BG60678B1 - Нови антихистаминови средства,производни на бензимидазолите - Google Patents
Нови антихистаминови средства,производни на бензимидазолите Download PDFInfo
- Publication number
- BG60678B1 BG60678B1 BG96180A BG9618092A BG60678B1 BG 60678 B1 BG60678 B1 BG 60678B1 BG 96180 A BG96180 A BG 96180A BG 9618092 A BG9618092 A BG 9618092A BG 60678 B1 BG60678 B1 BG 60678B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- radical
- general formula
- acceptable salts
- derivatives
- halogen atom
- Prior art date
Links
- 239000000739 antihistaminic agent Substances 0.000 title claims abstract description 9
- 150000001556 benzimidazoles Chemical class 0.000 title claims description 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 title abstract description 7
- 230000001387 anti-histamine Effects 0.000 title abstract description 7
- 239000000203 mixture Substances 0.000 title description 14
- -1 alkyl radical Chemical class 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 150000003254 radicals Chemical class 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims abstract description 3
- 229910052799 carbon Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000006574 non-aromatic ring group Chemical group 0.000 claims abstract description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
- 150000003457 sulfones Chemical class 0.000 claims abstract description 3
- 229940125715 antihistaminic agent Drugs 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 12
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 8
- 125000005905 mesyloxy group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000003814 drug Substances 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 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000003746 feather Anatomy 0.000 claims 1
- 229960001340 histamine Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 14
- 230000001624 sedative effect Effects 0.000 abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000004617 sleep duration Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 229960001412 pentobarbital Drugs 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 206010039897 Sedation Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229960000520 diphenhydramine Drugs 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229940052303 ethers for general anesthesia Drugs 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000036280 sedation Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- UPONBODVFUWSMG-UHFFFAOYSA-N 1-(4-chlorobutyl)pyrrole Chemical compound ClCCCCN1C=CC=C1 UPONBODVFUWSMG-UHFFFAOYSA-N 0.000 description 1
- GPTVQTPMFOLLOA-UHFFFAOYSA-N 1-chloro-2-ethoxyethane Chemical compound CCOCCCl GPTVQTPMFOLLOA-UHFFFAOYSA-N 0.000 description 1
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 1
- 241001279686 Allium moly Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000405217 Viola <butterfly> Species 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000000735 allogeneic effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Anesthesiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9104171A FR2674856B1 (fr) | 1991-04-05 | 1991-04-05 | Nouveaux antihistaminiques non sedatifs, derives de benzimidazole, leur procede de preparation et leur utilisation en tant que medicaments. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG96180A BG96180A (bg) | 1993-12-24 |
| BG60678B1 true BG60678B1 (bg) | 1995-12-29 |
Family
ID=9411523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG96180A BG60678B1 (bg) | 1991-04-05 | 1992-04-03 | Нови антихистаминови средства,производни на бензимидазолите |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5214040A (sh) |
| EP (1) | EP0507696B1 (sh) |
| JP (1) | JP3060054B2 (sh) |
| KR (1) | KR970011298B1 (sh) |
| CN (1) | CN1028367C (sh) |
| AT (1) | ATE126228T1 (sh) |
| AU (1) | AU647904B2 (sh) |
| BG (1) | BG60678B1 (sh) |
| BR (1) | BR1100983A (sh) |
| CA (1) | CA2065061A1 (sh) |
| CZ (1) | CZ279506B6 (sh) |
| DE (1) | DE69203911T2 (sh) |
| DK (1) | DK0507696T3 (sh) |
| ES (1) | ES2046110B1 (sh) |
| FI (1) | FI99112C (sh) |
| FR (1) | FR2674856B1 (sh) |
| GR (1) | GR3017643T3 (sh) |
| HU (1) | HU214316B (sh) |
| IL (1) | IL101483A (sh) |
| IS (1) | IS1639B (sh) |
| MX (1) | MX9201556A (sh) |
| NO (1) | NO179552C (sh) |
| NZ (1) | NZ242208A (sh) |
| PL (1) | PL167720B1 (sh) |
| RO (1) | RO109198B1 (sh) |
| RU (1) | RU2099336C1 (sh) |
| TW (1) | TW208003B (sh) |
| YU (1) | YU48826B (sh) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1264456B1 (it) * | 1993-05-14 | 1996-09-23 | Dompe Farmaceutici Spa | Derivati del 2-(benzimidazol-2-il)-1,3-diaminopropano farmacologicamente attivi. |
| FR2727865B1 (fr) * | 1994-12-08 | 1997-07-18 | Esteve Labor Dr | Utilisation des derives de 2-(4-(azolybutyl)-piperazinyl- (methyl))-benzimidazole et analogues ainsi que de leurs sels, pour la preparation de medicaments destines au traitement ou a la prophylaxie de l'asthme |
| US5773616A (en) * | 1995-02-15 | 1998-06-30 | Neurogen Corporation | Certain bridged 4-phenyl-2-aminomethylimidazoles; new dopamine receptor subtype specific ligands |
| WO1996025411A1 (en) * | 1995-02-15 | 1996-08-22 | Neurogen Corporation | Certain bridged 4-phenyl-2-aminomethylimidazoles; new dopamine receptor subtype specific ligands |
| FR2731618B1 (fr) * | 1995-03-14 | 1997-08-01 | Esteve Labor Dr | Composition ophtalmique topique comprenant un derive de 2-(4-(azolylbutyl)-piperazinyl-methyl)-benzimidazole, notamment pour le traitement de la conjonctivite allergique |
| US6211199B1 (en) | 1995-11-17 | 2001-04-03 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases |
| US6423704B2 (en) | 1995-12-20 | 2002-07-23 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic diseases |
| US6194406B1 (en) | 1995-12-20 | 2001-02-27 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic disease |
| US5932571A (en) * | 1996-02-21 | 1999-08-03 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-benzimidazol-2-yl) {1,4}diazepan-1-yl)-2-(aryl) butyl) benzamides useful for the treatment of allergic diseases |
| US5998439A (en) | 1996-02-21 | 1999-12-07 | Hoescht Marion Roussel, Inc. | Substituted N-methyl-N-(4-(piperidin-1-yl)-2-(aryl)butyl)benzamides useful for the treatment of allergic diseases |
| US5922737A (en) * | 1996-02-21 | 1999-07-13 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-Benzimidazol-2-YL-amino) piperidin-1-YL)-2-(arlyl) butyl) benzamides useful for the treatment of allergic diseases |
| TWI225488B (en) * | 1999-12-21 | 2004-12-21 | Janssen Pharmaceutica Nv | Derivatives of homopiperidinyl substituted benzimidazole analogues |
| NZ520402A (en) * | 2000-01-19 | 2006-04-28 | Cadila Healthcare Ltd | Novel compounds having hypolipedemic, hypocholesteremic activites, process for their preparation and pharmaceutical compositions containing them |
| HUP0301550A2 (hu) * | 2000-10-31 | 2003-09-29 | Basf Aktiengesellschaft | Hiper-elágazó poliuretánok alkalmazása nyomdafestékek elżállítására |
| JP2005532991A (ja) * | 2002-01-10 | 2005-11-04 | ニューロジェン・コーポレーション | メラニン凝集ホルモン受容体リガンド：置換２−（４−ベンジル−ピペラジン−１−イルメチル）−及び２−（４−ベンジル−ジアゼパン−１−イルメチル）−１ｈ−ベンゾイミダゾールアナログ |
| CN101089000B (zh) | 2006-06-16 | 2011-01-05 | 北京大学 | 螺环哌嗪季铵盐类化合物及其制备方法和应用 |
| RU2533825C2 (ru) * | 2009-06-11 | 2014-11-20 | Сиена Байотек С.П.А. | ПРОИЗВОДНЫЕ БЕНЗИМИДАЗОЛА И ИМИДАЗО[4,5-с]ПИРИДИНА, В КАЧЕСТВЕ АНТАГОНИСТА ПУТИ HEDGEHOG |
| LT2938597T (lt) * | 2012-12-27 | 2017-01-25 | Alzprotect | N-(3-(4-(3-(diizobutilamino)propil)piperazin-1-il)propil)-1h-benzo[d]imidazol-2-amino sulfatinės druskos, jų paruošimas ir panaudojimas |
| KR102057075B1 (ko) * | 2018-11-30 | 2019-12-19 | 우승열 | 페트병에 장착되는 여과장치 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200641A (en) * | 1976-12-21 | 1980-04-29 | Janssen Pharmaceutica, N.V. | 1-[(Heterocyclyl)-alkyl]-4-diarylmethoxy piperidine derivatives |
| DE3336409A1 (de) * | 1983-10-06 | 1985-04-18 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | Chinazolinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US5010075A (en) * | 1987-04-24 | 1991-04-23 | Syntex Pharmaceuticals Ltd. | Substituted imidazolyl-alkyl-piperazine and -diazepine derivatives |
| CA1317939C (en) * | 1987-07-01 | 1993-05-18 | Janssen Pharmaceutica Naamloze Vennootschap | ¬(bicyclic heterocyclyl)methyl and -hetero| substituted hexahydro-1h-azepines and pyrrolidines |
| FR2665161B1 (fr) * | 1990-07-26 | 1992-11-27 | Esteve Labor Dr | Nouveaux derives de benzimidazole, leur preparation et leur application en tant que medicaments. |
-
1991
- 1991-04-05 FR FR9104171A patent/FR2674856B1/fr not_active Expired - Fee Related
-
1992
- 1992-03-31 YU YU33692A patent/YU48826B/sh unknown
- 1992-03-31 TW TW081102419A patent/TW208003B/zh active
- 1992-04-01 RU SU925011426A patent/RU2099336C1/ru active
- 1992-04-02 NZ NZ242208A patent/NZ242208A/en unknown
- 1992-04-02 RO RO92-200447A patent/RO109198B1/ro unknown
- 1992-04-02 AU AU13979/92A patent/AU647904B2/en not_active Ceased
- 1992-04-02 IS IS3832A patent/IS1639B/is unknown
- 1992-04-03 FI FI921473A patent/FI99112C/fi active
- 1992-04-03 ES ES09200813A patent/ES2046110B1/es not_active Expired - Lifetime
- 1992-04-03 IL IL10148392A patent/IL101483A/en not_active IP Right Cessation
- 1992-04-03 PL PL92294101A patent/PL167720B1/pl unknown
- 1992-04-03 EP EP92400940A patent/EP0507696B1/fr not_active Expired - Lifetime
- 1992-04-03 HU HU9201145A patent/HU214316B/hu not_active IP Right Cessation
- 1992-04-03 US US07/863,208 patent/US5214040A/en not_active Expired - Fee Related
- 1992-04-03 KR KR1019920005583A patent/KR970011298B1/ko not_active IP Right Cessation
- 1992-04-03 BG BG96180A patent/BG60678B1/bg unknown
- 1992-04-03 CZ CS921017A patent/CZ279506B6/cs not_active IP Right Cessation
- 1992-04-03 DE DE69203911T patent/DE69203911T2/de not_active Expired - Fee Related
- 1992-04-03 NO NO921315A patent/NO179552C/no not_active IP Right Cessation
- 1992-04-03 DK DK92400940.0T patent/DK0507696T3/da active
- 1992-04-03 AT AT92400940T patent/ATE126228T1/de not_active IP Right Cessation
- 1992-04-03 CA CA002065061A patent/CA2065061A1/fr not_active Abandoned
- 1992-04-03 MX MX9201556A patent/MX9201556A/es unknown
- 1992-04-04 CN CN92102353A patent/CN1028367C/zh not_active Expired - Fee Related
- 1992-04-06 JP JP4084230A patent/JP3060054B2/ja not_active Expired - Lifetime
-
1995
- 1995-10-04 GR GR950402756T patent/GR3017643T3/el unknown
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1997
- 1997-05-14 BR BR1100983-7A patent/BR1100983A/pt active IP Right Grant
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