SK146699A3 - Benzimidazole derivative - Google Patents

Benzimidazole derivative Download PDF

Info

Publication number: SK146699A3
Authority: SK; Slovakia
Prior art keywords: group; phenyl; butyl; chme; propyl
Prior art date: 1997-05-01

Application number

SK1466-99A

Other languages

English (en)

Slovak (sk)

Inventor

Keizo Tanikawa

Yoshimasa Kamikawaji

Mitsuaki Hirotsuka

Takehisa Iwama

Akiko Yamamoto

Yoichiro Fujita

Original Assignee

Nissan Chemical Ind Ltd

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.)

1997-05-01

Filing date

1998-04-30

Publication date

2000-05-16

1998-04-30 Application filed by Nissan Chemical Ind Ltd filed Critical Nissan Chemical Ind Ltd

2000-05-16 Publication of SK146699A3 publication Critical patent/SK146699A3/sk

Links

125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 36
125000002947 alkylene group Chemical class 0.000 claims abstract description 24
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
125000000217 alkyl group Chemical class 0.000 claims abstract description 15
125000005843 halogen group Chemical group 0.000 claims abstract description 9
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 267
-1 2-trifluoromethylphenyl Chemical group 0.000 claims description 169
239000000203 mixture Substances 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 5
206010020751 Hypersensitivity Diseases 0.000 claims description 5
230000007815 allergy Effects 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 3
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims description 3
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
WLYPBMBWKYALCG-UHFFFAOYSA-N [2,4-bis(trifluoromethyl)phenyl]boronic acid Chemical group OB(O)C1=CC=C(C(F)(F)F)C=C1C(F)(F)F WLYPBMBWKYALCG-UHFFFAOYSA-N 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 claims description 2
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 2
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 5
125000004434 sulfur atom Chemical group 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 63
239000002904 solvent Substances 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
238000000034 method Methods 0.000 description 19
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 15
230000000052 comparative effect Effects 0.000 description 14
238000002360 preparation method Methods 0.000 description 14
239000007858 starting material Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000000460 chlorine Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 description 10
102100024304 Protachykinin-1 Human genes 0.000 description 10
101800003906 Substance P Proteins 0.000 description 10
239000002775 capsule Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
150000001556 benzimidazoles Chemical class 0.000 description 9
125000001309 chloro group Chemical group Cl* 0.000 description 8
235000019441 ethanol Nutrition 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000000243 solution Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000009472 formulation Methods 0.000 description 7
229960001340 histamine Drugs 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000007924 injection Substances 0.000 description 6
238000002347 injection Methods 0.000 description 6
230000004044 response Effects 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
239000000739 antihistaminic agent Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
230000001684 chronic effect Effects 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000003814 drug Substances 0.000 description 5
230000002140 halogenating effect Effects 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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239000002253 acid Substances 0.000 description 4
239000000043 antiallergic agent Substances 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
230000008602 contraction Effects 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
230000026030 halogenation Effects 0.000 description 4
238000005658 halogenation reaction Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
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235000011181 potassium carbonates Nutrition 0.000 description 4
239000000829 suppository Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
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WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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229910052740 iodine Inorganic materials 0.000 description 3
239000008101 lactose Substances 0.000 description 3
CWWARWOPSKGELM-SARDKLJWSA-N methyl (2s)-2-[[(2s)-2-[[2-[[(2s)-2-[[(2s)-2-[[(2s)-5-amino-2-[[(2s)-5-amino-2-[[(2s)-1-[(2s)-6-amino-2-[[(2s)-1-[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-5 Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)OC)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 CWWARWOPSKGELM-SARDKLJWSA-N 0.000 description 3
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
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OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
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229920000136 polysorbate Polymers 0.000 description 1
229950008882 polysorbate Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229940082004 sodium laurate Drugs 0.000 description 1
239000007787 solid Substances 0.000 description 1
WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical class C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
XKEDRBINPCQMOT-UHFFFAOYSA-N tert-butyl 2,3-diaminopropanoate Chemical compound CC(C)(C)OC(=O)C(N)CN XKEDRBINPCQMOT-UHFFFAOYSA-N 0.000 description 1
AOCSUUGBCMTKJH-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN AOCSUUGBCMTKJH-UHFFFAOYSA-N 0.000 description 1
YIMSPDZAVBIXRT-UHFFFAOYSA-N tert-butyl n-[3-(methylamino)propyl]carbamate Chemical compound CNCCCNC(=O)OC(C)(C)C YIMSPDZAVBIXRT-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
230000008728 vascular permeability Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/14—Radicals substituted by nitrogen atoms
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Immunology (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SK1466-99A 1997-05-01 1998-04-30 Benzimidazole derivative SK146699A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP11372397		1997-05-01
JP5530398		1998-03-06
PCT/JP1998/001986 WO1998050368A1 (en)	1997-05-01	1998-04-30	Benzimidazole derivative

Publications (1)

Publication Number	Publication Date
SK146699A3 true SK146699A3 (en)	2000-05-16

Family

ID=26396198

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1466-99A SK146699A3 (en)	1997-05-01	1998-04-30	Benzimidazole derivative

Country Status (15)

Country	Link
US (1)	US6114369A (zh)
EP (1)	EP0980359B1 (zh)
KR (1)	KR100530208B1 (zh)
CN (1)	CN1095836C (zh)
AT (1)	ATE269851T1 (zh)
AU (1)	AU730650B2 (zh)
CA (1)	CA2285535C (zh)
DE (1)	DE69824722T2 (zh)
HU (1)	HUP0001010A3 (zh)
IL (1)	IL132575A0 (zh)
NO (1)	NO995289D0 (zh)
NZ (1)	NZ337749A (zh)
RU (1)	RU2188822C2 (zh)
SK (1)	SK146699A3 (zh)
WO (1)	WO1998050368A1 (zh)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2002096853A1 (fr) *	2001-05-28	2002-12-05	Ihara Chemical Industry Co., Ltd.	Procede de production d'un derive d'aralkylamine
US7118765B2 (en)	2001-12-17	2006-10-10	Spi Pharma, Inc.	Co-processed carbohydrate system as a quick-dissolve matrix for solid dosage forms
US7419996B2 (en) *	2003-08-13	2008-09-02	The University Of Houston	Parenteral and oral formulations of benzimidazoles
US7291744B2 (en) *	2003-11-13	2007-11-06	Bristol-Myers Squibb Company	N-ureidoalkyl-amino compounds as modulators of chemokine receptor activity
US8617588B2 (en)	2009-03-09	2013-12-31	Spi Pharma, Inc.	Highly compactable and durable direct compression excipients and excipient systems
CN103121969A (zh) *	2012-12-04	2013-05-29	中国科学院昆明植物研究所	苯并咪唑及其衍生物，其药物组合物及其应用
CN103121970B (zh) *	2012-12-04	2015-04-29	中国科学院昆明植物研究所	苯并咪唑及其衍生物，其药物组合物及其在制备抗抑郁药物中的应用
RU2711098C1 (ru) *	2019-04-15	2020-01-15	Федеральное государственное бюджетное научное учреждение "Федеральный Ростовский аграрный научный центр" (ФГБНУ ФРАНЦ)	Производные нитропиридина, обладающие антибактериальной и протистоцидной активностью

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2244500B1 (zh) *	1973-07-03	1977-07-01	Delalande Sa
EP0144101B1 (en) *	1983-11-30	1991-02-06	Janssen Pharmaceutica N.V.	Bicyclic heterocyclyl containing n-(bicyclic heterocyclyl)-4-piperidinamines
US5290801A (en) *	1992-05-29	1994-03-01	The Du Pont Merck Pharmaceutical Company	Benzimidazoles for the treatment of atherosclerosis
JPH09124609A (ja) *	1995-11-07	1997-05-13	Nissan Chem Ind Ltd	ベンズイミダゾール誘導体

1998
- 1998-04-30 AU AU70830/98A patent/AU730650B2/en not_active Ceased
- 1998-04-30 KR KR10-1999-7009883A patent/KR100530208B1/ko not_active IP Right Cessation
- 1998-04-30 WO PCT/JP1998/001986 patent/WO1998050368A1/en not_active Application Discontinuation
- 1998-04-30 DE DE69824722T patent/DE69824722T2/de not_active Expired - Fee Related
- 1998-04-30 HU HU0001010A patent/HUP0001010A3/hu unknown
- 1998-04-30 IL IL13257598A patent/IL132575A0/xx unknown
- 1998-04-30 US US09/403,763 patent/US6114369A/en not_active Expired - Fee Related
- 1998-04-30 NZ NZ337749A patent/NZ337749A/xx unknown
- 1998-04-30 RU RU99125208/04A patent/RU2188822C2/ru not_active IP Right Cessation
- 1998-04-30 EP EP98917745A patent/EP0980359B1/en not_active Expired - Lifetime
- 1998-04-30 CA CA002285535A patent/CA2285535C/en not_active Expired - Fee Related
- 1998-04-30 SK SK1466-99A patent/SK146699A3/sk unknown
- 1998-04-30 AT AT98917745T patent/ATE269851T1/de not_active IP Right Cessation
- 1998-04-30 CN CN98804508A patent/CN1095836C/zh not_active Expired - Fee Related
1999
- 1999-10-29 NO NO995289A patent/NO995289D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
ATE269851T1 (de)	2004-07-15
AU730650B2 (en)	2001-03-08
CA2285535A1 (en)	1998-11-12
EP0980359A1 (en)	2000-02-23
RU2188822C2 (ru)	2002-09-10
DE69824722D1 (de)	2004-07-29
CA2285535C (en)	2006-08-15
IL132575A0 (en)	2001-03-19
US6114369A (en)	2000-09-05
KR20010020281A (ko)	2001-03-15
HUP0001010A3 (en)	2001-06-28
HUP0001010A2 (hu)	2001-04-28
WO1998050368A1 (en)	1998-11-12
AU7083098A (en)	1998-11-27
CN1095836C (zh)	2002-12-11
DE69824722T2 (de)	2004-12-09
KR100530208B1 (ko)	2005-11-22
NZ337749A (en)	2000-09-29
NO995289L (no)	1999-10-29
EP0980359B1 (en)	2004-06-23
NO995289D0 (no)	1999-10-29
CN1253549A (zh)	2000-05-17

Publication	Publication Date	Title
US6093735A (en)	2000-07-25	Selective β-3 adrenergic agonists
AU688120B2 (en)	1998-03-05	New piperidine compounds, process for their preparation and the pharmaceutical compositions which contain them
AU6621600A (en)	2001-03-05	Melanocortin-4 receptor binding compounds and methods of use thereof
WO1997020822A1 (en)	1997-06-12	Quinazolin-2,4-diazirines as npy receptor antagonist
WO1997020823A2 (en)	1997-06-12	2-amino quinazoline derivatives as npy receptor antagonists
JP2008526815A (ja)	2008-07-24	低コンダクタンスのカルシウム依存性カリウムチャネルのモジュレーターとしての新規２−アミノベンゾイミダゾール誘導体及びそれらの使用
US20120208821A1 (en)	2012-08-16	Alpha adrenergic receptor modulators
EP0775118B1 (en)	2003-06-04	Benzimidazole derivatives having dopaminergic activity
US6569880B2 (en)	2003-05-27	Bis(benzimidazole) derivatives serving as potassium blocking agents
SK146699A3 (en)	2000-05-16	Benzimidazole derivative
CA2311344C (en)	2006-02-07	5-(2-imidazolinylamino)-benzimidazole derivatives, their preparation and their use as .alpha.-adrenoceptor agonists with improved metabolic stability
AU2005313311A1 (en)	2006-06-15	Phenylpiperazine derivatives with a combination of partial dopamine-D2 receptor agonism and serotonin reuptake inhibition
US5889010A (en)	1999-03-30	Benzimidazole derivatives having dopaminergic activity
US6066740A (en)	2000-05-23	Process for making 2-amino-2-imidazoline, guanidine and 2-amino-3,4,5,6-tetrahydropyrimidine derivatives
JP4154541B2 (ja)	2008-09-24	ベンズイミダゾール誘導体
CZ336499A3 (cs)	2000-02-16	Benzimidazolové deriváty
AU2008286824B2 (en)	2014-10-02	Heterocyclyl substituted fused carbocyles useful in the treatment of conditions such as glaucoma and pain
SK69899A3 (en)	2000-01-18	Process for making 2-amino-2-imidazoline, guanidine, and 2-amino-3,4,5,6-tetrahydropyrimidine derivatives
AU2008286818B2 (en)	2014-03-27	Adrenergic compounds
KR20000071129A (ko)	2000-11-25	4-아미노알콕시-1ｈ-벤즈이미다졸 유도체, 이의 제조방법 및도파민 자가수용체(ｄ2) 효능제로서의 이의 용도
CZ20001912A3 (cs)	2000-11-15	5-(2-Imidazolinylamino)-benzimidazolové deriváty, jejich příprava a jejich použití jako alfa adrenoceptorové agonisty se zlepšenou metabolickou stálostí
AU1529999A (en)	1999-06-15	5-(2-imidazolinylamino)-benzimidazole derivatives, their preparation and their use as .alpha.-adrenoceptor agonists with improved metabolic stability
MXPA99004842A (en)	1999-09-01	Process for making 2-amino-2-imidazoline, guanidine, and 2-amino-3,4,5,6-tetrahydropyrimidine derivatives