FI66357B - REFERENCE TO A FRAMEWORK FOR PHARMACOLOGICAL PROPERTIES OF HYDROXIDERS OF AV 2-ISOPROPYLAMINOPYRIMIDE - Google Patents
REFERENCE TO A FRAMEWORK FOR PHARMACOLOGICAL PROPERTIES OF HYDROXIDERS OF AV 2-ISOPROPYLAMINOPYRIMIDE Download PDFInfo
- Publication number
- FI66357B FI66357B FI800566A FI800566A FI66357B FI 66357 B FI66357 B FI 66357B FI 800566 A FI800566 A FI 800566A FI 800566 A FI800566 A FI 800566A FI 66357 B FI66357 B FI 66357B
- Authority
- FI
- Finland
- Prior art keywords
- isopropylaminopyrimide
- hydroxiders
- framework
- hydroxy
- pharmacological properties
- Prior art date
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Classifications
-
- 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
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
-
- 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
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
---'"Ί Μ .... KUULUTUSJULKAISU--- '"Ί Μ .... ADVERTISEMENT
jggrL m (”) utlAggningsskmft 6 6 357 C (45) Γ·.' : . 1- 1^-1 ^ ^ (51) IC*Jlu/lm.a.3 C 07 O 239/46 SUOMI-FINLAND <*i) 800566 (22) H«k*ml*p*l»t AnaMcningadac 26.02.80 1 ' (M) Alkupilvt GHtigMcadag 26.02.80 (41) Taltat MkiMkal — MMt cffMtNgjggrL m (”) utlAggningsskmft 6 6 357 C (45) Γ ·. ' :. 1- 1 ^ -1 ^ ^ (51) IC * Jlu / lm.a.3 C 07 O 239/46 FINLAND-FINLAND <* i) 800566 (22) H «k * ml * p * l» t AnaMcningadac 26.02 .80 1 '(M) Front Cloud GHtigMcadag 26.02.80 (41) Chisel MkiMkal - MMt cffMtNg
Patentti· ja rekisteri hail itu· πη,Γΐ nitjim μ hMAJaHalwa pea.— -09.80Patent and Register Hail itu · πη, Γΐ nitjim μ hMAJaHalwa pea.— -09.80
Patent- och register sty reiwn ' * AmMcan irtfcfd och wcLskrMaa peMkand 29.06. 84 (32)(33)(31) Pyy4«qrewoHcn Bfird pctartft 10.03.79 30.0¾.79 Englanti-England(GB) 7908494 7914987 (71) SociStS d'Etudes de Produits Chimiques, 4, rue Thdodule Ribot, 75017 Paris, Ranska-Frankrike(FR) (72) AndrS Esanu, Paris, Ranska-Frankrike(FR) (74) Leitzinger Oy (54) Menetelmä valmistaa farmakologisesti arvokkaita 2-ίsopropyy1i-aminopyrimidiin in hydroksijohdannaisia - Förfarande för fram-ställning av farmakologiskt värdefulla hydroxiderivat av 2-iso-propy1 am i nopy r i m i d i nPatent- och register sty reiwn '* AmMcan irtfcfd och wcLskrMaa peMkand 29.06. 84 (32) (33) (31) Pyy4 «qrewoHcn Bfird pctartft 10.03.79 30.0¾.79 English-England (GB) 7908494 7914987 (71) SociStS d'Etudes de Produits Chimiques, 4, rue Thdodule Ribot, 75017 Paris, France-France (FR) (72) AndrS Esanu, Paris, France-France (FR) (74) Leitzinger Oy (54) Method for the preparation of pharmacologically valuable hydroxy derivatives of 2-isopropylaminopyrimidine - For the preparation of pharmacologically active hydroxylated compounds 2-iso-propy1 am i nopy rimidine
Menetelmä valmistaa farmakologisesti arvokkaita 2-isopropyyii-aminopyrimidiinin hydroksijohdannaisia, joiden yleiskaava I on A< \ >=N CH3The process for the preparation of pharmacologically valuable hydroxy derivatives of 2-isopropylaminopyrimidine of the general formula I is A <\> = N CH3
Ac--(. Λ— NH-CH ^ 5 ^H3 (T) Ä6 / jossa kaavassa kukin ryhmistä A4, A5 ja Ag on vetyatomi tai hydroksiryhmä, edellyttäen, että ainakin yksi ryhmistä A4, Ag ja Ag ei ole vetyatomi.Ac - (.Λ- NH-CH 2 5 ^ H 3 (T) Ä 6 / in which each of A4, A5 and Ag is a hydrogen atom or a hydroxy group, provided that at least one of A4, Ag and Ag is not a hydrogen atom.
Näissä yhdisteissä on erityisen mielenkiintoista niiden vaikutus hermojen regeneroinnissa ja niiden käyttö lihasdystrofiän hoidossa.Of particular interest are their effect on nerve regeneration and their use in the treatment of muscular dystrophy.
Keksinnön mukaiselle menetelmälle on tunnusomaista se, ettäThe method according to the invention is characterized in that
2-tiometyylipyrimidiinin hydroksijohdannainen, jolla on kaava IIA hydroxy derivative of 2-thiomethylpyrimidine of formula II
2 663572 66357
A\ NA \ N
a5—\ /)— s CK3 (II) saatetaan reagoimaan isopropyyliamiinin kanssa polaarittomassa liuottimessa 100 - 120°C:ssa paineen alla.α5 - (/) - s CK3 (II) is reacted with isopropylamine in a non-polar solvent at 100-120 ° C under pressure.
Seuraavat esimerkit selventävät keksintöä:The following examples illustrate the invention:
Esimerkki 1: 4-hydroksi 2-isopropyyliaminopyrimidiini Lähtöaineena käytetty metyylitiourasiili valmistetaan saattamalla metyylijodidi reagoimaan tiourasiilin kanssa natriummetanolaatin läsnäollessa. Metyylitiourasiilia saadaan 20 g (0,14 moolia). Metyylitiourasiili, 200 ml kuivaa tolueenia ja 200 ml isopropyyli-amiinia laitetaan 1 litran painereaktoriin. Reaktio suoritetaan 24 tunnin aikana paineenalaisena 110 - 120°C:ssa. Saatu seos haihdutetaan kuiviin, käsitellään asetonilla ja dietyylieetterillä (50/50), suodatetaan, pestään vedellä ja kiteytetään uudelleen isopropyyliasetaatista. Näin saadaan 17 g (saanto 84 %) valkoista kiteistä tuotetta, sp. 140°C. Analyysin perusteella tuote vastaa hyvin kaavaa c7HnN3°· Tästä yhdisteestä valmistetaan myös hydro-kloridi (sp. 233 - 234°C (Tottoli), joka myös on valkoinen kiteinen aine; sen UV-spektri on:Example 1: 4-Hydroxy 2-isopropylaminopyrimidine The starting methylthiouracil is prepared by reacting methyl iodide with thiouracil in the presence of sodium methanolate. 20 g (0.14 mol) of methylthiouracil are obtained. Methylthiouracil, 200 ml of dry toluene and 200 ml of isopropylamine are placed in a 1 liter pressure reactor. The reaction is carried out under pressure at 110 to 120 ° C for 24 hours. The resulting mixture is evaporated to dryness, treated with acetone and diethyl ether (50/50), filtered, washed with water and recrystallized from isopropyl acetate. 17 g (84% yield) of a white crystalline product are thus obtained, m.p. 140 ° C. Based on the analysis, the product corresponds well to the formula c7HnN3 ° · This compound is also used to prepare the hydrochloride (m.p. 233-234 ° C (Tottoli)), which is also a white crystalline substance with a UV spectrum of:
Vedessä (hydrokloridille) Metanolissa (emäkselle) X__v : 266 nm 1% Xmax : 293 nm max E s 210 max E - 510 lcm lcmIn water (for hydrochloride) In methanol (for base) X__v: 266 nm 1% Xmax: 293 nm max E s 210 max E - 510 lcm lcm
Xm3V : 217 nm 1% Xmax : 222 nm 1% max E _ 740 max E _ 730 lcm lcmXm3V: 217 nm 1% Xmax: 222 nm 1% max E _ 740 max E _ 730 lcm lcm
Xmax : 290 nm 3 66357Λmax: 290 nm 3 66357
Emäs on valkoinen kiteinen tuote (molekyylipaino 153,18), joka ei liukene veteen mutta liukenee kloroformiin.The base is a white crystalline product (molecular weight 153.18) that is insoluble in water but soluble in chloroform.
Esimerkki 2: 5-hydroksi 2-isopropyyliaminopyrimidiiniExample 2: 5-Hydroxy 2-isopropylaminopyrimidine
Esimerkin 1 menetelmä toistettiin mutta käytettiin 5-hydroksi 2-tiometyylipyrimidiiniä. Saanto 83 %. Reaktiolämpötila oli 105°C. Sulamispiste 161°C (Tottoli). UV-spektri, vesi 60/metanoli 40: \nax : 341 nm = 205 lcm \nax : 241 nm E^% = 1210 lcmThe procedure of Example 1 was repeated but 5-hydroxy-2-thiomethylpyrimidine was used. Yield 83%. The reaction temperature was 105 ° C. Melting point 161 ° C (Tottoli). UV spectrum, water 60 / methanol 40: Nax: 341 nm = 205 lcm \ nax: 241 nm Emax = 1210 lcm
Esimerkki 3: 4,6-dihydroksi 2-isopropyyliaminopyrimidiiniExample 3: 4,6-Dihydroxy 2-isopropylaminopyrimidine
Esimerkin 1 menetelmä toistettiin mutta käytettiin 4,6-dihydro | O ΐ1 2-tiometyylipyrimidiiniä. Saanto 67 %. Reaktiolämpötila 110 C. jThe procedure of Example 1 was repeated but 4,6-dihydro was used O ΐ1 2-thiomethylpyrimidine. Yield 67%. Reaction temperature 110 C. j
Kaavan ,HC1 mukaisen hydrokloridin sulamispiste 215 - 220°C, hajoaa (Tottoli). Tämä on valkoinen kiteinen tuote, joka ei liukene veteen huoneen lämpötilassa. 1The hydrochloride of formula HCl has a melting point of 215-220 ° C, decomposes (Tottoli). This is a white crystalline product which is insoluble in water at room temperature. 1
Toksisuustoxicity
Keksinnön mukaisten yhdisteiden akuutti toksisuus (mg/kg) määritettiin hiirillä i.p. ja per os. Tulokset on esitetty seuraavassa taulukossa: ^'^^^Yhdiste ~ ^_ Esim. 1 Esim. 2 Esim. 3The acute toxicity (mg / kg) of the compounds of the invention was determined in mice i.p. and per os. The results are shown in the following table: ^ '^^^ Compound ~ ^ _ Example 1 Example 2 Example 3
Tie _ —______ i.p. 240 200 260 j per os 355 205 285Tie _ —______ i.p. 240 200 260 j per os 355 205 285
FarmakologiaPharmacology
Keksinnön mukaisen yhdisteen farmakologista aktiivisuutta on tutkittu seuraavalla vertailukokeella, jossa tutkittiin täysi kasvuisen urosrotan (Wistar) lonkkahermon regeneroitumista.The pharmacological activity of the compound of the invention has been studied in the following comparative experiment in which complete regeneration of the sciatic nerve of a growing male rat (Wistar) was examined.
6635766357
Rottien lonkkahermoa vioitetaan kohdistamalla hermoon 20 minuuttia lämpöääntä -20°C:ssa. Sen jälkeen rottia hoidetaan tietyn ajan i.p. vertailutuotteella tai keksinnön mukaisilla yhdisteillä. Hoidon lopussa rotat tapetaan, lonkkahermot erotetaan ja niihin yhdistetään 70 ohutta yhdensuuntaista platinalankaa (väli 1 mm). Vioitetun kohdan yläpuolelta johdettua sähkösignaalia seurataan platinalan-kojen avulla: Etäisin lanka, jonka kohdalla signaali voidaan havaita, ilmoittaa regeneroituneen pituuden.The sciatic nerve of rats is damaged by applying heat to the nerve for 20 minutes at -20 ° C. The rats are then treated i.p. for a period of time. reference product or compounds of the invention. At the end of the treatment, the rats are sacrificed, the sciatic nerves are separated and combined with 70 thin parallel platinum wires (1 mm apart). The electrical signal conducted above the damaged point is monitored by platinum wires: The farthest wire at which the signal can be detected indicates the regenerated length.
Kutakin testattua yhdistettä ja kutakin hoitoaikaa kohti käytetään 8 rotan ryhmää.For each compound tested and each treatment time, 8 groups of rats are used.
Neljä yhdistettä on testattu i.p.: Esimerkin 1 yhdiste, esimerkin 2 yhdiste, esimerkin 3 yhdiste, kaikki i.p. annoksella 10 mg/kg, ja vertailuaineena vitamiinien Bl (500 mg/kg), B6 (500 mg/kg) ja B12 (5 mg/kg) seos, jonka ammattimiehet tietävät olevan tällä alalla tehokkaimman seoksen. Vertailueläimiä ei hoidettu lainkaan. Kutakin aikaa kohti (7, 11, 14, 17 ja 21 päivää) käytettiin viittä kahdeksan eläimen ryhmää sekä vertailussa, yhdisteillä 1, 2, 3 että vertai-luseoksella.Four compounds have been tested i.p .: Example 1 compound, Example 2 compound, Example 3 compound, all i.p. at a dose of 10 mg / kg, and as a reference a mixture of vitamins B1 (500 mg / kg), B6 (500 mg / kg) and B12 (5 mg / kg), which is known to those skilled in the art to be the most effective mixture in this field. Control animals were not treated at all. For each time point (7, 11, 14, 17, and 21 days), five groups of eight animals were used for both comparison, compounds 1, 2, 3, and control mixture.
Tämän kokeen tulokset on koottu seuraavaan taulukkoon yhdessä ver-tailueläimillä saatujen tulosten kanssa. Regeneroitujen hermojen pituudet on esitetty mm:ssä vastaavissa aikaa koskevissa pystyriveissä kunkin ryhmän kaikilla eläimillä mitattujen pituuksien keskiarvona. Kun mitään lukua ei ole esitetty (17 ja 21 päivää), regeneroitunut pituus on suurempi kuin otetun näytteen pituus.The results of this experiment are summarized in the following table together with the results obtained with the control animals. The lengths of the regenerated nerves are presented in mm in the corresponding time vertical rows as the average of the lengths measured in all animals in each group. When no figure is shown (17 and 21 days), the regenerated length is greater than the length of the sample taken.
5 66357 --------^Kestoaika (päiviä) 7 11 14 215 66357 -------- ^ Duration (days) 7 11 14 21
Yhdiste ja annos iTp^Compound and dose iTp ^
Vertailut 5,1 10,2 12,8 17,8 22,4Comparisons 5.1 10.2 12.8 17.8 22.4
Esimerkki 1 a Q . . . .Example 1 a Q. . . .
10 mg/kg 6-8 14'4 26,110 mg / kg 6-8 14'4 26.1
Esimerkki 2 , c _ 10 mg/kg 6'6 14'χ 26'3Example 2, c _ 10 mg / kg 6'6 14'χ 26'3
Esimerkki 3 , . c , _ 10 mg/kg 6'7 15'6 26'7Example 3,. c, _ 10 mg / kg 6'7 15'6 26'7
Bl, B6, B12 500 mg/kg, 500 mg/kg ja 5 mg/kg 8,8 13,4 15,8 20,4 23,7B1, B6, B12 500 mg / kg, 500 mg / kg and 5 mg / kg 8.8 13.4 15.8 20.4 23.7
Antamismuoto - annostus Nämä johdokset voidaan antaa missä tahansa terapeu-tisesti hyväksyttävässä muodossa, esimerkiksi tabletteina tai gelatiinikapseleina, jotka sisältävät 5 mg per annosyksikkö, yhdessä apuaineen kanssa.Form of Administration - Dosage These derivatives may be administered in any therapeutically acceptable form, for example, as tablets or gelatin capsules containing 5 mg per dosage unit, together with an excipient.
Injisoitavassa muodossa tuote voi olla annosteltu pullosiin, jotka sisältävät 1 mg aktiivista ainesosaa veteen liuotettuna hydroklo-ridina. Mitä tulee taas annosteluun ihmisille, niin oraalisessa antamistavassa tarvitaan 20 mg - 1 g per diem, kun taas injisoitava muoto voidaan antaa annoksina välillä 1 mg - 50 mg per diem.In injectable form, the product may be presented in vials containing 1 mg of active ingredient dissolved in water as hydrochloride. Again, for administration to humans, the oral route of administration requires 20 mg to 1 g per diem, while the injectable form may be administered in doses ranging from 1 mg to 50 mg per diem.
Seuraavassa on annettu esimerkki tablettimuodosta: - Jonkin esimerkin mukainen yhdiste 5 mg - Laktoosi 70 mg - Talkki 20 mg - Magnesiumstearaatti 5 mg 100 mgThe following is an example of a tablet form: - Compound according to one example 5 mg - Lactose 70 mg - Talc 20 mg - Magnesium stearate 5 mg 100 mg
Claims (1)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB7908494 | 1979-03-10 | ||
GB7908494 | 1979-03-10 | ||
GB7914987 | 1979-04-30 | ||
GB7914987 | 1979-04-30 |
Publications (3)
Publication Number | Publication Date |
---|---|
FI800566A FI800566A (en) | 1980-09-11 |
FI66357B true FI66357B (en) | 1984-06-29 |
FI66357C FI66357C (en) | 1984-10-10 |
Family
ID=26270867
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI800566A FI66357C (en) | 1979-03-10 | 1980-02-26 | REFERENCE TO A FRAMEWORK FOR PHARMACOLOGICAL PROPERTIES OF HYDROXIDERS OF AV 2-ISOPROPYLAMINOPYRIMIDE |
Country Status (24)
Country | Link |
---|---|
JP (1) | JPS55122768A (en) |
AR (1) | AR222691A1 (en) |
AU (1) | AU533547B2 (en) |
BE (1) | BE881752A (en) |
CA (1) | CA1132561A (en) |
CH (1) | CH644368A5 (en) |
DE (3) | DE3009071C2 (en) |
EG (1) | EG14282A (en) |
FI (1) | FI66357C (en) |
FR (2) | FR2451370A1 (en) |
GB (1) | GB2045756B (en) |
HK (1) | HK55383A (en) |
IE (1) | IE49547B1 (en) |
IN (1) | IN153791B (en) |
LU (1) | LU82185A1 (en) |
MX (1) | MX6218E (en) |
MY (1) | MY8400200A (en) |
NL (1) | NL184833C (en) |
NO (1) | NO154054C (en) |
NZ (1) | NZ192927A (en) |
OA (1) | OA06484A (en) |
PT (1) | PT70882A (en) |
SE (1) | SE435180B (en) |
SG (1) | SG22683G (en) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE894517A (en) * | 1981-10-16 | 1983-01-17 | Sod Conseils Rech Applic | NEW ISOPROPYLAMINO PYRIMIDINE DERIVATIVE, ITS PREPARATION AND THERAPEUTIC COMPOSITION BASED ON ITS COMPOUNDS |
US4673677A (en) * | 1983-10-03 | 1987-06-16 | Pfizer Inc. | Method for treatment of gastrointestinal disorders |
US4554276A (en) * | 1983-10-03 | 1985-11-19 | Pfizer Inc. | 2-Amino-5-hydroxy-4-methylpyrimidine derivatives |
US4711888A (en) | 1985-07-24 | 1987-12-08 | Pfizer Inc. | Hydroxy and alkoxy pyrimidines |
WO1989000423A1 (en) * | 1987-07-09 | 1989-01-26 | Pfizer Inc. | 2-amino-5-hydroxy-4-pyrimidones |
US4910204A (en) * | 1988-06-28 | 1990-03-20 | Pfizer Inc. | 2-amino-5-hydroxy-4-pyrimidones |
HU206337B (en) * | 1988-12-29 | 1992-10-28 | Mitsui Petrochemical Ind | Process for producing pyrimidine derivatives and pharmaceutical compositions |
US5264435A (en) * | 1988-12-29 | 1993-11-23 | Mitsui Petrochemical Industries, Ltd. | Pyrimidines and their pharmaceutical acceptable salts, and their use as medicines |
US4940712A (en) * | 1989-05-26 | 1990-07-10 | Pfizer Inc. | Derivatives of hydroxyprimidines as leukotriene synthesis inhibitors |
US5270319A (en) * | 1991-09-09 | 1993-12-14 | Warner-Lambert Company | 5-hydroxy-2-pyrimidinylmethylene derivatives useful as antiinflammatory agents |
US5220025A (en) * | 1992-02-24 | 1993-06-15 | Warner-Lambert Company | 2-substituted amino-4, 6-di-tertiary-butyl-5-hydroxy-1, 3-pyrimidines as antiinflammatory agents |
US5196431A (en) * | 1992-02-24 | 1993-03-23 | Warner-Lambert Company | 2-substituted amino-4, 6-di-tertiary-buthyl-5-hydroxy-1, 3-pyrimidines as antiinflammatory agents |
US9133212B1 (en) * | 2005-06-15 | 2015-09-15 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB741667A (en) * | 1952-12-05 | 1955-12-07 | Ici Ltd | New pyrimidine derivatives |
GB756189A (en) * | 1954-02-01 | 1956-08-29 | Ici Ltd | New pyrimidine derivatives |
ZA711152B (en) * | 1970-03-02 | 1971-11-24 | Ici Ltd | Manufacture of pyrimidines |
GB1525995A (en) * | 1976-02-18 | 1978-09-27 | Soc D Etudes Prod Chimique | Aminopyrimidine salt |
-
1980
- 1980-02-12 IN IN103/DEL/80A patent/IN153791B/en unknown
- 1980-02-15 BE BE0/199421A patent/BE881752A/en not_active IP Right Cessation
- 1980-02-20 NZ NZ192927A patent/NZ192927A/en unknown
- 1980-02-20 LU LU82185A patent/LU82185A1/en unknown
- 1980-02-26 FI FI800566A patent/FI66357C/en not_active IP Right Cessation
- 1980-02-27 AR AR280106A patent/AR222691A1/en active
- 1980-02-29 PT PT70882A patent/PT70882A/en unknown
- 1980-03-03 CH CH165080A patent/CH644368A5/en not_active IP Right Cessation
- 1980-03-04 CA CA346,981A patent/CA1132561A/en not_active Expired
- 1980-03-04 NL NLAANVRAGE8001289,A patent/NL184833C/en not_active IP Right Cessation
- 1980-03-07 IE IE477/80A patent/IE49547B1/en unknown
- 1980-03-07 GB GB8007908A patent/GB2045756B/en not_active Expired
- 1980-03-07 AU AU56248/80A patent/AU533547B2/en not_active Ceased
- 1980-03-07 SE SE8001812A patent/SE435180B/en not_active IP Right Cessation
- 1980-03-07 NO NO800664A patent/NO154054C/en unknown
- 1980-03-09 EG EG131/80A patent/EG14282A/en active
- 1980-03-10 JP JP2931280A patent/JPS55122768A/en active Granted
- 1980-03-10 MX MX808702U patent/MX6218E/en unknown
- 1980-03-10 OA OA57049A patent/OA06484A/en unknown
- 1980-03-10 DE DE3009071A patent/DE3009071C2/en not_active Expired
- 1980-03-10 DE DE3050999A patent/DE3050999C2/en not_active Expired
- 1980-03-10 FR FR8005278A patent/FR2451370A1/en active Granted
- 1980-03-10 FR FR8005277A patent/FR2451191A1/en active Granted
- 1980-04-30 DE DE19803016752 patent/DE3016752A1/en active Granted
-
1983
- 1983-04-28 SG SG226/83A patent/SG22683G/en unknown
- 1983-11-17 HK HK553/83A patent/HK55383A/en unknown
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1984
- 1984-12-30 MY MY200/84A patent/MY8400200A/en unknown
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