NO800131L - Fremgangsmaate ved fremstilling av nye imidazolderivater - Google Patents
Fremgangsmaate ved fremstilling av nye imidazolderivaterInfo
- Publication number
- NO800131L NO800131L NO800131A NO800131A NO800131L NO 800131 L NO800131 L NO 800131L NO 800131 A NO800131 A NO 800131A NO 800131 A NO800131 A NO 800131A NO 800131 L NO800131 L NO 800131L
- Authority
- NO
- Norway
- Prior art keywords
- imidazolylmethyl
- lower alkyl
- hydrogen
- formula
- stated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 53
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 14
- 239000012312 sodium hydride Substances 0.000 claims description 14
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 14
- -1 alkyl metal hydride Chemical class 0.000 claims description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 4
- ZEFROCQEWXHIEP-UHFFFAOYSA-N 4-(imidazol-1-ylmethyl)phenol Chemical compound C1=CC(O)=CC=C1CN1C=NC=C1 ZEFROCQEWXHIEP-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- DLGROLQAXMKHDV-UHFFFAOYSA-N 2-[4-(1h-imidazol-2-ylmethyl)phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CC1=NC=CN1 DLGROLQAXMKHDV-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 230000009471 action Effects 0.000 abstract description 14
- 108010069102 Thromboxane-A synthase Proteins 0.000 abstract description 13
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 abstract description 10
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 abstract description 10
- KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical class C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 abstract description 9
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 9
- 230000002401 inhibitory effect Effects 0.000 abstract description 9
- 108010064377 prostacyclin synthetase Proteins 0.000 abstract description 9
- 208000019695 Migraine disease Diseases 0.000 abstract description 8
- 230000002792 vascular Effects 0.000 abstract description 7
- 206010027599 migraine Diseases 0.000 abstract description 6
- 208000006011 Stroke Diseases 0.000 abstract description 3
- 208000031225 myocardial ischemia Diseases 0.000 abstract description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 20
- KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 229960001123 epoprostenol Drugs 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 239000002480 mineral oil Substances 0.000 description 10
- 235000010446 mineral oil Nutrition 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- 150000003180 prostaglandins Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 6
- YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 6
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
- 206010019233 Headaches Diseases 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 208000007536 Thrombosis Diseases 0.000 description 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- SBRTVLRSHUJALG-UHFFFAOYSA-N ethyl 2-[4-chloro-2-(1h-imidazol-2-ylmethyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(Cl)C=C1CC1=NC=CN1 SBRTVLRSHUJALG-UHFFFAOYSA-N 0.000 description 4
- 231100000869 headache Toxicity 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- JMIAOBOEYIZTHX-UHFFFAOYSA-N 2-[4-(1h-imidazol-2-ylmethyl)phenoxy]acetic acid;hydrochloride Chemical compound Cl.C1=CC(OCC(=O)O)=CC=C1CC1=NC=CN1 JMIAOBOEYIZTHX-UHFFFAOYSA-N 0.000 description 3
- 102000003960 Ligases Human genes 0.000 description 3
- 108090000364 Ligases Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 235000019270 ammonium chloride Nutrition 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
- 239000003085 diluting agent Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- PBPFVLOPFDLGOZ-UHFFFAOYSA-N ethyl 2-[2-(1h-imidazol-2-ylmethyl)-4-methylphenoxy]acetate Chemical compound CCOC(=O)COC1=CC=C(C)C=C1CC1=NC=CN1 PBPFVLOPFDLGOZ-UHFFFAOYSA-N 0.000 description 3
- DJZMLHPTHGGMCK-UHFFFAOYSA-N ethyl 2-[2-(1h-imidazol-2-ylmethyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC=C1CC1=NC=CN1 DJZMLHPTHGGMCK-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 3
- 210000001589 microsome Anatomy 0.000 description 3
- 208000010125 myocardial infarction Diseases 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 3
- 229960003329 sulfinpyrazone Drugs 0.000 description 3
- KPBKFEFUHSYUHE-UHFFFAOYSA-N 2-(1h-imidazol-2-ylmethyl)phenol Chemical compound OC1=CC=CC=C1CC1=NC=CN1 KPBKFEFUHSYUHE-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- VECKLYYMZDDJSV-UHFFFAOYSA-N 2-[2-(1h-imidazol-2-ylmethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC=C1CC1=NC=CN1 VECKLYYMZDDJSV-UHFFFAOYSA-N 0.000 description 2
- KEZQSHNEWWMKMH-UHFFFAOYSA-N 2-[3-(1h-imidazol-2-ylmethyl)phenoxy]acetic acid;hydrochloride Chemical compound Cl.OC(=O)COC1=CC=CC(CC=2NC=CN=2)=C1 KEZQSHNEWWMKMH-UHFFFAOYSA-N 0.000 description 2
- KPTMBJRGOKWWFO-UHFFFAOYSA-N 2-[4-(1h-imidazol-2-ylmethyl)-2-methoxyphenoxy]acetamide Chemical compound C1=C(OCC(N)=O)C(OC)=CC(CC=2NC=CN=2)=C1 KPTMBJRGOKWWFO-UHFFFAOYSA-N 0.000 description 2
- RVOULTORHRLMFK-UHFFFAOYSA-N 2-[4-(1h-imidazol-2-ylmethyl)phenoxy]-n-methylacetamide Chemical compound C1=CC(OCC(=O)NC)=CC=C1CC1=NC=CN1 RVOULTORHRLMFK-UHFFFAOYSA-N 0.000 description 2
- DVICUTCQLZBEKL-UHFFFAOYSA-N 2-[4-(1h-imidazol-2-ylmethyl)phenoxy]acetamide Chemical compound C1=CC(OCC(=O)N)=CC=C1CC1=NC=CN1 DVICUTCQLZBEKL-UHFFFAOYSA-N 0.000 description 2
- RNDQHHWCXVCMRH-UHFFFAOYSA-N 2-[4-chloro-2-(1h-imidazol-2-ylmethyl)phenoxy]acetamide Chemical compound NC(=O)COC1=CC=C(Cl)C=C1CC1=NC=CN1 RNDQHHWCXVCMRH-UHFFFAOYSA-N 0.000 description 2
- XNHDIEIHYDTQEI-UHFFFAOYSA-N 2-[4-chloro-2-(1h-imidazol-2-ylmethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CC1=NC=CN1 XNHDIEIHYDTQEI-UHFFFAOYSA-N 0.000 description 2
- TVSPPYGAFOVROT-UHFFFAOYSA-N 2-phenoxybutanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC=C1 TVSPPYGAFOVROT-UHFFFAOYSA-N 0.000 description 2
- PGRBAPGAXUSETH-UHFFFAOYSA-N 3-(imidazol-1-ylmethyl)phenol;hydrobromide Chemical compound Br.OC1=CC=CC(CN2C=NC=C2)=C1 PGRBAPGAXUSETH-UHFFFAOYSA-N 0.000 description 2
- DQRKTVIJNCVZAX-UHFFFAOYSA-N 4-(2-pyridin-4-ylethyl)pyridine Chemical compound C=1C=NC=CC=1CCC1=CC=NC=C1 DQRKTVIJNCVZAX-UHFFFAOYSA-N 0.000 description 2
- HRSXTIHSUKYHIQ-UHFFFAOYSA-N 4-[2-(1h-imidazol-2-ylmethyl)-4-methylphenoxy]butanamide Chemical compound CC1=CC=C(OCCCC(N)=O)C(CC=2NC=CN=2)=C1 HRSXTIHSUKYHIQ-UHFFFAOYSA-N 0.000 description 2
- BPUGRJAUHIISKZ-UHFFFAOYSA-N 4-[[2-(1h-imidazol-2-ylmethyl)-4-methylphenoxy]methyl]benzoic acid Chemical compound N=1C=CNC=1CC1=CC(C)=CC=C1OCC1=CC=C(C(O)=O)C=C1 BPUGRJAUHIISKZ-UHFFFAOYSA-N 0.000 description 2
- JYAJHNWYIIOLQD-UHFFFAOYSA-N 4-[[2-(1h-imidazol-2-ylmethyl)phenoxy]methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1COC1=CC=CC=C1CC1=NC=CN1 JYAJHNWYIIOLQD-UHFFFAOYSA-N 0.000 description 2
- GSTJABUYSKSJGZ-UHFFFAOYSA-N 5-[[4-(imidazol-1-ylmethyl)phenoxy]methyl]-2h-tetrazole Chemical compound N=1N=NNC=1COC(C=C1)=CC=C1CN1C=CN=C1 GSTJABUYSKSJGZ-UHFFFAOYSA-N 0.000 description 2
- MARUHZGHZWCEQU-UHFFFAOYSA-N 5-phenyl-2h-tetrazole Chemical compound C1=CC=CC=C1C1=NNN=N1 MARUHZGHZWCEQU-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KECOVMHCXBWBLH-UHFFFAOYSA-N Cl.N1C(=NC=C1)CC1=C(OCC(=O)O)C=CC(=C1)C Chemical compound Cl.N1C(=NC=C1)CC1=C(OCC(=O)O)C=CC(=C1)C KECOVMHCXBWBLH-UHFFFAOYSA-N 0.000 description 2
- 101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 208000008765 Sciatica Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 229940114079 arachidonic acid Drugs 0.000 description 2
- 235000021342 arachidonic acid Nutrition 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000003727 cerebral blood flow Effects 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- KVFICDZWAPMGDB-UHFFFAOYSA-N ethyl 2-[3-(1h-imidazol-2-ylmethyl)phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(CC=2NC=CN=2)=C1 KVFICDZWAPMGDB-UHFFFAOYSA-N 0.000 description 2
- GZLSYHREBYYSNR-UHFFFAOYSA-N ethyl 2-[4-(1h-imidazol-2-ylmethyl)-2-methoxyphenoxy]acetate Chemical compound C1=C(OC)C(OCC(=O)OCC)=CC=C1CC1=NC=CN1 GZLSYHREBYYSNR-UHFFFAOYSA-N 0.000 description 2
- VDSGSADOPBBUOB-UHFFFAOYSA-N ethyl 2-[4-(1h-imidazol-2-ylmethyl)phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCC)=CC=C1CC1=NC=CN1 VDSGSADOPBBUOB-UHFFFAOYSA-N 0.000 description 2
- AFKBZUKKCDRMPZ-UHFFFAOYSA-N ethyl 4-[2-(1h-imidazol-2-ylmethyl)phenoxy]butanoate Chemical compound CCOC(=O)CCCOC1=CC=CC=C1CC1=NC=CN1 AFKBZUKKCDRMPZ-UHFFFAOYSA-N 0.000 description 2
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 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
- 230000004060 metabolic process Effects 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 210000005166 vasculature Anatomy 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OLIXBQIGIJMNBA-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]imidazole Chemical compound COC1=CC=CC(CN2C=NC=C2)=C1 OLIXBQIGIJMNBA-UHFFFAOYSA-N 0.000 description 1
- BFWYTORDSFIVKP-USWFWKISSA-N 15-HPETE Chemical compound CCCCCC(OO)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O BFWYTORDSFIVKP-USWFWKISSA-N 0.000 description 1
- NVWGQOHWAHGNOF-UHFFFAOYSA-N 2-(1h-imidazol-2-ylmethyl)-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2NC=CN=2)=C1 NVWGQOHWAHGNOF-UHFFFAOYSA-N 0.000 description 1
- JXYBKXKGODSOKU-UHFFFAOYSA-N 2-(imidazol-1-ylmethyl)phenol Chemical compound OC1=CC=CC=C1CN1C=NC=C1 JXYBKXKGODSOKU-UHFFFAOYSA-N 0.000 description 1
- OEWPKFGSPYTJDP-UHFFFAOYSA-N 2-(imidazol-1-ylmethyl)phenol;hydrobromide Chemical compound Br.OC1=CC=CC=C1CN1C=NC=C1 OEWPKFGSPYTJDP-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- BUQSWJWPWNNDBR-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-4-methylphenol Chemical compound CN(C)CCC1=CC(C)=CC=C1O BUQSWJWPWNNDBR-UHFFFAOYSA-N 0.000 description 1
- IZWXGVTXYXNUPZ-UHFFFAOYSA-N 2-[4-(1h-imidazol-2-ylmethyl)phenoxy]acetonitrile Chemical compound C1=CC(OCC#N)=CC=C1CC1=NC=CN1 IZWXGVTXYXNUPZ-UHFFFAOYSA-N 0.000 description 1
- AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- UMLFTCYAQPPZER-UHFFFAOYSA-N 4-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=C(C#N)C=C1 UMLFTCYAQPPZER-UHFFFAOYSA-N 0.000 description 1
- MSRCXZCQDLDJEK-UHFFFAOYSA-N 4-[2-(1h-imidazol-2-ylmethyl)phenoxy]butanoic acid Chemical compound OC(=O)CCCOC1=CC=CC=C1CC1=NC=CN1 MSRCXZCQDLDJEK-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
- WPEGHIRPYPPYDO-UHFFFAOYSA-N 4-chloro-2-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(Cl)=CC=C1O WPEGHIRPYPPYDO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- 206010059245 Angiopathy Diseases 0.000 description 1
- 206010003178 Arterial thrombosis Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 101000932768 Conus catus Alpha-conotoxin CIC Proteins 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- 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
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 description 1
- 101000988802 Homo sapiens Hematopoietic prostaglandin D synthase Proteins 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
- 206010027603 Migraine headaches Diseases 0.000 description 1
- SGUKUZOVHSFKPH-UHFFFAOYSA-N PGG2 Natural products C1C2OOC1C(C=CC(OO)CCCCC)C2CC=CCCCC(O)=O SGUKUZOVHSFKPH-UHFFFAOYSA-N 0.000 description 1
- 201000001068 Prinzmetal angina Diseases 0.000 description 1
- 206010049418 Sudden Cardiac Death Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000032109 Transient ischaemic attack Diseases 0.000 description 1
- 206010047163 Vasospasm Diseases 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004931 aggregating effect Effects 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000003368 amide group Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127217 antithrombotic drug Drugs 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000007214 atherothrombosis Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- JMFRWRFFLBVWSI-UHFFFAOYSA-N cis-coniferyl alcohol Natural products COC1=CC(C=CCO)=CC=C1O JMFRWRFFLBVWSI-UHFFFAOYSA-N 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
- 229960002986 dinoprostone Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000010102 embolization Effects 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- MGZFVSUXQXCEHM-UHFFFAOYSA-N ethyl 2-phenoxyacetate Chemical compound CCOC(=O)COC1=CC=CC=C1 MGZFVSUXQXCEHM-UHFFFAOYSA-N 0.000 description 1
- GOUMKYCCYVXJCZ-UHFFFAOYSA-N ethyl 4-[2-(1h-imidazol-2-ylmethyl)-4-methylphenoxy]butanoate Chemical compound CCOC(=O)CCCOC1=CC=C(C)C=C1CC1=NC=CN1 GOUMKYCCYVXJCZ-UHFFFAOYSA-N 0.000 description 1
- CXHYQOJIHAFAPU-UHFFFAOYSA-N ethyl 4-[2-(1h-imidazol-2-ylmethyl)-4-methylphenoxy]butanoate;hydrochloride Chemical compound Cl.CCOC(=O)CCCOC1=CC=C(C)C=C1CC1=NC=CN1 CXHYQOJIHAFAPU-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000003278 haem Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000035874 hyperreactivity Effects 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- ZOAMBXDOGPRZLP-UHFFFAOYSA-N indole-3-acetamide Chemical compound C1=CC=C2C(CC(=O)N)=CNC2=C1 ZOAMBXDOGPRZLP-UHFFFAOYSA-N 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229940118019 malondialdehyde Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000000546 pharmaceutical excipient 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
- 238000011533 pre-incubation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000328 pro-aggregatory effect Effects 0.000 description 1
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- SGUKUZOVHSFKPH-YNNPMVKQSA-N prostaglandin G2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](OO)CCCCC)[C@H]2C\C=C/CCCC(O)=O SGUKUZOVHSFKPH-YNNPMVKQSA-N 0.000 description 1
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- 150000003595 thromboxanes Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- ZENOXNGFMSCLLL-UHFFFAOYSA-N vanillyl alcohol Chemical compound COC1=CC(CO)=CC=C1O ZENOXNGFMSCLLL-UHFFFAOYSA-N 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- 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
- C07D233/60—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 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7902114 | 1979-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO800131L true NO800131L (no) | 1980-07-21 |
Family
ID=10502633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO800131A NO800131L (no) | 1979-01-19 | 1980-01-18 | Fremgangsmaate ved fremstilling av nye imidazolderivater |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US4555516A (es) |
| JP (1) | JPS5946504B2 (es) |
| KR (1) | KR840001707B1 (es) |
| AR (1) | AR222204A1 (es) |
| AT (1) | AT373880B (es) |
| AU (1) | AU517241B2 (es) |
| BE (1) | BE881245A (es) |
| CA (1) | CA1137481A (es) |
| CH (1) | CH646154A5 (es) |
| DD (1) | DD148773A5 (es) |
| DE (1) | DE3001762A1 (es) |
| DK (1) | DK531479A (es) |
| ES (1) | ES487843A0 (es) |
| FI (1) | FI800143A (es) |
| FR (1) | FR2446828A1 (es) |
| GR (1) | GR71914B (es) |
| HU (1) | HU184227B (es) |
| IE (1) | IE49364B1 (es) |
| IL (1) | IL59150A (es) |
| IT (1) | IT1140523B (es) |
| LU (1) | LU82087A1 (es) |
| NL (1) | NL8000333A (es) |
| NO (1) | NO800131L (es) |
| NZ (1) | NZ192640A (es) |
| PH (1) | PH14910A (es) |
| PL (1) | PL123985B1 (es) |
| PT (1) | PT70707A (es) |
| SE (1) | SE8000435L (es) |
| SU (1) | SU906374A3 (es) |
| YU (1) | YU11380A (es) |
| ZA (1) | ZA80298B (es) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK157860C (da) * | 1979-06-07 | 1990-07-30 | Shionogi & Co | Analogifremgangsmaade til fremstilling af benzylimidazolderivater samt farmaceutisk acceptable syreadditionssalte deraf |
| JPS56113766A (en) * | 1980-02-12 | 1981-09-07 | Teijin Ltd | Novel 1-substituted imidazole derivative and its preparation |
| JPS57169452A (en) * | 1981-04-14 | 1982-10-19 | Teikoku Hormone Mfg Co Ltd | Novel phenoxyalkylamide derivative |
| DE3235589A1 (de) | 1982-09-25 | 1984-03-29 | Hoechst Ag, 6230 Frankfurt | Benzylether von phenol-mannich-basen, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen, zwischenprodukte und verfahren zu deren herstellung |
| DE3424944A1 (de) * | 1984-07-06 | 1986-02-06 | Hoechst Ag, 6230 Frankfurt | Neue imidazolyverbindungen, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4978672A (en) * | 1986-03-07 | 1990-12-18 | Ciba-Geigy Corporation | Alpha-heterocyclc substituted tolunitriles |
| US4937250A (en) * | 1988-03-07 | 1990-06-26 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| US5138069A (en) * | 1986-07-11 | 1992-08-11 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking imidazoles |
| US5210079A (en) * | 1988-01-07 | 1993-05-11 | E. I. Du Pont De Nemours And Company | Treatment of chronic renal failure with imidazole angiotensin-II receptor antagonists |
| US4880804A (en) * | 1988-01-07 | 1989-11-14 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking benzimidazoles |
| CA1338238C (en) | 1988-01-07 | 1996-04-09 | David John Carini | Angiotensin ii receptor blocking imidazoles and combinations thereof with diuretics and nsaids |
| US5354867A (en) * | 1988-12-06 | 1994-10-11 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking imidazoles |
| AU645022B2 (en) * | 1989-06-30 | 1994-01-06 | E.I. Du Pont De Nemours And Company | Fused-ring aryl substituted imidazoles |
| US5073566A (en) * | 1989-11-30 | 1991-12-17 | Eli Lilly And Company | Angiotensin ii antagonist 1,3-imidazoles and use thereas |
| US5616599A (en) * | 1991-02-21 | 1997-04-01 | Sankyo Company, Limited | Angiotensin II antagosist 1-biphenylmethylimidazole compounds and their therapeutic use |
| US5332820A (en) * | 1991-05-20 | 1994-07-26 | E. I. Du Pont De Nemours And Company | Dibenzobicyclo(2.2.2) octane angiotensin II antagonists |
| US5401851A (en) * | 1992-06-03 | 1995-03-28 | Eli Lilly And Company | Angiotensin II antagonists |
| US5612360A (en) * | 1992-06-03 | 1997-03-18 | Eli Lilly And Company | Angiotensin II antagonists |
| JP3501484B2 (ja) * | 1992-12-17 | 2004-03-02 | 三共株式会社 | ビフェニル誘導体 |
| AU2352295A (en) * | 1994-04-27 | 1995-11-16 | Nippon Soda Co., Ltd. | Imidazole derivative and process for producing the same |
| TW434240B (en) * | 1995-06-20 | 2001-05-16 | Zeneca Ltd | Aromatic compounds, preparation thereof and pharmaceutical composition comprising same |
| EE03524B1 (et) * | 1995-12-27 | 2001-10-15 | Yoshitomi Pharmaceutical Industries, Ltd. | Vahend diabeedi komplikatsioonide profülaktikaks ja raviks |
| JP4056589B2 (ja) * | 1996-07-19 | 2008-03-05 | 武田薬品工業株式会社 | 複素環化合物、その製造法および用途 |
| IT1295405B1 (it) | 1997-09-30 | 1999-05-12 | Merck Sharp & Dohme Italia S P | Uso di un antagonista recettoriale di angiotensina ii per la preparazione di farmaci per aumentare il tasso di sopravvivenza di |
| KR100423890B1 (ko) * | 2000-10-19 | 2004-03-24 | 씨제이 주식회사 | 세팔로스포린 유도체의 새로운 제조방법 |
| TW200505913A (en) * | 2003-03-28 | 2005-02-16 | Hoffmann La Roche | Novel oxazole derivatives, their manufacture and use as pharmaceutical agents |
| CN117624052B (zh) * | 2024-01-26 | 2024-04-12 | 四川益能康生环保科技有限公司 | 一种用于捕集二氧化碳的离子液体及其制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH271776A (de) * | 1949-01-06 | 1950-11-15 | Ag J R Geigy | Verfahren zur Herstellung eines basischen Äthers eines ortho-substituierten Phenols. |
| US3498999A (en) * | 1966-04-20 | 1970-03-03 | Bristol Myers Co | 1-phenoxy and substituted phenoxy-3-(5-tetrazolyl) propanes |
| IE40911B1 (en) * | 1974-04-11 | 1979-09-12 | Schering Ag | Imidazole derivatives and process for their manufacture |
| DE2461406C2 (de) * | 1974-12-24 | 1984-06-14 | Bayer Ag, 5090 Leverkusen | Azolyl-(1)-methane und deren Salze, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel |
| US4085209A (en) * | 1975-02-05 | 1978-04-18 | Rohm And Haas Company | Preparation and safening effect of 1-substituted imidazole metal salt complexes |
| DE2646143A1 (de) * | 1976-10-13 | 1978-04-20 | Bayer Ag | 4,5-dichlor-imidazol-1-carbonsaeure- arylester, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel |
| JPS5951943B2 (ja) * | 1978-08-21 | 1984-12-17 | キツセイ薬品工業株式会社 | 新規なイミダゾ−ル誘導体 |
-
1979
- 1979-12-13 DK DK531479A patent/DK531479A/da not_active Application Discontinuation
-
1980
- 1980-01-09 US US06/110,711 patent/US4555516A/en not_active Expired - Lifetime
- 1980-01-15 LU LU82087A patent/LU82087A1/fr unknown
- 1980-01-17 ZA ZA00800298A patent/ZA80298B/xx unknown
- 1980-01-17 AR AR279667A patent/AR222204A1/es active
- 1980-01-17 YU YU00113/80A patent/YU11380A/xx unknown
- 1980-01-17 IL IL59150A patent/IL59150A/xx unknown
- 1980-01-17 FI FI800143A patent/FI800143A/fi not_active Application Discontinuation
- 1980-01-17 GR GR60978A patent/GR71914B/el unknown
- 1980-01-17 AT AT0024680A patent/AT373880B/de not_active IP Right Cessation
- 1980-01-17 IT IT19276/80A patent/IT1140523B/it active
- 1980-01-17 PT PT70707A patent/PT70707A/pt unknown
- 1980-01-18 DD DD80218534A patent/DD148773A5/de unknown
- 1980-01-18 IE IE102/80A patent/IE49364B1/en unknown
- 1980-01-18 ES ES487843A patent/ES487843A0/es active Granted
- 1980-01-18 JP JP55004474A patent/JPS5946504B2/ja not_active Expired
- 1980-01-18 SU SU802872552A patent/SU906374A3/ru active
- 1980-01-18 NL NL8000333A patent/NL8000333A/nl not_active Application Discontinuation
- 1980-01-18 CH CH42080A patent/CH646154A5/de not_active IP Right Cessation
- 1980-01-18 SE SE8000435A patent/SE8000435L/xx not_active Application Discontinuation
- 1980-01-18 DE DE19803001762 patent/DE3001762A1/de not_active Ceased
- 1980-01-18 NO NO800131A patent/NO800131L/no unknown
- 1980-01-18 CA CA000343989A patent/CA1137481A/en not_active Expired
- 1980-01-18 HU HU80105A patent/HU184227B/hu unknown
- 1980-01-18 FR FR8001082A patent/FR2446828A1/fr active Granted
- 1980-01-18 BE BE0/199041A patent/BE881245A/fr not_active IP Right Cessation
- 1980-01-18 AU AU54743/80A patent/AU517241B2/en not_active Ceased
- 1980-01-19 PL PL1980221461A patent/PL123985B1/pl unknown
- 1980-01-19 KR KR1019800000190A patent/KR840001707B1/ko active
- 1980-01-21 PH PH23530A patent/PH14910A/en unknown
- 1980-06-17 NZ NZ192640A patent/NZ192640A/en unknown
-
1981
- 1981-07-27 US US06/286,808 patent/US4448781A/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO800131L (no) | Fremgangsmaate ved fremstilling av nye imidazolderivater | |
| NO152217B (no) | Analogifremgangsmaate ved fremstilling av nye terapeutisk aktive 3-(1-imidazolylalkyl)indoler | |
| US4602016A (en) | N-(phenoxyalkyl)imidazoles as selective inhibitors of the thromboxane synthetase enzyme and pharmaceutical compositions thereof | |
| EP0054417B1 (en) | Indole thromboxane synthetase inhibitors, processes for their preparation, and pharmaceutical compositions containing them | |
| US4339583A (en) | (Imidazolylmethyl)pyridine compounds as thromboxane synthetase inhibitors | |
| GB2041363A (en) | N-Benzyl-imidazoles | |
| EP0035863B1 (en) | Imidazole derivatives, process for their preparation and pharmaceutical compositions thereof | |
| US4451472A (en) | Inhibition of thromboxane synthetase with 3-(heteroalkyl)-indolyl-acrylic acid derivatives | |
| US4259345A (en) | 2-(Imidazol-1-ylmethyl)pyrroles | |
| US4230714A (en) | Imidazole therapeutic agents | |
| GB2102795A (en) | Indole derivatives | |
| GB2068950A (en) | Pyridine Derivatives | |
| GB2101115A (en) | Thromboxane synthetase inhibitors |