SU735168A3 - Способ получени циклической карбоновой кислоты или ее соли - Google Patents

Способ получени циклической карбоновой кислоты или ее соли Download PDF

Info

Publication number
SU735168A3
SU735168A3 SU782646404A SU2646404A SU735168A3 SU 735168 A3 SU735168 A3 SU 735168A3 SU 782646404 A SU782646404 A SU 782646404A SU 2646404 A SU2646404 A SU 2646404A SU 735168 A3 SU735168 A3 SU 735168A3
Authority
SU
USSR - Soviet Union
Prior art keywords
group
salt
hydrogen
carbon atoms
alkyl
Prior art date
Application number
SU782646404A
Other languages
English (en)
Inventor
Шромм Курт
Ментруп Антон
Рент Эрнст-Отто
Фюгнер Армин
Якоби Фолькер
Original Assignee
К.Х.Берингер Зон (Фирма)
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 К.Х.Берингер Зон (Фирма) filed Critical К.Х.Берингер Зон (Фирма)
Application granted granted Critical
Publication of SU735168A3 publication Critical patent/SU735168A3/ru

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Medicinal Preparation (AREA)

Description

3 ---;;--- ; 7 где R - алкил; асуб - ашшыт  группа; , П}иР2-имеют вышеуказаншле значени , подвергают окксленшо с последующим выделешшм целевого продукта в виде кислоты или ее соли или сн тием N-адильной группы. Окисле1ше тгрсвод т с помощью сильных окислителей, таких, как например перманганат кЗ ЛИЯ в водном растворе с добавкой сульфата магни . Реакцию провод т в интервале температур от комнатной до температуры кипетш  реакционной смеси. Oimeivieime .N-aцилгpyшIЬI можно проводить омылением, шпример, гидроокисью кали . Исходное соединение формулы (И) может быть получено известными способами, например путем взаимодействи  2-галогенш1ридинов с о-толуидинщ)ого1зодными и последующего аци лйровада . Предлагаемые соединего1  могут быть и споль зованы дл  терапевтических целей или служить в качестве промежуточных продуктов дл  полу чени  лекерствешплх веществ. Они про вл ют. антиаллергическое действие, которое может быт использовано в профилактике и дл  аллергических заболеваний, тйких как астма, сенна  лихорадка, коньюнктивит, крапивна  лихорадка, экземы, атонический дерматит. Эти соединегаш имеют также бронхорасагар ющее и сосудорасцщр ющее действи . В профилактик астмы они по сравнению с известным прешратом (кромоглвдинрва  кислота) обладают более длительным дейстеием и эффективностью при применении. Эффективна  доза зависит от назначени , напр1шер от ввда аллергического состо ни  и составл ет при легочном введении 20-500 мг/к при внутрийенном введении - 0,2-10 мг/кг, при оральном применении - 1-50 мг/кг, при гтазначешш в йос или глаза - 0,5-25 мг/кг. Пример 1. Дикалиева  соль 4-(2-пнр1У1Ш1амино )-изофталевой кислоты 4,8 г N-(2-ш pидил)-2,4-димeтилaцeтaнилидa (т.пл. 46-50С), получаемого из 2-хлоршфидина и 2,4-диметиланилина при 160-170°С, ацетилируют с ацетангидрвдом. 2,4 г сульфата магни  раствор ют в воде. В нагретый до 30С раствор порци ми добавл ют 12,64 г перманганата кали . Затем в течение 2 ч перемешивают при 80-90°С, образующуюс  двуокись марганца быстро OTCBV сывают и промывают водой. После упаривани  раствора до объема 50 мл разбавл ют 50 мл этанола и выделившийс  сульфат кали  отсасывают . Спиртово-водный раствор утривают в вакууме , остаток этанолом и просщм: эфиром довод т до кристаллизации. Выход 4,4 г (54,6% теории). 1 г полученной таким образом дикалиевойсоли М-адетил-М- (2-пиридил) -4-аминоизофталевой кислоты с 0,4 г едкого кали в 10 мл водь в течение 2 ч кип т т с обратным холодильником и остаток растирают с этанолом и, простым эфиром, дикалиева  соль 4-(2-1Шридиламино)-изофталевой кислоты (спектр. ЯМР служит дл  характеристики) при этом кристаллгоуетс . Выход 0,8 г (96% теории). Аналогично получают приведенные в таблще соединени  (в виде натриевых солей).
6- (2-Карбокси- 4-метоксифенил- амино)-никотинова  кислота
ЪГН N-бутил- N- (2-пиридил) -4-аминоизофталева  кислота
Ы-1фопионил-М- (2-гшридил) -2-амино-5- (1 Н-тетразолил-5) беюойна  кислота
Продолжегше таблт
НО 2(5
36
00-СН2-СНз ОС- dHz-dHg-uHj
HOgti
N-Ацетил-N- (5-карбокси-2-пиридил ) -2-аминобензой а  -KHcrfoTa
НОгб
55 N-OopMioi-N- (2-пирйдил)-4-аминоизоf фталева  кислота)
6- (2-Карбоксифениламино ) -никотинова  кислота
НО
75
325
нн Od-СНз
Цродопжение таблицы

Claims (1)

  1. Формула изобретения
    Способ приучения циклической карбоновой кислоты общей формулы (I)
    Соон где А — группа — СП— или -N—,
    Ri - водород, алкил или алкоксил с 1-4 атомами углерода, приконденсированное бензольное кольцо, цианогруппа, находящаяся в положении 4 или 5, тётразолил-5, груши —СО—R4; 1 Rj — группа -4COR4, те1разолил-5даано-, груши, или, если Rj является группой -C0R4, тетразолилом-5, или цианогруппОй, находящейся в положении 4 или· 5 5, то R2 — водород, алкил или алкоксил с 1-4 атомами углерода или приковденсированное бензольное кольцо;
    R3 — водород или ацил с 1-4 атомами углерода; 1
    R4 - окси-, амино-, гидроксиламино-, 5-тетразолиламиногруппа или алкоксил с 1-4 атомами углерода, или ее соли, отличают иЛ с я тем, что соединение общей формулы (II)
    R где R — алкил, асу£ - ацильная группа;
    A, Rj й R2 имеют вышеуказанные значения, подвергают окислению с последующим выделением целевого продукта в виде кислоты или соли, или снятием N-ацильной группы.
SU782646404A 1977-08-10 1978-08-08 Способ получени циклической карбоновой кислоты или ее соли SU735168A3 (ru)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19772735919 DE2735919A1 (de) 1977-08-10 1977-08-10 Neue 2-pyridyl- und 2-pyrimidylaminobenzoesaeuren

Publications (1)

Publication Number Publication Date
SU735168A3 true SU735168A3 (ru) 1980-05-15

Family

ID=6016013

Family Applications (2)

Application Number Title Priority Date Filing Date
SU782646404A SU735168A3 (ru) 1977-08-10 1978-08-08 Способ получени циклической карбоновой кислоты или ее соли
SU792765447A SU886743A3 (ru) 1977-08-10 1979-05-21 Способ получени солей щелочных металлов производных 2-пиридил- или 2-пиримидиламинобензойной кислоты

Family Applications After (1)

Application Number Title Priority Date Filing Date
SU792765447A SU886743A3 (ru) 1977-08-10 1979-05-21 Способ получени солей щелочных металлов производных 2-пиридил- или 2-пиримидиламинобензойной кислоты

Country Status (32)

Country Link
US (1) US4241068A (ru)
JP (1) JPS5430177A (ru)
AT (1) AT370415B (ru)
AU (1) AU520240B2 (ru)
BE (1) BE869640A (ru)
BG (1) BG30472A1 (ru)
CA (1) CA1111037A (ru)
CH (1) CH649289A5 (ru)
CS (1) CS202506B2 (ru)
DD (1) DD140351A5 (ru)
DE (1) DE2735919A1 (ru)
DK (1) DK148019C (ru)
ES (5) ES472143A1 (ru)
FI (1) FI71555C (ru)
FR (1) FR2400017A1 (ru)
GB (1) GB2002764B (ru)
GR (1) GR65024B (ru)
HU (1) HU179933B (ru)
IE (1) IE47228B1 (ru)
IT (1) IT1107960B (ru)
LU (1) LU80094A1 (ru)
MX (1) MX5672E (ru)
NL (1) NL7808319A (ru)
NO (1) NO152605C (ru)
NZ (1) NZ188101A (ru)
PH (1) PH19117A (ru)
PL (2) PL115778B1 (ru)
PT (1) PT68407A (ru)
SE (1) SE444170B (ru)
SU (2) SU735168A3 (ru)
YU (1) YU40832B (ru)
ZA (1) ZA784501B (ru)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3100516A1 (de) * 1981-01-10 1982-08-12 C.H. Boehringer Sohn, 6507 Ingelheim Pyridylaminobenzoesaeuren, ihre herstellung und verwendung
FR2533567A1 (fr) * 1982-09-23 1984-03-30 Ki I Farmakologii 2-(orthocarboxyphenylamino)-6h-pyrimido (2,1-b)-quinazolone-6 et ses derives, leur procede de preparation et leur application therapeutique
US4610991A (en) * 1983-04-18 1986-09-09 Sterling Drug Inc. Antihypertensive pyridylaminobenzamide compounds
JPS60100559A (ja) * 1983-11-05 1985-06-04 Morishita Seiyaku Kk ２−アニリノ−１，６−ジヒドロ−６−オキソ−５−ピリミジンカルボン酸誘導体，その製法及び該化合物を含有する抗アレルギ−剤
US4584379A (en) * 1985-01-22 1986-04-22 Merrell Dow Pharmaceuticals Inc. Isoquinoline thromboxane synthetase inhibitors
ATE68789T1 (de) * 1985-10-16 1991-11-15 Merck Frosst Canada Inc 2-substituierte chinoline.
GB9615950D0 (en) * 1996-07-30 1996-09-11 Univ Warwick Variable reluctance machines
US6022884A (en) 1997-11-07 2000-02-08 Amgen Inc. Substituted pyridine compounds and methods of use

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1064259A (en) * 1963-12-19 1967-04-05 Union Pharma Scient Appl New derivatives of 2-anilino-nicotinic acid and process for their preparation
GB1162287A (en) * 1967-11-07 1969-08-20 Union Pharma Scient Appl New Salts of 2-Anilino-Nicotinic Acids
GB1264798A (ru) * 1968-07-10 1972-02-23
ES416847A1 (es) * 1973-07-12 1976-03-01 Hermes Sa Lab Procedimiento para la obtencion de derivados del acido ni- cotinico.

Also Published As

Publication number Publication date
NO782707L (no) 1979-02-13
CH649289A5 (de) 1985-05-15
CA1111037A (en) 1981-10-20
PL115778B1 (en) 1981-04-30
ZA784501B (en) 1980-04-30
DK148019C (da) 1985-07-01
BE869640A (fr) 1979-02-09
DD140351A5 (de) 1980-02-27
ATA549278A (de) 1982-08-15
ES472143A1 (es) 1979-03-16
IE781618L (en) 1979-02-10
YU191678A (en) 1983-01-21
HU179933B (en) 1983-01-28
DK148019B (da) 1985-02-04
AT370415B (de) 1983-03-25
PL115889B1 (en) 1981-05-30
JPS5430177A (en) 1979-03-06
JPS6231704B2 (ru) 1987-07-09
FI71555C (fi) 1987-01-19
SE7808530L (sv) 1979-02-11
NO152605B (no) 1985-07-15
BG30472A1 (en) 1981-06-15
AU3877278A (en) 1980-02-14
FI782039A (fi) 1979-02-11
DE2735919A1 (de) 1979-02-22
GR65024B (en) 1980-06-16
LU80094A1 (de) 1979-09-07
PH19117A (en) 1986-01-06
FI71555B (fi) 1986-10-10
SU886743A3 (ru) 1981-11-30
GB2002764A (en) 1979-02-28
ES475456A1 (es) 1979-05-01
NL7808319A (nl) 1979-02-13
AU520240B2 (en) 1982-01-21
NZ188101A (en) 1981-01-23
FR2400017B1 (ru) 1983-03-11
IT7850642A0 (it) 1978-08-08
GB2002764B (en) 1982-08-04
DE2735919C2 (ru) 1988-10-27
CS202506B2 (en) 1981-01-30
NO152605C (no) 1985-10-23
SE444170B (sv) 1986-03-24
PL208942A1 (ru) 1979-12-03
MX5672E (es) 1983-12-08
US4241068A (en) 1980-12-23
ES475457A1 (es) 1979-11-16
DK351978A (da) 1979-02-11
ES480622A1 (es) 1980-01-01
PT68407A (de) 1978-09-01
IE47228B1 (en) 1984-01-25
FR2400017A1 (fr) 1979-03-09
IT1107960B (it) 1985-12-02
YU40832B (en) 1986-06-30
ES480623A1 (es) 1980-01-01

Similar Documents

Publication Publication Date Title
NO147450B (no) Analogifremgangsmaate for fremstilling av terapeutisk aktive kinazolonderivater.
JPH01246265A (ja) ４‐ピリドン‐３‐カルボン酸誘導体
DE19542189A1 (de) Cyclische N-substituierte alpha-Iminohydroxamsäuren
EP0011142B1 (de) Pyrido (2,1-b) chinazolinon-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate
SU735168A3 (ru) Способ получени циклической карбоновой кислоты или ее соли
CH639662A5 (de) Imidazoazine und imidazodiazine.
RU2281282C2 (ru) Производное пиридин-1-оксида и способы его преобразования в фармацевтически эффективные соединения
DE2654215A1 (de) 3,4-dihydrochinazolinderivate, verfahren zu ihrer herstellung und sie enthaltendes pharmazeutisches mittel
FI63573C (fi) Foerfarande foer framstaellning av oxibensotiazin-dioxiders kaboxamider
US3753997A (en) Trifluoromethly substituted-2,6-diphenyl-4-pyridyl carbinolamine antimalarials
US3979399A (en) Amino derivatives of pyrazolopyridine carboxamides
JPS58146566A (ja) ピリジン誘導体
DE3885482T2 (de) Pyridyloxy-Derivate.
DE2536003A1 (de) Neue pyrazol-derivate, ihre herstellung und verwendung
EP0114572A1 (de) Substituierte Imidazo(1,5-a)pyridine
CH616934A5 (en) Process for the preparation of chromone derivatives
DE3872576T2 (de) Leukotrienantagonisten.
DE4417705A1 (de) Substituierte Furoxane
CH641457A5 (de) Azepino(1,2,3-lm)-beta-carbolin-verbindungen, verfahren zu deren herstellung und arzneimittel, welche die verbindungen enthalten.
US4330543A (en) Imidazoazines and imidazodiazines
KR820001518B1 (ko) 2-피리딜 및 2-피리미딜아미노 벤조산류의 제조방법
KR810000613B1 (ko) 퀴나졸론 유도체의 제조방법
US2493645A (en) Nicotinic acid-beta-picolyl-amide and process for the manufacture thereof
US2381873A (en) 6-amino nicotinamide derivatives
US4134981A (en) Pyrimidal [2,3,d]Pyrimidin-4(3H)-ones as antiallergy agents