KR20080008399A - 비스(티오-히드라지드 아미드) 염의 합성 방법 - Google Patents
비스(티오-히드라지드 아미드) 염의 합성 방법 Download PDFInfo
- Publication number
- KR20080008399A KR20080008399A KR1020077028282A KR20077028282A KR20080008399A KR 20080008399 A KR20080008399 A KR 20080008399A KR 1020077028282 A KR1020077028282 A KR 1020077028282A KR 20077028282 A KR20077028282 A KR 20077028282A KR 20080008399 A KR20080008399 A KR 20080008399A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- thio
- bis
- hydrazide amide
- organic solvent
- 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.)
- Ceased
Links
- 150000001408 amides Chemical class 0.000 title claims abstract description 84
- 150000003839 salts Chemical class 0.000 title description 10
- 238000001308 synthesis method Methods 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 47
- 239000003960 organic solvent Substances 0.000 claims abstract description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 33
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims abstract description 32
- 230000007935 neutral effect Effects 0.000 claims abstract description 31
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 26
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 21
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 12
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims abstract description 4
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 151
- -1 alkyl glycol ether Chemical compound 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 239000002585 base Substances 0.000 claims description 34
- 125000001931 aliphatic group Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 150000004703 alkoxides Chemical class 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 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 5
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 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 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 3
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- GYBMSOFSBPZKCX-UHFFFAOYSA-N sodium;ethanol;ethanolate Chemical group [Na+].CCO.CC[O-] GYBMSOFSBPZKCX-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- KCMZYCFSSYXEQR-UHFFFAOYSA-N CCCC[K] Chemical compound CCCC[K] KCMZYCFSSYXEQR-UHFFFAOYSA-N 0.000 claims description 2
- IRDQNLLVRXMERV-UHFFFAOYSA-N CCCC[Na] Chemical compound CCCC[Na] IRDQNLLVRXMERV-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- PLOSSHSFATUNTF-UHFFFAOYSA-N [K]C1=CC=CC=C1 Chemical compound [K]C1=CC=CC=C1 PLOSSHSFATUNTF-UHFFFAOYSA-N 0.000 claims description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910000103 lithium hydride Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical group [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims 1
- HYGXISCUUFVGQW-UHFFFAOYSA-N n,n-dimethylformamide;1,4-dioxane Chemical compound CN(C)C=O.C1COCCO1 HYGXISCUUFVGQW-UHFFFAOYSA-N 0.000 claims 1
- 238000001556 precipitation Methods 0.000 abstract description 4
- 238000004108 freeze drying Methods 0.000 abstract description 3
- 238000009472 formulation Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 12
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 11
- 125000001072 heteroaryl group Chemical group 0.000 description 11
- 239000002002 slurry Substances 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 230000001093 anti-cancer Effects 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 239000013557 residual solvent Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229940123237 Taxane Drugs 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical class [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- XVEPGUUOVVKXRA-UHFFFAOYSA-N CC1(CC1)C(N(C)NC(CC(NN(C)C(C1(C)CC1)=S)=O)=O)=S Chemical compound CC1(CC1)C(N(C)NC(CC(NN(C)C(C1(C)CC1)=S)=O)=O)=S XVEPGUUOVVKXRA-UHFFFAOYSA-N 0.000 description 1
- MGJBERWKPZUCJM-UHFFFAOYSA-N CN(C(C1CC1)=S)NC(CC(NN(C)C(C1CC1)=S)=O)=O Chemical compound CN(C(C1CC1)=S)NC(CC(NN(C)C(C1CC1)=S)=O)=O MGJBERWKPZUCJM-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 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 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/56—Amides of thiocarboxylic acids having nitrogen atoms of thiocarboxamide groups further bound to another hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68126305P | 2005-05-16 | 2005-05-16 | |
| US60/681,263 | 2005-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080008399A true KR20080008399A (ko) | 2008-01-23 |
Family
ID=37057197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020077028282A Ceased KR20080008399A (ko) | 2005-05-16 | 2006-05-11 | 비스(티오-히드라지드 아미드) 염의 합성 방법 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7709683B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1888520A2 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2008540658A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20080008399A (cg-RX-API-DMAC7.html) |
| CN (1) | CN101223133B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2006247470B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0611262A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2607890A1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL187056A (cg-RX-API-DMAC7.html) |
| MX (1) | MX2007014314A (cg-RX-API-DMAC7.html) |
| NO (1) | NO20075707L (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ563124A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2407734C2 (cg-RX-API-DMAC7.html) |
| TW (1) | TWI387579B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2006124736A2 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA200709395B (cg-RX-API-DMAC7.html) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI252847B (en) * | 2001-07-10 | 2006-04-11 | Synta Pharmaceuticals Corp | Synthesis of taxol enhancers |
| TWI297335B (en) | 2001-07-10 | 2008-06-01 | Synta Pharmaceuticals Corp | Taxol enhancer compounds |
| TWI332943B (en) * | 2001-07-10 | 2010-11-11 | Synta Pharmaceuticals Corp | Taxol enhancer compounds |
| TWI330079B (en) | 2003-01-15 | 2010-09-11 | Synta Pharmaceuticals Corp | Treatment for cancers |
| ES2430373T3 (es) * | 2004-06-23 | 2013-11-20 | Synta Pharmaceuticals Corp. | Sales de bis(tio-hidrazida amida) para tratamiento de cánceres |
| CA2587598A1 (en) * | 2004-11-19 | 2006-05-26 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amides) for increasing hsp70 expression |
| EP1877048A1 (en) | 2005-04-15 | 2008-01-16 | Synta Pharmaceuticals Corporation | Combination cancer therapy with bis(thiohydrazide) amide compounds |
| CA2603314A1 (en) * | 2005-04-15 | 2006-10-26 | Synta Pharmaceuticals Corp. | Methods of increasing natural killer cell activity for therapy |
| AU2006279891B2 (en) * | 2005-08-16 | 2010-03-11 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amide) formulation |
| AU2007288338B2 (en) | 2006-08-21 | 2012-05-03 | Synta Pharmaceuticals Corp. | Compounds for treating proliferative disorders |
| JP2010501558A (ja) * | 2006-08-21 | 2010-01-21 | シンタ ファーマシューティカルズ コーポレーション | 癌を治療するためのビス（チオヒドラジドアミド）との組み合わせ |
| EP2063878A2 (en) * | 2006-08-21 | 2009-06-03 | Synta Pharmaceuticals Corporation | Bis(thiohydrazide amides) for use in preventing or delaying the recurrence of melanoma |
| WO2008024305A2 (en) * | 2006-08-21 | 2008-02-28 | Synta Pharmaceuticals Corp. | Bis (thiohydrazide amides) for treating melanoma |
| WO2008027445A2 (en) * | 2006-08-31 | 2008-03-06 | Synta Pharmaceuticals Corp. | Combination with bis(thiohydrazide amides) for treating cancer |
| US9498528B2 (en) * | 2006-09-13 | 2016-11-22 | Genzyme Corporation | Treatment of multiple sclerosis (MS) |
| WO2008033494A2 (en) | 2006-09-15 | 2008-03-20 | Synta Pharmaceuticals Corp. | Purification of bis(thiohydrazide amides) |
| WO2009064374A2 (en) | 2007-11-09 | 2009-05-22 | Synta Pharmaceuticals Corp. | Oral formulations of bis(thiohydrazide amides) |
| US8581004B2 (en) | 2008-02-21 | 2013-11-12 | Synta Pharmaceuticals Corp. | Compounds for treating proliferative disorders |
| WO2009123704A2 (en) * | 2008-03-31 | 2009-10-08 | Synta Pharmaceuticals Corp. | Process for preparing bis(thiohydrazide amides) |
| KR20110081300A (ko) | 2008-10-22 | 2011-07-13 | 신타 파마슈티칼스 코프. | 비스[티오하이드라자이드 아미드] 화합물의 전이금속 복합물 |
| US9174935B2 (en) | 2008-10-22 | 2015-11-03 | Synta Pharmaceuticals Corp. | Transition metal complexes of bis[thiohydrazide amide] compounds |
| US8525776B2 (en) * | 2008-10-27 | 2013-09-03 | Lenovo (Singapore) Pte. Ltd | Techniques for controlling operation of a device with a virtual touchscreen |
| US8680100B2 (en) | 2008-12-01 | 2014-03-25 | Synta Pharmaceuticals Corp. | Sulfonylhydrazide compounds for treating proliferative disorders |
| WO2011069159A2 (en) | 2009-12-04 | 2011-06-09 | Synta Pharmaceuticals Corp. | Bis[thiohydrazide amide] compounds for treating leukemia |
| EP2560627A1 (en) | 2010-04-20 | 2013-02-27 | Synta Pharmaceuticals Corp. | Use of bis [thiohydrazide amide]compounds such as elesclomol for treating cancers |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2097737A5 (en) | 1970-07-14 | 1972-03-03 | Berlin Chemie Veb | Virustatic 4-substd 1-acylthiosemicarbazides -from carboxylic acid - hydrazide and isothiocyanates or from carboxylic acid chloride and 4- |
| DE2037257A1 (en) | 1970-07-28 | 1972-02-03 | Farbwerke Hoechst AG, vorm. Meister Lucius & Brüning, 6000 Frankfurt | Poly-(5-amino-1,3,4-thiadiazol-2-yl) derivs prepn - intermediates for drug and polymer prodn |
| US4012360A (en) | 1973-12-03 | 1977-03-15 | Ciba-Geigy Corporation | Bis-salicyloyl-dicarboxylic acid dihydrazides as stabilizers for polyolefines |
| JPS5091056A (cg-RX-API-DMAC7.html) | 1973-12-17 | 1975-07-21 | ||
| US6013836A (en) | 1992-02-28 | 2000-01-11 | Rohm And Haas Company | Insecticidal N'-substituted-N,N'-disubstitutedhydrazines |
| FR2697752B1 (fr) | 1992-11-10 | 1995-04-14 | Rhone Poulenc Rorer Sa | Compositions antitumorales contenant des dérivés du taxane. |
| EP0851874B1 (en) | 1995-09-22 | 1999-09-15 | Novo Nordisk A/S | Novel variants of green fluorescent protein, gfp |
| US6235787B1 (en) | 1997-06-30 | 2001-05-22 | Hoffmann-La Roche Inc. | Hydrazine derivatives |
| GB9727524D0 (en) | 1997-12-31 | 1998-02-25 | Pharmacia & Upjohn Spa | Synergistic antitumor composition containing a biologically active ureido compound |
| TW479053B (en) | 1998-10-19 | 2002-03-11 | Agro Kanesho Co Ltd | Hydrazineoxoacetamide derivatives and pesticides |
| ES2161594B1 (es) | 1998-12-17 | 2003-04-01 | Servier Lab | Nuevos derivados de la hidrazida, su procedimiento de preparacion y las composiciones farmaceuticas que los contienen. |
| US6322303B1 (en) | 2000-05-12 | 2001-11-27 | David M. John | Dunnage bag and method of making same |
| EP1164126A1 (de) | 2000-06-16 | 2001-12-19 | Basf Aktiengesellschaft | Salicylsäurehydrazid-Derivate, Verfahren und Zwischenprodukte zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung zur Bekämpfung von Schadpilzen |
| US6365745B1 (en) | 2000-07-14 | 2002-04-02 | Sumika Fine Chemicals Co., Ltd. | Method for producing hydrazine derivative |
| EP1360173A2 (en) | 2001-01-25 | 2003-11-12 | Guilford Pharmaceuticals Inc. | Trisubstituted carbocyclic cyclophilin binding compounds and their use |
| US6602907B1 (en) | 2001-06-08 | 2003-08-05 | University Of Central Florida | Treatment of breast cancer |
| TWI252847B (en) * | 2001-07-10 | 2006-04-11 | Synta Pharmaceuticals Corp | Synthesis of taxol enhancers |
| TWI297335B (en) * | 2001-07-10 | 2008-06-01 | Synta Pharmaceuticals Corp | Taxol enhancer compounds |
| TWI332943B (en) * | 2001-07-10 | 2010-11-11 | Synta Pharmaceuticals Corp | Taxol enhancer compounds |
| US6924312B2 (en) * | 2001-07-10 | 2005-08-02 | Synta Pharmaceuticals Corp. | Taxol enhancer compounds |
| TW200408407A (en) * | 2001-11-30 | 2004-06-01 | Dana Farber Cancer Inst Inc | Methods and compositions for modulating the immune system and uses thereof |
| TWI330079B (en) | 2003-01-15 | 2010-09-11 | Synta Pharmaceuticals Corp | Treatment for cancers |
| ES2430373T3 (es) * | 2004-06-23 | 2013-11-20 | Synta Pharmaceuticals Corp. | Sales de bis(tio-hidrazida amida) para tratamiento de cánceres |
| WO2006033913A2 (en) | 2004-09-16 | 2006-03-30 | Synta Pharmaceuticals Corp. | Bis (thio-hydrazide amides) for treament of hyperplasia |
| CA2587598A1 (en) * | 2004-11-19 | 2006-05-26 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amides) for increasing hsp70 expression |
| EP1877048A1 (en) | 2005-04-15 | 2008-01-16 | Synta Pharmaceuticals Corporation | Combination cancer therapy with bis(thiohydrazide) amide compounds |
| CA2603314A1 (en) | 2005-04-15 | 2006-10-26 | Synta Pharmaceuticals Corp. | Methods of increasing natural killer cell activity for therapy |
| WO2006113493A2 (en) | 2005-04-15 | 2006-10-26 | Synta Pharmaceuticals Corp. | Methods of determining cancer prognosis via natural killer cell activity |
| AU2006279891B2 (en) * | 2005-08-16 | 2010-03-11 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amide) formulation |
-
2006
- 2006-05-11 MX MX2007014314A patent/MX2007014314A/es active IP Right Grant
- 2006-05-11 NZ NZ563124A patent/NZ563124A/en not_active IP Right Cessation
- 2006-05-11 US US11/432,307 patent/US7709683B2/en not_active Expired - Fee Related
- 2006-05-11 CN CN2006800170928A patent/CN101223133B/zh not_active Expired - Fee Related
- 2006-05-11 JP JP2008512390A patent/JP2008540658A/ja active Pending
- 2006-05-11 WO PCT/US2006/018653 patent/WO2006124736A2/en not_active Ceased
- 2006-05-11 CA CA002607890A patent/CA2607890A1/en not_active Abandoned
- 2006-05-11 BR BRPI0611262-5A patent/BRPI0611262A2/pt not_active IP Right Cessation
- 2006-05-11 KR KR1020077028282A patent/KR20080008399A/ko not_active Ceased
- 2006-05-11 AU AU2006247470A patent/AU2006247470B2/en not_active Ceased
- 2006-05-11 RU RU2007144216/04A patent/RU2407734C2/ru not_active IP Right Cessation
- 2006-05-11 EP EP06770334A patent/EP1888520A2/en not_active Withdrawn
- 2006-05-12 TW TW095116857A patent/TWI387579B/zh not_active IP Right Cessation
-
2007
- 2007-10-31 IL IL187056A patent/IL187056A/en not_active IP Right Cessation
- 2007-10-31 ZA ZA200709395A patent/ZA200709395B/xx unknown
- 2007-11-08 NO NO20075707A patent/NO20075707L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200709395B (en) | 2008-10-29 |
| WO2006124736A3 (en) | 2007-03-29 |
| AU2006247470B2 (en) | 2010-04-01 |
| CN101223133B (zh) | 2012-02-29 |
| MX2007014314A (es) | 2008-02-11 |
| CA2607890A1 (en) | 2006-11-23 |
| TWI387579B (zh) | 2013-03-01 |
| TW200722411A (en) | 2007-06-16 |
| US20060270873A1 (en) | 2006-11-30 |
| NZ563124A (en) | 2010-12-24 |
| RU2407734C2 (ru) | 2010-12-27 |
| JP2008540658A (ja) | 2008-11-20 |
| US7709683B2 (en) | 2010-05-04 |
| IL187056A0 (en) | 2008-02-09 |
| WO2006124736A2 (en) | 2006-11-23 |
| RU2007144216A (ru) | 2009-06-27 |
| AU2006247470A1 (en) | 2006-11-23 |
| NO20075707L (no) | 2007-12-11 |
| CN101223133A (zh) | 2008-07-16 |
| IL187056A (en) | 2013-10-31 |
| EP1888520A2 (en) | 2008-02-20 |
| BRPI0611262A2 (pt) | 2010-08-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20080008399A (ko) | 비스(티오-히드라지드 아미드) 염의 합성 방법 | |
| ES2655899T3 (es) | Compuestos de pirazolo[1,5-a]pirimidina sustituidos como inhibidores de la Trk cinasa | |
| RU2007101898A (ru) | Соли бис (тиогидразидамида) для лечения рака | |
| US11771712B2 (en) | Carborane compounds and methods of use thereof | |
| JP2008504264A5 (cg-RX-API-DMAC7.html) | ||
| EP2208721A1 (en) | Histone deacetylase inhibitor, composition and use thereof | |
| JP2008540658A5 (cg-RX-API-DMAC7.html) | ||
| TW202440561A (zh) | 四氫噻吩衍生物及其在醫藥上的應用 | |
| WO2009073147A2 (en) | Process for preparing bis(thiohydrazide amides) | |
| ES2373866T3 (es) | Procedimiento para la producción de derivados de 3,6-dihidro-1,3,5-triazina. | |
| AP694A (en) | Nitro-benzamides useful as anti-arrhythmic agents. | |
| US20220040210A1 (en) | Carborane compounds, carborane analogs, and methods of use thereof | |
| US8871983B2 (en) | Lipid compounds for suppression of tumorigenesis | |
| ES2432525T3 (es) | Pirroles sustituidos terapéuticos | |
| EP3897592B1 (en) | Compounds for the inhibition of unregulated cell growth | |
| RU2403238C2 (ru) | Способ получения сульфамат-карбоксилатных производных | |
| RU2012136831A (ru) | Синтез замещенных производных пиразолин карбоксамидина | |
| US20250188098A1 (en) | Carborane compounds and methods of use thereof | |
| HK1261921B (en) | Carborane compounds and methods of use thereof | |
| HK1261921A1 (en) | Carborane compounds and methods of use thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20071204 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20110511 Comment text: Request for Examination of Application |
|
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20121217 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20130521 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20121217 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |