GB1173719A - Optical Resolution of 1-(3,4,5-Trimethoxybenzyl)-6,7-Dihydroxy-1,2,3,4-Tetrahydroisoquinoline - Google Patents

Optical Resolution of 1-(3,4,5-Trimethoxybenzyl)-6,7-Dihydroxy-1,2,3,4-Tetrahydroisoquinoline

Info

Publication number
GB1173719A
GB1173719A GB09533/68A GB1953368A GB1173719A GB 1173719 A GB1173719 A GB 1173719A GB 09533/68 A GB09533/68 A GB 09533/68A GB 1953368 A GB1953368 A GB 1953368A GB 1173719 A GB1173719 A GB 1173719A
Authority
GB
United Kingdom
Prior art keywords
acid
salts
tetrahydroisoquinoline
dihydroxy
tartaric
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
GB09533/68A
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.)
Tanabe Seiyaku Co Ltd
Original Assignee
Tanabe Seiyaku 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 Tanabe Seiyaku Co Ltd filed Critical Tanabe Seiyaku Co Ltd
Publication of GB1173719A publication Critical patent/GB1173719A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/18—Aralkyl radicals
    • C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine

Landscapes

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

Abstract

1,173,719. 1 - (3,4,5 - Trimethoxyphenyl)-6,7- dihydroxy - 1,2,3,4 - tetrahydroisoquinoline. TANABE SEIYAKU CO. Ltd. 25 April, 1968 [27 April, 1967], No. 19533/68. Heading C2C. The title base (racemate) is resolved by treatment in solution with an optically active organic acid, and separating the resultant diastereoisomeric salts by fractional crystallization; the salts may be treated with an inorganic acid to form the corresponding inorganic acid addition salts. The optically active acid is e.g. d- or l-tartaric dibenzoyl-D-tartaric, D-(-)- quinic or D-10-camphorsulphonic acid. Specified products are salts of the d- and l-isomers with d-tartaric acid and with HCl. The racemate is synthesized from 2-(3,4-dihydroxyphenyl) ethylamine and 3,4,5-trimethoxyphenylacetaldehyde under acid conditions. Therapeutic compositions having bronchodilating and blood pressure lowering activity comprise optically active acid addition salts of 1 - (3,4,5 - trimethoxyphenyl) - 6,7 - dihydroxy- 1,2,3,4-tetrahydroisoquinoline, in association with a therapeutically acceptable carrier.
GB09533/68A 1967-04-27 1968-04-25 Optical Resolution of 1-(3,4,5-Trimethoxybenzyl)-6,7-Dihydroxy-1,2,3,4-Tetrahydroisoquinoline Expired GB1173719A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2724167 1967-04-27

Publications (1)

Publication Number Publication Date
GB1173719A true GB1173719A (en) 1969-12-10

Family

ID=12215566

Family Applications (1)

Application Number Title Priority Date Filing Date
GB09533/68A Expired GB1173719A (en) 1967-04-27 1968-04-25 Optical Resolution of 1-(3,4,5-Trimethoxybenzyl)-6,7-Dihydroxy-1,2,3,4-Tetrahydroisoquinoline

Country Status (15)

Country Link
AT (1) AT280288B (en)
BE (1) BE714193A (en)
BR (1) BR6898628D0 (en)
CH (1) CH509315A (en)
CS (1) CS150953B2 (en)
DE (1) DE1770286A1 (en)
DK (1) DK120082B (en)
ES (1) ES353219A1 (en)
FI (1) FI50335C (en)
FR (2) FR1584255A (en)
GB (1) GB1173719A (en)
IL (1) IL29832A (en)
MY (1) MY7000174A (en)
NL (1) NL6805964A (en)
SE (1) SE328575B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4666918A (en) * 1983-06-21 1987-05-19 Tpo "Pharmachim" Tetrahydroisoquinoline derivatives and method

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4666918A (en) * 1983-06-21 1987-05-19 Tpo "Pharmachim" Tetrahydroisoquinoline derivatives and method

Also Published As

Publication number Publication date
BE714193A (en) 1968-09-16
IL29832A (en) 1971-04-28
IL29832A0 (en) 1968-06-20
BR6898628D0 (en) 1973-03-08
FR1584255A (en) 1969-12-19
ES353219A1 (en) 1969-09-01
MY7000174A (en) 1970-12-31
DK120082B (en) 1971-04-05
DE1770286A1 (en) 1970-04-30
AT280288B (en) 1970-04-10
FR307F (en) 1970-04-13
CH509315A (en) 1971-06-30
SE328575B (en) 1970-09-21
FI50335C (en) 1976-02-10
CS150953B2 (en) 1973-09-17
FI50335B (en) 1975-10-31
NL6805964A (en) 1968-10-28

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PE20 Patent expired after termination of 20 years