GB1185432A - Process for Producing Benzomorphane Derivatives - Google Patents

Process for Producing Benzomorphane Derivatives

Info

Publication number
GB1185432A
GB1185432A GB2634668A GB2634668A GB1185432A GB 1185432 A GB1185432 A GB 1185432A GB 2634668 A GB2634668 A GB 2634668A GB 2634668 A GB2634668 A GB 2634668A GB 1185432 A GB1185432 A GB 1185432A
Authority
GB
United Kingdom
Prior art keywords
benzomorphane
group
solution
acetoxy
dry toluene
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
GB2634668A
Inventor
36652, (32)07061967 (33)Jp
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.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
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 Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Publication of GB1185432A publication Critical patent/GB1185432A/en
Expired legal-status Critical Current

Links

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

1,185,432. Process for producing benzomorphane derivatives. SUMITOMO CHEMICAL CO. Ltd. 31 May, 1968 [7 June, 1967(2)], No. 26346/68. Heading C2C. A process for the preparation of a 6,7- benzomorphane derivative of formula in which each of R 1 and R 2 is a hydrogen atom, a C 1-3 alkyl group or a phenyl group, R 3 is a hydrogen atom or a C 1-3 alkyl group and R 4 is an alkenyl or haloalkenyl group having 2 to 5 carbon atoms, a C 3-5 cycloalkyl group, a C 2-5 alkynyl group, a phenyl group, a phenylalkyl group or a phenylalkenyl group, which comprises reducing a 6,7-benzomorphane 2-amido having the formula in which R 1 , R 2 and R 4 are as defined above and Rs is a hydrogen atom or an alkyl or alkanoyl group having 1 to 3 carbon atoms, with a dealkyl aluminium hydride or a trialkyl aluminium, in the presence of a solvent. The 6,7-benzomorphane 2-amide derivative is produced by the acylation of a 2-methyl-6,7- benzomorphane having the formula in. which R 1 , R 2 and R 5 are as defined above, with an acid halide having the formula: R 4 COX in which R 4 is as defined above and X is a halogen atom. 21 - Acetoxy - 2 - (3<SP>11</SP>- methylbuten - 2<SP>11</SP> - oyl) - 5,9-dimethyl-6,7-benzomorphane is prepared by adding a solution of 2<SP>1</SP>-acetoxy-2,5,9-trimethyl-6,7-benzomorphane in dry toluene to a solution of #-#dimethylacryl chloride in dry toluene at below 5‹ C. and then heating the mixture. 2<SP>1</SP> - Acetoxy - 2 - cyclopropylcarbonyl - 5,9 - dimethyl - 6,7 - benzomorphane is prepared by adding a solution of 2<SP>1</SP>-acetoxy-2,5,9-trimethyl-6,7-benzomorphane in toluene to a solution of cyclopropylcarboxylic acid chloride in dry toluene at below 10‹ C. and then heating the mixture under reflux. 2<SP>1</SP>-Hydroxy-2-cyclopropylcctrbonyl- 5,9- dimethyl- 6,7- benzomorphane is prepared by adding a solution of 2<SP>1</SP>-acetoxy- 2,5,9-trimethyl-6,7-benzomorphane in dry toluene to a solution of cyclopropyl carboxylic acid chloride in dry toluene below 10‹ C. and then heating the mixture under reflux.
GB2634668A 1967-06-07 1968-05-31 Process for Producing Benzomorphane Derivatives Expired GB1185432A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP3665167 1967-06-07
JP3665267 1967-06-07

Publications (1)

Publication Number Publication Date
GB1185432A true GB1185432A (en) 1970-03-25

Family

ID=26375728

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2634668A Expired GB1185432A (en) 1967-06-07 1968-05-31 Process for Producing Benzomorphane Derivatives

Country Status (6)

Country Link
AT (1) AT298686B (en)
CH (2) CH521348A (en)
DE (1) DE1770538C3 (en)
FR (1) FR1605421A (en)
GB (1) GB1185432A (en)
SE (2) SE343302B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2355830A1 (en) * 1976-06-21 1978-01-20 Acf Chemiefarma Nv NEW DERIVATIVES OF 6-7-BENZOMORPHANE, THEIR OBTAINING AND PHARMACEUTICAL COMPOSITION CONTAINING THEM
US5354758A (en) * 1992-12-16 1994-10-11 Japan Tobacco Inc. Benzomorphans useful as NMDA receptor antagonists

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2355830A1 (en) * 1976-06-21 1978-01-20 Acf Chemiefarma Nv NEW DERIVATIVES OF 6-7-BENZOMORPHANE, THEIR OBTAINING AND PHARMACEUTICAL COMPOSITION CONTAINING THEM
US5354758A (en) * 1992-12-16 1994-10-11 Japan Tobacco Inc. Benzomorphans useful as NMDA receptor antagonists

Also Published As

Publication number Publication date
CH521348A (en) 1972-04-15
SE343302B (en) 1972-03-06
DE1770538C3 (en) 1978-06-22
SE394277B (en) 1977-06-20
DE1770538A1 (en) 1972-04-13
CH527824A (en) 1972-09-15
DE1770538B2 (en) 1977-10-27
AT298686B (en) 1972-05-25
FR1605421A (en) 1975-06-13

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Legal Events

Date Code Title Description
414F Notice of opposition given (sect. 14/1949)
414B Case decided by the comptroller ** grants allowed (sect. 14/1949)
49R Reference inserted (sect. 9/1949)
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee