JP2003502317A5 - - Google Patents
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- Publication number
- JP2003502317A5 JP2003502317A5 JP2001503842A JP2001503842A JP2003502317A5 JP 2003502317 A5 JP2003502317 A5 JP 2003502317A5 JP 2001503842 A JP2001503842 A JP 2001503842A JP 2001503842 A JP2001503842 A JP 2001503842A JP 2003502317 A5 JP2003502317 A5 JP 2003502317A5
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- piperazinyl
- pyrazinyl
- ethyl
- pyrazine
- 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
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 23
- 229910052739 hydrogen Inorganic materials 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000012458 free base Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- FAMRKDQNMBBFBR-BQYQJAHWSA-N Diethyl azodicarboxylate Chemical compound CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- -1 2- (3,5-dimethoxyphenoxy) ethyl 3- (1-piperazinyl) -2-pyrazinyl ether 2- (3,4-dihydro-2H-pyrido [3,2-b] -1,4-oxazine- 2-ylmethoxy) -3- (1-piperazinyl) pyrazine Chemical compound 0.000 description 7
- LKYXEULZVGJVTG-UHFFFAOYSA-N chloromethane Chemical group Cl[CH] LKYXEULZVGJVTG-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 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 4
- 238000000605 extraction Methods 0.000 description 4
- 125000005842 heteroatoms Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- RTIIHAFMXNGVIX-UHFFFAOYSA-N 2-chloro-3-(2-phenoxyethoxy)pyrazine Chemical compound ClC1=NC=CN=C1OCCOC1=CC=CC=C1 RTIIHAFMXNGVIX-UHFFFAOYSA-N 0.000 description 3
- YSEFEUMYRXRNND-UHFFFAOYSA-N 2-chloro-3-piperazin-1-ylpyrazine Chemical compound ClC1=NC=CN=C1N1CCNCC1 YSEFEUMYRXRNND-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atoms Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- KDLVSGWUKFJFTL-UHFFFAOYSA-N 3,4-dihydro-2H-chromen-2-ylmethanol Chemical compound C1=CC=C2OC(CO)CCC2=C1 KDLVSGWUKFJFTL-UHFFFAOYSA-N 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N Potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- IJINSJSWDSHUBL-UHFFFAOYSA-N tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=NC=CN=C1Cl IJINSJSWDSHUBL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- VLSDXINSOMDCBK-BQYQJAHWSA-N (E)-1,1'-azobis(N,N-dimethylformamide) Chemical compound CN(C)C(=O)\N=N\C(=O)N(C)C VLSDXINSOMDCBK-BQYQJAHWSA-N 0.000 description 1
- WWPWWAHQDTYCPM-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-ylmethanol Chemical group C1=CC=C2CC(CO)CCC2=C1 WWPWWAHQDTYCPM-UHFFFAOYSA-N 0.000 description 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
- ZCEJWOSDIWQJJR-UHFFFAOYSA-N 1-[3-(2,3-dihydro-1,4-benzodioxin-3-ylmethoxy)pyrazin-2-yl]-1,4-diazepane Chemical compound C1OC2=CC=CC=C2OC1COC1=NC=CN=C1N1CCCNCC1 ZCEJWOSDIWQJJR-UHFFFAOYSA-N 0.000 description 1
- QRMYHUSKXOHTEN-UHFFFAOYSA-N 1-[3-(2-phenoxyethoxy)pyrazin-2-yl]pyrrolidin-3-amine Chemical compound C1C(N)CCN1C1=NC=CN=C1OCCOC1=CC=CC=C1 QRMYHUSKXOHTEN-UHFFFAOYSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- MLCNOCRGSBCAGH-UHFFFAOYSA-N 2,3-dichloropyrazine Chemical compound ClC1=NC=CN=C1Cl MLCNOCRGSBCAGH-UHFFFAOYSA-N 0.000 description 1
- UOQRKDSICWXMLF-UHFFFAOYSA-N 2-(2-methylpiperazin-1-yl)-3-(2-phenoxyethoxy)pyrazine Chemical compound CC1CNCCN1C1=NC=CN=C1OCCOC1=CC=CC=C1 UOQRKDSICWXMLF-UHFFFAOYSA-N 0.000 description 1
- OGSQJVTXVWJAQB-UHFFFAOYSA-N 2-(3,4-dihydro-2H-chromen-2-ylmethoxy)-3-piperazin-1-ylpyrazine Chemical compound C1CC2=CC=CC=C2OC1COC1=NC=CN=C1N1CCNCC1 OGSQJVTXVWJAQB-UHFFFAOYSA-N 0.000 description 1
- RIRDYRFKDIAAHF-UHFFFAOYSA-N 2-(3,4-dihydro-2H-chromen-2-ylmethoxy)-3-piperazin-1-ylquinoxaline Chemical compound C1CC2=CC=CC=C2OC1COC1=NC2=CC=CC=C2N=C1N1CCNCC1 RIRDYRFKDIAAHF-UHFFFAOYSA-N 0.000 description 1
- GUNDMXLMUHBMHX-UHFFFAOYSA-N 2-(3-methylpiperazin-1-yl)-3-(2-phenoxyethoxy)pyrazine Chemical compound C1CNC(C)CN1C1=NC=CN=C1OCCOC1=CC=CC=C1 GUNDMXLMUHBMHX-UHFFFAOYSA-N 0.000 description 1
- GAKAHYXHMYKXDP-AAFJCEBUSA-N 2-[(2R)-2-methylpiperazin-1-yl]-3-(1,2,3,4-tetrahydronaphthalen-2-ylmethoxy)pyrazine Chemical compound C[C@@H]1CNCCN1C1=NC=CN=C1OCC1CC2=CC=CC=C2CC1 GAKAHYXHMYKXDP-AAFJCEBUSA-N 0.000 description 1
- UOQRKDSICWXMLF-CQSZACIVSA-N 2-[(2R)-2-methylpiperazin-1-yl]-3-(2-phenoxyethoxy)pyrazine Chemical compound C[C@@H]1CNCCN1C1=NC=CN=C1OCCOC1=CC=CC=C1 UOQRKDSICWXMLF-CQSZACIVSA-N 0.000 description 1
- CDHRQOCSDKPMHG-UHFFFAOYSA-N 2-[(3-piperazin-1-ylpyrazin-2-yl)oxymethyl]-3,4-dihydro-2H-1,4-benzoxazine Chemical compound C1NC2=CC=CC=C2OC1COC1=NC=CN=C1N1CCNCC1 CDHRQOCSDKPMHG-UHFFFAOYSA-N 0.000 description 1
- KDNCXKHNRHFSFK-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-4-yloxy)ethoxy]-3-(2-methylpiperazin-1-yl)quinoxaline Chemical compound CC1CNCCN1C1=NC2=CC=CC=C2N=C1OCCOC1=CC=CC2=C1OCO2 KDNCXKHNRHFSFK-UHFFFAOYSA-N 0.000 description 1
- QYMHLVZLLUPJGQ-UHFFFAOYSA-N 2-[2-(2-chlorophenoxy)ethoxy]-3-(4-ethylpiperazin-1-yl)pyrazine Chemical compound C1CN(CC)CCN1C1=NC=CN=C1OCCOC1=CC=CC=C1Cl QYMHLVZLLUPJGQ-UHFFFAOYSA-N 0.000 description 1
- GHOUNYLHZVAUAW-UHFFFAOYSA-N 2-[2-(2-fluorophenoxy)ethoxy]-3-piperazin-1-ylpyrazine Chemical compound FC1=CC=CC=C1OCCOC1=NC=CN=C1N1CCNCC1 GHOUNYLHZVAUAW-UHFFFAOYSA-N 0.000 description 1
- YCWGCZDIODAJGE-UHFFFAOYSA-N 2-[2-(2-methoxyphenoxy)ethoxy]-3-piperazin-1-ylpyrazine Chemical compound COC1=CC=CC=C1OCCOC1=NC=CN=C1N1CCNCC1 YCWGCZDIODAJGE-UHFFFAOYSA-N 0.000 description 1
- VRZMNONHSMJKGY-UHFFFAOYSA-N 2-chloro-3-(2,3-dihydro-1,4-benzodioxin-3-ylmethoxy)pyrazine Chemical compound ClC1=NC=CN=C1OCC1OC2=CC=CC=C2OC1 VRZMNONHSMJKGY-UHFFFAOYSA-N 0.000 description 1
- OGTLIDNRGOUIAQ-SSDOTTSWSA-N 2-chloro-3-[(2R)-2-methylpiperazin-1-yl]pyrazine Chemical compound C[C@@H]1CNCCN1C1=NC=CN=C1Cl OGTLIDNRGOUIAQ-SSDOTTSWSA-N 0.000 description 1
- WTTPPBDTWKWPKP-UHFFFAOYSA-N 2-chloro-3-[2-(2-chlorophenoxy)ethoxy]pyrazine Chemical compound ClC1=CC=CC=C1OCCOC1=NC=CN=C1Cl WTTPPBDTWKWPKP-UHFFFAOYSA-N 0.000 description 1
- MRDAZRADHJDBEF-UHFFFAOYSA-N 2-chloro-3-piperazin-1-ylquinoxaline Chemical group ClC1=NC2=CC=CC=C2N=C1N1CCNCC1 MRDAZRADHJDBEF-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 1
- QNQSDMIJOCPHKF-UHFFFAOYSA-N 2-piperazin-1-yl-3-(1,2,3,4-tetrahydronaphthalen-2-ylmethoxy)pyrazine Chemical compound C1CC2=CC=CC=C2CC1COC1=NC=CN=C1N1CCNCC1 QNQSDMIJOCPHKF-UHFFFAOYSA-N 0.000 description 1
- HTQZGTZNEJGNCW-UHFFFAOYSA-N 2-piperazin-1-yl-3-[2-[3-(trifluoromethoxy)phenoxy]ethoxy]pyrazine Chemical compound FC(F)(F)OC1=CC=CC(OCCOC=2C(=NC=CN=2)N2CCNCC2)=C1 HTQZGTZNEJGNCW-UHFFFAOYSA-N 0.000 description 1
- XKQUZBGOHGUHQA-UHFFFAOYSA-N 2-tert-butyl-1,4-dioxane Chemical compound CC(C)(C)C1COCCO1 XKQUZBGOHGUHQA-UHFFFAOYSA-N 0.000 description 1
- HDDDVYQKGVCTRM-UHFFFAOYSA-N 3,4-dihydro-2H-1,4-benzoxazin-2-ylmethanol Chemical compound C1=CC=C2OC(CO)CNC2=C1 HDDDVYQKGVCTRM-UHFFFAOYSA-N 0.000 description 1
- MJTJJXOADZBDIN-UHFFFAOYSA-N 3-(2-isoquinolin-7-yloxyethoxy)-4-piperazin-1-yl-1,2,5-thiadiazole Chemical compound C=1C=C2C=CN=CC2=CC=1OCCOC1=NSN=C1N1CCNCC1 MJTJJXOADZBDIN-UHFFFAOYSA-N 0.000 description 1
- RLSLPOHWICBLJO-UHFFFAOYSA-N 3-[2-(3-piperazin-1-ylpyrazin-2-yl)oxyethoxy]benzonitrile Chemical compound N#CC1=CC=CC(OCCOC=2C(=NC=CN=2)N2CCNCC2)=C1 RLSLPOHWICBLJO-UHFFFAOYSA-N 0.000 description 1
- UDYWWFLOHZSCND-UHFFFAOYSA-N 5-chloro-8-[2-(3-piperazin-1-ylpyrazin-2-yl)oxyethoxy]quinolin-2-amine Chemical compound C12=NC(N)=CC=C2C(Cl)=CC=C1OCCOC1=NC=CN=C1N1CCNCC1 UDYWWFLOHZSCND-UHFFFAOYSA-N 0.000 description 1
- IPBHHYSZJBNDBX-UHFFFAOYSA-N 5-methyl-2-piperazin-1-yl-3-(2-pyridin-3-yloxyethoxy)pyrazine Chemical compound C=1C=CN=CC=1OCCOC1=NC(C)=CN=C1N1CCNCC1 IPBHHYSZJBNDBX-UHFFFAOYSA-N 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- VBPJQNGLWZSBLY-UHFFFAOYSA-N N-[8-[2-(3-piperazin-1-ylpyrazin-2-yl)oxyethoxy]quinolin-2-yl]acetamide Chemical compound C12=NC(NC(=O)C)=CC=C2C=CC=C1OCCOC1=NC=CN=C1N1CCNCC1 VBPJQNGLWZSBLY-UHFFFAOYSA-N 0.000 description 1
- AOGFSDGYGAKJKU-UHFFFAOYSA-N N-methyl-8-[2-(3-piperazin-1-ylpyrazin-2-yl)oxyethoxy]quinolin-2-amine Chemical compound C12=NC(NC)=CC=C2C=CC=C1OCCOC1=NC=CN=C1N1CCNCC1 AOGFSDGYGAKJKU-UHFFFAOYSA-N 0.000 description 1
- IOZCBYGNJPZBSW-UHFFFAOYSA-M O1CCOC2=C1C=CC(=C2)OCCOC=1C(=NC=CN=1)N1CCN(CC1)C(=O)[O-] Chemical compound O1CCOC2=C1C=CC(=C2)OCCOC=1C(=NC=CN=1)N1CCN(CC1)C(=O)[O-] IOZCBYGNJPZBSW-UHFFFAOYSA-M 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N Phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 229960005323 Phenoxyethanol Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- WCRKBMABEPCYII-UHFFFAOYSA-N isoquinolin-7-ol Chemical compound C1=CN=CC2=CC(O)=CC=C21 WCRKBMABEPCYII-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-L maleate(2-) Chemical compound [O-]C(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-L 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N oxygen atom Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Inorganic materials [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atoms Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- BFFLLBPMZCIGRM-QMMMGPOBSA-N tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1CO BFFLLBPMZCIGRM-QMMMGPOBSA-N 0.000 description 1
- RFRGDSDUSZMJFH-KRWDZBQOSA-N tert-butyl (2S)-2-[[3-(2-phenoxyethoxy)pyrazin-2-yl]oxymethyl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1COC1=NC=CN=C1OCCOC1=CC=CC=C1 RFRGDSDUSZMJFH-KRWDZBQOSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9901884-8 | 1999-05-21 | ||
| SE9901884A SE9901884D0 (sv) | 1999-05-21 | 1999-05-21 | Novel compounds their use and preparation |
| US13752799P | 1999-06-03 | 1999-06-03 | |
| US60/137,527 | 1999-06-03 | ||
| PCT/SE2000/001017 WO2000076984A2 (en) | 1999-05-21 | 2000-05-19 | Novel compounds, their use and preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003502317A JP2003502317A (ja) | 2003-01-21 |
| JP2003502317A5 true JP2003502317A5 (ko) | 2007-07-12 |
| JP4831903B2 JP4831903B2 (ja) | 2011-12-07 |
Family
ID=20415714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001503842A Expired - Fee Related JP4831903B2 (ja) | 1999-05-21 | 2000-05-19 | 新規化合物、その使用および製造 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JP4831903B2 (ko) |
| AR (1) | AR030022A1 (ko) |
| MY (1) | MY135666A (ko) |
| PE (1) | PE20010125A1 (ko) |
| SE (1) | SE9901884D0 (ko) |
| ZA (1) | ZA200109571B (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8013156B2 (en) * | 2003-03-19 | 2011-09-06 | Exelixis, Inc. | Tie-2 modulators and methods of use |
| CL2004000826A1 (es) * | 2003-04-25 | 2005-03-04 | Pfizer | Uso de un agonista para el receptor 5-ht2c para preparar un medicamento util en el tratamiento de la incontinencia urinaria provocada por estres, con la condicion de que el agonista no sea 1-[6-cloro-5-(trifluorometil)-2-piridinil]piperazina (org-129 |
| KR101270841B1 (ko) | 2005-02-28 | 2013-06-05 | 가부시키가이샤 메이지 | 히드로퀴논 장쇄 유도체 및／또는 페녹시 장쇄 유도체 및 이들을 함유하는 의약 |
| CA2621164A1 (en) * | 2005-08-26 | 2007-03-01 | Shionogi & Co., Ltd. | Derivative having ppar agonistic activity |
| JP6635999B2 (ja) * | 2017-10-13 | 2020-01-29 | 株式会社ダイセル | カリウム塩の製造方法、及びカリウム塩 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI193974A (ko) * | 1973-07-13 | 1975-01-14 | Merck & Co Inc | |
| GB9420999D0 (en) * | 1994-10-18 | 1994-12-07 | Smithkline Beecham Plc | Novel compounds |
-
1999
- 1999-05-21 SE SE9901884A patent/SE9901884D0/xx unknown
-
2000
- 2000-05-19 JP JP2001503842A patent/JP4831903B2/ja not_active Expired - Fee Related
- 2000-05-19 AR ARP000102461A patent/AR030022A1/es active IP Right Grant
- 2000-05-19 MY MYPI20002186A patent/MY135666A/en unknown
- 2000-05-19 PE PE2000000479A patent/PE20010125A1/es not_active Application Discontinuation
-
2001
- 2001-11-20 ZA ZA200109571A patent/ZA200109571B/xx unknown
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