GB1366834A - Dioxino-quinoline derivates having pharmacological effects - Google Patents

Dioxino-quinoline derivates having pharmacological effects

Info

Publication number
GB1366834A
GB1366834A GB583473A GB583473A GB1366834A GB 1366834 A GB1366834 A GB 1366834A GB 583473 A GB583473 A GB 583473A GB 583473 A GB583473 A GB 583473A GB 1366834 A GB1366834 A GB 1366834A
Authority
GB
United Kingdom
Prior art keywords
alkyl
compound
chnh
eto
alkoxy
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
GB583473A
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.)
Koninklijke Philips NV
Original Assignee
Philips Gloeilampenfabrieken NV
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
Priority claimed from NL7201675A external-priority patent/NL7201675A/xx
Priority claimed from NL7215366A external-priority patent/NL7215366A/en
Application filed by Philips Gloeilampenfabrieken NV filed Critical Philips Gloeilampenfabrieken NV
Publication of GB1366834A publication Critical patent/GB1366834A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/10—Antioedematous agents; Diuretics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

1366834 Dioxino[2,3-g]quinolines PHILIPS GLOEILAMPENFABRIEKEN NV 6 Feb 1973 [9 Feb 1972 14 Nov 1972] 5834/73 Heading C2C The invention comprises compounds of formula and their addition salts with pharmaceutically acceptable acids, wherein R 1 is C 1-4 alkyl, CHR 4 OR 6 (R 4 is H or C 1-3 alkyl, R 6 is H or C 2-4 acyl) or COR 5 where R 5 is alkoxy (possibly substituted by dialkylamino, alkoxy or cycloalkyl), alkenoxy or cycloalkoxy containing up to 4 (but if R 3 is halogen or CF 3 , up to 6) carbon atoms, OH (and its alkali metal salts), NH 2 , H or C 1-3 alkyl; R 2 is either (CH 2 ) 1-2 OR 7 where R 7 is H, C 2-4 acyl, (up to C 8 ) phenylalkyl or dialkylaminoalkyl, or (up to C 6 ), alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxyalkyl or tetrahydrofuranylalkyl, or (CH 2 ) 1-2 S(O) 0-2 R 8 where R 8 is C 1-3 alkyl; R 3 is H, halogen, C 1-4 alkyl or alkoxy, CF 3 , NO 2 , NH 2 , CN, OH or (up to C 4 ) acylamino; and R is OH, SH, C 1-3 alkoxy or alkylthio, or (when R 3 is halogen or CF 3 ) Cl or Br. In examples, these compounds are prepared by (1) cyclizing a benzodioxan, substituted in the 2 and 5 positions by R 2 and R 3 respectively, and by either (a) 7-NHCH:C(COR 5 )CO 2 Et, or (b) 6-CO 2 Me and 7-NHCH:CHCO 2 Et; (2) esterifying the corresponding acid chloride or hydrolysing the corresponding nitrile or ester; (3) hydrolysing, alcoholysing or thiolysing the compound where R = Cl; (4) reducing the composition where R 1 is Ac or CO 2 Et; (5) hydrogenolysing the compound where R 2 is PhCH 2 OCH 2 ; (6) replacing R = OH by Cl; (7) N-acylating the compound where R 3 is NH 2 ; (8) ammonolysis of the compound where R 1 is CO 2 Et; (9) reducing the compound where R 3 is NO 2 (which may be prepared by nitration). Intermediates otherwise prepared are 2-ethoxymethylbenzodioxan further substituted by 7-NH 2 , 5-CF 3 -7-NH 2 , 7-NO 2 , 5-CF 3 - 7-NO 2 , 5-I-7-NO 2 (and the 2-HOCH 2 analogue), 7-HON:CHCONH, 6-CO 2 H-7- NH 2 (and the Me ester), 7-EtO 2 CC(CN): CHNH, 7-(EtO 2 C) 2 C: CHNH; and 5-Cl-7- (EtO 2 C) 2 C: CHNH; 2-benzyloxyphenol further substituted by 4-NH 2 , 4-NO 2 -6-I and 4-(EtO 2 C) 2 C: CHNH; ethyl 7-benzyloxy-4,- 6 - dihydroxyquinoline - 3 - carboxylate, its 6-ClCH 2 CHOHCH 2 - ether and the 7-HO analogue of the latter; and 3-ethoxymethyldioxino[2,3-f]isatin. Therapeutic compositions for oral, parenteral and rectal administration comprise compounds of the above formula which have diuretic, saluretic and blood pressure lowering activity, and are stated to be useful for treating hypertension, cardiac asthma, decompensation of the heart, pulmonary oedema, hepatic oedema with ascites; nephrogenous, cardiac, pregnancy, lymphatic, iodopathic, post-traumatic or medicamentous oedema; oedema in adiposis or in malignant diseases; premenstrual tension, nephrotic syndrome, gestational toxicosis, barbiturate intoxication, inhibition of lactation and renal and central diabetes insipidus.
GB583473A 1972-02-09 1973-02-06 Dioxino-quinoline derivates having pharmacological effects Expired GB1366834A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL7201675A NL7201675A (en) 1972-02-09 1972-02-09
NL7215366A NL7215366A (en) 1972-11-14 1972-11-14 P-dioxino(2,3-g)quinolines - diuretics, saluretics and hypotensives

Publications (1)

Publication Number Publication Date
GB1366834A true GB1366834A (en) 1974-09-11

Family

ID=26644729

Family Applications (1)

Application Number Title Priority Date Filing Date
GB583473A Expired GB1366834A (en) 1972-02-09 1973-02-06 Dioxino-quinoline derivates having pharmacological effects

Country Status (16)

Country Link
US (1) US3865832A (en)
JP (1) JPS5727112B2 (en)
AR (1) AR211510A1 (en)
AT (1) AT323740B (en)
BE (1) BE795265A (en)
CA (1) CA1000279A (en)
CH (1) CH593285A5 (en)
DE (1) DE2303496A1 (en)
DK (1) DK138120B (en)
ES (1) ES411374A1 (en)
FI (1) FI55847C (en)
FR (1) FR2181708B1 (en)
GB (1) GB1366834A (en)
IL (1) IL41471A (en)
PH (1) PH14448A (en)
SE (1) SE416467B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4036962A (en) * 1974-08-12 1977-07-19 E. I. Du Pont De Nemours And Co. 6,7-Methylenedioxy-1-(2,2,2-trifluoroethyl)-4(1H)-quinolone-3-carboxylic acid and its salts and esters
US4179506A (en) * 1978-11-13 1979-12-18 Warner-Lambert Company New pyridobenzodioxin compounds and methods for their production
FR2846327B1 (en) * 2002-10-25 2006-03-24 Merck Sante Sas N-BENZODIOXOLYL, N-BENZODIOXANYL AND N-BENZODIOXEPINYL ARYLCARBOXAMIDE DERIVATIVES USEFUL IN THE TREATMENT OF DYSLIPIDEMIA AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
CA2757084C (en) * 2009-03-30 2017-08-29 Transtech Pharma, Inc. Substituted azoanthracene derivatives, pharmaceutical compositions, and methods of use thereof
CN113717185B (en) * 2021-08-19 2023-04-11 云南省烟草农业科学研究院 Quinoline alkaloid compound with antibacterial activity in cigar rhizome and preparation method and application thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3178348A (en) * 1961-02-08 1965-04-13 Norwich Pharma Co Hypotensive quinolines
GB1076828A (en) * 1963-12-12 1967-07-26 Warner Lambert Pharmaceutical Methylenedioxy quinoline derivatives
DE1908548A1 (en) * 1968-02-29 1970-11-05 Warner Lambert Co Quinoline derivatives
CA942310A (en) * 1969-07-09 1974-02-19 Mitsuo Nakashita Preparation of n-substituted 6,7-methylenedioxy-4-quinolone derivatives
DE2030899A1 (en) * 1970-06-18 1971-12-23 Schering Ag, 1000 Berlin Und 4619 Bergkamen Quinoline carboxylic acid derivatives

Also Published As

Publication number Publication date
SE416467B (en) 1981-01-05
FI55847B (en) 1979-06-29
FI55847C (en) 1979-10-10
IL41471A0 (en) 1973-04-30
AT323740B (en) 1975-07-25
ES411374A1 (en) 1976-07-01
DK138120B (en) 1978-07-17
IL41471A (en) 1975-12-31
CA1000279A (en) 1976-11-23
BE795265A (en) 1973-08-09
AR211510A1 (en) 1978-01-30
US3865832A (en) 1975-02-11
JPS4886896A (en) 1973-11-15
PH14448A (en) 1981-07-23
CH593285A5 (en) 1977-11-30
FR2181708B1 (en) 1975-10-10
FR2181708A1 (en) 1973-12-07
DK138120C (en) 1978-12-04
JPS5727112B2 (en) 1982-06-08
DE2303496A1 (en) 1973-08-23

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
PCNP Patent ceased through non-payment of renewal fee