GB1124102A - Substituted 3,4-dihydro-2-benzothiopyrans and a process for the preparation thereof - Google Patents

Substituted 3,4-dihydro-2-benzothiopyrans and a process for the preparation thereof

Info

Publication number
GB1124102A
GB1124102A GB36125/65A GB3612565A GB1124102A GB 1124102 A GB1124102 A GB 1124102A GB 36125/65 A GB36125/65 A GB 36125/65A GB 3612565 A GB3612565 A GB 3612565A GB 1124102 A GB1124102 A GB 1124102A
Authority
GB
United Kingdom
Prior art keywords
formula
compounds
acid
phenyl
alkyl
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
GB36125/65A
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.)
Bristol Myers Co
Original Assignee
Bristol Myers 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 Bristol Myers Co filed Critical Bristol Myers Co
Publication of GB1124102A publication Critical patent/GB1124102A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans

Landscapes

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

Abstract

Compounds of the general formula (I) <FORM:1124102/C2/1> (wherein n is 1-6; R1, R2, R3 and R4 are each hydrogen, chloro, bromo, iodo, fluoro, trifluoromethyl, C1- 8 alkyl, C1- 8 alkoxy, phenyl, phenoxy, benzyl or C5- 7 cycloalkyl radicals; R5 and R6 are each C1- 8 alkyl, C2- 8 alkenyl, C2- 8 alkynyl, phenyl, phenyl-(C1- 8 alkyl) or C3- 7 cycloalkyl, or when taken together with -N<, constitute a heterocyclic group; and X is oxygen or sulphur) and their acid addition salts are prepared by reacting a compound of the formula (II) <FORM:1124102/C2/2> in an inert organic solvent with about one equivalent part of a compound of the formula (III) <FORM:1124102/C2/3> (wherein Z is chloro, bromo or iodo), optionally followed by salt formation. The starting materials of formula (II) are prepared by converting a benzyl halide of the formula <FORM:1124102/C2/4> to the toluenethiol of the formula <FORM:1124102/C2/5> which is reacted with an a -halophenylacetic acid of the formula <FORM:1124102/C2/6> in the presence of a base and an inert solvent at reflux temperature to produce the benzylthiophenylacetic acid of the formula <FORM:1124102/C2/7> which is converted to the acid chloride and cyclized. a -(m-Methoxybenzylthio)phenylacetic acid is characterized as the hydrated sodium salt. The preparation of compounds of the formula <FORM:1124102/C2/8> is described; these compounds are used to prepare the starting materials of formula (III). The compounds of the invention are oral antifertility agents, and may be administered in the form of pharmaceutical preparations containing them together with a carrier.
GB36125/65A 1964-08-24 1965-08-23 Substituted 3,4-dihydro-2-benzothiopyrans and a process for the preparation thereof Expired GB1124102A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US391789A US3332956A (en) 1964-08-24 1964-08-24 Substituted 3, 4-dihydro-3-phenyl-4-hydroxy-4-{[(amino)alkoxy (or alkylthio)]phenyl}isothiochroman

Publications (1)

Publication Number Publication Date
GB1124102A true GB1124102A (en) 1968-08-21

Family

ID=23547960

Family Applications (1)

Application Number Title Priority Date Filing Date
GB36125/65A Expired GB1124102A (en) 1964-08-24 1965-08-23 Substituted 3,4-dihydro-2-benzothiopyrans and a process for the preparation thereof

Country Status (11)

Country Link
US (1) US3332956A (en)
BE (1) BE668725A (en)
CH (1) CH472419A (en)
DE (1) DE1545611A1 (en)
DK (1) DK123656B (en)
ES (1) ES316769A1 (en)
FI (1) FI45758C (en)
GB (1) GB1124102A (en)
IL (1) IL24146A (en)
NL (2) NL6510990A (en)
SE (1) SE311369B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3444176A (en) * 1967-04-28 1969-05-13 Mcneilab Inc Certain 4-diloweralkylamino-lower alkyl - 5 - pyridyl (or phenyl)-2,3-dihydro - 1 - benzothiepins and derivatives thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3164607A (en) * 1961-01-10 1965-01-05 Upjohn Co 2-phenyl-3-(tertiary amino alkoxy) phenyl-indenes

Also Published As

Publication number Publication date
ES316769A1 (en) 1966-03-16
DK123656B (en) 1972-07-17
DE1545611A1 (en) 1969-08-07
NL129204C (en)
BE668725A (en) 1966-02-24
IL24146A (en) 1969-06-25
CH472419A (en) 1969-05-15
FI45758C (en) 1972-09-11
SE311369B (en) 1969-06-09
NL6510990A (en) 1966-02-25
FI45758B (en) 1972-05-31
US3332956A (en) 1967-07-25

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