CS159591A3 - Azole derivatives, process for their production and pharmaceutical containing them - Google Patents

Azole derivatives, process for their production and pharmaceutical containing them Download PDF

Info

Publication number: CS159591A3
Authority: CS; Czechoslovakia
Prior art keywords: furyl; amino; formula; compound; triazine
Prior art date: 1990-05-29

Application number

CS911595A

Other languages

Czech (cs)

English (en)

Inventor

Peter William Rodney Caulkett

Geraint Jones

Michael George Collis

Simon Martin Poucher

Original Assignee

Ici Plc

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.)

1990-05-29

Filing date

1991-05-28

Publication date

1992-01-15

1990-05-29 Priority claimed from GB909011914A external-priority patent/GB9011914D0/en

1990-05-29 Priority claimed from GB909011913A external-priority patent/GB9011913D0/en

1991-01-22 Priority claimed from GB919101380A external-priority patent/GB9101380D0/en

1991-01-22 Priority claimed from GB919101379A external-priority patent/GB9101379D0/en

1991-02-27 Priority claimed from GB919104125A external-priority patent/GB9104125D0/en

1991-05-28 Application filed by Ici Plc filed Critical Ici Plc

1992-01-15 Publication of CS159591A3 publication Critical patent/CS159591A3/cs

Links

238000000034 method Methods 0.000 title claims description 38
230000008569 process Effects 0.000 title claims description 14
150000007980 azole derivatives Chemical class 0.000 title description 6
238000004519 manufacturing process Methods 0.000 title description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 225
229910052757 nitrogen Inorganic materials 0.000 claims description 218
229910052799 carbon Inorganic materials 0.000 claims description 207
-1 5-membered heteroaryl radical Chemical group 0.000 claims description 200
150000001875 compounds Chemical class 0.000 claims description 179
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 173
125000004432 carbon atom Chemical group C* 0.000 claims description 75
125000000217 alkyl group Chemical group 0.000 claims description 68
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
239000001257 hydrogen Substances 0.000 claims description 42
150000003839 salts Chemical class 0.000 claims description 31
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
125000002541 furyl group Chemical group 0.000 claims description 28
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
239000007858 starting material Substances 0.000 claims description 21
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 18
125000001424 substituent group Chemical group 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 15
125000000753 cycloalkyl group Chemical group 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 12
239000003085 diluting agent Substances 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 7
125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 7
125000003884 phenylalkyl group Chemical group 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 5
125000000842 isoxazolyl group Chemical group 0.000 claims description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000000547 substituted alkyl group Chemical group 0.000 claims description 5
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
125000001072 heteroaryl group Chemical group 0.000 claims description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
230000008707 rearrangement Effects 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 claims description 2
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000005336 allyloxy group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000001786 isothiazolyl group Chemical group 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
101150009274 nhr-1 gene Proteins 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 8
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 1
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 1
230000002152 alkylating effect Effects 0.000 claims 1
125000002971 oxazolyl group Chemical group 0.000 claims 1
GGFBICGBDXVAGX-UHFFFAOYSA-N propylaluminum Chemical compound [Al].[CH2]CC GGFBICGBDXVAGX-UHFFFAOYSA-N 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 372
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 112
239000007787 solid Substances 0.000 description 109
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 54
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 46
239000013078 crystal Substances 0.000 description 46
239000002904 solvent Substances 0.000 description 46
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 45
238000012360 testing method Methods 0.000 description 37
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
239000000203 mixture Substances 0.000 description 32
239000002126 C01EB10 - Adenosine Substances 0.000 description 31
229960005305 adenosine Drugs 0.000 description 31
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 24
239000000725 suspension Substances 0.000 description 23
229910001868 water Inorganic materials 0.000 description 23
238000004458 analytical method Methods 0.000 description 22
101100138673 Arabidopsis thaliana NPF3.1 gene Proteins 0.000 description 21
238000000354 decomposition reaction Methods 0.000 description 20
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 19
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 17
230000000694 effects Effects 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
238000004587 chromatography analysis Methods 0.000 description 16
229960004592 isopropanol Drugs 0.000 description 16
238000010992 reflux Methods 0.000 description 16
239000000377 silicon dioxide Substances 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 14
238000001953 recrystallisation Methods 0.000 description 14
239000012267 brine Substances 0.000 description 13
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
229910000041 hydrogen chloride Inorganic materials 0.000 description 13
230000004044 response Effects 0.000 description 13
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
BIXYYZIIJIXVFW-UUOKFMHZSA-N (2R,3R,4S,5R)-2-(6-amino-2-chloro-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BIXYYZIIJIXVFW-UUOKFMHZSA-N 0.000 description 12
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 12
238000004452 microanalysis Methods 0.000 description 12
239000003921 oil Substances 0.000 description 12
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
150000001298 alcohols Chemical class 0.000 description 9
238000003556 assay Methods 0.000 description 9
238000002425 crystallisation Methods 0.000 description 9
230000008025 crystallization Effects 0.000 description 9
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000000872 buffer Substances 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 8
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 7
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 7
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
239000007789 gas Substances 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
229910052760 oxygen Inorganic materials 0.000 description 7
229960000278 theophylline Drugs 0.000 description 7
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 6
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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229910052783 alkali metal Inorganic materials 0.000 description 6
239000005557 antagonist Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
230000001965 increasing effect Effects 0.000 description 6
239000003112 inhibitor Substances 0.000 description 6
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 6
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 6
239000000296 purinergic P1 receptor antagonist Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
125000004149 thio group Chemical group *S* 0.000 description 6
150000003573 thiols Chemical class 0.000 description 6
230000002792 vascular Effects 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
125000004414 alkyl thio group Chemical group 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
230000003042 antagnostic effect Effects 0.000 description 5
210000001367 artery Anatomy 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
230000027455 binding Effects 0.000 description 5
230000017531 blood circulation Effects 0.000 description 5
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
230000033764 rhythmic process Effects 0.000 description 5
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
241000700199 Cavia porcellus Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
241000282326 Felis catus Species 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 description 4
230000001746 atrial effect Effects 0.000 description 4
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
239000000463 material Substances 0.000 description 4
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
238000000746 purification Methods 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
230000000304 vasodilatating effect Effects 0.000 description 4
210000003462 vein Anatomy 0.000 description 4
238000005303 weighing Methods 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
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XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
210000002027 skeletal muscle Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
BYMHXIQVEAYSJD-UHFFFAOYSA-M sodium;4-sulfophenolate Chemical compound [Na+].OC1=CC=C(S([O-])(=O)=O)C=C1 BYMHXIQVEAYSJD-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
230000008023 solidification Effects 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000032258 transport Effects 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
238000001665 trituration Methods 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
210000000689 upper leg Anatomy 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
238000004078 waterproofing Methods 0.000 description 1
229960004928 xamoterol Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CS911595A 1990-05-29 1991-05-28 Azole derivatives, process for their production and pharmaceutical containing them CS159591A3 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
GB909011914A GB9011914D0 (en)	1990-05-29	1990-05-29	Heterocyclic compounds
GB909011913A GB9011913D0 (en)	1990-05-29	1990-05-29	Azole derivatives
GB919101380A GB9101380D0 (en)	1991-01-22	1991-01-22	Azole derivatives
GB919101379A GB9101379D0 (en)	1991-01-22	1991-01-22	Heterocyclic compounds
GB919104125A GB9104125D0 (en)	1991-02-27	1991-02-27	Azole derivatives

Publications (1)

Publication Number	Publication Date
CS159591A3 true CS159591A3 (en)	1992-01-15

Family

ID=27516979

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS911595A CS159591A3 (en)	1990-05-29	1991-05-28	Azole derivatives, process for their production and pharmaceutical containing them

Country Status (20)

Country	Link
US (1)	US5270311A (fr)
EP (1)	EP0459702A1 (fr)
JP (1)	JP2504879B2 (fr)
KR (1)	KR910020012A (fr)
CN (1)	CN1056879A (fr)
AP (1)	AP248A (fr)
AU (1)	AU642494B2 (fr)
CA (1)	CA2043424A1 (fr)
CS (1)	CS159591A3 (fr)
FI (1)	FI912563A7 (fr)
GB (1)	GB2244487B (fr)
HU (1)	HUT61311A (fr)
IE (1)	IE911818A1 (fr)
IL (1)	IL98316A (fr)
NO (1)	NO178401C (fr)
NZ (1)	NZ238288A (fr)
OA (1)	OA09358A (fr)
PT (1)	PT97776A (fr)
RO (1)	RO109542B1 (fr)
YU (1)	YU47812B (fr)

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GB2244487B (en) *	1990-05-29	1994-02-02	Ici Plc	Azole derivatives
GB9226735D0 (en) *	1992-12-22	1993-02-17	Ici Plc	Azole derivatives
US5356894A (en) *	1990-05-29	1994-10-18	Rodney Peter W	Morpholinyl substituted [1,2,4]-triazolo[1,5-a]triazine as antagonist
GB9111130D0 (en) *	1991-05-23	1991-07-17	Ici Plc	Azole derivatives
GB9111131D0 (en) *	1991-05-23	1991-07-17	Ici Plc	Heterocyclic compounds
GB9125001D0 (en) *	1991-11-25	1992-01-22	Ici Plc	Heterocyclic compounds
GB9124968D0 (en) *	1991-11-25	1992-01-22	Ici Plc	Chemical process
GB9125002D0 (en) *	1991-11-25	1992-01-22	Ici Plc	Azole derivatives
ES2165393T3 (es) *	1993-07-27	2002-03-16	Kyowa Hakko Kogyo Kk	Remedio contra la enfermedad de parkinson.
AU7546794A (en) *	1993-09-06	1995-03-27	Kyowa Hakko Kogyo Co. Ltd.	Depression remedy
CA2284737C (fr)	1997-03-24	2007-03-13	Kyowa Hakko Kogyo Co., Ltd.	Derives [1,2,4]triazolo[1,5-c]pyrimidiniques
US6060481A (en) *	1998-05-28	2000-05-09	The Penn State Research Foundation	Method for improving insulin sensitivity using an adenosine receptor antagonist
AU756144B2 (en)	1998-09-22	2003-01-02	Kyowa Hakko Kogyo Co. Ltd.	(1,2,4)triazolo(1,5-c)pyrimidine derivatives
AU2003272886A1 (en) *	2002-09-24	2004-04-19	Kyowa Hakko Kogyo Co., Ltd.	(1,2,4)-TRIAZOLO(1,5-c)PYRIMIDINE DERIVATIVE
US7329658B2 (en) *	2003-02-06	2008-02-12	Pfizer Inc	Cannabinoid receptor ligands and uses thereof
WO2004092170A2 (fr) *	2003-04-09	2004-10-28	Biogen Idec Ma Inc.	Triazolotriazines et pyrazolotriazines et leurs procedes de fabrication et d'utilisation
US20070010522A1 (en) *	2003-04-09	2007-01-11	Chi Vu	Triazolo[1,5-c]pyrimidines and pyrazolo[1,5-c]pyrimidines useful as a2a adenosine receptor antagonists
US7674791B2 (en)	2003-04-09	2010-03-09	Biogen Idec Ma Inc.	Triazolopyrazines and methods of making and using the same
DE602004018637D1 (de)	2003-04-09	2009-02-05	Biogen Idec Inc	A2a-adenosinrezeptorantagonisten
WO2004110454A1 (fr) *	2003-06-13	2004-12-23	Ishihara Sangyo Kaisha, Ltd.	Composition de traitement ou de prevention de maladies necessitant l'administration d'un agoniste du recepteur a2a de l'adenosine
WO2006076706A1 (fr)	2005-01-14	2006-07-20	Millennium Pharmaceuticals, Inc.	Derives de cinnamide et d'hydrocinnamide presentant une activite inhibitrice de raf-kinase
BR112015013195A2 (pt)	2012-12-06	2017-08-29	Siemens Ag	Disposição e método para introduzir calor em uma formação geológica por meio de indução eletromagnética
CN106916073A (zh) *	2017-01-20	2017-07-04	上海巧坤化工科技有限公司	一种大麦芽碱盐酸盐的合成方法
CA3089159A1 (fr) *	2018-02-06	2019-08-15	Jiangsu Hengrui Medicine Co., Ltd.	Derive de pyrazolo[1,5-a][1,3,5]triazine-2-amine, son procede de preparation et son utilisation medicale
WO2020002969A1 (fr) *	2018-06-26	2020-01-02	Zhejiang Vimgreen Pharmaceuticals, Ltd	Dérivés de triazolotriazine en tant qu'antagonistes du récepteur a2a
KR102633145B1 (ko) *	2018-06-26	2024-02-05	쩌지앙 빔그린 파머슈티컬스, 엘티디	A2a 수용체 길항제로서의 트리아졸로 트리아진 유도체
BE1026602B1 (fr)	2018-09-27	2020-06-18	Iteos Therapeutics S A	Inhibiteurs d’a2a ne penetrant pas dans le cerveau et methodes d’utilisation dans le traitement de cancers
WO2020103939A1 (fr) *	2018-11-22	2020-05-28	上海科技大学	Composé à cycle triazolo, son procédé de préparation, intermédiaires de celui-ci et utilisation associée
CN112608316B (zh) *	2019-07-30	2022-10-21	厦门宝太生物科技股份有限公司	一种吡唑并三嗪类腺苷受体拮抗剂
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CN114901665B (zh) *	2019-12-26	2025-02-18	浙江春禾医药科技有限公司	三唑并三嗪衍生物在治疗疾病中的用途
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US3846423A (en) *	1972-06-08	1974-11-05	Icn Pharmaceuticals	Pyrazolo (1,5a) 1,3,5-triazines
BE815405A (fr) *	1973-05-22	1974-11-22		NOUVEAUX DERIVES DE LA PYRAZOLO(1,5-a)-S-TRIAZINE LEUR PREPARATION ET LEUR APPLICATION COMME MEDICAMENTS
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GB1579932A (en) *	1976-05-12	1980-11-26	Ici Ltd	Herbicidal triazolotriazines
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AU2192683A (en) *	1982-12-30	1984-07-05	Biomeasure Incorporated	Pyrazolo(1,5-alpha)-1,3,5-triazines
CA1267143A (fr) *	1985-06-06	1990-03-27	Sun H. Kim	Derives de 7-phenylpyrazole[1,5-a]-1,3,5-triazine, agents anti-arthrite
DE3677445D1 (de) *	1985-09-30	1991-03-14	Ciba Geigy Ag	2-substituierte-e-kondensierte(1,5-c)-pyrimidine, pharmazeutische zubereitungen und ihre verwendung.
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US4970142A (en) *	1989-02-16	1990-11-13	Konica Corporation	Silver halide photographic light-sensitive material containing cyan coupler
GB2244487B (en) *	1990-05-29	1994-02-02	Ici Plc	Azole derivatives

1991
- 1991-05-23 GB GB9111132A patent/GB2244487B/en not_active Expired - Fee Related
- 1991-05-23 EP EP91304665A patent/EP0459702A1/fr not_active Withdrawn
- 1991-05-28 CS CS911595A patent/CS159591A3/cs unknown
- 1991-05-28 AU AU77348/91A patent/AU642494B2/en not_active Ceased
- 1991-05-28 CA CA002043424A patent/CA2043424A1/fr not_active Abandoned
- 1991-05-28 FI FI912563A patent/FI912563A7/fi not_active Application Discontinuation
- 1991-05-28 IE IE181891A patent/IE911818A1/en unknown
- 1991-05-28 RO RO147639A patent/RO109542B1/ro unknown
- 1991-05-28 YU YU94791A patent/YU47812B/sh unknown
- 1991-05-28 NO NO912051A patent/NO178401C/no unknown
- 1991-05-28 US US07/708,265 patent/US5270311A/en not_active Expired - Lifetime
- 1991-05-28 NZ NZ238288A patent/NZ238288A/xx unknown
- 1991-05-28 AP APAP/P/1991/000266A patent/AP248A/en active
- 1991-05-28 KR KR1019910008926A patent/KR910020012A/ko not_active Withdrawn
- 1991-05-28 PT PT97776A patent/PT97776A/pt not_active Application Discontinuation
- 1991-05-29 JP JP3235332A patent/JP2504879B2/ja not_active Expired - Fee Related
- 1991-05-29 OA OA60010A patent/OA09358A/fr unknown
- 1991-05-29 HU HU911789A patent/HUT61311A/hu unknown
- 1991-05-29 CN CN91103744A patent/CN1056879A/zh active Pending
- 1991-05-30 IL IL9831691A patent/IL98316A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPH0597855A (ja)	1993-04-20
HU911789D0 (en)	1991-12-30
EP0459702A1 (fr)	1991-12-04
OA09358A (fr)	1992-09-15
HUT61311A (en)	1992-12-28
YU94791A (sh)	1994-06-24
FI912563A0 (fi)	1991-05-28
AU7734891A (en)	1991-12-05
GB9111132D0 (en)	1991-07-17
KR910020012A (ko)	1991-12-19
NO178401C (no)	1996-03-20
AU642494B2 (en)	1993-10-21
CA2043424A1 (fr)	1991-11-30
IL98316A (en)	1995-05-26
GB2244487A (en)	1991-12-04
NO178401B (no)	1995-12-11
NZ238288A (en)	1993-07-27
IE911818A1 (en)	1991-12-04
AP248A (en)	1993-03-16
JP2504879B2 (ja)	1996-06-05
NO912051L (no)	1991-12-02
NO912051D0 (no)	1991-05-28
AP9100266A0 (en)	1991-07-31
US5270311A (en)	1993-12-14
FI912563A7 (fi)	1991-11-30
GB2244487B (en)	1994-02-02
YU47812B (sr)	1996-01-09
PT97776A (pt)	1992-03-31
CN1056879A (zh)	1991-12-11
IL98316A0 (en)	1992-06-21
RO109542B1 (ro)	1995-03-30

Publication	Publication Date	Title
CS159591A3 (en)	1992-01-15	Azole derivatives, process for their production and pharmaceutical containing them
US5356894A (en)	1994-10-18	Morpholinyl substituted [1,2,4]-triazolo[1,5-a]triazine as antagonist
US7410966B2 (en)	2008-08-12	Use of and some novel imidazopyridines
RU2572593C2 (ru)	2016-01-20	Производные n-[(1н-пиразол-1-ил) арил]-1н-индола или 1н-индазол-3-карбоксамида, их получение и их применение в качестве антагонистов p2y12
JPH08295667A (ja)	1996-11-12	複素環化合物、その製造法および剤
EP3515888B1 (fr)	2021-03-31	Antagonistes de trpv4
CA2899646A1 (fr)	2014-09-18	Xanthines substituees et leurs methodes d'utilisation
BR112013004750B1 (pt)	2021-06-15	Derivados de quinolina e quinoxalina como inibidores da cinase
JPH06104666B2 (ja)	1994-12-21	２―置換―ｅ―縮合―〔１，２，４〕トリアゾロ〔１，５―ｃ〕ピリミジン類及びそれを含有する医薬組成物
US6960583B2 (en)	2005-11-01	Pyrazolotriazines as CRF antagonists
JP2011511082A (ja)	2011-04-07	二重ファルマコフォア−ｐｄｅ４‐ムスカリン性アンタゴニスト
DE69029303T2 (de)	1997-05-28	5-Triazolo(3,4-i)purinderivate
US5254548A (en)	1993-10-19	Compounds having an aryltriazine structure
KR20180124737A (ko)	2018-11-21	피라졸로 피리미딘 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 암, 자가면역질환 및 뇌질환의 예방 또는 치료용 약학적 조성물
HRP970413A2 (en)	1998-10-31	Azolo triazines and pyrimidines
US5380714A (en)	1995-01-10	2-furyl-triazalo [1,5-a]-[1,3,5]triazines and pyrazolo [2,3-a][1,3,5]triazines
Sirisha et al.	2014	Design, synthesis and evaluation of new 2, 6-dihydroimidazo [1, 2-c] pyrimido [5, 4-e]-pyrimidine-5 (3H)-thiones as possible antihistaminic/antiasthmatic agents
JP2011511083A (ja)	2011-04-07	二重ファルマコフォア−ｐｄｅ４‐ムスカリン性アンタゴニスト
ES2254778T3 (es)	2006-06-16	Triazoloquinoxalinas sustituidas con pirazolilo.
HRP931512A2 (en)	1994-12-31	Azole derivatives
KR101796779B1 (ko)	2017-11-10	다이하이드로프테리딘-온 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 포함하는 pi3 키나아제 관련 질환의 예방 또는 치료용 약학적 조성물
US20070043064A1 (en)	2007-02-22	7-Substituted 3-nitro-pyrazo[1,5-a] pyrimidines
ES2707734T3 (es)	2019-04-04	Derivados de carboxamida
KR101459720B1 (ko)	2014-11-12	세로토닌 5-ＨＴ6 저해 활성을 갖는 5-설포닐아미노-5,6-다이하이드로-1Ｈ-피라졸로[3,4-ｃ]피리딘-7(4Ｈ)-온 화합물
JPH08301871A (ja)	1996-11-19	縮合複素環化合物およびその製造法