NO855196L - Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazoderivater. - Google Patents
Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazoderivater.Info
- Publication number
- NO855196L NO855196L NO855196A NO855196A NO855196L NO 855196 L NO855196 L NO 855196L NO 855196 A NO855196 A NO 855196A NO 855196 A NO855196 A NO 855196A NO 855196 L NO855196 L NO 855196L
- Authority
- NO
- Norway
- Prior art keywords
- group
- residues
- methoxy
- general formula
- imidazo
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 9
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 amino, hydroxy, methoxy Chemical group 0.000 claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 25
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 230000000269 nucleophilic effect Effects 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 6
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000005238 imidazo[1,2-a]pyrimidines Chemical class 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 4
- GKBYFGMFZVGBIU-UHFFFAOYSA-N (4-imidazo[1,2-a]pyrazin-2-yl-3-methoxyphenyl) methanesulfonate Chemical compound COC1=CC(OS(C)(=O)=O)=CC=C1C1=CN(C=CN=C2)C2=N1 GKBYFGMFZVGBIU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 150000005236 imidazo[1,2-a]pyrazines Chemical class 0.000 claims description 2
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 claims description 2
- YLOHMDLHIBDRHJ-UHFFFAOYSA-N imidazo[2,1-c][1,2,4]triazine Chemical class C1=CN=NC2=NC=CN21 YLOHMDLHIBDRHJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 claims 5
- 150000004892 pyridazines Chemical class 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 238000002844 melting Methods 0.000 description 61
- 230000008018 melting Effects 0.000 description 61
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 19
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 10
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 9
- DTXVKPOKPFWSFF-UHFFFAOYSA-N 3(S)-hydroxy-13-cis-eicosenoyl-CoA Chemical compound NC1=CC=C(Cl)N=N1 DTXVKPOKPFWSFF-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000036772 blood pressure Effects 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
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- LETVJWLLIMJADE-UHFFFAOYSA-N pyridazin-3-amine Chemical compound NC1=CC=CN=N1 LETVJWLLIMJADE-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RWZQTVFMAPBWPF-UHFFFAOYSA-N (4-imidazo[1,2-a]pyrimidin-2-yl-3-methoxyphenyl) methanesulfonate Chemical group COC1=CC(OS(C)(=O)=O)=CC=C1C1=CN(C=CC=N2)C2=N1 RWZQTVFMAPBWPF-UHFFFAOYSA-N 0.000 description 2
- MJIWQHRXSLOUJN-UHFFFAOYSA-N 1,2,4-triazin-3-amine Chemical compound NC1=NC=CN=N1 MJIWQHRXSLOUJN-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- MZWNMPVRUFGZKY-UHFFFAOYSA-N 2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=CN(C=CC=N2)C2=N1 MZWNMPVRUFGZKY-UHFFFAOYSA-N 0.000 description 2
- XQJAHBHCLXUGEP-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CBr)C=C1 XQJAHBHCLXUGEP-UHFFFAOYSA-N 0.000 description 2
- IBOKEQFMMUALBP-UHFFFAOYSA-N 3,5-bis(methylsulfanyl)-1,2,4-triazin-6-amine Chemical compound CSC1=NN=C(N)C(SC)=N1 IBOKEQFMMUALBP-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- ZSTSLCVMYYYTNK-UHFFFAOYSA-N 4-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-3-methoxybenzenesulfonamide Chemical compound COC1=CC(S(N)(=O)=O)=CC=C1C1=CN(N=C(Cl)C=C2)C2=N1 ZSTSLCVMYYYTNK-UHFFFAOYSA-N 0.000 description 2
- FGYWZNDKJDHGAI-UHFFFAOYSA-N 4-imidazo[1,2-a]pyrimidin-2-yl-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=CN(C=CC=N2)C2=N1 FGYWZNDKJDHGAI-UHFFFAOYSA-N 0.000 description 2
- GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical compound CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 description 2
- UIUAYUFIFZRRSB-UHFFFAOYSA-N 6-chloro-2-(1-methoxynaphthalen-2-yl)imidazo[1,2-a]pyridine Chemical compound C1=C(Cl)C=CC2=NC(C3=C(C4=CC=CC=C4C=C3)OC)=CN21 UIUAYUFIFZRRSB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000007098 aminolysis reaction Methods 0.000 description 2
- 230000002785 anti-thrombosis Effects 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- GCRUEXFJNQVIJM-UHFFFAOYSA-N hydron;pyridazin-3-amine;chloride Chemical compound Cl.NC1=CC=CN=N1 GCRUEXFJNQVIJM-UHFFFAOYSA-N 0.000 description 2
- 150000004942 imidazo[1,2-b]pyridazines Chemical class 0.000 description 2
- KICAUGXUKBYQLR-UHFFFAOYSA-N imidazo[2,1-f][1,2,4]triazine Chemical class N1=CN=CC2=NC=CN21 KICAUGXUKBYQLR-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 210000005240 left ventricle Anatomy 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- UAUCSPNOPSGZBM-UHFFFAOYSA-N n-(2-imidazo[1,2-a]pyrimidin-2-yl-5-methoxyphenyl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(OC)=CC=C1C1=CN(C=CC=N2)C2=N1 UAUCSPNOPSGZBM-UHFFFAOYSA-N 0.000 description 2
- LXDBOJUYKJVXKW-UHFFFAOYSA-N n-(4-imidazo[1,2-a]pyridin-2-yl-3-methoxyphenyl)methanesulfonamide Chemical group COC1=CC(NS(C)(=O)=O)=CC=C1C1=CN(C=CC=C2)C2=N1 LXDBOJUYKJVXKW-UHFFFAOYSA-N 0.000 description 2
- SFNFROBAYLDPAS-UHFFFAOYSA-N n-(5-hydroxy-2-imidazo[1,2-a]pyridin-2-ylphenyl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(O)=CC=C1C1=CN(C=CC=C2)C2=N1 SFNFROBAYLDPAS-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000009090 positive inotropic effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- CVGLQMWEFHKNQY-UHFFFAOYSA-N (3-hydroxy-4-imidazo[1,2-a]pyrimidin-2-ylphenyl) methanesulfonate Chemical compound OC1=CC(OS(=O)(=O)C)=CC=C1C1=CN(C=CC=N2)C2=N1 CVGLQMWEFHKNQY-UHFFFAOYSA-N 0.000 description 1
- ULOIHOUJMZLPRD-UHFFFAOYSA-N (4-imidazo[1,2-a]pyridin-2-yl-3-methoxyphenyl) methanesulfonate Chemical compound COC1=CC(OS(C)(=O)=O)=CC=C1C1=CN(C=CC=C2)C2=N1 ULOIHOUJMZLPRD-UHFFFAOYSA-N 0.000 description 1
- KCNZPLNTMJITRQ-UHFFFAOYSA-N (4-imidazo[1,2-a]pyrimidin-2-ylphenyl) methanesulfonate Chemical compound C1=CC(OS(=O)(=O)C)=CC=C1C1=CN(C=CC=N2)C2=N1 KCNZPLNTMJITRQ-UHFFFAOYSA-N 0.000 description 1
- NFJJQOJFHSERQK-UHFFFAOYSA-N (4-imidazo[1,2-b]pyridazin-2-yl-3-methoxyphenyl) methanesulfonate Chemical compound COC1=CC(OS(C)(=O)=O)=CC=C1C1=CN(N=CC=C2)C2=N1 NFJJQOJFHSERQK-UHFFFAOYSA-N 0.000 description 1
- HIYDLIWJQWRJFF-UHFFFAOYSA-N (4-imidazo[1,2-d][1,2,4]triazin-2-yl-3-methoxyphenyl) methanesulfonate Chemical compound COC1=CC(OS(C)(=O)=O)=CC=C1C1=CN(C=NN=C2)C2=N1 HIYDLIWJQWRJFF-UHFFFAOYSA-N 0.000 description 1
- KKCXAHYCISDWPZ-UHFFFAOYSA-N (4-imidazo[2,1-f][1,2,4]triazin-6-yl-3-methoxyphenyl) methanesulfonate Chemical compound COC1=CC(OS(C)(=O)=O)=CC=C1C1=CN(N=CN=C2)C2=N1 KKCXAHYCISDWPZ-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 1
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- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843446778 DE3446778A1 (de) | 1984-12-21 | 1984-12-21 | Neue imidazoderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO855196L true NO855196L (no) | 1986-06-23 |
Family
ID=6253488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO855196A NO855196L (no) | 1984-12-21 | 1985-12-20 | Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazoderivater. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4716169A (xx) |
| EP (1) | EP0185345A1 (xx) |
| JP (1) | JPS61152681A (xx) |
| AU (1) | AU5154585A (xx) |
| DD (1) | DD242407A5 (xx) |
| DE (1) | DE3446778A1 (xx) |
| DK (1) | DK590185A (xx) |
| ES (2) | ES8703472A1 (xx) |
| FI (1) | FI855080A (xx) |
| GR (1) | GR853124B (xx) |
| HU (1) | HU194562B (xx) |
| NO (1) | NO855196L (xx) |
| PT (1) | PT81716B (xx) |
| ZA (1) | ZA859729B (xx) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4833149A (en) * | 1986-09-22 | 1989-05-23 | Ortho Pharmaceutical Corporation | 2- or 3-aryl substituted imidazo[1,2-a]pyridines |
| GB8719368D0 (en) * | 1987-08-15 | 1987-09-23 | Wellcome Found | Heterocyclic compounds |
| SE8704248D0 (sv) * | 1987-10-30 | 1987-10-30 | Haessle Ab | Medical use |
| EP0471236B1 (en) * | 1990-07-30 | 1995-03-15 | Takeda Chemical Industries, Ltd. | Imidazopyridine derivatives and their use |
| US6127576A (en) * | 1996-12-20 | 2000-10-03 | American Cyanamid Company | Aminophenyl ketone derivatives and a method for the preparation thereof |
| JP4327915B2 (ja) * | 1998-03-30 | 2009-09-09 | 株式会社デ・ウエスタン・セラピテクス研究所 | スルフォンアミド誘導体 |
| US6596731B2 (en) | 2001-03-27 | 2003-07-22 | Hoffmann-La Roche Inc. | Substituted imidazo[1,2-A] pyridine derivatives |
| WO2007033080A2 (en) * | 2005-09-12 | 2007-03-22 | Emory University | Alzheimer's disease imaging agents |
| US7723336B2 (en) * | 2005-09-22 | 2010-05-25 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| EP2021340B1 (en) * | 2006-04-21 | 2014-07-23 | The Government Of The United States, As Represented by The Secretary Of Health And Human Services | Beta-amyloid pet imaging agents |
| EP1964841A1 (en) * | 2007-02-28 | 2008-09-03 | sanofi-aventis | Imidazo[1,2-a]azine and their use as pharmaceuticals |
| EP1964840A1 (en) * | 2007-02-28 | 2008-09-03 | sanofi-aventis | Imidazo[1,2-a]pyridines and their use as pharmaceuticals |
| US7868001B2 (en) | 2007-11-02 | 2011-01-11 | Hutchison Medipharma Enterprises Limited | Cytokine inhibitors |
| JP5394404B2 (ja) * | 2008-02-06 | 2014-01-22 | ブリストル−マイヤーズ スクイブ カンパニー | キナーゼ阻害剤として有用な置換イミダゾピリダジン類 |
| EP2280706B1 (en) * | 2008-05-14 | 2013-01-02 | Otsuka Pharmaceutical Factory, Inc. | Lipoprotein lipase-activating compositions comprising benzene derivatives |
| JP6101343B2 (ja) * | 2012-04-26 | 2017-03-22 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 血小板凝集を治療するためのプロテアーゼ活性化受容体４（ｐａｒ４）阻害剤としてのイミダゾチアジアゾールおよびイミダゾピリダジン誘導体 |
| CN104540835B (zh) | 2012-04-26 | 2017-08-08 | 百时美施贵宝公司 | 用于治疗血小板聚集的作为蛋白酶激活受体4(par4)抑制剂的咪唑并噻二唑衍生物 |
| HUE060743T2 (hu) * | 2012-04-26 | 2023-04-28 | Bristol Myers Squibb Co | Gyógyszerészeti kompozíciók, amelyek tartalmaznak imidazothiadiazol- és imidazopiridazinszármazékokat mint proteáz aktívált receptor 4 (PAR4) inhibitorokat trombocitaaggregációk kezelésére |
| US9598419B1 (en) | 2014-06-24 | 2017-03-21 | Universite De Montreal | Imidazotriazine and imidazodiazine compounds |
| US9617279B1 (en) | 2014-06-24 | 2017-04-11 | Bristol-Myers Squibb Company | Imidazooxadiazole compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS523957B2 (xx) * | 1974-03-14 | 1977-01-31 | ||
| US4166851A (en) * | 1977-05-16 | 1979-09-04 | Merck & Co., Inc. | Certain imidazo(1,2a)pyridine derivatives |
| PT77844B (en) * | 1982-12-27 | 1986-05-08 | Lilly Co Eli | Process for preparing substituted imidazopyrimidines -pyrazines and -triazines |
-
1984
- 1984-12-21 DE DE19843446778 patent/DE3446778A1/de not_active Withdrawn
-
1985
- 1985-12-16 EP EP85116025A patent/EP0185345A1/de not_active Withdrawn
- 1985-12-17 US US06/810,008 patent/US4716169A/en not_active Expired - Fee Related
- 1985-12-17 DD DD85284542A patent/DD242407A5/de unknown
- 1985-12-18 DK DK590185A patent/DK590185A/da not_active Application Discontinuation
- 1985-12-19 FI FI855080A patent/FI855080A/fi not_active Application Discontinuation
- 1985-12-19 PT PT81716A patent/PT81716B/pt unknown
- 1985-12-20 AU AU51545/85A patent/AU5154585A/en not_active Abandoned
- 1985-12-20 HU HU854933A patent/HU194562B/hu unknown
- 1985-12-20 GR GR853124A patent/GR853124B/el unknown
- 1985-12-20 NO NO855196A patent/NO855196L/no unknown
- 1985-12-20 JP JP60287602A patent/JPS61152681A/ja active Pending
- 1985-12-20 ES ES550241A patent/ES8703472A1/es not_active Expired
- 1985-12-20 ZA ZA859729A patent/ZA859729B/xx unknown
-
1986
- 1986-07-23 ES ES556974A patent/ES8801276A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0185345A1 (de) | 1986-06-25 |
| FI855080A (fi) | 1986-06-22 |
| PT81716B (de) | 1987-10-15 |
| HU194562B (en) | 1988-02-29 |
| ES8703472A1 (es) | 1987-02-16 |
| US4716169A (en) | 1987-12-29 |
| FI855080A0 (fi) | 1985-12-19 |
| ES550241A0 (es) | 1987-02-16 |
| AU5154585A (en) | 1986-06-26 |
| ES8801276A1 (es) | 1988-01-01 |
| HUT40434A (en) | 1986-12-28 |
| DK590185D0 (da) | 1985-12-18 |
| GR853124B (xx) | 1986-04-22 |
| ES556974A0 (es) | 1988-01-01 |
| PT81716A (de) | 1986-01-01 |
| DE3446778A1 (de) | 1986-07-03 |
| DD242407A5 (de) | 1987-01-28 |
| DK590185A (da) | 1986-06-22 |
| ZA859729B (en) | 1987-08-26 |
| JPS61152681A (ja) | 1986-07-11 |
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