DE3237243A1 - 1-phenyl-1h-pyrazolo (3,4-b) pyrazinderivate und verfahren zu ihrer herstellung - Google Patents
1-phenyl-1h-pyrazolo (3,4-b) pyrazinderivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE3237243A1 DE3237243A1 DE19823237243 DE3237243A DE3237243A1 DE 3237243 A1 DE3237243 A1 DE 3237243A1 DE 19823237243 DE19823237243 DE 19823237243 DE 3237243 A DE3237243 A DE 3237243A DE 3237243 A1 DE3237243 A1 DE 3237243A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- deep
- formula
- phenyl
- substituted
- Prior art date
- 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.)
- Granted
Links
- ZKNORTOOYUPROW-UHFFFAOYSA-N 1-phenylpyrazolo[3,4-b]pyrazine Chemical class C12=NC=CN=C2C=NN1C1=CC=CC=C1 ZKNORTOOYUPROW-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
- 125000005843 halogen group Chemical group 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 150000003216 pyrazines Chemical class 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- -1 alkyl amide Chemical class 0.000 abstract description 32
- 206010028980 Neoplasm Diseases 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000010183 spectrum analysis Methods 0.000 description 6
- QSXRUMZWAOWFCH-UHFFFAOYSA-N 5-chloro-1-phenylpyrazolo[3,4-b]pyrazine Chemical compound N1=CC2=NC(Cl)=CN=C2N1C1=CC=CC=C1 QSXRUMZWAOWFCH-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- 229910052801 chlorine Inorganic materials 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
- 241000700605 Viruses Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- KJHVLZPEVUUHJP-UHFFFAOYSA-N 1-(3-chlorophenyl)pyrazolo[3,4-b]pyrazine Chemical compound ClC1=CC=CC(N2C3=NC=CN=C3C=N2)=C1 KJHVLZPEVUUHJP-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XAMVESMKADVTKU-UHFFFAOYSA-N 1-phenylpyrazolo[3,4-b]pyrazine-5-carbonitrile Chemical compound N1=CC2=NC(C#N)=CN=C2N1C1=CC=CC=C1 XAMVESMKADVTKU-UHFFFAOYSA-N 0.000 description 1
- DDZGQYREBDXECY-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyrazine Chemical class C1=CN=C2C=NNC2=N1 DDZGQYREBDXECY-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- ZVNYYNAAEVZNDW-UHFFFAOYSA-N 2-phenylpyrazol-3-amine Chemical compound NC1=CC=NN1C1=CC=CC=C1 ZVNYYNAAEVZNDW-UHFFFAOYSA-N 0.000 description 1
- NDWSQHPRNWYCAH-UHFFFAOYSA-N 2-phenylpyrazole-3,4-diamine Chemical compound NC1=C(N)C=NN1C1=CC=CC=C1 NDWSQHPRNWYCAH-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- GLKNSXRJKZBVGW-UHFFFAOYSA-N 4-nitroso-2-phenylpyrazol-3-amine;hydrochloride Chemical compound Cl.NC1=C(N=O)C=NN1C1=CC=CC=C1 GLKNSXRJKZBVGW-UHFFFAOYSA-N 0.000 description 1
- RACMYRHRVLBXSN-UHFFFAOYSA-N 5-(4-bromophenoxy)-1-phenylpyrazolo[3,4-b]pyrazine Chemical compound C1=CC(Br)=CC=C1OC1=CN=C(N(N=C2)C=3C=CC=CC=3)C2=N1 RACMYRHRVLBXSN-UHFFFAOYSA-N 0.000 description 1
- KWUDERFRTNRCFV-UHFFFAOYSA-N 5-(4-methylphenyl)sulfonyl-1-phenylpyrazolo[3,4-b]pyrazine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CN=C(N(N=C2)C=3C=CC=CC=3)C2=N1 KWUDERFRTNRCFV-UHFFFAOYSA-N 0.000 description 1
- BFMGSMOYBHOHGI-UHFFFAOYSA-N 5-amino-1-phenylpyrazole-4-carboxylic acid Chemical compound NC1=C(C(O)=O)C=NN1C1=CC=CC=C1 BFMGSMOYBHOHGI-UHFFFAOYSA-N 0.000 description 1
- VGYLRPGYXSGGSX-UHFFFAOYSA-N 5-butan-2-yloxy-1-phenylpyrazolo[3,4-b]pyrazine Chemical compound N1=CC2=NC(OC(C)CC)=CN=C2N1C1=CC=CC=C1 VGYLRPGYXSGGSX-UHFFFAOYSA-N 0.000 description 1
- IBXSPHBBDFBQHH-UHFFFAOYSA-N 5-hexoxy-1-phenylpyrazolo[3,4-b]pyrazine Chemical compound N1=CC2=NC(OCCCCCC)=CN=C2N1C1=CC=CC=C1 IBXSPHBBDFBQHH-UHFFFAOYSA-N 0.000 description 1
- WFESWJOKLRJGRX-UHFFFAOYSA-N 5-methoxy-1-phenylpyrazolo[3,4-b]pyrazine Chemical compound N1=CC2=NC(OC)=CN=C2N1C1=CC=CC=C1 WFESWJOKLRJGRX-UHFFFAOYSA-N 0.000 description 1
- DAKMDBJCDYUINW-UHFFFAOYSA-N 5-phenoxy-1-phenylpyrazolo[3,4-b]pyrazine Chemical compound C=1N=C2N(C=3C=CC=CC=3)N=CC2=NC=1OC1=CC=CC=C1 DAKMDBJCDYUINW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 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
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical group CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1722782A JPH0240671B2 (ja) | 1982-02-05 | 1982-02-05 | 11fueniruu1hhpirazoro*3*44b*pirajinjudotai |
| JP6367582A JPH0240672B2 (ja) | 1982-04-16 | 1982-04-16 | 55fueniruaminoo11fueniruu1hhpirazoro*3*44b*pirajinjudotai |
| JP6367682A JPS58180486A (ja) | 1982-04-16 | 1982-04-16 | ５−フエニルオキシ−１−フエニル−１Ｈ−ピラゾロ〔３，４−ｂ〕ピラジン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3237243A1 true DE3237243A1 (de) | 1983-08-18 |
| DE3237243C2 DE3237243C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-10-27 |
Family
ID=27281730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823237243 Granted DE3237243A1 (de) | 1982-02-05 | 1982-10-07 | 1-phenyl-1h-pyrazolo (3,4-b) pyrazinderivate und verfahren zu ihrer herstellung |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4460773A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
| DE (1) | DE3237243A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3432983A1 (de) * | 1983-09-07 | 1985-04-18 | Lion Corp., Tokio/Tokyo | 1,5-disubstituierte 1h-pyrazolo(3,4-b)-pyrazin-derivate und antitumormittel, die diese enthalten |
| AP89A (en) * | 1987-08-15 | 1990-06-14 | The Wellcome Foundation Ltd | Heterocyclic compounds. |
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| WO2012088266A2 (en) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3 |
| US9611267B2 (en) | 2012-06-13 | 2017-04-04 | Incyte Holdings Corporation | Substituted tricyclic compounds as FGFR inhibitors |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| HRP20180365T2 (hr) | 2013-04-19 | 2019-06-28 | Incyte Holdings Corporation | Biciklički heterocikli kao inhibitori fgfr |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| EP3617205B1 (en) | 2015-02-20 | 2021-08-04 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| PL3788047T3 (pl) | 2018-05-04 | 2025-04-14 | Incyte Corporation | Stałe postacie inhibitora fgfr i sposoby ich otrzymywania |
| SG11202010882XA (en) | 2018-05-04 | 2020-11-27 | Incyte Corp | Salts of an fgfr inhibitor |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| WO2021007269A1 (en) | 2019-07-09 | 2021-01-14 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| AU2020366006A1 (en) | 2019-10-14 | 2022-04-21 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021113479A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| WO2021113462A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Derivatives of an fgfr inhibitor |
| US12012409B2 (en) | 2020-01-15 | 2024-06-18 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| TW202304459A (zh) | 2021-04-12 | 2023-02-01 | 美商英塞特公司 | 包含ｆｇｆｒ抑制劑及ｎｅｃｔｉｎ－４靶向劑之組合療法 |
| US11939331B2 (en) | 2021-06-09 | 2024-03-26 | Incyte Corporation | Tricyclic heterocycles as FGFR inhibitors |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3957782A (en) * | 1974-12-16 | 1976-05-18 | E. R. Squibb & Sons, Inc. | Pyrazolo [3,4-b]pyrazine-5-carboxylic acids, esters, nitriles and amides |
| US4303658A (en) * | 1980-05-12 | 1981-12-01 | Abbott Laboratories | Antiviral pyrazolopyrazines |
-
1982
- 1982-09-29 US US06/428,016 patent/US4460773A/en not_active Expired - Fee Related
- 1982-10-07 DE DE19823237243 patent/DE3237243A1/de active Granted
Non-Patent Citations (4)
| Title |
|---|
| C.A. 70, 1969, Ref. 37781 b * |
| C.A. 71, 1969, Ref. 81306 v * |
| C.A. 85, 1976, Ref. 123972 f * |
| C.A. 96, 1982, Ref. 85590 x * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3432983A1 (de) * | 1983-09-07 | 1985-04-18 | Lion Corp., Tokio/Tokyo | 1,5-disubstituierte 1h-pyrazolo(3,4-b)-pyrazin-derivate und antitumormittel, die diese enthalten |
| AP89A (en) * | 1987-08-15 | 1990-06-14 | The Wellcome Foundation Ltd | Heterocyclic compounds. |
Also Published As
| Publication number | Publication date |
|---|---|
| US4460773A (en) | 1984-07-17 |
| DE3237243C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-10-27 |
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| 8364 | No opposition during term of opposition | ||
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