JPWO2007122847A1 - 有機合成用試薬、及び当該試薬を用いた有機合成反応方法 - Google Patents
有機合成用試薬、及び当該試薬を用いた有機合成反応方法 Download PDFInfo
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- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 description 2
- NRPFNQUDKRYCNX-UHFFFAOYSA-N 4-methoxyphenylacetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1 NRPFNQUDKRYCNX-UHFFFAOYSA-N 0.000 description 2
- UTUKHRWZEYOXML-UHFFFAOYSA-N 5-(bromomethyl)-1,2,3-trioctadecoxybenzene Chemical compound CCCCCCCCCCCCCCCCCCOC1=CC(CBr)=CC(OCCCCCCCCCCCCCCCCCC)=C1OCCCCCCCCCCCCCCCCCC UTUKHRWZEYOXML-UHFFFAOYSA-N 0.000 description 2
- OEBXWWBYZJNKRK-UHFFFAOYSA-N CN1C2=NCCCN2CCC1 Chemical compound CN1C2=NCCCN2CCC1 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000010640 amide synthesis reaction Methods 0.000 description 2
- 125000005604 azodicarboxylate group Chemical group 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000010701 ester synthesis reaction Methods 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 238000010702 ether synthesis reaction Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- FBSFWRHWHYMIOG-UHFFFAOYSA-N methyl 3,4,5-trihydroxybenzoate Chemical group COC(=O)C1=CC(O)=C(O)C(O)=C1 FBSFWRHWHYMIOG-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 238000007040 multi-step synthesis reaction Methods 0.000 description 2
- QDYGCAOQFANHSG-UHFFFAOYSA-N octadecoxybenzene Chemical compound CCCCCCCCCCCCCCCCCCOC1=CC=CC=C1 QDYGCAOQFANHSG-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000011085 pressure filtration Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- IXAYZHCPEYTWHW-IBGZPJMESA-N (2r)-3-tert-butylsulfanyl-2-(9h-fluoren-9-ylmethoxycarbonylamino)propanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CSC(C)(C)C)C(O)=O)C3=CC=CC=C3C2=C1 IXAYZHCPEYTWHW-IBGZPJMESA-N 0.000 description 1
- SJVFAHZPLIXNDH-QFIPXVFZSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 SJVFAHZPLIXNDH-QFIPXVFZSA-N 0.000 description 1
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical group O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- MCDJYAYOEMBQRK-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-3,5-di(docosoxy)benzene Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC1=CC(OCCCCCCCCCCCCCCCCCCCCCC)=CC(C(Cl)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 MCDJYAYOEMBQRK-UHFFFAOYSA-N 0.000 description 1
- YQJJSVZQDQBDQD-UHFFFAOYSA-N 1-[chloro-(4,4-dichlorocyclohexa-1,5-dien-1-yl)methyl]-3,5-di(docosoxy)benzene Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC1=CC(OCCCCCCCCCCCCCCCCCCCCCC)=CC(C(Cl)C=2C=CC(Cl)(Cl)CC=2)=C1 YQJJSVZQDQBDQD-UHFFFAOYSA-N 0.000 description 1
- BJRNQGBSGKWNCB-UHFFFAOYSA-N 2-[[3,5-di(docosoxy)phenyl]methyl]-4-diphenylphosphanylbenzoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC1=CC(OCCCCCCCCCCCCCCCCCCCCCC)=CC(CC=2C(=CC=C(C=2)P(C=2C=CC=CC=2)C=2C=CC=CC=2)C(O)=O)=C1 BJRNQGBSGKWNCB-UHFFFAOYSA-N 0.000 description 1
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 1
- GXMHDTPYKRTARV-UHFFFAOYSA-N 4-diphenylphosphanylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 GXMHDTPYKRTARV-UHFFFAOYSA-N 0.000 description 1
- CZMOPBHEGIWINN-UHFFFAOYSA-N COC1OC1N Chemical compound COC1OC1N CZMOPBHEGIWINN-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- JQRFZHLSVNTDMO-UHFFFAOYSA-N N-[[2,4-di(docosoxy)phenyl]methylidene]hydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC1=CC=C(C=NO)C(OCCCCCCCCCCCCCCCCCCCCCC)=C1 JQRFZHLSVNTDMO-UHFFFAOYSA-N 0.000 description 1
- QZBUWPVZSXDWSB-UHFFFAOYSA-N O=C(C1N2CCC1)NC(Cc1ccccc1)C2=O Chemical compound O=C(C1N2CCC1)NC(Cc1ccccc1)C2=O QZBUWPVZSXDWSB-UHFFFAOYSA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- ZOSQKYOBDXZORG-UHFFFAOYSA-N [2,4-di(docosoxy)phenyl]methanamine Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC1=CC=C(CN)C(OCCCCCCCCCCCCCCCCCCCCCC)=C1 ZOSQKYOBDXZORG-UHFFFAOYSA-N 0.000 description 1
- QDBGTPIUAHDASH-UHFFFAOYSA-N [3,5-di(docosoxy)phenyl]methanol Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC1=CC(CO)=CC(OCCCCCCCCCCCCCCCCCCCCCC)=C1 QDBGTPIUAHDASH-UHFFFAOYSA-N 0.000 description 1
- BLWWLFLHBATVGY-UHFFFAOYSA-M [Br-].C1CCOC1.[Mg+]C1=CC=C(Cl)C=C1 Chemical compound [Br-].C1CCOC1.[Mg+]C1=CC=C(Cl)C=C1 BLWWLFLHBATVGY-UHFFFAOYSA-M 0.000 description 1
- OFJJGSAYWPNTEW-UHFFFAOYSA-M [Br-].C1CCOC1.[Mg+]C1=CC=CC=C1 Chemical compound [Br-].C1CCOC1.[Mg+]C1=CC=CC=C1 OFJJGSAYWPNTEW-UHFFFAOYSA-M 0.000 description 1
- RAYIJRRLHAWAFV-UHFFFAOYSA-N [carboxy-[[3,5-di(docosoxy)phenyl]methyl]amino]-ethylcarbamic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC1=CC(CN(N(CC)C(O)=O)C(O)=O)=CC(OCCCCCCCCCCCCCCCCCCCCCC)=C1 RAYIJRRLHAWAFV-UHFFFAOYSA-N 0.000 description 1
- DORMTBIPKNPJPY-UHFFFAOYSA-N acetic acid;iodobenzene Chemical compound CC(O)=O.IC1=CC=CC=C1 DORMTBIPKNPJPY-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 238000007350 electrophilic reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 1
- ANSUDRATXSJBLY-VKHMYHEASA-N methyl (2s)-2-amino-3-hydroxypropanoate Chemical compound COC(=O)[C@@H](N)CO ANSUDRATXSJBLY-VKHMYHEASA-N 0.000 description 1
- IBKQQKPQRYUGBJ-UHFFFAOYSA-N methyl gallate Natural products CC(=O)C1=CC(O)=C(O)C(O)=C1 IBKQQKPQRYUGBJ-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- MIKVYRWSUUCYNM-UHFFFAOYSA-N propan-2-yl 2-(4-methoxyphenyl)acetate Chemical compound COC1=CC=C(CC(=O)OC(C)C)C=C1 MIKVYRWSUUCYNM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000956 solid--liquid extraction Methods 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/20—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group the two nitrogen atoms of the functional groups being doubly-bound to each other, e.g. azoformamide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
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| JP2006084019 | 2006-03-24 | ||
| JP2006084019 | 2006-03-24 | ||
| PCT/JP2007/052996 WO2007122847A1 (ja) | 2006-03-24 | 2007-02-19 | 有機合成用試薬、及び当該試薬を用いた有機合成反応方法 |
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| JP2009120386A Active JP5113118B2 (ja) | 2006-03-24 | 2009-05-18 | 有機合成用試薬、及び当該試薬を用いた有機合成反応方法 |
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| JP2009120386A Active JP5113118B2 (ja) | 2006-03-24 | 2009-05-18 | 有機合成用試薬、及び当該試薬を用いた有機合成反応方法 |
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| EP (1) | EP2003104B1 (https=) |
| JP (2) | JPWO2007122847A1 (https=) |
| CN (1) | CN101405240B (https=) |
| AU (1) | AU2007242276A1 (https=) |
| DK (1) | DK2003104T3 (https=) |
| ES (1) | ES2546808T3 (https=) |
| WO (1) | WO2007122847A1 (https=) |
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| ES2546808T3 (es) * | 2006-03-24 | 2015-09-28 | Jitsubo Co., Ltd. | Reactivo para síntesis orgánica y método de reacción de síntesis orgánica con dicho reactivo |
| EP2415744A4 (en) | 2009-03-12 | 2014-03-19 | Ajinomoto Kk | FLUORENE COMPOUND |
| WO2010113939A1 (ja) | 2009-03-30 | 2010-10-07 | 味の素株式会社 | ジフェニルメタン化合物 |
| JP5803674B2 (ja) | 2009-12-25 | 2015-11-04 | 味の素株式会社 | ベンジル化合物 |
| CN107011132B (zh) * | 2010-08-30 | 2020-11-10 | 味之素株式会社 | 含有支链的芳香族化合物 |
| CN103415530A (zh) | 2011-03-09 | 2013-11-27 | Jitsubo株式会社 | 新型的含有非肽性交联结构的交联肽、以及该交联肽的合成方法和用于该方法的新型有机化合物 |
| JP5979139B2 (ja) | 2011-05-17 | 2016-08-24 | 味の素株式会社 | オリゴヌクレオチドの製造方法 |
| JP6011528B2 (ja) | 2011-05-31 | 2016-10-19 | 味の素株式会社 | ペプチドの製造方法 |
| WO2012165546A1 (ja) * | 2011-05-31 | 2012-12-06 | 味の素株式会社 | ペプチドの製造方法 |
| CN102584546A (zh) * | 2011-09-26 | 2012-07-18 | 盘锦兴福化工有限公司 | 2,3—二氟苯乙醚的合成方法 |
| US9057712B1 (en) | 2011-10-27 | 2015-06-16 | Copilot Ventures Fund Iii Llc | Methods of delivery of encapsulated perfluorocarbon taggants |
| EP2921499B1 (en) | 2012-11-14 | 2020-01-22 | Takeda Pharmaceutical Company Limited | Method for liquid-phase synthesis of nucleic acids |
| US9504747B2 (en) | 2013-03-08 | 2016-11-29 | Novartis Ag | Lipids and lipid compositions for the delivery of active agents |
| EP3608308B1 (en) | 2013-03-08 | 2021-07-21 | Novartis AG | Lipids and lipid compositions for the delivery of active agents |
| WO2014189142A1 (ja) | 2013-05-24 | 2014-11-27 | 味の素株式会社 | モルフォリノオリゴヌクレオチドの製造方法 |
| US9365615B2 (en) | 2013-09-09 | 2016-06-14 | Jitsubo Co., Ltd. | Cross-linked peptides containing non-peptide cross-linked structure, method for synthesizing cross-linked peptides, and novel organic compound used in method |
| EP3263579B1 (en) | 2015-01-21 | 2022-11-30 | Ajinomoto Co., Inc. | Precipitation promoter and precipitation method in which same is used |
| EP3266792B1 (en) * | 2015-03-04 | 2020-12-30 | Jitsubo Co., Ltd. | Peptide synthesis method |
| KR101889893B1 (ko) * | 2015-06-12 | 2018-08-22 | 애니젠 주식회사 | 선별적 용해도를 갖는 트리페닐메탄 유도체 및 그의 용도 |
| KR102337328B1 (ko) | 2015-12-21 | 2021-12-10 | 텍사스 테크 유니버시티 시스템 | 용액상 gap 펩타이드 합성을 위한 시스템 및 방법 |
| US10981940B2 (en) | 2016-11-11 | 2021-04-20 | SEKISUl MEDICAL CO., LTD. | Trityl protecting agent |
| EP3480195A1 (en) | 2017-11-07 | 2019-05-08 | Bayer Animal Health GmbH | Method for the synthesis of cyclic depsipeptides |
| PL3676265T3 (pl) | 2017-11-07 | 2025-12-15 | Elanco Animal Health Gmbh | Sposób syntezy cyklicznych depsypeptydów |
| EP3778621B1 (en) | 2018-04-13 | 2023-08-23 | Jitsubo Co., Ltd. | Peptide synthesis method |
| US12024537B2 (en) | 2018-05-31 | 2024-07-02 | Sederma | Compositions and methods for chemical synthesis |
| EP3882255A4 (en) | 2018-11-16 | 2022-09-21 | Ajinomoto Co., Inc. | PROCESS FOR THE PREPARATION OF CYCLIZED PEPTIDE WITH INTRAMOLECULAR S-S BOND |
| EP3917937A4 (en) | 2019-02-01 | 2022-11-23 | Sederma | SYNTHETIC STRATEGY FOR A SPLIT PROTECTION GROUP |
| JP7628073B2 (ja) | 2019-02-28 | 2025-02-07 | 富士フイルム株式会社 | ペプチド化合物の製造方法、保護基形成用試薬、及び、芳香族複素環化合物 |
| JP7661880B2 (ja) | 2019-04-25 | 2025-04-15 | 味の素株式会社 | ペプチドの連続的製造方法 |
| JP7301965B2 (ja) | 2019-06-28 | 2023-07-03 | 富士フイルム株式会社 | ペプチド化合物の製造方法、保護基形成用試薬、及び、縮合多環化合物 |
| JP7814933B2 (ja) | 2019-08-29 | 2026-02-17 | 富士フイルム株式会社 | 核酸化合物の製造方法、及び、核酸化合物 |
| US20250282813A1 (en) | 2021-04-09 | 2025-09-11 | Bachem Holding Ag | Pseudo solid phase protecting group and methods for the synthesis of oligonucleotides and oligonucleotide conjugates |
| JP7162853B1 (ja) | 2021-07-02 | 2022-10-31 | ペプチスター株式会社 | 液相ペプチド合成用担体結合ペプチドの分析方法 |
| EP4596567A1 (en) | 2022-11-01 | 2025-08-06 | Chugai Seiyaku Kabushiki Kaisha | Method for removing dibenzofulvene or dibenzofulvene derivative |
| JPWO2024143514A1 (https=) | 2022-12-28 | 2024-07-04 | ||
| EP4516392A1 (en) | 2023-09-04 | 2025-03-05 | Vito NV | Peptides, peptidic nucleic acids (pna) and oligonucleotides synthesis assisted by membrane extraction |
| TW202542173A (zh) | 2023-12-06 | 2025-11-01 | 美商安進公司 | 液相肽合成方法 |
| CN119462823B (zh) * | 2024-11-08 | 2025-11-11 | 西北工业大学 | 金团簇纳米酶配体和自组装水凝胶及水凝胶制备方法 |
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| US4014937A (en) * | 1974-08-26 | 1977-03-29 | Pfizer Inc. | 3,4-And 3,5-dialkoxyphenethylamines |
| JPH06239995A (ja) * | 1993-02-22 | 1994-08-30 | Matsushita Electric Works Ltd | ポリアニリン誘導体およびその製造方法 |
| JP3919227B2 (ja) | 1996-05-02 | 2007-05-23 | テルモ株式会社 | アミジン誘導体及びそれを構成成分とする薬物担体 |
| JP2000044493A (ja) * | 1998-07-27 | 2000-02-15 | Asahi Chem Ind Co Ltd | 化合物ライブラリー合成用保護基 |
| JP2001122889A (ja) | 1999-10-26 | 2001-05-08 | Noguchi Inst | 糖脂質アナログ化合物 |
| US6806357B1 (en) | 2001-08-20 | 2004-10-19 | University Of Pittsburgh | Fluorous nucleophilic substitution of alcohols and reagents for use therein |
| JP4283469B2 (ja) * | 2001-12-19 | 2009-06-24 | 独立行政法人科学技術振興機構 | 相溶性−多相有機溶媒システムによりアミノ酸を逐次的に付加する液相ペプチド合成法 |
| US20040214989A1 (en) * | 2001-08-24 | 2004-10-28 | Kazuhiro Chiba | Compatible-multiphase organic solvent system |
| JP2003292494A (ja) | 2002-04-01 | 2003-10-15 | Japan Science & Technology Corp | 温度依存的集合形態を有するデンドリマー及びそれから成る発光体 |
| JP2004059509A (ja) | 2002-07-30 | 2004-02-26 | Nokodai Tlo Kk | 液相ペプチド合成用アミノ酸試薬 |
| WO2004073852A1 (ja) * | 2003-02-24 | 2004-09-02 | Tokyo University Of Agriculture And Technology Tlo Co., Ltd. | 温度により相溶状態・分離状態が可逆変化する溶媒の組み合わせを用いた化学プロセス方法 |
| JP4360854B2 (ja) | 2003-07-08 | 2009-11-11 | テルモ株式会社 | グアニジン誘導体およびそれを構成成分とする薬物担体 |
| JPWO2006104166A1 (ja) | 2005-03-29 | 2008-09-11 | 国立大学法人東京農工大学 | 晶析分離用担体及び化合物の分離方法 |
| ES2546808T3 (es) * | 2006-03-24 | 2015-09-28 | Jitsubo Co., Ltd. | Reactivo para síntesis orgánica y método de reacción de síntesis orgánica con dicho reactivo |
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2007
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- 2007-02-19 CN CN2007800103222A patent/CN101405240B/zh active Active
- 2007-02-19 DK DK07714522.5T patent/DK2003104T3/en active
- 2007-02-19 AU AU2007242276A patent/AU2007242276A1/en not_active Abandoned
- 2007-02-19 JP JP2008511981A patent/JPWO2007122847A1/ja active Pending
- 2007-02-19 WO PCT/JP2007/052996 patent/WO2007122847A1/ja not_active Ceased
- 2007-02-19 US US12/225,442 patent/US8093435B2/en active Active
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| Publication number | Publication date |
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| AU2007242276A1 (en) | 2007-11-01 |
| US20090299103A1 (en) | 2009-12-03 |
| CN101405240B (zh) | 2012-07-25 |
| WO2007122847A1 (ja) | 2007-11-01 |
| US8093435B2 (en) | 2012-01-10 |
| JP2009185063A (ja) | 2009-08-20 |
| EP2003104A2 (en) | 2008-12-17 |
| ES2546808T3 (es) | 2015-09-28 |
| CN101405240A (zh) | 2009-04-08 |
| EP2003104A4 (en) | 2010-01-06 |
| US8293948B2 (en) | 2012-10-23 |
| JP5113118B2 (ja) | 2013-01-09 |
| DK2003104T3 (en) | 2015-08-10 |
| EP2003104A9 (en) | 2009-04-15 |
| US20120108788A1 (en) | 2012-05-03 |
| EP2003104B1 (en) | 2015-07-01 |
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