JPWO2022191313A5 - - Google Patents
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- JPWO2022191313A5 JPWO2022191313A5 JP2023505652A JP2023505652A JPWO2022191313A5 JP WO2022191313 A5 JPWO2022191313 A5 JP WO2022191313A5 JP 2023505652 A JP2023505652 A JP 2023505652A JP 2023505652 A JP2023505652 A JP 2023505652A JP WO2022191313 A5 JPWO2022191313 A5 JP WO2022191313A5
- Authority
- JP
- Japan
- Prior art keywords
- iodo
- benzene
- hydroxy
- iodane
- htib
- 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.)
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- PEZNEXFPRSOYPL-UHFFFAOYSA-N (bis(trifluoroacetoxy)iodo)benzene Chemical compound FC(F)(F)C(=O)OI(OC(=O)C(F)(F)F)C1=CC=CC=C1 PEZNEXFPRSOYPL-UHFFFAOYSA-N 0.000 description 8
- LRIUKPUCKCECPT-UHFFFAOYSA-N [hydroxy(phenyl)-$l^{3}-iodanyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OI(O)C1=CC=CC=C1 LRIUKPUCKCECPT-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 6
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- MPMSZXWCZKCHLQ-UHFFFAOYSA-N trihydridoiodine Chemical compound [H]I([H])[H] MPMSZXWCZKCHLQ-UHFFFAOYSA-N 0.000 description 4
- WACNXHCZHTVBJM-UHFFFAOYSA-N 1,2,3,4,5-pentafluorobenzene Chemical compound FC1=CC(F)=C(F)C(F)=C1F WACNXHCZHTVBJM-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 241000801593 Pida Species 0.000 description 2
- -1 R 5 is H Chemical group 0.000 description 2
- WSUYPCBSGVAXNY-UHFFFAOYSA-N [hydroxy(phenyl)-$l^{3}-iodanyl] methanesulfonate Chemical compound CS(=O)(=O)OI(O)C1=CC=CC=C1 WSUYPCBSGVAXNY-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 125000003545 alkoxy group Chemical group 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
Description
Ｐｒｏｃ．Ｎａｔｌ．Ａｃａｄ．Ｓｃｉ．Ｕ．Ｓ．Ａ．２０１５，１１２，１０６１１
ＢｅｉｌｓｔｅｉｎＪ．Ｏｒｇ．Ｃｈｅｍ．２０１８，１４，４１６
ＴｅｔｒａｈｅｄｒｏｎＬｅｔｔ．１９８６，２７，５７３９
Ｊ．Ａｍ．Ｃｈｅｍ．Ｓｏｃ．２００９，１３１，１６６６９
Ｊ．Ｏｒｇ．Ｃｈｅｍ．２０１６，８１，１０６００
Ｊ．Ａｍ．Ｃｈｅｍ．Ｓｏｃ．２０１９，１４１，６４８４
一実施形態において、λ３－ヨーダンは、式Ｒ４－Ｉ（ＯＲ５）２で表される化合物である（式中、Ｒ４は、無置換又は置換フェニル基であり、Ｒ５は、Ｈ、アセチル、トリフルオロアセチル、トシル、メタンスルホニル、及びこれらの組み合わせからなる群から選択される）。上記式の定義の通り、Ｒ４は「置換フェニル基」であってもよく、当該置換基としては、例えば、直鎖若しくは分枝状飽和又は不飽和炭化水素基、含酸素基（アルコキシ、エステル等）、含窒素基（シアノ、アジド等）、ハロゲン（例えば、フッ素、塩素、臭素、ヨウ素）等が挙げられるが、より好ましくは、炭化水素基、含酸素置換基、ハロゲンである。これらの置換基が炭素を含む場合、例えば、炭素を１～５個有するもの、又は炭素を１～３個有するものを好適に使用できる。λ３－ヨーダンの具体例には、［ビス（トリフルオロアセトキシ）ヨード］ベンゼン（ＰＩＦＡ）、［ヒドロキシ（トシルオキシ）ヨード］ベンゼン（ＨＴＩＢ）、（ジアセトキシヨード）ベンゼン（ＰＩＤＡ）、［ビス（トリフルオロアセトキシ）ヨード］ペンタフルオロベンゼン、及び［ヒドロキシ（メタンスルホニルオキシ）ヨード］ベンゼンが挙げられるが、これに限定されるものではない。
一実施形態において、λ３－ヨーダンは、式Ｒ４－Ｉ（ＯＲ５）２で表される化合物である（式中、Ｒ４は、無置換又は置換フェニル基であり、Ｒ５は、Ｈ、アセチル、トリフルオロアセチル、トシル、メタンスルホニル、及びこれらの組み合わせからなる群から選択される）。上記式の定義の通り、Ｒ４は「置換フェニル基」であってもよく、当該置換基としては、例えば、直鎖若しくは分枝状飽和又は不飽和炭化水素基、含酸素基（アルコキシ、エステル等）、含窒素基（シアノ、アジド等）、ハロゲン（例えば、フッ素、塩素、臭素、ヨウ素）等が挙げられるが、より好ましくは、炭化水素基、含酸素置換基、ハロゲンである。これらの置換基が炭素を含む場合、例えば、炭素を１～５個有するもの、又は炭素を１～３個有するものを好適に使用できる。λ３－ヨーダンの具体例には、［ビス（トリフルオロアセトキシ）ヨード］ベンゼン（ＰＩＦＡ）、［ヒドロキシ（トシルオキシ）ヨード］ベンゼン（ＨＴＩＢ）、（ジアセトキシヨード）ベンゼン（ＰＩＤＡ）、［ビス（トリフルオロアセトキシ）ヨード］ペンタフルオロベンゼン、及び［ヒドロキシ（メタンスルホニルオキシ）ヨード］ベンゼンが挙げられるが、これに限定されるものではない。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021040164 | 2021-03-12 | ||
| PCT/JP2022/010851 WO2022191313A1 (ja) | 2021-03-12 | 2022-03-11 | 糖鎖及び糖鎖を含む医薬品の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPWO2022191313A1 JPWO2022191313A1 (ja) | 2022-09-15 |
| JPWO2022191313A5 true JPWO2022191313A5 (ja) | 2023-12-07 |
Family
ID=83228168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023505652A Pending JPWO2022191313A1 (ja) | 2021-03-12 | 2022-03-11 |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP4306546A1 (ja) |
| JP (1) | JPWO2022191313A1 (ja) |
| KR (1) | KR20230157983A (ja) |
| CN (1) | CN116917341A (ja) |
| BR (1) | BR112023017365A2 (ja) |
| CA (1) | CA3212691A1 (ja) |
| IL (1) | IL305816A (ja) |
| WO (1) | WO2022191313A1 (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024053574A1 (ja) * | 2022-09-09 | 2024-03-14 | 第一三共株式会社 | 新規なオリゴ糖、該オリゴ糖の製造中間体、及びそれらの製造方法 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL162181A (en) | 1988-12-28 | 2006-04-10 | Pdl Biopharma Inc | A method of producing humanized immunoglubulin, and polynucleotides encoding the same |
| JP4124480B2 (ja) | 1991-06-14 | 2008-07-23 | ジェネンテック・インコーポレーテッド | 免疫グロブリン変異体 |
| WO1996002255A1 (fr) | 1994-07-15 | 1996-02-01 | Taiyo Kagaku Co., Ltd. | Composition medicamenteuse contenant un derive d'acide sialique |
| US6235883B1 (en) | 1997-05-05 | 2001-05-22 | Abgenix, Inc. | Human monoclonal antibodies to epidermal growth factor receptor |
| WO2002092771A2 (en) | 2001-05-11 | 2002-11-21 | Ludwig Institute For Cancer Research | Specific binding proteins and uses thereof |
| MXPA05000403A (es) | 2002-07-15 | 2005-07-22 | Genentech Inc | Metodos para identificar tumores que responden al tratamiento con anticuerpos contra erbb2. |
| US7662387B2 (en) | 2003-02-20 | 2010-02-16 | Seattle Genetics | Anti-cd70 antibody-drug conjugates and their use for the treatment of cancer and immune disorders |
| ES2527961T3 (es) | 2005-09-26 | 2015-02-02 | Medarex, L.L.C. | Anticuerpos monoclonales humanos para CD70 |
| JP2009155353A (ja) * | 2006-03-30 | 2009-07-16 | Yokohama City Univ | 糖鎖化合物の製造方法 |
| EP2199390B1 (en) | 2007-08-30 | 2016-12-21 | Daiichi Sankyo Company, Limited | Anti-epha2 antibody |
| JP5566226B2 (ja) | 2009-09-03 | 2014-08-06 | 旭化成株式会社 | １１糖シアリルオリゴ糖ペプチドの製造方法 |
| US10851174B2 (en) * | 2011-03-03 | 2020-12-01 | University Of Maryland, Baltimore | Core fucosylated glycopeptides and glycoproteins: chemoenzymatic synthesis and uses thereof |
| US9938312B2 (en) * | 2011-03-25 | 2018-04-10 | University Of Georgia Research Foundation, Inc. | Compounds and methods for chemical and chemo-enzymatic synthesis of complex glycans |
| EP3632471A1 (en) | 2012-10-11 | 2020-04-08 | Daiichi Sankyo Company, Limited | Antibody-drug conjugate |
| TW201442721A (zh) * | 2013-01-23 | 2014-11-16 | Daiichi Sankyo Co Ltd | 糖鏈修飾心房利尿鈉肽 |
| TW201534613A (zh) | 2013-06-28 | 2015-09-16 | Daiichi Sankyo Co Ltd | 寡糖胜肽之純化方法 |
| WO2015080603A1 (en) * | 2013-11-28 | 2015-06-04 | Antony John Fairbanks | Glycoproteins |
| KR102535900B1 (ko) | 2013-12-25 | 2023-05-26 | 다이이찌 산쿄 가부시키가이샤 | 항 trop2 항체-약물 컨쥬게이트 |
| US11559581B2 (en) | 2015-01-09 | 2023-01-24 | Oxford University Innovation Limited | Antibody conjugates and methods of making the antibody conjugates |
| WO2017110984A1 (ja) | 2015-12-25 | 2017-06-29 | 第一三共株式会社 | 限外ろ過膜を用いたオリゴ糖ペプチドの精製法 |
| EP4159749A3 (en) | 2016-07-01 | 2023-06-14 | Daiichi Sankyo Company, Limited | A method for producing fc-containing molecule with remodeled sugar chain |
| JP6342968B2 (ja) * | 2016-07-25 | 2018-06-13 | 株式会社伏見製薬所 | 糖誘導体の製造方法及び新規糖誘導体 |
| TW202330036A (zh) | 2017-05-15 | 2023-08-01 | 日商第一三共股份有限公司 | 抗體-藥物結合物之製造方法 |
| CN116999573A (zh) | 2017-09-29 | 2023-11-07 | 第一三共株式会社 | 抗体－药物偶联物及其制造方法、药物组合物及其在制备治疗肿瘤的药物中的应用 |
| AU2019337051B2 (en) | 2018-09-06 | 2023-11-23 | Daiichi Sankyo Company, Limited | Novel cyclic dinucleotide derivative and antibody-drug conjugate thereof |
-
2022
- 2022-03-11 WO PCT/JP2022/010851 patent/WO2022191313A1/ja active Application Filing
- 2022-03-11 JP JP2023505652A patent/JPWO2022191313A1/ja active Pending
- 2022-03-11 BR BR112023017365A patent/BR112023017365A2/pt unknown
- 2022-03-11 IL IL305816A patent/IL305816A/en unknown
- 2022-03-11 EP EP22767267.2A patent/EP4306546A1/en active Pending
- 2022-03-11 KR KR1020237032327A patent/KR20230157983A/ko unknown
- 2022-03-11 CA CA3212691A patent/CA3212691A1/en active Pending
- 2022-03-11 CN CN202280019248.5A patent/CN116917341A/zh active Pending
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