LU82753A1 - 1-oxydes et 1,1-dioxydes de 1,2,5-thiadiazoles 3,4-disubstitues - Google Patents
1-oxydes et 1,1-dioxydes de 1,2,5-thiadiazoles 3,4-disubstitues Download PDFInfo
- Publication number
- LU82753A1 LU82753A1 LU82753A LU82753A LU82753A1 LU 82753 A1 LU82753 A1 LU 82753A1 LU 82753 A LU82753 A LU 82753A LU 82753 A LU82753 A LU 82753A LU 82753 A1 LU82753 A1 LU 82753A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- radical
- alkyl
- amino
- thiadiazole
- represent
- Prior art date
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- WNSDZBQLMGKPQS-UHFFFAOYSA-N hydron;piperazine-2-carboxylic acid;dichloride Chemical compound Cl.Cl.OC(=O)C1CNCCN1 WNSDZBQLMGKPQS-UHFFFAOYSA-N 0.000 title 1
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 210
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 49
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 36
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 19
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- 125000002541 furyl group Chemical group 0.000 claims abstract description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 15
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 15
- 239000012453 solvate Substances 0.000 claims abstract description 14
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 14
- 239000011593 sulfur Substances 0.000 claims abstract description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 6
- 125000001786 isothiazolyl group Chemical group 0.000 claims abstract description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims abstract description 5
- 125000001425 triazolyl group Chemical group 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 267
- 150000003254 radicals Chemical class 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 82
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 79
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 73
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 65
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 125000003545 alkoxy group Chemical group 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000000304 alkynyl group Chemical group 0.000 claims description 39
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 36
- 125000003342 alkenyl group Chemical group 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 125000004434 sulfur atom Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 239000000460 chlorine Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 14
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 230000002496 gastric effect Effects 0.000 claims description 10
- 230000028327 secretion Effects 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 239000000470 constituent Substances 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000006308 propyl amino group Chemical group 0.000 claims description 6
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 4
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 3
- AJUZRVYAIZERFL-UHFFFAOYSA-N 2-(1,3-thiazol-2-yl)guanidine Chemical compound NC(N)=NC1=NC=CS1 AJUZRVYAIZERFL-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 230000009977 dual effect Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 11
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract description 6
- 150000001204 N-oxides Chemical class 0.000 abstract description 3
- 239000003699 antiulcer agent Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 645
- 239000000243 solution Substances 0.000 description 223
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 186
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 121
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 102
- 238000002844 melting Methods 0.000 description 92
- 230000008018 melting Effects 0.000 description 92
- 239000000047 product Substances 0.000 description 88
- 238000004458 analytical method Methods 0.000 description 87
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 78
- 239000011541 reaction mixture Substances 0.000 description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 75
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- 239000000741 silica gel Substances 0.000 description 50
- 229910002027 silica gel Inorganic materials 0.000 description 50
- 239000000725 suspension Substances 0.000 description 49
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 48
- 238000001953 recrystallisation Methods 0.000 description 48
- 238000003756 stirring Methods 0.000 description 45
- 238000010828 elution Methods 0.000 description 43
- 239000003921 oil Substances 0.000 description 36
- 229960004592 isopropanol Drugs 0.000 description 35
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- 238000012937 correction Methods 0.000 description 28
- 239000007787 solid Substances 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 238000000354 decomposition reaction Methods 0.000 description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 239000000284 extract Substances 0.000 description 16
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 13
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical class [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 238000003818 flash chromatography Methods 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- XIWSFHMGJRJKJR-UHFFFAOYSA-N 1,2,5-thiadiazol-3-amine Chemical compound NC=1C=NSN=1 XIWSFHMGJRJKJR-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 9
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
- JFGCGQJHMUYGLU-UHFFFAOYSA-N 2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethanamine Chemical compound CN(C)CC1=CC=C(CSCCN)O1 JFGCGQJHMUYGLU-UHFFFAOYSA-N 0.000 description 8
- ZRSLQBDTGLCFJJ-UHFFFAOYSA-N 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide Chemical compound COC1=NS(=O)(=O)N=C1OC ZRSLQBDTGLCFJJ-UHFFFAOYSA-N 0.000 description 8
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000006260 foam Substances 0.000 description 8
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000003760 tallow Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
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- 239000002585 base Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 241000272814 Anser sp. Species 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
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- 239000007858 starting material Substances 0.000 description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- 241001674048 Phthiraptera Species 0.000 description 4
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- 239000004480 active ingredient Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 4
- 229960001380 cimetidine Drugs 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Substances OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
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- 239000002464 receptor antagonist Substances 0.000 description 4
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- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000012501 chromatography medium Substances 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- OKGXJRGLYVRVNE-UHFFFAOYSA-N diaminomethylidenethiourea Chemical compound NC(N)=NC(N)=S OKGXJRGLYVRVNE-UHFFFAOYSA-N 0.000 description 1
- 125000002720 diazolyl group Chemical group 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- MBMJDELICBDLEE-UHFFFAOYSA-N ethanamine;dihydrochloride Chemical compound Cl.Cl.CCN MBMJDELICBDLEE-UHFFFAOYSA-N 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- QBESCMSODIVAQG-UHFFFAOYSA-N ethaneperoxoic acid;lead Chemical compound [Pb].CC(=O)OO QBESCMSODIVAQG-UHFFFAOYSA-N 0.000 description 1
- DWXKSCKBUSAOKS-UHFFFAOYSA-N ethyl 2-chloro-3-oxopropanoate Chemical compound CCOC(=O)C(Cl)C=O DWXKSCKBUSAOKS-UHFFFAOYSA-N 0.000 description 1
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- XHYIOUXLDLVTNF-UHFFFAOYSA-N ethyl n-(2-amino-2-sulfanylideneethyl)-n-methylcarbamate Chemical compound CCOC(=O)N(C)CC(N)=S XHYIOUXLDLVTNF-UHFFFAOYSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940057952 methanol Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- WHZFDYQSENAPEV-UHFFFAOYSA-N n,n-dimethyl-1,3-thiazol-2-amine Chemical compound CN(C)C1=NC=CS1 WHZFDYQSENAPEV-UHFFFAOYSA-N 0.000 description 1
- YHHPQMAEWZGPRQ-UHFFFAOYSA-N n,n-dimethyl-1-(3-methylfuran-2-yl)methanamine Chemical compound CN(C)CC=1OC=CC=1C YHHPQMAEWZGPRQ-UHFFFAOYSA-N 0.000 description 1
- YHSGBTCBISTXFJ-UHFFFAOYSA-N n-[3-(piperidin-1-ylmethyl)phenoxy]propan-1-amine Chemical compound CCCNOC1=CC=CC(CN2CCCCC2)=C1 YHSGBTCBISTXFJ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VXKMYUBIXHMMTB-UHFFFAOYSA-N n-methyl-1,2,5-thiadiazol-3-amine Chemical compound CNC=1C=NSN=1 VXKMYUBIXHMMTB-UHFFFAOYSA-N 0.000 description 1
- DWVCPSQPTSNMRX-UHFFFAOYSA-N n-methyl-1,3-thiazol-2-amine Chemical compound CNC1=NC=CS1 DWVCPSQPTSNMRX-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- KJZSZWAHZOOOGC-UHFFFAOYSA-N phenyl n-(2-amino-2-sulfanylideneethyl)-n-methylcarbamate Chemical compound NC(=S)CN(C)C(=O)OC1=CC=CC=C1 KJZSZWAHZOOOGC-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Lubricants (AREA)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US7251779A | 1979-09-04 | 1979-09-04 | |
US7251779 | 1979-09-04 | ||
US11718280A | 1980-01-31 | 1980-01-31 | |
US11718280 | 1980-01-31 | ||
US16383180 | 1980-06-07 | ||
US16383180A | 1980-07-07 | 1980-07-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
LU82753A1 true LU82753A1 (fr) | 1981-04-17 |
Family
ID=27372107
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LU82753A LU82753A1 (fr) | 1979-09-04 | 1980-09-04 | 1-oxydes et 1,1-dioxydes de 1,2,5-thiadiazoles 3,4-disubstitues |
Country Status (23)
Country | Link |
---|---|
US (1) | US4374248A (cs) |
AR (1) | AR240559A1 (cs) |
AT (2) | AT376978B (cs) |
CA (4) | CA1167841A (cs) |
CH (2) | CH649764A5 (cs) |
CS (1) | CS235951B2 (cs) |
CY (2) | CY1360A (cs) |
DE (2) | DE3051146C2 (cs) |
DK (4) | DK160611C (cs) |
FI (1) | FI76795C (cs) |
GB (2) | GB2067987B (cs) |
HK (2) | HK41387A (cs) |
IE (2) | IE51235B1 (cs) |
KE (2) | KE3685A (cs) |
LU (1) | LU82753A1 (cs) |
MY (2) | MY8700585A (cs) |
NL (3) | NL189197C (cs) |
NO (4) | NO160003C (cs) |
NZ (1) | NZ194831A (cs) |
PT (1) | PT71764B (cs) |
SE (5) | SE449099B (cs) |
SG (1) | SG61187G (cs) |
ZW (1) | ZW20580A1 (cs) |
Families Citing this family (51)
Publication number | Priority date | Publication date | Assignee | Title |
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ZW7683A1 (en) * | 1982-03-29 | 1984-01-04 | Bristol Myers Co | Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine h2 receptor antagonist activity |
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US4528377A (en) * | 1982-03-29 | 1985-07-09 | Bristol-Myers Company | Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity |
FI832519L (fi) * | 1982-07-12 | 1984-01-13 | Bristol Myers Co | Farmaceutiska foerfaranden och sammansaettningar |
US4520025A (en) * | 1982-07-21 | 1985-05-28 | William H. Rorer, Inc. | Bicyclic nitrogen heterocyclic ethers and thioethers, and their pharmaceutical uses |
EP0105732A3 (en) * | 1982-10-01 | 1985-09-04 | Beecham Group Plc | Histamine h2 receptor antagonists of the benzisothiazole amino and benzthiadiazine amino series |
US4461900A (en) * | 1983-03-14 | 1984-07-24 | American Home Products Corporation | 4,5-Dihydrothiadiazole 1,1-dioxide derivatives |
AT387384B (de) * | 1983-03-16 | 1989-01-10 | Bristol Myers Co | Verfahren zur herstellung von thiadiazolderivaten |
US4440933A (en) * | 1983-03-16 | 1984-04-03 | Bristol-Myers Company | Process for preparing 1,2,5-thiadiazoles |
EP0123741A1 (en) * | 1983-04-26 | 1984-11-07 | Shionogi & Co., Ltd. | 2-Guanidino-4-hydroxymethylthiazole and derivatives thereof |
US4543352A (en) * | 1983-04-29 | 1985-09-24 | William H. Rorer, Inc. | Naphthalene aminoalkylene ethers and thioethers, and their pharmaceutical uses |
DE3326545A1 (de) * | 1983-07-22 | 1985-01-31 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | Propan-2-ol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
US4529731A (en) * | 1983-09-22 | 1985-07-16 | American Home Products Corporation | Thiadiazolediamine derivative with histamine H-2 receptor inhibiting properties |
US4644006A (en) * | 1984-06-22 | 1987-02-17 | Bristol-Myers Company | Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity |
US4692531A (en) * | 1984-06-22 | 1987-09-08 | Bristol-Myers Company | Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity |
US4612309A (en) * | 1984-10-23 | 1986-09-16 | William H. Rorer, Inc. | Antisecretory bicyclic benzo-oxy heterocyclic ethers and thioethers |
GB8501535D0 (en) * | 1985-01-22 | 1985-02-20 | Smith Kline French Lab | Chemical compounds |
US4728648A (en) * | 1985-02-09 | 1988-03-01 | Smith Kline & French Laboratories Limited | Histamine antagonist triadiazole derivatives, compositions, and method of use therefor |
GB8509276D0 (en) * | 1985-04-11 | 1985-05-15 | Smith Kline French Lab | Pyridine derivatives |
GB8510680D0 (en) * | 1985-04-26 | 1985-06-05 | Smith Kline French Lab | Pyridine derivatives |
CA1286297C (en) * | 1985-06-13 | 1991-07-16 | George S. Sach | Pyridine derivatives |
DE3532880A1 (de) * | 1985-09-14 | 1987-03-26 | Basf Ag | 1,4-disubstituierte pyrazolderivate |
GB8610867D0 (en) * | 1986-05-02 | 1986-06-11 | Smith Kline French Lab | 3-hydroxypyridines |
ES2008962A6 (es) * | 1987-12-17 | 1989-08-16 | Marga Investigacion | Proceso para la preparacion de nuevos compuestos de 2-guanidinotiazol |
ATE197296T1 (de) * | 1991-05-21 | 2000-11-15 | Lilly Co Eli | Verfahren zur herstellung von zwischenprodukten für nizatidine und verwandte verbindungen |
US5248673A (en) * | 1992-12-23 | 1993-09-28 | Bristol-Myers Squibb Co. | Bisamidine derivatives as thrombin inhibitors |
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US5618816A (en) * | 1995-03-02 | 1997-04-08 | Bristol-Myers Squibb Company | Antimigraine 1,2,5-thiadiazole derivatives of indolylalkyl-pyridnyl and pyrimidinylpiperazines |
US5767280A (en) * | 1995-06-01 | 1998-06-16 | Eli Lilly And Company | Process for making heterocyclic compounds |
DE60326080D1 (en) | 2002-10-09 | 2009-03-19 | Schering Corp | Thiadiazoldioxide und thiadiazoloxide als cxc- und cc-chemokinrezeptor liganden |
EP1694659B8 (en) | 2003-12-19 | 2008-10-08 | Schering Corporation | Thiadiazoles as cxc- and cc- chemokine receptor ligands |
EP1697354B1 (en) | 2003-12-22 | 2013-08-07 | Merck Sharp & Dohme Corp. | Isothiazole dioxides as cxc- and cc- chemokine receptor ligands |
WO2007002764A2 (en) | 2005-06-29 | 2007-01-04 | Schering Corporation | Di-substituted oxadiazoles as cxc-chemokine receptor ligands |
EP1907399B1 (en) | 2005-06-29 | 2010-10-27 | Schering Corporation | 5,6-di-substituted oxadiazolopyrazines and thiadiazolopyrazines as cxc-chemokine receptor ligands |
US9505728B2 (en) | 2012-03-09 | 2016-11-29 | Inception 2, Inc. | Triazolone compounds and uses thereof |
WO2014009293A1 (en) | 2012-07-13 | 2014-01-16 | Basf Se | New substituted thiadiazoles and their use as fungicides |
BR112015013350B1 (pt) | 2012-12-20 | 2022-04-05 | Tempest Therapeutics, Inc | Composto ou sal farmaceuticamente aceitável do mesmo, composição farmacêutica e respectivos usos |
KR20160048988A (ko) | 2013-09-06 | 2016-05-04 | 인셉션 2 인코퍼레이티드 | 트라이아졸론 화합물 및 이의 용도 |
CN105061360B (zh) * | 2015-07-28 | 2018-06-19 | 首都师范大学 | 一种3,4-二氨基-1,2,5-噻二唑的提纯方法 |
US20230349922A1 (en) | 2020-08-11 | 2023-11-02 | Université De Strasbourg | H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer |
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IL22850A (en) * | 1964-03-18 | 1968-12-26 | Merck & Co Inc | 3-chloro-1,2,5-thiazdiazole-4-carboxylic acid being an intermediate in the preparation of sulfa drugs |
CH482712A (de) * | 1964-10-01 | 1969-12-15 | Merck & Co Inc | Verfahren zur Herstellung von 3-Amino-1,2,5-thiadiazolen |
US3564000A (en) * | 1965-10-15 | 1971-02-16 | Merck & Co Inc | Process for preparing 3-chloro-4-hydroxy-1,2,5-thiadiazole derivatives |
US3419573A (en) * | 1965-10-15 | 1968-12-31 | Merck & Co Inc | 3-chloro-4-oxy-1,2,5-thiadiazoles, and a process for preparing same |
DE1770152A1 (de) * | 1968-04-08 | 1971-09-30 | Lentia Gmbh | Verfahren zur Herstellung von 3-Amino-4-brom-1,2,5-thiadiazol |
US3657237A (en) * | 1968-05-22 | 1972-04-18 | Frosst & Co Charles E | Process for making 1 2 5-thiadiazoles in the sinister configuration |
US4104381A (en) * | 1973-05-03 | 1978-08-01 | Smith Kline & French Laboratories Limited | Pharmacologically active compounds |
AT348517B (de) * | 1977-01-19 | 1979-02-26 | Chemie Linz Ag | Verfahren zur herstellung von reinem 3-methoxy- 4- (4'-aminobenzolsulfonamido) -1,2,5-thiadiazol |
US4165378A (en) * | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
ZA782129B (en) * | 1977-04-20 | 1979-03-28 | Ici Ltd | Hertocyclic derivatives |
US4374836A (en) * | 1978-10-16 | 1983-02-22 | Imperial Chemical Industries Ltd. | Antisecretory heterocyclic derivatives, process for their manufacture and pharmaceutical compositions containing them |
DE3175201D1 (en) * | 1980-04-30 | 1986-10-02 | Merck & Co Inc | Aminothiadiazoles as gastric secretion inhibitors |
EP0045155B1 (en) * | 1980-07-30 | 1985-01-02 | Imperial Chemical Industries Plc | Guanidine derivatives |
EP0073971B1 (en) * | 1981-08-24 | 1986-05-21 | Merck & Co. Inc. | Thiadiazole oxides as gastric antisecretory agents |
-
1980
- 1980-09-01 FI FI802740A patent/FI76795C/fi not_active IP Right Cessation
- 1980-09-01 DK DK371880A patent/DK160611C/da not_active IP Right Cessation
- 1980-09-01 NL NLAANVRAGE8004967,A patent/NL189197C/xx not_active IP Right Cessation
- 1980-09-02 GB GB8028326A patent/GB2067987B/en not_active Expired
- 1980-09-02 NO NO80802576A patent/NO160003C/no unknown
- 1980-09-02 CY CY136080A patent/CY1360A/xx unknown
- 1980-09-03 IE IE1175/86A patent/IE51235B1/en not_active IP Right Cessation
- 1980-09-03 CA CA000359493A patent/CA1167841A/en not_active Expired
- 1980-09-03 DE DE3051146A patent/DE3051146C2/de not_active Expired - Fee Related
- 1980-09-03 AT AT0443480A patent/AT376978B/de active
- 1980-09-03 IE IE1851/80A patent/IE50997B1/en not_active IP Right Cessation
- 1980-09-03 NZ NZ194831A patent/NZ194831A/en unknown
- 1980-09-03 DE DE3033169A patent/DE3033169C2/de not_active Expired
- 1980-09-03 SE SE8006148A patent/SE449099B/sv not_active IP Right Cessation
- 1980-09-03 PT PT71764A patent/PT71764B/pt not_active IP Right Cessation
- 1980-09-04 CH CH6659/80A patent/CH649764A5/de not_active IP Right Cessation
- 1980-09-04 CH CH1760/85A patent/CH658055A5/de not_active IP Right Cessation
- 1980-09-04 ZW ZW205/80A patent/ZW20580A1/xx unknown
- 1980-09-04 CS CS816979A patent/CS235951B2/cs unknown
- 1980-09-04 LU LU82753A patent/LU82753A1/fr unknown
-
1981
- 1981-06-23 US US06/276,586 patent/US4374248A/en not_active Expired - Lifetime
-
1982
- 1982-11-02 CA CA000579079A patent/CA1263114A/en not_active Expired
- 1982-11-02 CA CA000579080A patent/CA1263115A/en not_active Expired
- 1982-11-02 CA CA000431960A patent/CA1248962A/en not_active Expired
-
1983
- 1983-07-13 GB GB08318949A patent/GB2132190B/en not_active Expired
- 1983-07-13 CY CY140283A patent/CY1402A/xx unknown
- 1983-11-29 AR AR29495183A patent/AR240559A1/es active
-
1984
- 1984-02-27 AT AT0064584A patent/AT377257B/de not_active IP Right Cessation
- 1984-06-08 SE SE8403107A patent/SE456580B/sv not_active IP Right Cessation
- 1984-06-08 SE SE8403109A patent/SE456581B/sv not_active IP Right Cessation
- 1984-06-08 SE SE8403111A patent/SE461733B/sv not_active IP Right Cessation
- 1984-06-08 SE SE8403108A patent/SE456582B/sv not_active IP Right Cessation
-
1986
- 1986-06-23 NO NO86862501A patent/NO162664C/no unknown
- 1986-12-23 KE KE3685A patent/KE3685A/xx unknown
-
1987
- 1987-04-06 NO NO87871421A patent/NO160781C/no unknown
- 1987-04-06 NO NO87871420A patent/NO161737C/no unknown
- 1987-05-28 HK HK413/87A patent/HK41387A/xx unknown
- 1987-07-20 KE KE3742A patent/KE3742A/xx unknown
- 1987-07-28 SG SG611/87A patent/SG61187G/en unknown
- 1987-12-03 HK HK891/87A patent/HK89187A/xx unknown
- 1987-12-31 MY MY1987585A patent/MY8700585A/xx unknown
- 1987-12-31 MY MY1987735A patent/MY8700735A/xx unknown
-
1990
- 1990-11-09 DK DK269190A patent/DK164702C/da not_active IP Right Cessation
- 1990-11-09 DK DK269090A patent/DK164700C/da not_active IP Right Cessation
- 1990-11-09 DK DK268990A patent/DK164363C/da not_active IP Right Cessation
-
1992
- 1992-07-09 NL NL9201237A patent/NL9201237A/nl not_active Application Discontinuation
- 1992-07-09 NL NL9201236A patent/NL9201236A/nl not_active Application Discontinuation
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