IL29496A - Fungicidal compositions containing salts of pyrimidine derivatives and certain novel salts of pyrimidine derivative - Google Patents

Fungicidal compositions containing salts of pyrimidine derivatives and certain novel salts of pyrimidine derivative

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Publication number
IL29496A
IL29496A IL2949668A IL2949668A IL29496A IL 29496 A IL29496 A IL 29496A IL 2949668 A IL2949668 A IL 2949668A IL 2949668 A IL2949668 A IL 2949668A IL 29496 A IL29496 A IL 29496A
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IL
Israel
Prior art keywords
alkyl
hydrogen
salt
alkenyl
optionally substituted
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IL2949668A
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Ici Ltd
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Publication of IL29496A publication Critical patent/IL29496A/en

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    • 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
    • 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
    • C07D239/48—Two 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen 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
    • C07D239/46—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
    • 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
    • C07D239/69—Benzenesulfonamido-pyrimidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

1,223,686. Fungicidal seed dressings. IMPERIAL CHEMICAL INDUSTRIES Ltd. 12 Feb., 1968 [24 Feb., 1967; 30 June, 1967], Nos. 30348/67 and 30354/67. Heading A2Q. [Also in Divisions A5 and C2] A seed dressing having fungicidal properties comprises as active ingredient an acid addition salt or metal salt of a pyrimidine of the formula or an acid addition salt of an ether thereof, where X is oxygen or sulphur, R 1 and R 2 are hydrogen, optionally substituted hydrocarbon, heterocystic, benzylidine-imino, amino or sulphur-free substituted amino, cyano, optionally substituted carbamoyl or R.CO- or R.CO 2 groups (where R is optionally substituted hydrocarbon), or R 1 and R 2 together with the N atom complete an optionally substituted helerocyclic ring which may contain further hetero atoms, and R 3 and R 4 are hydrogen, halogen, an optionally substituted hydrocarbon group bound to the pyrimidine ring through -O- or -S-, heterocyclic-substituted alkyl, nitro, ajophenyl or alkylsulphonyl groups or R 3 and R 4 together form an optionally substituted alkylene or alkenylene bridging group, together with a solid diluent or liquid diluent containing a surface active agent. The dressing may be applied to.e.g., wheat barley or rice. Evample 42 describes a composition based on china clay containing the potassium salt of 2-dimethylamino- 4-methyl-5-n-butyl-6-hydroxypyrimidine. [GB1223686A]

Claims (30)

29496/2 WHAT VIE CLAIM IS:
1. A fungicidal composition comprising as an active ingredient an acid addition salt or a metal salt of a pyrimidine derivative of the formula: wherein R, and R_ are: hydrogen alkyl, morpholinoalkyl , cycloalkyl, alkenyl, aryl, haloaryl, alkaryl aryl alkoxycarbonyl/, aralkyl pyridyl , tetrazolyl a benzylidene-imino group amino, optionally substituted by phenyl; a cyano group a carbamoyl group an R.CO- or R.SO,,- group wherein R is alkyl, haloalkyl, nitrophenyl or Rj and R2 together with the adjacent N-atom, form a guanidine, halophenyl guanidino or a saturated heterocyclic ring which may contain a further oxygen or nitrogen atom, the latter being optionally substituted by lower alkyl; and wherein R, and R. are: 3 4 hydrogen halogen alkyl, optionally substituted by phenyl, alkylphenyl, piperidino, halophenyl, morpholino, alkoxy, halohydroxy, alkylthio alkenyl nitro phenyl, optionally substituted by alkyl, alkoxy, halogen alkylsulphonyl phenylthio, optionally substituted by halogen, alkyl aralkylthio V 29496/3 phenylazo formyl or Rg and R^ together form a trimethylene bridge, or benzene ring, or 4-hydroxy-2-dimethylamino-quinazoline ring and wherein R,. is: hydrogen alkyl, substituted by hydroxy, dialkylamino alkanoyl, phenyl, alkylthio or alkoxycarbonyl alkenyl 2-dimethylamino-5-butyl-4-pyrimid^rlthio and wherein X is an atom of oxygen or sulphur; and a carrier for the active ingredient comprising a solid diluent, or a liquid diluent containing a surface active agent.
2. A fungicidal composition comprising as an active ingredient an acid addition salt or a metal salt of a pyrimidine derivative of the formula wherein R^ is hydrogen, alkyl, or aralkyl; R2 *s nydrogen, alkyl alkenyl, unsubstituted aryl or halo-, alkyl-, or alkoxycarbonyl- substituted aryl, unsubstituted or phenyl ' substituted amino, cyanb, alkylcarbonyl, haloalkylcarbonyl, pyridyl, tetrazolyl, morpholino- substituted alkyl, carbamoyl, or R^ and R7 together with the adjacent N-atom form saturated heterocyclic ' ring which may contain one additional heterocyclic atom selectedfrom oxygen and nitrogen; R^ and R^ are hydrogen, halogen, alkyl, alkaryl, alkenyl, alkylthioalkyl, alkoxyalkyl, hydroxyhaloalkyl, nitro, morpholino- or piperidino- substituted alkyl phenyl or aryloxy, or phenylthio or alkylsulphonyl; and wherein j. is hydrogen, alkyl, substituted by hydroxy, dialkylamino, alkanoyl, phenyl; alkylthio or alkoxycarbonyl, alkenyl, 2-dimethylamino-5-butyl- 4-pyrimidylthio andX is an atom of oxygen or sulphur; and a carrier for the active ingredient comprising a solid diluent, er a liquid diluent containing a surface active agent. 294Θ6
3. A fungicidal composition comprising as an active ingredient an acid addition salt or a metal salt of a pyrxmidine derivative of the formula: wherein R^ and are hydrogen or lower alkyl groups, or R^ and together with the adjacent nitrogen atom form a saturated heterocyclic ring; R^ is a lower alkyl grotip, ^'is a lower alkyl or alkenyl group; Rj. is hydrogen, alkyl, substituted by hydroxy, dialkylamino, alkanoyl, phenyl, alkylthio, alkoxycarbonyl, alkenyl, 2-dimethylamino-5-butyl-4~ pyrimidylthio; andX is an atom of oxygen or sulphur; and a carrier for the active ingredient comprising a solid diluent, or .a liquid diluent containing a surface active agent.
4. A fungicidal composition according to claim 3 wherein the active ingredient is an acid additional salt or a metal salt of a compound in which ^ R2 and R_, are methyl or ethyl groups; R4 is an alkyl or alkenyl group containing from one to five carbon atoms; and Xis an atom of oxygen or sulphur*
5. A fungicidal composition according to any of claims 1 to 4 wherein the active ingredient is a salt of a pyrimidine derivative as defined and in which the Group XR^ is etherified having an ether group comprising an hydroxyalkyl, phenylalkyl alkenyl, alkoxycarbonylalkyl, alkylcarbonylalkyl, dialkylaminoalkyl , or alkylthioalkyl residue.
6. » . Acid additiona salts and metal salts of a pyrimidine derivative of the formula: wherein R^ and 2 are hydroge alkyl, morpholinoalkyl, cycloalkyl, 29496/3 alkenyl, aryl, haloaryl, alkaryl alkoxycarbonylaryl , aralkyl pyridyl, tetrazolyl a benzylidene-iiaino group, amino, optionally substituted by phenyl; a cyano group a carbamoyl group an R.CO- or R.SC^- group wherein R is alkyl, haloalkyl, nitrophenyl or ^ and together with the adjacent N-atom, form a guanidino, halophenyl, guanidino or a saturated heterocyclic ring which may contain a further oxygen or nitrogen atom, the latter being optionally substituted by loweralkyl; and wherein R and R. are: 3 hydrogen halogen alkyl, optionally substituted by phenyl, alkylphenyl, halophenyl, morpholino, alkoxy, halohydroxy alkylthio alkenyl nitro phenyl, optionally substituted by alkyl, alkoxy, halogen alkylsulphonyl phenylthio, optionally substituted by halogen, alkyl aralkylthio aryioxy phenylazo formyl or and R^ together form a trimethylene bridge, or benzene ring, or 4-hydroxy-2dimethylamino-quinazoline ring; and wherein R5 is: hydrogen-alkyl, substituted by hydroxy, dialkylamino alkanoyl, phenyl, alkylthio, alkoxycarbonyl alkenyl 2-dimethylamino-5-butyl-4-pyrimidylthio and wherein X is an atom of oxygen or sulphur; provided that R^ is not hydrogen when R% is hydrogen, or when R. and R» are alkyl and R9 is hydrogen 29496/3 or alkyl, and that R^ and 2 are not both hydrogen when R3 and ^ are both alkyl groups.
7. Acid addition salts and metal salts of a pyrimidine derivative of the formula: wherein ^ is hydrogen, alkyl, or aralkyl; 2 is hydrogen, alkyl, alkenyl, unsubstituted aryl or halo-, alkyl-, or alkoxycarbonyl- substituted aryl, unsubstituted or phenyl substituted amino, cyano, alkylcarbonyl, halo-alkylcarbonyl , pyridyl, tetrazolyl, morpholino- substituted alkyl, carbamoyl, or and R2 together with the adjacent N-atom form a saturated heterocyclic ring which may contain one additional heterocyclic atom selected from oxygen and nitrogn; ^ and R4 are, hydrogen, alkyl, alkylphenyl, alkenyl, alkylthioalkyl, alkoxyalkyl, hydroxyhaloalkyl, nitro* morpholino-or piperidino- substituted alkyl, aryl or aryloxy or phenylthio, or alkylsulphonyl; R^ is hydrogen* alkyl, substituted hydroxy, dialkylamino, alkanoyl, phenyl, alkylthio, alkoxycarbonyl, alkenyl, 2-dimethylamino-5-butyl-4-pyrimidyl hio; X is an atom of oxygen or sulphur; provided that R^ is not hydrogen when R^ is hydrogen* o when and are alkyl and g is hydrogen or alkyl and that and R2 are not both hydroge Hhen Rj are both alkyl groups.
8. Acid additional salts, and metal salts of a pyrimidine derivative as claimed in claim 6, of the formula: NR1R2 wherein R^ and R2 are hydrogenor lower alkyl groups, or R^ and R2 together with the adjacent nitrogen atom form a saturated heterocyclic ring; R^ is a lower alkyl group; R^ is a lower alkyl or alkenyl group; X is an atom of oxygen or sulphur; provided that R^ is not hydrogen when R R and R^ are all alkyl groups and that Rj^ and R^, are not both hydrogen when Rg and R^ are both alkyl groups. 29496/2
9. A salt of a pyrimidine derivative claimed in claim 8, wherein the active ingredient is a compound in which R^, and R^ are methyl or ethyl groups; R^ is an alkyl or alkenyl group containing from teo to five carbon atoms; and X is an atom of oxygen or sulphur.
10. A salt of a pyrimidine derivative as claimed in any of claims 6 to 9 and in which the group -XR^ is etherified having an ether b phenylalkyl group comprising an alkyl , hydroxyalkyl , aralkyl, alkenyl, alkoxycarbonyl-alkyl, alkylcarbonylalkyl^jj lkylaminoalkyl, or alkylthioalkyl residue.
11. An acid addition or metal salt of 2-dimethylamino-4-methyl-5-n-butyl-6-hydroxy-pyrimidine.
12. An acid addition or metal salt of 2-ethylamino-4-methyl-5-n-butyl-6-hydrox -pyrimidine.
13. Salts of the compounds numbered 2, 3, 9, 12, 28,37, 61, 69, 74, 90, 115, 116 and 125 in Tables I to III hereinbefore set forth.
14. A salt as claimed in any of claims 6 to 13 which is a hydrohalide or alkali metal salt.
15. A salt as claimed in any of claims 6 to 13 which is a hydrochloride.
16. A fungicidal composition comprising as an active ingredient a salt as claimed in any of claims 6 to 15, and a carrier.
17. A fungicidal composition comprising an aqueous solution of any of the salts claimed in any of claims 6 to 15.
18. A fungicidal composition as claimed in claim 16 wherein a carrier is present which is a solid or liquid.
19. A fungicidal composition as claimed in claim 16 wherein the carrier is water.
20. A fungicidal composition as claimed in any of claims 16 to 19 and comprising a wetting agent and/or a corrosion inhibitor.
21. A fungicidal composition as claimed in any of claims 1 to 5 or 16 to 19 containing from 0.001% to 85% by weight of the active ingredient.
22./ A fungicidal composition as claimed in clalfti 21 containing 29496/2
23. A fungicidal composition as claimed in claim 21 containing from 0.001 to 10% by weight of the active ingredient.
24. A process for the preparation of salts of pyrimidine derivatives of Tables I to III substantially as described in any of Examples 1 to 33.
25. A salt of a pyrimidine derivative substantially as described in any of Examples 1 to 33.
26. A fungicidal composition containing as active ingredient a salt claimed in claim 25, together with a diluent carrier.
27. A fungicidal composition substantially as described, particularly with reference to Examples 34 to 43.
28. A method for the combating of undesired iui&¾" infestations in growing plants which comprises applying to the locus of the plant a salt of a pyrimidine derivative as claimed in any of claims 6 to 15, or a fungicidal composition as claimed in any of claims 1 to.5 or 16 to 19.
29. A method of combating plant pathogens,in which a plant susceptible to such pathogens, or seed thereof, is treated with a salt of a pyrmidine derivative as defined in any of claims 6 to 15 or a fungicidal composition as claimed in any of claims 1 to 5 or 16 to 19.
30. A fertiliser comprising a salt of a pyrimidine derivative as claimed in any of claims 6 to 15 or a fungicidal composition as claimed in any of claims 1 to 5 or 16 to 19. S.HOROWITZ § CO. AGENTS FOR APPLICANTS
IL2949668A 1967-02-24 1968-02-19 Fungicidal compositions containing salts of pyrimidine derivatives and certain novel salts of pyrimidine derivative IL29496A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB3034867A GB1223686A (en) 1967-02-24 1967-02-24 Salts of pyrimidine derivatives and the use thereof as fungicides
GB3035467 1967-06-30

Publications (1)

Publication Number Publication Date
IL29496A true IL29496A (en) 1976-01-30

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CY (1) CY682A (en)
GB (1) GB1223686A (en)
IE (1) IE31957B1 (en)
IL (1) IL29496A (en)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1466177A (en) 1973-03-23 1977-03-02 Sandoz Ltd 4-hydroxy-pyrimidine derivatives
US4399142A (en) 1973-05-03 1983-08-16 Smith Kline & French Laboratories Limited Pharmacologically active compounds
US4600720A (en) * 1973-05-03 1986-07-15 Smith Kline & French Laboratories Ltd. Pharmacologically active compounds
US4537779A (en) * 1973-05-03 1985-08-27 Smith Kline & French Laboratories Limited Pharmacologically active compounds
US4341787A (en) 1973-05-03 1982-07-27 Smith Kline & French Laboratories Limited Pharmacologically active compounds
US4470985A (en) * 1973-05-03 1984-09-11 Smithkline & French Laboratories Limited Pharmacologically active compounds
US3932617A (en) * 1974-05-24 1976-01-13 The Upjohn Company Interferon induction
IN151188B (en) * 1978-02-13 1983-03-05 Smith Kline French Lab
ZA792608B (en) * 1978-05-30 1980-06-25 Smith Kline French Lab Nitro compounds
ZA793392B (en) 1978-07-15 1980-08-27 Smith Kline French Lab Isoureas and isothioureas
US4496567A (en) * 1978-11-13 1985-01-29 Smith Kline & French Laboratories Limited Phenyl alkylaminopyrimidones
US4521418A (en) * 1979-02-21 1985-06-04 Smith Kline & French Laboratories Limited Guanidinothiazolyl derivatives
US5434157A (en) * 1979-03-19 1995-07-18 The Upjohn Company 6-aryl pyrimidine compounds and method for treating viral infections and inducing interferon production
US5002951A (en) * 1979-03-19 1991-03-26 The Upjohn Company Method for treating bacterial and protozoal infections
US4507302A (en) * 1979-03-19 1985-03-26 The Upjohn Company Method for treating arthritis with 6-aryl pyrimidine compounds
US4255428A (en) 1979-03-24 1981-03-10 Smith Kline & French Laboratories Limited 5-(Hydroxypyridylalkyl)-4-pyrimidones
JPS55151570A (en) * 1979-05-15 1980-11-26 Takeda Chem Ind Ltd Pyrimidine derivatives, their preparation and antimicrobial for agriculture
US5554617A (en) * 1979-09-28 1996-09-10 The Upjohn Company Method for treating cancer with 6-aryl pyrimidine compounds
US4460589A (en) * 1980-10-03 1984-07-17 The Upjohn Company Process for treating hypertension
US4308272A (en) 1980-10-03 1981-12-29 The Upjohn Company Process for treating hypertension
US4400201A (en) * 1980-12-15 1983-08-23 Sandoz Ltd. Novel pyrimidinyl ethers, their use as herbicides, herbicidal compositions comprising said pyrimidinyl ethers and processes for the preparation thereof
US4525477A (en) * 1981-12-02 1985-06-25 Smith Kline & French Laboratories Limited 2-Thiazolyl, isothiazolyl, oxazolyl and isoxazolyl alkylamino-3-nitro-heterocyclic compounds
US4593096A (en) * 1982-06-09 1986-06-03 The Upjohn Company Novel compounds and process for treating hypertension
US6495558B1 (en) 1999-01-22 2002-12-17 Amgen Inc. Kinase inhibitors

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Publication number Publication date
CY682A (en) 1973-05-03
GB1223686A (en) 1971-03-03
IE31957L (en) 1968-08-24
IE31957B1 (en) 1973-02-21

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