NO323314B1 - Fremgangsmate for fremstilling av pyrimidonderivater med antifungal aktivitet - Google Patents

Fremgangsmate for fremstilling av pyrimidonderivater med antifungal aktivitet Download PDF

Info

Publication number: NO323314B1
Authority: NO; Norway
Prior art keywords: group; denotes; alkyl; haloalkyl; formula
Prior art date: 2000-03-07

Application number

NO20024256A

Other languages

English (en)

Norwegian (no)

Other versions

NO20024256D0 (no

NO20024256L (no

Inventor

Javier Bartoli Orpi

Manuel Anguita Lopez

Original Assignee

Uriach Y Compania Sa J

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.)

2000-03-07

Filing date

2002-09-06

Publication date

2007-03-12

2002-09-06 Application filed by Uriach Y Compania Sa J filed Critical Uriach Y Compania Sa J

2002-09-06 Publication of NO20024256D0 publication Critical patent/NO20024256D0/no

2002-09-06 Publication of NO20024256L publication Critical patent/NO20024256L/no

2007-03-12 Publication of NO323314B1 publication Critical patent/NO323314B1/no

Links

238000000034 method Methods 0.000 title claims description 25
150000008318 pyrimidones Chemical class 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 7
230000000843 anti-fungal effect Effects 0.000 title description 3
-1 C 1 -C 4 alkoxy Chemical group 0.000 claims description 43
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical group 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 6
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 6
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 4
QQIRAVWVGBTHMJ-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;lithium Chemical compound [Li].C[Si](C)(C)N[Si](C)(C)C QQIRAVWVGBTHMJ-UHFFFAOYSA-N 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
239000002798 polar solvent Substances 0.000 claims description 4
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims description 4
QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
FYJKEHKQUPSJDH-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;potassium Chemical compound [K].C[Si](C)(C)N[Si](C)(C)C FYJKEHKQUPSJDH-UHFFFAOYSA-N 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims description 2
239000012312 sodium hydride Substances 0.000 claims description 2
229910000104 sodium hydride Inorganic materials 0.000 claims description 2
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 2
PMLONMIODRHERC-UHFFFAOYSA-N 7-chloro-1h-quinazolin-4-one Chemical compound N1C=NC(=O)C=2C1=CC(Cl)=CC=2 PMLONMIODRHERC-UHFFFAOYSA-N 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000002253 acid Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
QNEJYHVIYJFNHC-UHFFFAOYSA-N 2-amino-4-chlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C=C1N QNEJYHVIYJFNHC-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000001409 amidines Chemical class 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
150000007980 azole derivatives Chemical class 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
244000309464 bull Species 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
ZJSQZQMVXKZAGW-UHFFFAOYSA-N 2H-benzotriazol-4-ol hydrate Chemical compound O.OC1=CC=CC2=C1N=NN2 ZJSQZQMVXKZAGW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000005997 bromomethyl group Chemical group 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
239000004202 carbamide Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
125000006343 heptafluoro propyl group Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000011630 iodine Substances 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
239000000463 material Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO20024256A 2000-03-07 2002-09-06 Fremgangsmate for fremstilling av pyrimidonderivater med antifungal aktivitet NO323314B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ES200000625A ES2159488B1 (es)	2000-03-07	2000-03-07	Procedimiento para la preparacion de derivados de pirimidona con actividad antifungica.
PCT/ES2001/000081 WO2001066519A2 (es)	2000-03-07	2001-03-05	Procedimiento para la preparacion de derivados de pirimidona con actividad antifungica

Publications (3)

Publication Number	Publication Date
NO20024256D0 NO20024256D0 (no)	2002-09-06
NO20024256L NO20024256L (no)	2002-09-06
NO323314B1 true NO323314B1 (no)	2007-03-12

Family

ID=8492714

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20024256A NO323314B1 (no)	2000-03-07	2002-09-06	Fremgangsmate for fremstilling av pyrimidonderivater med antifungal aktivitet

Country Status (17)

Country	Link
US (1)	US6653475B2 (de)
EP (1)	EP1282084B9 (de)
JP (1)	JP4772248B2 (de)
KR (1)	KR100735583B1 (de)
AR (1)	AR027607A1 (de)
AT (1)	ATE250256T1 (de)
AU (1)	AU2001237447A1 (de)
BR (1)	BRPI0108990B8 (de)
CA (1)	CA2402390C (de)
DE (1)	DE60100810T2 (de)
DK (1)	DK1282084T3 (de)
ES (2)	ES2159488B1 (de)
HK (1)	HK1052244B (de)
MX (1)	MXPA02008556A (de)
NO (1)	NO323314B1 (de)
PT (1)	PT1282084E (de)
WO (1)	WO2001066519A2 (de)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
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US7230000B1 (en)	1999-10-27	2007-06-12	Cytokinetics, Incorporated	Methods and compositions utilizing quinazolinones
US6545004B1 (en)	1999-10-27	2003-04-08	Cytokinetics, Inc.	Methods and compositions utilizing quinazolinones
EP1477481B1 (de) *	2002-01-28	2009-07-22	Ube Industries, Ltd.	Verfahren zur herstellung eines chinazolin-4-onderivats
US7009049B2 (en)	2002-02-15	2006-03-07	Cytokinetics, Inc.	Syntheses of quinazolinones
AU2003270015A1 (en)	2002-05-09	2003-12-02	Cytokinetics, Inc.	Compounds, compositions, and methods
US7166595B2 (en)	2002-05-09	2007-01-23	Cytokinetics, Inc.	Compounds, methods and compositions
WO2003103575A2 (en)	2002-05-23	2003-12-18	Cytokinetics, Inc.	Compounds, compositions, and methods
CA2489367A1 (en)	2002-06-14	2003-12-24	Cytokinetics, Inc.	Compounds, compositions, and methods
WO2004009036A2 (en)	2002-07-23	2004-01-29	Cytokinetics, Inc.	Compounds compositions and methods
WO2004034972A2 (en)	2002-09-30	2004-04-29	Cytokinetics, Inc.	Compounds, compositions, and methods
EP1692112A4 (de)	2003-12-08	2008-09-24	Cytokinetics Inc	Verbindungen, zusammensetzungen und verfahren
JP5055263B2 (ja)	2005-03-30	2012-10-24	ダエウンファーマシューティカルカンパニーリミテッド	抗真菌性トリアゾール誘導体
EP2049504A4 (de) *	2006-08-07	2010-09-22	Stiefel Laboratories	Antifungale kristallverbindungen
EP2009009A1 (de) *	2007-06-26	2008-12-31	Palau Pharma, S.A.	Antifungale Kristallverbindungen
EP1887004A1 (de) *	2006-08-07	2008-02-13	Palau Pharma, S.A.	Kristalline Formen von (1R,2R)-7-Chloro-3-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]chinazolin-4(3H)-on
TWI395728B (zh)	2006-12-06	2013-05-11	Du Pont	製備２-胺基-５-氰基苯甲酸衍生物之方法
TWI415827B (zh)	2006-12-21	2013-11-21	Du Pont	製備２-胺基-５-氰基苯甲酸衍生物之方法
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Publication number	Publication date
HK1052244A1 (en)	2003-09-05
KR100735583B1 (ko)	2007-07-04
US6653475B2 (en)	2003-11-25
EP1282084B9 (de)	2005-03-02
ATE250256T1 (de)	2003-10-15
AR027607A1 (es)	2003-04-02
CA2402390A1 (en)	2001-09-13
NO20024256D0 (no)	2002-09-06
WO2001066519A2 (es)	2001-09-13
BR0108990B1 (pt)	2014-03-25
EP1282084B1 (de)	2003-09-17
CA2402390C (en)	2009-09-15
DK1282084T3 (da)	2004-02-02
AU2001237447A1 (en)	2001-09-17
ES2207605T3 (es)	2004-06-01
DE60100810D1 (de)	2003-10-23
DE60100810T2 (de)	2004-07-01
ES2159488A1 (es)	2001-10-01
BR0108990A (pt)	2003-12-30
JP2004500391A (ja)	2004-01-08
WO2001066519A3 (es)	2002-01-31
EP1282084A2 (de)	2003-02-05
JP4772248B2 (ja)	2011-09-14
BRPI0108990B8 (pt)	2021-05-25
ES2159488B1 (es)	2002-04-16
KR20020075809A (ko)	2002-10-05
NO20024256L (no)	2002-09-06
PT1282084E (pt)	2004-02-27
HK1052244B (en)	2003-12-19
US20030064986A1 (en)	2003-04-03
MXPA02008556A (es)	2003-02-24

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EP1282084B9 (de)	2005-03-02	Verfahren zur präparation von pyrimidonderivaten mit fungizidder aktivität
EP0783501B9 (de)	2001-07-25	Pyrimidonderivate mit antifungaler wirkung
MXPA97002382A (en)	1998-02-01	New pyrimidone derivatives with activityantifung
HU217907B (hu)	2000-05-28	Kinolin- vagy kinazolinszármazékok, eljárás a vegyületek előállítására és a vegyületeket tartalmazó gyógyászati készítmények
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CZ304209B6 (cs)	2014-01-08	Hydrazonoylové deriváty
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