ES346816A1 - 0,3-disubstituted pyrrolidines - Google Patents

0,3-disubstituted pyrrolidines

Info

Publication number
ES346816A1
ES346816A1 ES346816A ES346816A ES346816A1 ES 346816 A1 ES346816 A1 ES 346816A1 ES 346816 A ES346816 A ES 346816A ES 346816 A ES346816 A ES 346816A ES 346816 A1 ES346816 A1 ES 346816A1
Authority
ES
Spain
Prior art keywords
benzyl
pyrrolidinyl
pyrrolidine
alpha
phenyl
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
ES346816A
Other languages
Spanish (es)
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.)
AH Robins Co Inc
Original Assignee
AH Robins Co Inc
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 AH Robins Co Inc filed Critical AH Robins Co Inc
Publication of ES346816A1 publication Critical patent/ES346816A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D267/02—Seven-membered rings
    • C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
    • C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D267/14—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Novel compounds I in which R is H, 1-8C alkyl, 1-8C alkoxy, CF 3 or halo R1 is CH 3 or H (at least one being H) n is 2, 3 or 4 A is O, NR7 (in which R7 is H, 1-8C alkyl, propionyl, 1-8C alkoxy, or carboalkoxy) or a single bond and Z is (a) an R4-substituted phenyl (in which R4 is H, 1-8C alkyl, 1-8C alkoxy, CF 3 , halo or di(1-8C alkyl)amino) or if A is a single bond the following groups (b)-CR2(R8)OH (in which R2 and R3 are H, 1-8C alkyl, phenyl-1-8C alkyl-, cycloalkyl, phenyl or substituted phenyl) (c) -OCONR5(R6) (in which R5 and R6 are H, 1-8C alkyl, or phenyl) (d) or (e) (in which Y is carbonyl or methylene) are prepared by reacting a compound II with a compound III in which X is halo or if n is 2 X may be dialkylamino and in which the oxo group may be ketalized. Intermediates isolated are 1 - benzyl - 3 - phenoxypyrrolidine fumarate 1 - benzyl - 3 - (m - trifluoromethylphenoxy)- pyrrolidine hydrochloride 1 - benzyl - 3 - (o - methoxyphenoxy) - pyrrolidine and its hydrochloride 3 - phenoxy pyrrolidine hydrochloride 3 - (m - trifluoromethylphenoxy)- pyrrolidine hydrochloride 3 - (o - bromophenoxy) - pyrrolidine 1 - benzyl - 3 - (o - hydroxybenzylamino) - pyrrolidine hydrochloride 1 - benzyl - 3 - (2 - hydroxy - 3 - methoxybenzylamino) - pyrrolidine 1 - benzyl - 3 - (2 - hydroxy - 4 - diethylaminobenzylamino) - pyrrolidine 4 - (1 - benzyl - 3 - pyrrolidinyl) - 4,5 - dihydro - 1,4 - benzoxazepin - 3 - (2H) - one hydrochloride 4 - (1 - benzyl - 3 - pyrrolidinyl) - 9 - methoxy - 4,5 - dihydro - 1,4 - benzoxazepin - 3 - (2H) - one 4 - (1 - benzyl - 3 - pyrrolidinyl) - 8 - diethylamino - 4,5 - dihydro - 1,4 - henzoxazepin - 3 - (2H) - one 4 - (3 - pyrrolidinyl) - 4,5 - dihydro - 1,4 - benzoxazepin - 3 - (2H) - one 4 - (3 - pyrrolidinyl) - 9 - methoxy - 4,5 - dihydro - 1,4 - benzoxazepin - 3 - (2H) - one 4 - (3 - pyrrolidinyl) - 8 - diethylamino - 4,5 - dihydro - 1,4 - benzoxazepin - 3 - (2H) - one 1 - benzyl - [alpha] - ethyl - [alpha] - phenyl - 3 - pyrrolidine - methanol 1 - benzyl - 4 - methyl - [alpha] - ethyl - [alpha] - phenyl - 3 - pyrrolidine - methanol 1 - benzyl - [alpha] - methyl - [alpha] - phenyl - 3 - pyrrolidine - methanol 1 - benzyl - [alpha] - methyl - [alpha] - (p - trifluoromethylphenyl) - 3 - pyrrolidine - methanol [alpha] - ethyl - [alpha] - phenyl - 3 - pyrrolidine - methanol [alpha] - methyl - [alpha] - phenyl - 3 - pyrrolidine - methanol: [alpha] - methyl - [alpha] - (p - trifluoromethylphenyl) - 3 - pyrrolidine - methanol [alpha] - benzyl - [alpha] - ethyl - 3 - pyrrolidine - methanol [alpha] - phenyl - 3 - pyrrolidine - methanol [alpha] - cyclohexyl - [alpha] - phenyl - 3 - pyrrolidine - methanol 1 - benzyl - 2 - oxo - [alpha],[alpha] - diphenyl - 3 - pyrrolidine - methanol 1 - benzyl - [alpha],[alpha] - diphenyl - 3 - pyrrolidine - methanol I - benzyl - 3 - (m - trifluoromethylphenyl) - 3 - pyrrolidinol hydrochloride 1 - benzyl - 3 - (p - diethylaminophenyl) - 3 - pyrrolidinol 1 - benzyl - 3 - (o - tolyl) - 3 - pyrrolidinol 3 - (m - trifluoromethylphenyl) - 3 - pyrrolidinol 3 - (p - diethylaminophenyl) - 3 - pyrrolidinol 3 - (o - tolyl - 3 - pyrrolidinol) 3 - (m - trifluoromethyl - phenyl) - pyrrolidino hydrochloride 3 - (p - diethylaminophenyl)- pyrrolidine 3 - (o - tolyl) - pyrrolidine 4,5 - dihydro - 4 - benzyl - 1,4 - benzoxazepin 3 - (2H) - one 4 - benzyl - 9 - methoxy - 4,5 - dihydro - 1,4 - benzoxazepin - 3 - (2H) - one 4 - benzyl - 8 - diethylamino - 4,5 - dihydro - 1,4 - benzoxazepin - 3 - (2H) - one 4 - benzyl - 2,3,4,5 - tetrahydro - 1,4 - benzoxazepine hydrochloride 4 - benzyl - 9 - methoxy - 2,3,4,5 - benzoxazepine 4 - benzyl - 8 - diethylamino - 2,3,4,5 - benzoxazepine 2,3,4,5 - tetrahydro - 1,4 - benzoxazepine hydrochloride 9 - methoxy- 2,3,4,5 - tetrahydro - 1,4 - benzoxazepine 8 - diethylamino - 2,3,4,5 - tetrahydro - 1,4 - benzoxazepine N - (1 - benzyl - 3 - pyrrolidinyl) - phthalimide 4 - trifluoromethyl - N - (1 - benzyl - 3 - pyrrolidinyl) - phthalimide 4,5 - dimethoxy - N - (1 - benzyl - 3 - pyrrolidinyl) - phthalimide 4 - methyl - N - (1 - benzyl - 3 - pyrrolidinyl) - phthalimide N - (1 - benzyl - 3 - pyrrolidinyl) - isoindoline dihydrochloride 4 - trifluoromethyl - N - (1 - benzyl - 3 - pyrrolidinyl) - isoindoline: 4,5 - dimethoxy - N - (1 - benzyl - 3 - pyrrolidinyl) - isoindoline 4 - methyl - N - (1 - henzyl - 3 - pyrrolidinyl) - isoindoline N - (3 - pyrrolidinyl) - isoindoline dihydrochloride N - (3 - pyrrolidinyl) - 4 - trifluoromethyl - isoindoline N - (3 - pyrrolidinyl) - 4,5 - dimethoxy - isoindoline N - (3 - pyrrolidinyl) - 4 - methyl - isoindoline 4 - (1 - benzyl - 3 - pyrrolidinyl) - 2,3,4,5 - tetrahydro - 1,4 - benzoxazepine difumarate 4 - (1 - benzyl - 3 - pyrrolidinyl) - 9 - methoxy - 2,3,4,5 - tetrahydro - 1,4 - benzoxazepine 4 - (1 - benzyl - 3 - pyrrolidinyl) - 8 - diethylamino - 2,3,4,5 - tetrahydro -1,4 - benzoxazepine 4 - (3 - pyrrolidinyl) - 2,3,4,5 - tetrahydro - 1,4 - benzoxazepine difumarate 4 - (3 - pyrrolidinyl) - 9 - methoxy - 2,3,4,5 - tetrahydro - 1,4 - benzoxazepine 4 - (3 - pyrrolidinyl) - 8 - diethylamino - 2,3,4,5 - tetrahydro - 1,4 - benzoxazepine 2 - (1 - benzyl - 3 - pyrrolidinyl) - benzimidazole 2 - (3 - pyrrolidinyl) - benzimidazole dihydrochloride 1 - benzyl - 3 - (2 - methoxyanilino) - pyrrolidine fumarate 3 - (2 - methoxyanilino) - pyrrolidine hexamate 3 - anilino - pyrrolidine 3 - anilino - aspartimide 1 - (3 - benzoylpropyl) - 3 - pyrrolidinol and 1 - [3 - (4 - fluorobenzoylpropyl)]- 3 - pyrrolidinol. Pharmaceutical compositions comprise a compound I in association with a suitable carrier, are administered orally or parenterally and are useful as analgesics and tranquilizers.
ES346816A 1966-11-07 1967-11-06 0,3-disubstituted pyrrolidines Expired ES346816A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US59226366A 1966-11-07 1966-11-07

Publications (1)

Publication Number Publication Date
ES346816A1 true ES346816A1 (en) 1969-04-16

Family

ID=24369972

Family Applications (1)

Application Number Title Priority Date Filing Date
ES346816A Expired ES346816A1 (en) 1966-11-07 1967-11-06 0,3-disubstituted pyrrolidines

Country Status (12)

Country Link
AT (1) AT272331B (en)
BE (1) BE704683A (en)
CA (1) CA955936A (en)
CH (1) CH511834A (en)
DE (1) DE1695652A1 (en)
DK (1) DK133942B (en)
ES (1) ES346816A1 (en)
FR (2) FR1575543A (en)
GB (1) GB1202747A (en)
IL (1) IL28811A (en)
NL (1) NL6714553A (en)
SE (1) SE315594B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54151990A (en) * 1978-04-17 1979-11-29 Beiersdorf Ag Novel condensated nitrogenncontained heterocyclic compound and its manufacture
GB9000305D0 (en) * 1990-01-06 1990-03-07 Pfizer Ltd Anticholinergic agents
US8188301B2 (en) 2007-06-05 2012-05-29 Nsab, Filial Af Neurosearch Sweden Ab, Sverige Disubstituted phenylpyrrolidines as modulators of cortical catecholaminergic neurotransmission

Also Published As

Publication number Publication date
NL6714553A (en) 1968-05-08
IL28811A (en) 1971-07-28
AT272331B (en) 1969-07-10
DK133942B (en) 1976-08-16
GB1202747A (en) 1970-08-19
CH511834A (en) 1971-08-31
DE1695652A1 (en) 1971-04-29
CA955936A (en) 1974-10-08
SE315594B (en) 1969-10-06
DK133942C (en) 1977-01-24
BE704683A (en) 1968-02-15
FR1575543A (en) 1969-07-25
FR7535M (en) 1969-12-22

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