UA79018C2 - Ruthenium complex and method for its synthesis, intermediate and method for synthesis thereof, method for metathesis and for ring-closing metathesis reactions - Google Patents

Ruthenium complex and method for its synthesis, intermediate and method for synthesis thereof, method for metathesis and for ring-closing metathesis reactions Download PDF

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Publication number: UA79018C2
Authority: UA; Ukraine
Prior art keywords: formula; synthesis; metathesis; compound; catalyst
Prior art date: 2002-10-15

Application number

UAA200504463A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Boehringer Ingelheim Int

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.)

2002-10-15

Filing date

2003-10-10

Publication date

2007-05-10

2003-10-10 Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int

2007-05-10 Publication of UA79018C2 publication Critical patent/UA79018C2/uk

Links

238000005649 metathesis reaction Methods 0.000 title abstract description 11
238000006798 ring closing metathesis reaction Methods 0.000 title abstract 2
238000000034 method Methods 0.000 title description 15
230000015572 biosynthetic process Effects 0.000 title description 14
238000003786 synthesis reaction Methods 0.000 title description 13
239000012327 Ruthenium complex Substances 0.000 title description 5
239000003054 catalyst Substances 0.000 abstract description 38
238000005686 cross metathesis reaction Methods 0.000 abstract description 6
239000000543 intermediate Substances 0.000 abstract description 5
150000003303 ruthenium Chemical class 0.000 abstract description 5
150000001875 compounds Chemical class 0.000 description 47
239000000243 solution Substances 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 19
239000003446 ligand Substances 0.000 description 15
125000003118 aryl group Chemical group 0.000 description 13
125000004432 carbon atom Chemical group C* 0.000 description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
239000007787 solid Substances 0.000 description 12
125000005843 halogen group Chemical group 0.000 description 10
-1 methylpropyl Chemical group 0.000 description 10
239000002904 solvent Substances 0.000 description 10
238000005481 NMR spectroscopy Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 8
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
229910052707 ruthenium Inorganic materials 0.000 description 7
239000000126 substance Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
150000001336 alkenes Chemical class 0.000 description 6
125000004429 atom Chemical group 0.000 description 6
230000007935 neutral effect Effects 0.000 description 6
238000006772 olefination reaction Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
239000013067 intermediate product Substances 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
125000002015 acyclic group Chemical group 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
239000012300 argon atmosphere Substances 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
229940125782 compound 2 Drugs 0.000 description 3
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
125000005282 allenyl group Chemical group 0.000 description 2
125000002837 carbocyclic group Chemical group 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
150000001879 copper Chemical class 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
238000002844 melting Methods 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
150000003003 phosphines Chemical class 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
ZKYVLGNFTZTQTI-UHFFFAOYSA-N 2-ethenyl-4-nitro-1-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=C([N+]([O-])=O)C=C1C=C ZKYVLGNFTZTQTI-UHFFFAOYSA-N 0.000 description 1
IHFRMUGEILMHNU-UHFFFAOYSA-N 2-hydroxy-5-nitrobenzaldehyde Chemical class OC1=CC=C([N+]([O-])=O)C=C1C=O IHFRMUGEILMHNU-UHFFFAOYSA-N 0.000 description 1
TZPVPJUHWLYGSL-UHFFFAOYSA-N 5-nitro-2-propan-2-yloxybenzaldehyde Chemical compound CC(C)OC1=CC=C([N+]([O-])=O)C=C1C=O TZPVPJUHWLYGSL-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
244000241257 Cucumis melo Species 0.000 description 1
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
241001331845 Equus asinus x caballus Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000219492 Quercus Species 0.000 description 1
241000022563 Rema Species 0.000 description 1
229910006898 SnSi Inorganic materials 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000003609 aryl vinyl group Chemical group 0.000 description 1
239000012267 brine Substances 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
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000013522 chelant Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000002739 cryptand Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000001514 detection method Methods 0.000 description 1
GDWAYKGILJJNBB-UHFFFAOYSA-N diethyl 2-prop-2-enylpropanedioate Chemical compound CCOC(=O)C(CC=C)C(=O)OCC GDWAYKGILJJNBB-UHFFFAOYSA-N 0.000 description 1
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000013081 microcrystal Substances 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
150000003077 polyols Chemical group 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
MKNZKCSKEUHUPM-UHFFFAOYSA-N potassium;butan-1-ol Chemical compound [K+].CCCCO MKNZKCSKEUHUPM-UHFFFAOYSA-N 0.000 description 1
HVOCMPMAOLOKRK-UHFFFAOYSA-N potassium;pentan-1-olate Chemical compound [K+].CCCCC[O-] HVOCMPMAOLOKRK-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
SETMGIIITGNLAS-UHFFFAOYSA-N spizofurone Chemical compound O=C1C2=CC(C(=O)C)=CC=C2OC21CC2 SETMGIIITGNLAS-UHFFFAOYSA-N 0.000 description 1
229950001870 spizofurone Drugs 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Indole Compounds (AREA)

UAA200504463A 2002-10-15 2003-10-10 Ruthenium complex and method for its synthesis, intermediate and method for synthesis thereof, method for metathesis and for ring-closing metathesis reactions UA79018C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PL356652A PL199412B1 (pl)	2002-10-15	2002-10-15	Nowe kompleksy rutenu jako (pre)katalizatory reakcji metatezy, pochodne 2-alkoksy-5-nitrostyrenu jako związki pośrednie i sposób ich wytwarzania
PCT/EP2003/011222 WO2004035596A1 (en)	2002-10-15	2003-10-10	Ruthenium complexes as (pre)catalysts for metathesis reactions

Publications (1)

Publication Number	Publication Date
UA79018C2 true UA79018C2 (en)	2007-05-10

Family

ID=32105755

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200504463A UA79018C2 (en)	2002-10-15	2003-10-10	Ruthenium complex and method for its synthesis, intermediate and method for synthesis thereof, method for metathesis and for ring-closing metathesis reactions

Country Status (31)

Country	Link
US (1)	US6867303B2 (pl)
EP (1)	EP1554294B1 (pl)
JP (1)	JP4264418B2 (pl)
KR (1)	KR101057963B1 (pl)
CN (1)	CN1291996C (pl)
AR (1)	AR041620A1 (pl)
AT (1)	ATE332906T1 (pl)
AU (1)	AU2003271713B2 (pl)
BR (1)	BR0314856B1 (pl)
CA (1)	CA2502342C (pl)
CO (1)	CO5560614A2 (pl)
DE (2)	DE60306795T2 (pl)
DK (1)	DK1554294T3 (pl)
EA (1)	EA008352B1 (pl)
EC (1)	ECSP055653A (pl)
ES (1)	ES2268412T3 (pl)
HR (1)	HRP20050339B1 (pl)
IL (1)	IL168002A (pl)
ME (1)	ME00345B (pl)
MX (1)	MXPA05003647A (pl)
MY (1)	MY127285A (pl)
NO (1)	NO335760B1 (pl)
NZ (1)	NZ539944A (pl)
PE (1)	PE20040510A1 (pl)
PL (2)	PL199412B1 (pl)
RS (1)	RS50334B (pl)
TW (1)	TWI310768B (pl)
UA (1)	UA79018C2 (pl)
UY (1)	UY28020A1 (pl)
WO (1)	WO2004035596A1 (pl)
ZA (1)	ZA200501533B (pl)

Families Citing this family (109)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2003007697A (ja) *	2001-06-21	2003-01-10	Hitachi Kokusai Electric Inc	半導体装置の製造方法、基板処理方法および基板処理装置
US6620955B1 (en)	2001-11-15	2003-09-16	Richard L. Pederson	Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts
US7205424B2 (en) *	2003-06-19	2007-04-17	University Of New Orleans Research And Technology Foundation, Inc.	Preparation of ruthenium-based olefin metathesis catalysts
US7241898B2 (en)	2003-08-02	2007-07-10	Boehringer Ingelheim International Gmbh	Metathesis catalysts
US7491794B2 (en)	2003-10-14	2009-02-17	Intermune, Inc.	Macrocyclic compounds as inhibitors of viral replication
EP1543875A1 (en) *	2003-12-04	2005-06-22	Boehringer Ingelheim Pharma GmbH & Co. KG	Novel metathesis ruthenium catalyst
US7109344B2 (en) *	2003-12-04	2006-09-19	Boehringer Ingelheim International Gmbh	Ruthenium catalyst
DE102004033312A1 (de) *	2004-07-08	2006-01-26	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Kontinuierliches Metatheseverfahren mit Ruthenium-Katalysatoren
DE102005002336A1 (de) *	2005-01-17	2006-07-20	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Verfahren zur Durchführung von kontinuierlichen Olefin-Ringschluss-Metathesen in komprimiertem Kohlendioxid
RU2435778C2 (ru) *	2005-07-04	2011-12-10	Заннан Сайтех Ко., Лтд.	Лиганд комплекса рутения, комплекс рутения, катализатор комплекса рутения и способы его получения и применения
KR101294467B1 (ko) *	2005-07-25	2013-09-09	인터뮨, 인크.	Ｃ형 간염 바이러스 복제의 신규 거대고리형 억제제
BRPI0617274A2 (pt)	2005-10-11	2011-07-19	Intermune Inc	compostos e métodos para a inibição de replicação viral de hepatite c
DE602006017249D1 (de) *	2005-11-09	2010-11-11	Boehringer Ingelheim Int	Herstellung von katalysatoren
EP1815838B1 (en)	2006-02-02	2010-09-08	3M Innovative Properties Company	Solid materials obtainable by the ring-opening methathesis polymerization
CN100491326C (zh) *	2006-02-13	2009-05-27	中国科学院化学研究所	一种3-羟基烯酸衍生物及其制备方法与应用
DE102006008521A1 (de) *	2006-02-22	2007-08-23	Lanxess Deutschland Gmbh	Verwendung von Katalysatoren mit erhöhter Aktivität für die NBR-Metathese
DE102006008520A1 (de)	2006-02-22	2007-08-23	Lanxess Deutschland Gmbh	Neue Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen
PL379879A1 (pl)	2006-06-07	2007-12-10	Umicore Ag & Co.Kg.	Kompleksy rutenu i osmu, sposób ich wytwarzania oraz ich zastosowanie jako (pre)katalizatorów reakcji metatezy
JP5323691B2 (ja)	2006-06-30	2013-10-23	エフ．ホフマン−ラロシュアーゲー	メタセシス反応用触媒としての新規ルテニウム錯体
RU2008152171A (ru) *	2006-07-05	2010-08-10	Интермьюн, Инк. (Us)	Новые ингибиторы вирусной репликации гепатита с
US20090253904A1 (en) *	2006-07-18	2009-10-08	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Process for the Preparation of a Tetrahydro-1H-Azepines
RU2311231C1 (ru) *	2006-08-15	2007-11-27	ООО "Объединенный центр исследований и разработок"	Катализатор для получения эфиров акриловой кислоты по реакции метатезиса диалкилмалеатов (варианты) и каталитическая композиция на его основе
DE102006040569A1 (de)	2006-08-30	2008-03-06	Lanxess Deutschland Gmbh	Verfahren zum Metathese-Abbau von Nitrilkautschuken
FR2909382B1 (fr)	2006-11-30	2009-01-23	Enscr	Complexes catalytiques a base de ruthenium et utilisation de tels complexes pour la metathese d'olefines
EP1942125A1 (en)	2006-12-20	2008-07-09	3M Innovative Properties Company	Compositions curable by ring opening metathesis polymerarization at low temperatures and their application in the dental field
AR066191A1 (es)	2007-03-22	2009-08-05	Schering Corp	Proceso e intermediarios para la sintesis de compuestos 8- [ ( 1- (3,5- bis- ( trifluorometil) fenil) - etoxi ) - metil]- 8 fenil - 1,7- diaza - espiro (4, 5) decan -2 ona
SG174809A1 (en) *	2007-05-03	2011-10-28	Intermune Inc	Macrocyclic compounds useful as inhibitors of hepatitis c virus
AU2008251425A1 (en) *	2007-05-10	2008-11-20	Array Biopharma, Inc.	Novel peptide inhibitors of hepatitis C virus replication
US20080306230A1 (en) *	2007-06-07	2008-12-11	General Electric Company	Composition and Associated Method
EP2170805B1 (en) *	2007-06-21	2016-03-16	Amgen Inc.	Methods of synthesizing cinacalcet and salts thereof
DE102007039695A1 (de)	2007-08-22	2009-02-26	Lanxess Deutschland Gmbh	Katalysatoren für Metathese-Reaktionen
DE102007039526A1 (de)	2007-08-21	2009-02-26	Lanxess Deutschland Gmbh	Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen
EP2027920B1 (de)	2007-08-21	2014-10-08	LANXESS Deutschland GmbH	Katalysatoren für Metathese-Reaktionen
DE102007039527A1 (de)	2007-08-21	2009-02-26	Lanxess Deutschland Gmbh	Katalysatoren für Metathese-Reaktionen
DE102007039525A1 (de)	2007-08-21	2009-02-26	Lanxess Deutschland Gmbh	Verfahren zum Metathese-Abbau von Nitrilkautschuk
US8419332B2 (en) *	2007-10-19	2013-04-16	Atlas Bolt & Screw Company Llc	Non-dimpling fastener
MX2010011306A (es)	2008-04-15	2010-11-09	Intermune Inc	Nuevos inhibidores macrociclicos de la replicacion del virus de la hepatitis c.
EP2143489A1 (de) *	2008-07-08	2010-01-13	Lanxess Deutschland GmbH	Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen
EP2147721A1 (de) *	2008-07-08	2010-01-27	Lanxess Deutschland GmbH	Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen
CA2736195C (en)	2008-09-05	2017-05-16	Opko Health, Inc.	Process and intermediates for the synthesis of 8-[{1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one compounds
DE102009005951A1 (de)	2009-01-23	2010-07-29	Evonik Degussa Gmbh	Aldehydfunktionale Verbindungen
EP2210870A1 (de)	2009-01-23	2010-07-28	Evonik Degussa GmbH	Hydroxy- und aldehydfunktionale Verbindungen
EP2803658A1 (en)	2009-02-03	2014-11-19	IDENIX Pharmaceuticals, Inc.	Phosphinate ruthenium complexes
AR075584A1 (es) *	2009-02-27	2011-04-20	Intermune Inc	COMPOSICIONES TERAPEUTICAS QUE COMPRENDEN beta-D-2'-DESOXI-2'-FLUORO-2'-C-METILCITIDINA Y UN DERIVADO DE ACIDO ISOINDOL CARBOXILICO Y SUS USOS. COMPUESTO.
CN102395427B (zh) *	2009-03-17	2016-03-16	约翰森·马瑟公开有限公司	在Ru(II)催化剂存在下氢化酮类的方法
EP2255877B1 (en)	2009-05-07	2014-09-24	Umicore AG & Co. KG	Method for preparation of ruthenium-based metathesis catalysts with chelating alkylidene ligands
ES2449298T3 (es) *	2009-05-07	2014-03-19	F. Hoffmann-La Roche Ag	Proceso para la preparación de catalizadores complejos de metátesis de rutenio
EP2289621A1 (en)	2009-08-31	2011-03-02	LANXESS Deutschland GmbH	Process for the preparation of low molecular weight hydrogenated nitrile rubber
EP2289623A1 (en)	2009-08-31	2011-03-02	LANXESS Deutschland GmbH	Metathesis of nitrile rubbers in the presence of transition metal catalysts
US20130029069A1 (en)	2009-08-31	2013-01-31	Lanxess Deutschland Gmbh	Vulcanizable polymer composition comprising a low molecular weight with optionally hydrogenated nitrile rubber
CN105001302A (zh) *	2009-09-28	2015-10-28	英特穆恩公司	C型肝炎病毒复制的环肽抑制剂
WO2011079439A1 (en) *	2009-12-30	2011-07-07	Zannan Scitech Co., Ltd.	Highly active metathesis catalysts selective for romp and rcm reactions
US8592618B2 (en) *	2010-01-08	2013-11-26	Zannan Scitech Co., Ltd.	Highly active metathesis catalysts selective for ROMP and RCM reactions
EP2361683A1 (en) *	2010-01-29	2011-08-31	Umicore AG & Co. KG	Process for preparation of ruthenium-based carbene catalysts with chelating alkylidene ligands
EP2395034A1 (de)	2010-06-14	2011-12-14	LANXESS Deutschland GmbH	Blends aus teilhydriertem Nitrilkautschuk und Silikonkautschuk, darauf basierende vulkanisierbaren Mischungen und Vulkanisate
CA2806754C (en)	2010-07-30	2020-04-07	Ecole Nationale Superieure De Chimie De Rennes	Ruthenium compounds as metathesis catalysts
EP2418225A1 (de)	2010-08-09	2012-02-15	LANXESS Deutschland GmbH	Teilhydrierte Nitrilkautschuke
EP2484700B1 (de)	2011-02-04	2013-10-09	LANXESS Deutschland GmbH	Funktionalisierte Nitrilkautschuke und ihre Herstellung
US8633280B2 (en) *	2011-03-30	2014-01-21	Zannan Scitech Co., Ltd	Methods of modifying polymers with highly active and selective metathesis catalysts
PL216649B1 (pl)	2011-06-06	2014-04-30	Univ Warszawski	Nowe kompleksy rutenu, sposób ich wytwarzania oraz zastosowanie w reakcji metatezy olefin
PL220408B1 (pl) *	2011-09-26	2015-10-30	Inst Chemii Organicznej Polskiej Akademii Nauk	Kompleks rutentu, sposób jego wytwarzania oraz zastosowanie
US8975414B2 (en) *	2011-10-13	2015-03-10	Elevance Renewable Sciences, Inc.	Methods for preparing ruthenium carbene complex precursors and ruthenium carbene complexes
WO2013056400A1 (en) *	2011-10-21	2013-04-25	Lanxess Deutschland Gmbh	Catalyst compositions and their use for hydrogenation of nitrile rubber
WO2013056463A1 (en)	2011-10-21	2013-04-25	Lanxess Deutschland Gmbh	Catalyst compositions and their use for hydrogenation of nitrile rubber
WO2013056461A1 (en) *	2011-10-21	2013-04-25	Lanxess Deutschland Gmbh	Catalyst compositions and their use for hydrogenation of nitrile rubber
WO2013098052A2 (en)	2011-12-28	2013-07-04	Lanxess Deutschland Gmbh	Metathesis of nitrile rubbers in the presence of transition metal complex catalysts
WO2013098056A1 (en)	2011-12-28	2013-07-04	Lanxess Deutschland Gmbh	Purification of optionally hydrogenated nitrile rubber
PL230302B1 (pl)	2012-02-27	2018-10-31	Apeiron Synthesis Spolka Z Ograniczona Odpowiedzialnoscia	Katalizatory metatezy zawierające grupy oniowe
EP2639219B1 (en) *	2012-03-14	2016-08-10	Umicore AG & Co. KG	Ruthenium-based metathesis catalysts and precursors for their preparation
JP6092379B2 (ja)	2012-06-29	2017-03-08	アペイロンシンセシスエスアー	金属錯体、その適用、及びメタセシス反応の実施方法
PL400162A1 (pl) *	2012-07-27	2014-02-03	Apeiron Synthesis Spólka Z Ograniczona Odpowiedzialnoscia	Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy
CN103936793B (zh)	2013-01-10	2017-02-08	光明创新（武汉）有限公司	含卡宾配体的催化剂及其制备方法与其在复分解反应中的应用
WO2014201300A1 (en)	2013-06-12	2014-12-18	Trustees Of Boston College	Catalysts for efficient z-selective metathesis
EP2835381A1 (en)	2013-08-09	2015-02-11	Lanxess Elastomers B.V.	Functionalized olefinic copolymers
PL3488925T3 (pl)	2014-04-10	2022-09-05	California Institute Of Technology	Kompleksy rutenu
US9441078B2 (en)	2014-05-30	2016-09-13	Pall Corporation	Self-assembling polymers—I
US9616395B2 (en)	2014-05-30	2017-04-11	Pall Corportaion	Membrane comprising self-assembled block copolymer and process for producing the same by spray coating (Ic)
US9765171B2 (en)	2014-05-30	2017-09-19	Pall Corporation	Self-assembling polymers—V
US9593218B2 (en)	2014-05-30	2017-03-14	Pall Corporation	Self-assembled structure and membrane comprising block copolymer and process for producing the same by spin coating (IIIa)
US9592477B2 (en)	2014-05-30	2017-03-14	Pall Corporation	Membrane comprising self-assembled block copolymer and process for producing the same by hybrid casting (Ib)
US9593219B2 (en)	2014-05-30	2017-03-14	Pall Corporation	Membrane comprising self-assembled block copolymer and process for producing the same by spin coating (IIa)
US9604181B2 (en)	2014-05-30	2017-03-28	Pall Corporation	Membrane comprising self-assembled block copolymer and process for producing the same by spray coating (IIc)
US9162189B1 (en)	2014-05-30	2015-10-20	Pall Corporation	Membrane comprising self-assembled block copolymer and process for producing the same by spin coating (Ia)
US9593217B2 (en)	2014-05-30	2017-03-14	Pall Corporation	Self-assembled structure and membrane comprising block copolymer and process for producing the same by spin coating (Va)
US9193835B1 (en)	2014-05-30	2015-11-24	Pall Corporation	Self-assembling polymers—IV
US9592476B2 (en)	2014-05-30	2017-03-14	Pall Corporation	Membrane comprising self-assembled block copolymer and process for producing the same by hybrid casting (IIb)
US9598543B2 (en)	2014-05-30	2017-03-21	Pall Corporation	Self-assembled structure and membrane comprising block copolymer and process for producing the same by spin coating (VIa)
US9169361B1 (en)	2014-05-30	2015-10-27	Pall Corporation	Self-assembling polymers—VI
US9328206B2 (en)	2014-05-30	2016-05-03	Pall Corporation	Self-assembling polymers—III
US9469733B2 (en)	2014-05-30	2016-10-18	Pall Corporation	Self-assembled structure and membrane comprising block copolymer and process for producing the same by spin coating (IVa)
US9163122B1 (en)	2014-05-30	2015-10-20	Pall Corporation	Self-assembling polymers—II
US9260569B2 (en)	2014-06-30	2016-02-16	Pall Corporation	Hydrophilic block copolymers and method of preparation thereof (III)
US9718924B2 (en)	2014-06-30	2017-08-01	Pall Corporation	Hydrophilic block copolymers and membranes prepared therefrom (II)
US9309367B2 (en)	2014-06-30	2016-04-12	Pall Corporation	Membranes comprising cellulosic material and hydrophilic block copolymer (V)
US9394407B2 (en)	2014-06-30	2016-07-19	Pall Corporation	Hydrophilic block copolymers and membranes prepared therefrom (I)
US9303133B2 (en)	2014-06-30	2016-04-05	Pall Corporation	Hydrophilic membranes and method of preparation thereof (IV)
US9962662B2 (en)	2014-06-30	2018-05-08	Pall Corporation	Fluorinated polymer and use thereof in the preparation of hydrophilic membranes (vi)
US9254466B2 (en)	2014-06-30	2016-02-09	Pall Corporation	Crosslinked cellulosic membranes
EP3164409B1 (en) *	2014-07-03	2021-09-01	Guang Ming Innovation Company (Wuhan)	Group 8 transition metal catalysts and method for making same and process for use of same in metathesis reaction
EP3034486A1 (de)	2014-12-16	2016-06-22	LANXESS Deutschland GmbH	1,3-Butadien-Synthese
PL238806B1 (pl)	2015-09-30	2021-10-04	Apeiron Synthesis Spolka Akcyjna	Kompleks rutenu i sposób jego wytwarzania, związek pośredni stosowany w tym sposobie oraz zastosowanie kompleksu rutenu i związku pośredniego w metatezie olefin
US10688481B2 (en)	2016-11-09	2020-06-23	Ximo Ag	Ruthenium complexes useful for catalyzing metathesis reactions
HUE073559T2 (hu)	2017-02-17	2026-01-28	Provivi Inc	Feromonok és kapcsolódó anyagok szintézise olefin-metatézisen keresztül
KR102702569B1 (ko)	2017-12-08	2024-09-06	아란세오 도이치란드 게엠베하	루테늄 착물 촉매를 사용하여 니트릴 고무를 생성하기 위한 방법
WO2019121153A1 (en)	2017-12-18	2019-06-27	Arlanxeo Deutschland Gmbh	Hydrogenation of nitrile butadiene rubber latex
EP3784390A1 (en)	2018-04-27	2021-03-03	ARLANXEO Deutschland GmbH	Use of ruthenium and osmium catalysts for the metathesis of nitrile rubber
JP7417554B2 (ja)	2018-07-23	2024-01-18	アランセオ・ドイチュランド・ゲーエムベーハー	ニトリルゴムをメタセシスするための触媒の使用
EP3894074A2 (en)	2018-12-12	2021-10-20	ARLANXEO Deutschland GmbH	Catalyst system containing a metathesis catalyst and at least one phenolic compound and a process for metathesis of nitrile-butadiene rubber (nbr) using the catalyst system
CA3122882A1 (en)	2018-12-17	2020-06-25	Arlanxeo Deutschland Gmbh	Process for preparing hnbr solutions with alternative solvents

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE448019T1 (de)	2000-08-10	2009-11-15	Trustees Boston College	Wiederverwendbare methathese-katalysatoren

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ES2268412T3 (es)	2007-03-16
BR0314856A (pt)	2005-08-02
UY28020A1 (es)	2004-05-31
WO2004035596A1 (en)	2004-04-29
EP1554294A1 (en)	2005-07-20
DE60306795D1 (de)	2006-08-24
RS20050287A (sr)	2007-06-04
CO5560614A2 (es)	2005-09-30
NZ539944A (en)	2007-05-31
ATE332906T1 (de)	2006-08-15
NO335760B1 (no)	2015-02-09
CA2502342C (en)	2012-06-19
EP1554294B1 (en)	2006-07-12
PE20040510A1 (es)	2004-09-14
DK1554294T3 (da)	2006-11-06
DE20320324U1 (de)	2004-05-27
PL356652A1 (pl)	2004-04-19
IL168002A (en)	2009-11-18
AU2003271713B2 (en)	2010-04-29
PL374739A1 (pl)	2005-10-31
AU2003271713A1 (en)	2004-05-04
KR20050061539A (ko)	2005-06-22
KR101057963B1 (ko)	2011-08-22
DE60306795T2 (de)	2006-11-16
MY127285A (en)	2006-11-30
BR0314856B1 (pt)	2014-05-27
MEP51508A (en)	2011-02-10
JP2006503085A (ja)	2006-01-26
US6867303B2 (en)	2005-03-15
HK1070076A1 (en)	2005-06-10
CN1291996C (zh)	2006-12-27
EA200500607A1 (ru)	2005-10-27
US20040127350A1 (en)	2004-07-01
ECSP055653A (es)	2005-07-06
JP4264418B2 (ja)	2009-05-20
HRP20050339B1 (hr)	2013-07-31
MXPA05003647A (es)	2005-06-08
ME00345B (me)	2011-05-10
AR041620A1 (es)	2005-05-26
TW200420569A (en)	2004-10-16
RS50334B (sr)	2009-11-10
CN1571791A (zh)	2005-01-26
HRP20050339A2 (en)	2006-05-31
ZA200501533B (en)	2006-11-29
PL207783B1 (pl)	2011-02-28
EA008352B1 (ru)	2007-04-27
PL199412B1 (pl)	2008-09-30
CA2502342A1 (en)	2004-04-29
TWI310768B (en)	2009-06-11

Publication	Publication Date	Title
UA79018C2 (en)	2007-05-10	Ruthenium complex and method for its synthesis, intermediate and method for synthesis thereof, method for metathesis and for ring-closing metathesis reactions
EP0916637B1 (en)	2005-04-20	Process for preparating optically active compounds
Hii et al.	2001	The intermolecular asymmetric Heck reaction: mechanistic and computational studies
JPH10279506A (ja)	1998-10-20	ビスヒドロキシメチル化合物の製造方法
Takeda et al.	2006	Asymmetric total synthesis of enantiopure (−)-methyl jasmonate via catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfone
JP2001261689A (ja)	2001-09-26	光学活性ルテニウムホスフィン錯体の製造方法及び該錯体を用いた光学活性アルコールの製造方法
WO2008135386A1 (fr)	2008-11-13	Ligands chiraux de type carbenes n-heterocycliques pour la catalyse asymetrique
IE54216B1 (en)	1989-07-19	Stereospecific synthesis of 5-phenyl-2s-pentanol
US6878663B2 (en)	2005-04-12	Method for producing palladium complex compound
Wencel et al.	2008	Chiral phosphinoazomethinylate salts as new ‘one-step available’ligands for copper-catalyzed asymmetric conjugate addition
JP3552934B2 (ja)	2004-08-11	安息香酸アミド類の製造方法
WO2019039565A1 (ja)	2019-02-28	ジヒドロキシビフェニル化合物、ビスホスファイト化合物、触媒、アルデヒド類の製造方法及びアルコールの製造方法
US20030109574A1 (en)	2003-06-12	Process for producing 4-substituted benzopyran derivatives
WO1996029295A1 (en)	1996-09-26	Process for preparing asymmetric compound by using metal complex
CN109563029A (zh)	2019-04-02	用于制备二氢茚酮类的方法
EP0152324B1 (fr)	1986-11-12	Nouveau tétraène, sa préparation et son emploi
CN104987302B (zh)	2017-03-01	N,n‑二乙基‑甲酸4‑卤代甲基‑3,5‑二甲基‑苯酚酯化合物及其制备方法
CN104529898B (zh)	2016-07-27	氮杂二苯并环辛炔类化合物及其制备方法
JP3720874B2 (ja)	2005-11-30	新規のパラダサイクル及びそれらの製造方法
JPS6411009B2 (pl)	1989-02-23
EP1700838A1 (en)	2006-09-13	A process for the preparation of coenzyme Q10
JPH09249607A (ja)	1997-09-22	光学活性１，１’−ビフェナンスリル−２，２’−ジオール、当該化合物の製造法及び当該化合物からなる光学分割剤
JP2007297285A (ja)	2007-11-15	光学活性なヒドロキシ化合物の製法
JPH04108757A (ja)	1992-04-09	テルペン類の製造方法
JP2001139588A (ja)	2001-05-22	パラジウム錯化合物