IL124572A - History of compressed imidazole acting as modulators of drug resistance, preparation and pharmaceutical preparations containing them - Google Patents

History of compressed imidazole acting as modulators of drug resistance, preparation and pharmaceutical preparations containing them

Info

Publication number: IL124572A
Authority: IL; Israel
Prior art keywords: formula; alkyl; alkyloxy; compound; hydrogen
Prior art date: 1996-03-19

Application number

IL12457297A

Other languages

English (en)

Hebrew (he)

Other versions

IL124572A0 (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.)

1996-03-19

Filing date

1997-03-11

Publication date

2002-03-10

1997-03-11 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1997-03-11 Priority to IL14399897A priority Critical patent/IL143998A/xx

1998-12-06 Publication of IL124572A0 publication Critical patent/IL124572A0/xx

2001-06-26 Priority to IL14399797A priority patent/IL143997A/xx

2002-03-10 Publication of IL124572A publication Critical patent/IL124572A/en

Links

238000002360 preparation method Methods 0.000 title claims description 15
239000008194 pharmaceutical composition Substances 0.000 title claims description 10
230000036457 multidrug resistance Effects 0.000 title description 26
150000002460 imidazoles Chemical class 0.000 title description 3
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 139
239000001257 hydrogen Substances 0.000 claims abstract description 50
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 39
125000003545 alkoxy group Chemical group 0.000 claims abstract description 30
150000002431 hydrogen Chemical group 0.000 claims abstract description 27
150000003839 salts Chemical class 0.000 claims abstract description 26
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 18
125000001424 substituent group Chemical group 0.000 claims abstract description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
125000002971 oxazolyl group Chemical group 0.000 claims abstract description 10
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 10
125000002883 imidazolyl group Chemical group 0.000 claims abstract description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
125000002541 furyl group Chemical group 0.000 claims abstract description 6
125000001475 halogen functional group Chemical group 0.000 claims abstract 19
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 4
125000000335 thiazolyl group Chemical group 0.000 claims abstract 4
239000000203 mixture Substances 0.000 claims description 81
-1 pyridinyl quinolinyl Chemical group 0.000 claims description 50
239000002904 solvent Substances 0.000 claims description 37
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 24
238000011282 treatment Methods 0.000 claims description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
239000002585 base Substances 0.000 claims description 20
238000000034 method Methods 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 15
239000002246 antineoplastic agent Substances 0.000 claims description 14
239000012442 inert solvent Substances 0.000 claims description 11
244000052769 pathogen Species 0.000 claims description 9
239000003937 drug carrier Substances 0.000 claims description 8
150000001204 N-oxides Chemical class 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
239000003153 chemical reaction reagent Substances 0.000 claims description 6
239000008177 pharmaceutical agent Substances 0.000 claims description 6
229940034982 antineoplastic agent Drugs 0.000 claims description 4
OTKFCIVOVKCFHR-UHFFFAOYSA-N (Methylsulfinyl)(methylthio)methane Chemical compound CSCS(C)=O OTKFCIVOVKCFHR-UHFFFAOYSA-N 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
230000000118 anti-neoplastic effect Effects 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000007800 oxidant agent Substances 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 4
125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
125000000815 N-oxide group Chemical group 0.000 abstract 1
125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 89
239000000543 intermediate Substances 0.000 description 66
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 28
229910001868 water Inorganic materials 0.000 description 28
125000005843 halogen group Chemical group 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
239000012044 organic layer Substances 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000002244 precipitate Substances 0.000 description 18
150000003254 radicals Chemical class 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
239000003480 eluent Substances 0.000 description 15
235000019441 ethanol Nutrition 0.000 description 15
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 15
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
206010028980 Neoplasm Diseases 0.000 description 13
239000010410 layer Substances 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
229940127089 cytotoxic agent Drugs 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 8
239000011521 glass Substances 0.000 description 8
239000003826 tablet Substances 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
239000000824 cytostatic agent Substances 0.000 description 7
230000001085 cytostatic effect Effects 0.000 description 7
230000000694 effects Effects 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 7
235000015320 potassium carbonate Nutrition 0.000 description 7
238000010992 reflux Methods 0.000 description 7
YGLDQFWPUCURIP-UHFFFAOYSA-N 3h-3-benzazepine Chemical compound C1=CNC=CC2=CC=CC=C21 YGLDQFWPUCURIP-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
201000011510 cancer Diseases 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
201000010099 disease Diseases 0.000 description 6
230000004083 survival effect Effects 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
229940079593 drug Drugs 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
238000007126 N-alkylation reaction Methods 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
229940125782 compound 2 Drugs 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
230000002140 halogenating effect Effects 0.000 description 4
208000032839 leukemia Diseases 0.000 description 4
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
230000002441 reversible effect Effects 0.000 description 4
238000003756 stirring Methods 0.000 description 4
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
239000000725 suspension Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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 3
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
101000740112 Homo sapiens Membrane-associated transporter protein Proteins 0.000 description 3
102100037258 Membrane-associated transporter protein Human genes 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000000654 additive Substances 0.000 description 3
230000003266 anti-allergic effect Effects 0.000 description 3
235000019400 benzoyl peroxide Nutrition 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
238000002512 chemotherapy Methods 0.000 description 3
231100000433 cytotoxic Toxicity 0.000 description 3
230000001472 cytotoxic effect Effects 0.000 description 3
108010037444 diisopropylglutathione ester Proteins 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
230000010534 mechanism of action Effects 0.000 description 3
229910000069 nitrogen hydride Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
125000004076 pyridyl group Chemical group 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
229930192474 thiophene Natural products 0.000 description 3
XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 description 2
VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 2
WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 2
WDETYCRYUBGKCE-UHFFFAOYSA-N 2-(chloromethyl)quinolin-1-ium;chloride Chemical compound Cl.C1=CC=CC2=NC(CCl)=CC=C21 WDETYCRYUBGKCE-UHFFFAOYSA-N 0.000 description 2
DDEAEWMDOSXKBX-UHFFFAOYSA-N 2-(chloromethyl)quinoline Chemical compound C1=CC=CC2=NC(CCl)=CC=C21 DDEAEWMDOSXKBX-UHFFFAOYSA-N 0.000 description 2
MGDNFZAPRFRURE-UHFFFAOYSA-N 2-[3-(quinolin-2-ylmethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=CC(OCC=2N=C3C=CC=CC3=CC=2)=C1 MGDNFZAPRFRURE-UHFFFAOYSA-N 0.000 description 2
HQVRLBYYRRAXFL-UHFFFAOYSA-N 2-[4-(quinolin-2-ylmethoxy)phenyl]ethanol Chemical compound C1=CC(CCO)=CC=C1OCC1=CC=C(C=CC=C2)C2=N1 HQVRLBYYRRAXFL-UHFFFAOYSA-N 0.000 description 2
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ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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239000011734 sodium Substances 0.000 description 1
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ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
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KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 1
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MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/04—Amoebicides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Tropical Medicine & Parasitology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Pulmonology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Plural Heterocyclic Compounds (AREA)

IL12457297A 1996-03-19 1997-03-11 History of compressed imidazole acting as modulators of drug resistance, preparation and pharmaceutical preparations containing them IL124572A (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
IL14399897A IL143998A (en)	1996-03-19	1997-03-11	(het)aryl (alk) oxyphenylalkanol ester intermediates for fused imidazole derivatives and a process for their preparation
IL14399797A IL143997A (en)	1996-03-19	2001-06-26	Multidrug resistance modulating fused tricylic imidazole derivatives, their preparation and pharmaceutical compositions containing them

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP96200755		1996-03-19
PCT/EP1997/001264 WO1997034897A1 (en)	1996-03-19	1997-03-11	Fused imidazole derivatives as multidrug resistance modulators

Publications (2)

Publication Number	Publication Date
IL124572A0 IL124572A0 (en)	1998-12-06
IL124572A true IL124572A (en)	2002-03-10

Family

ID=8223797

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12457297A IL124572A (en)	1996-03-19	1997-03-11	History of compressed imidazole acting as modulators of drug resistance, preparation and pharmaceutical preparations containing them

Country Status (29)

Country	Link
US (3)	US6218381B1 (de)
EP (1)	EP0888352B1 (de)
JP (3)	JP3630434B2 (de)
KR (2)	KR100330698B1 (de)
CN (1)	CN1083453C (de)
AR (1)	AR006271A1 (de)
AT (1)	ATE241626T1 (de)
BG (1)	BG62734B1 (de)
BR (1)	BR9708140A (de)
CA (1)	CA2237594C (de)
CZ (1)	CZ294060B6 (de)
DE (1)	DE69722389T2 (de)
EA (1)	EA001004B1 (de)
EE (1)	EE03773B1 (de)
ES (1)	ES2200159T3 (de)
HR (1)	HRP970161B1 (de)
HU (1)	HU224528B1 (de)
ID (1)	ID16375A (de)
IL (1)	IL124572A (de)
MX (1)	MX9804426A (de)
MY (1)	MY118282A (de)
NO (1)	NO310659B1 (de)
NZ (1)	NZ330466A (de)
PL (1)	PL193444B1 (de)
SK (1)	SK284434B6 (de)
TR (1)	TR199801191T2 (de)
TW (1)	TW527186B (de)
WO (1)	WO1997034897A1 (de)
ZA (1)	ZA972351B (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6544979B1 (en)	1997-09-18	2003-04-08	Janssen Pharmaceuticals, N.V.	Fused imidazole derivatives for improving oral bioavailability of pharmaceutical agents
WO1999049848A1 (en) *	1998-04-01	1999-10-07	Rtp Pharma Inc.	Anticancer compositions
US6743794B2 (en)	1999-12-22	2004-06-01	Eli Lilly And Company	Methods and compounds for inhibiting MRP1
US6376514B1 (en)	2000-10-17	2002-04-23	The Procter & Gamble Co.	Substituted six-membered heterocyclic compounds useful for treating multidrug resistance and compositions and methods thereof
US6693099B2 (en)	2000-10-17	2004-02-17	The Procter & Gamble Company	Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance
US7476662B2 (en)	2001-06-12	2009-01-13	Janssen Pharmaceutica N.V.	Substituted tetracyclic imidazole derivatives, processes for their preparation, pharmaceutical compositions comprising them and their use as a medicine
CA2690483C (en) *	2001-11-23	2012-07-24	Janssen Pharmaceutica N.V.	The use of anti-histaminics for acute reduction of elevated intracranial pressure
GB0301736D0 (en) *	2003-01-24	2003-02-26	Xenova Ltd	Pharmaceutical compounds
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1997
- 1997-03-05 TW TW086102623A patent/TW527186B/zh not_active IP Right Cessation
- 1997-03-11 KR KR1019980703754A patent/KR100330698B1/ko not_active Expired - Fee Related
- 1997-03-11 CN CN97192399A patent/CN1083453C/zh not_active Expired - Fee Related
- 1997-03-11 KR KR1020017008287A patent/KR100349500B1/ko not_active Expired - Fee Related
- 1997-03-11 ES ES97908226T patent/ES2200159T3/es not_active Expired - Lifetime
- 1997-03-11 EE EE9800281A patent/EE03773B1/xx not_active IP Right Cessation
- 1997-03-11 EA EA199800586A patent/EA001004B1/ru unknown
- 1997-03-11 AT AT97908226T patent/ATE241626T1/de not_active IP Right Cessation
- 1997-03-11 PL PL97327985A patent/PL193444B1/pl not_active IP Right Cessation
- 1997-03-11 BR BR9708140A patent/BR9708140A/pt not_active IP Right Cessation
- 1997-03-11 US US09/142,932 patent/US6218381B1/en not_active Expired - Fee Related
- 1997-03-11 HU HU9900415A patent/HU224528B1/hu not_active IP Right Cessation
- 1997-03-11 EP EP97908226A patent/EP0888352B1/de not_active Expired - Lifetime
- 1997-03-11 CZ CZ19981529A patent/CZ294060B6/cs not_active IP Right Cessation
- 1997-03-11 DE DE69722389T patent/DE69722389T2/de not_active Expired - Fee Related
- 1997-03-11 SK SK662-98A patent/SK284434B6/sk not_active IP Right Cessation
- 1997-03-11 IL IL12457297A patent/IL124572A/en not_active IP Right Cessation
- 1997-03-11 WO PCT/EP1997/001264 patent/WO1997034897A1/en not_active Ceased
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- 1997-03-11 NZ NZ330466A patent/NZ330466A/xx unknown
- 1997-03-11 TR TR1998/01191T patent/TR199801191T2/xx unknown
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- 1997-03-18 ZA ZA972351A patent/ZA972351B/xx unknown
- 1997-03-18 AR ARP970101072A patent/AR006271A1/es unknown
- 1997-03-19 ID IDP970888A patent/ID16375A/id unknown
- 1997-03-19 HR HR970161A patent/HRP970161B1/xx not_active IP Right Cessation
1998
- 1998-05-11 NO NO19982124A patent/NO310659B1/no not_active IP Right Cessation
- 1998-05-18 BG BG102459A patent/BG62734B1/bg unknown
- 1998-06-03 MX MX9804426A patent/MX9804426A/es not_active IP Right Cessation
2001
- 2001-02-02 US US09/775,524 patent/US6476018B1/en not_active Expired - Fee Related
- 2001-06-01 JP JP2001167003A patent/JP4205319B2/ja not_active Expired - Fee Related
2002
- 2002-07-02 US US10/187,665 patent/US20030087895A1/en not_active Abandoned
2003
- 2003-10-08 JP JP2003349802A patent/JP4251447B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
BG62734B1 (bg)	2000-06-30
NO982124L (no)	1998-09-18
JP2000505477A (ja)	2000-05-09
JP4251447B2 (ja)	2009-04-08
HUP9900415A3 (en)	2001-11-28
CN1211985A (zh)	1999-03-24
CA2237594A1 (en)	1997-09-25
AR006271A1 (es)	1999-08-11
CN1083453C (zh)	2002-04-24
SK284434B6 (sk)	2005-04-01
CZ294060B6 (cs)	2004-09-15
JP2002012594A (ja)	2002-01-15
KR20000064358A (ko)	2000-11-06
AU2026997A (en)	1997-10-10
PL327985A1 (en)	1999-01-04
CZ152998A3 (cs)	1999-02-17
US6218381B1 (en)	2001-04-17
HRP970161A2 (en)	1998-04-30
DE69722389T2 (de)	2009-09-24
NO310659B1 (no)	2001-08-06
BG102459A (en)	1999-06-30
CA2237594C (en)	2006-05-30
US6476018B1 (en)	2002-11-05
AU709683B2 (en)	1999-09-02
EP0888352B1 (de)	2003-05-28
KR100349500B1 (ko)	2002-08-21
JP4205319B2 (ja)	2009-01-07
EA001004B1 (ru)	2000-08-28
HRP970161B1 (en)	2002-06-30
EP0888352A1 (de)	1999-01-07
HUP9900415A2 (hu)	1999-05-28
HK1015769A1 (en)	1999-10-22
MX9804426A (es)	1998-09-30
HU224528B1 (hu)	2005-10-28
IL124572A0 (en)	1998-12-06
ATE241626T1 (de)	2003-06-15
NZ330466A (en)	1999-03-29
KR100330698B1 (ko)	2002-10-31
ID16375A (id)	1997-09-25
BR9708140A (pt)	1999-07-27
JP3630434B2 (ja)	2005-03-16
EE9800281A (et)	1999-02-15
PL193444B1 (pl)	2007-02-28
DE69722389D1 (de)	2003-07-03
NO982124D0 (no)	1998-05-11
EE03773B1 (et)	2002-06-17
TW527186B (en)	2003-04-11
WO1997034897A1 (en)	1997-09-25
MY118282A (en)	2004-09-30
US20030087895A1 (en)	2003-05-08
SK66298A3 (en)	1999-06-11
TR199801191T2 (xx)	1998-10-21
ES2200159T3 (es)	2004-03-01
ZA972351B (en)	1998-09-18
EA199800586A1 (ru)	1998-12-24
JP2004067701A (ja)	2004-03-04

Legal Events

Date	Code	Title
2002-08-14	FF	Patent granted
2002-08-14	KB	Patent renewed
2003-05-29	KB	Patent renewed
2007-06-17	KB	Patent renewed
2011-12-29	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
JP4272262B2 (ja)	2009-06-03	ファルネシルトランスフェラーゼ阻害性ｎまたはｃ結合イミダゾール置換１，８−環付加キノリノン誘導体
EP4310091A1 (de)	2024-01-24	Pyrimidinkondensierte cyclische verbindung, herstellungsverfahren dafür und verwendung davon
IL124572A (en)	2002-03-10	History of compressed imidazole acting as modulators of drug resistance, preparation and pharmaceutical preparations containing them
NZ527741A (en)	2005-02-25	Pyridopyrimidine or naphthyridine derivative
US6544979B1 (en)	2003-04-08	Fused imidazole derivatives for improving oral bioavailability of pharmaceutical agents
EP0672047B1 (de)	2003-05-02	ANTIALLERGISCHE IMIDAZO[1,2-a]THIENO[2,3-d]AZEPINDERIVATE
AU709683C (en)	2000-05-18	Fused imidazole derivatives as multidrug resistance modulators
HK1015769B (en)	2003-09-26	Fused imidazole derivatives as multidrug resistance modulators
HK1024689B (en)	2004-03-05	Farnesyl transferase inhibiting 1,8-annelated quinolinone derivatives substituted with n- or c-linked imidazoles