SK287329B6 - Spôsob prípravy bis-benzazolylových zlúčenín - Google Patents

Spôsob prípravy bis-benzazolylových zlúčenín Download PDF

Info

Publication number: SK287329B6
Authority: SK; Slovakia
Prior art keywords: formula; carbon atoms; iii; process according; group
Prior art date: 2000-10-18

Application number

SK583-2003A

Other languages

English (en)

Slovak (sk)

Other versions

SK5832003A3 (en

Inventor

Victor Paul Eliu

Julia Hauser

Original Assignee

Ciba Specialty Chemicals Holding Inc.

Priority date (The priority date 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 date listed.)

2000-10-18

Filing date

2001-10-09

Publication date

2010-07-07

2001-10-09 Application filed by Ciba Specialty Chemicals Holding Inc. filed Critical Ciba Specialty Chemicals Holding Inc.

2003-10-07 Publication of SK5832003A3 publication Critical patent/SK5832003A3/sk

2010-07-07 Publication of SK287329B6 publication Critical patent/SK287329B6/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 35
238000000034 method Methods 0.000 title claims abstract description 24
238000002360 preparation method Methods 0.000 title claims abstract description 12
-1 C1-C10alkoxyl Chemical group 0.000 claims abstract description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
239000002904 solvent Substances 0.000 claims abstract description 10
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 9
239000011541 reaction mixture Substances 0.000 claims abstract description 8
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 6
150000002148 esters Chemical class 0.000 claims abstract description 6
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 16
239000004327 boric acid Substances 0.000 claims description 11
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
239000008096 xylene Substances 0.000 claims description 9
239000003377 acid catalyst Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000010936 titanium Substances 0.000 claims description 5
229910052719 titanium Inorganic materials 0.000 claims description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
150000003738 xylenes Chemical class 0.000 claims description 2
125000005619 boric acid group Chemical group 0.000 claims 1
239000007844 bleaching agent Substances 0.000 abstract description 2
239000003054 catalyst Substances 0.000 abstract description 2
229920002994 synthetic fiber Polymers 0.000 abstract description 2
229910052739 hydrogen Inorganic materials 0.000 abstract 3
239000001257 hydrogen Substances 0.000 abstract 3
150000002431 hydrogen Chemical class 0.000 abstract 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
230000002378 acidificating effect Effects 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical group 0.000 abstract 1
230000003287 optical effect Effects 0.000 abstract 1
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 12
238000003756 stirring Methods 0.000 description 8
239000000725 suspension Substances 0.000 description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
238000010521 absorption reaction Methods 0.000 description 7
230000008033 biological extinction Effects 0.000 description 7
239000007787 solid Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 2
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
YCGAZNXXGKTASZ-UHFFFAOYSA-N thiophene-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)S1 YCGAZNXXGKTASZ-UHFFFAOYSA-N 0.000 description 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
GNRPLFDNCZBMTQ-UHFFFAOYSA-N 2-[4-(chloromethyl)phenyl]-1h-indole Chemical class C1=CC(CCl)=CC=C1C1=CC2=CC=CC=C2N1 GNRPLFDNCZBMTQ-UHFFFAOYSA-N 0.000 description 1
RPJUVNYXHUCRMG-UHFFFAOYSA-N 2-amino-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N)=C1 RPJUVNYXHUCRMG-UHFFFAOYSA-N 0.000 description 1
ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
SBBQDUFLZGOASY-OWOJBTEDSA-N 4-[(e)-2-(4-carboxyphenyl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=C(C(O)=O)C=C1 SBBQDUFLZGOASY-OWOJBTEDSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XYRAGINUKPZXQY-UHFFFAOYSA-N C1=CC=C2SC=NC2=C1.C=1C=CC=C(C=2NC3=CC=CC=C3N=2)C=1C=CC1=CC=CC=C1 Chemical class C1=CC=C2SC=NC2=C1.C=1C=CC=C(C=2NC3=CC=CC=C3N=2)C=1C=CC1=CC=CC=C1 XYRAGINUKPZXQY-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
150000005829 chemical entities Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000006471 dimerization reaction Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000004987 o-phenylenediamines Chemical class 0.000 description 1
238000009994 optical bleaching Methods 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
WZMPOCLULGAHJR-UHFFFAOYSA-N thiophen-2-ol Chemical compound OC1=CC=CS1 WZMPOCLULGAHJR-UHFFFAOYSA-N 0.000 description 1
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
- C07D263/64—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings linked in positions 2 and 2' by chains containing six-membered aromatic rings or ring systems containing such rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

SK583-2003A 2000-10-18 2001-10-09 Spôsob prípravy bis-benzazolylových zlúčenín SK287329B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP00810961		2000-10-18
PCT/EP2001/011644 WO2002032886A1 (en)	2000-10-18	2001-10-09	A process for the preparation of bis-benzazolyl compounds

Publications (2)

Publication Number	Publication Date
SK5832003A3 SK5832003A3 (en)	2003-10-07
SK287329B6 true SK287329B6 (sk)	2010-07-07

Family

ID=8174976

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK583-2003A SK287329B6 (sk)	2000-10-18	2001-10-09	Spôsob prípravy bis-benzazolylových zlúčenín

Country Status (16)

Country	Link
US (2)	US20030191320A1 (de)
EP (1)	EP1326850B1 (de)
JP (1)	JP2004511551A (de)
KR (1)	KR100820119B1 (de)
CN (1)	CN1263748C (de)
AT (1)	ATE309992T1 (de)
AU (1)	AU2002215930A1 (de)
BR (1)	BR0114753A (de)
CA (1)	CA2425165C (de)
CZ (1)	CZ301894B6 (de)
DE (1)	DE60115080T2 (de)
ES (1)	ES2252320T3 (de)
MX (1)	MXPA03003140A (de)
RU (1)	RU2293084C2 (de)
SK (1)	SK287329B6 (de)
WO (1)	WO2002032886A1 (de)

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MY143758A (en) *	2004-09-13	2011-07-15	Ciba Holding Inc	Polyolefin articles
CN100412058C (zh) *	2005-05-12	2008-08-20	苏州大学	一种双吲哚烷基化合物的合成方法
CN1332948C (zh) *	2005-05-12	2007-08-22	苏州大学	双吲哚烷基衍生物的合成方法
US20090318593A1 (en) *	2005-09-28	2009-12-24	Klaus Stoll	Process for Improving the Flow Properties of Polymer Melts
WO2007039521A1 (en) *	2005-09-30	2007-04-12	Ciba Specialty Chemicals Holding Inc.	Microporous films
CN102070627A (zh) *	2010-12-29	2011-05-25	河北星宇化工有限公司	2,5－双(5－叔丁基2－苯并噁唑基)噻吩的制备方法
CN107141309A (zh)	2011-01-11	2017-09-08	桑诺维恩药品公司	杂芳基化合物及其使用方法
CN110229116A (zh) *	2019-07-03	2019-09-13	江苏格罗瑞化学有限公司	一种用于塑料成型加工中的荧光增白剂提纯方法
CN110423236B (zh) *	2019-08-22	2020-12-18	江苏格罗瑞化学有限公司	一种用于纺织品增白的荧光增白剂制备方法
EP4457291A4 (de) *	2021-12-28	2025-10-22	Akdeniz Chemson Kimya Sanayi Ve Ticaret Anonim Sirketi	Verfahren zur herstellung von optischen aufhellern auf benzoxazolbasis
CN114591316B (zh) *	2022-03-14	2024-09-20	黄石市利福达医药化工有限公司	一种2,5-双(苯并噁唑-2-)呋喃的制备方法
CN114605342B (zh) *	2022-03-25	2025-04-08	黄石市利福达医药化工有限公司	一种2-（2-萘基）-5-氯代-苯并噁唑的制备方法

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US2842545A (en) *		1958-07-08		Process for the manufacture of
NL242891A (de) *	1958-09-02
CH439292A (de) *	1961-01-19	1967-07-15	Ciba Geigy	Verfahren zur Herstellung von Thiophenderivaten
BE612775A (de) *	1961-01-19
CH469782A (de) *	1963-11-14	1969-03-15	Ciba Geigy	Verwendung von neuen Bis-oxazolyl-stilbenverbindungen als optische Aufhellmittel ausserhalb der Textilindustrie
US3544585A (en) *	1967-10-04	1970-12-01	Abbott Lab	N'-(4-(hydroxymethyl)-5-pyrazolyl) amidines
JPS55131051A (en) *	1979-03-30	1980-10-11	Mitsubishi Gas Chem Co Inc	High-molecular resin composition
CH650784A5 (de) *	1979-12-06	1985-08-15	Ciba Geigy Ag	Verfahren zur herstellung von benzazolylverbindungen.
US4282355A (en) *	1980-02-14	1981-08-04	Hoechst Aktiengesellschaft	Process for the manufacture of bis-benzoxazolyl-stilbene compounds
DE3216723A1 (de) *	1982-05-05	1983-11-10	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von 4,4'-bis-benz-ox(-thi,-imid)-azol-2-yl-stilbenen
US4921964A (en) *	1989-03-01	1990-05-01	Eastman Kodak Company	Process for the preparation of stilbene derivatives
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ATE223390T1 (de) *	1995-02-13	2002-09-15	Searle & Co	Substituierte isoxazole zur behandlung von entzündung

2001
- 2001-10-09 CN CNB018175821A patent/CN1263748C/zh not_active Expired - Fee Related
- 2001-10-09 US US10/399,312 patent/US20030191320A1/en not_active Abandoned
- 2001-10-09 JP JP2002536268A patent/JP2004511551A/ja active Pending
- 2001-10-09 KR KR1020037004669A patent/KR100820119B1/ko not_active Expired - Fee Related
- 2001-10-09 EP EP01987749A patent/EP1326850B1/de not_active Expired - Lifetime
- 2001-10-09 BR BR0114753-6A patent/BR0114753A/pt not_active Application Discontinuation
- 2001-10-09 ES ES01987749T patent/ES2252320T3/es not_active Expired - Lifetime
- 2001-10-09 RU RU2003114754/04A patent/RU2293084C2/ru not_active IP Right Cessation
- 2001-10-09 DE DE60115080T patent/DE60115080T2/de not_active Expired - Lifetime
- 2001-10-09 CA CA2425165A patent/CA2425165C/en not_active Expired - Fee Related
- 2001-10-09 AT AT01987749T patent/ATE309992T1/de not_active IP Right Cessation
- 2001-10-09 SK SK583-2003A patent/SK287329B6/sk not_active IP Right Cessation
- 2001-10-09 CZ CZ20031344A patent/CZ301894B6/cs not_active IP Right Cessation
- 2001-10-09 MX MXPA03003140A patent/MXPA03003140A/es active IP Right Grant
- 2001-10-09 WO PCT/EP2001/011644 patent/WO2002032886A1/en not_active Ceased
- 2001-10-09 AU AU2002215930A patent/AU2002215930A1/en not_active Abandoned
2007
- 2007-06-21 US US11/821,009 patent/US20070249840A1/en not_active Abandoned

Also Published As

Publication number	Publication date
BR0114753A (pt)	2004-02-10
CA2425165C (en)	2010-08-03
SK5832003A3 (en)	2003-10-07
CA2425165A1 (en)	2002-04-25
MXPA03003140A (es)	2003-07-14
US20030191320A1 (en)	2003-10-09
EP1326850B1 (de)	2005-11-16
CN1469870A (zh)	2004-01-21
ATE309992T1 (de)	2005-12-15
DE60115080D1 (de)	2005-12-22
KR100820119B1 (ko)	2008-04-08
DE60115080T2 (de)	2006-06-08
CN1263748C (zh)	2006-07-12
ES2252320T3 (es)	2006-05-16
CZ20031344A3 (cs)	2003-08-13
AU2002215930A1 (en)	2002-04-29
RU2293084C2 (ru)	2007-02-10
WO2002032886A1 (en)	2002-04-25
EP1326850A1 (de)	2003-07-16
US20070249840A1 (en)	2007-10-25
CZ301894B6 (cs)	2010-07-21
JP2004511551A (ja)	2004-04-15
KR20030038785A (ko)	2003-05-16

Legal Events

Date	Code	Title	Description
2012-07-03	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20111009

Publication	Publication Date	Title
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