TWI504602B - 吡里哌若平（ｐｙｒｉｐｙｒｏｐｅｎｅ）衍生物的製造方法 - Google Patents
吡里哌若平（ｐｙｒｉｐｙｒｏｐｅｎｅ）衍生物的製造方法 Download PDFInfo
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- TWI504602B TWI504602B TW099139126A TW99139126A TWI504602B TW I504602 B TWI504602 B TW I504602B TW 099139126 A TW099139126 A TW 099139126A TW 99139126 A TW99139126 A TW 99139126A TW I504602 B TWI504602 B TW I504602B
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- Prior art keywords
- compound
- group
- producing
- ethyl acetate
- cyclopropanecarbonyl
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- 238000000034 method Methods 0.000 title claims description 73
- 229930188995 pyripyropene Natural products 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 236
- 150000001875 compounds Chemical class 0.000 claims description 139
- 238000006243 chemical reaction Methods 0.000 claims description 81
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 69
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 65
- 239000002904 solvent Substances 0.000 claims description 61
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 30
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 26
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 239000012043 crude product Substances 0.000 claims description 19
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 18
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 14
- 239000003495 polar organic solvent Substances 0.000 claims description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 238000002425 crystallisation Methods 0.000 claims description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 11
- 230000008025 crystallization Effects 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 11
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 9
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 238000006146 oximation reaction Methods 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 7
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- -1 cyclopropanecarbonyl group Chemical group 0.000 claims description 7
- 238000001704 evaporation Methods 0.000 claims description 7
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 6
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 230000000887 hydrating effect Effects 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 235000019439 ethyl acetate Nutrition 0.000 description 76
- 239000000203 mixture Substances 0.000 description 73
- 239000002585 base Substances 0.000 description 61
- 239000013078 crystal Substances 0.000 description 58
- 239000000243 solution Substances 0.000 description 58
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 37
- 239000000725 suspension Substances 0.000 description 37
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 36
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 26
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 26
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 26
- 235000017557 sodium bicarbonate Nutrition 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000001914 filtration Methods 0.000 description 24
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- 239000000843 powder Substances 0.000 description 18
- 239000012453 solvate Substances 0.000 description 17
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 15
- 235000011121 sodium hydroxide Nutrition 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 238000000926 separation method Methods 0.000 description 13
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 235000011181 potassium carbonates Nutrition 0.000 description 12
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 235000017550 sodium carbonate Nutrition 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 9
- 239000011736 potassium bicarbonate Substances 0.000 description 9
- 235000015497 potassium bicarbonate Nutrition 0.000 description 9
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 9
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 9
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 9
- 235000011118 potassium hydroxide Nutrition 0.000 description 9
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 239000012046 mixed solvent Substances 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 7
- 229910001863 barium hydroxide Inorganic materials 0.000 description 7
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 7
- 239000000920 calcium hydroxide Substances 0.000 description 7
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 7
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 7
- 150000007529 inorganic bases Chemical class 0.000 description 7
- 150000007530 organic bases Chemical class 0.000 description 7
- 229910000105 potassium hydride Inorganic materials 0.000 description 7
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 7
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 230000002140 halogenating effect Effects 0.000 description 6
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- BMAZLDDSIXOBAO-UHFFFAOYSA-N (1,3,5-trichlorocyclohexa-2,4-diene-1-carbonyl) 1,3,5-trichlorocyclohexa-2,4-diene-1-carboxylate Chemical compound ClC1(C(=O)OC(C2(CC(=CC(=C2)Cl)Cl)Cl)=O)CC(=CC(=C1)Cl)Cl BMAZLDDSIXOBAO-UHFFFAOYSA-N 0.000 description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 5
- CSNALVKUVSCWHX-UHFFFAOYSA-N NNC(C(CC(Cl)=C1)(C=C1Cl)Cl)=O.Cl Chemical compound NNC(C(CC(Cl)=C1)(C=C1Cl)Cl)=O.Cl CSNALVKUVSCWHX-UHFFFAOYSA-N 0.000 description 5
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
- LZEPOJMTQYNFTR-UHFFFAOYSA-N cyclopropanecarbonyl cyclopropanecarboxylate Chemical compound C1CC1C(=O)OC(=O)C1CC1 LZEPOJMTQYNFTR-UHFFFAOYSA-N 0.000 description 5
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 5
- 239000000347 magnesium hydroxide Substances 0.000 description 5
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 5
- 238000000634 powder X-ray diffraction Methods 0.000 description 5
- PUABNAWFNOFZPZ-UHFFFAOYSA-N 2,3,5,6,7,8,9,9a-octahydro-1h-benzo[7]annulene Chemical compound C1CCCCC2CCCC=C21 PUABNAWFNOFZPZ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000006612 decyloxy group Chemical group 0.000 description 4
- 239000002024 ethyl acetate extract Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 3
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- AOIYTIDHFMNVOO-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydro-1h-indene Chemical compound C1CCC=C2CCCC21 AOIYTIDHFMNVOO-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-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
- 238000000746 purification Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- HAAKBIBLBRNJDN-UHFFFAOYSA-N 2,2-dimethylpropanoyl cyclopropanecarboxylate Chemical compound CC(C)(C)C(=O)OC(=O)C1CC1 HAAKBIBLBRNJDN-UHFFFAOYSA-N 0.000 description 1
- MAQAGRJURDEYDQ-UHFFFAOYSA-N 6-methylpyridine Chemical compound CC1=C=CC=C[N]1 MAQAGRJURDEYDQ-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000002083 X-ray spectrum Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- ASFGFTBMABJNSO-UHFFFAOYSA-N butylsulfanium;chloride Chemical compound [Cl-].CCCC[SH2+] ASFGFTBMABJNSO-UHFFFAOYSA-N 0.000 description 1
- 210000000692 cap cell Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- ROPBDLZCVLFSRF-SXGRAWJWSA-N chembl328676 Chemical compound C([C@@]1(C)C2C[C@@H]([C@]3(OC4=C(C(OC(=C4)C=4C=NC=CC=4)=O)[C@H](O)C3[C@@]2(C)CC[C@@H]1O1)C)OC(=O)C(N)CCC)OC21CCCCC2 ROPBDLZCVLFSRF-SXGRAWJWSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZLDHYRXZZNDOKU-UHFFFAOYSA-N n,n-diethyl-3-trimethoxysilylpropan-1-amine Chemical compound CCN(CC)CCC[Si](OC)(OC)OC ZLDHYRXZZNDOKU-UHFFFAOYSA-N 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000008823 permeabilization Effects 0.000 description 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
- 229960002702 piroxicam Drugs 0.000 description 1
- 229960003975 potassium Drugs 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
- 238000001556 precipitation Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010044416 | 2010-03-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201139447A TW201139447A (en) | 2011-11-16 |
| TWI504602B true TWI504602B (zh) | 2015-10-21 |
Family
ID=43528310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099139126A TWI504602B (zh) | 2010-03-01 | 2010-11-11 | 吡里哌若平（ｐｙｒｉｐｙｒｏｐｅｎｅ）衍生物的製造方法 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8853414B2 (https=) |
| EP (1) | EP2542555B1 (https=) |
| JP (1) | JP5717752B2 (https=) |
| KR (1) | KR101787789B1 (https=) |
| CN (1) | CN102947312B (https=) |
| AR (1) | AR078975A1 (https=) |
| BR (1) | BR112012021911B8 (https=) |
| CA (1) | CA2791660C (https=) |
| CR (1) | CR20120487A (https=) |
| DK (1) | DK2542555T3 (https=) |
| EC (1) | ECSP12012203A (https=) |
| ES (1) | ES2607191T3 (https=) |
| IL (1) | IL221651A (https=) |
| MX (1) | MX2012010173A (https=) |
| NZ (1) | NZ602719A (https=) |
| RU (1) | RU2578605C2 (https=) |
| TW (1) | TWI504602B (https=) |
| UA (1) | UA111151C2 (https=) |
| WO (1) | WO2011108155A1 (https=) |
| ZA (1) | ZA201207335B (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2426124B1 (en) * | 2009-05-13 | 2013-08-07 | Meiji Seika Pharma Co., Ltd. | Process for producing pyripyropene derivative |
| UA111151C2 (uk) | 2010-03-01 | 2016-04-11 | Мейдзі Сейка Фарма Ко., Лтд. | Спосіб одержання похідних пірипіропену |
| ES2534745T3 (es) * | 2010-09-14 | 2015-04-28 | Basf Se | Composición que contiene un insecticida de piripiropeno y un adyuvante |
| JP6174057B2 (ja) * | 2012-03-12 | 2017-08-02 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ピリピロペン殺虫剤の水性懸濁濃厚製剤の調製方法 |
| AU2014206958B2 (en) * | 2013-01-16 | 2017-08-10 | Basf Se | Method for preparing a pyripyropene compound |
| JP6215355B2 (ja) * | 2013-01-25 | 2017-10-18 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 水性懸濁製剤の調製方法 |
| ES2705537T3 (es) | 2013-03-28 | 2019-03-25 | Basf Se | Producción de piripiropenos a partir de biomasa seca |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2061207A1 (en) * | 1991-09-23 | 1993-03-24 | Kenneth R. Theis | Starting multi-speed motors at a low speed connection |
| EP2107060A1 (en) * | 2006-11-30 | 2009-10-07 | Meiji Seika Kaisha Ltd. | Pest control agent |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3233476B2 (ja) | 1992-10-22 | 2001-11-26 | 社団法人北里研究所 | Ｆｏ−１２８９物質およびその製造法 |
| JPH08239385A (ja) | 1995-03-03 | 1996-09-17 | Kitasato Inst:The | Ｆｏ−１２８９物質およびその製造法 |
| JP3725198B2 (ja) * | 1995-03-27 | 2005-12-07 | 社団法人北里研究所 | ピリピロペン誘導体 |
| JPH08269065A (ja) | 1995-04-03 | 1996-10-15 | Kitasato Inst:The | ピリピロペン誘導体 |
| KR100522446B1 (ko) | 2003-01-07 | 2005-10-18 | 한국생명공학연구원 | 아실 코에이:콜레스테롤 아실 트란스퍼라제의 저해활성을갖는 화합물 또는 그 염을 유효성분으로 하는 살충제 |
| JP5179174B2 (ja) | 2004-05-28 | 2013-04-10 | ノバルティス ファーマ アーゲー | アルドステロンシンターゼ阻害剤としてのテトラヒドロ−イミダゾ［１，５−ａ］ピリジン誘導体 |
| US7491738B2 (en) | 2005-06-01 | 2009-02-17 | Meiji Seika Kaisha, Ltd. | Pest control agents |
| TWI388282B (zh) | 2005-06-01 | 2013-03-11 | Meiji Seika Pharma Co Ltd | 害蟲控制劑 |
| JP2008050997A (ja) | 2006-08-24 | 2008-03-06 | Matsushita Electric Ind Co Ltd | 密閉型電動圧縮機 |
| JP4488033B2 (ja) | 2007-02-06 | 2010-06-23 | ソニー株式会社 | 偏光素子及び液晶プロジェクター |
| EP2186815A4 (en) | 2007-08-13 | 2012-01-25 | Meiji Seika Kaisha | PROCESS FOR PREPARING A PYRIPYROPEN DERIVATIVE AND INTERMEDIATE PRODUCT |
| TW200936047A (en) | 2007-12-21 | 2009-09-01 | Meiji Seika Kaisha | Novel systemic pesticide |
| EP2426124B1 (en) | 2009-05-13 | 2013-08-07 | Meiji Seika Pharma Co., Ltd. | Process for producing pyripyropene derivative |
| UA111151C2 (uk) | 2010-03-01 | 2016-04-11 | Мейдзі Сейка Фарма Ко., Лтд. | Спосіб одержання похідних пірипіропену |
-
2010
- 2010-10-11 UA UAA201211289A patent/UA111151C2/uk unknown
- 2010-11-10 WO PCT/JP2010/070414 patent/WO2011108155A1/en not_active Ceased
- 2010-11-10 MX MX2012010173A patent/MX2012010173A/es active IP Right Grant
- 2010-11-10 DK DK10788151.8T patent/DK2542555T3/da active
- 2010-11-10 KR KR1020127025488A patent/KR101787789B1/ko active Active
- 2010-11-10 JP JP2012540182A patent/JP5717752B2/ja active Active
- 2010-11-10 CA CA2791660A patent/CA2791660C/en active Active
- 2010-11-10 RU RU2012141555/04A patent/RU2578605C2/ru active
- 2010-11-10 EP EP10788151.8A patent/EP2542555B1/en active Active
- 2010-11-10 CN CN201080065119.7A patent/CN102947312B/zh active Active
- 2010-11-10 ES ES10788151.8T patent/ES2607191T3/es active Active
- 2010-11-10 US US13/581,857 patent/US8853414B2/en active Active
- 2010-11-10 NZ NZ602719A patent/NZ602719A/en unknown
- 2010-11-10 BR BR112012021911A patent/BR112012021911B8/pt active IP Right Grant
- 2010-11-11 TW TW099139126A patent/TWI504602B/zh active
- 2010-11-11 AR ARP100104185A patent/AR078975A1/es active IP Right Grant
-
2012
- 2012-08-27 IL IL221651A patent/IL221651A/en active IP Right Grant
- 2012-09-26 CR CR20120487A patent/CR20120487A/es unknown
- 2012-10-01 ZA ZA2012/07335A patent/ZA201207335B/en unknown
- 2012-10-01 EC ECSP12012203 patent/ECSP12012203A/es unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2061207A1 (en) * | 1991-09-23 | 1993-03-24 | Kenneth R. Theis | Starting multi-speed motors at a low speed connection |
| EP2107060A1 (en) * | 2006-11-30 | 2009-10-07 | Meiji Seika Kaisha Ltd. | Pest control agent |
Non-Patent Citations (1)
| Title |
|---|
| Obata et al, The Journal of Antibiotics,1996, 49,(11), p1133-1148 * |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20130040180A (ko) | 2013-04-23 |
| US20130060042A1 (en) | 2013-03-07 |
| UA111151C2 (uk) | 2016-04-11 |
| CA2791660A1 (en) | 2011-09-09 |
| ES2607191T3 (es) | 2017-03-29 |
| WO2011108155A1 (en) | 2011-09-09 |
| RU2012141555A (ru) | 2014-04-10 |
| AU2010347354B2 (en) | 2016-09-01 |
| CA2791660C (en) | 2020-09-22 |
| JP2013521224A (ja) | 2013-06-10 |
| ZA201207335B (en) | 2014-01-29 |
| EP2542555A1 (en) | 2013-01-09 |
| KR101787789B1 (ko) | 2017-10-18 |
| CN102947312B (zh) | 2015-05-27 |
| AR078975A1 (es) | 2011-12-14 |
| ECSP12012203A (es) | 2013-06-28 |
| JP5717752B2 (ja) | 2015-05-13 |
| BR112012021911B1 (pt) | 2021-06-08 |
| TW201139447A (en) | 2011-11-16 |
| DK2542555T3 (da) | 2017-01-02 |
| US8853414B2 (en) | 2014-10-07 |
| RU2578605C2 (ru) | 2016-03-27 |
| BR112012021911A2 (pt) | 2015-09-29 |
| MX2012010173A (es) | 2012-10-03 |
| NZ602719A (en) | 2015-01-30 |
| CR20120487A (es) | 2013-01-11 |
| BR112012021911B8 (pt) | 2022-08-02 |
| AU2010347354A1 (en) | 2012-10-25 |
| IL221651A (en) | 2017-05-29 |
| EP2542555B1 (en) | 2016-09-21 |
| CN102947312A (zh) | 2013-02-27 |
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