KR20150040845A - 치환된 트리아졸로피리딘을 제조하는 방법 - Google Patents
치환된 트리아졸로피리딘을 제조하는 방법 Download PDFInfo
- Publication number
- KR20150040845A KR20150040845A KR20157000338A KR20157000338A KR20150040845A KR 20150040845 A KR20150040845 A KR 20150040845A KR 20157000338 A KR20157000338 A KR 20157000338A KR 20157000338 A KR20157000338 A KR 20157000338A KR 20150040845 A KR20150040845 A KR 20150040845A
- Authority
- KR
- South Korea
- Prior art keywords
- amino
- pyridin
- phenyl
- triazolo
- fluorophenyl
- 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.)
- Withdrawn
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- 238000000034 method Methods 0.000 title claims abstract description 102
- 150000008523 triazolopyridines Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 328
- 238000002360 preparation method Methods 0.000 claims abstract description 64
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 454
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 343
- -1 hydroxy- Chemical class 0.000 claims description 320
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 164
- 125000005843 halogen group Chemical group 0.000 claims description 137
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 130
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 103
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 68
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 52
- 239000007787 solid Substances 0.000 claims description 51
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 48
- 150000001412 amines Chemical class 0.000 claims description 31
- 238000005859 coupling reaction Methods 0.000 claims description 31
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 27
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 24
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 23
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 20
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 15
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 claims description 15
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 12
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
- 125000001475 halogen functional group Chemical group 0.000 claims description 9
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- DACWQSNZECJJGG-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CN=C21 DACWQSNZECJJGG-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 6
- NRJKIOCCERLIDG-GOSISDBHSA-N (2r)-2-(4-fluorophenyl)-n-[4-[2-(2-methoxy-4-methylsulfonylanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]propanamide Chemical compound COC1=CC(S(C)(=O)=O)=CC=C1NC1=NN2C=C(C=3C=CC(NC(=O)[C@H](C)C=4C=CC(F)=CC=4)=CC=3)C=CC2=N1 NRJKIOCCERLIDG-GOSISDBHSA-N 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 125000004175 fluorobenzyl group Chemical group 0.000 claims description 4
- VYJXPBPEYOOMNE-GOSISDBHSA-N (2r)-2-(4-fluorophenyl)-n-[4-[2-[4-methylsulfonyl-2-(2,2,2-trifluoroethoxy)anilino]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]propanamide Chemical compound O=C([C@H](C)C=1C=CC(F)=CC=1)NC(C=C1)=CC=C1C(=CN1N=2)C=CC1=NC=2NC1=CC=C(S(C)(=O)=O)C=C1OCC(F)(F)F VYJXPBPEYOOMNE-GOSISDBHSA-N 0.000 claims description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- RHGJKFDRWARLHZ-UHFFFAOYSA-N 2-(2-fluoroethyl)-3-methoxybenzamide Chemical compound FCCC1=C(C(=O)N)C=CC=C1OC RHGJKFDRWARLHZ-UHFFFAOYSA-N 0.000 claims description 2
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 2
- ZBWYZLANPMFDMN-UHFFFAOYSA-N 2-methoxy-n,n-dimethylbenzamide Chemical compound COC1=CC=CC=C1C(=O)N(C)C ZBWYZLANPMFDMN-UHFFFAOYSA-N 0.000 claims description 2
- NXVAEVHJWOBXKG-UHFFFAOYSA-N 2-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1OC NXVAEVHJWOBXKG-UHFFFAOYSA-N 0.000 claims description 2
- MNWSGMTUGXNYHJ-UHFFFAOYSA-N 2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(N)=O MNWSGMTUGXNYHJ-UHFFFAOYSA-N 0.000 claims description 2
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims description 2
- GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 claims description 2
- QUCMDRRSMMPTSK-UHFFFAOYSA-N N-[(4-fluorophenyl)methyl]-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)benzamide Chemical compound FC1=CC=C(CNC(=O)C2=CC=C(C=C2)C=2C=CC=3N(C2)N=CN3)C=C1 QUCMDRRSMMPTSK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims 2
- HUPVBFQYJHFONM-UHFFFAOYSA-N 2-(4-fluorophenyl)acetamide Chemical compound NC(=O)CC1=CC=C(F)C=C1 HUPVBFQYJHFONM-UHFFFAOYSA-N 0.000 claims 2
- 239000000543 intermediate Substances 0.000 abstract description 126
- 239000000203 mixture Substances 0.000 description 224
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 162
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 155
- 239000000243 solution Substances 0.000 description 133
- 239000002904 solvent Substances 0.000 description 125
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 84
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 77
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 76
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- 238000010898 silica gel chromatography Methods 0.000 description 54
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 50
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 48
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 46
- 229910052938 sodium sulfate Inorganic materials 0.000 description 46
- 235000011152 sodium sulphate Nutrition 0.000 description 46
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- 239000012074 organic phase Substances 0.000 description 45
- 210000004027 cell Anatomy 0.000 description 44
- 239000000725 suspension Substances 0.000 description 42
- 230000015572 biosynthetic process Effects 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 38
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 37
- 238000003786 synthesis reaction Methods 0.000 description 36
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 32
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 31
- 235000017557 sodium bicarbonate Nutrition 0.000 description 31
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 30
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 30
- 238000010992 reflux Methods 0.000 description 28
- 238000004519 manufacturing process Methods 0.000 description 27
- 239000012047 saturated solution Substances 0.000 description 27
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 27
- 125000004432 carbon atom Chemical group C* 0.000 description 26
- 108091000080 Phosphotransferase Proteins 0.000 description 25
- 229910052786 argon Inorganic materials 0.000 description 25
- 102000020233 phosphotransferase Human genes 0.000 description 25
- 239000002585 base Substances 0.000 description 24
- 229910000027 potassium carbonate Inorganic materials 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- 239000007821 HATU Substances 0.000 description 21
- 230000008569 process Effects 0.000 description 21
- 125000006239 protecting group Chemical group 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
- 230000014759 maintenance of location Effects 0.000 description 20
- 238000000746 purification Methods 0.000 description 20
- 239000011877 solvent mixture Substances 0.000 description 19
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
- 238000003556 assay Methods 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- 229960001866 silicon dioxide Drugs 0.000 description 17
- 0 *C(*)C(N)=O Chemical compound *C(*)C(N)=O 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 15
- QRXMUCSWCMTJGU-UHFFFAOYSA-N 5-bromo-4-chloro-3-indolyl phosphate Chemical compound C1=C(Br)C(Cl)=C2C(OP(O)(=O)O)=CNC2=C1 QRXMUCSWCMTJGU-UHFFFAOYSA-N 0.000 description 15
- 235000019253 formic acid Nutrition 0.000 description 15
- 229910000160 potassium phosphate Inorganic materials 0.000 description 15
- 235000011009 potassium phosphates Nutrition 0.000 description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- 239000003153 chemical reaction reagent Substances 0.000 description 14
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- IXSCGBODJGIJNN-ZCFIWIBFSA-N (2r)-2-(4-fluorophenyl)propanoic acid Chemical compound OC(=O)[C@H](C)C1=CC=C(F)C=C1 IXSCGBODJGIJNN-ZCFIWIBFSA-N 0.000 description 11
- 206010028980 Neoplasm Diseases 0.000 description 11
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- ZKHQWZAMYRWXGA-KQYNXXCUSA-N Adenosine triphosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-N 0.000 description 10
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 10
- 230000008878 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 10
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 230000000394 mitotic effect Effects 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 101150003085 Pdcl gene Proteins 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- 239000012317 TBTU Substances 0.000 description 8
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 8
- 150000001408 amides Chemical group 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
- 239000012442 inert solvent Substances 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 108090000765 processed proteins & peptides Proteins 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 102100033636 Histone H3.2 Human genes 0.000 description 7
- 108010033040 Histones Proteins 0.000 description 7
- 125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 description 7
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 7
- 230000004663 cell proliferation Effects 0.000 description 7
- 238000001514 detection method Methods 0.000 description 7
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 230000011278 mitosis Effects 0.000 description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
- 239000002953 phosphate buffered saline Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- UEVXVBKBOFGKIN-UHFFFAOYSA-N 4-bromo-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1Br UEVXVBKBOFGKIN-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- 230000009038 pharmacological inhibition Effects 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 201000001514 prostate carcinoma Diseases 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 235000008160 pyridoxine Nutrition 0.000 description 1
- 239000011677 pyridoxine Substances 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- YOWAEZWWQFSEJD-UHFFFAOYSA-N quinoxalin-2-amine Chemical class C1=CC=CC2=NC(N)=CN=C21 YOWAEZWWQFSEJD-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 230000035945 sensitivity Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 201000004477 skin sarcoma Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000019130 spindle checkpoint Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- HNUHNECIEYXPJH-UHFFFAOYSA-N tert-butyl n-[4-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C1=CN2N=C(N)N=C2C=C1 HNUHNECIEYXPJH-UHFFFAOYSA-N 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
- 125000005455 trithianyl group Chemical group 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 208000024719 uterine cervix neoplasm Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12175640.7 | 2012-07-10 | ||
| EP12175640 | 2012-07-10 | ||
| EP12185590 | 2012-09-24 | ||
| EP12185590.2 | 2012-09-24 | ||
| EP13170585.7 | 2013-06-05 | ||
| EP13170585 | 2013-06-05 | ||
| PCT/EP2013/064017 WO2014009219A1 (en) | 2012-07-10 | 2013-07-03 | Method for preparing substituted triazolopyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150040845A true KR20150040845A (ko) | 2015-04-15 |
Family
ID=48793197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR20157000338A Withdrawn KR20150040845A (ko) | 2012-07-10 | 2013-07-03 | 치환된 트리아졸로피리딘을 제조하는 방법 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US9388177B2 (https=) |
| EP (1) | EP2872506A1 (https=) |
| JP (1) | JP6238979B2 (https=) |
| KR (1) | KR20150040845A (https=) |
| CN (1) | CN104603136B (https=) |
| AP (1) | AP3778A (https=) |
| AU (1) | AU2013289381A1 (https=) |
| BR (1) | BR112015000308A2 (https=) |
| CA (1) | CA2878481A1 (https=) |
| CL (1) | CL2015000038A1 (https=) |
| CO (1) | CO7160002A2 (https=) |
| CR (1) | CR20150006A (https=) |
| DO (1) | DOP2015000007A (https=) |
| EA (1) | EA027544B1 (https=) |
| HK (1) | HK1206731A1 (https=) |
| IL (1) | IL236265A (https=) |
| IN (1) | IN2015DN00085A (https=) |
| MX (1) | MX2015000348A (https=) |
| NZ (1) | NZ703020A (https=) |
| PE (1) | PE20150354A1 (https=) |
| PH (1) | PH12015500061A1 (https=) |
| SG (1) | SG11201408419QA (https=) |
| TN (1) | TN2015000008A1 (https=) |
| WO (1) | WO2014009219A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HK1222849A1 (zh) * | 2013-06-07 | 2017-07-14 | Bayer Pharma Aktiengesellschaft | 具有作爲mps-1抑制剂的活性的取代的三唑并吡啶类 |
| TN2015000543A1 (en) | 2013-06-11 | 2017-04-06 | Bayer Pharma AG | Combinations for the treatment of cancer comprising a mps-1 kinase inhibitor and a mitotic inhibitor |
| AP2015008898A0 (en) * | 2013-06-11 | 2015-12-31 | Bayer Pharma AG | Prodrug derivatives of substituted triazolopyridines |
| ES2966392T3 (es) | 2015-04-17 | 2024-04-22 | Crossfire Oncology Holding B V | Biomarcadores pronósticos para quimioterapia inhibidora de TTK |
| TW201800408A (zh) | 2016-06-15 | 2018-01-01 | 拜耳製藥公司 | Mps-1抑制劑 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003030937A1 (en) * | 2001-10-05 | 2003-04-17 | Ono Pharmaceutical Co., Ltd. | Remedies for stress diseases comprising mitochondrial benzodiazepine receptor antagonists |
| WO2005110410A2 (en) * | 2004-05-14 | 2005-11-24 | Abbott Laboratories | Kinase inhibitors as therapeutic agents |
| UA89503C2 (uk) * | 2004-09-13 | 2010-02-10 | Х. Луннбек А/С | Заміщені похідні аніліну |
| EP1799680A2 (en) * | 2004-10-07 | 2007-06-27 | Warner-Lambert Company LLC | Triazolopyridine derivatives as antibacterial agents |
| US20060194823A1 (en) * | 2004-12-22 | 2006-08-31 | Georg Kettschau | Sulfonamido-macrocycles as Tie2 inhibitors and the salts thereof, a pharmaceutical composition comprising these compounds, the method of preparing and the use thereof |
| EP2029605A1 (en) * | 2006-06-06 | 2009-03-04 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| EP1870416A1 (en) * | 2006-06-21 | 2007-12-26 | Bayer Schering Pharma Aktiengesellschaft | Sulphonamido-macrocycles as tie2 inhibitors |
| BRPI0716239A2 (pt) | 2006-08-30 | 2013-08-13 | Cellzome Ltd | derivados de triazol como inibidores de cinase |
| JO3598B1 (ar) * | 2006-10-10 | 2020-07-05 | Infinity Discovery Inc | الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني |
| CA2693232A1 (en) | 2007-07-18 | 2009-01-22 | Novartis Ag | Bicyclic heteroaryl compounds and their use as kinase inhibitors |
| MX2010002115A (es) | 2007-08-23 | 2010-06-01 | Aztrazeneca Ab | 2-anilinopurin-8-onas como inhibidores de ttk/mps1 para el tratamiento de trastornos .proliferativos. |
| CA2691448A1 (en) | 2007-08-31 | 2009-03-05 | Dominique Swinnen | Triazolopyridine compounds and their use as ask inhibitors |
| GB0719803D0 (en) | 2007-10-10 | 2007-11-21 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| GB0724342D0 (en) * | 2007-12-13 | 2008-01-30 | Prolysis Ltd | Anitbacterial compositions |
| WO2009137322A2 (en) * | 2008-05-05 | 2009-11-12 | The Trustees Of The University Of Pennsylvania | Processes for the preparation of biphenyl compounds |
| US20110212053A1 (en) * | 2008-06-19 | 2011-09-01 | Dapeng Qian | Phosphatidylinositol 3 kinase inhibitors |
| SG173610A1 (en) | 2009-02-13 | 2011-09-29 | Fovea Pharmaceuticals Sa | [1, 2, 4] triazolo [1, 5 -a] pyridines as kinase inhibitors |
| JP6168773B2 (ja) | 2009-04-29 | 2017-07-26 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換イミダゾキノキサリン |
| EP2438066A2 (en) * | 2009-06-05 | 2012-04-11 | Cephalon, Inc. | PREPARATION AND USES OF 1,2,4-TRIAZOLO [1,5a]PYRIDINE DERIVATIVES |
| WO2010141360A1 (en) * | 2009-06-05 | 2010-12-09 | Merck Sharp & Dohme Corp. | Biaryl benzotriazole derivatives |
| JP5728683B2 (ja) | 2009-09-04 | 2015-06-03 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | チロシンスレオニンキナーゼ阻害剤としての置換アミノキノキサリン |
| EP2343294A1 (en) * | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Substituted triazolopyridines |
| EP2343295A1 (en) * | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridine derivates |
| EP2343297A1 (en) * | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridines |
| UY33452A (es) * | 2010-06-16 | 2012-01-31 | Bayer Schering Pharma Ag | Triazolopiridinas sustituidas |
| WO2012044567A2 (en) * | 2010-09-30 | 2012-04-05 | Merck Sharp & Dohme Corp. | Imidazole derivatives |
| RS54044B1 (sr) | 2011-04-21 | 2015-10-30 | Bayer Intellectual Property Gmbh | Triazolopiridini |
| WO2012160029A1 (en) * | 2011-05-23 | 2012-11-29 | Bayer Intellectual Property Gmbh | Substituted triazolopyridines |
| UA112096C2 (uk) * | 2011-12-12 | 2016-07-25 | Байєр Інтеллектуал Проперті Гмбх | Заміщені триазолопіридини та їх застосування як інгібіторів ttk |
-
2013
- 2013-07-03 SG SG11201408419QA patent/SG11201408419QA/en unknown
- 2013-07-03 US US14/414,164 patent/US9388177B2/en not_active Expired - Fee Related
- 2013-07-03 WO PCT/EP2013/064017 patent/WO2014009219A1/en not_active Ceased
- 2013-07-03 KR KR20157000338A patent/KR20150040845A/ko not_active Withdrawn
- 2013-07-03 IN IN85DEN2015 patent/IN2015DN00085A/en unknown
- 2013-07-03 EA EA201590116A patent/EA027544B1/ru not_active IP Right Cessation
- 2013-07-03 MX MX2015000348A patent/MX2015000348A/es unknown
- 2013-07-03 PE PE2015000017A patent/PE20150354A1/es not_active Application Discontinuation
- 2013-07-03 EP EP13737181.1A patent/EP2872506A1/en not_active Withdrawn
- 2013-07-03 HK HK15107242.4A patent/HK1206731A1/xx unknown
- 2013-07-03 CA CA2878481A patent/CA2878481A1/en not_active Abandoned
- 2013-07-03 JP JP2015520907A patent/JP6238979B2/ja not_active Expired - Fee Related
- 2013-07-03 CN CN201380045913.9A patent/CN104603136B/zh not_active Expired - Fee Related
- 2013-07-03 BR BR112015000308A patent/BR112015000308A2/pt not_active IP Right Cessation
- 2013-07-03 AU AU2013289381A patent/AU2013289381A1/en not_active Abandoned
- 2013-07-03 NZ NZ703020A patent/NZ703020A/en not_active IP Right Cessation
- 2013-07-03 AP AP2014008177A patent/AP3778A/en active
-
2014
- 2014-12-15 IL IL236265A patent/IL236265A/en not_active IP Right Cessation
-
2015
- 2015-01-07 TN TNP2015000008A patent/TN2015000008A1/fr unknown
- 2015-01-08 CL CL2015000038A patent/CL2015000038A1/es unknown
- 2015-01-09 PH PH12015500061A patent/PH12015500061A1/en unknown
- 2015-01-09 CO CO15004251A patent/CO7160002A2/es unknown
- 2015-01-09 DO DO2015000007A patent/DOP2015000007A/es unknown
- 2015-01-09 CR CR20150006A patent/CR20150006A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN2015DN00085A (https=) | 2015-05-29 |
| PE20150354A1 (es) | 2015-03-21 |
| US20150148542A1 (en) | 2015-05-28 |
| HK1206731A1 (en) | 2016-01-15 |
| JP6238979B2 (ja) | 2017-11-29 |
| SG11201408419QA (en) | 2015-01-29 |
| AU2013289381A1 (en) | 2015-01-22 |
| TN2015000008A1 (en) | 2016-06-29 |
| IL236265A0 (en) | 2015-02-26 |
| DOP2015000007A (es) | 2015-02-15 |
| BR112015000308A2 (pt) | 2017-06-27 |
| EA201590116A1 (ru) | 2015-07-30 |
| AP2014008177A0 (en) | 2014-12-31 |
| US9388177B2 (en) | 2016-07-12 |
| EP2872506A1 (en) | 2015-05-20 |
| JP2015523372A (ja) | 2015-08-13 |
| CN104603136A (zh) | 2015-05-06 |
| IL236265A (en) | 2017-07-31 |
| CA2878481A1 (en) | 2014-01-16 |
| MX2015000348A (es) | 2015-04-14 |
| CO7160002A2 (es) | 2015-01-15 |
| CR20150006A (es) | 2015-02-16 |
| EA027544B1 (ru) | 2017-08-31 |
| CL2015000038A1 (es) | 2015-03-13 |
| CN104603136B (zh) | 2017-06-27 |
| AP3778A (en) | 2016-08-31 |
| WO2014009219A1 (en) | 2014-01-16 |
| PH12015500061A1 (en) | 2015-03-02 |
| NZ703020A (en) | 2017-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20150107 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |