NO855196L - Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazoderivater. - Google Patents

Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazoderivater.

Info

Publication number: NO855196L
Authority: NO; Norway
Prior art keywords: group; residues; methoxy; general formula; imidazo
Prior art date: 1984-12-21

Application number

NO855196A

Other languages

English (en)

Norwegian (no)

Inventor

Joachim Heider

Norbert Hauel

Volkhard Austel

Klaus Noll

Andreas Bomhard

Jacques Van Meel

Willi Diederen

Original Assignee

Thomae Gmbh Dr K

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-12-21

Filing date

1985-12-20

Publication date

1986-06-23

1985-12-20 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1986-06-23 Publication of NO855196L publication Critical patent/NO855196L/no

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
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
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

- 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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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Diabetes (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO855196A 1984-12-21 1985-12-20 Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazoderivater. NO855196L (no)

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 (ja)
EP (1)	EP0185345A1 (ja)
JP (1)	JPS61152681A (ja)
AU (1)	AU5154585A (ja)
DD (1)	DD242407A5 (ja)
DE (1)	DE3446778A1 (ja)
DK (1)	DK590185A (ja)
ES (2)	ES8703472A1 (ja)
FI (1)	FI855080A (ja)
GR (1)	GR853124B (ja)
HU (1)	HU194562B (ja)
NO (1)	NO855196L (ja)
PT (1)	PT81716B (ja)
ZA (1)	ZA859729B (ja)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
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
ATE119774T1 (de) *	1990-07-30	1995-04-15	Takeda Chemical Industries Ltd	Imidazopyridinderivate und ihre verwendung.
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
US20080219922A1 (en) *	2005-09-12	2008-09-11	Goodman Mark M	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
EP1964840A1 (en) *	2007-02-28	2008-09-03	sanofi-aventis	Imidazo[1,2-a]pyridines and their use as pharmaceuticals
EP1964841A1 (en) *	2007-02-28	2008-09-03	sanofi-aventis	Imidazo[1,2-a]azine and their use as pharmaceuticals
US7868001B2 (en)	2007-11-02	2011-01-11	Hutchison Medipharma Enterprises Limited	Cytokine inhibitors
WO2009100375A1 (en) *	2008-02-06	2009-08-13	Bristol-Myers Squibb Company	Substituted imidazopyridazines useful as kinase inhibitors
AU2008356303B2 (en) *	2008-05-14	2013-05-02	Otsuka Pharmaceutical Factory, Inc.	Lipoprotein lipase-activating compositions comprising benzene derivates
CA2871599A1 (en) *	2012-04-26	2013-10-31	Bristol-Myers Squibb Company	Imidazothiadiazole and imidazopyridazine derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation
PL2841437T3 (pl) *	2012-04-26	2017-12-29	Bristol-Myers Squibb Company	Pochodne imidazotiadiazolu i imidazopirazyny jako inhibitory receptora 4 (par4) aktywowanego proteazą do leczenia agregacji płytek
AU2013251683A1 (en)	2012-04-26	2014-12-18	Bristol-Myers Squibb Company	Imidazothiadiazole derivatives as protease activated receptor 4 (PAR4) inhibitors for treating platelet aggregation
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

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS523957B2 (ja) *	1974-03-14	1977-01-31
US4166851A (en) *	1977-05-16	1979-09-04	Merck & Co., Inc.	Certain imidazo(1,2a)pyridine derivatives
ZA839398B (en) *	1982-12-27	1985-08-28	Lilly Co Eli	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 ZA ZA859729A patent/ZA859729B/xx unknown
- 1985-12-20 HU HU854933A patent/HU194562B/hu unknown
- 1985-12-20 ES ES550241A patent/ES8703472A1/es not_active Expired
- 1985-12-20 GR GR853124A patent/GR853124B/el unknown
- 1985-12-20 JP JP60287602A patent/JPS61152681A/ja active Pending
- 1985-12-20 NO NO855196A patent/NO855196L/no unknown
- 1985-12-20 AU AU51545/85A patent/AU5154585A/en not_active Abandoned
1986
- 1986-07-23 ES ES556974A patent/ES8801276A1/es not_active Expired

Also Published As

Publication number	Publication date
FI855080A0 (fi)	1985-12-19
AU5154585A (en)	1986-06-26
FI855080A (fi)	1986-06-22
JPS61152681A (ja)	1986-07-11
HUT40434A (en)	1986-12-28
DK590185D0 (da)	1985-12-18
ES550241A0 (es)	1987-02-16
EP0185345A1 (de)	1986-06-25
GR853124B (ja)	1986-04-22
ES556974A0 (es)	1988-01-01
US4716169A (en)	1987-12-29
HU194562B (en)	1988-02-29
DD242407A5 (de)	1987-01-28
ES8801276A1 (es)	1988-01-01
PT81716B (de)	1987-10-15
ES8703472A1 (es)	1987-02-16
DE3446778A1 (de)	1986-07-03
PT81716A (de)	1986-01-01
DK590185A (da)	1986-06-22
ZA859729B (en)	1987-08-26

Publication	Publication Date	Title
NO855196L (no)	1986-06-23	Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazoderivater.
US4963561A (en)	1990-10-16	Imidazopyridines, their preparation and use
KR100523120B1 (ko)	2005-10-20	Ｐ38 단백질 키나제 저해제로서 헤테로알킬아미노-치환된이환 질소 헤테로환
NO845252L (no)	1985-07-01	Analogifremgangsmaate for fremstilling av terapeutisk aktive 2-fenyl-imidazol-derivater
EP3409278A1 (en)	2018-12-05	Heterocyclic protein kinase inhibitors
MXPA05001332A (es)	2005-04-28	6-alcoxi-pirido-pirimidinas como inhibidores de cinasa del map p-38.
JPH0770128A (ja)	1995-03-14	ピラゾロピリミジノン誘導体
NO832356L (no)	1984-01-02	Fremgangsmaate for fremstilling av farmakologisk aktive imidazolderivater.
EP1315727B1 (en)	2005-06-29	7-oxo pyridopyrimidines
NO842684L (no)	1985-01-07	Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazol-derivater
NO152373B (no)	1985-06-10	Analogifremgangsmaate for fremstilling av farmakologisk aktive 8-fenyl-purin-derivater
NO855197L (no)	1986-06-23	Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazoderivater.
SK23099A3 (en)	1999-08-06	3-substituted pyrido[4',3':4,5]thieno[2,3-d]pyrimidine derivatives, their preparation and their use
AU2002212147A1 (en)	2002-06-06	7-OXO pyridopyrimidines
NO151287B (no)	1984-12-03	Analogifremgangsmaate for fremstilling av terapeutisk aktive 9-hydrazono-6,7,8,9-tetrahydro-4h-pyrido(1,2-a)-pyrimidinderivater
PT1685131E (pt)	2007-05-31	''pirido-7-pirimidin-7-onas substituídas com hidroxialquino''
MXPA05011103A (es)	2005-12-12	Compuestos de quinazolina.
US6387912B1 (en)	2002-05-14	Utilization of pyrimidine derivatives for preventing and treating cerebral ischaemia
TW201139434A (en)	2011-11-16	5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine derivatives, preparation thereof and therapeutic use thereof
JPS6366183A (ja)	1988-03-24	新規の２−チアゾリルイミダゾ〔１，２−ａ〕ピリミジン及びそれらの酸付加塩、それらの製造方法並びにそれらの医薬としての使用
NO854964L (no)	1986-06-13	Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazoderivater.
Parra et al.	2001	Imidazo [1, 2-a] quinoxalines: synthesis and cyclic nucleotide phosphodiesterase inhibitory activity
Martin et al.	1969	The synthesis of lmidazo [4, 5‐d] pyridazines. VI. v‐Triazolo [4, 5‐d] pyridazines, pyrazino [2, 3‐d] pyridazines and 7H‐Imidazo [4, 5‐d] tetrazolo [1, 5‐b] pyridazine
NO845170L (no)	1985-06-24	Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazolderivater.
NZ207349A (en)	1987-03-06	Triazolo(4,3-c)pyrimidines and triazolo(1,5-c)pyrimidines and pharmaceutical compositions