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 thereofInfo
- 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
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.
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)
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)
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 |
-
0
- NL NL129204D patent/NL129204C/xx active
-
1964
- 1964-08-24 US US391789A patent/US3332956A/en not_active Expired - Lifetime
-
1965
- 1965-08-12 IL IL24146A patent/IL24146A/en unknown
- 1965-08-18 DK DK422465AA patent/DK123656B/en unknown
- 1965-08-20 SE SE10924/65A patent/SE311369B/xx unknown
- 1965-08-20 DE DE19651545611 patent/DE1545611A1/en active Pending
- 1965-08-23 GB GB36125/65A patent/GB1124102A/en not_active Expired
- 1965-08-23 NL NL6510990A patent/NL6510990A/xx unknown
- 1965-08-24 BE BE668725A patent/BE668725A/xx unknown
- 1965-08-24 FI FI652013A patent/FI45758C/en active
- 1965-08-24 ES ES0316769A patent/ES316769A1/en not_active Expired
- 1965-08-24 CH CH1189065A patent/CH472419A/en not_active IP Right Cessation
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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