JP5930930B2 - メチレンジスルホニルクロライド化合物、メチレンジスルホン酸化合物およびメチレンジスルホネート化合物の製造方法 - Google Patents
メチレンジスルホニルクロライド化合物、メチレンジスルホン酸化合物およびメチレンジスルホネート化合物の製造方法 Download PDFInfo
- Publication number
- JP5930930B2 JP5930930B2 JP2012209286A JP2012209286A JP5930930B2 JP 5930930 B2 JP5930930 B2 JP 5930930B2 JP 2012209286 A JP2012209286 A JP 2012209286A JP 2012209286 A JP2012209286 A JP 2012209286A JP 5930930 B2 JP5930930 B2 JP 5930930B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- methylene
- compound
- compound represented
- group
- 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.)
- Active
Links
- -1 methylene disulfonic acid compound Chemical class 0.000 title claims description 61
- DKZQZHQHDMVGHE-UHFFFAOYSA-N methanedisulfonyl chloride Chemical compound ClS(=O)(=O)CS(Cl)(=O)=O DKZQZHQHDMVGHE-UHFFFAOYSA-N 0.000 title claims description 48
- 238000004519 manufacturing process Methods 0.000 title claims description 31
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 73
- 238000000034 method Methods 0.000 claims description 40
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 28
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 28
- 239000003495 polar organic solvent Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 238000002156 mixing Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000012024 dehydrating agents Substances 0.000 claims description 10
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 8
- 229920002866 paraformaldehyde Polymers 0.000 claims description 8
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 6
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 description 37
- 239000000243 solution Substances 0.000 description 17
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 16
- XHYXFOFSQYUYBT-UHFFFAOYSA-N ethane-1,1-disulfonyl chloride Chemical compound ClS(=O)(=O)C(C)S(Cl)(=O)=O XHYXFOFSQYUYBT-UHFFFAOYSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 235000019260 propionic acid Nutrition 0.000 description 8
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical class OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 6
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- DBNBYVDVUHEYAX-UHFFFAOYSA-N ethane-1,1-disulfonate;hydron Chemical compound OS(=O)(=O)C(C)S(O)(=O)=O DBNBYVDVUHEYAX-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JYAFNQRVSBTHSN-UHFFFAOYSA-N prop-2-ene-1,2-disulfonic acid Chemical compound OS(=O)(=O)CC(=C)S(O)(=O)=O JYAFNQRVSBTHSN-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- LQVXAITUEFEGIG-UHFFFAOYSA-N CC(C)(S(Cl)(=O)=O)S(Cl)(=O)=O Chemical compound CC(C)(S(Cl)(=O)=O)S(Cl)(=O)=O LQVXAITUEFEGIG-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-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
- 239000000654 additive Substances 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- PJSSUNXXDZHGOR-UHFFFAOYSA-N chlorosulfonyloxymethyl hypochlorite Chemical compound C(OCl)OS(=O)(=O)Cl PJSSUNXXDZHGOR-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000005499 phosphonyl group Chemical group 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012209286A JP5930930B2 (ja) | 2012-09-24 | 2012-09-24 | メチレンジスルホニルクロライド化合物、メチレンジスルホン酸化合物およびメチレンジスルホネート化合物の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012209286A JP5930930B2 (ja) | 2012-09-24 | 2012-09-24 | メチレンジスルホニルクロライド化合物、メチレンジスルホン酸化合物およびメチレンジスルホネート化合物の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014062076A JP2014062076A (ja) | 2014-04-10 |
| JP2014062076A5 JP2014062076A5 (enrdf_load_stackoverflow) | 2015-10-15 |
| JP5930930B2 true JP5930930B2 (ja) | 2016-06-08 |
Family
ID=50617672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012209286A Active JP5930930B2 (ja) | 2012-09-24 | 2012-09-24 | メチレンジスルホニルクロライド化合物、メチレンジスルホン酸化合物およびメチレンジスルホネート化合物の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP5930930B2 (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015064712A1 (ja) * | 2013-10-30 | 2015-05-07 | 住友精化株式会社 | メチレンジスルホン酸化合物の製造方法 |
| WO2015064711A1 (ja) * | 2013-10-30 | 2015-05-07 | 住友精化株式会社 | メチレンジスルホニルクロライド化合物の製造方法 |
| PL3353157T3 (pl) | 2015-09-25 | 2022-02-14 | Carnegie Mellon University | Katalizatory utleniania na bazie związków makrocyklicznych |
| CN109988085B (zh) * | 2017-12-29 | 2021-11-09 | 张家港市国泰华荣化工新材料有限公司 | 金属离子含量低的1,3-丙二烷基磺酸的制备方法 |
| CN109053501A (zh) * | 2018-09-19 | 2018-12-21 | 长园华盛(泰兴)锂电材料有限公司 | 一种甲基二磺酸除水方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4588407B2 (ja) * | 2004-04-28 | 2010-12-01 | 住友化学株式会社 | 環式ジスルホン酸エステルの製造方法 |
| JP2006188449A (ja) * | 2005-01-05 | 2006-07-20 | Sumitomo Chemical Co Ltd | 環式ジスルホン酸エステルの製造方法 |
| JP4577499B2 (ja) * | 2005-01-28 | 2010-11-10 | 日本電気株式会社 | メチレンジスルホニルクロライド及びその誘導体の製造方法 |
| TWI410413B (zh) * | 2006-04-26 | 2013-10-01 | Sumitomo Seika Chemicals | Preparation method of methylene disulfonate compound |
| JP5724366B2 (ja) * | 2010-12-21 | 2015-05-27 | セントラル硝子株式会社 | 環状ジスルホン酸エステル化合物の製造方法 |
-
2012
- 2012-09-24 JP JP2012209286A patent/JP5930930B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2014062076A (ja) | 2014-04-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zafrani et al. | Diethyl bromodifluoromethylphosphonate: a highly efficient and environmentally benign difluorocarbene precursor | |
| JP5930930B2 (ja) | メチレンジスルホニルクロライド化合物、メチレンジスルホン酸化合物およびメチレンジスルホネート化合物の製造方法 | |
| TWI508956B (zh) | Preparation method of methylene disulfonate compound | |
| JP6574209B2 (ja) | ２−ハロゲン−アクリル酸エステルを製造するための方法 | |
| JP2014201545A (ja) | ２−ヒドロキシメチル−２，３−ジヒドロ−チエノ［３，４−ｂ］［１，４］ジオキシン−５，７−ジカルボン酸ジアルキルエステルの製造方法 | |
| WO2015064712A1 (ja) | メチレンジスルホン酸化合物の製造方法 | |
| EP1723156A1 (en) | Process for the preparation of pyridine derivatives | |
| JP2007145815A (ja) | トリフルオロメタンスルホン酸無水物の製造方法。 | |
| KR101135088B1 (ko) | 1,3-프로펜설톤의 제조방법 | |
| US6844450B2 (en) | Process for the production of a racemic thioctic acid | |
| JP2005536558A (ja) | ナプロキセンのニトロオキシ誘導体の製造法 | |
| JP2019147829A (ja) | ５−（トリフルオロメチル）ピリミジン誘導体及びその製造方法 | |
| JP2009518380A (ja) | ２−クロロエトキシ−酢酸−ｎ，ｎ−ジメチルアミドの製法 | |
| JP6231262B2 (ja) | ピタバスタチンカルシウムの前駆体の製造法 | |
| JP5186115B2 (ja) | ２‐置換ベンジル‐３，３‐ジフルオロアクリル酸エステル誘導体及びそれらの製造方法 | |
| JP5482233B2 (ja) | ジアリールジスルフィド化合物の製造方法 | |
| WO2015064711A1 (ja) | メチレンジスルホニルクロライド化合物の製造方法 | |
| JP5268264B2 (ja) | アルカンジスルホニルハライドの製造方法 | |
| EP1739071B1 (en) | Method for producing carboxylic acid compound | |
| JP5205971B2 (ja) | テトラヒドロピラン化合物の製造方法 | |
| JP6771775B2 (ja) | ２−アミノニコチン酸ベンジルエステル誘導体の製造方法 | |
| JPS6244541B2 (enrdf_load_stackoverflow) | ||
| JP4171965B2 (ja) | ４，４−ジフルオロ−３−ブテン−１−オール誘導体の製造法 | |
| JPH0318617B2 (enrdf_load_stackoverflow) | ||
| WO2005058918A1 (fr) | Nouveaux derives d’acides phenyl-boronique et leurs procedes de preparation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150826 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150826 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20160323 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160405 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160426 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5930930 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |