JPH0567624B2 - - Google Patents
Info
- Publication number
- JPH0567624B2 JPH0567624B2 JP1173174A JP17317489A JPH0567624B2 JP H0567624 B2 JPH0567624 B2 JP H0567624B2 JP 1173174 A JP1173174 A JP 1173174A JP 17317489 A JP17317489 A JP 17317489A JP H0567624 B2 JPH0567624 B2 JP H0567624B2
- Authority
- JP
- Japan
- Prior art keywords
- integer
- benzimidazole
- group
- benzyl
- ethoxyethyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 6
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 230000001387 anti-histamine Effects 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000004175 fluorobenzyl group Chemical group 0.000 claims abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- -1 tetrahydrofurfuryl Chemical group 0.000 claims abstract description 4
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract 3
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000739 antihistaminic agent Substances 0.000 claims description 3
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 3
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 17
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 abstract description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- 238000000921 elemental analysis Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- GPTVQTPMFOLLOA-UHFFFAOYSA-N 1-chloro-2-ethoxyethane Chemical compound CCOCCCl GPTVQTPMFOLLOA-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
- JSADNMQUCMCSBS-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-n,n-dimethylpropan-1-amine Chemical compound C1=CC=C2NC(CCCN(C)C)=NC2=C1 JSADNMQUCMCSBS-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229960001412 pentobarbital Drugs 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000000742 histaminergic effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- GNJKPQRRYZIZHK-UHFFFAOYSA-N 3-[1-(2-ethoxyethyl)benzimidazol-2-yl]-n,n-dimethylpropan-1-amine Chemical compound C1=CC=C2N(CCOCC)C(CCCN(C)C)=NC2=C1 GNJKPQRRYZIZHK-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010010071 Coma Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000138 effect on histamine Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 2
- 229960000582 mepyramine Drugs 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 230000004622 sleep time Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- UGLCXJFGJZTCBU-UHFFFAOYSA-N 1-(1h-benzimidazol-2-yl)-5-(dimethylamino)pentan-1-one Chemical compound C1=CC=C2NC(C(=O)CCCCN(C)C)=NC2=C1 UGLCXJFGJZTCBU-UHFFFAOYSA-N 0.000 description 1
- MSRIVCVWSYCUJR-UHFFFAOYSA-N 1-(2-ethoxyethyl)-2-(3-piperidin-1-ylpropyl)benzimidazole Chemical compound N=1C2=CC=CC=C2N(CCOCC)C=1CCCN1CCCCC1 MSRIVCVWSYCUJR-UHFFFAOYSA-N 0.000 description 1
- AVFBCYKITFNXPW-UHFFFAOYSA-N 1-(2-ethoxyethyl)-2-(3-pyrrolidin-1-ylpropyl)benzimidazole Chemical compound N=1C2=CC=CC=C2N(CCOCC)C=1CCCN1CCCC1 AVFBCYKITFNXPW-UHFFFAOYSA-N 0.000 description 1
- IJXVXBFIGJLHPE-UHFFFAOYSA-N 1-(2-ethoxyethyl)-2-(4-piperidin-1-ylbutyl)benzimidazole Chemical compound N=1C2=CC=CC=C2N(CCOCC)C=1CCCCN1CCCCC1 IJXVXBFIGJLHPE-UHFFFAOYSA-N 0.000 description 1
- IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 description 1
- XLLWSAGWPIQRIC-UHFFFAOYSA-N 2-(1-benzylbenzimidazol-2-yl)-n,n-dimethylethanamine Chemical compound CN(C)CCC1=NC2=CC=CC=C2N1CC1=CC=CC=C1 XLLWSAGWPIQRIC-UHFFFAOYSA-N 0.000 description 1
- HLELOHQPJDTUAB-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)-n,n-dimethylethanamine Chemical compound C1=CC=C2NC(CCN(C)C)=NC2=C1 HLELOHQPJDTUAB-UHFFFAOYSA-N 0.000 description 1
- YBZNZLVTLMDPQU-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)-n,n-dimethylpropan-1-amine Chemical compound C1=CC=C2NC(C(CN(C)C)C)=NC2=C1 YBZNZLVTLMDPQU-UHFFFAOYSA-N 0.000 description 1
- HYGBHJLTBPTDMR-UHFFFAOYSA-N 2-(3-piperidin-1-ylpropyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CCCN1CCCCC1 HYGBHJLTBPTDMR-UHFFFAOYSA-N 0.000 description 1
- WOKMJKFPEQOVSI-UHFFFAOYSA-N 2-(3-pyrrolidin-1-ylpropyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CCCN1CCCC1 WOKMJKFPEQOVSI-UHFFFAOYSA-N 0.000 description 1
- RBNYBBQAGXRBCO-UHFFFAOYSA-N 2-(4-piperidin-1-ylbutyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CCCCN1CCCCC1 RBNYBBQAGXRBCO-UHFFFAOYSA-N 0.000 description 1
- VOHILFSOWRNVJJ-UHFFFAOYSA-N 2-(bromomethyl)oxolane Chemical compound BrCC1CCCO1 VOHILFSOWRNVJJ-UHFFFAOYSA-N 0.000 description 1
- IVHCSWUKMZEVQR-UHFFFAOYSA-N 2-[1-(2-ethoxyethyl)benzimidazol-2-yl]-n,n-dimethylpropan-1-amine Chemical compound C1=CC=C2N(CCOCC)C(C(C)CN(C)C)=NC2=C1 IVHCSWUKMZEVQR-UHFFFAOYSA-N 0.000 description 1
- GPADADODFARFSV-UHFFFAOYSA-N 3-(1-benzylbenzimidazol-2-yl)-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCC1=NC2=CC=CC=C2N1CC1=CC=CC=C1 GPADADODFARFSV-UHFFFAOYSA-N 0.000 description 1
- FWTAQZLVKZAMPD-UHFFFAOYSA-N 3-[1-(2-ethoxyethyl)benzimidazol-2-yl]-n,n-diethylpropan-1-amine Chemical compound C1=CC=C2N(CCOCC)C(CCCN(CC)CC)=NC2=C1 FWTAQZLVKZAMPD-UHFFFAOYSA-N 0.000 description 1
- KMHNYWITWKFNQW-UHFFFAOYSA-N 3-[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCC1=NC2=CC=CC=C2N1CC1=CC=C(F)C=C1 KMHNYWITWKFNQW-UHFFFAOYSA-N 0.000 description 1
- RROHDPSQLOVWIP-UHFFFAOYSA-N 4-(1h-benzimidazol-2-yl)-n,n-dimethylbutan-1-amine Chemical compound C1=CC=C2NC(CCCCN(C)C)=NC2=C1 RROHDPSQLOVWIP-UHFFFAOYSA-N 0.000 description 1
- RDTALXUBMCLWBB-UHFFFAOYSA-N 4-(dimethylamino)butanoic acid;hydron;chloride Chemical compound Cl.CN(C)CCCC(O)=O RDTALXUBMCLWBB-UHFFFAOYSA-N 0.000 description 1
- RIHLZJNHVIZCNO-UHFFFAOYSA-N 4-[1-(2-ethoxyethyl)benzimidazol-2-yl]-n,n-dimethylbutan-1-amine Chemical compound C1=CC=C2N(CCOCC)C(CCCCN(C)C)=NC2=C1 RIHLZJNHVIZCNO-UHFFFAOYSA-N 0.000 description 1
- UYEVTXJVVAHRFL-UHFFFAOYSA-N 5-(dimethylamino)-1-[1-(2-ethoxyethyl)benzimidazol-2-yl]pentan-1-one Chemical compound C1=CC=C2N(CCOCC)C(C(=O)CCCCN(C)C)=NC2=C1 UYEVTXJVVAHRFL-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- ZDIGNSYAACHWNL-UHFFFAOYSA-N brompheniramine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Br)C=C1 ZDIGNSYAACHWNL-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960004931 histamine dihydrochloride Drugs 0.000 description 1
- PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- UZQMSNUXJVDCHF-UHFFFAOYSA-N n,n-dimethyl-3-[1-(oxolan-2-ylmethyl)benzimidazol-2-yl]propan-1-amine Chemical compound CN(C)CCCC1=NC2=CC=CC=C2N1CC1CCCO1 UZQMSNUXJVDCHF-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960000351 terfenadine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S165/00—Heat exchange
- Y10S165/009—Heat exchange having a solid heat storage mass for absorbing heat from one fluid and releasing it to another, i.e. regenerator
- Y10S165/013—Movable heat storage mass with enclosure
- Y10S165/016—Rotary storage mass
- Y10S165/02—Seal and seal-engaging surface are relatively movable
- Y10S165/024—Circumferential seal
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
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Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ æ§é åŒ ãåã ïŒåŒäžã ã¯ããåŒããŸã㯠ãåŒãã§ããã ïœã¯ãïŒãŸãã¯ïŒã§ããã ïœã¯ãïŒãŸãã¯ïŒãïŒã®æŽæ°ã§ããïŒäœããïœ
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蚱容ãããåžéå€ãšæ··åããŠå«æããæãã¹ã¿ã
ã³å€ã
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8821271A IT1226100B (it) | 1988-07-07 | 1988-07-07 | Derivati benzimidazolici farmacologicamente attivi. |
| IT21271-A/88 | 1988-07-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0267272A JPH0267272A (ja) | 1990-03-07 |
| JPH0567624B2 true JPH0567624B2 (ja) | 1993-09-27 |
Family
ID=11179331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1173174A Granted JPH0267272A (ja) | 1988-07-07 | 1989-07-06 | è¬ç掻æ§ã®ãããã³ãŸã€ãããŸãŒã«èªå°äœ |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4971980A (ja) |
| EP (1) | EP0350467B1 (ja) |
| JP (1) | JPH0267272A (ja) |
| AT (1) | ATE99295T1 (ja) |
| DE (1) | DE68911773T2 (ja) |
| ES (1) | ES2062098T3 (ja) |
| IT (1) | IT1226100B (ja) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2665161B1 (fr) * | 1990-07-26 | 1992-11-27 | Esteve Labor Dr | Nouveaux derives de benzimidazole, leur preparation et leur application en tant que medicaments. |
| CA2097317C (en) * | 1990-12-14 | 2002-02-12 | Albert A. Carr | Antiallergic piperdinyl benzimidazoles |
| TW263504B (ja) * | 1991-10-03 | 1995-11-21 | Pfizer | |
| IT1264456B1 (it) * | 1993-05-14 | 1996-09-23 | Dompe Farmaceutici Spa | Derivati del 2-(benzimidazol-2-il)-1,3-diaminopropano farmacologicamente attivi. |
| GB9413724D0 (en) * | 1994-07-07 | 1994-08-24 | Wellcome Found | Therapeutic nucleosides |
| GB9600143D0 (en) | 1996-01-05 | 1996-03-06 | Wellcome Found | Therapeutic compounds |
| KR100494448B1 (ko) * | 1996-06-04 | 2005-12-02 | íëžëŠ¬ê¹ ìì€íëëŒ ë° íë¡ëëì€ ëë¯žêŒ¬ì€ ìŽ í륎ë§ìžì°ë êŒ¬ì€ ìììëŒ ìë žë | ííì€í믌íì±ìê°ì§ëì ê·í벀조ìŽë¯žë€ì¡žì ë첎 |
| DE69819695D1 (en) | 1997-02-13 | 2003-12-18 | Glaxo Group Ltd | Benzimidazolderivate |
| DK0994890T3 (da) | 1997-06-10 | 2003-12-01 | Univ Michigan | Benzimidazolderivater |
| WO1999006424A1 (en) | 1997-07-30 | 1999-02-11 | The Regents Of The University Of Michigan | Lyxofuranosyl benzimidazoles as antiviral agents |
| DE60007748T2 (de) * | 1999-06-28 | 2004-11-25 | Fuji Photo Film Co., Ltd., Minami-Ashigara | Benzimidazolderivate und sie enthaltende medikamente |
| SG122814A1 (en) * | 1999-06-28 | 2006-06-29 | Janssen Pharmaceutica Nv | Respiratory syncytial virus replication inhibitors |
| AU776803B2 (en) | 1999-06-30 | 2004-09-23 | Fuji Photo Film Co., Ltd. | Benzimidazole compounds and medicaments comprising the same |
| WO2001004110A1 (fr) | 1999-07-07 | 2001-01-18 | Fuji Photo Film Co., Ltd. | Composes de benzimidazole |
| US6349662B1 (en) * | 2000-12-29 | 2002-02-26 | Taco Metals, Inc. | Rub rail |
| WO2007106192A2 (en) * | 2005-12-19 | 2007-09-20 | Genentech, Inc. | Inhibitors of iap |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1023792A (en) * | 1963-04-17 | 1966-03-23 | Smith & Nephew | Benzimidazole derivatives and processes for making them |
| US3362956A (en) * | 1965-08-19 | 1968-01-09 | Sterling Drug Inc | 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines |
| US4462992A (en) * | 1982-02-08 | 1984-07-31 | Research Corporation | Nitroimidazole radiosensitizers for hypoxic tumor cells and compositions thereof |
| JPS59199679A (ja) * | 1983-04-27 | 1984-11-12 | Kanebo Ltd | æ°èŠãªãã³ãºã€ãããŸâã«èªå°äœããã®è£œé æ³ããã³ãã®å»è¬çµæç© |
| US4728741A (en) * | 1985-01-08 | 1988-03-01 | Smithkline Beckman Corporation | 1-substituted-2-mercapto benzimidazole compounds and intermediates |
-
1988
- 1988-07-07 IT IT8821271A patent/IT1226100B/it active
-
1989
- 1989-07-06 JP JP1173174A patent/JPH0267272A/ja active Granted
- 1989-07-06 AT AT89830312T patent/ATE99295T1/de active
- 1989-07-06 EP EP89830312A patent/EP0350467B1/en not_active Expired - Lifetime
- 1989-07-06 US US07/376,075 patent/US4971980A/en not_active Expired - Fee Related
- 1989-07-06 ES ES89830312T patent/ES2062098T3/es not_active Expired - Lifetime
- 1989-07-06 DE DE68911773T patent/DE68911773T2/de not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0267272A (ja) | 1990-03-07 |
| ATE99295T1 (de) | 1994-01-15 |
| IT8821271A0 (it) | 1988-07-07 |
| DE68911773T2 (de) | 1994-07-07 |
| DE68911773D1 (de) | 1994-02-10 |
| US4971980A (en) | 1990-11-20 |
| EP0350467A1 (en) | 1990-01-10 |
| IT1226100B (it) | 1990-12-10 |
| EP0350467B1 (en) | 1993-12-29 |
| ES2062098T3 (es) | 1994-12-16 |
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