SE436359B - Analogiforfarande for framstellning av 4-substituerade imidazo/1,2-a/kinoxaliner - Google Patents
Analogiforfarande for framstellning av 4-substituerade imidazo/1,2-a/kinoxalinerInfo
- Publication number
- SE436359B SE436359B SE7800138A SE7800138A SE436359B SE 436359 B SE436359 B SE 436359B SE 7800138 A SE7800138 A SE 7800138A SE 7800138 A SE7800138 A SE 7800138A SE 436359 B SE436359 B SE 436359B
- Authority
- SE
- Sweden
- Prior art keywords
- carbon atoms
- water
- formamide
- quinoxaline
- imidazo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 35
- 238000002360 preparation method Methods 0.000 title claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 19
- -1 nitro, amino Chemical group 0.000 claims description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 150000003252 quinoxalines Chemical class 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 2
- VKXZCHMZYHIJSG-UHFFFAOYSA-N 4-(4-chlorophenyl)imidazo[1,2-a]quinoxaline Chemical compound C1=CC(Cl)=CC=C1C1=NC2=CC=CC=C2N2C1=NC=C2 VKXZCHMZYHIJSG-UHFFFAOYSA-N 0.000 claims 1
- LCIFAJPMIUOMPP-UHFFFAOYSA-N 4-(4-fluorophenyl)imidazo[1,2-a]quinoxaline Chemical compound C1=CC(F)=CC=C1C1=NC2=CC=CC=C2N2C1=NC=C2 LCIFAJPMIUOMPP-UHFFFAOYSA-N 0.000 claims 1
- XUHKIUILIBTLRT-UHFFFAOYSA-N 4-pentylimidazo[1,2-a]quinoxaline Chemical compound CCCCCC1=NC2=CC=CC=C2N2C1=NC=C2 XUHKIUILIBTLRT-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- MBNJXEBHBSSYNG-UHFFFAOYSA-N n-(4-methylphenyl)imidazo[1,2-a]quinoxalin-4-amine Chemical compound C1=CC(C)=CC=C1NC1=NC2=CC=CC=C2N2C1=NC=C2 MBNJXEBHBSSYNG-UHFFFAOYSA-N 0.000 claims 1
- RKQVLXJWKRQGNF-UHFFFAOYSA-N n-phenylimidazo[1,2-a]quinoxalin-4-amine Chemical compound N=1C2=CC=CC=C2N2C=CN=C2C=1NC1=CC=CC=C1 RKQVLXJWKRQGNF-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 51
- 150000001875 compounds Chemical class 0.000 description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 38
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 206010030113 Oedema Diseases 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000003018 immunosuppressive agent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 230000000843 anti-fungal effect Effects 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 239000013068 control sample Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 150000002460 imidazoles Chemical class 0.000 description 5
- 229940125721 immunosuppressive agent Drugs 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 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 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 229940121375 antifungal agent Drugs 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000021633 leukocyte mediated immunity Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- MOJYDLJMKAMQDC-UHFFFAOYSA-N 2-phenyl-1h-imidazol-5-amine Chemical compound N1C(N)=CN=C1C1=CC=CC=C1 MOJYDLJMKAMQDC-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 210000002683 foot Anatomy 0.000 description 3
- 210000000548 hind-foot Anatomy 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- HVECTIQVQPUSEX-UHFFFAOYSA-N 2-imidazol-1-ylaniline Chemical compound NC1=CC=CC=C1N1C=NC=C1 HVECTIQVQPUSEX-UHFFFAOYSA-N 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- 208000006313 Delayed Hypersensitivity Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 208000002474 Tinea Diseases 0.000 description 2
- 241000130764 Tinea Species 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 230000005951 type IV hypersensitivity Effects 0.000 description 2
- OHXHFXHOPMUAAK-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)aniline Chemical compound NC1=CC=CC=C1C1=NC=CN1 OHXHFXHOPMUAAK-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 241001260018 Arthroderma uncinatum Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- 241000222178 Candida tropicalis Species 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 101100233684 Drosophila melanogaster Itgbn gene Proteins 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 208000005232 Glossitis Diseases 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 108010006464 Hemolysin Proteins Proteins 0.000 description 1
- 206010019755 Hepatitis chronic active Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001676573 Minium Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241001049988 Mycobacterium tuberculosis H37Ra Species 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 206010043866 Tinea capitis Diseases 0.000 description 1
- 201000010618 Tinea cruris Diseases 0.000 description 1
- 206010049591 Tinea imbricata Diseases 0.000 description 1
- 206010067197 Tinea manuum Diseases 0.000 description 1
- 241000466638 Tulostoma albicans Species 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 206010046914 Vaginal infection Diseases 0.000 description 1
- 201000008100 Vaginitis Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- ORWKVZNEPHTCQE-UHFFFAOYSA-N acetic formic anhydride Chemical compound CC(=O)OC=O ORWKVZNEPHTCQE-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 208000028004 allergic respiratory disease Diseases 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 201000003465 angular cheilitis Diseases 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000000656 anti-yeast Effects 0.000 description 1
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- 239000003429 antifungal agent Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 208000002479 balanitis Diseases 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
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- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
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- 239000003228 hemolysin Substances 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
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- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 201000005962 mycosis fungoides Diseases 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75764077A | 1977-01-07 | 1977-01-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7800138L SE7800138L (sv) | 1978-07-08 |
| SE436359B true SE436359B (sv) | 1984-12-03 |
Family
ID=25048641
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7800138A SE436359B (sv) | 1977-01-07 | 1978-01-05 | Analogiforfarande for framstellning av 4-substituerade imidazo/1,2-a/kinoxaliner |
| SE8300945A SE460477B (sv) | 1977-01-07 | 1983-02-21 | 1-(2-acylaminofenyl)imidazoler till anvaendning sommellanprodukter |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8300945A SE460477B (sv) | 1977-01-07 | 1983-02-21 | 1-(2-acylaminofenyl)imidazoler till anvaendning sommellanprodukter |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4160097A (en, 2012) |
| JP (2) | JPS5387398A (en, 2012) |
| AU (1) | AU521807B2 (en, 2012) |
| BE (1) | BE862608A (en, 2012) |
| CA (1) | CA1149385A (en, 2012) |
| CH (2) | CH636102A5 (en, 2012) |
| CS (1) | CS200232B2 (en, 2012) |
| DE (2) | DE2800480A1 (en, 2012) |
| DK (1) | DK157024C (en, 2012) |
| FI (1) | FI64374C (en, 2012) |
| FR (1) | FR2376858A1 (en, 2012) |
| GB (2) | GB1579499A (en, 2012) |
| GR (1) | GR73168B (en, 2012) |
| IE (1) | IE46191B1 (en, 2012) |
| LU (1) | LU78813A1 (en, 2012) |
| NL (1) | NL7800114A (en, 2012) |
| SE (2) | SE436359B (en, 2012) |
| YU (1) | YU44663B (en, 2012) |
| ZA (1) | ZA7827B (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE439308B (sv) * | 1978-08-02 | 1985-06-10 | Roussel Uclaf | Imidazo(1,2-a)kinoxaliner och farmaceutiska kompositioner derav |
| JPS5569567A (en) * | 1978-11-21 | 1980-05-26 | Eisai Co Ltd | Novel imidazole compound, and antidepressant containing the same |
| IT1209431B (it) * | 1980-11-28 | 1989-07-16 | Angeli Inst Spa | Imidazolilfenil amidine, processi per la loro preparazione e loro impiego farmaceutico, ed intermedi di preparazione. |
| DE3830054A1 (de) * | 1988-09-03 | 1990-03-15 | Boehringer Mannheim Gmbh | Phenylamide - verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
| JPH0349309U (en, 2012) * | 1989-09-21 | 1991-05-14 | ||
| US6235740B1 (en) | 1997-08-25 | 2001-05-22 | Bristol-Myers Squibb Co. | Imidazoquinoxaline protein tyrosine kinase inhibitors |
| US6635626B1 (en) | 1997-08-25 | 2003-10-21 | Bristol-Myers Squibb Co. | Imidazoquinoxaline protein tyrosine kinase inhibitors |
| CN1285834A (zh) | 1997-11-11 | 2001-02-28 | 小野药品工业株式会社 | 稠合吡嗪化合物 |
| ES2324846T3 (es) * | 1998-03-04 | 2009-08-17 | Bristol-Myers Squibb Company | Inhibidores de la proteina tirosina quinasa de imidazopirazina heterociclo-sustituida. |
| US6869956B2 (en) * | 2000-10-03 | 2005-03-22 | Bristol-Myers Squibb Company | Methods of treating inflammatory and immune diseases using inhibitors of IκB kinase (IKK) |
| EP1325009B1 (en) | 2000-10-03 | 2006-03-08 | Bristol-Myers Squibb Company | Amino-substituted tetracyclic compounds useful as anti-inflammatory agents and pharmaceutical compositions comprising same |
| CA2436770A1 (en) * | 2001-02-01 | 2002-08-08 | James R. Burke | Methods of treating inflammatory and immune diseases using inhibitors of ikb kinase (ikk) |
| WO2008039794A1 (en) * | 2006-09-25 | 2008-04-03 | Arete Therapeutics, Inc. | Soluble epoxide hydrolase inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3541109A (en) * | 1968-06-25 | 1970-11-17 | Du Pont | 1-substituted imidazoles useful in acth reserve assay |
| US4011236A (en) * | 1968-09-09 | 1977-03-08 | Merck & Co., Inc. | N-(benzimidazol-2-yl)arylcarboxamides as ultraviolet (uv) light absorbers |
| GB1347493A (en) * | 1971-02-11 | 1974-02-27 | Aspro Nicholas Ltd | Benzazine derivatives |
| US3994893A (en) | 1975-11-03 | 1976-11-30 | E. R. Squibb & Sons, Inc. | 4-Amino derivatives of pyrozolo[1,5-a]quinoxaline-3-carboxylic acid and esters |
-
1977
- 1977-12-08 US US05/858,515 patent/US4160097A/en not_active Expired - Lifetime
- 1977-12-23 GR GR55051A patent/GR73168B/el unknown
- 1977-12-28 JP JP15758177A patent/JPS5387398A/ja active Granted
- 1977-12-28 CA CA000293972A patent/CA1149385A/en not_active Expired
-
1978
- 1978-01-03 BE BE184085A patent/BE862608A/xx not_active IP Right Cessation
- 1978-01-04 DK DK004278A patent/DK157024C/da not_active IP Right Cessation
- 1978-01-04 NL NL7800114A patent/NL7800114A/xx not_active Application Discontinuation
- 1978-01-04 FI FI780023A patent/FI64374C/fi not_active IP Right Cessation
- 1978-01-04 ZA ZA00780027A patent/ZA7827B/xx unknown
- 1978-01-05 DE DE19782800480 patent/DE2800480A1/de active Granted
- 1978-01-05 SE SE7800138A patent/SE436359B/sv not_active IP Right Cessation
- 1978-01-05 LU LU78813A patent/LU78813A1/xx unknown
- 1978-01-05 DE DE2858766A patent/DE2858766C2/de not_active Expired - Fee Related
- 1978-01-06 CH CH15278A patent/CH636102A5/fr not_active IP Right Cessation
- 1978-01-06 YU YU21/78A patent/YU44663B/xx unknown
- 1978-01-06 GB GB13335/79A patent/GB1579499A/en not_active Expired
- 1978-01-06 GB GB492/78A patent/GB1579498A/en not_active Expired
- 1978-01-06 IE IE37/78A patent/IE46191B1/en unknown
- 1978-01-06 FR FR7800308A patent/FR2376858A1/fr active Granted
- 1978-01-09 CS CS78169A patent/CS200232B2/cs unknown
- 1978-01-11 AU AU32331/78A patent/AU521807B2/en not_active Expired
-
1983
- 1983-01-18 CH CH27483A patent/CH640229A5/fr not_active IP Right Cessation
- 1983-02-21 SE SE8300945A patent/SE460477B/sv not_active IP Right Cessation
-
1986
- 1986-01-17 JP JP61006590A patent/JPS61171470A/ja active Granted
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