DD245870A5 - Verfahren zur herstellung von triazoyl-chinolin-derivate - Google Patents
Verfahren zur herstellung von triazoyl-chinolin-derivate Download PDFInfo
- Publication number
- DD245870A5 DD245870A5 DD86290329A DD29032986A DD245870A5 DD 245870 A5 DD245870 A5 DD 245870A5 DD 86290329 A DD86290329 A DD 86290329A DD 29032986 A DD29032986 A DD 29032986A DD 245870 A5 DD245870 A5 DD 245870A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- triazole
- compounds
- hydrogen
- defined above
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 238000000034 method Methods 0.000 claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 14
- -1 C 1-4 -alkoxy Chemical group 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims abstract 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 19
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 claims description 8
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 claims description 5
- 150000005653 4-chloroquinolines Chemical class 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 5
- 150000005642 2-chloroquinolines Chemical class 0.000 claims description 4
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000005634 haloquinolines Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 abstract description 7
- 230000000202 analgesic effect Effects 0.000 abstract description 4
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 230000001532 anti-fungicidal effect Effects 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- 239000000203 mixture Substances 0.000 description 28
- 239000000047 product Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 16
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 208000025865 Ulcer Diseases 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 5
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 5
- 229960002009 naproxen Drugs 0.000 description 5
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 231100000397 ulcer Toxicity 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000002683 foot Anatomy 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 229960002895 phenylbutazone Drugs 0.000 description 4
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 4
- 239000003495 polar organic solvent Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- 241000700157 Rattus norvegicus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- UMYPPRQNLXTIEQ-UHFFFAOYSA-N 2-chloro-3-methylquinoline Chemical compound C1=CC=C2N=C(Cl)C(C)=CC2=C1 UMYPPRQNLXTIEQ-UHFFFAOYSA-N 0.000 description 2
- PFEIMKNQOIFKSW-UHFFFAOYSA-N 2-chloro-4-methylquinoline Chemical compound C1=CC=C2C(C)=CC(Cl)=NC2=C1 PFEIMKNQOIFKSW-UHFFFAOYSA-N 0.000 description 2
- ILOAZUIOTZZIBK-UHFFFAOYSA-N 4-chloro-2,8-dimethylquinoline Chemical compound C1=CC=C(C)C2=NC(C)=CC(Cl)=C21 ILOAZUIOTZZIBK-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 208000009386 Experimental Arthritis Diseases 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical group 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- IRUZMQBGFICXJN-UHFFFAOYSA-N 2,7-dichloro-3,8-dimethylquinoline Chemical compound C1=C(Cl)C(C)=C2N=C(Cl)C(C)=CC2=C1 IRUZMQBGFICXJN-UHFFFAOYSA-N 0.000 description 1
- KDALPMWDWKNYDD-UHFFFAOYSA-N 2,8-dimethyl-4-(1,2,4-triazol-1-yl)quinoline Chemical compound C=12C=CC=C(C)C2=NC(C)=CC=1N1C=NC=N1 KDALPMWDWKNYDD-UHFFFAOYSA-N 0.000 description 1
- WUIZKJXDGUIYDV-UHFFFAOYSA-N 2-(3-methyl-1,2,4-triazol-1-yl)-4,6-bis(trichloromethyl)quinoline Chemical compound N1=C(C)N=CN1C1=CC(C(Cl)(Cl)Cl)=C(C=C(C=C2)C(Cl)(Cl)Cl)C2=N1 WUIZKJXDGUIYDV-UHFFFAOYSA-N 0.000 description 1
- NVTHPPOUFJQHDY-UHFFFAOYSA-N 2-chloro-3,8-dimethylquinoline Chemical compound C1=CC(C)=C2N=C(Cl)C(C)=CC2=C1 NVTHPPOUFJQHDY-UHFFFAOYSA-N 0.000 description 1
- UAKXMKQZURGJKF-UHFFFAOYSA-N 2-chloro-4,8-dimethylquinoline Chemical compound C1=C(Cl)N=C2C(C)=CC=CC2=C1C UAKXMKQZURGJKF-UHFFFAOYSA-N 0.000 description 1
- NKFVTTOTYDMEQE-UHFFFAOYSA-N 3-methyl-2-(1,2,4-triazol-1-yl)quinoline Chemical compound CC1=CC2=CC=CC=C2N=C1N1C=NC=N1 NKFVTTOTYDMEQE-UHFFFAOYSA-N 0.000 description 1
- CPOIUXDRGLGBNU-UHFFFAOYSA-N 4,5-dichloro-2,8-dimethylquinoline Chemical compound ClC1=CC=C(C)C2=NC(C)=CC(Cl)=C21 CPOIUXDRGLGBNU-UHFFFAOYSA-N 0.000 description 1
- YWSNYNKOWMWXRR-UHFFFAOYSA-N 4,7,8-trichloro-2-methylquinoline Chemical compound C1=CC(Cl)=C(Cl)C2=NC(C)=CC(Cl)=C21 YWSNYNKOWMWXRR-UHFFFAOYSA-N 0.000 description 1
- HXEWMTXDBOQQKO-UHFFFAOYSA-N 4,7-dichloroquinoline Chemical compound ClC1=CC=NC2=CC(Cl)=CC=C21 HXEWMTXDBOQQKO-UHFFFAOYSA-N 0.000 description 1
- SCEUAEHSSGGQNF-UHFFFAOYSA-N 4-(1,2,4-triazol-1-yl)-2,8-bis(trifluoromethyl)quinoline Chemical compound C=12C=CC=C(C(F)(F)F)C2=NC(C(F)(F)F)=CC=1N1C=NC=N1 SCEUAEHSSGGQNF-UHFFFAOYSA-N 0.000 description 1
- ZSQOESPYYNJBCZ-UHFFFAOYSA-N 4-chloro-2,8-bis(trifluoromethyl)quinoline Chemical compound C1=CC=C(C(F)(F)F)C2=NC(C(F)(F)F)=CC(Cl)=C21 ZSQOESPYYNJBCZ-UHFFFAOYSA-N 0.000 description 1
- KNDOFJFSHZCKGT-UHFFFAOYSA-N 4-chloroquinoline Chemical compound C1=CC=C2C(Cl)=CC=NC2=C1 KNDOFJFSHZCKGT-UHFFFAOYSA-N 0.000 description 1
- ROABMIVUTLPILI-UHFFFAOYSA-N 4-methyl-2-(1,2,4-triazol-1-yl)quinoline;hydrochloride Chemical compound Cl.N=1C2=CC=CC=C2C(C)=CC=1N1C=NC=N1 ROABMIVUTLPILI-UHFFFAOYSA-N 0.000 description 1
- BWSWPOJRYCYBRQ-UHFFFAOYSA-N 4h-1,2,4-triazol-4-ium;chloride Chemical compound Cl.C=1N=CNN=1 BWSWPOJRYCYBRQ-UHFFFAOYSA-N 0.000 description 1
- YPNUEANFTWNLSZ-UHFFFAOYSA-N 5-chloro-2,8-dimethyl-4-(1,2,4-triazol-1-yl)quinoline Chemical compound C=12C(Cl)=CC=C(C)C2=NC(C)=CC=1N1C=NC=N1 YPNUEANFTWNLSZ-UHFFFAOYSA-N 0.000 description 1
- PZKFSRWSQOQYNR-UHFFFAOYSA-N 5-methyl-1h-1,2,4-triazole Chemical compound CC1=NC=NN1 PZKFSRWSQOQYNR-UHFFFAOYSA-N 0.000 description 1
- MOOQWHYQSJMYHN-UHFFFAOYSA-N 6,8-dichloro-2-methyl-4-(1,2,4-triazol-1-yl)quinoline Chemical compound C=12C=C(Cl)C=C(Cl)C2=NC(C)=CC=1N1C=NC=N1 MOOQWHYQSJMYHN-UHFFFAOYSA-N 0.000 description 1
- GUMGAJBKSPWSFM-UHFFFAOYSA-N 6-methoxy-2-methyl-4-(1,2,4-triazol-1-yl)quinoline Chemical compound C12=CC(OC)=CC=C2N=C(C)C=C1N1C=NC=N1 GUMGAJBKSPWSFM-UHFFFAOYSA-N 0.000 description 1
- NTDSDMIIPYISTR-UHFFFAOYSA-N 7-chloro-3,8-dimethyl-2-(1,2,4-triazol-1-yl)quinoline Chemical compound CC1=CC2=CC=C(Cl)C(C)=C2N=C1N1C=NC=N1 NTDSDMIIPYISTR-UHFFFAOYSA-N 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 201000002661 Spondylitis Diseases 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229920006184 cellulose methylcellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61502558A JPH068292B2 (ja) | 1985-05-07 | 1986-05-07 | トリアゾリルキノリン誘導体 |
| PCT/HU1986/000026 WO1986006721A1 (en) | 1985-05-07 | 1986-05-07 | Triazolyl quinoline derivatives |
| EP86902891A EP0221947B1 (en) | 1985-05-07 | 1986-05-07 | Triazolyl quinoline derivatives |
| BR8606663A BR8606663A (pt) | 1985-05-07 | 1986-05-07 | Derivados de triazolil-quinolina |
| DD86290329A DD245870A5 (de) | 1985-05-07 | 1986-05-16 | Verfahren zur herstellung von triazoyl-chinolin-derivate |
| FI870028A FI88920C (fi) | 1985-05-07 | 1987-01-05 | Nya triazolylkinolinderivat, foerfarande foer framstaellning av dem och fungicidkompositioner innehaollande dem |
| DK004187A DK170097B1 (da) | 1985-05-07 | 1987-01-06 | Triazolylquinolin-derivater og syreadditionssalte deraf, fremgangsmåde til fremstilling af sådanne forbindelser, farmaceutisk middel og fungicid indeholdende forbindelserne samt fremgangsmåde til bekæmpelse af svampesygdomme hos planter |
| SU874028766A SU1477247A3 (ru) | 1985-05-07 | 1987-01-06 | Способ получени триазолилхинолиновых производных или их солей присоединени кислот |
| BG077953A BG47648A3 (en) | 1985-05-07 | 1987-01-06 | Method for preparing of triazolyl quanolinic compounds |
| US07/219,903 US5104884A (en) | 1985-05-07 | 1988-07-13 | Triazolyl quinoline derivatives |
| FI920693A FI91065C (fi) | 1985-05-07 | 1992-02-18 | Menetelmä uusien terapeuttisesti käyttökelpoisten triatsolyylikinoliinijohdannaisten valmistamiseksi |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU171885A HU197323B (hu) | 1985-05-07 | 1985-05-07 | EL·JÁRÁS l'JJ KINOLIL—TRIAZOL—SZÁRMAZÉKOK előállítására |
| DD86290329A DD245870A5 (de) | 1985-05-07 | 1986-05-16 | Verfahren zur herstellung von triazoyl-chinolin-derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD245870A5 true DD245870A5 (de) | 1987-05-20 |
Family
ID=25748055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86290329A DD245870A5 (de) | 1985-05-07 | 1986-05-16 | Verfahren zur herstellung von triazoyl-chinolin-derivate |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5104884A (da) |
| EP (1) | EP0221947B1 (da) |
| JP (1) | JPH068292B2 (da) |
| BG (1) | BG47648A3 (da) |
| BR (1) | BR8606663A (da) |
| DD (1) | DD245870A5 (da) |
| DK (1) | DK170097B1 (da) |
| SU (1) | SU1477247A3 (da) |
| WO (1) | WO1986006721A1 (da) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9026389D0 (en) * | 1990-12-05 | 1991-01-23 | Merck Sharp & Dohme | Therapeutic agents |
| US5342846A (en) * | 1990-12-05 | 1994-08-30 | Synphar Laboratories, Inc. | 7-substituted-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid compounds and 7-(substituted triazolyl pyrrolidin-1-yl) 4-oxoquinoline-3-carboxylic acid derivatives useful as antibacterial agents |
| DK0610487T3 (da) * | 1992-09-03 | 2000-05-15 | Boehringer Ingelheim Pharma | Nye aminosyrederivater, fremgangsmåde til deres fremstilling og farmaceutiske præparater indeholdende disse forbindelser |
| HUT69718A (en) * | 1993-04-01 | 1995-09-28 | Alkaloida Vegyeszeti Gyar | Pharmaceutical compositions containing triazolil(thio)quinoline derivatives |
| US5369086A (en) * | 1993-04-28 | 1994-11-29 | Zeneca Limited | N-benzotriazoles |
| JPH08143407A (ja) * | 1994-09-21 | 1996-06-04 | Nippon Bayeragrochem Kk | 殺菌性キノリン誘導体 |
| CZ296163B6 (cs) * | 1996-05-20 | 2006-01-11 | Karboxyamidy chinolinu jako inhibitory TNF a inhibitory PDE-IV | |
| NZ507760A (en) | 1998-03-26 | 2002-10-25 | Japan Tobacco Inc | Amide derivatives and nociceptin antagonists |
| US6900226B2 (en) * | 2000-09-06 | 2005-05-31 | Hoffman-La Roche Inc. | Neuropeptide Y antagonists |
| KR100417705B1 (ko) * | 2001-07-24 | 2004-02-11 | 한국화학연구원 | 4-아졸일-2-퀴놀리논 유도체 및 이를 포함하는 살균제조성물 |
| US6787558B2 (en) * | 2001-09-28 | 2004-09-07 | Hoffmann-La Roche Inc. | Quinoline derivatives |
| US20230098872A1 (en) * | 2021-03-26 | 2023-03-30 | Cedilla Therapeutics, Inc. | Tead inhibitors and uses thereof |
| WO2026008511A1 (en) * | 2024-07-02 | 2026-01-08 | Syngenta Crop Protection Ag | Microbiocidal quinoline-amide compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3769411A (en) * | 1968-09-04 | 1973-10-30 | Rohm & Haas | Fungicidal 1,2,4-4h-triazole derivatives |
| NL7112373A (da) * | 1970-09-25 | 1972-03-28 | ||
| GB1570494A (en) * | 1975-11-28 | 1980-07-02 | Ici Ltd | Thienopyrimidine derivatives and their use as pesticides |
| US4659720A (en) * | 1982-12-20 | 1987-04-21 | Merck & Co., Inc. | 5-amino or substituted amino imidazoles useful to treat coccidiosis |
| JPS59128383A (ja) * | 1982-12-29 | 1984-07-24 | Kanebo Ltd | 新規キノリンカルボン酸誘導体および該化合物を有効成分とする抗菌剤 |
| GB8612796D0 (en) * | 1986-05-27 | 1986-07-02 | Fbc Ltd | Fungicides |
-
1986
- 1986-05-07 WO PCT/HU1986/000026 patent/WO1986006721A1/en not_active Ceased
- 1986-05-07 EP EP86902891A patent/EP0221947B1/en not_active Expired - Lifetime
- 1986-05-07 BR BR8606663A patent/BR8606663A/pt not_active IP Right Cessation
- 1986-05-07 JP JP61502558A patent/JPH068292B2/ja not_active Expired - Lifetime
- 1986-05-16 DD DD86290329A patent/DD245870A5/de not_active IP Right Cessation
-
1987
- 1987-01-06 SU SU874028766A patent/SU1477247A3/ru active
- 1987-01-06 BG BG077953A patent/BG47648A3/xx unknown
- 1987-01-06 DK DK004187A patent/DK170097B1/da not_active IP Right Cessation
-
1988
- 1988-07-13 US US07/219,903 patent/US5104884A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0221947B1 (en) | 1990-11-28 |
| SU1477247A3 (ru) | 1989-04-30 |
| BG47648A3 (en) | 1990-08-15 |
| JPS62503030A (ja) | 1987-12-03 |
| DK4187D0 (da) | 1987-01-06 |
| JPH068292B2 (ja) | 1994-02-02 |
| BR8606663A (pt) | 1987-08-11 |
| EP0221947A1 (en) | 1987-05-20 |
| DK170097B1 (da) | 1995-05-22 |
| US5104884A (en) | 1992-04-14 |
| DK4187A (da) | 1987-01-06 |
| WO1986006721A1 (en) | 1986-11-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0000928B1 (de) | Neue Nitroimidazole und diese enthaltende pharmazeutische Präparate sowie deren Herstellung | |
| EP0049355B1 (de) | 7-Amino-1-cyclopropyl-4-oxo-1,4-dihydro-(naphthyridin oder chinolin)-3-carbonsäuren, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| DE3786365T2 (de) | 5H-1,3,4-Thiadiazolo[3,2-a]pyrimidin-5-on-Derivate und diese enthaltende Gartenbau- und landwirtschaftliche Fungizidmittel. | |
| DE69524246T2 (de) | 1,2,3,4-Tetrahydroquinoxalindion Derivate und ihre Verwendung als Glutamat Rezeptor Antagonisten | |
| DE69624437T2 (de) | 4,6-diarylpyrimidin-derivate und deren salze | |
| EP0281902B1 (de) | Bis-naphthalimide, ihre Herstellung und Verwendung | |
| EP2508521A2 (de) | Verfahren zur Herstellung von Aminocrotonylverbindungen | |
| DE2527937A1 (de) | Benzcycloamidderivate und verfahren zu ihrer herstellung sowie pharmazeutische mittel, worin sie enthalten sind | |
| DD245870A5 (de) | Verfahren zur herstellung von triazoyl-chinolin-derivate | |
| CH651300A5 (de) | Heterocyclisch substituierte aminopropennitrile. | |
| DE2454632A1 (de) | Neue 5(6)-substituierte benzimidazol- 2-carbamate und ihre herstellung | |
| DE2250077A1 (de) | Verfahren zur herstellung von benzoxazol- und benzthiazolverbindungen und ihre verwendung zum pflanzenschutz | |
| DE2138031C3 (de) | Verfahren zur Herstellung von 1.2.4-Triazin-5-onen | |
| DE2363348C3 (de) | Substituierte 5 (6)-Phenoxy-benzimidazol-2-carbaminsäuremethylester, deren Herstellung und diese enthaltende Anthelminthika | |
| CH629203A5 (de) | Verfahren zur herstellung von thiazolinylbenzimidazolen. | |
| US4914104A (en) | Imidazo [1,5-a]pyrimidine derivatives and process for their preparation | |
| EP0018360B1 (de) | N-(5-Methoxybentofuran-2-ylcarbonyl)-N'-benzylpiperazin und Verfahren zu dessen Herstellung | |
| DE3618724C2 (de) | N-[3-(Nitro)-chinol-4-yl]-carboxamidinamide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE3877124T2 (de) | Imidazol-derivate, verfahren zu deren herstellung und deren anwendung als alpha-2-adrenoceptor-antagonisten. | |
| DE3216843A1 (de) | Thiomethylpyridin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| CH642668A5 (de) | 2,6-diaminonebularine, verfahren zu deren herstellung und sie enthaltende pharmazeutische praeparate. | |
| EP0533056A2 (de) | Substituierte Aminopropane, Verfahren zu ihrer Herstellung und ihre Verwendung als Antimykutiku | |
| EP0123700A1 (de) | Substituierte Picolinsäuren, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende Arzneimittel | |
| DD259401A5 (de) | Verfahren zur herstellung von 2-alkylbenzimidazol-derivaten | |
| EP0160173A1 (de) | Benzothiazolderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltendes Arzneimittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |