JP2013523881A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013523881A5 JP2013523881A5 JP2013504935A JP2013504935A JP2013523881A5 JP 2013523881 A5 JP2013523881 A5 JP 2013523881A5 JP 2013504935 A JP2013504935 A JP 2013504935A JP 2013504935 A JP2013504935 A JP 2013504935A JP 2013523881 A5 JP2013523881 A5 JP 2013523881A5
- Authority
- JP
- Japan
- Prior art keywords
- acrylic acid
- isocyanato
- ester
- methyl
- propyl
- 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
Links
- 238000000034 method Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical group C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- -1 amine compound Chemical class 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- ORTCGSWQDZPULK-UHFFFAOYSA-N 3-isocyanatopropyl prop-2-enoate Chemical compound C=CC(=O)OCCCN=C=O ORTCGSWQDZPULK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RSVLLJMCLGUKLM-UHFFFAOYSA-N 10-isocyanatodecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCN=C=O RSVLLJMCLGUKLM-UHFFFAOYSA-N 0.000 description 1
- QXOJEFDVHQCJNH-UHFFFAOYSA-N 10-isocyanatodecyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCCN=C=O QXOJEFDVHQCJNH-UHFFFAOYSA-N 0.000 description 1
- YIZNDHIAODOIBD-UHFFFAOYSA-N 11-isocyanatoundecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCCN=C=O YIZNDHIAODOIBD-UHFFFAOYSA-N 0.000 description 1
- WEOHWYYCMGEAQY-UHFFFAOYSA-N 12-isocyanatododecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCCCN=C=O WEOHWYYCMGEAQY-UHFFFAOYSA-N 0.000 description 1
- FLBILZJKOCDIBX-UHFFFAOYSA-N 12-isocyanatododecyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCCCCN=C=O FLBILZJKOCDIBX-UHFFFAOYSA-N 0.000 description 1
- XATIYOQSKWPDFU-UHFFFAOYSA-N 2,3-diisocyanatopropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(N=C=O)CN=C=O XATIYOQSKWPDFU-UHFFFAOYSA-N 0.000 description 1
- ZNDYQROPOVNRSL-UHFFFAOYSA-N 2,3-diisocyanatopropyl prop-2-enoate Chemical compound C=CC(=O)OCC(N=C=O)CN=C=O ZNDYQROPOVNRSL-UHFFFAOYSA-N 0.000 description 1
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical group C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 description 1
- HSSLFJICBPDMPH-UHFFFAOYSA-N 2-isocyanatopropyl 2-methylprop-2-enoate Chemical compound O=C=NC(C)COC(=O)C(C)=C HSSLFJICBPDMPH-UHFFFAOYSA-N 0.000 description 1
- RGDAQLOWLCIMDP-UHFFFAOYSA-N 2-isocyanatopropyl prop-2-enoate Chemical compound O=C=NC(C)COC(=O)C=C RGDAQLOWLCIMDP-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- OTKLRHWBZHQJOP-UHFFFAOYSA-N 3-aminopropyl prop-2-enoate Chemical compound NCCCOC(=O)C=C OTKLRHWBZHQJOP-UHFFFAOYSA-N 0.000 description 1
- HVQPNKXSWMVRDZ-UHFFFAOYSA-N 3-isocyanatopropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCN=C=O HVQPNKXSWMVRDZ-UHFFFAOYSA-N 0.000 description 1
- FPMYOMFDJKFHBV-UHFFFAOYSA-N 4-isocyanatobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCN=C=O FPMYOMFDJKFHBV-UHFFFAOYSA-N 0.000 description 1
- OQEAEWQOPZQPSS-UHFFFAOYSA-N 4-isocyanatobutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCN=C=O OQEAEWQOPZQPSS-UHFFFAOYSA-N 0.000 description 1
- ISDYQNBADWDQAB-UHFFFAOYSA-N 6-isocyanatohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCN=C=O ISDYQNBADWDQAB-UHFFFAOYSA-N 0.000 description 1
- XJRMEBKVZKZQGM-UHFFFAOYSA-N 6-isocyanatohexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCN=C=O XJRMEBKVZKZQGM-UHFFFAOYSA-N 0.000 description 1
- ICIZZFOJFCBJLO-UHFFFAOYSA-N 8-isocyanatooctyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCN=C=O ICIZZFOJFCBJLO-UHFFFAOYSA-N 0.000 description 1
- KECRGISUZXMERG-UHFFFAOYSA-N 8-isocyanatooctyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCN=C=O KECRGISUZXMERG-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- DLXDBOZVVLOXPE-UHFFFAOYSA-N C=CC(=O)OCCCCCCCCCCCN=C=O Chemical compound C=CC(=O)OCCCCCCCCCCCN=C=O DLXDBOZVVLOXPE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YHNUDLCUIKMNSN-UHFFFAOYSA-N bis(1,2,4-triazol-1-yl)methanone Chemical compound C1=NC=NN1C(=O)N1C=NC=N1 YHNUDLCUIKMNSN-UHFFFAOYSA-N 0.000 description 1
- GOQHBKGRSKXWLY-UHFFFAOYSA-N bis(benzimidazol-1-yl)methanone Chemical compound C1=NC2=CC=CC=C2N1C(=O)N1C2=CC=CC=C2N=C1 GOQHBKGRSKXWLY-UHFFFAOYSA-N 0.000 description 1
- ZXYBIPTYOWWVQD-UHFFFAOYSA-N bis(benzotriazol-1-yl)methanone Chemical compound N1=NC2=CC=CC=C2N1C(=O)N1C2=CC=CC=C2N=N1 ZXYBIPTYOWWVQD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10159888.6 | 2010-04-14 | ||
| EP10159888A EP2377847A1 (en) | 2010-04-14 | 2010-04-14 | Process for producing isocyanates |
| PCT/US2011/031061 WO2011130032A1 (en) | 2010-04-14 | 2011-04-04 | Process for producing isocyanates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013523881A JP2013523881A (ja) | 2013-06-17 |
| JP2013523881A5 true JP2013523881A5 (https=) | 2014-05-15 |
| JP5960680B2 JP5960680B2 (ja) | 2016-08-02 |
Family
ID=42635226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013504935A Expired - Fee Related JP5960680B2 (ja) | 2010-04-14 | 2011-04-04 | イソシアネートの製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9006480B2 (https=) |
| EP (2) | EP2377847A1 (https=) |
| JP (1) | JP5960680B2 (https=) |
| CN (1) | CN102844297B (https=) |
| WO (1) | WO2011130032A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6025476B2 (ja) * | 2012-09-21 | 2016-11-16 | 昭和電工株式会社 | エチレン性不飽和基含有イソシアネート化合物の製造方法 |
| CN103193675A (zh) * | 2013-03-26 | 2013-07-10 | 浙江同丰医药化工有限公司 | 一种甲基丙烯酸乙酯异氰酸酯的制备方法 |
| CN105377911B (zh) * | 2013-07-25 | 2017-05-24 | 昭和电工株式会社 | 组合物、固化性组合物、其制造方法及固化物 |
| WO2015016330A1 (ja) * | 2013-08-02 | 2015-02-05 | ダイキン工業株式会社 | 不飽和基を有する新規化合物及びこの化合物を含む組成物 |
| JP5737466B1 (ja) | 2013-08-02 | 2015-06-17 | ダイキン工業株式会社 | 重合性官能基及び架橋性官能基からなる群より選択される少なくとも１種の基を含有する含フッ素重合体を含む組成物及び塗装物品 |
| US9266824B2 (en) | 2014-01-13 | 2016-02-23 | Warsaw Orthopedic, Inc. | Methods and compositions for making an amino acid triisocyanate |
| RU2694833C2 (ru) | 2015-02-04 | 2019-07-17 | Мицубиси Газ Кемикал Компани, Инк. | Способ получения гидрохлорида 2-аминоэтилметакрилата |
| FR3034769A1 (fr) | 2015-04-07 | 2016-10-14 | Michelin & Cie | Procede de synthese d'un copolymere portant des groupes pendants imidazole |
| TW201829525A (zh) | 2016-10-14 | 2018-08-16 | 日商旭化成股份有限公司 | 異氰酸酯組成物，異氰酸酯聚合物之製造方法，以及異氰酸酯聚合物 |
| KR102821473B1 (ko) * | 2020-01-06 | 2025-06-18 | 가부시끼가이샤 레조낙 | 이소시아나토기를 갖는 (메트)아크릴산에스테르 화합물 및 그 제조 방법 |
| CN116621736B (zh) * | 2023-05-18 | 2024-07-19 | 瑞博(杭州)医药科技有限公司 | 一种异氰酸酯类化合物的制备方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2718516A (en) | 1952-11-08 | 1955-09-20 | Rohm & Haas | Isocyanato esters of acrylic, methacrylic, and crotonic acids |
| US2821544A (en) | 1954-04-26 | 1958-01-28 | Bayer Ag | Production of alkylisocyanate esters of 2-alkenoic acids |
| US4176232A (en) | 1968-06-27 | 1979-11-27 | Rohm And Haas Company | Sulfonic acid salts of acyloxyalkylamines |
| US4395569A (en) | 1968-06-27 | 1983-07-26 | Rohm And Haas Company | Method of preparing sulfonic acid salts of acyloxyalkylamines and polymers and compounds therefrom |
| US4278809A (en) | 1977-06-15 | 1981-07-14 | The Dow Chemical Company | Process for preparing 2-isocyanatoalkyl esters of organic carboxylic acids |
| EP0202840B1 (en) | 1985-05-13 | 1991-08-21 | Nippon Paint Co., Ltd. | Isocyanate compounds and their production |
| JPS649112A (en) | 1987-06-24 | 1989-01-12 | Toray Eng Co Ltd | Spool packaging apparatus with plastic film |
| JPH01272570A (ja) * | 1988-04-26 | 1989-10-31 | Nippon Shokubai Kagaku Kogyo Co Ltd | ４−メチル−５−［（２−アミノエチル）−チオメチル］−イミダゾールの製法 |
| JP2632977B2 (ja) | 1988-11-10 | 1997-07-23 | 昭和電工株式会社 | 不飽和カルボン酸−２−イソシアナトアルキルエステルの製造方法 |
| JPH02145555A (ja) | 1988-11-29 | 1990-06-05 | Showa Roodeia Kagaku Kk | （メタ）アクリル酸イソシアナトアルキルエステルの重合防止法 |
| JP2632984B2 (ja) * | 1988-11-29 | 1997-07-23 | 昭和電工株式会社 | 不飽和カルボン酸イソシアナトアルキルエステルの製造法 |
| US5073440A (en) | 1989-06-05 | 1991-12-17 | E. I. Du Pont De Nemours And Company | Poly(vinyl pyrrolidone)/p-phenylene terephthalamide composite fibers (pvp/ppd-t) |
| EP0408277A2 (en) | 1989-07-12 | 1991-01-16 | Arco Chemical Technology, Inc. | Process for the preparation of aliphatic isocyanates |
| JP3091979B2 (ja) | 1991-09-03 | 2000-09-25 | 昭和電工株式会社 | 有機イソシアナートの精製法 |
| AT398762B (de) * | 1992-08-13 | 1995-01-25 | Chemie Linz Gmbh | Verfahren zur herstellung von isocyanaten durch zersetzung von n,n,n'-trisubstituierten harnstoffen |
| US5457229A (en) | 1994-02-09 | 1995-10-10 | University Of Ottawa | Process for preparing isocyanates from urethanes by a novel technique |
| EP0849258B1 (de) | 1996-12-19 | 2001-10-31 | Novartis AG | Verfahren zur Herstellung von ethylenisch ungesättigten Isocyanaten |
| JP4273531B2 (ja) | 1998-02-06 | 2009-06-03 | 昭和電工株式会社 | イソシアナトアルキル（メタ）アクリレートの製造方法 |
| DE602004031237D1 (de) * | 2003-07-31 | 2011-03-10 | Showa Denko Kk | Verfahren zur herstellung von hochreinem (meth)acryloyloxyalkylisocyanat |
| US7632965B2 (en) | 2004-03-25 | 2009-12-15 | Showa Denko K.K. | Method for producing (meth)acrylate derivative having isocyanate group |
| KR100891790B1 (ko) * | 2004-10-29 | 2009-04-07 | 쇼와 덴코 가부시키가이샤 | 블록 이소시아네이트 화합물의 제조 방법 |
| EP1780213A1 (en) * | 2005-10-27 | 2007-05-02 | 3M Innovative Properties Company | Silicon-urea-azolides, their preparation and use in the preparation of silicones with isocyanate terminal groups |
-
2010
- 2010-04-14 EP EP10159888A patent/EP2377847A1/en not_active Ceased
-
2011
- 2011-04-04 US US13/638,817 patent/US9006480B2/en active Active
- 2011-04-04 CN CN201180018459.9A patent/CN102844297B/zh not_active Expired - Fee Related
- 2011-04-04 JP JP2013504935A patent/JP5960680B2/ja not_active Expired - Fee Related
- 2011-04-04 EP EP11769294.7A patent/EP2558441B1/en not_active Not-in-force
- 2011-04-04 WO PCT/US2011/031061 patent/WO2011130032A1/en not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013523881A5 (https=) | ||
| JP6180705B2 (ja) | ハロゲン化環式化合物の合成方法 | |
| EP3218351B1 (en) | A method for the preparation, isolation and purification of pharmaceutically applicable forms of ahu-377 | |
| BR112019019605B1 (pt) | Compostos e processo para preparar um composto de fórmula ii-a | |
| AU2015371250B2 (en) | Process of making cenicriviroc and related analogs | |
| KR100917698B1 (ko) | 레트로졸의 제조를 위한 개선된 방법 | |
| US20170342038A1 (en) | A method for preparing gadobutrol | |
| US20190241511A1 (en) | Polymorphic forms of belinostat and processes for preparation thereof | |
| JP2024167399A (ja) | （５ｓ）－４－［５－（３，５－ジクロロフェニル）－５－（トリフルオロメチル）－４ｈ－イソオキサゾール－３－イル］－２－メチル－安息香酸の製造方法 | |
| EP3677572B1 (en) | Production method for pyrazole-4-carboxamide derivative | |
| EP2643306B1 (en) | Process for the preparation of deferasirox | |
| TW201217346A (en) | Process for preparing the crystalline form II of febuxostat | |
| US10787431B2 (en) | 4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-mercapto-1h-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile and processes of preparation | |
| WO2015087343A2 (en) | An improved process for the preparation of nilotinib and pharmaceutically acceptable salts thereof | |
| US6987185B2 (en) | Method for separating methyl 4-(2-chloro-4-fluorophenyl)-2-(3,5-difluoro-2-pyridinyl)-6-methyl-1,4-dihydro-5-pyrimidine-carboxylate-recemate | |
| JP2022514306A (ja) | （５ｓ）－４－［５－（３，５－ジクロロフェニル）－５－（トリフルオロメチル）－４ｈ－イソオキサゾール－３－イル］－２－メチル－安息香酸を製造する方法 | |
| JP6763401B2 (ja) | ベンズオキサゾール化合物の製造方法 | |
| JP2025518760A (ja) | ピコリンアミド殺真菌剤化合物の結晶形態 | |
| TWI643848B (zh) | 製備嘧啶中間物之方法 | |
| KR101811123B1 (ko) | 신규의 모르폴린 이인산염 및 이를 이용한 고순도 리바록사반의 제조방법 | |
| CZ2003524A3 (cs) | Katalytický způsob přípravy thiazolových derivátů | |
| WO2014103812A1 (ja) | ピラゾール化合物の結晶の製造方法 | |
| US20230033450A1 (en) | Method for preparing diazoxide | |
| US20110071302A1 (en) | Process for preparing intermediate compound for synthesizing an antiulcerant | |
| JP6389513B2 (ja) | ３−クロロ−４−メトキシベンジルアミン塩酸塩含有組成物およびその製造方法 |