PL115889B1 - Process for manufacturing novel 2-pyridyl-and 2-pyrimidinylaminobenzoic acids - Google Patents

Process for manufacturing novel 2-pyridyl-and 2-pyrimidinylaminobenzoic acids Download PDF

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PL115889B1
PL115889B1 PL1978215270A PL21527078A PL115889B1 PL 115889 B1 PL115889 B1 PL 115889B1 PL 1978215270 A PL1978215270 A PL 1978215270A PL 21527078 A PL21527078 A PL 21527078A PL 115889 B1 PL115889 B1 PL 115889B1
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acids
pyridyl
hooc
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    • 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

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  • 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

Przedmiotem wynalazku jest sposób wytwarza¬ nia nowych kwasów 2-pirydylo- i 2-pirymidyloami- nobenzoesowych ewentualnie w postaci soli wew¬ netrznych lub soli z zasadami, o wartosciowych wlasciwosciach terapeutycznych.Solami wewnetrznymi sa zwiazki w których grupa aminowa wystepuje w postaci jonu amo- niowego, zas grupa karboksylowa w postaci anio¬ nu.Nowym zwiazkom odpowiada wzór 1, w którym A oznacza grupe o wzonze =GH— lub =N—, Ri oznacza atom wodoru, nizsza grupe alkilowa, niz¬ sza grupe alikoksylowa, dokondensowany pierscien benzenowy, lub grupe o wzorze —CO—R4, grupe 15 tetrazolilowa-5 lub grupe cyjanowa w pozycji 4 lub 5, R2 oznacza grupe o wzorze —CO—R4, gru¬ pe tetrazolilowa-5, cyjanowa lub w przypadku gdy Ri oznacza —CO—R4, grupe tetrazolilowa-5, cy¬ janowa w polozeniu 4 lub 5, R2 oznacza równiez ^ wodór, nizsza grupe alkilowa, nizsza grupe alko- ksylowa lub dokondensowany pierscien benzeno¬ wy, R3 oznacza wodór lub nizsza grupe acylowa i R4 oznacza grupe hydroksylowa, aminowa, hy- droksyloaminowa, tetrazolilo-5^aminowa lub nizsza u grupe alikoksylowa.Za nizsze grupy alkilowe, alkoksylowe i acylo- we uwaza sie grupy zawierajace 1—4 atomów wegla, przy czym grupy weglowodorowe moga byc grupami prostymi lub rozgalezionymi, np. gru- w pa metylowa, etylowa, propylowa, izopropylowa, n-butylowa, izobutylowa, trzeciorzedowa butyiowa i odpowiednio grupa alkdksylowa, formylowa, ace- tylowa, propionylowa, butyrylowa.W ramach powyzszych definicji Ri i R2 ozna¬ czaja zwlaszcza wodór, dokondensowany pierscien benzylowy, grupe tetrazolilowa-5 lub karboksylo¬ wa, R3 oznacza zwlaszcza wodór. O ile wystepuja sole z zasadami, to jako te ostatnie skladniki sluza przede wszystkim zasady metali alkalicz¬ nych lub metali ziem alkalicznych, np. wodoro¬ tlenek potasowy lub sodowy lub mocne zasady organiczne, np. nizsze aikiloaminy, etanoloamina, dwu- lub trójetanoloamina.Wedlug wynalazku nowe zwiazki o wzorze 1 wytwarza sie przez traktowanie zwiazku o wzo¬ rze 2, w którym Rj i R2 maja wyzej podane zna¬ czenie, substancjami zasadowymi. Dla otworzenia pierscienia moga sluzyc substancje zasadowe, w szczególnosci alkalia, np. lug sodowy, lug pota¬ sowy, przy czym temperatura reakcji wynosi ko¬ rzystnie od temperatury pokojowej do tempera¬ tury wrzenia mieszaniny reakcyjnej.Produkty wyjsciowe mozna otrzymywac znany¬ mi jako takie sposobami ewentualnie sposobem opisanym w opisie patentowym RFN nr 25 57 425.Otrzymywane sposobem wedlug wynalazku no¬ we zwiazflri maja zastosowanie terapeutyczne lub moga sluzyc jako produkty posrednie w wytwa- 115 889115 889 rzaniu leków. Nalezy podniesc tu ich dzialanie pnzeciwalergiczne. Moze ono byc wykorzystane w profilaktyce i do traktowania chorób alergicznych, takich jak astma lub goraczka sienna, conjuncti- vitis, pokrzywka, egzemy, uczuleniowe zapalenie skóry. Nowe zwiazki wykazuja przy tym dziala¬ nie rozluzniajace miesnie (rozszerzajace oskrzela) i rozszerzajace naczynia. Przy najwazniejszym sto¬ sowaniu, w profilaktyce astmy, nalezy wymienic jako znaczne korzysci w stosunku do produiktu handlowego kwasu krcmoglicynowego, dluzszy czas dzialania i przede wszystkim aktywnosc przy po¬ dawaniu doustnym.Otrzymywane sposobem wedlug wynalazku zwia¬ zki przerabia sie w znany sposób na galenowe formy uzytkowe z substancjami pomocniczymi i nosnikami, np. na kapsulki, tabletki, drazetki, roz¬ twory, zawiesiny do stosowania doustnego, na aero-i zole do podawania plucnego, na sterylne izoto- niezne wodne roztwory do stosowania pozajelito¬ wego i na kremy, mascie, lotiony, emulsje lub spray'e do stosowania lokalnego.Dawka jednostkowa zalezy od wskazan, np. ja¬ kosci stanu alergicznego. Na ogól dawka na 1 kg ciezaru ciala wynosi przy stosowaniu de pluc od okolo 20—500 ^g, przy stosowaniu dozylnym od okolo 0,2 do 10 mg, przy doustnym stosowa¬ niu od okolo 1 do 50 mg. Do nosa lub oka sto¬ suje sie od okolo 0,5 do 25 mg.Nastepujace przyklady wyjasniaja sposób wy¬ twarzania wedlug wynalazku. Widma w nadfio- lesie wykonywano fotometrem spektralnym (Spek- tralfotometer DMR 21 firmy Zeiss, Oberikochen).Kazdorazowo dokladnie odwazano 10—20 mg sub¬ stancji, a w przypadku substancji oznaczonych za pomoca x rozpuszczono je wzglednie rozcienczono 10 ml sulfotlenku dwumetylu rozpuszczonego w 0,01 n lugu sodowym. Wybrano dlugofalowe pas-r ma absorpcyjne. Absorpcje w majlcsymuim postaly podane jako X max/nm/ z naleznym molowym logarytmicznym wspólczynnikiem ekstynkcji jako log $.Przyklad J. Sól dwusodowa kwasu 4-/2*piry- dyloamjno/^izoftailowego o wzorze 3. 5,24 g soli sodowej kwasu ll-H-ll-keto-pirydo/ /2,l-b/chinazolino-l2-karboksylowego ogrzewa sie z 20 ml In lugu sadowego przez 1 godzine na laz¬ ni wodnej. Powstaje przezroczysty zólty roztwór.Nastepnie odciaga sie azeotropowo wode 3 chloro¬ formem. Krysztaly wylugowuje sie mala iloscia eteru, odciaga i suszy w prózni w temperatu¬ rze 60°C.Analiza: C13H8N204Na2 X 2H20 Wr H*/p N*/o H»OVt wyliczono: 46,15 3,55 8,28 10,65 znaleziono: 46,04 3,34 8,15 11,16 Widmo w nadfiolecie X max log b 288 ram 323 ran 4,1S 4,30 10 15 lugu sodowego do tempertury 70°C, Nastepnie od- destylowuje sie wode. Krysztaly wylugowuje sie mala iloscia eteru, odciaga i w temperaturze 60°C suszy w prózni.Awaliza: C15H8Ne02Na| X C*/o wyliczono: 41,05 znaleziono: 41,98 Widmo w nadfiolecie X m log Analogicznie wytwarza sie sól dwupotasowa kwa¬ su 4-/2-|pirydylc^imino/-izoftalowego o wzorze 5.Widimo w nadfiolecie: X max &I90 nm 332 nm log e 4,21 4,32 oraz zwiazki wymienione w nastepujacej tablicy jako sole sodowe, przy czym podane dane widm w nadfiolecie odnosza sie do soli Na: 3H20 H»/o 3,09 3,54 ax 290 nm e 4,14 N»/» 12,10 «,18 317 nm 4,27 Przyklad U. Sól dwusodowa kwasu 2-/2-piry-* dyloammoAS-ZlK-tetraKolilo^S/ben^oesoweigo o wzo~ rze 4 9 g ll^-UHketo-piry^o/2,lHb/-2-/lJi-te^ra^cililo-&^ -chinazoliny ogpzewa sie przez 2 godziny z 60fi ml Nr l 1 2 3 4 5 6 7 8 * Zwiazek 8 ester imonome- tylowy kwasu 4-/2Hpirydylo- amaino/nizofta- lQW€gQ fcwas 4-/2^chi- nolinylo-ami- noMzoftalowy kwas 6-/2-ka boksy-4-meity- lo^feflyloaini-r ao/«niftEotyno- wy l~mai*amid kwasu 4-/2-piU xy4ykmn\mh nsoftatewego kwas 5-cyjano- -2-/2Hpirydylo- aminoMranzo^ $gowy fydyloamkio/- »laoftaletwy iThydroksam?o- wy kwa« WSnpi- ry"dyloaimiivo/- kfcrgftalewy |fewa» 0-/&-fcar<* tooJtiy-4-meto- !fcsy*enyloaml- teo/-n&oty*io- wy fcwae e«£-fcar- boksy--2-nafty« 4oaniino/*aife0-- lykowy Wzór struktu¬ ralny 3 wzór 6 wzór 7 wtór 8 wzór & wz.$r 10 wsór U i WEOT 13 wzór 13 wzór 14 Widmo w nad- 1 fiolecie 1 X max log e (nm) 4 288 324 292 355 aao 283 320 295 324 2W 334 asa 379 310 279 3*e 4,18' 4,40 4,32 4,34 W5 4413 4,37 4JS 4»39 4,ao «a m 4JL4 Ut 4,3S 4,32115 889 1 10 11 12 13 L 14 15 2 kwas 4-/2npi- rymidyloami- no/-izoftalowy kwas 4-/5-aini- no-2-pirydylo- amino/-izofta- iiowy kwas 4-/5-ace- tamido^^iry- dyloamino/- -izoftalowy 4-/2^pirydylo- amino/-izoita- lowy^mono-N- -/lH-tetrazoli- lo-5/-karboksy- amid kwas 6-/2-kar- boksyfenylo- arnino/-nikoty- nowy kwas N-acety- lo-N-/2-p;irydy- io/-4^aminoizo- ftalowy 3 wzór 15 wzór 16 wzór 17 wzór 18 wzór 19 wzór 20 4 | 288 325 298 338 298 335 290 330 325 265 4,23 4,32 | 4,31 4,19 | 4,25 4,30 1 4,17 4,43 4,30 3,95 6 Zastrzezenie patentowe 10 15 20 Sposób wytwarzania nowych kwasów 2^pirydylo- i 2-pkym'idyloaminobeozoesowych o wzorze 1, w którym A oznacza grupe o wzorze =CH lub =N—, Rj oznacza wodór, nizsza grupe alkilowa, nizsza grupe aflkoksylowa, dokondensowany pierscien ben¬ zenowy, lub grupe o wzorze —CO—R4, grupe te- trazolilowa-5, cyjanowa w pozycji 4 lub 5, R2 oz¬ nacza grupe o wzorze —CO—R4, grupe tetrazoli- lowa-5, cyjanowa lub, w przypadku gdy Ri ozna¬ cza —CO—R4, grupe tetirazolilowa-5 lub cyjano¬ wa w pozycji 4 lub 5, R2 oznacza równiez wodór, nizsza grupe alkilowa, nizsza grupe alkoksylowa lub dokondensowany pierscien benzenowy, R3 oz¬ nacza wodór lub nizsza grupe acylowa i R4 ozna¬ cza grupe hydroksylowa, aminowa, hydroksyloami- nowa, tetrazodilo-5-aminowa lub nizsza grupe al¬ koksylowa, ewentualnie w postaci wewnetrznych soli lub soli z zasadowymi skladnikami, znamien¬ ny tym, ze zwiazek o wzorze 2, w którym Ri, R2 i A maja wyzej podane znaczenie traktuje sie substancjami zasadowymi otrzymane sole z zasa¬ dami ewentualnie przeprowadza w sole wewnetrz¬ ne, sole wewnetrzne ewentualnie przeksztalca w sole z zasadami.WZÓR 1 C02Na ^J)~C02Na x 2^ .--R.WZ0R 3115 889 CCLNa ^_N \L. N-N fi \.mJr\-i U x 3 H20 \=/ ^=J N-N Na WZÓR A C02K f"VNH-^-C02K WZÓR 5 a HOOC COOCH3 NH ^ WZÓR 6 HOOC ^ COOH '„XT WZÓR 7 ChL COOH . COOH NH A^ WZÓR 8 HOOC .C - NH2 C^NH^J WZÓR 9115 889 HOOC CN nh ^^y WZÓR 10 o HOOC C-NH-OH NH WZÓR 11 ^ HOÓC W20R 12 CH30 COOH CÓOH N ¦ i j ^\ NH ^ WZÓR 13 COOH COOH NH -^^ WZÓR HOOC N COOH *N^ NH WZÓR 15115 889 H2N HOOC COOH NH '"^ W2ÓR 13 Hg-C-NH.N HOOC _. COÓH NH WZÓR 17 HOOC NH O II N.m C-NH-C '•¦' N-N H W20R 18 HOOC N HOOC NH WZÓR 19 HOOC ,-^N L^JJ—M 1! OC - CH.COOH WZÓR 20 DN-3, z. 160/82 Cena 100 cl PL PL PL PL PL PL PL PL PL PL PL

Claims (1)

1.
PL1978215270A 1977-08-10 1978-08-09 Process for manufacturing novel 2-pyridyl-and 2-pyrimidinylaminobenzoic acids PL115889B1 (en)

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

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PL115889B1 true PL115889B1 (en) 1981-05-30

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PL1978208942A PL115778B1 (en) 1977-08-10 1978-08-09 Process for preparing novel 2-pyridyl-and 2-pyrimidylaminobenzoic acids
PL1978215270A PL115889B1 (en) 1977-08-10 1978-08-09 Process for manufacturing novel 2-pyridyl-and 2-pyrimidinylaminobenzoic acids

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AT (1) AT370415B (pl)
AU (1) AU520240B2 (pl)
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BG (1) BG30472A1 (pl)
CA (1) CA1111037A (pl)
CH (1) CH649289A5 (pl)
CS (1) CS202506B2 (pl)
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DE (1) DE2735919A1 (pl)
DK (1) DK148019C (pl)
ES (5) ES472143A1 (pl)
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FR (1) FR2400017A1 (pl)
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HU (1) HU179933B (pl)
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PL (2) PL115778B1 (pl)
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SU (2) SU735168A3 (pl)
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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
DE3682160D1 (de) * 1985-10-16 1991-11-28 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

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GB1162287A (en) * 1967-11-07 1969-08-20 Union Pharma Scient Appl New Salts of 2-Anilino-Nicotinic Acids
GB1264798A (pl) * 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.

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IT1107960B (it) 1985-12-02
ZA784501B (en) 1980-04-30
AU3877278A (en) 1980-02-14
GB2002764B (en) 1982-08-04
PT68407A (de) 1978-09-01
IT7850642A0 (it) 1978-08-08
PH19117A (en) 1986-01-06
DK351978A (da) 1979-02-11
FI71555B (fi) 1986-10-10
NO782707L (no) 1979-02-13
ES480623A1 (es) 1980-01-01
JPS6231704B2 (pl) 1987-07-09
US4241068A (en) 1980-12-23
ATA549278A (de) 1982-08-15
CA1111037A (en) 1981-10-20
MX5672E (es) 1983-12-08
CH649289A5 (de) 1985-05-15
IE781618L (en) 1979-02-10
NO152605C (no) 1985-10-23
AT370415B (de) 1983-03-25
LU80094A1 (de) 1979-09-07
PL208942A1 (pl) 1979-12-03
BE869640A (fr) 1979-02-09
SU886743A3 (ru) 1981-11-30
BG30472A1 (en) 1981-06-15
JPS5430177A (en) 1979-03-06
AU520240B2 (en) 1982-01-21
DK148019C (da) 1985-07-01
SE7808530L (sv) 1979-02-11
NL7808319A (nl) 1979-02-13
SE444170B (sv) 1986-03-24
ES480622A1 (es) 1980-01-01
YU40832B (en) 1986-06-30
SU735168A3 (ru) 1980-05-15
DD140351A5 (de) 1980-02-27
NZ188101A (en) 1981-01-23
GR65024B (en) 1980-06-16
FI782039A7 (fi) 1979-02-11
HU179933B (en) 1983-01-28
IE47228B1 (en) 1984-01-25
ES475456A1 (es) 1979-05-01
ES475457A1 (es) 1979-11-16
NO152605B (no) 1985-07-15
DE2735919C2 (pl) 1988-10-27
YU191678A (en) 1983-01-21
ES472143A1 (es) 1979-03-16
FI71555C (fi) 1987-01-19
DK148019B (da) 1985-02-04
FR2400017B1 (pl) 1983-03-11
DE2735919A1 (de) 1979-02-22
FR2400017A1 (fr) 1979-03-09
CS202506B2 (en) 1981-01-30
GB2002764A (en) 1979-02-28
PL115778B1 (en) 1981-04-30

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