CH625228A5 - - Google Patents
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- Publication number
- CH625228A5 CH625228A5 CH172677A CH172677A CH625228A5 CH 625228 A5 CH625228 A5 CH 625228A5 CH 172677 A CH172677 A CH 172677A CH 172677 A CH172677 A CH 172677A CH 625228 A5 CH625228 A5 CH 625228A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- amino
- acid
- propionic acid
- benzimidazol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 description 47
- 238000000034 method Methods 0.000 description 26
- 239000000203 mixture Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- -1 benzimidazol-2-one-5-yl Chemical group 0.000 description 11
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 7
- 229910000564 Raney nickel Inorganic materials 0.000 description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
- RVMRRTJTCBIPNH-UHFFFAOYSA-N diethyl 2-acetamido-2-[(4-acetamido-3-nitrophenyl)methyl]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)(NC(C)=O)CC1=CC=C(NC(C)=O)C([N+]([O-])=O)=C1 RVMRRTJTCBIPNH-UHFFFAOYSA-N 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 7
- 235000019260 propionic acid Nutrition 0.000 description 7
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 7
- 239000001632 sodium acetate Substances 0.000 description 7
- 235000017281 sodium acetate Nutrition 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 150000001734 carboxylic acid salts Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- RTEARMSQRKDFRT-UHFFFAOYSA-N methyl 2-acetamido-3-(4-acetamido-3-nitrophenyl)-2-methylpropanoate Chemical compound COC(=O)C(C)(NC(C)=O)CC1=CC=C(NC(C)=O)C([N+]([O-])=O)=C1 RTEARMSQRKDFRT-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- BSRLHDVGRQWLLJ-UHFFFAOYSA-N 2-amino-2-methyl-3-(1-methyl-2-oxo-3h-benzimidazol-5-yl)propanoic acid;hydrochloride Chemical compound Cl.C1=C(CC(C)(N)C(O)=O)C=C2NC(=O)N(C)C2=C1 BSRLHDVGRQWLLJ-UHFFFAOYSA-N 0.000 description 2
- XFGBAXQMKPJXDX-UHFFFAOYSA-N 2-amino-3-(1,3-dimethyl-2-oxobenzimidazol-5-yl)propanoic acid;hydrochloride Chemical compound Cl.C1=C(CC(N)C(O)=O)C=C2N(C)C(=O)N(C)C2=C1 XFGBAXQMKPJXDX-UHFFFAOYSA-N 0.000 description 2
- JVUYNTIXRVYTDL-UHFFFAOYSA-N 2-amino-3-(2-ethoxy-1-methylbenzimidazol-5-yl)propanoic acid Chemical compound OC(=O)C(N)CC1=CC=C2N(C)C(OCC)=NC2=C1 JVUYNTIXRVYTDL-UHFFFAOYSA-N 0.000 description 2
- IKVJOZIXFQSOQK-UHFFFAOYSA-N 2-amino-3-(2-ethoxy-3h-benzimidazol-5-yl)-2-methylpropanoic acid Chemical compound C1=C(CC(C)(N)C(O)=O)C=C2NC(OCC)=NC2=C1 IKVJOZIXFQSOQK-UHFFFAOYSA-N 0.000 description 2
- RDLKHEMIILJJPV-UHFFFAOYSA-N 2-amino-3-(2-ethoxy-3h-benzimidazol-5-yl)propanoic acid Chemical compound C1=C(CC(N)C(O)=O)C=C2NC(OCC)=NC2=C1 RDLKHEMIILJJPV-UHFFFAOYSA-N 0.000 description 2
- DFSLMANAFKLXAB-UHFFFAOYSA-N 2-amino-3-(3-methyl-2-oxo-1h-benzimidazol-5-yl)propanoic acid;hydrochloride Chemical compound Cl.OC(=O)C(N)CC1=CC=C2NC(=O)N(C)C2=C1 DFSLMANAFKLXAB-UHFFFAOYSA-N 0.000 description 2
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000167854 Bourreria succulenta Species 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001294 alanine derivatives Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000019693 cherries Nutrition 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000000391 smoking effect Effects 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
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- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JJQRNNHVPNITKF-NSHDSACASA-N (2s)-2-amino-2-methyl-3-(2-oxobenzimidazol-5-yl)propanoic acid Chemical compound C1=C(C[C@@](N)(C)C(O)=O)C=CC2=NC(=O)N=C21 JJQRNNHVPNITKF-NSHDSACASA-N 0.000 description 1
- PAHKEQUOPFGGKA-UHFFFAOYSA-N 2-acetamido-2-[[4-acetamido-3-(methylamino)phenyl]methyl]-3-methoxy-3-oxopropanoic acid Chemical compound CNC1=CC(CC(NC(C)=O)(C(O)=O)C(=O)OC)=CC=C1NC(C)=O PAHKEQUOPFGGKA-UHFFFAOYSA-N 0.000 description 1
- FZYSMOAZONJXDK-UHFFFAOYSA-N 2-acetamido-3-[4-amino-3-(methylamino)phenyl]-2-methylpropanoic acid Chemical compound CNC1=CC(CC(C)(NC(C)=O)C(O)=O)=CC=C1N FZYSMOAZONJXDK-UHFFFAOYSA-N 0.000 description 1
- NCHUDVKCCDIDLF-UHFFFAOYSA-N 2-amino-2-methyl-3-(3-methyl-2-oxo-1h-benzimidazol-5-yl)propanoic acid;hydrochloride Chemical compound Cl.OC(=O)C(C)(N)CC1=CC=C2NC(=O)N(C)C2=C1 NCHUDVKCCDIDLF-UHFFFAOYSA-N 0.000 description 1
- JVIDHGSMIZDRHI-UHFFFAOYSA-N 2-amino-3-(1,3-dimethyl-2-oxobenzimidazol-5-yl)-2-methylpropanoic acid;hydrochloride Chemical compound Cl.C1=C(CC(C)(N)C(O)=O)C=C2N(C)C(=O)N(C)C2=C1 JVIDHGSMIZDRHI-UHFFFAOYSA-N 0.000 description 1
- ZGZKLHKEVIEAKR-UHFFFAOYSA-N 2-amino-3-(1-methyl-2-oxo-3h-benzimidazol-5-yl)propanoic acid Chemical compound C1=C(CC(N)C(O)=O)C=C2NC(=O)N(C)C2=C1 ZGZKLHKEVIEAKR-UHFFFAOYSA-N 0.000 description 1
- YDZWJDSDINTBHY-UHFFFAOYSA-N 2-amino-3-(1-methyl-2-oxo-3h-benzimidazol-5-yl)propanoic acid;hydrochloride Chemical compound Cl.C1=C(CC(N)C(O)=O)C=C2NC(=O)N(C)C2=C1 YDZWJDSDINTBHY-UHFFFAOYSA-N 0.000 description 1
- SARUXYMTPYNISJ-UHFFFAOYSA-N 2-amino-3-(2-ethoxy-3-methylbenzimidazol-5-yl)-2-methylpropanoic acid Chemical compound C1=C(CC(C)(N)C(O)=O)C=C2N(C)C(OCC)=NC2=C1 SARUXYMTPYNISJ-UHFFFAOYSA-N 0.000 description 1
- DOHDVEGRENYZAE-UHFFFAOYSA-N 2-amino-3-(2-ethoxy-3-methylbenzimidazol-5-yl)propanoic acid Chemical compound C1=C(CC(N)C(O)=O)C=C2N(C)C(OCC)=NC2=C1 DOHDVEGRENYZAE-UHFFFAOYSA-N 0.000 description 1
- JOOCUSFATTXVIS-UHFFFAOYSA-N 2-amino-3-(3-methyl-2-oxo-1h-benzimidazol-5-yl)propanoic acid Chemical compound OC(=O)C(N)CC1=CC=C2NC(=O)N(C)C2=C1 JOOCUSFATTXVIS-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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- 229920001800 Shellac Polymers 0.000 description 1
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- 229920001615 Tragacanth Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
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- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
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- HXUUZMLLNYCNFT-UHFFFAOYSA-N diethyl 2-[3-(4-acetamidophenyl)propanoylamino]propanedioate Chemical compound C(C)OC(C(C(=O)OCC)NC(CCC1=CC=C(C=C1)NC(C)=O)=O)=O HXUUZMLLNYCNFT-UHFFFAOYSA-N 0.000 description 1
- FWEYFIASWPIYDH-UHFFFAOYSA-N diethyl 2-[3-(4-aminophenyl)propanoylamino]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)NC(=O)CCC1=CC=C(N)C=C1 FWEYFIASWPIYDH-UHFFFAOYSA-N 0.000 description 1
- JOTXXXKSIIESDE-UHFFFAOYSA-N diethyl 2-[3-(4-nitrophenyl)propanoylamino]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)NC(=O)CCC1=CC=C([N+]([O-])=O)C=C1 JOTXXXKSIIESDE-UHFFFAOYSA-N 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000012773 waffles Nutrition 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
- C07D235/24—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/657,829 US4073929A (en) | 1976-02-13 | 1976-02-13 | 3-(2-Substitutedbenzimidazolyl) alanines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH625228A5 true CH625228A5 (enExample) | 1981-09-15 |
Family
ID=24638816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH172677A CH625228A5 (enExample) | 1976-02-13 | 1977-02-11 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4073929A (enExample) |
| JP (1) | JPS5297967A (enExample) |
| CH (1) | CH625228A5 (enExample) |
| DE (1) | DE2705892A1 (enExample) |
| DK (1) | DK31277A (enExample) |
| FR (1) | FR2340935A1 (enExample) |
| GB (1) | GB1521025A (enExample) |
| NL (1) | NL7700947A (enExample) |
| SE (1) | SE7701506L (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4070478A (en) * | 1977-02-17 | 1978-01-24 | Merck & Co., Inc. | Benzimidazole substituted alanines |
| DE2801980A1 (de) * | 1978-01-18 | 1979-07-19 | Boehringer Mannheim Gmbh | 4-hydroxy-2-benzimidazolin-thion- derivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
| US4537907A (en) * | 1980-10-06 | 1985-08-27 | University Of Illinois Foundation | Hypnotic composition and method of inducing sleep |
| AU2001267465B2 (en) * | 2000-05-30 | 2006-02-02 | Boehringer Ingelheim Animal Health USA Inc. | Methods for prevention of ulcers and improving physiological performance |
-
1976
- 1976-02-13 US US05/657,829 patent/US4073929A/en not_active Expired - Lifetime
-
1977
- 1977-01-25 DK DK31277A patent/DK31277A/da unknown
- 1977-01-28 NL NL7700947A patent/NL7700947A/xx not_active Application Discontinuation
- 1977-02-10 GB GB5519/77A patent/GB1521025A/en not_active Expired
- 1977-02-10 JP JP1308577A patent/JPS5297967A/ja active Pending
- 1977-02-10 SE SE7701506A patent/SE7701506L/xx not_active Application Discontinuation
- 1977-02-11 DE DE19772705892 patent/DE2705892A1/de not_active Withdrawn
- 1977-02-11 CH CH172677A patent/CH625228A5/de not_active IP Right Cessation
- 1977-02-11 FR FR7703913A patent/FR2340935A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5297967A (en) | 1977-08-17 |
| DK31277A (da) | 1977-08-14 |
| FR2340935B1 (enExample) | 1978-11-17 |
| SE7701506L (sv) | 1977-08-14 |
| FR2340935A1 (fr) | 1977-09-09 |
| DE2705892A1 (de) | 1977-08-18 |
| NL7700947A (nl) | 1977-08-16 |
| GB1521025A (en) | 1978-08-09 |
| US4073929A (en) | 1978-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |