GB1490771A - 2-substituted 4,5-diphenylthiazoles and synthesis thereof - Google Patents

2-substituted 4,5-diphenylthiazoles and synthesis thereof

Info

Publication number
GB1490771A
GB1490771A GB3224/75A GB322475A GB1490771A GB 1490771 A GB1490771 A GB 1490771A GB 3224/75 A GB3224/75 A GB 3224/75A GB 322475 A GB322475 A GB 322475A GB 1490771 A GB1490771 A GB 1490771A
Authority
GB
United Kingdom
Prior art keywords
general formula
prepared
diphenyl
reacting
group
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
GB3224/75A
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.)
Serono Laboratories Inc
Original Assignee
Serono Laboratories 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 Serono Laboratories Inc filed Critical Serono Laboratories Inc
Publication of GB1490771A publication Critical patent/GB1490771A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/28—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

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

Abstract

1490771 4,5-Diphenyl-thiazoles SERONO LABORATORIES Inc 24 Jan 1975 [31 Jan 1974] 3224/75 Heading C2C Novel 4,5-diphenyl-thiazoles of the general formula wherein X is -NR 1 R 2 , each of R<SP>1</SP> and R<SP>2</SP> is a hydrogen atom or a C 1-4 alkyl, C 1-4 hydroxyalkyl, C 1-4 acyl or acyloxy-C 1-4 alkyl group or NR<SP>1</SP>R<SP>2</SP> is a 5- or 6-ring-membered heterocyclic amino group, and A is a single bond or an alkylene group, and acid addition salts and N- acylated derivatives thereof are prepared (a) by cyclizing with P 2 S 5 an α-phenylacetophenone derivative of the general formula wherein X is -NR<SP>1</SP>R<SP>2</SP>; (b) by reacting a halide of the general formula wherein Hal is a halogen atom, with HNR<SP>1</SP>R<SP>2</SP>; and (c) when at least one of R<SP>1</SP> and R<SP>2</SP> is a C 1-4 acyl or acyloxy-C 1-4 alkyl group, by acylating the corresponding compound in which at least one of R<SP>1</SP> and R<SP>2</SP> is a hydrogen atom or C 1-4 hydroxyalkyl group; followed optionally by salification or N-acylation of the product. α-Phenylacetophenone derivatives of the second general formula above are prepared by reacting the corresponding compound in which X is a halogen atom (itself prepared by reacting desylamine with Hal-CO-A-X) with HNR<SP>1</SP>R<SP>2</SP> Halides of the third general formula above wherein A is an alkylene group are prepared analogously to process (a) above. Pharmaceutical compositions having hypocholesterolemic and/or platelet aggregationinhibiting activity comprise, as active ingredient, a 4,5-diphenyl-thiazole of the first general formula above or a pharmaceutically acceptable acid addition salt or N-acylated derivative thereof, together with a pharmaceutically acceptable diluent, carrier or excipient.
GB3224/75A 1974-01-31 1975-01-24 2-substituted 4,5-diphenylthiazoles and synthesis thereof Expired GB1490771A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH137774A CH587836A5 (en) 1974-01-31 1974-01-31

Publications (1)

Publication Number Publication Date
GB1490771A true GB1490771A (en) 1977-11-02

Family

ID=4208998

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3224/75A Expired GB1490771A (en) 1974-01-31 1975-01-24 2-substituted 4,5-diphenylthiazoles and synthesis thereof

Country Status (15)

Country Link
JP (1) JPS50121269A (en)
AT (1) AT339898B (en)
BE (1) BE825097A (en)
CA (1) CA1036600A (en)
CH (1) CH587836A5 (en)
DE (1) DE2503436A1 (en)
DK (1) DK33175A (en)
ES (1) ES434151A1 (en)
FR (1) FR2259603B1 (en)
GB (1) GB1490771A (en)
IL (1) IL46476A (en)
NL (1) NL7501086A (en)
NO (1) NO750278L (en)
SE (1) SE7501010L (en)
ZA (1) ZA75494B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0388909A2 (en) * 1989-03-22 1990-09-26 Fujisawa Pharmaceutical Co., Ltd. Thiazole compounds, processes for the preparation thereof and pharmaceutical composition comprising the same
AU654125B2 (en) * 1991-03-07 1994-10-27 Hisamitsu Pharmaceutical Co., Inc. Novel diphenylthyazole derivative
US8334301B2 (en) 2007-09-28 2012-12-18 Takeda Pharmaceutical Company Limited 5-Membered heterocyclic compound

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4168315A (en) * 1977-09-28 1979-09-18 The Upjohn Company Dianisyl thiazole compound, compositions and method of antithrombotic treatment
JPH0753666B2 (en) * 1987-09-14 1995-06-07 久光製薬株式会社 Anti-inflammatory agent consisting of substituted diphenylthiazole derivative
CA2515119A1 (en) 2003-02-07 2004-08-19 Daiichi Pharmaceutical Co., Ltd. Pyrazole derivative

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0388909A2 (en) * 1989-03-22 1990-09-26 Fujisawa Pharmaceutical Co., Ltd. Thiazole compounds, processes for the preparation thereof and pharmaceutical composition comprising the same
EP0388909A3 (en) * 1989-03-22 1991-05-08 Fujisawa Pharmaceutical Co., Ltd. Thiazole compounds, processes for the preparation thereof and pharmaceutical composition comprising the same
AU654125B2 (en) * 1991-03-07 1994-10-27 Hisamitsu Pharmaceutical Co., Inc. Novel diphenylthyazole derivative
US8334301B2 (en) 2007-09-28 2012-12-18 Takeda Pharmaceutical Company Limited 5-Membered heterocyclic compound

Also Published As

Publication number Publication date
IL46476A0 (en) 1975-04-25
DE2503436A1 (en) 1975-08-07
ES434151A1 (en) 1976-12-01
ATA55975A (en) 1977-03-15
NL7501086A (en) 1975-08-04
SE7501010L (en) 1975-08-01
CA1036600A (en) 1978-08-15
BE825097A (en) 1975-07-31
FR2259603A1 (en) 1975-08-29
DK33175A (en) 1975-09-29
AU7747875A (en) 1976-07-22
FR2259603B1 (en) 1978-07-21
IL46476A (en) 1978-12-17
AT339898B (en) 1977-11-10
JPS50121269A (en) 1975-09-23
ZA75494B (en) 1976-01-28
NO750278L (en) 1975-08-25
CH587836A5 (en) 1977-05-13

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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