GB1316424A - Alpha-hydroxy-substituted-phenyl-alpha-2-piperidyl-methanols and process for the preparation thereof - Google Patents

Alpha-hydroxy-substituted-phenyl-alpha-2-piperidyl-methanols and process for the preparation thereof

Info

Publication number
GB1316424A
GB1316424A GB2563469A GB1316424DA GB1316424A GB 1316424 A GB1316424 A GB 1316424A GB 2563469 A GB2563469 A GB 2563469A GB 1316424D A GB1316424D A GB 1316424DA GB 1316424 A GB1316424 A GB 1316424A
Authority
GB
United Kingdom
Prior art keywords
pyridyl
alkoxy
phenyl
alkyl
poly
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
Application number
GB2563469A
Inventor
G H Sankey
K D E Whiting
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Minnesota 3M Laboratories Ltd
Original Assignee
Minnesota 3M Laboratories Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Minnesota 3M Laboratories Ltd filed Critical Minnesota 3M Laboratories Ltd
Publication of GB1316424A publication Critical patent/GB1316424A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D211/02—Preparation by ring-closure or hydrogenation
    • 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
    • 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
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

1316424 α - Hydroxyphenyl - α - (2 - piperidyl)- methanols MINNESOTA 3M LABORATORIES Ltd 19 May 1970 [20 May 1969] 25634/69 Heading C2C Novel α - hydroxyphenyl - α - (2 - piperidyl)- methanols of the general formula wherein R is a hydrogen atom or alkyl group; R<SP>1</SP> is a hydrogen atom or a hydroxy or C 1-6 alkoxy group; and R<SP>2</SP> is a hydrogen atom or an alkyl, phenyl, phenyl-alkyl, diphenyl-alkyl, phenoxy - alkyl or diphenoxy - alkyl group ("alkyl" meaning C 1-6 alkyl or C 3-6 cycloalkyl in these definitions); and pharmaceutically acceptable acid addition and quaternary ammonium salts thereof are prepared (a) by hydrogenating in the presence of a catalyst a compound of the general formula wherein B is CO or CHOH. Polyhydroxyphenyl 2-pyridyl ketones of the second general formula above wherein B is CO and R<SP>2</SP> is a hydrogen atom or alkyl group are prepared by condensing a poly-C 1-6 alkoxybenzaldehyde with a picolinic acid, oxidizing the resulting α-(poly-C 1-6 alkoxyphenyl)-α-(2- pyridyl)-methanol and dealkylating the resulting poly-C 1-6 alkylphenyl 2-pyridyl ketone. α - (C 1-6 alkoxy - p - hydroxyphenyl) - α- (2-pyridyl)-methanols of the second general formula above wherein B is CHOH and R<SP>2</SP> is a hydrogen atom or alkyl group are prepared by treating a C 1-6 alkoxy-p-benzyloxybenzaldehyde with a 2-pyridyllithium and hydrogenating the resulting α - (C 1-6 alkoxy - p - benzyloxy - phenyl)- α - (2 - pyridyl) - methanol. They may be oxidized to give the corresponding ketones (B is CO). Polyhydroxyphenyl 2 - pyridyl ketones of the second general formula above wherein B is CO and R<SP>2</SP> is a phenethyl or dibenzylmethyl group are prepared by condensing a poly-C 1-6 alkoxy-phenyl methyl-2-pyridyl ketone and 1,3- propanediol in the presence of p-toluenesulphonic acid, treating the resulting 2-(poly- C 1-6 alkoxy - phenol) - 2 - (methyl - 2 - pyridyl)- 1,3-dioxane with phenyllithium and then benzyl chloride and treating the resulting mixture of a 2 - (poly - C 1-6 alkoxy - phenyl) - 2 - (phenethyl- 2 - pyridyl) - 1,3 - dioxane and a 2 - (poly- C 1-6 alkoxy - phenyl) - 2 - (dibenzylmethyl - 2- pyridyl)-1,3-dioxane with HBr. Pharmaceutical compositions having bronchodilatory activity comprise, as active ingredient, an α - hydroxy - phenyl - α - (2 - piperidyl)- methanol of the first general formula above or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof, together with a pharmaceutical diluent or carrier.
GB2563469A 1969-05-20 1969-05-20 Alpha-hydroxy-substituted-phenyl-alpha-2-piperidyl-methanols and process for the preparation thereof Expired GB1316424A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2563469 1969-05-20

Publications (1)

Publication Number Publication Date
GB1316424A true GB1316424A (en) 1973-05-09

Family

ID=10230843

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2563469A Expired GB1316424A (en) 1969-05-20 1969-05-20 Alpha-hydroxy-substituted-phenyl-alpha-2-piperidyl-methanols and process for the preparation thereof

Country Status (12)

Country Link
JP (1) JPS4920787B1 (en)
BE (1) BE750590A (en)
CH (1) CH541557A (en)
DE (1) DE2024049C3 (en)
DK (1) DK124027B (en)
FR (1) FR2051549B1 (en)
GB (1) GB1316424A (en)
IL (1) IL34537A (en)
NL (1) NL169314C (en)
NO (1) NO133448C (en)
SE (1) SE374366B (en)
ZA (1) ZA703208B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991018602A1 (en) * 1990-06-01 1991-12-12 Merrell Dow Pharmaceuticals Inc. (+)-α-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUOROPHENYL)ETHYL]-4-PIPERIDINEMETHANOL
US6004980A (en) * 1990-06-01 1999-12-21 Merrell Pharmaceuticals, Inc. (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol
US6028083A (en) * 1997-07-25 2000-02-22 Hoechst Marion Roussel, Inc. Esters of (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA960676A (en) * 1970-05-21 1975-01-07 Smith Kline And French Canada Ltd. 3-sulfonamido-4-hydroxyphenyl-2-piperidinylcarbinols
US5169096A (en) * 1985-07-02 1992-12-08 Merrell Dow Pharmaceuticals Inc. N-aralkyl-piperidine-methanol derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE569836A (en) *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991018602A1 (en) * 1990-06-01 1991-12-12 Merrell Dow Pharmaceuticals Inc. (+)-α-(2,3-DIMETHOXYPHENYL)-1-[2-(4-FLUOROPHENYL)ETHYL]-4-PIPERIDINEMETHANOL
US5134149A (en) * 1990-06-01 1992-07-28 Merrell Dow Pharmaceuticals Inc. (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol
US5700812A (en) * 1990-06-01 1997-12-23 Merrell Pharmaceuticals Inc. (+)-α-(2,3-dimethoxyphenyl)-1- 2-(4-fluorophenyl)ethyl!-4-piperidinemethanol
US5700813A (en) * 1990-06-01 1997-12-23 Merrell Pharmaceuticals Inc. (+)-α-(2,3-dimethoxyphenyl)-1- 2-(4-fluorophenyl)ethyl!-4-piperidinemethanol
US5874445A (en) * 1990-06-01 1999-02-23 Merrell Pharmaceutical, Inc. (+) -α- (2,3-dimethoxyphenyl)-1-(2-(4-fluorephenyl) ethyl)-4-piepridinemethanol
US6004980A (en) * 1990-06-01 1999-12-21 Merrell Pharmaceuticals, Inc. (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol
US6028083A (en) * 1997-07-25 2000-02-22 Hoechst Marion Roussel, Inc. Esters of (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol
US6063793A (en) * 1997-07-25 2000-05-16 Hoechst Marion Roussel, Inc. Esters of (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidi nemethanol

Also Published As

Publication number Publication date
ZA703208B (en) 1971-01-27
DE2024049B2 (en) 1977-11-24
IL34537A0 (en) 1970-07-19
JPS4920787B1 (en) 1974-05-27
FR2051549A1 (en) 1971-04-09
NO133448C (en) 1976-05-05
NO133448B (en) 1976-01-26
DK124027B (en) 1972-09-04
SE374366B (en) 1975-03-03
NL7007303A (en) 1970-11-24
CH541557A (en) 1973-09-15
NL169314B (en) 1982-02-01
FR2051549B1 (en) 1974-08-30
DE2024049A1 (en) 1970-12-17
NL169314C (en) 1982-07-01
BE750590A (en) 1970-11-19
IL34537A (en) 1973-03-30
DE2024049C3 (en) 1978-07-20

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Legal Events

Date Code Title Description
429A Application made for amendment of specification (sect. 29/1949)
429N Application abandoned (sect. 29/1949)
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee