UA74871C2 - A process for the preparation of imidazole compounds - Google Patents

A process for the preparation of imidazole compounds Download PDF

Info

Publication number: UA74871C2
Authority: UA; Ukraine
Prior art keywords: compound; methyl; chlorophenyl; temperature; added
Prior art date: 2001-03-12

Application number

UA2003087776A

Other languages

English (en)

Ukrainian (uk)

Inventor

Walter Ferdinand Mari Filliers

Rudy Laurent Maria Broeck

Stefan Marcel Herman Leurs

Original Assignee

Janssen Pharmaceutica Nv

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.)

2001-03-12

Filing date

2002-05-03

Publication date

2006-02-15

2002-05-03 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2006-02-15 Publication of UA74871C2 publication Critical patent/UA74871C2/uk

Links

238000000034 method Methods 0.000 title abstract description 16
238000002360 preparation method Methods 0.000 title abstract description 7
230000008569 process Effects 0.000 title abstract description 4
150000002460 imidazoles Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 abstract description 39
-1 silyl halide Chemical class 0.000 abstract description 17
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 abstract description 5
WOYOASASOHZEDR-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-[(4-chlorophenyl)-hydroxy-(3-methylimidazol-4-yl)methyl]-1-methylquinolin-2-one Chemical compound CN1C=NC=C1C(O)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)N(C)C2=CC=1)C1=CC=C(Cl)C=C1 WOYOASASOHZEDR-UHFFFAOYSA-N 0.000 abstract 1
IDKYCLCDTGIFBA-UHFFFAOYSA-N 6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-1-methylquinolin-2-one Chemical compound C=1C(=O)N(C)C2=CC=C(C(=O)C=3C=CC(Cl)=CC=3)C=C2C=1C1=CC=CC(Cl)=C1 IDKYCLCDTGIFBA-UHFFFAOYSA-N 0.000 abstract 1
239000011541 reaction mixture Substances 0.000 description 17
239000000047 product Substances 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
239000000243 solution Substances 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
206010028980 Neoplasm Diseases 0.000 description 5
239000002253 acid Substances 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
108700020796 Oncogene Proteins 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
125000000068 chlorophenyl group Chemical group 0.000 description 4
125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
206010062717 Increased upper airway secretion Diseases 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
102000043276 Oncogene Human genes 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
125000004356 hydroxy functional group Chemical group O* 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
208000026435 phlegm Diseases 0.000 description 3
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
102000004357 Transferases Human genes 0.000 description 2
108090000992 Transferases Proteins 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 2
235000018102 proteins Nutrition 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
239000007858 starting material Substances 0.000 description 2
150000003892 tartrate salts Chemical class 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
230000009466 transformation Effects 0.000 description 2
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
QYEMNJMSULGQRD-UHFFFAOYSA-N 1-methyl-2-quinolone Chemical compound C1=CC=C2C=CC(=O)N(C)C2=C1 QYEMNJMSULGQRD-UHFFFAOYSA-N 0.000 description 1
YONLFQNRGZXBBF-UHFFFAOYSA-N 2,3-dibenzoyloxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)OC(C(O)=O)C(C(=O)O)OC(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-UHFFFAOYSA-N 0.000 description 1
KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
208000002874 Acne Vulgaris Diseases 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000271566 Aves Species 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
102000007317 Farnesyltranstransferase Human genes 0.000 description 1
108010007508 Farnesyltranstransferase Proteins 0.000 description 1
241000233866 Fungi Species 0.000 description 1
102000013404 Geranyltranstransferase Human genes 0.000 description 1
108010026318 Geranyltranstransferase Proteins 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
241000237852 Mollusca Species 0.000 description 1
208000010642 Porphyrias Diseases 0.000 description 1
102000001708 Protein Isoforms Human genes 0.000 description 1
108010029485 Protein Isoforms Proteins 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
206010052428 Wound Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
230000001594 aberrant effect Effects 0.000 description 1
206010000496 acne Diseases 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
235000013361 beverage Nutrition 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000001273 butane Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
TZPZCTBZJKZFGY-UHFFFAOYSA-N chloro-tris(2-methylpropyl)silane Chemical compound CC(C)C[Si](Cl)(CC(C)C)CC(C)C TZPZCTBZJKZFGY-UHFFFAOYSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
IWYZTXQESXGICT-UHFFFAOYSA-N dibenzoyl butanediperoxoate Chemical compound C(CCC(=O)OOC(C1=CC=CC=C1)=O)(=O)OOC(C1=CC=CC=C1)=O IWYZTXQESXGICT-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000006073 displacement reaction Methods 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
238000002474 experimental method Methods 0.000 description 1
230000006126 farnesylation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000002737 fuel gas Substances 0.000 description 1
230000012010 growth Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical group CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000012528 membrane Substances 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
102000027450 oncoproteins Human genes 0.000 description 1
108091008819 oncoproteins Proteins 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000012925 reference material Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000000844 transformation Methods 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000004222 uncontrolled growth Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Epoxy Resins (AREA)

UA2003087776A 2001-03-12 2002-05-03 A process for the preparation of imidazole compounds UA74871C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP01200928		2001-03-12
PCT/EP2002/002459 WO2002072574A1 (en)	2001-03-12	2002-03-05	Process for the preparation of imidazole compounds

Publications (1)

Publication Number	Publication Date
UA74871C2 true UA74871C2 (en)	2006-02-15

Family

ID=8180004

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2003087776A UA74871C2 (en)	2001-03-12	2002-05-03	A process for the preparation of imidazole compounds

Country Status (31)

Country	Link
US (1)	US6844439B2 (de)
EP (1)	EP1373255B1 (de)
JP (1)	JP4257698B2 (de)
KR (1)	KR100849042B1 (de)
CN (1)	CN1246318C (de)
AR (1)	AR035944A1 (de)
AT (1)	ATE287882T1 (de)
AU (1)	AU2002253101B2 (de)
BR (1)	BRPI0208075B8 (de)
CA (1)	CA2438421C (de)
CZ (1)	CZ300622B6 (de)
DE (1)	DE60202755T2 (de)
DK (1)	DK1373255T3 (de)
EA (1)	EA006770B1 (de)
EE (1)	EE05247B1 (de)
ES (1)	ES2236505T3 (de)
HR (1)	HRP20030695B1 (de)
HU (1)	HU230282B1 (de)
IL (2)	IL157839A0 (de)
MX (1)	MXPA03008205A (de)
MY (1)	MY124838A (de)
NO (1)	NO324954B1 (de)
NZ (1)	NZ528620A (de)
PL (1)	PL208238B1 (de)
PT (1)	PT1373255E (de)
SI (1)	SI1373255T1 (de)
SK (1)	SK287807B6 (de)
TW (1)	TWI249532B (de)
UA (1)	UA74871C2 (de)
WO (1)	WO2002072574A1 (de)
ZA (1)	ZA200307117B (de)

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BR0208010A (pt)	2001-03-12	2004-12-21	Avanir Pharmaceuticals	Composto de benzimidazol para modulação de ige e inibição de proliferação celular
AU2003270426A1 (en)	2002-09-12	2004-04-30	Avanir Pharmaceuticals	PHENYL-INDOLE COMPOUNDS FOR MODULATING IgE AND INHIBITING CELLULAR PROLIFERATION
TWI276631B (en)	2002-09-12	2007-03-21	Avanir Pharmaceuticals	Phenyl-aza-benzimidazole compounds for modulating IgE and inhibiting cellular proliferation
CA2559221A1 (en) *	2004-03-18	2005-09-29	Brigham And Women's Hospital, Inc.	Methods for the treatment of synucleinopathies
JP4917021B2 (ja) *	2004-05-03	2012-04-18	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	スルフィンイミン類に対するリチオ化されたｎ−メチルイミダゾールのジアステレオ選択的付加
US7456287B2 (en)	2004-05-03	2008-11-25	Janssen Pharmaceutica N.V.	Diastereoselective synthesis process for the preparation of imidazole compounds
ATE471316T1 (de) *	2004-05-03	2010-07-15	Janssen Pharmaceutica Nv	Diastereoselektives syntheseverfahren mit 6-brom- 4-(3-chlorphenyl)-2-methoxychinolin
AU2006331542A1 (en)	2005-12-23	2007-07-05	Link Medicine Corporation	Treatment of synucleinopathies
WO2009151683A2 (en) *	2008-03-12	2009-12-17	Link Medicine Corporation	Quinolinone farnesyl transferase inhibitors for the treatment of synucleinopathies and other indications
KR101044430B1 (ko) *	2009-09-25	2011-06-27	듀오백코리아 주식회사	요추받이를 포함하는 의자의 등 지지 장치
KR101107900B1 (ko) *	2009-10-21	2012-01-25	성용기업 주식회사	의자용 허리지지장치
US10471055B2 (en)	2015-08-17	2019-11-12	Kura Oncology, Inc.	Methods of treating cancer patients with farnesyltransferase inhibitors
HRP20210544T1 (hr)	2016-11-03	2021-08-20	Kura Oncology, Inc.	Inhibitori farneziltransferaze za uporabu u liječenju raka
US10954210B2 (en)	2016-12-08	2021-03-23	Hangzhou Solipharma Co., Ltd.	Crystal form of tipifarnib and preparation method and pharmaceutical composition thereof
WO2019222565A1 (en)	2018-05-18	2019-11-21	Kura Oncology, Inc.	Synthesis of tipifarnib

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW349948B (en)	1995-10-31	1999-01-11	Janssen Pharmaceutica Nv	Farnesyl transferase inhibiting 2-quinolone derivatives
DE69635966T2 (de) *	1995-12-08	2006-11-30	Janssen Pharmaceutica N.V.	(Imidazol-5-yl)Methyl-2-Chinolinonderivate als Farnesyl Protein transferase Inhibitoren
TW591030B (en) *	1997-03-10	2004-06-11	Janssen Pharmaceutica Nv	Farnesyl transferase inhibiting 1,8-annelated quinolinone derivatives substituted with N- or C-linked imidazoles
SK146199A3 (en) *	1997-04-25	2000-06-12	Janssen Pharmaceutica Nv	Farnesyltransferase inhibiting quinazolinones
KR20010072991A (ko) *	1998-08-27	2001-07-31	실버스타인 아써 에이.	항암제로서 유용한 알키닐-치환된 퀴놀린-2-온 유도체
CA2341739C (en)	1998-08-27	2005-07-12	Pfizer Products Inc.	Quinolin-2-one derivatives useful as anticancer agents

2002
- 2002-03-05 ES ES02722184T patent/ES2236505T3/es not_active Expired - Lifetime
- 2002-03-05 US US10/471,215 patent/US6844439B2/en not_active Expired - Lifetime
- 2002-03-05 SK SK1246-2003A patent/SK287807B6/sk unknown
- 2002-03-05 HR HR20030695A patent/HRP20030695B1/xx not_active IP Right Cessation
- 2002-03-05 EP EP02722184A patent/EP1373255B1/de not_active Expired - Lifetime
- 2002-03-05 BR BRPI0208075-3 patent/BRPI0208075B8/pt not_active IP Right Cessation
- 2002-03-05 AT AT02722184T patent/ATE287882T1/de active
- 2002-03-05 HU HU0303443A patent/HU230282B1/hu unknown
- 2002-03-05 DK DK02722184T patent/DK1373255T3/da active
- 2002-03-05 PL PL363263A patent/PL208238B1/pl unknown
- 2002-03-05 NZ NZ528620A patent/NZ528620A/en not_active IP Right Cessation
- 2002-03-05 MX MXPA03008205A patent/MXPA03008205A/es active IP Right Grant
- 2002-03-05 EA EA200300998A patent/EA006770B1/ru not_active IP Right Cessation
- 2002-03-05 EE EEP200300442A patent/EE05247B1/xx unknown
- 2002-03-05 DE DE60202755T patent/DE60202755T2/de not_active Expired - Lifetime
- 2002-03-05 PT PT02722184T patent/PT1373255E/pt unknown
- 2002-03-05 JP JP2002571490A patent/JP4257698B2/ja not_active Expired - Lifetime
- 2002-03-05 SI SI200230100T patent/SI1373255T1/xx unknown
- 2002-03-05 KR KR1020037010091A patent/KR100849042B1/ko not_active Expired - Lifetime
- 2002-03-05 CA CA2438421A patent/CA2438421C/en not_active Expired - Lifetime
- 2002-03-05 CZ CZ20032704A patent/CZ300622B6/cs not_active IP Right Cessation
- 2002-03-05 CN CNB02806335XA patent/CN1246318C/zh not_active Expired - Lifetime
- 2002-03-05 IL IL15783902A patent/IL157839A0/xx unknown
- 2002-03-05 WO PCT/EP2002/002459 patent/WO2002072574A1/en not_active Ceased
- 2002-03-05 AU AU2002253101A patent/AU2002253101B2/en not_active Expired
- 2002-03-11 AR ARP020100873A patent/AR035944A1/es active IP Right Grant
- 2002-03-11 TW TW091104444A patent/TWI249532B/zh not_active IP Right Cessation
- 2002-03-11 MY MYPI20020866A patent/MY124838A/en unknown
- 2002-05-03 UA UA2003087776A patent/UA74871C2/uk unknown
2003
- 2003-09-10 IL IL157839A patent/IL157839A/en unknown
- 2003-09-10 NO NO20034003A patent/NO324954B1/no not_active IP Right Cessation
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Also Published As

Publication number	Publication date
US6844439B2 (en)	2005-01-18
HK1063315A1 (zh)	2004-12-24
EP1373255A1 (de)	2004-01-02
EE05247B1 (et)	2009-12-15
PT1373255E (pt)	2005-05-31
EP1373255B1 (de)	2005-01-26
BR0208075A (pt)	2004-03-02
DE60202755T2 (de)	2006-03-30
IL157839A (en)	2008-07-08
SK12462003A3 (sk)	2004-06-08
SK287807B6 (sk)	2011-10-04
HUP0303443A3 (en)	2012-09-28
WO2002072574A1 (en)	2002-09-19
NO20034003L (no)	2003-10-22
CA2438421C (en)	2010-05-18
EA200300998A1 (ru)	2004-02-26
EA006770B1 (ru)	2006-04-28
TWI249532B (en)	2006-02-21
HU230282B1 (hu)	2015-12-28
CA2438421A1 (en)	2002-09-19
NO20034003D0 (no)	2003-09-10
JP4257698B2 (ja)	2009-04-22
KR100849042B1 (ko)	2008-07-29
MXPA03008205A (es)	2004-01-29
CZ20032704A3 (en)	2004-03-17
AR035944A1 (es)	2004-07-28
BRPI0208075B8 (pt)	2021-05-25
US20040138256A1 (en)	2004-07-15
KR20030079971A (ko)	2003-10-10
CN1496363A (zh)	2004-05-12
CZ300622B6 (cs)	2009-07-01
DK1373255T3 (da)	2005-05-23
ZA200307117B (en)	2004-09-13
ES2236505T3 (es)	2005-07-16
NO324954B1 (no)	2008-01-14
SI1373255T1 (de)	2005-08-31
DE60202755D1 (de)	2005-03-03
HUP0303443A2 (hu)	2004-01-28
PL208238B1 (pl)	2011-04-29
JP2004523575A (ja)	2004-08-05
NZ528620A (en)	2005-01-28
EE200300442A (et)	2003-12-15
AU2002253101B2 (en)	2007-08-09
HRP20030695B1 (hr)	2011-07-31
MY124838A (en)	2006-07-31
PL363263A1 (en)	2004-11-15
IL157839A0 (en)	2004-03-28
ATE287882T1 (de)	2005-02-15
BRPI0208075B1 (pt)	2018-02-14
HRP20030695A2 (en)	2005-02-28
CN1246318C (zh)	2006-03-22

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