DE3742885C2 - - Google Patents
Info
- Publication number
- DE3742885C2 DE3742885C2 DE3742885A DE3742885A DE3742885C2 DE 3742885 C2 DE3742885 C2 DE 3742885C2 DE 3742885 A DE3742885 A DE 3742885A DE 3742885 A DE3742885 A DE 3742885A DE 3742885 C2 DE3742885 C2 DE 3742885C2
- Authority
- DE
- Germany
- Prior art keywords
- trans
- alkyl
- compounds
- dioxaborinane
- pentyl
- 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.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000002178 crystalline material Substances 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 20
- -1 4,3-disubstituted phenyl Chemical group 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 3
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 2
- HYYFAYFMSHAWFA-UHFFFAOYSA-N 2-cyclohexylethylbenzene Chemical compound C1CCCCC1CCC1=CC=CC=C1 HYYFAYFMSHAWFA-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001559 benzoic acids Chemical class 0.000 claims description 2
- 150000002012 dioxanes Chemical class 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- RHYUFGNCUXTFTC-UHFFFAOYSA-N 2-pentylpropane-1,3-diol Chemical compound CCCCCC(CO)CO RHYUFGNCUXTFTC-UHFFFAOYSA-N 0.000 description 5
- BALGERHMIXFENA-UHFFFAOYSA-N 4-butylcyclohexane-1-carboxylic acid Chemical compound CCCCC1CCC(C(O)=O)CC1 BALGERHMIXFENA-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IIYLSBVANMOTIK-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 2-fluoro-4-(5-pentyl-1,3,2-dioxaborinan-2-yl)benzoate Chemical compound O1CC(CCCCC)COB1C(C=C1F)=CC=C1C(=O)OC1=CC=C(C#N)C(F)=C1 IIYLSBVANMOTIK-UHFFFAOYSA-N 0.000 description 4
- ZLOKKDVYGFNBEL-UHFFFAOYSA-N 2-(3-chloro-4-pentoxyphenyl)-5-pentyl-1,3,2-dioxaborinane Chemical compound C1=C(Cl)C(OCCCCC)=CC=C1B1OCC(CCCCC)CO1 ZLOKKDVYGFNBEL-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RPAFHGIXEZRALN-UHFFFAOYSA-N 1-hexoxy-4-(4-hexoxyphenoxy)benzene Chemical compound CCCCCCOC1=CC=C(OC2=CC=C(OCCCCCC)C=C2)C=C1 RPAFHGIXEZRALN-UHFFFAOYSA-N 0.000 description 3
- OXBRRUNAAVNTOZ-SHTZXODSSA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(OCC)C=C1 OXBRRUNAAVNTOZ-SHTZXODSSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- KALFEOSSQJOUJL-UHFFFAOYSA-N 1-ethoxy-4-(4-ethoxyphenoxy)benzene Chemical compound C1=CC(OCC)=CC=C1OC1=CC=C(OCC)C=C1 KALFEOSSQJOUJL-UHFFFAOYSA-N 0.000 description 2
- YXPKKZZEUFHAOH-UHFFFAOYSA-N 2-fluoro-4-(5-pentyl-1,3,2-dioxaborinan-2-yl)benzoic acid Chemical compound O1CC(CCCCC)COB1C1=CC=C(C(O)=O)C(F)=C1 YXPKKZZEUFHAOH-UHFFFAOYSA-N 0.000 description 2
- DFVQUVQOQMLSKN-UHFFFAOYSA-N 4-boronooxy-2-fluorobenzoic acid Chemical compound OB(O)OC1=CC=C(C(O)=O)C(F)=C1 DFVQUVQOQMLSKN-UHFFFAOYSA-N 0.000 description 2
- JFKUBRAOUZEZSL-UHFFFAOYSA-N 4-butylbenzoic acid Chemical compound CCCCC1=CC=C(C(O)=O)C=C1 JFKUBRAOUZEZSL-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- CJEXGBVJRKOENG-UHFFFAOYSA-N (3-chloro-4-pentoxyphenoxy)boronic acid Chemical compound CCCCCOC1=CC=C(OB(O)O)C=C1Cl CJEXGBVJRKOENG-UHFFFAOYSA-N 0.000 description 1
- ZPRPKPQAJSQYTP-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 2-fluoro-4-(5-propyl-1,3,2-dioxaborinan-2-yl)benzoate Chemical compound CCCC1COB(OC1)c1ccc(C(=O)Oc2ccc(C#N)c(F)c2)c(F)c1 ZPRPKPQAJSQYTP-UHFFFAOYSA-N 0.000 description 1
- WUYQAYADHXKJTF-UHFFFAOYSA-N 1,3,2-dioxaborinane Chemical class B1OCCCO1 WUYQAYADHXKJTF-UHFFFAOYSA-N 0.000 description 1
- 150000000093 1,3-dioxanes Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-MICDWDOJSA-N 1-deuteriopropan-2-one Chemical compound [2H]CC(C)=O CSCPPACGZOOCGX-MICDWDOJSA-N 0.000 description 1
- RPCWEDINRIUTBL-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyphenoxy)benzene Chemical compound CCOC1=CC=CC=C1OC1=CC=CC=C1OCC RPCWEDINRIUTBL-UHFFFAOYSA-N 0.000 description 1
- PECOCCKIJGRFJA-UHFFFAOYSA-N 2-(4-ethoxy-3-fluorophenyl)-5-pentyl-1,3,2-dioxaborinane Chemical compound O1CC(CCCCC)COB1C1=CC=C(OCC)C(F)=C1 PECOCCKIJGRFJA-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- DFNDDQBYDLWGBI-UHFFFAOYSA-N 2-fluoro-4-(5-pentyl-1,3,2-dioxaborinan-2-yl)benzonitrile Chemical compound O1CC(CCCCC)COB1C1=CC=C(C#N)C(F)=C1 DFNDDQBYDLWGBI-UHFFFAOYSA-N 0.000 description 1
- REIVHYDACHXPNH-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(F)=C1 REIVHYDACHXPNH-UHFFFAOYSA-N 0.000 description 1
- YAPSUWCDOAOEAL-UHFFFAOYSA-N 2-fluoro-6-(5-propyl-1,3,2-dioxaborinan-2-yl)benzonitrile Chemical compound C(#N)C1=C(C=CC=C1F)B1OCC(CO1)CCC YAPSUWCDOAOEAL-UHFFFAOYSA-N 0.000 description 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- MDXOASINEVOWCV-UHFFFAOYSA-N 5-butyl-2,5-dimethoxycyclohexa-1,3-diene Chemical compound CCCCC1(OC)CC=C(OC)C=C1 MDXOASINEVOWCV-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- IZCCPCZSDWVYBF-UHFFFAOYSA-N C(CCC)C1(CC=C(C=C1)[N+]([O-])=NC1=C(C=CC=C1)C(=O)O)CCCCCC Chemical compound C(CCC)C1(CC=C(C=C1)[N+]([O-])=NC1=C(C=CC=C1)C(=O)O)CCCCCC IZCCPCZSDWVYBF-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
- C09K19/404—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing boron or phosphorus
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU4162762 RU1839171C (ru) | 1986-12-17 | 1986-12-17 | 2-[4-(4-Циано-3-галогенфенилоксикарбонил)-3-галогенфенил]-5-алкил-1,3,2-диоксаборинаны в качестве компонентов жидкокристаллических композиций |
| SU864162761A SU1766922A1 (ru) | 1986-12-17 | 1986-12-17 | 2-(4-Карбокси-3-галогенфенил)-5-алкил-1,3,2-диоксаборинаны в качестве полупродуктов синтеза жидкокристаллических производных галогенфенил-5-алкил-1,3,2-диоксаборинанов |
| SU4206875 | 1987-03-17 | ||
| SU4206874 | 1987-03-17 | ||
| SU4206873 | 1987-03-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3742885A1 DE3742885A1 (de) | 1988-08-18 |
| DE3742885C2 true DE3742885C2 (en, 2012) | 1990-09-06 |
Family
ID=27532838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19873742885 Granted DE3742885A1 (de) | 1986-12-17 | 1987-12-17 | 2-(4,3-disubstituiertes phenyl)-5-alkyl-1,3,2-dioxaborinanderivate und fluessigkristallines material |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4853150A (en, 2012) |
| CN (1) | CN87108378A (en, 2012) |
| CH (1) | CH671400A5 (en, 2012) |
| DE (1) | DE3742885A1 (en, 2012) |
| FR (1) | FR2608608B1 (en, 2012) |
| GB (1) | GB2201150B (en, 2012) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4014488A1 (de) * | 1990-05-07 | 1991-11-14 | Merck Patent Gmbh | Dioxaborinane und fluessigkristallines medium |
| GB9220189D0 (en) * | 1992-09-24 | 1992-11-04 | Central Research Lab Ltd | Dioxane derivatives |
| US6939985B1 (en) | 1997-04-09 | 2005-09-06 | Commonwealth Scientific And Industrial Research Organisation | Aryl borates |
| JP2002505663A (ja) * | 1997-04-09 | 2002-02-19 | コモンウエルス サイエンティフィック アンド インダストリアル リサーチ オーガナイゼーション | アリールホウ酸エステル |
| KR100544104B1 (ko) * | 1998-05-26 | 2006-03-23 | 삼성에스디아이 주식회사 | 네마틱 액정조성물 및 이를 이용한 액정표시소자 |
| KR100544105B1 (ko) * | 1998-05-26 | 2006-03-24 | 삼성에스디아이 주식회사 | 네마틱 액정조성물 및 이를 이용한 액정표시소자 |
| KR100553727B1 (ko) * | 1998-12-03 | 2006-06-20 | 삼성에스디아이 주식회사 | 새로운 디옥사보리난 유도체 및 이를 포함하는 액정조성물 |
| WO2006053628A1 (en) * | 2004-11-20 | 2006-05-26 | Merck Patent Gmbh | Liquid crystal compounds, liquid crystal medium and liquid crystal display |
| JO3598B1 (ar) | 2006-10-10 | 2020-07-05 | Infinity Discovery Inc | الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني |
| WO2009126691A1 (en) * | 2008-04-09 | 2009-10-15 | Infinity Pharmaceuticals, Inc | Inhibitors of fatty acid amide hydrolase |
| AU2010234449A1 (en) | 2009-04-07 | 2011-11-03 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| AU2010234445A1 (en) | 2009-04-07 | 2011-11-03 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| MX336742B (es) | 2010-02-03 | 2016-01-29 | Infinity Pharmaceuticals Inc | Inhibidores de amida hidrolasa de acido graso. |
| CN103666482B (zh) * | 2012-09-10 | 2016-05-25 | 苏州汉朗光电有限公司 | 一种近晶a相液晶材料 |
| WO2017066211A1 (en) | 2015-10-12 | 2017-04-20 | Advanced Cell Diagnostics, Inc. | In situ detection of nucleotide variants in high noise samples, and compositions and methods related thereto |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3038926A (en) * | 1958-09-17 | 1962-06-12 | Roussel Uclaf | Organic diol aryl boronates |
| JPS6183190A (ja) * | 1984-09-29 | 1986-04-26 | Nitto Kasei Kk | ２−（４′−置換フエニル）−５−アルキル−１，３，２−ジオキサボリナン化合物，その製造法及びそれを含有する液晶組成物 |
| JPS6197293A (ja) * | 1984-10-18 | 1986-05-15 | Nitto Kasei Kk | ２−（４′−置換フエニル）−５−（４″−置換フエニル）−１，３，２−ジオキサボリナン化合物，その製造法及びそれを含有する液晶組成物 |
| JPS61109792A (ja) * | 1984-11-01 | 1986-05-28 | Nitto Kasei Kk | ２−（４′−置換フエニル）−５−アルキル−１，３，２−ジオキサボリナン化合物，その製造法及びそれを含有する液晶組成物 |
| JPS61233689A (ja) * | 1985-03-22 | 1986-10-17 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 複素環式ホウ素化合物 |
| DE3608714A1 (de) * | 1985-03-22 | 1986-09-25 | Merck Patent Gmbh, 6100 Darmstadt | Borheterocyclen |
| JP3247453B2 (ja) * | 1992-09-29 | 2002-01-15 | 大日本印刷株式会社 | 集積回路マスクパターンからの回路接続情報抽出方法 |
| JP3204277B2 (ja) * | 1992-12-22 | 2001-09-04 | 共同印刷株式会社 | Ｉｃカードの製造方法およびｉｃカード |
| JPH06197293A (ja) * | 1992-12-25 | 1994-07-15 | Toshiba Corp | テレビジョンセットのスピーカシステム |
-
1987
- 1987-12-15 CH CH4887/87A patent/CH671400A5/de not_active IP Right Cessation
- 1987-12-15 GB GB8729239A patent/GB2201150B/en not_active Expired - Fee Related
- 1987-12-16 US US07/133,635 patent/US4853150A/en not_active Expired - Lifetime
- 1987-12-16 FR FR878717599A patent/FR2608608B1/fr not_active Expired - Fee Related
- 1987-12-17 DE DE19873742885 patent/DE3742885A1/de active Granted
- 1987-12-17 CN CN198787108378A patent/CN87108378A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH671400A5 (en, 2012) | 1989-08-31 |
| FR2608608A1 (fr) | 1988-06-24 |
| FR2608608B1 (fr) | 1991-08-16 |
| GB2201150A (en) | 1988-08-24 |
| CN87108378A (zh) | 1988-09-07 |
| DE3742885A1 (de) | 1988-08-18 |
| GB8729239D0 (en) | 1988-01-27 |
| US4853150A (en) | 1989-08-01 |
| GB2201150B (en) | 1991-04-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |