for example those of the hydrohalic acids, e.g., hydrochloric or hydrobromic acid, perchloric acid, nitric or thiocyanic acid, or sulfuric acid, or phosphoric acid, or organic acids, such as formic acid, acetic acid, propionic acid, glycollic acid, lactic acid, pyruvic acid, oxalic acid, malonic acid, succinic acid, 'rnaleic acid, furnaric acid, malic acid, tartaric acid, citric acid, ascorbic acid, hydroxy maleic acid, dihydroxymaleic acid, benzoic'acid, phenylacetic acid, 4- aminobenzoic acid, 4-hydroxybenzoic acid, anthranilic acid, cinnarnic acid, mandelic acid, salicyclic acid, 4- aminosalicyclic acid, 2-phenoxybenzoic acids,
  • the new'comp'oun'ds may containasymm-etrical carbon atoms so that they, are obtained in the form of racemate method, such as crystallization.-
  • racemate method such as crystallization.
  • the individual racemates can be resolved into their optically active antipodes by the conventional method.
  • the starting materials are known or can be made by as'such known methods.
  • the new compounds can be used in human. or" veterinary medicine as medicaments in the form of pharmaceutical preparations containing them in admixture with a suitable vehicle or diluent.
  • suitable vehicles are, for example, substances that do not react with the new compounds, such as Water, gelatine, lactose, starch, magnesium stearate, talc,v vegetable oils, benzyl alcohols, gums, polyalylene glycols, white petroleum, jelly, cholesteiol or other known medicinal, vehicles.
  • the pharmaceutical preparations may, be, for example, tablets, drages, powders, ointments, creams, suppositories or in liquid form solutions, suspensions or emulsions. They may be sterilized'and/or may contain assistants such as preservatives, stabilizers, wettingagents or emulsifiers. They may further contain other therapeutically valuable substances.
  • the new compounds are also suitable as'disi nfectants or preservatives, for example for disinfecting the skin, for example the hands, instruments, underwear or the like, and also for disinfecting or preserving victuals or feedingstuifs. They may be applied by themselves or in admixture ina solution or emulsion and/or with other active principles or inert substances, such as ointments, or in the form of dry powders.
  • Example 1 A solution of 98 grams of di-lauryl-3-pyridylmethanol in 400 cc. of isopropanol is hydrogenated with the" aid of 5 grams of palladium carbon of strength as catalyst in an autoclave with hydrogen at 115 C. under a pressure of 100 atmospheres gauge until the pressure re.- mains constant. The catalyst ,is then filtered off, the solvent is evaporated and the residue (95 grams) is distilled in a high vacuum.
  • Di-lauryl-B-piperidylmethanol boils at 231-240" C. under a pressure of 0.12 mm. Hg or at 130-135 C. under a pressure of 11.5 microns (molecular distillation apparatus). It corresponds to the formula lNH
  • the acetate respectively is obtained.
  • the aforementioned starting material is prepared by adding a solution of 30.2 grams of nicotinic acid ethyl ester in 250 cc. of toluene dropwise at 30-50 C. to an ethereal solution of the Grignard compound prepared from 12.15 grams of magnesium and 131 grams of lauryl bromide and stirring the mixture for 4 hours at 60 C. under nitrogen.
  • the Grignard complex is decomposed in a solution of ammonium chloride which is then worked up in the usual manner, the whole is distilled in a high vacuum and the forerunnings are separated, whereupon di-lauryl-3-pyridylmethanol is obtained.
  • nicotinic acid ethyl ester instead of nicotinic acid ethyl ester it is possible to use nicotinicacid'rnethyl ester which boils at 235237 C. under 0.05 mm. Hg pressure.
  • Example. 2 a A solution of 19.4 grams 0f di-lauryl-4-pyridyl- Di-hexadeoyl-3piperidylmethanoL i Example 3 The following compounds are prepared as described in Examples 1 and 2:
  • Di-butyl-B-pyridylmethanol Di-hexyl-3-pyridylmethanol Di-octyl-3-pyridylmethanoL Di-decyl-3-pyridy1meth anoi. Di-hexadecyl-3-pyridylmethanol Di-butyM-pwidylmethanoi Di-hexyl-d-pyridylmethanol Di-ootyl-4-pyridylmethanoL. Di-deeyl-4-pyridylmethanoL Di-hexadecyl-4-pyridylmethanol.-
  • Example 4 When a mixture of a solution of 8 grams of di-lauryl-3- pyridylmethanol in 60 cc. of ethyl acetate and 2.7 grams (:2 cc.) of dimethyl sulfate is left to itself for one hour, then evaporated to dryness, the di-lauryl-3-pyridylmethanol-methosulfate formed is dissolved in cc. of methanol and the solution is hydrogenated with 0.5 gram of platinum oxide under hydrogen at 25 C. under atmospheric pressure, di lauryl 3 (l-methyl-piperidiyl)-methanol of the formula '7 F z5Cia-(I3C12H2s methanol in 100 cc.
  • R stands for a member selected from the group consisting of hydrogen, lower alkyl and hydroxyalkyl and each of the letters It and m stands for one of the integers from 5 to 11, inclusive, and a therapeutically useful acid addition salt thereof and a quaternary lower alkyl ammonium salt thereof.

Description

Tweak- United States Patent 3,153,046 r NEW ALKYL-PIPERIDINES Karl Hoifmann, Binningen, and Ernst Snry, Basel, Switzerland, assignors to Ciba Corporation, a corporation of Delaware No Drawing. Filed May 22, 1961, Ser. No. 111,490 Claims priority, application Switzerland, May 20, 1960,
. 5,818/ 60 11 Claims. (Cl. 260-2934) ."The present invention concerns di-alkyl-piperidylmethanols of the formula in which Pi represents a piperidyl radical, R, and R alkyl radicals containing from 4 to. 16 carbon atoms, and their acid addition salts and quaternary ammonium salts. R and K, may be different but they are preferably identical.
The piperidyl radical, which is connected with vthe radical of the molecule in positions 2,3 or 4 and preferably in position 3 or 4,,may be substituted by lower alkyl groups in any position, for instance methyl, ethyl, propyl, butyl; especially it is substituted at the nitrogen atom by lower alkyl or hydroxyalkyl groups. Suitable substituents at the nitrogen are for instance methyl, ethyl or propyl, hydroxyethyl or hydroxypropyl.
For the present purpose quaternary ammonium salts areabove all lower alkyl-ammonium salts, the anion bei'ng selected from the group consisting of mineral acids, for instance hydrohalic acids, such as hydrochloric acid,
hydrobromic acid or hydroiodic acid, or sulfuric acid or of organic sulfonic acids, for instance lower alkyl sulfonic acids such as methane or ethane sulfonic acid or aryl sulfonic acids, such as benzene sulfonic acid, p-toluene sulfonic acid, p-bromobenz'ene sulfonic acid.
The new compounds possess valuable properties. Inter alia they have fungicidal and especially antibacterial properties, for example against Micr osporum audouini, Trichophyton interdigitalis and Staphylococcus aureus and they. act against tubercle bacilli and can therefore be used as disinfectants, preservatives or medicaments for the treatment of'bacterial infections, for example such as, have been caused by the abovementioned organisms.
3,153,046 Patented Get. 13,1964
ice
in which R, and R have the above meaning and Py represents an unsubstituted or lower alkyl substituted pyridyl radical, can be treated with a hydrogenating agent.
The hydrogenation can be carried out with an agent knownto be suitable for hydrogenating a pyridine ring. Thus, for example, the hydrogenation is carried out with hydrogen in the presence of a catalyst of a metal of the eighth group of the Periodic System, preferably a noble metal catalyst such as platinum or palladium, for example with platinum in glacial acetic acid or palladium carbon in alcohol or isopropanol, or in the presence of cobalt or nickel (Raney or Rupe).
A secondary alkyl-piperidine compound obtained by the present process can be converted into a tertiary compound in the known manner. It can, for example, by
. alkylated in the usual manner or converted into the corresponding tertiary hydroxyalkyl derivative, for example, by treatment with a 1:2-alkylene oxide.
A tertiary amino compound obtained by the present process can be quaternated in the conventional manner, preferably with a reactive ester of a lower alkanol, such as an ester thereof with a mineral acid or an organic sulfonic acid as mentioned above, for example a hydrohalic acid, sulfuric acid or an arylsulfonic acid.
Depending on the procedure used the new compounds are obtained in the form of their bases or salts. From the salts the free bases can be prepared in the known manner.
Reaction of a free base with an acid suitable for the Of special value inthis respect are the compounds-of the formula v l 3 2) 5-n z) 511 113 as well as their therapeutically useful acid addition salts and quaternary lower alkyl-ammonium salts which are distinguished also by their stability towards soap and sera. Special mention deserve di-octyl-3-piperidylmethadi-octyl-4-piperidylmethanol, di-decyl-Z-piperidyh methanol, di hexyl-3-piperidylmethanol, di-heXyl-4-piperidylm'ethanol, their acid addition salts and quaternary ammonium salts.
The new compounds are obtained by methods as such know-n, Thus an alkyl pyridine of the formula preparation of therapeutically useful salts yields salts, for example those of the hydrohalic acids, e.g., hydrochloric or hydrobromic acid, perchloric acid, nitric or thiocyanic acid, or sulfuric acid, or phosphoric acid, or organic acids, such as formic acid, acetic acid, propionic acid, glycollic acid, lactic acid, pyruvic acid, oxalic acid, malonic acid, succinic acid, 'rnaleic acid, furnaric acid, malic acid, tartaric acid, citric acid, ascorbic acid, hydroxy maleic acid, dihydroxymaleic acid, benzoic'acid, phenylacetic acid, 4- aminobenzoic acid, 4-hydroxybenzoic acid, anthranilic acid, cinnarnic acid, mandelic acid, salicyclic acid, 4- aminosalicyclic acid, 2-phenoxybenzoic acid, Z-acetoxybenzoic acid, methanesulfonic acid, ethanesulfonic acid, hydroxyethanesulfonic acid, benzeneor p-toluenesulfonic acid, naphthalenesulfoni'cacid, or sulfanilic acid.
The new'comp'oun'ds may containasymm-etrical carbon atoms so that they, are obtained in the form of racemate method, such as crystallization.- The individual racemates can be resolved into their optically active antipodes by the conventional method.
The starting materials are known or can be made by as'such known methods.
The new compounds can be used in human. or" veterinary medicine as medicaments in the form of pharmaceutical preparations containing them in admixture with a suitable vehicle or diluent. Suitable vehicles are, for example, substances that do not react with the new compounds, such as Water, gelatine, lactose, starch, magnesium stearate, talc,v vegetable oils, benzyl alcohols, gums, polyalylene glycols, white petroleum, jelly, cholesteiol or other known medicinal, vehicles. The pharmaceutical preparations may, be, for example, tablets, drages, powders, ointments, creams, suppositories or in liquid form solutions, suspensions or emulsions. They may be sterilized'and/or may contain assistants such as preservatives, stabilizers, wettingagents or emulsifiers. They may further contain other therapeutically valuable substances.
The new compounds are also suitable as'disi nfectants or preservatives, for example for disinfecting the skin, for example the hands, instruments, underwear or the like, and also for disinfecting or preserving victuals or feedingstuifs. They may be applied by themselves or in admixture ina solution or emulsion and/or with other active principles or inert substances, such as ointments, or in the form of dry powders.
The following examples illustrate the invention without restricting its scope thereto.
Example 1 A solution of 98 grams of di-lauryl-3-pyridylmethanol in 400 cc. of isopropanol is hydrogenated with the" aid of 5 grams of palladium carbon of strength as catalyst in an autoclave with hydrogen at 115 C. under a pressure of 100 atmospheres gauge until the pressure re.- mains constant. The catalyst ,is then filtered off, the solvent is evaporated and the residue (95 grams) is distilled in a high vacuum.
Di-lauryl-B-piperidylmethanol boils at 231-240" C. under a pressure of 0.12 mm. Hg or at 130-135 C. under a pressure of 11.5 microns (molecular distillation apparatus). It corresponds to the formula lNH When the product is dissolved in methanol, treated with a calculated amount of hydrochloric or acetic acid and evaported, the hydrochloride (M.P.=8486 C.) and the acetate respectively is obtained.
The aforementioned starting material is prepared by adding a solution of 30.2 grams of nicotinic acid ethyl ester in 250 cc. of toluene dropwise at 30-50 C. to an ethereal solution of the Grignard compound prepared from 12.15 grams of magnesium and 131 grams of lauryl bromide and stirring the mixture for 4 hours at 60 C. under nitrogen. The Grignard complex is decomposed in a solution of ammonium chloride which is then worked up in the usual manner, the whole is distilled in a high vacuum and the forerunnings are separated, whereupon di-lauryl-3-pyridylmethanol is obtained.
Instead of nicotinic acid ethyl ester it is possible to use nicotinicacid'rnethyl ester which boils at 235237 C. under 0.05 mm. Hg pressure.
I Example. 2 a A solution of 19.4 grams 0f di-lauryl-4-pyridyl- Di-hexadeoyl-3piperidylmethanoL i Example 3 The following compounds are prepared as described in Examples 1 and 2:
Di-deeyl-3-piperidyimethanoL. I
Di-butyl-ipiperidylmethanoi. Di-hexyl-4 piperidylmethanol Di-octyl-4-piperidylmethanoL Di-deeyli-pipcridylmethanol Di-hexadecyl-4-piperidylmethanol The starting materials to be used described in Example 1:
Boilin Under Melting atC. mm.Hg atC Di-butyl-B-pyridylmethanol. Di-hexyl-3-pyridylmethanol Di-octyl-3-pyridylmethanoL Di-decyl-3-pyridy1meth anoi. Di-hexadecyl-3-pyridylmethanol Di-butyM-pwidylmethanoi Di-hexyl-d-pyridylmethanol Di-ootyl-4-pyridylmethanoL. Di-deeyl-4-pyridylmethanoL Di-hexadecyl-4-pyridylmethanol.-
Example 4 Whena mixture of a solution of 8 grams of di-lauryl-3- pyridylmethanol in 60 cc. of ethyl acetate and 2.7 grams (:2 cc.) of dimethyl sulfate is left to itself for one hour, then evaporated to dryness, the di-lauryl-3-pyridylmethanol-methosulfate formed is dissolved in cc. of methanol and the solution is hydrogenated with 0.5 gram of platinum oxide under hydrogen at 25 C. under atmospheric pressure, di lauryl 3 (l-methyl-piperidiyl)-methanol of the formula '7 F z5Cia-(I3C12H2s methanol in 100 cc. of methanol and 5 cc. of acetic acid 7 is hydrogenated with the aid of 1.5 grams of platinum oxide as catalyst with hydrogen under atmospheric pressure at 25 C. The catalyst is filtered ofi, the solvent evaporated, the residue is rendered alkaline (pl-1:11)
extracted with ether, the ether solution is washed until neutral'and then dried and the ether is distilled off. The residue is then distilled in a high vacuum to yield 16 with sodium hydroxide solution, the precipitated oil is grams of -di-lauryl-4-piperidylmethanol of the formula is obtained which boils at 230-232 C. under a pressure of 0.09 mm. Hg.
Example 5 i lauryl-3-(l-methyl-piperidyl)-methanol of the'formula N-OH; 1e
v p 0113 crystallizes out; it melts at -86 C.
. 5 Example grams of ethylene oxide are added to a solution of 10 grams of di-lauryl-3-piperidyl-methanol in 50 cc. of
methanol; The additive reaction is catalyzed by adding 1 cc. of N-acetic acid. The reaction mixture is kept overnight, evaporated to dryness and the residue is disa.) tilled in a high vacuum, to yield di-lauryl-3-(1-5-hydroxyethyl-piperidy1)-methanol of the formula OH 7 25 l2- 12 25 What is claimed is:
1. A member selected from the group consisting of a compound of the formula wherein R stands for a member selected from the group consisting of hydrogen, lower alkyl and hydroxyalkyl and each of the letters It and m stands for one of the integers from 5 to 11, inclusive, and a therapeutically useful acid addition salt thereof and a quaternary lower alkyl ammonium salt thereof. 9 I 2. The compound di-octyl-3-piperidyl-methanol.
3. The compound di-octyl-4-piperidyl-rnethanol.
4. The compound di-heXyl-3-piperidyl-methanol.
5. The compound di-hexyl-4-piperidyl-rnethanol.
References Cited in the file of this patent UNITED STATES PATENTS Sperber et al Mar. 27, 1956 OTHER REFERENCES Winterfield et al.: Chemical Abstracts," vol. 29, page 7331 (1935).
Tilford et al.: Journ. Am. Chem. 800., vol. 70, pages 4001-08 (1948).
Sperber et al.: Journ. Am. Chem. Soc, vol. 887- (1949).
McCarty et al.: Journ. Amer. Chem. Soc, vol. 79, pages 472-480 (1957).
Parkin et al.: "Journ. Am. Chem. 800., vol. 80, 2899- 2902 (1958).

Claims (3)

1. A MEMBER SELECTED FROM THE GROUP CONSISTING OF A COMPOUND OF THE FORMULA
2. THE COMPOUND DI-OCTYL-3-PIPERIDYL-METHANOL.
7. A THERAPEUTICALLY USEFUL ACID ADDITION SALT OF THE COMPOUND OF CLAIM 2.
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3422451A (en) * 1965-07-13 1969-01-14 Merck & Co Inc Alpha,alpha,1,6-tetramethyl-3-piperidinemethanols and their preparation
DE1670647A1 (en) * 1967-01-13 1971-03-18 Lilly Co Eli Fungicide
US4002628A (en) * 1973-06-18 1977-01-11 Eli Lilly And Company Novel fluoroalkoxyphenyl-substituted nitrogen heterocycles
US4039675A (en) * 1972-09-15 1977-08-02 Eli Lilly And Company α,α-Dialkyl-substituted 3-pyridinemethanols as fungicidal agents

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2739968A (en) * 1950-12-05 1956-03-27 Schering Corp Substituted piperidines

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2739968A (en) * 1950-12-05 1956-03-27 Schering Corp Substituted piperidines

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3422451A (en) * 1965-07-13 1969-01-14 Merck & Co Inc Alpha,alpha,1,6-tetramethyl-3-piperidinemethanols and their preparation
DE1670647A1 (en) * 1967-01-13 1971-03-18 Lilly Co Eli Fungicide
US4039675A (en) * 1972-09-15 1977-08-02 Eli Lilly And Company α,α-Dialkyl-substituted 3-pyridinemethanols as fungicidal agents
US4002628A (en) * 1973-06-18 1977-01-11 Eli Lilly And Company Novel fluoroalkoxyphenyl-substituted nitrogen heterocycles

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