GB1261693A - Benzomorphans - Google Patents

Benzomorphans

Info

Publication number
GB1261693A
GB1261693A GB2502/70A GB250270A GB1261693A GB 1261693 A GB1261693 A GB 1261693A GB 2502/70 A GB2502/70 A GB 2502/70A GB 250270 A GB250270 A GB 250270A GB 1261693 A GB1261693 A GB 1261693A
Authority
GB
United Kingdom
Prior art keywords
cycloalkyl
alkyl
quaternary
methyl
aryl
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
GB2502/70A
Inventor
Franklin Moore Robinson
Paul Stanley Anderson
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
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1261693A publication Critical patent/GB1261693A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/02—Preparation by ring-closure or hydrogenation
    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds thereof
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • C07D221/26—Benzomorphans

Abstract

1,261,693. Benzomorphans. MERCK & CO. Inc. 19 Jan., 1970 [23 Jan., 1969], No. 2502/70. Addition to 1,261,481. Heading C2C. Novel benzomorphans or their salts of the general Formula IX (wherein R 2 is hydrogen, cyano or -CH 2 R where R is hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkyl alkyl, cycloalkenyl, cycloalkenyl alkyl, alkyl cycloalkyl, alkenyl cycloalkyl, methylene cycloalkyl, alkylcycloalkenyl or spiroalkyl; R 3 is alkyl cycloalkyl, aryl, substituted aryl that is capable of forming an aryl lithium reagent or aralkyl; and R 5 is alkyl, aryl or substituted aryl provided that the substituent will not react with a lithium reagent) may be prepared by forming a quaternary with methyl halide of a 2,4-disubstituted pyridine and either reducing the quaternary to a 2,4- substituted - 1 - methyl - 1,2,3,6 - tetrahydropyridine from which a quaternary is formed with a p-methoxyl benzyl halide which is subsequently rearranged with a lithium reagent to VIII or the quaternary is reacted with p-methoxyl benzyl magnesium chloride to give a 2,4-disubstituted 1 - methyl - 6 - p - methoxyl benzyl-5,6-dihydropyridine which may be reduced with sodium borohydride to VIII, which may be cyclized with hydrobromic acid to give IX in which R 2 is methyl, the compounds IX in which R 2 is hydrogen, cyano or CH 2 R being produced by methods described in the parent. Pharmaceutical compositions of compounds I with the usual excipients show analgesic activity when administered orally or parenterally.
GB2502/70A 1969-01-23 1970-01-19 Benzomorphans Expired GB1261693A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US79357169A 1969-01-23 1969-01-23

Publications (1)

Publication Number Publication Date
GB1261693A true GB1261693A (en) 1972-01-26

Family

ID=25160225

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2502/70A Expired GB1261693A (en) 1969-01-23 1970-01-19 Benzomorphans

Country Status (7)

Country Link
US (1) US3700734A (en)
BR (1) BR6914877D0 (en)
CH (1) CH534165A (en)
DE (1) DE2002840C3 (en)
FR (1) FR2034485B1 (en)
GB (1) GB1261693A (en)
NL (1) NL7000166A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4357471A (en) 1976-12-17 1982-11-02 Rohm And Haas Company Azaspiro compounds
US4374991A (en) 1976-12-17 1983-02-22 Rohm And Haas Company 2,6-Dimethylpiperidinyl-N-carbobutoxymethyl urea
US4400512A (en) * 1976-12-17 1983-08-23 Rohm And Haas Company Azaspiro compounds
US4405630A (en) * 1980-12-29 1983-09-20 Rohm And Haas Company Arthropod repellent compositions and methods

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4161598A (en) * 1972-05-26 1979-07-17 Sterling Drug Inc. 1-Oxygenated-2,6-methano-3-benzazocines
US3966747A (en) * 1972-10-26 1976-06-29 Bristol-Myers Company 9-Hydroxy-6,7-benzomorphans
US3891657A (en) * 1972-10-26 1975-06-24 Bristol Myers Co 9Beta-hydroxy-5-methyl-6,7-benzomorphans
JPS5817190B2 (en) * 1973-03-31 1983-04-05 住友化学工業株式会社 Synquina 4,5-Dialkylbenzomorph
US3959290A (en) * 1973-07-18 1976-05-25 Bristol-Myers Company 3,14-Substituted-8-oxamorphinans
US3853889A (en) * 1973-07-18 1974-12-10 Bristol Myers Co 3,14-substituted-8-oxamorphinans
US3892757A (en) * 1973-08-29 1975-07-01 Purdue Research Foundation Trialkylmethanobenzazocinols
US3891658A (en) * 1973-08-29 1975-06-24 Purdue Research Foundation N-Phenethyl trialkylmethanobenz-azolines
US4009171A (en) * 1974-02-21 1977-02-22 Sterling Drug Inc. N-acylated-11-oxygenated-2,6-methano-3-benzazocine intermediates
DE2437610A1 (en) * 1974-08-05 1976-02-26 Boehringer Sohn Ingelheim NEW 5.9-BETA-DISUBSTITUTED 2-TETRAHYDROFURFURYL-6,7-BENZOMORPHANES, THEIR ACID-ADDITIONAL SALTS, THEIR USE AS A MEDICINAL PRODUCTS AND METHOD FOR THEIR PRODUCTION
US4022789A (en) * 1975-11-20 1977-05-10 Sterling Drug Inc. Dichlorocyclopropylmethyl-benzazocines
US4205171A (en) * 1976-01-12 1980-05-27 Sterling Drug Inc. Aminomethanobenzazocines and nitromethanobenzazocines
US4341904A (en) * 1980-02-19 1982-07-27 Merck & Co., Inc. Derivatives of 2-hydroxy-6,9-methano-11-amino-5,6,7,8,9,10-hexahydro-benzocyclooctene
US4332807A (en) * 1981-01-26 1982-06-01 Merck & Co., Inc. N-Substituted-benzyl-11-endo-amino-5,6,7,8,9,10-hexahydro-2-hydroxy (or methoxy)-6,9-methanobenzocyclooctene (or nonene) centrally-acting analgesics
US4332810A (en) * 1981-01-26 1982-06-01 Merck & Co., Inc. N-(Substituted)-2,5-ethano-8-hydroxy (or methoxy)-1,2,3,4,5,6-hexahydro-3 (or 4)-benzazocine centrally-acting analgesics
US4376779A (en) * 1981-01-26 1983-03-15 Merck Sharp & Dohme (I.A.) Corp. N-(Substituted)-2-aza-2'-hydroxy-5,6-benzotricyclo[6.3.01,8.04,11 ] undecane centrally-acting analgesics

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1915334A (en) * 1930-10-16 1933-06-27 Du Pont Fluosilicate of organic heterocyclic bases and process of making it
US3138603A (en) * 1958-10-31 1964-06-23 Everette L May New benzomorphans (methanobenzazocines) and preparation thereof
US3372165A (en) * 1960-12-01 1968-03-05 Sterling Drug Inc 1, 2, 3, 4, 5, 6-hexahydro-8-hydroxy-2, 6-methano-3-benzazocine derivatives
GB997637A (en) * 1962-01-31 1965-07-07 Smith Kline French Lab Substituted 2-cyclopropylmethyl-6,7-benzmorphans
US3250678A (en) * 1963-01-16 1966-05-10 Sterling Drug Inc Analgesia producing benzazocines
GB1050227A (en) * 1963-11-07
US3345373A (en) * 1964-05-25 1967-10-03 Smith Kline French Lab 2-polymethylallyl-5, 9-dimethyl-6, 7-benzmorphans and derivatives
NL132138C (en) * 1966-05-20
NL132139C (en) * 1966-05-20

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4357471A (en) 1976-12-17 1982-11-02 Rohm And Haas Company Azaspiro compounds
US4374991A (en) 1976-12-17 1983-02-22 Rohm And Haas Company 2,6-Dimethylpiperidinyl-N-carbobutoxymethyl urea
US4400512A (en) * 1976-12-17 1983-08-23 Rohm And Haas Company Azaspiro compounds
US4405630A (en) * 1980-12-29 1983-09-20 Rohm And Haas Company Arthropod repellent compositions and methods

Also Published As

Publication number Publication date
DE2002840C3 (en) 1980-04-10
CH534165A (en) 1973-02-28
FR2034485A1 (en) 1970-12-11
DE2002840A1 (en) 1970-08-06
NL7000166A (en) 1970-07-27
FR2034485B1 (en) 1974-01-11
DE2002840B2 (en) 1979-08-02
US3700734A (en) 1972-10-24
BR6914877D0 (en) 1973-02-08

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