GB1338056A - Tetrahydropyridine derivatives and a process for the manufacture thereof - Google Patents

Tetrahydropyridine derivatives and a process for the manufacture thereof

Info

Publication number
GB1338056A
GB1338056A GB2813671A GB2813671A GB1338056A GB 1338056 A GB1338056 A GB 1338056A GB 2813671 A GB2813671 A GB 2813671A GB 2813671 A GB2813671 A GB 2813671A GB 1338056 A GB1338056 A GB 1338056A
Authority
GB
United Kingdom
Prior art keywords
cycloalkyl
alkyl
compound
compounds
phenyltetrahydropyridine
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
GB2813671A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1338056A publication Critical patent/GB1338056A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
    • 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
    • C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent 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
    • C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Abstract

1338056 Tetrahydropyridine derivatives F HOFFMANN-LA ROCHE & CO AG 16 June 1971 [19 June 1970] 28136/71 Heading C2C The invention comprises compounds of formula and their acid addition salts, wherein R<SP>1</SP> is H, alkanoyl, alkylsulphonyl, alkyl, cycloalkyl or cycloalkyl-alkyl, R<SP>2</SP> is H, alkyl, cycloalkyl or cycloalkyl-alkyl, X is O or S, and Y is F, Cl or alkoxy, each of the specified organic radicals containing up to 6 carbon atoms. These compounds may be prepared by (1) condensing together the correspondingly substituted (a) phenoxyethyl or phenylthioethyl compound and phenyltetrahydropyridine, or (b) phenyltetrahydro-1- pyridylethyl compound and p-R<SP>1</SP>R<SP>2</SP>NC 6 H 4 XM (M = alkali metal or Mg-halide); (2) dehydrating the corresponding 4-hydroxypiperidine; (3) treating with mineral acid the corresponding 6-methyl-1,3-oxazine (whereby the oxazine rearranges to the tetrahydropyridine); (4) reducing a corresponding 1-(p-nitrophenoxyethyl- or p-nitrophenylthioethyl)-4-phenyltetrahydropyridine or the 1-(p-aminophenoxyacetyl- or p-aminophenylthioacetyl-), or the 1-(p-nitrophenoxyacetyl- or p - nitrophenylthioacetyl-) analogues; and optionally (5) alkanoylating, alkylsulphonylating, alkylating, cycloalkylating or cycloalkyl-alkylating the amine, or hydrolysing the alkanoylamino compound. Therapeutic compositions for oral, parenteral or rectal administration comprise compounds of the above formula, which have psychosedative activity.
GB2813671A 1970-06-19 1971-06-16 Tetrahydropyridine derivatives and a process for the manufacture thereof Expired GB1338056A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH931870A CH547802A (en) 1970-06-19 1970-06-19 PROCESS FOR THE PRODUCTION OF TETRAHYDROPYRIDE DERIVATIVES.

Publications (1)

Publication Number Publication Date
GB1338056A true GB1338056A (en) 1973-11-21

Family

ID=4350687

Family Applications (5)

Application Number Title Priority Date Filing Date
GB4688472A Expired GB1338058A (en) 1970-06-19 1971-06-16 Oxazine derivatives
GB4688572A Expired GB1338059A (en) 1970-06-19 1971-06-16 Substituted tetrahydropyridines
GB2813671A Expired GB1338056A (en) 1970-06-19 1971-06-16 Tetrahydropyridine derivatives and a process for the manufacture thereof
GB4688372A Expired GB1338057A (en) 1970-06-19 1971-06-16 Piperidine derivatives
GB4688672A Expired GB1338060A (en) 1970-06-19 1971-06-16 Substituted tetrahydropyridines

Family Applications Before (2)

Application Number Title Priority Date Filing Date
GB4688472A Expired GB1338058A (en) 1970-06-19 1971-06-16 Oxazine derivatives
GB4688572A Expired GB1338059A (en) 1970-06-19 1971-06-16 Substituted tetrahydropyridines

Family Applications After (2)

Application Number Title Priority Date Filing Date
GB4688372A Expired GB1338057A (en) 1970-06-19 1971-06-16 Piperidine derivatives
GB4688672A Expired GB1338060A (en) 1970-06-19 1971-06-16 Substituted tetrahydropyridines

Country Status (16)

Country Link
AT (5) AT309428B (en)
BE (1) BE768689A (en)
CA (1) CA984844A (en)
CH (1) CH547802A (en)
DE (1) DE2128836A1 (en)
DK (1) DK132887C (en)
ES (1) ES392388A1 (en)
FR (1) FR2100797B1 (en)
GB (5) GB1338058A (en)
HU (1) HU162417B (en)
IE (1) IE35369B1 (en)
IL (1) IL36827A (en)
NL (1) NL7108416A (en)
NO (1) NO133548C (en)
SE (1) SE378814B (en)
ZA (1) ZA713032B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4985074A (en) * 1972-12-22 1974-08-15

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4320131A (en) * 1981-03-16 1982-03-16 Mead Johnson & Company N-[(4-Phenyl-1,2,3,6-tetrahydropyridin-1-yl)alkylene]azaspiroalkanediones and N-[(4-hydroxy-4-phenylpiperidin-1-yl)alkylene]azaspiroalkanediones
AU717140B2 (en) * 1996-03-08 2000-03-16 F. Hoffmann-La Roche Ag Use of 4-phenyl-3,6-dihydro-2H-pyridyl derivatives as NMDA receptor subtype blockers

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH506525A (en) * 1968-12-24 1971-04-30 Hoffmann La Roche Aromatic ethers

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4985074A (en) * 1972-12-22 1974-08-15

Also Published As

Publication number Publication date
NL7108416A (en) 1971-12-21
AT309428B (en) 1973-08-27
GB1338059A (en) 1973-11-21
FR2100797B1 (en) 1974-08-23
CH547802A (en) 1974-04-11
FR2100797A1 (en) 1972-03-24
DK132887B (en) 1976-02-23
CA984844A (en) 1976-03-02
SE378814B (en) 1975-09-15
ES392388A1 (en) 1973-08-01
GB1338060A (en) 1973-11-21
DE2128836A1 (en) 1971-12-23
AT309432B (en) 1973-08-27
HU162417B (en) 1973-02-28
ZA713032B (en) 1972-01-26
GB1338058A (en) 1973-11-21
DK132887C (en) 1976-07-26
AT309431B (en) 1973-08-27
IE35369B1 (en) 1976-01-21
IL36827A0 (en) 1971-07-28
AT309433B (en) 1973-08-27
AT311971B (en) 1973-12-10
NO133548C (en) 1976-05-19
IL36827A (en) 1974-10-22
NO133548B (en) 1976-02-09
BE768689A (en) 1971-12-20
IE35369L (en) 1971-12-19
GB1338057A (en) 1973-11-21

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee