GB1011554A - Substituted isoquinolines and pharmaceutical compositions thereof - Google Patents

Substituted isoquinolines and pharmaceutical compositions thereof

Info

Publication number
GB1011554A
GB1011554A GB32120/62A GB3212062A GB1011554A GB 1011554 A GB1011554 A GB 1011554A GB 32120/62 A GB32120/62 A GB 32120/62A GB 3212062 A GB3212062 A GB 3212062A GB 1011554 A GB1011554 A GB 1011554A
Authority
GB
United Kingdom
Prior art keywords
benzyl
diethoxy
tetraethoxy
alkyl
methyl
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
GB32120/62A
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.)
Chinoin Private Co Ltd
Original Assignee
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
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 Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Publication of GB1011554A publication Critical patent/GB1011554A/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
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/24—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • A61K31/515—Barbituric acids; Derivatives thereof, e.g. sodium pentobarbital
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

<FORM:1011554/C2/1> The invention comprises (A) compounds I wherein either A is 3,4-diethoxy-benzyl and R is alkyl of at least two carbon atoms, or A is 3,4-diethoxy-benzal and R is hydrogen or alkyl, and their acid addition salts and a methobromide, (B) the preparation of compound I wherein A is 3,4-diethoxy-benzyl or 3,4-diethoxy-benzal and R is hydrogen or alkyl, by (a) ring closure of compounds <FORM:1011554/C2/2> in the presence of a water-binding condensation agent below 100 DEG C., or (b) reduction of 6,7,31,41 -tetraethoxy - 1 - benzyl - isoquinoline or a salt thereof, or (c) reduction of 6,7,31, 41-tetraethoxy - 1 - benzyl - 3,4 - dihydro - isoquinoline or a quaternary salt thereof, and (d) possibly alkylating at position 2 on N-unsubstituted compound; quaternary starting materials for methods (b) and (c) may be obtained by prior reaction of N-unsubstituted compounds with alkyl halides: the preparation of the known compound 1,2,3,4 - tetrahydro - 2 - methyl-6,7,31,4 - tetraethoxy - 1 - benzyl isoquinoline by hydrogenating 6,7,31,41 - tetraethoxy - 1 - benzyl - N - methyl - isoquinoliumiodide is disclaimed.ALSO:Pharmaceutical compositions contain tetrahydro-isoquinolines of general formula <FORM:1011554/A5-A6/1> (I) where A is 3, 4-diethoxy-benzyl or 3, 4-diethoxy-benzal and R is hydrogen or alkyl, and their acid addition salts and a metholbromide in association with pharmeceutical carriers. Oral, parenteral and rectal administration of suitable preparations (tablets, dragees, capsules, powders, granules, solutions, suspensions, suppositories) is mentioned. Other ingredients which may be incorporated include analgesics, tranquillisers, antiphlogistics, diuretics, spasmolytics, choleretics and vasodilators (nicotinic acid, methyl homatropine bromide, menthol, phenol phthalein, hexamethylene tetramine, cholic acid, codein, amidazophen, novamidazophen, reserpine, phenobarbital, N-(3)-phenyl-propyl-(2)-1, 1-diphenyl-propyl-(3)-amino-lactate, citric acid, atropine methyl nitrate, cerethane). The compounds have spasmolytic, analgesic, vasodilatory and hypo tensive properties. Commonplace solutions of the known compound 1, 2, 3, 4-tetrahydro-2-methyl-6, 7, 31, 41-tetraethoxy-1-benzyl isoquinoline are disclaimed.
GB32120/62A 1961-08-30 1962-08-21 Substituted isoquinolines and pharmaceutical compositions thereof Expired GB1011554A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HUCI000380 1961-08-30
HUCI000390 1962-04-10

Publications (1)

Publication Number Publication Date
GB1011554A true GB1011554A (en) 1965-12-01

Family

ID=26318367

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32120/62A Expired GB1011554A (en) 1961-08-30 1962-08-21 Substituted isoquinolines and pharmaceutical compositions thereof

Country Status (5)

Country Link
CH (3) CH424782A (en)
DK (1) DK104513C (en)
FI (1) FI40718B (en)
FR (1) FR2057M (en)
GB (1) GB1011554A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103664781A (en) * 2013-12-13 2014-03-26 浙江普洛康裕制药有限公司 Drotaverine hydrochloride crystal form I and crystal form II and preparation method
CN103694171A (en) * 2013-12-13 2014-04-02 浙江普洛康裕制药有限公司 Drotaverine hydrochloride crystal form III and crystal form IV and preparation method thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103664781A (en) * 2013-12-13 2014-03-26 浙江普洛康裕制药有限公司 Drotaverine hydrochloride crystal form I and crystal form II and preparation method
CN103694171A (en) * 2013-12-13 2014-04-02 浙江普洛康裕制药有限公司 Drotaverine hydrochloride crystal form III and crystal form IV and preparation method thereof
CN103694171B (en) * 2013-12-13 2016-06-29 浙江普洛康裕制药有限公司 Drotaverine hydrochloride crystal form II I and form IV and preparation method thereof

Also Published As

Publication number Publication date
FI40718B (en) 1969-01-31
DK104513C (en) 1966-05-31
CH424783A (en) 1966-11-30
FR2057M (en) 1963-10-07
CH425793A (en) 1966-12-15
CH424782A (en) 1966-11-30

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