DE2203373C3 - Neue 2- [(2- Alkylbenzofuran-3-yl)-methyl] -A2 -imidazoline - Google Patents
Neue 2- [(2- Alkylbenzofuran-3-yl)-methyl] -A2 -imidazolineInfo
- Publication number
- DE2203373C3 DE2203373C3 DE2203373A DE2203373A DE2203373C3 DE 2203373 C3 DE2203373 C3 DE 2203373C3 DE 2203373 A DE2203373 A DE 2203373A DE 2203373 A DE2203373 A DE 2203373A DE 2203373 C3 DE2203373 C3 DE 2203373C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- solution
- hydrochloride
- imidazoline
- compounds
- 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
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 description 36
- 239000000243 solution Substances 0.000 description 23
- CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- -1 2-ethylbenzofuran-3-yl Chemical group 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 229960005016 naphazoline Drugs 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000000975 dye Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000005526 vasoconstrictor agent Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- UFQDKRWQSFLPQY-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-3-ium;chloride Chemical compound Cl.C1CN=CN1 UFQDKRWQSFLPQY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009792 diffusion process Methods 0.000 description 6
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 230000001886 ciliary effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- RWCHGCSLPRNFRX-UHFFFAOYSA-N 2-(2-ethyl-1-benzofuran-3-yl)acetonitrile Chemical compound C1=CC=C2C(CC#N)=C(CC)OC2=C1 RWCHGCSLPRNFRX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 210000004081 cilia Anatomy 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 210000004400 mucous membrane Anatomy 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 210000003437 trachea Anatomy 0.000 description 3
- WAJGQJWHIKUPRN-UHFFFAOYSA-N 3-(chloromethyl)-2-ethyl-1-benzofuran Chemical compound C(C)C1=C(C2=C(O1)C=CC=C2)CCl WAJGQJWHIKUPRN-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 description 2
- 235000019800 disodium phosphate Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 210000002850 nasal mucosa Anatomy 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- BITVLJAJVLSVLZ-UHFFFAOYSA-N 2-(2-butyl-1-benzofuran-3-yl)acetonitrile Chemical compound C(CCC)C1=C(C2=C(O1)C=CC=C2)CC#N BITVLJAJVLSVLZ-UHFFFAOYSA-N 0.000 description 1
- AQFDXZOGFHBNRW-UHFFFAOYSA-N 2-butyl-3-(chloromethyl)-1-benzofuran Chemical compound C(CCC)C1=C(C2=C(O1)C=CC=C2)CCl AQFDXZOGFHBNRW-UHFFFAOYSA-N 0.000 description 1
- KJHYAEZMOHLVCH-UHFFFAOYSA-N 2-ethyl-1-benzofuran Chemical compound C1=CC=C2OC(CC)=CC2=C1 KJHYAEZMOHLVCH-UHFFFAOYSA-N 0.000 description 1
- PGHBDULKXIGKRN-UHFFFAOYSA-N 3-(chloromethyl)-2-propan-2-yl-1-benzofuran Chemical compound C(C)(C)C=1OC2=C(C1CCl)C=CC=C2 PGHBDULKXIGKRN-UHFFFAOYSA-N 0.000 description 1
- MYKCEOXLNCJESE-UHFFFAOYSA-N 3-(chloromethyl)-2-propyl-1-benzofuran Chemical compound C(CC)C1=C(C2=C(O1)C=CC=C2)CCl MYKCEOXLNCJESE-UHFFFAOYSA-N 0.000 description 1
- SNDPDIKRADZYGK-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-1-ium;bromide Chemical compound Br.C1CN=CN1 SNDPDIKRADZYGK-UHFFFAOYSA-N 0.000 description 1
- IFCOMSZHIDTXOT-UHFFFAOYSA-N 4,5-dihydro-1h-imidazole;sulfuric acid Chemical compound C1CN=CN1.OS(O)(=O)=O IFCOMSZHIDTXOT-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 240000000662 Anethum graveolens Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- RKSHWZSTKNRVNS-UHFFFAOYSA-N C(C(=O)O)(=O)O.N1C=NCC1 Chemical compound C(C(=O)O)(=O)O.N1C=NCC1 RKSHWZSTKNRVNS-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000012891 Ringer solution Substances 0.000 description 1
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229960001950 benzethonium chloride Drugs 0.000 description 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002517 constrictor effect Effects 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- IIRVGTWONXBBAW-UHFFFAOYSA-M disodium;dioxido(oxo)phosphanium Chemical compound [Na+].[Na+].[O-][P+]([O-])=O IIRVGTWONXBBAW-UHFFFAOYSA-M 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D405/06—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 linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB332771 | 1971-01-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2203373A1 DE2203373A1 (de) | 1972-08-17 |
| DE2203373B2 DE2203373B2 (de) | 1977-08-11 |
| DE2203373C3 true DE2203373C3 (de) | 1978-04-13 |
Family
ID=9756227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2203373A Expired DE2203373C3 (de) | 1971-01-27 | 1972-01-25 | Neue 2- [(2- Alkylbenzofuran-3-yl)-methyl] -A2 -imidazoline |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3818035A (forum.php) |
| JP (1) | JPS4938273B1 (forum.php) |
| AT (1) | AT311336B (forum.php) |
| BE (1) | BE777689A (forum.php) |
| CA (1) | CA962273A (forum.php) |
| CH (1) | CH535254A (forum.php) |
| DE (1) | DE2203373C3 (forum.php) |
| DK (1) | DK138496B (forum.php) |
| FI (1) | FI55841C (forum.php) |
| GB (1) | GB1333471A (forum.php) |
| HU (1) | HU162823B (forum.php) |
| NL (1) | NL150454B (forum.php) |
| NO (1) | NO134115C (forum.php) |
| SE (1) | SE378426B (forum.php) |
| SU (1) | SU474145A3 (forum.php) |
| YU (1) | YU34694B (forum.php) |
| ZA (1) | ZA72286B (forum.php) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3927023A (en) * | 1974-05-24 | 1975-12-16 | Warner Lambert Co | Imidazolyl benzofurans |
| DE3049542A1 (de) * | 1980-12-31 | 1982-07-29 | Basf Ag, 6700 Ludwigshafen | Azolylalkyl-2,3-dihydrobenzofurane, diese enthaltende fungizide und verfahren zu ihrer herstellung |
| ZA825413B (en) * | 1981-08-26 | 1983-06-29 | Pfizer | Thromboxane synthetase inhibitors, processes for their production, and pharmaceutical compositions comprising them |
| US4806663A (en) * | 1987-04-06 | 1989-02-21 | The University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
| US4851554A (en) * | 1987-04-06 | 1989-07-25 | University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
| US4831156A (en) * | 1987-09-30 | 1989-05-16 | The University Of Tennessee Research Corp. | 3-substituted 2-alkyl indole derivatives |
| JP2001526286A (ja) * | 1997-12-19 | 2001-12-18 | イーライ・リリー・アンド・カンパニー | 低血糖性イミダゾリン化合物 |
| US7777035B2 (en) * | 2005-06-22 | 2010-08-17 | Chemocentryx, Inc. | Azaindazole compounds and methods of use |
| AU2007209381A1 (en) * | 2006-01-27 | 2007-08-02 | F. Hoffmann-La Roche Ag | Use of substituted 2-imidazole of imidazoline derivatives |
| JP5335681B2 (ja) * | 2006-10-19 | 2013-11-06 | エフ．ホフマン−ラ ロシュ アーゲー | アミノメチル−４−イミダゾール |
| DE602007005671D1 (de) * | 2006-10-19 | 2010-05-12 | Hoffmann La Roche | Aminomethyl-2-imidazole mit affinität zu mit dem trace-amin assoziierten rezeptoren |
| WO2008052907A1 (en) * | 2006-11-02 | 2008-05-08 | F. Hoffmann-La Roche Ag | Substituted 2-imidazoles as modulators of the trace amine associated receptors |
| WO2008058867A2 (en) * | 2006-11-16 | 2008-05-22 | F. Hoffmann-La Roche Ag | Substituted 4-imidazoles |
| EP2101762B1 (en) * | 2006-12-13 | 2011-05-18 | F. Hoffmann-La Roche AG | Novel 2 -imidazoles as ligands for trace amine associated receptors (taar) |
| US20080146523A1 (en) * | 2006-12-18 | 2008-06-19 | Guido Galley | Imidazole derivatives |
| CA2675221C (en) | 2007-02-02 | 2016-02-23 | F. Hoffmann-La Roche Ag | Novel 2-aminooxazolines as taar1 ligands |
| CA2676944C (en) * | 2007-02-15 | 2016-01-19 | F. Hoffmann-La Roche Ag | 2-aminooxazolines as taar1 ligands |
| BRPI0812840A2 (pt) | 2007-07-02 | 2014-12-09 | Hoffmann La Roche | 2-imidazolinas |
| CA2691704A1 (en) * | 2007-07-03 | 2009-01-08 | F. Hoffmann-La Roche Ag | 4-imidazolines and their use as antidepressants |
| CA2694362A1 (en) * | 2007-07-27 | 2009-02-05 | F. Hoffmann-La Roche Ag | 2-azetidinemethaneamines and 2-pyrrolidinemethaneamines as taar-ligands |
| AU2008281877A1 (en) * | 2007-08-02 | 2009-02-05 | F. Hoffmann-La Roche Ag | The use of benzamide derivatives for the treatment of CNS disorders |
| CN101784515A (zh) * | 2007-08-03 | 2010-07-21 | 弗·哈夫曼-拉罗切有限公司 | 作为taar1配体的吡啶甲酰胺和苯甲酰胺衍生物 |
| US8242153B2 (en) * | 2008-07-24 | 2012-08-14 | Hoffmann-La Roche Inc. | 4,5-dihydro-oxazol-2YL derivatives |
| ES2556633T3 (es) * | 2008-07-24 | 2016-01-19 | F. Hoffmann-La Roche Ag | Derivados de 4,5-dihidro-oxazol-2-ilo |
| US20100311798A1 (en) * | 2009-06-05 | 2010-12-09 | Decoret Guillaume | 2-aminooxazolines as taar1 ligands |
| US8354441B2 (en) * | 2009-11-11 | 2013-01-15 | Hoffmann-La Roche Inc. | Oxazoline derivatives |
| US9452980B2 (en) | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
| HUE050986T2 (hu) | 2016-03-17 | 2021-01-28 | Hoffmann La Roche | 5-etil-4-metil-pirazol-3-karboxamid származék, amely TAAR-agonista aktivitású |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1121054B (de) * | 1960-11-23 | 1962-01-04 | Merck Ag E | Verfahren zur Herstellung eines neuen Imidazolinderivates und dessen Saeureadditionssalzen |
-
1971
- 1971-01-27 GB GB332771A patent/GB1333471A/en not_active Expired
-
1972
- 1972-01-05 BE BE777689A patent/BE777689A/xx not_active IP Right Cessation
- 1972-01-06 CH CH17272A patent/CH535254A/fr not_active IP Right Cessation
- 1972-01-10 US US00216795A patent/US3818035A/en not_active Expired - Lifetime
- 1972-01-17 ZA ZA720286A patent/ZA72286B/xx unknown
- 1972-01-25 DE DE2203373A patent/DE2203373C3/de not_active Expired
- 1972-01-26 NO NO192/72A patent/NO134115C/no unknown
- 1972-01-26 DK DK34572AA patent/DK138496B/da unknown
- 1972-01-26 SE SE7200867A patent/SE378426B/xx unknown
- 1972-01-26 YU YU181/72A patent/YU34694B/xx unknown
- 1972-01-26 HU HULA791A patent/HU162823B/hu not_active IP Right Cessation
- 1972-01-27 SU SU1742351A patent/SU474145A3/ru active
- 1972-01-27 JP JP47010207A patent/JPS4938273B1/ja active Pending
- 1972-01-27 NL NL727201121A patent/NL150454B/xx not_active IP Right Cessation
- 1972-01-27 CA CA133,337A patent/CA962273A/en not_active Expired
- 1972-01-27 AT AT64772A patent/AT311336B/de not_active IP Right Cessation
- 1972-01-27 FI FI219/72A patent/FI55841C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| YU34694B (en) | 1979-12-31 |
| CH535254A (fr) | 1973-03-31 |
| FI55841B (fi) | 1979-06-29 |
| NL150454B (nl) | 1976-08-16 |
| BE777689A (fr) | 1972-07-05 |
| NO134115C (forum.php) | 1976-08-18 |
| GB1333471A (en) | 1973-10-10 |
| JPS4938273B1 (forum.php) | 1974-10-16 |
| SE378426B (forum.php) | 1975-09-01 |
| NL7201121A (forum.php) | 1972-07-31 |
| SU474145A3 (ru) | 1975-06-14 |
| HU162823B (forum.php) | 1973-04-28 |
| DE2203373B2 (de) | 1977-08-11 |
| ZA72286B (en) | 1972-09-27 |
| NO134115B (forum.php) | 1976-05-10 |
| CA962273A (en) | 1975-02-04 |
| US3818035A (en) | 1974-06-18 |
| FI55841C (fi) | 1979-10-10 |
| YU18172A (en) | 1979-07-10 |
| DK138496B (da) | 1978-09-18 |
| DK138496C (forum.php) | 1979-02-26 |
| AT311336B (de) | 1973-11-12 |
| AU3817772A (en) | 1973-07-26 |
| DE2203373A1 (de) | 1972-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |