NO134115B - - Google Patents
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- Publication number
- NO134115B NO134115B NO192/72A NO19272A NO134115B NO 134115 B NO134115 B NO 134115B NO 192/72 A NO192/72 A NO 192/72A NO 19272 A NO19272 A NO 19272A NO 134115 B NO134115 B NO 134115B
- Authority
- NO
- Norway
- Prior art keywords
- furan
- formula
- hydrochloride
- ethyl
- acid addition
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- 150000002462 imidazolines Chemical class 0.000 claims description 3
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- -1 ethanol Chemical compound 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000005526 vasoconstrictor agent Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 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
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- UFQDKRWQSFLPQY-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-3-ium;chloride Chemical compound Cl.C1CN=CN1 UFQDKRWQSFLPQY-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- 150000002240 furans Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- DJDFFEBSKJCGHC-UHFFFAOYSA-N Naphazoline Chemical compound Cl.C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 DJDFFEBSKJCGHC-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 210000004877 mucosa Anatomy 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 210000004081 cilia Anatomy 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229960004760 naphazoline hydrochloride Drugs 0.000 description 3
- 210000002850 nasal mucosa Anatomy 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000001886 ciliary effect Effects 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 210000000981 epithelium Anatomy 0.000 description 2
- OIJWIKJZWZRMBZ-UHFFFAOYSA-N ethyl 2-(2-ethyl-1-benzofuran-3-yl)-2-iminoacetate hydrochloride Chemical compound Cl.C(C)C=1OC2=C(C1C(C(=O)OCC)=N)C=CC=C2 OIJWIKJZWZRMBZ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000004899 motility Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000003437 trachea Anatomy 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 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
- YDDYHDKRIBOHOT-UHFFFAOYSA-N 2-[(2-ethyl-1-benzofuran-3-yl)methyl]-4,5-dihydro-1h-imidazol-3-ium;chloride Chemical compound [Cl-].CCC=1OC2=CC=CC=C2C=1CC1=[NH+]CCN1 YDDYHDKRIBOHOT-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
- 206010002091 Anaesthesia Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 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
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000008346 aqueous phase Substances 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
- 229960001950 benzethonium chloride Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 210000004209 hair Anatomy 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
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000001665 trituration Methods 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 (2)
| Publication Number | Publication Date |
|---|---|
| NO134115B true NO134115B (en:Method) | 1976-05-10 |
| NO134115C NO134115C (en:Method) | 1976-08-18 |
Family
ID=9756227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO192/72A NO134115C (en:Method) | 1971-01-27 | 1972-01-26 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3818035A (en:Method) |
| JP (1) | JPS4938273B1 (en:Method) |
| AT (1) | AT311336B (en:Method) |
| BE (1) | BE777689A (en:Method) |
| CA (1) | CA962273A (en:Method) |
| CH (1) | CH535254A (en:Method) |
| DE (1) | DE2203373C3 (en:Method) |
| DK (1) | DK138496B (en:Method) |
| FI (1) | FI55841C (en:Method) |
| GB (1) | GB1333471A (en:Method) |
| HU (1) | HU162823B (en:Method) |
| NL (1) | NL150454B (en:Method) |
| NO (1) | NO134115C (en:Method) |
| SE (1) | SE378426B (en:Method) |
| SU (1) | SU474145A3 (en:Method) |
| YU (1) | YU34694B (en:Method) |
| ZA (1) | ZA72286B (en:Method) |
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 |
| CA2315226A1 (en) * | 1997-12-19 | 1999-07-01 | Eli Lilly And Company | Hypoglycemic imidazoline compounds |
| 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 |
| CA2666762C (en) * | 2006-10-19 | 2014-12-30 | F. Hoffmann-La Roche Ag | Aminomethyl-4-imidazoles |
| ES2340223T3 (es) * | 2006-10-19 | 2010-05-31 | F. Hoffmann-La Roche Ag | Aminometil-2-imidazoles con afinidad con los trace receptores asociados amina. |
| CN101535292A (zh) * | 2006-11-02 | 2009-09-16 | 弗·哈夫曼-拉罗切有限公司 | 作为痕量胺相关受体的调节剂的取代的2-咪唑类化合物 |
| MX2009005047A (es) * | 2006-11-16 | 2009-05-25 | Hoffmann La Roche | 4-imidazoles sustituidos. |
| BRPI0720047A2 (pt) * | 2006-12-13 | 2013-12-24 | Hoffmann La Roche | 2-imidazóis como ligantes para receptores associados a aminas de traço (taar) |
| US20080146523A1 (en) * | 2006-12-18 | 2008-06-19 | Guido Galley | Imidazole derivatives |
| WO2008092785A1 (en) * | 2007-02-02 | 2008-08-07 | F. Hoffmann-La Roche Ag | Novel 2-aminooxazolines as taar1 ligands for cns disorders |
| EP2121641B1 (en) * | 2007-02-15 | 2014-09-24 | F. Hoffmann-La Roche AG | 2-aminooxazolines as taar1 ligands |
| EP2173720A2 (en) | 2007-07-02 | 2010-04-14 | F. Hoffmann-Roche AG | 2-imidazolines having a good affinity to the trace amine associated receptors (taars) |
| AU2008270444A1 (en) * | 2007-07-03 | 2009-01-08 | F. Hoffmann-La Roche Ag | 4-imidazolines and their use as antidepressants |
| EP2183216A1 (en) * | 2007-07-27 | 2010-05-12 | F. Hoffmann-Roche AG | 2-azetidinemethaneamines and 2-pyrrolidinemethaneamines as taar-ligands |
| CA2695071A1 (en) * | 2007-08-02 | 2009-02-05 | F. Hoffmann-La Roche Ag | The use of benzamide derivatives for the treatment of cns disorders |
| AU2008285795A1 (en) * | 2007-08-03 | 2009-02-12 | F. Hoffmann-La Roche Ag | Pyridinecarboxamide and benzamide derivatives as TAAR1 ligands |
| US8242153B2 (en) * | 2008-07-24 | 2012-08-14 | Hoffmann-La Roche Inc. | 4,5-dihydro-oxazol-2YL derivatives |
| EP2321287B1 (en) * | 2008-07-24 | 2015-11-11 | F. Hoffmann-La Roche AG | 4,5-dihydro-oxazol-2-yl derivatives |
| 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 |
| EP3430010B1 (en) | 2016-03-17 | 2020-07-15 | H. Hoffnabb-La Roche Ag | 5-ethyl-4-methyl-pyrazole-3-carboxamide derivative having activity as agonist of taar |
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 HU HULA791A patent/HU162823B/hu not_active IP Right Cessation
- 1972-01-26 DK DK34572AA patent/DK138496B/da unknown
- 1972-01-26 SE SE7200867A patent/SE378426B/xx unknown
- 1972-01-26 NO NO192/72A patent/NO134115C/no unknown
- 1972-01-26 YU YU181/72A patent/YU34694B/xx unknown
- 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 SU SU1742351A patent/SU474145A3/ru active
- 1972-01-27 NL NL727201121A patent/NL150454B/xx not_active IP Right Cessation
- 1972-01-27 FI FI219/72A patent/FI55841C/fi active
- 1972-01-27 JP JP47010207A patent/JPS4938273B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| YU34694B (en) | 1979-12-31 |
| AT311336B (de) | 1973-11-12 |
| US3818035A (en) | 1974-06-18 |
| DK138496B (da) | 1978-09-18 |
| NL150454B (nl) | 1976-08-16 |
| FI55841C (fi) | 1979-10-10 |
| YU18172A (en) | 1979-07-10 |
| DE2203373C3 (de) | 1978-04-13 |
| AU3817772A (en) | 1973-07-26 |
| DE2203373A1 (de) | 1972-08-17 |
| DK138496C (en:Method) | 1979-02-26 |
| NL7201121A (en:Method) | 1972-07-31 |
| CA962273A (en) | 1975-02-04 |
| GB1333471A (en) | 1973-10-10 |
| JPS4938273B1 (en:Method) | 1974-10-16 |
| SU474145A3 (ru) | 1975-06-14 |
| HU162823B (en:Method) | 1973-04-28 |
| BE777689A (fr) | 1972-07-05 |
| SE378426B (en:Method) | 1975-09-01 |
| DE2203373B2 (de) | 1977-08-11 |
| ZA72286B (en) | 1972-09-27 |
| FI55841B (fi) | 1979-06-29 |
| CH535254A (fr) | 1973-03-31 |
| NO134115C (en:Method) | 1976-08-18 |
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