MXPA01000757A - Oxazolo, tiazolo y selenazolo [4,5-c]-quinolina-4-aminas y analagos de las mismas. - Google Patents
Oxazolo, tiazolo y selenazolo [4,5-c]-quinolina-4-aminas y analagos de las mismas.Info
- Publication number
- MXPA01000757A MXPA01000757A MXPA01000757A MXPA01000757A MXPA01000757A MX PA01000757 A MXPA01000757 A MX PA01000757A MX PA01000757 A MXPA01000757 A MX PA01000757A MX PA01000757 A MXPA01000757 A MX PA01000757A MX PA01000757 A MXPA01000757 A MX PA01000757A
- Authority
- MX
- Mexico
- Prior art keywords
- quinolin
- amine
- alkyl
- thiazole
- oxide
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 102000004127 Cytokines Human genes 0.000 claims abstract description 29
- 108090000695 Cytokines Proteins 0.000 claims abstract description 29
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 19
- 230000003612 virological effect Effects 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 201000010099 disease Diseases 0.000 claims abstract description 10
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 232
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 claims description 229
- 229910052739 hydrogen Inorganic materials 0.000 claims description 175
- 229910052799 carbon Inorganic materials 0.000 claims description 157
- 239000000203 mixture Substances 0.000 claims description 95
- CMOIEFFAOUQJPS-UHFFFAOYSA-N 2-propyl-1,3-thiazole Chemical compound CCCC1=NC=CS1 CMOIEFFAOUQJPS-UHFFFAOYSA-N 0.000 claims description 41
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 41
- -1 2-phenyl-1-ethyl Chemical group 0.000 claims description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 35
- VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical compound CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 21
- CGZDWVZMOMDGBN-UHFFFAOYSA-N 2-Ethylthiazole Chemical compound CCC1=NC=CS1 CGZDWVZMOMDGBN-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 239000011593 sulfur Substances 0.000 claims description 18
- QOJMQILDLLFGEE-UHFFFAOYSA-N 2-butyl-1,3-thiazole Chemical compound CCCCC1=NC=CS1 QOJMQILDLLFGEE-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- CMPVUVUNJQERIT-UHFFFAOYSA-N 2-isobutylthiazole Chemical compound CC(C)CC1=NC=CS1 CMPVUVUNJQERIT-UHFFFAOYSA-N 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 12
- ABCSPNANFXDHDU-UHFFFAOYSA-N 2-benzyl-1,3-thiazole Chemical compound C=1C=CC=CC=1CC1=NC=CS1 ABCSPNANFXDHDU-UHFFFAOYSA-N 0.000 claims description 11
- ABSYEGWQFLNILN-UHFFFAOYSA-N 2-butyl-1,3-oxazole Chemical compound CCCCC1=NC=CO1 ABSYEGWQFLNILN-UHFFFAOYSA-N 0.000 claims description 11
- QFYWDJHDOCZKRF-UHFFFAOYSA-N 2-pentyl-1,3-thiazole Chemical compound CCCCCC1=NC=CS1 QFYWDJHDOCZKRF-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- KUVNLQNSAOBXGR-UHFFFAOYSA-N 2-(ethoxymethyl)-1,3-thiazole Chemical compound CCOCC1=NC=CS1 KUVNLQNSAOBXGR-UHFFFAOYSA-N 0.000 claims description 10
- BMPYSUZRFLIYEA-UHFFFAOYSA-N 2-(2-phenylethenyl)-1,3-thiazole Chemical compound N=1C=CSC=1C=CC1=CC=CC=C1 BMPYSUZRFLIYEA-UHFFFAOYSA-N 0.000 claims description 9
- XWYDEOAZVIYBKM-UHFFFAOYSA-N 2-(methoxymethyl)-1,3-thiazole Chemical compound COCC1=NC=CS1 XWYDEOAZVIYBKM-UHFFFAOYSA-N 0.000 claims description 9
- ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 2-methyl-1,3-oxazole Chemical compound CC1=NC=CO1 ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 0.000 claims description 9
- BZFIPFGRXRRZSP-UHFFFAOYSA-N 2-propan-2-yl-1,3-thiazole Chemical compound CC(C)C1=NC=CS1 BZFIPFGRXRRZSP-UHFFFAOYSA-N 0.000 claims description 9
- QPSZFMZMNPAQPH-UHFFFAOYSA-N 2-propyl-1,3-oxazole Chemical compound CCCC1=NC=CO1 QPSZFMZMNPAQPH-UHFFFAOYSA-N 0.000 claims description 9
- 102100040247 Tumor necrosis factor Human genes 0.000 claims description 9
- 230000006698 induction Effects 0.000 claims description 9
- KEWBUOMVBFMGNS-UHFFFAOYSA-N 2-(2-phenylethyl)-1,3-thiazole Chemical compound N=1C=CSC=1CCC1=CC=CC=C1 KEWBUOMVBFMGNS-UHFFFAOYSA-N 0.000 claims description 8
- SUCDHPJUXCCMDN-UHFFFAOYSA-N 2-ethyl-1,3-oxazole Chemical compound CCC1=NC=CO1 SUCDHPJUXCCMDN-UHFFFAOYSA-N 0.000 claims description 8
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 8
- QHHHLHCCVDMOJI-UHFFFAOYSA-N 1,3-thiazol-4-amine Chemical compound NC1=CSC=N1 QHHHLHCCVDMOJI-UHFFFAOYSA-N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 5
- VNIYSXOHLPIAID-UHFFFAOYSA-N quinoline-4,8-diamine Chemical compound C1=CC=C2C(N)=CC=NC2=C1N VNIYSXOHLPIAID-UHFFFAOYSA-N 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- 239000011669 selenium Substances 0.000 claims description 5
- KFAJXZVDBVRZRC-UHFFFAOYSA-N 1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(N)=CC=NC2=C1 KFAJXZVDBVRZRC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 6
- 150000001555 benzenes Chemical group 0.000 claims 3
- GCMNJUJAKQGROZ-UHFFFAOYSA-N 1,2-Dihydroquinolin-2-imine Chemical compound C1=CC=CC2=NC(N)=CC=C21 GCMNJUJAKQGROZ-UHFFFAOYSA-N 0.000 claims 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 abstract description 21
- 108010050904 Interferons Proteins 0.000 abstract description 21
- 229940079322 interferon Drugs 0.000 abstract description 17
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000028993 immune response Effects 0.000 abstract description 6
- 206010028980 Neoplasm Diseases 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 abstract description 5
- 239000002955 immunomodulating agent Substances 0.000 abstract description 4
- 229940121354 immunomodulator Drugs 0.000 abstract description 4
- HLVNSLBJOPUZKV-UHFFFAOYSA-N [1,3]selenazolo[4,5-c]quinolin-4-amine Chemical class NC1=NC2=CC=CC=C2C2=C1N=C[se]2 HLVNSLBJOPUZKV-UHFFFAOYSA-N 0.000 abstract 1
- 230000017074 necrotic cell death Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 370
- 239000011541 reaction mixture Substances 0.000 description 167
- 239000007787 solid Substances 0.000 description 166
- 229910052757 nitrogen Inorganic materials 0.000 description 156
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 148
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 124
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 96
- 239000000243 solution Substances 0.000 description 92
- 238000004458 analytical method Methods 0.000 description 85
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- 239000002244 precipitate Substances 0.000 description 68
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 65
- 238000001914 filtration Methods 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 56
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 48
- 235000019341 magnesium sulphate Nutrition 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- 238000010992 reflux Methods 0.000 description 42
- 239000000725 suspension Substances 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
- 239000000463 material Substances 0.000 description 40
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 38
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 37
- 239000000706 filtrate Substances 0.000 description 34
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- 238000007429 general method Methods 0.000 description 32
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- 238000003756 stirring Methods 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 239000003921 oil Substances 0.000 description 24
- 235000019198 oils Nutrition 0.000 description 24
- GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 23
- 239000012299 nitrogen atmosphere Substances 0.000 description 23
- 150000001204 N-oxides Chemical class 0.000 description 22
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 description 19
- 239000000741 silica gel Substances 0.000 description 19
- 229910002027 silica gel Inorganic materials 0.000 description 19
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 17
- 239000010410 layer Substances 0.000 description 17
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000908 ammonium hydroxide Substances 0.000 description 16
- 239000000284 extract Substances 0.000 description 16
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
- 235000017557 sodium bicarbonate Nutrition 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 229910021529 ammonia Inorganic materials 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 13
- 229960004132 diethyl ether Drugs 0.000 description 13
- 239000012948 isocyanate Substances 0.000 description 13
- 238000004809 thin layer chromatography Methods 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000001408 amides Chemical class 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 12
- 239000006188 syrup Substances 0.000 description 11
- 235000020357 syrup Nutrition 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- 239000003610 charcoal Substances 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 150000002513 isocyanates Chemical class 0.000 description 10
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- 238000004166 bioassay Methods 0.000 description 9
- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 8
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- YJBLTYRYUXKJLE-UHFFFAOYSA-N 3-amino-1h-quinoline-4-thione Chemical compound C1=CC=C2C(=S)C(N)=CNC2=C1 YJBLTYRYUXKJLE-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- NIQNIQVCPKCNQS-UHFFFAOYSA-N 3-amino-1h-quinolin-4-one Chemical compound C1=CC=C2C(=O)C(N)=CNC2=C1 NIQNIQVCPKCNQS-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- GNZIHPAAJVXCAS-UHFFFAOYSA-N quinolin-4-amine;hydrochloride Chemical compound Cl.C1=CC=C2C(N)=CC=NC2=C1 GNZIHPAAJVXCAS-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000000601 blood cell Anatomy 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000004896 high resolution mass spectrometry Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 235000019260 propionic acid Nutrition 0.000 description 5
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- 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]
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D517/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains two hetero rings
- C07D517/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Communicable Diseases (AREA)
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- Immunology (AREA)
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- Physical Education & Sports Medicine (AREA)
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- Hospice & Palliative Care (AREA)
- Tropical Medicine & Parasitology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9434698P | 1998-07-28 | 1998-07-28 | |
| US09/361,544 US6110929A (en) | 1998-07-28 | 1999-07-27 | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
| PCT/US1999/017027 WO2000006577A1 (en) | 1998-07-28 | 1999-07-28 | OXAZOLO, THIAZOLO AND SELENAZOLO [4,5-c]-QUINOLIN-4-AMINES AND ANALOGS THEREOF |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA01000757A true MXPA01000757A (es) | 2002-04-08 |
Family
ID=26788753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA01000757A MXPA01000757A (es) | 1998-07-28 | 1999-07-28 | Oxazolo, tiazolo y selenazolo [4,5-c]-quinolina-4-aminas y analagos de las mismas. |
Country Status (24)
| Country | Link |
|---|---|
| US (9) | US6110929A (https=) |
| EP (1) | EP1100802B1 (https=) |
| JP (1) | JP4662630B2 (https=) |
| KR (1) | KR100696349B1 (https=) |
| CN (1) | CN1147493C (https=) |
| AT (2) | ATE250612T1 (https=) |
| AU (1) | AU748050B2 (https=) |
| BR (1) | BR9912448A (https=) |
| CA (1) | CA2338504C (https=) |
| CZ (1) | CZ291753B6 (https=) |
| DE (2) | DE69911622T2 (https=) |
| DK (1) | DK1100802T3 (https=) |
| ES (2) | ES2203160T3 (https=) |
| HU (1) | HUP0103137A3 (https=) |
| IL (1) | IL140822A0 (https=) |
| MX (1) | MXPA01000757A (https=) |
| NO (1) | NO20010497L (https=) |
| NZ (1) | NZ509420A (https=) |
| PL (1) | PL347590A1 (https=) |
| PT (2) | PT1380587E (https=) |
| RU (1) | RU2244717C2 (https=) |
| SK (1) | SK1402001A3 (https=) |
| TR (1) | TR200100278T2 (https=) |
| WO (1) | WO2000006577A1 (https=) |
Families Citing this family (269)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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- 1999-07-28 AT AT03021166T patent/ATE320435T1/de not_active IP Right Cessation
- 1999-07-28 DK DK99935968T patent/DK1100802T3/da active
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