GB931555A - Dibenzocycloheptatriene derivatives - Google Patents

Dibenzocycloheptatriene derivatives

Info

Publication number
GB931555A
GB931555A GB29490/59A GB2949059A GB931555A GB 931555 A GB931555 A GB 931555A GB 29490/59 A GB29490/59 A GB 29490/59A GB 2949059 A GB2949059 A GB 2949059A GB 931555 A GB931555 A GB 931555A
Authority
GB
United Kingdom
Prior art keywords
compounds
cycloheptatrien
reacting
prepared
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
GB29490/59A
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.)
Merck and Co Inc
Original Assignee
Merck and Co 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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27117345&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=GB931555(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB931555A publication Critical patent/GB931555A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/12—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with only hydrogen atoms attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms

Abstract

The invention comprises compounds of the general formula <FORM:0931555/IV(a)/1> and the corresponding 10,11-dihydro analogues, in which X and X1 are hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy or mononuclear aryl, there being one or more such atom or group in each ring, and R is hydrogen C1-4 alkyl, C2-4 alkenyl, or their hydroxy, mesyloxy and amino substituted derivatives and derivatives alkylated in one or more of positions 2, 3, 5 and 6 of the piperidine ring so that the total number of carbon atoms in all such substituent alkyl groups does not exceed four, their acid addition salts and N-oxides; the preparation thereof by dehydrating a compound of the formula <FORM:0931555/IV(a)/2> or the 10,11-dihydro analogue thereof, or by reacting a ketone of the formula <FORM:0931555/IV(a)/3> or its 10,11-dihydro analogue with a 1-R-4-piperidyl-Grignar reagent hydrolysing the adduct then dehydrating the hydroxy compound as above. Compounds wherein R is hydrogen are also prepared by reacting the 1-methyl-4-(5-dibenzo [a,e] cycloheptatrienylidene)-piperidine with cyanogen bromide and hydrolysing the 1-cyanomethyl-4-(5-dibenzo [a,e] cycloheptatrienylidene)- piperidine so formed. Compounds where R is alkyl, alkenyl or aminoalkyl are also prepared by reacting a 4-(5-dibenzo [a,e] cycloheptatrienylidene)-piperidine with an alkyl, alkenyl or aminoalkyl halide in the presence of a basic condensation agent, and where R is hydroxyalkyl and mesyloxyalkyl by reacting the N-substituted compounds with ethylene oxide to give the N-hydroxyalkyl derivatives and esterifying these with methylsulphonic anhydride. 3-Fluorodibenzo [a,e] cycloheptatrien-5-one is obtained by reacting p-fluoro-phenylacetic acid with phthalic anhydride, reducing the phthalide to the fluorophenethylbenzoic acid, cyclizing the last named compound, and forming the 10,11-double bond by bromination and dehydrobromination. Similarly is prepared 3-methoxydibenzo [a,e] cycloheptatrien-5-one through 3-(p-methoxybenzylidene)-phthalide and 2-(p-methoxyphenethyl) benzoic acid. 1-Bromodibenzo [a,e] cycloheptatrien-5-one is prepared by treating 2-(o-bromophenethyl)-aniline according to the Sandmeyer reaction to form 2-(o-bromophenethyl) cyanide, hydrolysing this to 2-(o-bromophenethyl)-benzoic acid, cyclising the acid, and forming the 10,11-double bond. 3,7-Dichlorodibenzo [a,e] cycloheptatrien-5-one is prepared by reducing 3,7-dinitrodibenzo [a,e] cycloheptatrien-5-one to the 3,7-diamino-compound and replacing the amino groups by chlorine atoms according to the Sandmeyer reaction. Pharmaceutical compositions comprise the compounds of the invention in oral forms such as tablets, capsules, powders, elixirs and aqueous suspensions or in sterile solutions for injection. The compounds possess antiserotonin and antihistamine activity. Specification 931,556 is referred to.
GB29490/59A 1958-09-29 1959-08-28 Dibenzocycloheptatriene derivatives Expired GB931555A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US76380958A 1958-09-29 1958-09-29
US826493A US3014911A (en) 1958-09-29 1959-07-13 Derivatives of dibenzo[a, e]cycloheptatriene

Publications (1)

Publication Number Publication Date
GB931555A true GB931555A (en) 1963-07-17

Family

ID=27117345

Family Applications (2)

Application Number Title Priority Date Filing Date
GB7308/63A Expired GB931556A (en) 1958-09-29 1959-08-28 Dibenzocycloheptatriene derivatives
GB29490/59A Expired GB931555A (en) 1958-09-29 1959-08-28 Dibenzocycloheptatriene derivatives

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB7308/63A Expired GB931556A (en) 1958-09-29 1959-08-28 Dibenzocycloheptatriene derivatives

Country Status (8)

Country Link
US (1) US3014911A (en)
BE (1) BE582220A (en)
CH (1) CH387037A (en)
DE (1) DE1420072C3 (en)
FR (1) FR490M (en)
GB (2) GB931556A (en)
MY (1) MY6400051A (en)
OA (1) OA00998A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5250681A (en) * 1988-06-02 1993-10-05 Ajinomoto Co., Inc. Piperidine derivatives and hypotensives containing the same

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US3968115A (en) * 1970-02-05 1976-07-06 Merck & Co., Inc. 1-Alkyl-4-(10 and/or 11)-bromo-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-ylidene piperidine compounds
US3981877A (en) * 1972-08-14 1976-09-21 Merck & Co., Inc. Piperidylidene derivatives of carboxy-5H-dibenzo[a,d]cycloheptene
US3988342A (en) * 1972-08-14 1976-10-26 Merck & Co., Inc. Piperidylidene derivatives of cyano-5H-dibenzo[a,d]cycloheptene
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GB1435054A (en) * 1974-02-04 1976-05-12 Ici Ltd Dihydroanthracene derivatives
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5250681A (en) * 1988-06-02 1993-10-05 Ajinomoto Co., Inc. Piperidine derivatives and hypotensives containing the same

Also Published As

Publication number Publication date
OA00998A (en) 1968-08-07
DE1420072B2 (en) 1974-01-03
BE582220A (en) 1960-03-01
CH387037A (en) 1965-01-31
DE1420072C3 (en) 1974-08-08
GB931556A (en) 1963-07-17
FR490M (en) 1961-05-08
MY6400051A (en) 1964-12-31
US3014911A (en) 1961-12-26
DE1420072A1 (en) 1968-10-03

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