GB1323191A - Pyrrolidinylacetic acid esters - Google Patents

Pyrrolidinylacetic acid esters

Info

Publication number
GB1323191A
GB1323191A GB11471A GB11471A GB1323191A GB 1323191 A GB1323191 A GB 1323191A GB 11471 A GB11471 A GB 11471A GB 11471 A GB11471 A GB 11471A GB 1323191 A GB1323191 A GB 1323191A
Authority
GB
United Kingdom
Prior art keywords
prepared
carbomethoxy
dihydro
alkyl
pyrrole
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
GB11471A
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.)
Novartis AG
Original Assignee
Ciba Geigy 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
Priority claimed from CH56070A external-priority patent/CH523241A/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1323191A publication Critical patent/GB1323191A/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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—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 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
    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms

Landscapes

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

Abstract

1323191 Pyrrolidinylacetic acid esters CIBAGEIGY AG 1 Jan 1971 [15 Jan 1970 26 Nov 1970] 114/71 Heading C2C Novel compounds I in which R is 1-6 C alkyl, 2-6 C alkenyl, cycloalkyl or cycloalkylalkyl; Ph is optionally substituted phenyl; and A is a 2-pyrrolidinyl radical which is optionally substituted by 1-6 C alkyl or alkoxy or N-(1-6 C alkyl) or N-(2-6 C alkenyl) substituted are prepared by (1) reduction of the double bond of compounds II in which A<SP>1</SP> is a doubly bonded radical corresponding to A, or a tautomer thereof in which the double bond lies in the heterocyclic ring or (2) by conventional modification of the group X in compounds III in which X is a free or reactively modified carboxyl group different from COOR. 2 - [α - Carbomethoxy - benzylidene] - pyrrolidine is prepared by reaction of 2-thiopyrrolidone with α-bromophenylacetic acid methyl ester to give 2 - [α - carbomethoxybenzylmercapto]-4,5- dihydro-3H-pyrrole which is then reacted with trimethyl phosphite. Threo - α - phenyl - α - (2 - pyrrolidinyl) - acetic acid is prepared by alkaline hydrolysis of the diastereomer mixture of the methyl ester. 2 - [α - (Carbo - t - butoxy - p - methoxy - benzylidene]-pyrrolidine is prepared by reaction of 2- thiopyrrolidone with α - bromo - p methoxyphenylacetic acid t-butyl ester to give 2-[α- (carbo - t - butoxy) - p - methoxybenzylmercapto]- 4,5-dihydro-3H-pyrrole followed by reaction of the latter with triethyl phosphite. 2-(α-Carbomethoxy - p - methoxybenzylidene) - 3S,4S - dimethoxypyrrolidine is prepared similarly via 3R,4S - dimethoxy - 2 - (α - carbomethoxy - pmethoxybenzylmercapto) - 4,5 - dihydro - 3H- pyrrole Pharmaceutical compositions for enteral or parenteral administration as central stimulating drugs comprise a compound I together with a suitable excipient.
GB11471A 1970-01-15 1971-01-01 Pyrrolidinylacetic acid esters Expired GB1323191A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH56070A CH523241A (en) 1970-01-15 1970-01-15 Antidepressant 2-subst pyrrolidine derivs
CH1753870 1970-11-26

Publications (1)

Publication Number Publication Date
GB1323191A true GB1323191A (en) 1973-07-11

Family

ID=25684959

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11471A Expired GB1323191A (en) 1970-01-15 1971-01-01 Pyrrolidinylacetic acid esters

Country Status (9)

Country Link
AT (3) AT305272B (en)
AU (1) AU2432371A (en)
BE (1) BE761572A (en)
CA (1) CA936536A (en)
DE (1) DE2100422A1 (en)
FR (1) FR2081433A1 (en)
GB (1) GB1323191A (en)
HU (1) HU163236B (en)
NL (1) NL7100525A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3117979A1 (en) * 1981-05-07 1983-01-20 Hoechst Ag, 6000 Frankfurt NEW (DELTA) 1-PYRROLIN-THIOLACTIMAETHER AND METHOD FOR THE PRODUCTION THEREOF
CN101677546A (en) * 2007-06-22 2010-03-24 纽约州州立大学研究基金会 Substituted pyrrolidine compounds with central nervous system activity

Also Published As

Publication number Publication date
AT300778B (en) 1972-08-10
CA936536A (en) 1973-11-06
AU2432371A (en) 1972-07-20
DE2100422A1 (en) 1971-07-22
AT305271B (en) 1973-02-26
AT305272B (en) 1973-02-26
BE761572A (en) 1971-07-14
NL7100525A (en) 1971-07-19
HU163236B (en) 1973-07-28
FR2081433A1 (en) 1971-12-03

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees