CA1232904A - Pyrimidones substituees ayant des proprietes antifongiques - Google Patents

Pyrimidones substituees ayant des proprietes antifongiques

Info

Publication number: CA1232904A
Authority: CA; Canada
Prior art keywords: compound; formula; pyrimidine; pyrido; carboxylic acid
Prior art date: 1984-03-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000450491A

Other languages

English (en)

Inventor

Adi M. Treasurywala

Jehan Bagli

Harold Baker

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Canada Inc

Original Assignee

Ayerst Mckenna and Harrison Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-03-26

Filing date

1984-03-26

Publication date

1988-02-16

1984-03-26 Application filed by Ayerst Mckenna and Harrison Inc filed Critical Ayerst Mckenna and Harrison Inc

1984-03-26 Priority to CA000450491A priority Critical patent/CA1232904A/fr

1988-02-16 Application granted granted Critical

1988-02-16 Publication of CA1232904A publication Critical patent/CA1232904A/fr

Status Expired legal-status Critical Current

Links

150000008318 pyrimidones Chemical class 0.000 title abstract description 3
230000000843 anti-fungal effect Effects 0.000 title description 7
238000000034 method Methods 0.000 claims abstract description 17
150000001875 compounds Chemical class 0.000 claims description 100
125000004494 ethyl ester group Chemical group 0.000 claims description 42
150000003839 salts Chemical class 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 14
-1 3-(acetyloxy)-4-oxo-4H-pyrido[1,2-a] thieno[2,3-d] pyrimidine-2-carboxylic acid Chemical compound 0.000 claims description 14
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 13
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 11
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
DJYCOYZZTRFION-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-n-(1,3-thiazol-2-yl)methanimine Chemical compound CSC(SC)=NC1=NC=CS1 DJYCOYZZTRFION-UHFFFAOYSA-N 0.000 claims description 8
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
239000012312 sodium hydride Substances 0.000 claims description 7
229910000104 sodium hydride Inorganic materials 0.000 claims description 7
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 6
UAYKGOMDUQLCJS-UHFFFAOYSA-N ethylsulfanyl acetate Chemical compound CCSOC(C)=O UAYKGOMDUQLCJS-UHFFFAOYSA-N 0.000 claims description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
230000000397 acetylating effect Effects 0.000 claims description 4
PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 claims description 4
230000002140 halogenating effect Effects 0.000 claims description 3
BAUDWVIJAFXHAF-UHFFFAOYSA-N n,n-diethylethanamine;1,3-thiazol-2-ylcarbamodithioic acid Chemical compound CCN(CC)CC.SC(=S)NC1=NC=CS1 BAUDWVIJAFXHAF-UHFFFAOYSA-N 0.000 claims description 3
230000000875 corresponding effect Effects 0.000 claims 11
ONCWUCMTVAUEGR-UHFFFAOYSA-N 4-hydroxy-2-oxo-6-thia-1,8-diazatricyclo[7.4.0.03,7]trideca-3(7),4,8,10,12-pentaene-5-carboxylic acid Chemical compound OC1=C(SC=2N=C3N(C(C21)=O)C=CC=C3)C(=O)O ONCWUCMTVAUEGR-UHFFFAOYSA-N 0.000 claims 8
ZXTDUVJZVFRIDU-UHFFFAOYSA-N 2-methylsulfanyl-4-oxopyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=CC=CN2C(=O)C(C(O)=O)=C(SC)N=C21 ZXTDUVJZVFRIDU-UHFFFAOYSA-N 0.000 claims 4
125000005907 alkyl ester group Chemical group 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 abstract description 3
DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 abstract 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 67
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
239000007787 solid Substances 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
235000019439 ethyl acetate Nutrition 0.000 description 23
229940093499 ethyl acetate Drugs 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
239000000725 suspension Substances 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 10
239000003921 oil Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
239000000463 material Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
229940121375 antifungal agent Drugs 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 5
150000003230 pyrimidines Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
125000001246 bromo group Chemical group Br* 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000004821 distillation Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000523 sample Substances 0.000 description 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
241000222122 Candida albicans Species 0.000 description 2
206010017533 Fungal infection Diseases 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
208000031888 Mycoses Diseases 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000004809 Teflon Substances 0.000 description 2
229920006362 Teflon® Polymers 0.000 description 2
230000003266 anti-allergic effect Effects 0.000 description 2
239000003429 antifungal agent Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
125000002843 carboxylic acid group Chemical group 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
229940068968 polysorbate 80 Drugs 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 1
RXBPAXZAOURPOO-UHFFFAOYSA-N 2-methylsulfanylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=CC2=NC(SC)=CC(=O)N21 RXBPAXZAOURPOO-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
208000035657 Abasia Diseases 0.000 description 1
241000220479 Acacia Species 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000222120 Candida <Saccharomycetales> Species 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000893976 Nannizzia gypsea Species 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000002421 anti-septic effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940064004 antiseptic throat preparations Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000003833 bile salt Substances 0.000 description 1
229940093761 bile salts Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
230000000249 desinfective effect Effects 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000002038 ethyl acetate fraction Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
244000053095 fungal pathogen Species 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
229940014259 gelatin Drugs 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
239000002044 hexane fraction Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000006210 lotion Substances 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

CA000450491A 1984-03-26 1984-03-26 Pyrimidones substituees ayant des proprietes antifongiques Expired CA1232904A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000450491A CA1232904A (fr)	1984-03-26	1984-03-26	Pyrimidones substituees ayant des proprietes antifongiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000450491A CA1232904A (fr)	1984-03-26	1984-03-26	Pyrimidones substituees ayant des proprietes antifongiques

Publications (1)

Publication Number	Publication Date
CA1232904A true CA1232904A (fr)	1988-02-16

Family

ID=4127512

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000450491A Expired CA1232904A (fr)	1984-03-26	1984-03-26	Pyrimidones substituees ayant des proprietes antifongiques

Country Status (1)

Country	Link
CA (1)	CA1232904A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1993023398A1 (fr) *	1992-05-13	1993-11-25	E.I. Du Pont De Nemours And Company	Derives de pyrido[1,2-a]pyrimidinone substituee utiles comme fongicides
WO2013050426A1 (fr)	2011-10-04	2013-04-11	Universitetet I Oslo	Inhibiteurs d'anhydrase carbonique

1984
- 1984-03-26 CA CA000450491A patent/CA1232904A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1993023398A1 (fr) *	1992-05-13	1993-11-25	E.I. Du Pont De Nemours And Company	Derives de pyrido[1,2-a]pyrimidinone substituee utiles comme fongicides
WO2013050426A1 (fr)	2011-10-04	2013-04-11	Universitetet I Oslo	Inhibiteurs d'anhydrase carbonique

Legal Events

Date	Code	Title	Description
2005-02-16	MKEX	Expiry

Publication	Publication Date	Title
DE69026980T2 (de)	1997-01-09	Schwefel enthaltende kondensierte Pyrimidinderivate, ihre Herstellung und Verwendung
AU668694B2 (en)	1996-05-16	Saccharin derivative proteolytic enzyme inhibitors
US4794120A (en)	1988-12-27	Antiparasitic nitrofuran derivatives
DE4119767A1 (de)	1992-12-17	Verfahren zur herstellung von (pyrimid-2-yl-thio- bzw. seleno)-essigsaeurederivaten
US5644058A (en)	1997-07-01	Process for preparing 5-substituted pyrrolo-[2,3-d]pyrimidines
FI79319B (fi)	1989-08-31	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara tricykliska oxindolkarboxamidderivat.
US4289879A (en)	1981-09-15	Synthetic method and intermediate for piroxicam
FI89049B (fi)	1993-04-30	Foerfarande foer framstaellning av terapeutiskt anvaendbara tricykliska pyridinderivat och mellanprodukter
US4105778A (en)	1978-08-08	Fused γ-pyrone-2-carboxylic acid derivatives and process therefor
CA1232904A (fr)	1988-02-16	Pyrimidones substituees ayant des proprietes antifongiques
SUZUKI et al.	1979	Synthesis of antimicrobial agents. III. synthesis and antimicrobial activities of thiazolo [5, 4-b] naphthyridine derivatives
Voskressensky et al.	2008	The first example of tetrahydrothieno [3, 2-d] azocines synthesis
CA2053123A1 (fr)	1992-04-13	Composes de thienotriazolodiazepine optiquement actifs
HU181778B (en)	1983-11-28	Process for manufacturing substituted pyrido/1,2-a/ pyrimidines
Ning et al.	1977	Intramolecular nitrene insertion into nitrogen containing rings. Pyrolyses of 3-(1-methyl-2-imidazolyl)-and 3-(1-methyl-5-pyrazolyl)-2, 1-benzisoxazole (anthranils)
SU1151210A3 (ru)	1985-04-15	Способ получени геминальных дигалоидных производных конденсированных пиримидин-4-онов,рацематов или оптически активных антиподов
EP0025643B1 (fr)	1983-08-17	Composés de l'oxo-pyrido(1,2-a)thiénopyrimidine, procédés pour leur préparation, et compositions pharmaceutiques contenant lesdits composés
US4988822A (en)	1991-01-29	Intermediates for preparing 5-aroyl-1,2-dihydro-3H-pyrrolo(1,2-A)pyrrole-1,1-dicarboxylates
US3313818A (en)	1967-04-11	7, 10-dihydro-3, 10-dioxo-7-(lower-alkyl)-3h-pyrano[3, 2-f]quinoline-3-carboxylic acid derivatives
US6201129B1 (en)	2001-03-13	Tricyclic derivatives and their use as anti-cancer agents
FI77869B (fi)	1989-01-31	Foerfarande foer framstaellning av substituerade karboxitiazolo/3,2-a/pyrimidinderivat med en antiallergisk verkan.
Croisy-Delcey et al.	1983	Aza analogs of lucanthone: synthesis and antitumor and bactericidal properties
JPS6019317B2 (ja)	1985-05-15	チエノチアジン誘導体及びその製造方法
KR100248370B1 (ko)	2000-03-15	(-)-3(s)-메틸피리도 벤즈옥사진 중간 유도체의 제조방법
US5278307A (en)	1994-01-11	Process for preparing 4-hydroxypyrrolo(2,3-d)pyrimidine based antifolate compounds and intermediates

CA1232904A - Pyrimidones substituees ayant des proprietes antifongiques - Google Patents

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