IL43456A - 1,2,3,4,5,6-hexahydro-8-hydroxy-3-benzazocine derivatives,their preparation and pharmaceutical compositions containing them - Google Patents

1,2,3,4,5,6-hexahydro-8-hydroxy-3-benzazocine derivatives,their preparation and pharmaceutical compositions containing them

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Publication number
IL43456A
IL43456A IL43456A IL4345673A IL43456A IL 43456 A IL43456 A IL 43456A IL 43456 A IL43456 A IL 43456A IL 4345673 A IL4345673 A IL 4345673A IL 43456 A IL43456 A IL 43456A
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IL
Israel
Prior art keywords
acid addition
methyl
compound
formula
addition salt
Prior art date
Application number
IL43456A
Other versions
IL43456A0 (en
Original Assignee
Sparamedica Ag
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 Sparamedica Ag filed Critical Sparamedica Ag
Publication of IL43456A0 publication Critical patent/IL43456A0/en
Publication of IL43456A publication Critical patent/IL43456A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Claims (1)

1. 43456/3;- - 1. Process for the manufacture of bensazocine derivatives of the general formula ■wherein R? signifies lower alkyl, cycloalk l- j lower alkyl, lower alkenyl, .phenethyl or; \" ' • and R^ each represents hydrogen or lower alkyl with at least one of '·'·":, ^ or R^. being lower alkyl and at least one of ¾ and R^ being other than methyl, wherein, when j and R^ are not alike, the compounds are present as racemates or as optical antipodes, and of pharmaceutically acceptable acid addition salts of these compounds, which process comprises reacting a compound of the formula wherein R , R-. and R. have the above meanings and represents lower alkyl, or an acid addition salt thereof with an ether cleaving agent to effect conversion of the R10-gro p to hydroxy, or reacting a compound of the formula wherein R^ and R^ have the above meanings, or an acid addition salt thereof vrith agents yielding the .group Rg, whereupon, in any desired sequence, if desired, a racer.ate obtained is separated into the optica antipodes and, if desired, a base obtained is converted into a pharmaceutically acceptable acid addition salt* 2. Process according to Claim 1, wherein a compound of formula II or III or an acid addition salt thereof, wherein and are different, is utilized as starting material. 3. Process according to Claim 1 or 2, wherein a compound of formula II or III or an acid addition salt thereo wherein R^ and ^ are lower alkyl, is utilized as starting material. 4. Process according to any one of Claims 1-3» wherein a compound of formula II or III or an acid addition salt thereof, wherein R^ is methyl and R^ ethyl, is utilized 5. Process according to any one of Claims 1-4, wherein an agent yielding the group Rg, a compound of formula II or an acid addition salt thereof, wherein Rg is lower alkyl, is utilized as starting material. 6. Process according to any one of Claims 1-5 , wherein an agent yielding the group Rg, a compound of formula II or an acid addition salt thereof, wherein R≥ is methyl, is utilized as starting material. 7· Process according to any one of Claims 1-6, wherein the (+) -isomer of the compound of formula II or III or of an acid addition salt thereof is used as starting mat or a race ate obtained as end product is separated into the optical antipodes and the (+)-isomer isolated. 8. Process according to any one of Claims 1, 2, 5 and 6, for the manufacture of rac .1,2,3,4,5,6-hexahydro-8-hydroxy-3,6-dimethyl-3-benzazocine and pharmaceutical acceptable acid addition salts thereof, wherein a compound of formula II or an acid addition salt thereof, in which R2 and R^ are" both methyl and R^ is hydrogen, and an ether cleaving agent or a compound of formula III or an acid addition salt thereof, in which R^ is methyl and is hydrogen, and agents yielding the group R≥, in which Rg is methyl, are used as starting materials. 43456/2 (V 9· Process according to any one of Claims 1, 2 and 5-7, for the manufacture of the (+) isomer of the compound of formula I prepared in Claim 8 or of an acid addition salt thereof, characterized in that said compound or salt is separated into the optical antipodes and the (+)- isomer isolated or in that there is utilized the (+)-isomer of one of the starting materials utilized in Claim 8. 10. Process according to any one of Claims 1, 2, 5 and 6, for the manufacture of the (-)-isomer of the compound of formula I prepared in Claim 8 or of an acid addition salt thereof, characterized in that said compound or salt is separated into the optical antipodes and the (-)-isomer isolated or in that there is utilized the (-')-iso-mer of one of the starting materials utilized in Claim 8. 11. Process according to any one of Claims 1-6 for the manufacture of rac .6-ethyl-1,2,3,4,5, 6-hexahydro^ 8-hydroxy-3,6-dimethyl-3-benzazoc ne and pharmaceutically acceptable acid addition salts thereof, wherein a compound of formula II or an acid addition salt thereof, in which R2 and R^ are both methyl and is ethyl, and an ether cleaving agent or a compound of formula III or an acid addition salt thereof, in which R^ is methyl and R^ is ethyl, and agents yielding the group R≥, in which Rg is methyl, are used as starting materials. 43456/2 12. Process according to any one 6f Claims 1-7, for the manufacture of the (+) -isomer of the compound of formula I, prepared in Claim 11 or of an acid addition salt thereof, characterized in that said compound or salt is separated into the optical antipodes and the (+)-isomer isolated or in that there is utilized the (+)-isomer of one of the starting materials utilized in Claim 11. 13· Process according to any one of Claims 1-6, for the manufacture of the (-)-isomer of the compound of formula I, prepared iri Claim 11 or of an acid addition salt thereof, characterized in that said compound or salt is separated into the optical antipodes and the (-) -isomer isolated or in that there is utilized the (-) -isomer of one of the starting materials utilized in Claim 11. ,14. Process, according to any one of Claims 1-4 and 7* wherein an agent yielding the group R2, a compound of formula II or an acid addition salt thereof, wherein R≥ is lower alkenyl, is utilized as starting material. 15. Process according to Claim 1, 2 or 14, for the manufacture of rac .3-allyl-l,2,3» ,5,6-hexahydro-8-hydroxy-6-rnethyl-j5-benzazocine and pharmaceutical acceptable acid addition salts thereof, wherein a compound of formula II or an acid addition salt thereof, in which Rg is allyl, R^ or a compound of formula III or an acid addition salt thereof, in which is methyl and R^ is hydrogen, and agents yielding the group R2, in which R2 is allyl, are. used as starting materials. 16. Process according to Claim 1, 3 0r 14 for the manufacture of 3-allyl-l,2,;5,4,5,6-hexahydro-8-hydroxy-6,6-dimethyl-2-benzazocine and pharmaceutically acceptable acid addition salts thereof, wherein a compound of formula II or an acid addition salt thereof, in which R2 is allyl and R^ and ^ are both methyl, and an ether cleaving agent or a compound of formula III or an acid addition salt thereof, in which R^ and R^ are both methyl, and agents yielding the group Rg, in which R2 is allyl, are used as starting materials. 17. Process according to any one of Claims 1-4 and 14 for the manufacture of rac .3-allyl-6-ethyl-l,2,j5,4,5,6-hexahydro-8-hydroxy-6-methyl-3-benzazocine and pharmaceutically acceptable salts thereof, wherein a compound of formula II or an acid addition salt thereof, in which R2 is allyl, R^ is methyl and R^ is ethyl, and an ether cleaving agent or a compound of formula III or an acid addition salt thereof, in which R^ is methyl and R^ is ethyl, and agents yielding the group R2, in which Rg is allyl, are used as starting materials. 18. Process according to any one of Claims 1-4 and 7, wherein an agent yielding the group Rg, a compound of formula II or an acid addition salt thereof, wherein Rg is cycloalkyl-lower alkyl, is utilized as starting material. 19. Process according to Claim l, 2 or l8, for the manufacture of rac.3-cyclopropylmethyl-l,2,3# ,5,6-hexahydro 8-hydroxy-6-methyl-3-benzazocine and pharmaceutically acceptable acid addition salts thereof, wherein a compound of formula II or an acid addition salt thereof, in which Rg is cyclopropylmethyl, R^ is methyl and R^ is hydrogen, and an ether cleaving agent or a compound of formula III or an acid addition salt thereof, in which R^ is methyl and ^ is hydrogen, and agents yielding the group Rg, in which R2 is cyclopropyl-methyl are used as starting materials. 20. Process according to Claim 1, 3 or 18, for the manufacture of 3-cyclopropylmethyl-l,2,3> ,5,6-hexahydro-8-hydroxy-6,6-dimethyl-3-benzazocine and pharmaceutically acceptable acid addition salts thereof, wherein a compound of formula II or an acid addition salt thereof, in which Rg is cyclopropyl-methyl and R^ and R^ are both methyl, and an ether cleaving agent or a compound of formula III or an, acid addition salt thereof, in which R^ and R^ are both methyl, and agents yielding the group Rg, wherein Rg is cyclopropyl-methyl are used as starting materials. 21. Process according to any one of Claims 1-4 and 18, for the manufacture of rac3-cyclopropylmethyl-6-ethyl-l,2, 3*^>5>6-hexahydro-8-hydroxy-6-methyl-3-benzazocine and pharmaceutically acceptable acid addition salts thereof, wherein a compound of formula II or an acid addition salt thereof, in which R2 is eyclopropylmethyl, is methyl and R^ is ethyl, and an ether cleaving agent or a compound of formula III or an acid addition salt thereof, in which R^ is methyl and ^ is ethyl, and agents yielding the group Rg, wherein Rg is cyclopropyl-methyl are used as starting materials. 22. Process for the preparation o lienzazocine derivatives as hereinbefore particularly described, especially with reference to the foregoing Examples. 23. Process for the. manufacture of preparations having analgesic properties, characterized in that a benzazocine derivative of the general formula wherein R2 signifies lower alkyl, cycloalkyl- iower alkyl, lower alkenyl, or phenethyl; ; RT and R. each represents. hydrogen .02- lower, alkyl with at least one of R_j or ^ being lower alkyl and at least one of ■' ^, j and ..R ·· bein . other than methyl, wherein, when j and R^ are not alike, the compounds are present as racemates or as optical antipodes, or a pharmaceutically acceptable acid addition salt thereof is mixed,, as active substance, with nontoxic, inert, therapeutically compatible solid or liquid carriers, commonly used in such preparations, and/or excipients. ;24. Compositions having analgesic properties, comprising a benzazocine derivative of the general formula wherein signifies lower alkyl, cycloalkyl- 43456/2 hydrogen or lower alkyl with at least one of R^ or R^ being lower alkyl and at least one of R2, R^ and R^ being other than methyl, wherein, when R and R^ are not alike, the compounds are present as racemates or as optical antipodes, or a pharmaceutically acceptable acid addition salt thereof, and a carrier. 25 Benzazocine derivatives of the general formula wherein signifies lower alkyl, cycioalkyl- .lower alkyl, lower alkenyl, phenethyl or ; R, and R. each represents hydrogen or lower alkyl with at least one of or ^ "being lower alkyl and at least one of 2, ^ and ^ being other than, methyl, wherein, when j and ^ are not alike, the compounds are present as racemates or as optical antipodes, and pharmaceutically acceptable acid addition salts thereof. 26. Compounds of Claim .25, wherein R^ and ^ are different. 27. Compounds of Claim ;25 or 26, wherein R^ and ^ are lower alkyl. I 28. Compounds of Claim 25, 26 or 27, wherein ^ is methyl and ^ ethyl. 29. Compounds of any one of Claims 25-28, wherein 2 is lower alkyl, 43456/3 30. Compounds of any one of Claims 25-29, wherein is methyl. 31. Compounds of any one of Claims 25-30,; in form of the (+) -antipode . . 32..-rac.l,2,;3»^i5»6-Hexahydro-8-hydroxy-3,6-dimethyl-3-benzazocine and pharmaceutically acceptable acid addition salts thereof. 33., (+)-l,2,3, ,5,6-Hexahydro-8-hydroxy-3,6-dimethyl-benzazocine and pharmaceutically acceptable acid addition salts thereof. 34. (-)-l,2,3, ,5,6-Hexahydro-8-hydroxy-3, 6-dimethyl-> benzazocine and pharmaceutically acceptable acid addition salts thereof. 35. rac .6-Ethyl-l,2, , ,5,6-hexahydro-8-hydroxy-^.,6-dimethyl-3-benzazocine and pharmaceutically acceptable acid addition salts thereof. 36. (+)-6-Ethyl-l,2,3,2W5,6-hexahydro-8-hydroxy-3,6-dimethyl-3-benzazocine and pharmaceutically acceptable acid addition salts thereof. 37. (-)-6-Ethyl-l,2,3,^i5*6-hexahydro-8-hydroxy-3,6-dimethyl-3-benzazocine and pharmaceutically acceptable 43456/3 . v 38. Compounds of any one of Claims 25-28 and 31, wherein is lower alkenyl.. 39. rac .3-Allyl-l>2,3,4,5, 6-hexahydro-8-hydroxy-6-methyl-3-benzazocine and pharmaceutically acceptable acid addition salts thereof. - — ·' 40..3-Allyl-l,.2,3,4,5,6-hexahydro-8-hydroxy'-6,6-dimethyl-3-benzazocine and pharmaceutically acceptable acid addition salts thereof. 41. rac.3-Allyl-6-ethyl-l,2,3,4,5.,6-hexahydro-8-hydroxy-6-methyl-3-benzazocine and pharmaceutically acceptable acid addition salts thereof. 42. Compounds of any one of Claims 25-28 and 31, wherein R2 is cycloalkyl-lower alkyl. 43. rac .3-Cyclopropylmethyl-l,2,3,4,5,6-hexahydro-8-hydroxy-6-methyl-3-benzazocine and pharmaceutically acceptable acid addition salts thereof. 44 · 3-Cyclopropylmethyl-1,2,3,4,5,6-hexahydro-8-hydroxy-6,6-dimethyl-3-benzaz 45. rac^ -Cyclopropylmethyl-e-ethyl-l,2, ,4,5, 6-hexahydro-8-hydroxy-6-methyl-3-benzazocine and pharmaceutically ' 1 r 46. Compounds of formula X in Claim 1 in the form of their raoemates or optical antipodes and pharmaceutically acceptable acid additionssalts thereof. 47. Compounds according to any of Claims 25 to 46 when prepared by a process PC/AJ
IL43456A 1972-10-24 1973-10-22 1,2,3,4,5,6-hexahydro-8-hydroxy-3-benzazocine derivatives,their preparation and pharmaceutical compositions containing them IL43456A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US30004472A 1972-10-24 1972-10-24
US34880873A 1973-04-06 1973-04-06
US38321673A 1973-07-27 1973-07-27

Publications (2)

Publication Number Publication Date
IL43456A0 IL43456A0 (en) 1974-01-14
IL43456A true IL43456A (en) 1976-12-31

Family

ID=27404688

Family Applications (1)

Application Number Title Priority Date Filing Date
IL43456A IL43456A (en) 1972-10-24 1973-10-22 1,2,3,4,5,6-hexahydro-8-hydroxy-3-benzazocine derivatives,their preparation and pharmaceutical compositions containing them

Country Status (13)

Country Link
JP (1) JPS4972280A (en)
AR (2) AR200581A1 (en)
AU (1) AU6124373A (en)
DD (1) DD109629A5 (en)
DE (1) DE2353062A1 (en)
ES (1) ES419855A1 (en)
FR (1) FR2203637B1 (en)
GB (1) GB1448243A (en)
IE (1) IE38399B1 (en)
IL (1) IL43456A (en)
LU (1) LU68663A1 (en)
NL (1) NL7314606A (en)
PH (1) PH11587A (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH529763A (en) * 1968-02-09 1972-10-31 Takeda Chemical Industries Ltd Process for the production of new hexahydrobenzazocines

Also Published As

Publication number Publication date
AU6124373A (en) 1975-04-10
AR207853A1 (en) 1976-11-08
IE38399B1 (en) 1978-03-01
GB1448243A (en) 1976-09-02
LU68663A1 (en) 1975-06-24
FR2203637A1 (en) 1974-05-17
FR2203637B1 (en) 1977-01-28
ES419855A1 (en) 1976-02-16
DD109629A5 (en) 1974-11-12
IE38399L (en) 1974-04-24
NL7314606A (en) 1974-04-26
PH11587A (en) 1978-03-31
AR200581A1 (en) 1974-11-22
DE2353062A1 (en) 1974-05-09
IL43456A0 (en) 1974-01-14
JPS4972280A (en) 1974-07-12

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