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SU591148A3 - Method of preparing aminopyrazoleisoquinoline derivatives or salts thereof - Google Patents

Method of preparing aminopyrazoleisoquinoline derivatives or salts thereof

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Publication number
SU591148A3
SU591148A3 SU762326052A SU2326052A SU591148A3 SU 591148 A3 SU591148 A3 SU 591148A3 SU 762326052 A SU762326052 A SU 762326052A SU 2326052 A SU2326052 A SU 2326052A SU 591148 A3 SU591148 A3 SU 591148A3
Authority
SU
USSR - Soviet Union
Prior art keywords
dihydro
boiled
alcohol
methyl
added
Prior art date
Application number
SU762326052A
Other languages
Russian (ru)
Inventor
Такач Кальман
Секереш Ласло
Харшаньи Кальман
Папп Дьюла
Несмельи Андраш
Бенедек Ева
Original Assignee
Хиноин Дьедьсер Еш Ведьесети Термекек Дьяра Рт (Инопредприятие)
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Application filed by Хиноин Дьедьсер Еш Ведьесети Термекек Дьяра Рт (Инопредприятие) filed Critical Хиноин Дьедьсер Еш Ведьесети Термекек Дьяра Рт (Инопредприятие)
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Publication of SU591148A3 publication Critical patent/SU591148A3/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/08Vasodilators for multiple indications
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01JELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
    • H01J23/00Details of transit-time tubes of the types covered by group H01J25/00
    • H01J23/02Electrodes; Magnetic control means; Screens
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01JELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
    • H01J25/00Transit-time tubes, e.g. klystrons, travelling-wave tubes, magnetrons
    • H01J25/34Travelling-wave tubes; Tubes in which a travelling wave is simulated at spaced gaps

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Cardiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Microwave Tubes (AREA)

Claims (5)

П р и м е р 1. К 1,7-5 г 3-(б,7-аимеToicet -3 ,4-дигинро-l-нзoxинoлил)-мeтил-5- -фpни.l,2,4-oкcaдиaзoпa припивают 10 мл l6%-Horo раствора едкого натра и 50 мл спирта и, смесь кип т т 3 .ч с обратным холодильником. . Затем спирт отгон ют под вакуумом и к остатку приливают воду. Получают 1,2 г 2-бензоиламино-5,6-дигидрс 8 ,9 диметоксипиразоло| 5,. хинолина. П Р и мёр PRI me R 1. To 1.7-5 g 3- (b, 7-aimeToicet-3, 4-diginro-l-nsooxynol) -methyl-5-fnn., 2,4-oksadiazopa drink 10 ml of l6% -Horo sodium hydroxide solution and 50 ml of alcohol, and the mixture is boiled for 3 hours under reflux. . The alcohol is then distilled off under vacuum and water is added to the residue. Obtain 1.2 g of 2-benzoylamino-5,6-dihydrs 8, 9 dimethoxypyrazolo | five,. quinoline. P P and mor 2. Смешивают 1 г 3-(6,7-димeтoкcл-3 ,4-Дигидро-1-|Изохинолил )-. тиЛр-5-фенил-1,2,4-оксадиазола с 10 мл гсилола и кип т т 8 ч с обратным холоди льНИКОМУ Охлаждают, получают 0,9 г кристаллического 2-бен&Ьиламино-5,6--ДИ1 идро-8,9- -диметоКенпйразоло 5,1-а изохинолина. П р им ер 2. Mix 1 g of 3- (6,7-dimethox-3, 4-dihydro-1- | Isoquinolyl) -. TiLr-5-phenyl-1,2,4-oxadiazole with 10 ml of gsilol and boiled for 8 hours under reflux. Cooled to obtain 0.9 g of crystalline 2-ben & 5.6-5.6 - DI1 idro-8 , 9-dimethoKenpyrazolo 5,1-a of isoquinoline. P r im er 3. К 1 F 3-(б,7--диметйл-3 ,4-ДИГИДРО-1-ИЗОХИНОЛИЛ)-метил-5-фенил-1 ,2 4-оксад:иазопа добавл ют 25 мл спирта и 7 мл 40%-ного; раствора едкого натра и реакционную массу кип т т 8 ч, с обрат ным холодильником. Затем спирт отгон ют по  вакуумом, к остатку прили1вают воду. Получают 0,6 г кристаллического2-амино- -5:,б- игидрОт-8,9-диметоксипиразолр 5,1- q иаохинолина., П р и м е р 3. To 1 F 3- (b, 7-dimethyl-3, 4-DIHYDRO-1-IZOHINOLYL) -methyl-5-phenyl-1, 2 4-oxad: 25% alcohol and 7 ml 40% - one; caustic soda solution and the reaction mass is boiled for 8 hours, with refluxing. The alcohol is then distilled off under vacuum, and water is added to the residue. Obtain 0.6 g of crystalline 2-amino-5:, b- Ihidro-8,9-dimethoxypyrazole 5,1-q iaoquinoline., Example: 4. К 1 г 3-(б 7-диметоКси-3 ,4-дигидр -1-изохинолил)-метил-5- npQJ пил-1,2,4-о {садиазола приливают 10 мл ксилола и кип т т. 8 ч с обратныгм холодильником . Растворитель отгон аот под вакуумом остаток выкрист аллизовывают из водного . спирта. : - : .: : ... Получают 0,7 г. гемигидрата 2- утирил-.. ,6-дигидро-8,9-диметоксипиразоло {5,1-о |изохинолина; Т.ПЛ, 125-127 С. &лчислено,%: С62,94; Н 6,84; N 12,96 . 0.5 HjO НайденоД: О 62,80; Н 6,71; К 12,75, П р  ме р 4. To 1 g of 3- (b 7-dimethoxy-3, 4-dihydr -1-isoquinolyl) -methyl-5-npQJ saw-1,2,4-o {sadiazole, 10 ml of xylene is poured in and boiled. 8 h with reverse fridge. The solvent is distilled aot under vacuum, the residue is crystallized from water. alcohol. : -:.::: ... 0.7 g of hemihydrate of 2-utilized-, 6-dihydro-8,9-dimethoxypyrazolo {5,1-o | isoquinoline; M.P. 125-127 C. &%:C62.94; H 6.84; N 12.96. 0.5 HjO Found A: O 62.80; H 6.71; K 12.75, P p me r 5. К 140 мл 31-(б,7-диме ед1асж-3 ,4-дигидро-1-изохинолил)-мети/ -4-ЭГШ1-ff -1,2,4-оксад:иазолинон 5 прилиBEUpt 4 :.л спирта и 1 мл Ю -ного раствора едкого натра и кип т т 2 ч с обратным холодильником. Растворитель отгон ют под вакуумом, к .остатку приливают воду. Получают 81 мг 2 -этиламино-5,6-дигидix i8 .9-димeтoкcщиpaзoлo 5,l«cl изoxинoлинa; т.пл. 114-116 С (из бензина - четырех хлористого углерода). Вычислёно,%: С 65,91; Н 7,01; М 15,3 , Найдено,%: С 65,92; Н 6,93; N 15,13. П р и м е р 6. 10 мл пиридина и 1,9 г хлорида п - толуолсульфокислоты добавл ют к 2,45 г 2-амин(-5,6-дигидро-8,9-диметоксипираэоло 5 ,1-а изохинолина и реакшюнную смесь кип т т 5 мин с обр атным холодильником . После охлаждени  выливакп- реакционную cfyiecb в воду. Получают 3,3 г 2-(4-толуолсул14онилами. но)-5,6-дигндро-8,9-диметокс1тиразоло 5,1-(5 изохинолина; т.пл. 259-261 С (из диоксана). Вычислёно,%: С 60,13; Н 5,29; N 10,52. су,м Найдено,%: С 59,94; Н 5,45;N 10,36. П р и м е р 7. К 2ОО мг 3-(б,7-диметокси-3 ,4-дигидро-1-изохинолил)-метил-5-бензил-1 ,2,4-оксидиазола добавл ютс  5 мл ксилола, и реакционна  смесь кип титр  в течение 8 Ч с флегмой. После охлаждени  Д(эбавл ют 10 мл бензина в смесь. Получают 17 О мг 2-фенйлацетшт-амино-5 ,6-дигидро-8,9-диметоксш1Иразоло 5,1-с« изохинсшина. Точка текучести 225-227 С I.-: . - . .;., -. (дз бутанола). Вычислено,%: с 69,40; Н 5,82; N 11,56. . Найдено,%: С 69,50; Н 5,80; N 11,45. Формула изобретени  1. Способ получени  производных амйно пиразолоизохинолина общей формулы I гДе А - содержаща  1-4 атома углерода алкоксигруппа, IB - атом водорода, содержаща  1-4 атома углерода алканоилгруппа или содер жаща  7-10 атомов углерода ароил- или аралканоилгруппй; Y - атом водорода, и с   тем. или их солей, о т л и ч а ю щ и что соединение обшей формуль П сн-с-и : : - ie( J . / о   А и У имеют указанньте значени , и R обоА начает алкил-,аралки/ь. или арилгруппу, ки т т в среде растворител  с выделением целевого продукта в свободном виде или в виде соли, 2 Способ по п. 1, о т л и ч а ю щ и йс   тем, что дл  получени  соединений ормулы(1), S которых D обозначает алк нои№- ,ароил- или аралканоилгруппу, соединени  форму лы(П ), где А, У и R имек)т указпппые жшчечн , кип т т R уме1юино тепочиой среде. 3. по п. 1, о т л и ч а ю ш и ft. с   тем, что дл  пплучени  соединений фс1. мулы(1, в которых Т) обозначает вопороц , соединени  (П), где А и У л Ь имеют указанные значени , кип т т в сильно щелочной среде.5. To 140 ml of 31- (b, 7-dime e1aszh-3, 4-dihydro-1-isoquinolyl) -methyl / -4-EGSh1-ff -1,2,4-oxad: azolinon 5 when theBEUpt 4: l alcohol and 1 ml of a juicy solution of caustic soda and boil for 2 hours under reflux. The solvent is distilled off under vacuum, and water is added to the residue. Obtain 81 mg of 2-ethylamino-5,6-dihydx i8 .9-dimethoxy 5, l “cl from oxynoline; m.p. 114-116 С (from gasoline - four carbon chloride). Calculated,%: C 65.91; H 7.01; M 15.3, Found,%: C 65.92; H 6.93; N 15.13. EXAMPLE 6 10 ml of pyridine and 1.9 g of p-toluenesulfonic acid chloride are added to 2.45 g of 2-amine (-5,6-dihydro-8,9-dimethoxypyraolo 5, 1-a isoquinoline and the reaction mixture is refluxed for 5 minutes. After cooling, the reaction mixture is poured into water and 3.3 g are obtained with 2- (4-toluenesulononyl. but) -5,6-digndro-8,9-dimethoxy-1-razolo 5,1 - (5 isoquinoline; m.p. 259-261 C (from dioxane). Calculated,%: C 60.13; H 5.29; N 10.52. Su, m; Found: C: 59.94; H 5.45; N 10.36. Example 7: K 2OO mg 3- (b, 7-dimethoxy-3, 4-dihydro-1-isoquinolyl) -methyl-5-benzyl-1, 2, 4-oxydiazole is added 5 ml of xylene, and the reaction mixture bake the titer for 8 hours with reflux. After cooling D (pour 10 ml of gasoline into the mixture. 17 Omg of 2-phenylacetate-amino-5, 6-dihydro-8,9-dimethoxin-1-razolo 5,1-c "iso chinsine Pour point 225-227 C I.-:. -.;.,., -. (Dz butanol). Calculated,%: with 69.40; H 5.82; N 11.56. Found,%: C 69.50; H 5.80; N 11.45. Claim 1. The method of obtaining amino-pyrazoloisoquinoline derivatives of the general formula I gDe A - containing 1-4 carbon atoms alkoxy group, IB - hydrogen atom, containing 1-4 carbon atoms alkanoyl group or containing 7-10 carbon atoms of the aroyl or aralkanoyl group; Y is a hydrogen atom, and so. or their salts, that is, that the compound of the general formulas P cn-c-i:: - ie (J.O.A and Y have the indicated meanings, and R oba begins alkyl-, aralki / ь. or an aryl group, a cyt in a solvent medium with the release of the target product in free form or in the form of a salt, 2 The method according to claim 1, which is to obtain compounds of formula (1), S of which D stands for alkyno-, aroyl, or aralkanoyl, compounds of formula (II), where A, Y, and R have imentales, are boiled in a reusable medium. 3. according to claim 1, about tl and h and y and ft. with the fact that for the irradiation of compounds fs1. the mules (1, in which T) denotes the question, compounds (P), where A and VL and L have the indicated meanings, are boiled in a strongly alkaline medium.
SU762326052A 1972-06-30 1976-02-24 Method of preparing aminopyrazoleisoquinoline derivatives or salts thereof SU591148A3 (en)

Applications Claiming Priority (1)

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HUCI1248A HU167240B (en) 1972-06-30 1972-06-30

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Family Applications (5)

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SU7301941205A SU584782A3 (en) 1972-06-30 1973-06-29 Method of preparing aminoimidazoisoquinoline derivatives or salts thereof
SU7602325957A SU584783A3 (en) 1972-06-30 1976-02-24 Method of preparing aminoimidazoloisoquinoline derivatives or salts thereof
SU762326052A SU591148A3 (en) 1972-06-30 1976-02-24 Method of preparing aminopyrazoleisoquinoline derivatives or salts thereof
SU762325405A SU587863A3 (en) 1972-06-30 1976-02-24 Method of obtaining aminoimidazoisoquinolines or their salts
SU762414099A SU596170A3 (en) 1972-06-30 1976-10-26 Method of preparing aminoimidazoleisoquinoline derivatives or salts thereof

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SU7301941205A SU584782A3 (en) 1972-06-30 1973-06-29 Method of preparing aminoimidazoisoquinoline derivatives or salts thereof
SU7602325957A SU584783A3 (en) 1972-06-30 1976-02-24 Method of preparing aminoimidazoloisoquinoline derivatives or salts thereof

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Application Number Title Priority Date Filing Date
SU762325405A SU587863A3 (en) 1972-06-30 1976-02-24 Method of obtaining aminoimidazoisoquinolines or their salts
SU762414099A SU596170A3 (en) 1972-06-30 1976-10-26 Method of preparing aminoimidazoleisoquinoline derivatives or salts thereof

Country Status (24)

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JP (2) JPS5336480B2 (en)
AR (5) AR208055A1 (en)
AT (1) AT329058B (en)
BE (1) BE801668A (en)
CA (1) CA1014559A (en)
CH (6) CH602729A5 (en)
CS (1) CS179024B1 (en)
DD (1) DD108090A1 (en)
DE (1) DE2332860C2 (en)
DK (1) DK141066B (en)
EG (1) EG11302A (en)
ES (1) ES416971A1 (en)
FI (1) FI55199C (en)
FR (1) FR2190458B1 (en)
GB (1) GB1438819A (en)
HU (1) HU167240B (en)
IL (1) IL42613A (en)
IN (1) IN139710B (en)
NL (1) NL177750C (en)
NO (1) NO138908C (en)
PL (6) PL94059B1 (en)
SE (6) SE405603B (en)
SU (5) SU584782A3 (en)
YU (4) YU36175B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2621037C2 (en) * 2011-09-26 2017-05-31 Санофи Pyrazole quinolinone derivatives, their preparation and therapeutic application

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH603643A5 (en) * 1976-09-29 1978-08-31 Sandoz Ag
HU176214B (en) * 1977-05-18 1981-01-28 Chinoin Gyogyszer Es Vegyeszet Process for producing new 5,6-dihydro-imidazo-square bracket-5,1-a-square bracket closed-isoquinolin derivatives
MXPA01011860A (en) * 1999-05-19 2002-05-06 Procter & Gamble Imidazo-containing heterocyclic compounds, their compositions and uses.
US6552033B1 (en) 2000-05-16 2003-04-22 The Procter & Gamble Co. Imidazo-containing heterocyclic compounds, their compositions and uses

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Publication number Priority date Publication date Assignee Title
CH25A (en) * 1888-11-16 1889-04-05 Saurer & Soehne F Machine for threading needles and for tying threads

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2621037C2 (en) * 2011-09-26 2017-05-31 Санофи Pyrazole quinolinone derivatives, their preparation and therapeutic application

Also Published As

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SE7308998L (en) 1973-12-31
PL96818B1 (en) 1978-01-31
YU299579A (en) 1981-06-30
SU584783A3 (en) 1977-12-15
DD108090A1 (en) 1974-09-05
CS179024B1 (en) 1977-10-31
CH602730A5 (en) 1978-07-31
AR210066A1 (en) 1977-06-30
SE7610170L (en) 1976-09-14
AR209331A1 (en) 1977-04-15
NO138908C (en) 1978-12-06
YU36175B (en) 1982-02-25
FR2190458B1 (en) 1977-04-15
DK141066C (en) 1980-06-30
AR208055A1 (en) 1976-11-30
JPS5336480B2 (en) 1978-10-03
SU584782A3 (en) 1977-12-15
IL42613A (en) 1977-05-31
AT329058B (en) 1976-04-26
DE2332860A1 (en) 1974-03-07
CA1014559A (en) 1977-07-26
EG11302A (en) 1978-06-30
SE431455B (en) 1984-02-06
SU596170A3 (en) 1978-02-28
FR2190458A1 (en) 1974-02-01
AR209330A1 (en) 1977-04-15
ATA563773A (en) 1975-07-15
IN139710B (en) 1976-07-24
SU587863A3 (en) 1978-01-05
SE410189B (en) 1979-10-01
SE425314B (en) 1982-09-20
JPS5334799A (en) 1978-03-31
SE8002538L (en) 1981-10-03
YU299479A (en) 1981-08-31
NL177750C (en) 1985-11-18
DK141066B (en) 1980-01-07
YU179673A (en) 1981-06-30
JPS5740152B2 (en) 1982-08-25
BE801668A (en) 1973-10-15
PL97544B1 (en) 1978-03-30
FI55199B (en) 1979-02-28
PL94046B1 (en) 1977-07-30
DE2332860C2 (en) 1982-12-02
HU167240B (en) 1975-09-27
YU36176B (en) 1982-02-25
CH603647A5 (en) 1978-08-31
PL93702B1 (en) 1977-06-30
IL42613A0 (en) 1973-08-29
YU36177B (en) 1982-02-25
YU36300B (en) 1982-06-18
SE410190B (en) 1979-10-01
PL94059B1 (en) 1977-07-30
JPS4942697A (en) 1974-04-22
SE7610171L (en) 1976-09-14
YU299679A (en) 1981-06-30
FI55199C (en) 1979-06-11
SE420968B (en) 1981-11-09
SE7610169L (en) 1976-09-14
NL177750B (en) 1985-06-17
AR211857A1 (en) 1978-03-31
NL7309104A (en) 1974-01-02
CH603639A5 (en) 1978-08-31
CH602729A5 (en) 1978-07-31
NO138908B (en) 1978-08-28
ES416971A1 (en) 1976-02-16
SE405603B (en) 1978-12-18
GB1438819A (en) 1976-06-09
CH602731A5 (en) 1978-07-31
PL94060B1 (en) 1977-07-30
CH610900A5 (en) 1979-05-15

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