US3332956A - Substituted 3, 4-dihydro-3-phenyl-4-hydroxy-4-{[(amino)alkoxy (or alkylthio)]phenyl}isothiochroman - Google Patents
Substituted 3, 4-dihydro-3-phenyl-4-hydroxy-4-{[(amino)alkoxy (or alkylthio)]phenyl}isothiochroman Download PDFInfo
- Publication number
- US3332956A US3332956A US391789A US39178964A US3332956A US 3332956 A US3332956 A US 3332956A US 391789 A US391789 A US 391789A US 39178964 A US39178964 A US 39178964A US 3332956 A US3332956 A US 3332956A
- Authority
- US
- United States
- Prior art keywords
- phenyl
- acid
- chloride
- toluenethiol
- bromo
- 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 - Lifetime
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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
Definitions
- This invention relates to novel compounds. More particularly, this invention relates to novel compounds which possess valuable utility as oral antifertility agents, and relates to intermediates useful in the preparation thereof. In another aspect, this invention relates to a novel method of inhibiting pregnancy.
- n is a whole integer from 1 to 6 inclusive;
- R R R and R each represent a member selected from the group consisting of hydrogen, chloro, bromo, iodo, fluoro, trifiuoromethyl, (lower)alkyl, (lower) al-koxy, di(lower)alkylamino, di(lower)alkylsulfamyl, (lower) alkanoyl, phenyl, phenoxy, benzyl and cycloalkyl radicals having from 5 to 7 carbon atoms inclusive, e.g. cyclopentyl, cyclohexyl and cycloheptyl;
- R and R each represent a member selected from the group consisting of (lower)alkyl, (lower)a1kenyl, (lower) alkyny1, phenyl, phenyl(lower)alkyl, cycloalkyl radicals having from 3 to 7 carbon atoms inclusive, e.g.
- 1,2,5,6- tetrahydropyridino 1,2,5,6- tetrahydropyridino, (lower)alkyltetrahydropyridino, di- (lower) alkyltetrahydropyridino, N (lower)alkylpiperazino, N'-(lower) a1kyl(lower)alkylpiperazino, N-(lower)alkyl di(lower)alkylpiperazino, hexarnethyleneimino, (lower) a1kylhexamethyleneimino, di (lower) alkylhexamethyleneimino;
- X is a member selected from the group consisting of oxygen and sulfur.
- the pharmaceutically acceptable nontoxic salts include the organic and inorganic acid addition salts, e.g., those prepared from acids such as hydrochloric, sulfuric, sulfamic, tartaric, fumaric, hydrobromic, hydriodic, glycolic, citric, maleic, phosphoric, succinic, acetic, nitric and the like.
- (lower)alkyl as used herein means both straight and branched chain alkyl radicals containing from 1 to 8 carbon atoms, e.g. methyl, ethyl, propyl, isopropyl, butyl, iso'butyl, t-butyl, amyl, hexyl, 2-et-hylhexyl, etc.
- (lower)alkenyl as used herein means both straight and branched chain alkenyl radicals containing from 2 to 8 carbon atoms, e.g. ethenyl, allyl, l-propenyl, l-butenyl, 3-butenyl, 2-methyl-1-propenyl, 3-pentenyl, 1- hexenyl, 7-octenyl, etc.
- (lower)alkynyl as used herein means both straight and branched chain alkynyl radicals containing from 2 to 8 carbon atoms, e.g. ethinyl, propargyl, 1- butinyl, 2-butinyl, 1,1-dimethylpropargyl, l-pentinyl, 1- heptinyl, etc.
- (lower) is used as part of the description of another group, e.g., (lower)alkoxy, it refers to the alkyl portion of such group which is therefore as described in connection with (lower)alkyl.
- Preferred compounds of the present invention are those having the following formulae wherein n, R R R R R and R are as represented above.
- Still more preferred compounds of the present invention are those having the following formulae herein n, R R R and R are as represented above.
- the compounds of this invention are valuable pharma- :utical agents. They possess antifertility activity and e orally active antifertility agents in mammals.
- mice The antifertility tests of the compounds of the present .vention were carried out on mice.
- the compounds were lministered oral-1y to adult female mice for six days. single dose was administered three days before mating id single doses were administered daily for five days iring mating.
- the mice were sacrificed on the eleventh ry following mating and their uteri examined for imantation sites. The absence of implantation sites in the eri indicated that pregnancy was completely inhibited.
- the preferred compound of the prestt invention 3,4-dihydro-7-methoxy-3-phenyl-4-hydroxy- ⁇ p-[2-(l-pyrrolidyl)ethoxy]phenyl ⁇ -1H-2 benzothio- 'ran hydrochloride, was administered orally at doses as w as 0.1 mgm./kg./ day, no implantation sites were obrved in any of the mice tested; hence pregnancy was tmpletely inhibited in each of the mice.
- the compounds of the present invention are prepared I the following series of reactions.
- a benzyl halide of the formula CH Hal herein R and R are as described above, and Hal is loro, brorno or iodo, is reacted with thiourea in the esence of an inert solvent, such as ethanol, at reflux rnperature, and then the mixture is heated at reflux temrature in the presence of a base, such as sodium hyoxide, to produce a toluenethiol of the formula rking the compounds of Formula X is described in chters Organic Chemistry, vol. III, 3rd Edition, at p.
- Step A The toluenethiol prepared in Step A is reacted with u-halophenylacetic acid of the formula I) (II) R HOG-(EH- 2S Hal R4 terein Hal, R and R are as described above, in the :sence of a base such as sodium hydroxide and an inert solvent such as ethanol at reflux temperature to produce a benzylthiophenylacetic acid of the formula (XII) (H) HOC ⁇ R4 R2 CH1 wherein R R R and R are as described above.
- a base such as sodium hydroxide
- an inert solvent such as ethanol
- the benzylthiophenylacetic acid prepared in Step B is cyclized by first reacting the compound with thionyl chloride in the presence of benzene at reflux temperature to convert the benzylthiophenylacetic acid to a benzylthiophenylacetyl chloride and then reacting the chloride with a dehydrating agent (Lewis acid), such as stannic chloride at a temperature of about 0 C. to produce a 3-phenyl-4-isothiochromanone of the formula (XIII) I? /C ⁇ R I CH g R /S R4 on,
- R R R and R are as described above.
- the compounds of the present invention are prepared by the reaction of the 3-phenyl-4-isothiochromanone prepared in Step C with a Grignard reagent of the formula 1 (XIV) R Ra wherein Hal, n, X, R and R are as described above.
- the reaction is preferably carried out in the presence of an inert solvent, e.g. tetrahydrofuran, and at the boiling point of the reaction mixture.
- the compounds of the present invention may be prepared by the reaction of the 3-phenyl-4-isothiochromanone with an organo-lithium compound of the formula (X V) R wherein n, X, R and R are as represented above.
- the starting materials used in the processes described herein are compounds which are either commercially available, well-known in the art, or easily prepared in accordance with standard organic procedures previously described in the chemical literature.
- the benzyl halides used in Step A are prepared by the halogenation of a benzyl alcohol of the formula (XVI) CHaOH wherein R and R are as described above, with a hydrogen halide gas, e.g., hydrogen chloride, in the presence of an inert solvent such as ethyl ether.
- a hydrogen halide gas e.g., hydrogen chloride
- An alternate method of preparing the benzyl halides consists of reacting a benzyl alcohol with thionyl chloride in the presence of pyridine. Methods for the preparation of benzyl halides are described by L. A. Brooks and H. R. Snyder, Org. Syn., coll. vol. 3, p. 698; Tsukamoto et al., Pharm.
- the Grignard reagents having the Formula XIV used in Step D are prepared by procedures well-known in the art.
- the reagents are prepared by the reaction of mag nesium with a halo-benzene of the formula 5 (XVII) /R X-o..Hi..-N
- Hal R wherein Hal, X, n, R and R are as described above, in the presence of an inert solvent, e.g., tetrahydrofuran.
- an inert solvent e.g., tetrahydrofuran.
- the halobenzenes of Formula XVII used in the preparation of the Grignard reagents are prepared by well-known procedures, e.g. cf. A. Burger, E. L. Wilson, C. O. Brindley and F. Bernheim, J. Am. Chem. Soc., vol. 67, pp. 1416-1419 (1945); and South African Patent No.
- the tertiary aminoalkanols can also be prepared by heating a secondary amine of Formula XIX with a halo alkanoic acid ester and then reducing the aminoalkanoic acid ester thus formed with a reducing agent such as lithium aluminum hydride, as described by Mofiett.
- a reducing agent such as lithium aluminum hydride
- the compounds of this invention may be administered as the free bases or in the form of their nontoxic addition salts. They may be compounded and formulated into pharmaceutical preparations in unit dosage form for oral administration with organic or inorganic solid materials or liquids which are pharmaceutically acceptable carriers.
- the compositions may take the form of tablets, powder granules, capsules, suspensions, solutions and the like. Such compositions are considered within the scope of this invention.
- compositions of this invention when administered orally, in an effective amount, are effective in the inhibition of pregnancy.
- the usual daily dosage is from about 0.1 to 200 mgm./kg.
- the material was characterized as the hydrated sodium salt, M.P. 93-95 C. (dioxane-ether).
- the crude acid chloride thus obtained was dissolve in benzene (100 ml.) and the solution stirred at 0-5 C. while a solution of stannic chloride (18.8 ml.) i1 benzene (48 ml.) was added over a 15-minute period The mixture was stirred at 0 C. for an additional 1 minutes, then poured onto a mixture of concentrate hydrochloric acid ml.) and ice.
- Trituration gave brown solid which was extracted int ether.
- the ether was washed in succession with watei aqueous sodium bicarbonate, water and saturated brin solution. After drying, the ether solution was stirred wit decolorizing carbon for 1.5 hours. Filtration and evapore tion of the ether gave a syrup which was triturated unde Skellysolve B to give brown crystalline solid, yiel 22.5 gm. (76%), M.P. 7073 C.
- a-toluenethiol 2-methoxy-a-toluenethiol, 4-m6thOXY-oc-t0lll6l16th10l, 2,4-dimethoxy-a-toluenethiol, 3,5 -dimethoxy-a-toluenethiol, 2,3-dimethoxy-rx-toluenethiol, 3,4-dimethoxya-toluenethiol, 3 -ethoxy-a-toluenethiol, 3-propoxy-u-toluenethiol, 3-chloro-a-tol-uenethiol, 3-methyl-a-toluenethiol, 4-ethyl-u-toluenethiol, 2,4-dimethyl-ot-toluenethiol, 2-propyl-ot-toluenethiol, 3-trifluoromethyl-m-tolu
- benzylthiophenylacetic acid (Z-methoxybenzylthio phenylacetic acid, (4-methoxybenzylthio phenylacetic acid, (2,4-dimethoxybenzy1thio phenyl acetic acid, (3 ,5 -dimethoxybenzylthio phenylacetic acid, (2,3-dirnethoxybenzylthio phenylacetic acid, (3 ,4-dimethoxybenzylthio phenylacetic acid, (3-ethoxybenzylthio phenylacetic acid, (3-pr0poxybenzylthio phenylacetic acid, (3 -chlorobenzylthio phenylacetic acid, (3 -m ethylb enzylthio phenylacetic acid, (4-ethylbenzylthio phenylacetic acid, (2,4-dimethylbenzylthio phenylacetic acid, (2-propylbenzylthi
- a-bromo-4-dimethylamiuophenylacetic acid a-bromo-3-diethylamin0pheny1acetic acid, a-bromo-4-fiuorophenylacetic acid, a-brom0-4-chloropheny1acetic acid, a-bromo-2-diethylaminophenylacetic acid, a-bromo-3-cycloheptylphenylacetic acid, wbromo-4-bromophenylacetic acid and a-bromo-3-propanoylphenylacetic acid,
- R R R and R each represent a member selected from the group consisting of hydrogen, chloro, bromo, iodo, fluoro, trifluoromethyl, (lower)alkyl, (lower) alkoxy, di (lower) alkylamino, di (lower) alkylsulfamyl, (lower)alkanoy1, phenyl, phenoxy, benzyl and cycloalkyl radicals having from 5 to 7 carbon atoms inclusive;
- R and R each represent a member selected from the group consisting of (lower)alkyl, (lower) alkenyl, (lower)alkynyl, phenyl, phenyl(lower)alkyl, cyclo alkyl radicals having from 3 to 7 carbon atoms inclusive, and when taken together with -N constitute a heterocyclic ring selected from the group consisting of pyrrolidino, (lower)alkylpyrrolidino, di(lower) alkylpyrrolidino, piperidino, (lower) alkylpiperidino, di(lower)alkylpiperidino, morpholino, (lower) alkylmorpholino, di(lower) alkylmorpholino, tetrahydropyridino, (lower)alkyltetrahydropyridino, di (lower) alkyltetrahydropyridino, N'- (lower) alkylpiperazino,
- X is a member selected from the group consisting of oxygen and sulfur
- n is a whole integer from 1 to 6 inclusive;
- R R R and R each represent a member selected from the group consisting of hydrogen, chloro, bromo, iodo, fluoro, trifiuoromethyl, (l-ower)alkyl, (lower) alkoxy, di(lower)alkylamino, di(lower)alkylsulfamyl, (lower) alkanoyl, phenyl, phenoxy, benzyl and cycloalkyl radicals having from 5 to 7 carbon atoms inclusive;
- R and R each represent a member selected from the group consisting of (lower) alkyl, (lower)alkenyl, lower) alkynyl, phenyl, phenyl(lower)alkyl, cycloalkyl radicals having from 3 to 7 carbon atoms inclusive, and when taken together with N constitute a heterocyclic ring selected from the group consisting of pyrrolidino, (lower)alkylpyrrolidino, di(lower)alkylpyrrolidino, piperidino, (lower)alkylpiperidino, di(lower)alkylpiperidino, morpholino, (lower) alkylmorpholino, di (lower) alkylmorpholino, tetrahydropyridino, (lower) alkyltetrahydropyridino, di(lower) alkyltetrahydropyridino, N'- (lower) alkyl piperazino, N
- n is a whole integer from 1 to 6 inclusive;
- R R R and R each represent a member selected from the group consisting of hydrogen, chloro, bromo, iodo, fluoro, trifiuoromethyl, (lower)alkyl, (lower) alkoxy, di(lower) alkylamino, di(lower) alkylsulfamyl, (lower) alkanoyl, phenyl, phenoxy, benzyl and cycloalkyl radicals having from 5 to 7 carbon atoms inclusive;
- R and R each represent a member selected from the group consisting of (lower) alkyl, (lower) alkenyl, (lower)alkynyl, phenyl, phenyl(lower) alkyl, cycloalkyl radicals having from 3 to 7 carbon atoms inclusive, and when taken together with N constitute a heterocyclic ring selected from the group consisting of pyrrolidino, (lower)alkylpyrrolidino, di(lower)alkylpyrrolidino, piperidino, (lower)alkylpiperidino, di(lower)alkylpiperidino, morpholino, (lower) alkylmorpholino, di lower) alkylmorpholino, tetrahydropyridino, (lower)alkyltetrahydropyridino, di (lower) alkyltetrahydropyridino, N'- (lower) alkylpiperazino, N'-(
- the compound having the formula /CHzCHa HO @OCH2CH2N ⁇ CH3CH3 CHaO S References Cited UNITED STATES PATENTS 3,164,607 1/1965 Lednicer 260-326.5
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- 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)
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL129204D NL129204C (da) | 1964-08-24 | ||
US391789A US3332956A (en) | 1964-08-24 | 1964-08-24 | Substituted 3, 4-dihydro-3-phenyl-4-hydroxy-4-{[(amino)alkoxy (or alkylthio)]phenyl}isothiochroman |
IL24146A IL24146A (en) | 1964-08-24 | 1965-08-12 | Substituted 3,4-dihydro-2-benzothiopyrans and a process for their production |
DK422465AA DK123656B (da) | 1964-08-24 | 1965-08-18 | Basisk substituerede 3,4-dihydro-2-benzothiopyraner eller salte deraf til anvendelse i midler med svangerskabshindrende virkning. |
SE10924/65A SE311369B (da) | 1964-08-24 | 1965-08-20 | |
DE19651545611 DE1545611A1 (de) | 1964-08-24 | 1965-08-20 | Neue substituierte 3,4-Dihydro-2-Benzo-thiopyrane und Verfahren zu deren Herstellung |
GB36125/65A GB1124102A (en) | 1964-08-24 | 1965-08-23 | Substituted 3,4-dihydro-2-benzothiopyrans and a process for the preparation thereof |
NL6510990A NL6510990A (da) | 1964-08-24 | 1965-08-23 | |
FR29287A FR1468771A (fr) | 1964-08-24 | 1965-08-24 | Procédé de fabrication de 3, 4-dihydro-2-benzothiopyrannes substitués |
BE668725A BE668725A (da) | 1964-08-24 | 1965-08-24 | |
CH1189065A CH472419A (de) | 1964-08-24 | 1965-08-24 | Verfahren zur Herstellung von substituierten 3,4-Dihydro-2-benzothio-pyranen |
ES0316769A ES316769A1 (es) | 1964-08-24 | 1965-08-24 | Un procedimiento para la preparacion de 3,4-dihidro-2-benzotiopiranos sustituidos. |
FI652013A FI45758C (fi) | 1964-08-24 | 1965-08-24 | Menetelmä 3,4-dihydro-2-bentsotiopyraanien valmistamiseksi, joita käyt etään hedelmöittymisen ehkäisyaineina. |
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 |
---|---|
US3332956A true US3332956A (en) | 1967-07-25 |
Family
ID=23547960
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US391789A Expired - Lifetime US3332956A (en) | 1964-08-24 | 1964-08-24 | Substituted 3, 4-dihydro-3-phenyl-4-hydroxy-4-{[(amino)alkoxy (or alkylthio)]phenyl}isothiochroman |
Country Status (11)
Country | Link |
---|---|
US (1) | US3332956A (da) |
BE (1) | BE668725A (da) |
CH (1) | CH472419A (da) |
DE (1) | DE1545611A1 (da) |
DK (1) | DK123656B (da) |
ES (1) | ES316769A1 (da) |
FI (1) | FI45758C (da) |
GB (1) | GB1124102A (da) |
IL (1) | IL24146A (da) |
NL (2) | NL6510990A (da) |
SE (1) | SE311369B (da) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3519629A (en) * | 1967-04-28 | 1970-07-07 | Mcneilab Inc | Piperazinomethyl-2,3-dihydro-5(pyridyl)-1-benzothiepins |
Citations (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/da unknown
- 1965-08-20 DE DE19651545611 patent/DE1545611A1/de active Pending
- 1965-08-20 SE SE10924/65A patent/SE311369B/xx unknown
- 1965-08-23 GB GB36125/65A patent/GB1124102A/en not_active Expired
- 1965-08-23 NL NL6510990A patent/NL6510990A/xx unknown
- 1965-08-24 FI FI652013A patent/FI45758C/fi active
- 1965-08-24 CH CH1189065A patent/CH472419A/de not_active IP Right Cessation
- 1965-08-24 ES ES0316769A patent/ES316769A1/es not_active Expired
- 1965-08-24 BE BE668725A patent/BE668725A/xx unknown
Patent Citations (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 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3519629A (en) * | 1967-04-28 | 1970-07-07 | Mcneilab Inc | Piperazinomethyl-2,3-dihydro-5(pyridyl)-1-benzothiepins |
US3520891A (en) * | 1967-04-28 | 1970-07-21 | Mcneilab Inc | Piperazinomethyl 2,3 dihydro 5 phenyl 1-benzothiepins |
Also Published As
Publication number | Publication date |
---|---|
FI45758C (fi) | 1972-09-11 |
NL6510990A (da) | 1966-02-25 |
DK123656B (da) | 1972-07-17 |
NL129204C (da) | |
DE1545611A1 (de) | 1969-08-07 |
CH472419A (de) | 1969-05-15 |
GB1124102A (en) | 1968-08-21 |
ES316769A1 (es) | 1966-03-16 |
FI45758B (da) | 1972-05-31 |
BE668725A (da) | 1966-02-24 |
SE311369B (da) | 1969-06-09 |
IL24146A (en) | 1969-06-25 |
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