GB1428431A - Pyrazolidinones - Google Patents

Pyrazolidinones

Info

Publication number
GB1428431A
GB1428431A GB2217773A GB2217773A GB1428431A GB 1428431 A GB1428431 A GB 1428431A GB 2217773 A GB2217773 A GB 2217773A GB 2217773 A GB2217773 A GB 2217773A GB 1428431 A GB1428431 A GB 1428431A
Authority
GB
United Kingdom
Prior art keywords
pyrazolidinones
formula
substituted
pyrazolidinone
esters
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
GB2217773A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1428431A publication Critical patent/GB1428431A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/04—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D231/08—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen or sulfur atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems

Landscapes

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

Abstract

1428431 Pyrazolidinones E I DU PONT DE NEMOURS & CO 9 May 1973 [10 May 1972 28 Feb 1973] 22177/73 Heading C2C [Also in Division C3] The invention comprises pyrazolidinones of the Formula I wherein A is CH = CH or C # C, R is H, C 1 -C 2 alkyl or C 3 -C 12 cycloalkyl, m is 0 or 1, n is 0 to 6, p is 0 to 6 and Y and Z are O or H 2 , with the proviso that when one is O the other is H 2 , and the alkali metal and amine salts thereof when R is H. The compounds of the above formula in which Z is O and Y is H 2 are prepared by reacting vinyl ketones of the formula CH 2 =CH CO(CH 2 )pCH 3 with 1-substituted 3- pyrazolidinones, reducing the oxo group in the resulting 1-substituted-2-(3-oxoalkyl)-3-pyrazolidinone, removing the blocking group at position 1, in the 1-substituted-2-(3-hydroxyalkyl)-3-pyrazolidinones thus formed, reacting the resulting 2 - (3 - hydroxyalkyl) - 3 - pyrazolidinones with esters of the formula wherein X is Cl, Br or I and R<SP>1</SP> is a group removable by hydrolysis, and if desired hydrolysing the esters so obtained. Compounds of the Formula I above in which Y is O and Z is H 2 are obtained by reacting esters of the formula XCH 2 (A) m (CH 2 ) n CO 2 R<SP>1</SP> with 1-substituted-3-pyrazolidinones, removing the substituent at the 1-position in the resulting 1- substituted-2-T-3-pyrazolidinones, when T is CH 2 (A) m (CH 2 ) n CO 2 R<SP>1</SP>, reacting the 2-T-3- pyrazolidinones with ketones of the formulµ CH 2 = CHCO(CH 2 ) p CH 3 or reducing the oxo group in the 1-[3-oxo-alkyl (or alkenyl)] - 2 - T - 3 - pyrazolidinones thus obtained, and hydrogenating the resulting 1 - [3 - hydroxyalkenyl] - 2 - T - 3 - pyrazolidinones, and, if desired, hydrolysing the esters so obtained. The following compounds are also prepared; 1-octyn-3-one, 1-octyn-3-ol, 1-octen-3-one, 1- octen-3-ol, 1-decen-3-one, 1-decen-3-ol, tert.- butyl 7 - [3 - oxo - 1 - (p - chlorophenylthiocarbamoyl) - 2 - pyrazolidinyl] - heptanoate, 2 - (3 - hydroxyoctyl) - 1 - (p - chloro - phenylthiocarbamoyl) - 3 - pyrazolidinone, 1 - benzyloxycarbonyl - 3 - pyrazolidinone, and 1- (2,2,2 - trichloroethoxycarbonyl) - 3 - pyrazolidinone. Pharmaceutical compositions, suitable for oral, parenteral or topical administration, contain the above pyrazolidinones or salts thereof in association with pharmaceutically acceptable carriers or diluents. The compounds possess biological properties similar to or antagonistic to prostaglandins.
GB2217773A 1972-05-10 1973-05-09 Pyrazolidinones Expired GB1428431A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US25186672A 1972-05-10 1972-05-10
US33676673A 1973-02-28 1973-02-28

Publications (1)

Publication Number Publication Date
GB1428431A true GB1428431A (en) 1976-03-17

Family

ID=26941864

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2217773A Expired GB1428431A (en) 1972-05-10 1973-05-09 Pyrazolidinones

Country Status (4)

Country Link
JP (1) JPS4961164A (en)
DE (1) DE2323193A1 (en)
FR (1) FR2184064B1 (en)
GB (1) GB1428431A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0003410A1 (en) * 1978-01-23 1979-08-08 Beecham Group Plc Hydantoins and thiohydantoins, method for their preparation and pharmaceutical compositions containing them
WO2003035064A1 (en) * 2001-10-23 2003-05-01 Applied Research Systems Ars Holding N.V. Pyrazolidinone compounds as ligands of the prostaglandin ep2 and/or ep4 receptors

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL53559A0 (en) 1976-12-18 1978-03-10 Beecham Group Ltd Novel prostaglandin analogues their preparation and pharmaceutical compositions containing them
EP0007180B1 (en) * 1978-06-15 1983-03-30 Beecham Group Plc Prostaglandin analogue triazole derivatives, processes for their preparation and a pharmaceutical composition containing them
AU4778279A (en) * 1978-06-15 1979-12-20 Beecham Group Limited Prostaglandin analogues
IL57504A0 (en) * 1978-06-15 1979-10-31 Beecham Group Ltd Prostagandin analogues,their preparation and pharmaceutical compositions containing
AU4806879A (en) * 1978-06-15 1979-12-20 Beecham Group Limited 1,2,4 triazole derivatives
US4211876A (en) 1979-06-13 1980-07-08 E. I. Du Pont De Nemours And Company 3-Pyrazolidinone carboxamides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0003410A1 (en) * 1978-01-23 1979-08-08 Beecham Group Plc Hydantoins and thiohydantoins, method for their preparation and pharmaceutical compositions containing them
WO2003035064A1 (en) * 2001-10-23 2003-05-01 Applied Research Systems Ars Holding N.V. Pyrazolidinone compounds as ligands of the prostaglandin ep2 and/or ep4 receptors
AU2002340282B2 (en) * 2001-10-23 2007-08-09 Merck Serono Sa Pyrazolidinone compounds as ligands of the prostaglandin EP2 and/or EP4 receptors
US7410991B2 (en) 2001-10-23 2008-08-12 Laboratoires Serono S.A. Pyrazolidinone compounds as ligands of the prostaglandin EP2 and/or EP4 receptors
US7863312B2 (en) 2001-10-23 2011-01-04 Merck Serono Sa Pyrazolidinone compounds as ligands of the prostaglandin EP2 and/or EP4 receptors

Also Published As

Publication number Publication date
DE2323193A1 (en) 1973-11-22
FR2184064B1 (en) 1977-04-22
FR2184064A1 (en) 1973-12-21
JPS4961164A (en) 1974-06-13

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee