FI66000C - Foerfarande foer framstaellning av terapeutiskt aktiva 2-amino-4-pyrimidonderivat - Google Patents

Foerfarande foer framstaellning av terapeutiskt aktiva 2-amino-4-pyrimidonderivat Download PDF

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Publication number
FI66000C
FI66000C FI790435A FI790435A FI66000C FI 66000 C FI66000 C FI 66000C FI 790435 A FI790435 A FI 790435A FI 790435 A FI790435 A FI 790435A FI 66000 C FI66000 C FI 66000C
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Prior art keywords
mixture
pyrimidone
give
group
compound
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FI790435A
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English (en)
Finnish (fi)
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FI790435A (fi
FI66000B (fi
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Thomas Henry Brown
Robert John Ife
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Smith Kline French Lab
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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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • 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
    • C07D213/61—Halogen atoms or nitro radicals
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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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)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Nutrition Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Claims (6)

1. Förfarande för framställning av ett terapeutiskt aktivt 2-amino-4-pyrimidonderivat med formeln 0 JT\ Il j m D^^X^^CH -Y-CH CH-NH Z H och ett farmaceutiskt acceptabelt syraadditionssalt därav, i vilken formel 12 12 D är en väteatom eller R R N-CKL·-, väri R och R är väte- ^ 12 atomer eller lägre alkylgrupper eller R och R bildar till-saimans med den kväveatora vid vilken de är bundna en pyrrolidon-eller piperidinogrupp; X är syre eller svavel; Y är svavel eller syre; B är en pyridyl- eller N-oxo-pyridylgrupp, vilka grupper möj-ligen är substituerade med en eller flera lägre alkyl-, lägre alkoxi- eller hydroxigrupper,eller B är en furyl-, kinolyl-, tienyl-, 4- eller 5-(1,3-benzodioxolvl)grupp eller fenylgrupp, som möjligen är substituerad med en eller flera halogen-, hydr-oxi- eller di(lägre alkyl)aminogrupper, kännetecknat av att man omsätter ett pyrimidon med formeln O JL J Q N' H 1 väri B har samma betydelse som B eller är ett skyddat derivat av B och Q är en nitroamino- eller lägre alkyltiogrupp, med en amin med formeln 65000 37 JT\ U> Z Z £. z eller förutsatt att Y är svavel, med en förening GSCI^CI^Ni^, väri G är en väteatom eller en skyddsgrupp för tiolgruppen, varefter produkten omsätts med en förening med formeln H) D ' X CH2L väri L är en med tiol substituerbar grupp; och därefter, om nödvändigt: i) avlägsnas alla skyddsgrupper, ii) förutsatt att B ej är en furyl- eller tienylgrupp, omsätts möjligen produkten, väri D är en väteatom med en Mannich- 12 reagens, varvid en förening, väri D är R R NCH_- erhalls, 1 ^ 2 iii) omsätts möjligen produkten, väri R eller R är en väte- atom med formaldehyd och myrsyra, varvid en förening, väri R 2 eller R är metyl, erhalls, iv) bildas ett farmaceutiskt acceptabelt syraadditionssalt.
2. Förfarande enligt patentkravet 1,kanne tecknat av att man framställer en förening med formeln 1, väri D är en dimetvlaminometylgrupp och X är en syreatom.
3. Förfarande enligt patentkravet 1 eller 2, kanne -tecknat av att man framställer en förening med formeln 1, väri B är en pyridylring, som möjligen är substituerad med en lägre alkyl- eller lägre alkoxigrupp.
4. Förfarande enligt patentkravet 1, kännetecknat av att man framställer 2-/2-(5-dimetylaminometyl-2-furylmety1-tio) etylamino7-3- (6-metyl -3-pyridylmety.1) -4-pyrimidon.
5. Förfarande enligt patentkravet 1,kännetecknat av att man framställer en förening med formeln 1, väri B är en kinolyl- eller dimetylpyridylgrupp.
FI790435A 1978-02-13 1979-02-09 Foerfarande foer framstaellning av terapeutiskt aktiva 2-amino-4-pyrimidonderivat FI66000C (fi)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB574078 1978-02-13
GB574078 1978-02-13
GB2283478 1978-05-25
GB2283478 1978-05-25
GB7844259 1978-11-13
GB7844259 1978-11-13

Publications (3)

Publication Number Publication Date
FI790435A FI790435A (fi) 1979-08-14
FI66000B FI66000B (fi) 1984-04-30
FI66000C true FI66000C (fi) 1984-08-10

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Application Number Title Priority Date Filing Date
FI790435A FI66000C (fi) 1978-02-13 1979-02-09 Foerfarande foer framstaellning av terapeutiskt aktiva 2-amino-4-pyrimidonderivat

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US (2) US4234588A (sv)
EP (1) EP0003677B1 (sv)
JP (1) JPS54115385A (sv)
AR (1) AR223476A1 (sv)
AT (1) AT372087B (sv)
AU (1) AU531757B2 (sv)
BG (1) BG34906A3 (sv)
CA (1) CA1147335A (sv)
DD (1) DD142052A5 (sv)
DE (1) DE2961289D1 (sv)
DK (1) DK54879A (sv)
EG (1) EG13747A (sv)
ES (1) ES477667A1 (sv)
FI (1) FI66000C (sv)
HK (1) HK15487A (sv)
HU (1) HU180945B (sv)
IE (1) IE48313B1 (sv)
IL (1) IL56611A (sv)
IN (1) IN151188B (sv)
IT (1) IT1119272B (sv)
MX (1) MX5926E (sv)
MY (1) MY8500590A (sv)
NO (1) NO151546C (sv)
NZ (1) NZ189592A (sv)
PH (2) PH18073A (sv)
PL (1) PL118708B1 (sv)
PT (1) PT69203A (sv)
RO (1) RO83454A (sv)
SG (1) SG61782G (sv)
SU (1) SU999971A3 (sv)
YU (1) YU29279A (sv)

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US4584384A (en) * 1978-05-30 1986-04-22 Smith Kline & French Laboratories Limited Nitro pyrroles
ZA793392B (en) * 1978-07-15 1980-08-27 Smith Kline French Lab Isoureas and isothioureas
ZA793443B (en) * 1978-07-26 1980-12-31 Glaxo Group Ltd Heterocyclic derivatives
YU53681A (en) * 1980-03-08 1983-12-31 Smith Kline French Lab Process for obtaining 5-dimethylamino-methyl-2-furane methanol
CA1155842A (en) * 1980-03-29 1983-10-25 Thomas H. Brown Compounds
ZW21281A1 (en) * 1980-10-01 1981-11-18 Smith Kline French Lab Amine derivatives
US4439609A (en) * 1980-10-01 1984-03-27 Smith Kline & French Laboratories Limited Pyridines
US4352933A (en) * 1981-02-06 1982-10-05 Smithkline Beckman Corporation Chemical methods and intermediates for preparing substituted pyrimidinones
US4439437A (en) * 1981-04-28 1984-03-27 Smith Kline & French Laboratories Limited 2-[2-Thiazolyl or 2-guanidino-4-thiazolyl methylthioethyl(or butyl)amino]-3-(hydroxy or carboxy)pyridines, compositions containing same and method of use
ZA823149B (en) * 1981-05-27 1983-03-30 Smithkline Beckman Corp Chemical process
IE53193B1 (en) * 1981-07-14 1988-08-17 Smithkline Beckman Corp Preparation of lower alkyl 2-formyl-3-(6-methyl-3-pyridinyl)-propionates
WO1983002113A1 (en) * 1981-12-17 1983-06-23 Yuki, Hiroshi Propenylamine derivatives and drug containing same
CA1211111A (en) * 1982-02-15 1986-09-09 Isao Yanagisawa Process for preparing novel pyrimidone compounds
US4808589A (en) * 1982-02-20 1989-02-28 Smith Kline & French Laboratories Limited Pyrimidone derivatives
DE3362182D1 (en) * 1982-07-20 1986-03-27 Smith Kline French Lab A process for the preparation of 2-(2-((5-dimethyl-aminomethyl)furan-2-ylmethylthio)ethylamino)-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one
DE3365869D1 (en) * 1982-07-30 1986-10-09 Smith Kline French Lab Amino pyrimidinones and their preparation
GB8304593D0 (en) * 1983-02-18 1983-03-23 Beecham Group Plc Amidines
GB8311443D0 (en) * 1983-04-27 1983-06-02 Smith Kline French Lab Chemical compounds
GB8318638D0 (en) * 1983-07-09 1983-08-10 Smith Kline French Lab Chemical compounds
GB8319874D0 (en) * 1983-07-23 1983-08-24 Smith Kline French Lab Compounds
GB8320505D0 (en) * 1983-07-29 1983-09-01 Smith Kline French Lab Chemical compounds
US4772704A (en) * 1983-09-21 1988-09-20 Bristol-Myers Company 2,5-disubstituted-4(3H)-pyrimidones having histamine H2 -receptor antagonist activity
GB8328240D0 (en) * 1983-10-21 1983-11-23 Smith Kline French Lab Chemical process
GB8421427D0 (en) * 1984-08-23 1984-09-26 Smith Kline French Lab Chemical compounds
US4598067A (en) * 1984-10-16 1986-07-01 Biomeasure, Inc. Antiulcer compounds
US4785003A (en) * 1984-10-16 1988-11-15 Biomeasure, Inc. N-disubstituted glycine and B-amino-propionic acid derivatives having anti-ulcer activity
CH665838A5 (de) * 1985-06-20 1988-06-15 Lonza Ag 3-hydroxy-3-(2-methyl-5-pyridyl)-propionsaeurealkylester, ihre herstellung und verwendung.
US4912101A (en) * 1987-03-13 1990-03-27 Fujirebio Kabushiki Kaisha 4-aminomethyl-pyridyl-2-oxy derivatives having anti-ulcer activity
EA009027B1 (ru) * 2002-12-16 2007-10-26 Мицубиси Фарма Корпорейшн Производные 3-замещенного-4-пиримидона
US20230349922A1 (en) 2020-08-11 2023-11-02 Université De Strasbourg H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer

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US3980781A (en) * 1966-03-31 1976-09-14 Imperial Chemical Industries Limited Fungicidal composition and method containing 2-amino-pyrimidines
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ZA793392B (en) * 1978-07-15 1980-08-27 Smith Kline French Lab Isoureas and isothioureas
ZA793443B (en) * 1978-07-26 1980-12-31 Glaxo Group Ltd Heterocyclic derivatives
PT75074B (en) * 1981-06-27 1986-02-26 Smith Kline French Lab Process for preparing certain pyrimidone derivatives and compositions containing them

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BG34906A3 (en) 1983-12-15
IE48313B1 (en) 1984-12-12
IL56611A0 (en) 1979-05-31
MX5926E (es) 1984-08-29
AR223476A1 (es) 1981-08-31
PH17517A (en) 1984-09-13
YU29279A (en) 1983-01-21
PH18073A (en) 1985-03-18
US4234588A (en) 1980-11-18
EP0003677B1 (en) 1981-11-11
NZ189592A (en) 1982-03-09
SG61782G (en) 1984-04-19
PL118708B1 (en) 1981-10-31
FI790435A (fi) 1979-08-14
PL213374A1 (sv) 1980-02-25
NO151546B (no) 1985-01-14
US4649141A (en) 1987-03-10
MY8500590A (en) 1985-12-31
DE2961289D1 (en) 1982-01-14
DD142052A5 (de) 1980-06-04
NO790446L (no) 1979-08-14
IN151188B (sv) 1983-03-05
DK54879A (da) 1979-08-14
PT69203A (en) 1979-03-01
RO83454A (ro) 1984-02-21
IE790254L (en) 1979-08-13
JPS54115385A (en) 1979-09-07
EP0003677A3 (en) 1979-09-05
AU4399479A (en) 1979-08-23
IT1119272B (it) 1986-03-10
JPS6246547B2 (sv) 1987-10-02
AU531757B2 (en) 1983-09-08
NO151546C (no) 1985-05-02
FI66000B (fi) 1984-04-30
ATA104779A (de) 1983-01-15
HU180945B (en) 1983-05-30
HK15487A (en) 1987-02-27
IL56611A (en) 1984-10-31
ES477667A1 (es) 1979-10-16
EG13747A (en) 1982-06-30
AT372087B (de) 1983-08-25
EP0003677A2 (en) 1979-08-22
IT7967299A0 (it) 1979-02-12
SU999971A3 (ru) 1983-02-23
CA1147335A (en) 1983-05-31

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