GB1489486A - Esters of thienobenzopyrans and thiopyrano benzopyrans - Google Patents

Esters of thienobenzopyrans and thiopyrano benzopyrans

Info

Publication number
GB1489486A
GB1489486A GB9212/75A GB921275A GB1489486A GB 1489486 A GB1489486 A GB 1489486A GB 9212/75 A GB9212/75 A GB 9212/75A GB 921275 A GB921275 A GB 921275A GB 1489486 A GB1489486 A GB 1489486A
Authority
GB
United Kingdom
Prior art keywords
methyl
alkyl
prepared
ethyl
carboxylate
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
GB9212/75A
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.)
Individual
Original Assignee
Individual
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 US05/448,401 external-priority patent/US3960871A/en
Application filed by Individual filed Critical Individual
Publication of GB1489486A publication Critical patent/GB1489486A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1489486 Esters of thienobenzopyrans and thiopyranobenzopyrans L S HARRIS H G PARS J C SHEEHAN and R K RAZDAN 5 March 1975 [5 March 1974] 9212/75 Addition to 1386027 Heading C2C Novel compounds of the Formula I wherein n is 0 to 3, m is 0-3 provided m + n is 2 or 3, R 1 is alkyl, R 2 is C 1-20 alkyl, C 3-8 cycloalkylalkyl or alkylcycloalkylalkyl, R 4 is hydrogen or alkyl, R 5 is hydrogen or alkyl and R 3 is in which Y is C 1-8 alkylene, a is 1 to 4, b is 1 to 4, R 6 is hydrogen or alkyl and X is CH 2 , O, S or NR 7 wherein R 7 is hydrogen or alkyl with the proviso that (a) when X is O, S or NR 7 , a and b are both 2 and (b) Y is a branched chain alkylene group and/or at least one of R 4 , R 5 and R 6 is alkyl wherein cycloalkyl and alkylcycloalkyl moieties have 3 to 8 carbon atoms and alkyl groups unless otherwise specified are C 1-6 , and acid addition salts thereof may be prepared by esterification of a compound of the formula X with an acid R 3 OH or a salt thereof in the presence of a slight excess of a carbodiimide. The intermediates of the Formula X are prepared by cyclizing an appropriately substituted oxo-tetrahydrothiopyran carboxylate or oxo-tetra hydrothiophene carboxylate in which the oxo and carboxylate groups are on adjacent carbon atoms of the ring with an R 2 substituted resorcinol to form a thienobenzopyran or thiopyranobenzopyran of the Formula X in which the R 1 radicals together form an oxo group and subsequently reacting this product with an appropriate Grignard reagent. Ethyl 5 - methyl - 3 - oxo - tetrahydrothiophene-2-carboxylate is prepared by reaction of ethyl mercaptoacetate with ethyl crotonate in the presence of sodium ethoxide to yield diethyl - 4 - methyl - 3 - thiahexanediote followed by cyclization using strong base. Ethyl 5,5- dimethyl - 3 - oxo - tetrahydrothiophene - 2 - carboxylate is prepared by a similar method. Methyl 4 - methyl - 3 - oxotetrahydrothiopyran-2-carboxylate is prepared by reacting 2- methyl-4-butyrolactone with methanolic hydrogen bromide to yield methyl 4-bromo-2-methylbutyrate, followed by condensation of the product with methylmercaptoacetate in base to form methyl 4 - (methoxycarbonylmethylthio)- 2- methyl butyrate followed by cyclization using strong base to yield the required compound. 2 - Methyl - 4 - piperidinobutyric acid hydrochloride is prepared by condensation of 4- bromo-2-methyl butyrate with piperidine to yield ethyl - 2 - methyl - 4 - piperidino butyrate followed by treatment with hydrochloric acid. 2,2 - Dimethyl - 4 - piperidino butyric acid hydrochloride is prepared by reaction of 2,2- dimethyl - 4 - butyrolactone with ethanolic hydrogen bromide to yield ethyl 2,2-dimethyl-4- bromobutyrate which with piperidine yields ethyl 2,2 - dimethyl - 4 - piperidinobutyrate which yields the required compound on treatment with hydrochloric acid. Pharmaceutical compositions of the compounds I with the usual excipients show analgesic, antianxiety, tranquillizing, sedative, antidepressant, anti-convulsant and anti-psychotic activity when administered orally or parenterally.
GB9212/75A 1974-03-05 1975-03-05 Esters of thienobenzopyrans and thiopyrano benzopyrans Expired GB1489486A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/448,401 US3960871A (en) 1971-12-27 1974-03-05 Esters of thienobenzopyrans and thiopyranobenzopyrans

Publications (1)

Publication Number Publication Date
GB1489486A true GB1489486A (en) 1977-10-19

Family

ID=23780170

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9212/75A Expired GB1489486A (en) 1974-03-05 1975-03-05 Esters of thienobenzopyrans and thiopyrano benzopyrans

Country Status (4)

Country Link
DE (1) DE2509562A1 (en)
FR (1) FR2262980B2 (en)
GB (1) GB1489486A (en)
SE (1) SE422687B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2143234A (en) * 1983-07-06 1985-02-06 Shinogi Seiyaku Kabushiki Kais (oxoheterocyclic carbonamido) cephem carboxylic acid derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2143234A (en) * 1983-07-06 1985-02-06 Shinogi Seiyaku Kabushiki Kais (oxoheterocyclic carbonamido) cephem carboxylic acid derivatives

Also Published As

Publication number Publication date
DE2509562A1 (en) 1975-09-11
SE422687B (en) 1982-03-22
SE7502409L (en) 1975-09-08
FR2262980A2 (en) 1975-10-03
FR2262980B2 (en) 1982-07-16

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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