IL133212A - History of use (imidazolil-5-yl) methyl-2-quinolinone that act as culture inhibitors of smooth muscle cells - Google Patents

History of use (imidazolil-5-yl) methyl-2-quinolinone that act as culture inhibitors of smooth muscle cells

Info

Publication number: IL133212A
Authority: IL; Israel
Prior art keywords: sub; 6alkyl; sup; alkyl; hydrogen
Prior art date: 1997-06-02

Application number

IL13321298A

Other languages

English (en)

Hebrew (he)

Other versions

IL133212A0 (en

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.)

1997-06-02

Filing date

1998-05-25

Publication date

2005-12-18

1998-05-25 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2001-03-19 Publication of IL133212A0 publication Critical patent/IL133212A0/xx

2005-12-18 Publication of IL133212A publication Critical patent/IL133212A/en

Links

210000000329 smooth muscle myocyte Anatomy 0.000 title claims abstract description 23
230000004663 cell proliferation Effects 0.000 title claims abstract description 14
AVGQUILLCRPWKH-UHFFFAOYSA-N 4-(1h-imidazol-5-yl)-3-methyl-1h-quinolin-2-one Chemical class C12=CC=CC=C2NC(=O)C(C)=C1C1=CN=CN1 AVGQUILLCRPWKH-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 136
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 80
239000001257 hydrogen Substances 0.000 claims abstract description 79
-1 amino, hydroxycarbonyl Chemical group 0.000 claims abstract description 62
150000002431 hydrogen Chemical class 0.000 claims abstract description 49
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 27
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
239000001301 oxygen Substances 0.000 claims abstract description 11
229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
239000003814 drug Substances 0.000 claims abstract description 10
125000002883 imidazolyl group Chemical group 0.000 claims abstract description 8
238000004519 manufacturing process Methods 0.000 claims abstract description 6
125000004951 trihalomethoxy group Chemical group 0.000 claims abstract description 6
125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052717 sulfur Chemical group 0.000 claims abstract description 4
239000011593 sulfur Chemical group 0.000 claims abstract description 4
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract description 3
125000001475 halogen functional group Chemical group 0.000 claims abstract 13
239000002253 acid Substances 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 18
208000037803 restenosis Diseases 0.000 claims description 17
238000000576 coating method Methods 0.000 claims description 16
239000011248 coating agent Substances 0.000 claims description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
230000002062 proliferating effect Effects 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
230000002792 vascular Effects 0.000 claims description 10
239000000463 material Substances 0.000 claims description 9
150000001413 amino acids Chemical class 0.000 claims description 7
238000007887 coronary angioplasty Methods 0.000 claims description 6
201000001320 Atherosclerosis Diseases 0.000 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
210000004351 coronary vessel Anatomy 0.000 claims description 5
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
PLHJCIYEEKOWNM-UHFFFAOYSA-N 6-[amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2-one Chemical compound CN1C=NC=C1C(N)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)N(C)C2=CC=1)C1=CC=C(Cl)C=C1 PLHJCIYEEKOWNM-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 34
125000003545 alkoxy group Chemical group 0.000 abstract 9
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 4
125000003342 alkenyl group Chemical group 0.000 abstract 1
125000004414 alkyl thio group Chemical group 0.000 abstract 1
239000000203 mixture Substances 0.000 description 102
239000000543 intermediate Substances 0.000 description 68
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 47
239000002904 solvent Substances 0.000 description 44
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 40
239000000243 solution Substances 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
229910001868 water Inorganic materials 0.000 description 33
239000012044 organic layer Substances 0.000 description 29
239000002244 precipitate Substances 0.000 description 28
239000003480 eluent Substances 0.000 description 26
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000000741 silica gel Substances 0.000 description 23
229910002027 silica gel Inorganic materials 0.000 description 23
238000004440 column chromatography Methods 0.000 description 22
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
238000000034 method Methods 0.000 description 20
239000002585 base Substances 0.000 description 19
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
150000003254 radicals Chemical class 0.000 description 17
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
239000000047 product Substances 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
125000005843 halogen group Chemical group 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
210000001367 artery Anatomy 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
235000011114 ammonium hydroxide Nutrition 0.000 description 11
125000001309 chloro group Chemical group Cl* 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
238000000746 purification Methods 0.000 description 10
238000003756 stirring Methods 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
108010037444 diisopropylglutathione ester Proteins 0.000 description 9
208000035475 disorder Diseases 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
238000002399 angioplasty Methods 0.000 description 8
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
GHQPBDDZGPAVJP-UHFFFAOYSA-N azanium;methanol;hydroxide Chemical compound N.O.OC GHQPBDDZGPAVJP-UHFFFAOYSA-N 0.000 description 7
125000000524 functional group Chemical group 0.000 description 7
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
239000010410 layer Substances 0.000 description 7
239000011591 potassium Substances 0.000 description 7
229910052700 potassium Inorganic materials 0.000 description 7
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 7
230000009466 transformation Effects 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 6
229940024606 amino acid Drugs 0.000 description 6
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
229930185107 quinolinone Natural products 0.000 description 6
238000012360 testing method Methods 0.000 description 6
210000001519 tissue Anatomy 0.000 description 6
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 5
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
229960005235 piperonyl butoxide Drugs 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000000560 biocompatible material Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
229920000137 polyphosphoric acid Polymers 0.000 description 4
229920001296 polysiloxane Polymers 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000003826 tablet Substances 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000000654 additive Substances 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
239000003527 fibrinolytic agent Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
230000006715 negative regulation of smooth muscle cell proliferation Effects 0.000 description 3
150000001282 organosilanes Chemical class 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
229920000052 poly(p-xylylene) Chemical class 0.000 description 3
235000015320 potassium carbonate Nutrition 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000000844 transformation Methods 0.000 description 3
IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 2
IKMMPHALUZQNMN-UHFFFAOYSA-N 3-(1h-imidazol-5-ylmethyl)-1h-quinolin-2-one Chemical class O=C1NC2=CC=CC=C2C=C1CC1=CN=CN1 IKMMPHALUZQNMN-UHFFFAOYSA-N 0.000 description 2
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
239000004475 Arginine Substances 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
208000037260 Atherosclerotic Plaque Diseases 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
239000004472 Lysine Substances 0.000 description 2
238000007126 N-alkylation reaction Methods 0.000 description 2
229910017974 NH40H Inorganic materials 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
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208000007536 Thrombosis Diseases 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
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239000005557 antagonist Substances 0.000 description 2
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239000003054 catalyst Substances 0.000 description 2
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230000010339 dilation Effects 0.000 description 2
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150000002148 esters Chemical class 0.000 description 2
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
239000003102 growth factor Substances 0.000 description 2
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239000002609 medium Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 2
QYEMNJMSULGQRD-UHFFFAOYSA-N methyl-1H-quinolin-2-one Natural products C1=CC=C2C=CC(=O)N(C)C2=C1 QYEMNJMSULGQRD-UHFFFAOYSA-N 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 2
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239000002245 particle Substances 0.000 description 1
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235000019371 penicillin G benzathine Nutrition 0.000 description 1
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UWCVGPLTGZWHGS-ZORIOUSZSA-N pergolide mesylate Chemical compound CS(O)(=O)=O.C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 UWCVGPLTGZWHGS-ZORIOUSZSA-N 0.000 description 1
229960001511 pergolide mesylate Drugs 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
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229910052697 platinum Inorganic materials 0.000 description 1
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239000004810 polytetrafluoroethylene Substances 0.000 description 1
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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238000006862 quantum yield reaction Methods 0.000 description 1
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239000002516 radical scavenger Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
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150000004492 retinoid derivatives Chemical class 0.000 description 1
230000000250 revascularization Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
210000003752 saphenous vein Anatomy 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000004544 spot-on Substances 0.000 description 1
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235000019698 starch Nutrition 0.000 description 1
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230000000707 stereoselective effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000002731 stomach secretion inhibitor Substances 0.000 description 1
229960005202 streptokinase Drugs 0.000 description 1
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235000000346 sugar Nutrition 0.000 description 1
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238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229920002725 thermoplastic elastomer Polymers 0.000 description 1
239000003868 thrombin inhibitor Substances 0.000 description 1
230000009424 thromboembolic effect Effects 0.000 description 1
229960000103 thrombolytic agent Drugs 0.000 description 1
229960000187 tissue plasminogen activator Drugs 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
229960000984 tocofersolan Drugs 0.000 description 1
239000003558 transferase inhibitor Substances 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

IL13321298A 1997-06-02 1998-05-25 History of use (imidazolil-5-yl) methyl-2-quinolinone that act as culture inhibitors of smooth muscle cells IL133212A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US4737697P	1997-06-02	1997-06-02
PCT/EP1998/003182 WO1998055124A1 (en)	1997-06-02	1998-05-25	(imidazol-5-yl)methyl-2-quinolinone derivatives as inhibitors of smooth muscle cell proliferation

Publications (2)

Publication Number	Publication Date
IL133212A0 IL133212A0 (en)	2001-03-19
IL133212A true IL133212A (en)	2005-12-18

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ID=21948611

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Application Number	Title	Priority Date	Filing Date
IL13321298A IL133212A (en)	1997-06-02	1998-05-25	History of use (imidazolil-5-yl) methyl-2-quinolinone that act as culture inhibitors of smooth muscle cells

Country Status (21)

Country	Link
US (4)	US6365600B1 (da)
EP (1)	EP0988038B1 (da)
JP (1)	JP4209472B2 (da)
KR (1)	KR100517832B1 (da)
CN (2)	CN1231215C (da)
AT (1)	ATE222104T1 (da)
AU (1)	AU740603B2 (da)
BR (1)	BR9810423A (da)
CA (1)	CA2290992C (da)
DE (1)	DE69807222T2 (da)
DK (1)	DK0988038T3 (da)
ES (1)	ES2182327T3 (da)
ID (1)	ID24675A (da)
IL (1)	IL133212A (da)
NO (1)	NO318834B1 (da)
NZ (1)	NZ501401A (da)
PT (1)	PT988038E (da)
RU (1)	RU2209066C2 (da)
TR (1)	TR199902923T2 (da)
WO (1)	WO1998055124A1 (da)
ZA (1)	ZA984700B (da)

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1998
- 1998-05-25 ES ES98928332T patent/ES2182327T3/es not_active Expired - Lifetime
- 1998-05-25 NZ NZ501401A patent/NZ501401A/en not_active IP Right Cessation
- 1998-05-25 AU AU80207/98A patent/AU740603B2/en not_active Expired
- 1998-05-25 DE DE69807222T patent/DE69807222T2/de not_active Expired - Lifetime
- 1998-05-25 CA CA002290992A patent/CA2290992C/en not_active Expired - Lifetime
- 1998-05-25 PT PT98928332T patent/PT988038E/pt unknown
- 1998-05-25 DK DK98928332T patent/DK0988038T3/da active
- 1998-05-25 RU RU2000100032/14A patent/RU2209066C2/ru active
- 1998-05-25 TR TR1999/02923T patent/TR199902923T2/xx unknown
- 1998-05-25 CN CNB98805700XA patent/CN1231215C/zh not_active Expired - Lifetime
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- 1998-05-25 CN CNB2005101163581A patent/CN100525766C/zh not_active Expired - Lifetime
- 1998-05-25 JP JP50144099A patent/JP4209472B2/ja not_active Expired - Lifetime
- 1998-05-25 KR KR10-1999-7010744A patent/KR100517832B1/ko not_active Expired - Lifetime
- 1998-05-25 AT AT98928332T patent/ATE222104T1/de active
- 1998-05-25 WO PCT/EP1998/003182 patent/WO1998055124A1/en not_active Ceased
- 1998-05-25 BR BR9810423-3A patent/BR9810423A/pt not_active Application Discontinuation
- 1998-05-28 ID IDW991506A patent/ID24675A/id unknown
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1999
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2001
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2003
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Publication number	Publication date
AU740603B2 (en)	2001-11-08
DE69807222T2 (de)	2003-04-17
ATE222104T1 (de)	2002-08-15
PT988038E (pt)	2002-12-31
CN1265585A (zh)	2000-09-06
CA2290992A1 (en)	1998-12-10
AU8020798A (en)	1998-12-21
US6734194B2 (en)	2004-05-11
KR100517832B1 (ko)	2005-09-30
US6365600B1 (en)	2002-04-02
RU2209066C2 (ru)	2003-07-27
BR9810423A (pt)	2000-10-03
US20040198771A1 (en)	2004-10-07
US6743805B2 (en)	2004-06-01
NO995883D0 (no)	1999-12-01
NZ501401A (en)	2002-03-28
JP4209472B2 (ja)	2009-01-14
US7253183B2 (en)	2007-08-07
KR20010012782A (ko)	2001-02-26
WO1998055124A1 (en)	1998-12-10
ZA984700B (en)	1999-12-01
CN1231215C (zh)	2005-12-14
ID24675A (id)	2000-07-27
NO995883L (no)	2000-02-02
US20030229118A1 (en)	2003-12-11
TR199902923T2 (xx)	2000-11-21
CA2290992C (en)	2008-02-12
CN1762355A (zh)	2006-04-26
CN100525766C (zh)	2009-08-12
ES2182327T3 (es)	2003-03-01
HK1025046A1 (en)	2000-11-03
NO318834B1 (no)	2005-05-09
JP2002503235A (ja)	2002-01-29
IL133212A0 (en)	2001-03-19
EP0988038A1 (en)	2000-03-29
EP0988038B1 (en)	2002-08-14
DE69807222D1 (de)	2002-09-19
DK0988038T3 (da)	2002-12-02
HK1088820A1 (zh)	2006-11-17
US20020091138A1 (en)	2002-07-11

Publication	Publication Date	Title
EP0988038B1 (en)	2002-08-14	(imidazol-5-yl)methyl-2-quinolinone derivatives as inhibitors of smooth muscle cell proliferation
US6169096B1 (en)	2001-01-02	Farnesyl protein transferase inhibiting (imidazol-5-yl)methyl-2-quinolinone derivatives
JP2003525234A (ja)	2003-08-26	カンプトテシン化合物とのファルネシルタンパク質トランスフェラーゼ阻害剤の組み合わせ剤
JP2003525239A (ja)	2003-08-26	タキサン化合物とのファルネシルタンパク質トランスフェラーゼ阻害剤の組み合わせ剤
US20040157882A1 (en)	2004-08-12	Method of use of (imidazol-5-yl)methyl-2-quinolinone derivatives to inhibit smooth muscle cell proliferation
HK1025046B (en)	2002-12-20	(imidazol-5-yl)methyl-2-quinolinone derivatives as inhibitors of smooth muscle cell proliferation
MXPA99011128A (en)	2001-12-04	(imidazol-5-yl)methyl-2-quinolinone derivatives as inhibitors of smooth muscle cell proliferation
HK1088820B (en)	2010-03-12	(imidazol-5-yl)methyl-2-quinolinone derivatives as inhibitors of smooth muscle cell proliferation
PL190618B1 (pl)	2005-12-30	Zastosowanie (+)-6-[amino-(4-chlorofenylo) (1 -metylo-1 H-imidazol-5-ilo)metylo]-4-(3-chlorofenylo)-1-metylo-2(1H)-chinolinonu lub jego farmaceutycznie dopuszczalnej soli addycyjnej z kwasem
HK1012188B (en)	2002-07-26	Farnesyl protein transferase inhibiting (imidazol-5-yl) methyl-2-quinolinone derivatives

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2018-12-31	EXP	Patent expired