NL8001361A - Guanidinothiazoolverbindingen, werkwijzen ter bereiding ervan, alsmede farmaceutische preparaten die de guanidinothiazoolverbindingen bevatten. - Google Patents
Guanidinothiazoolverbindingen, werkwijzen ter bereiding ervan, alsmede farmaceutische preparaten die de guanidinothiazoolverbindingen bevatten. Download PDFInfo
- Publication number
- NL8001361A NL8001361A NL8001361A NL8001361A NL8001361A NL 8001361 A NL8001361 A NL 8001361A NL 8001361 A NL8001361 A NL 8001361A NL 8001361 A NL8001361 A NL 8001361A NL 8001361 A NL8001361 A NL 8001361A
- Authority
- NL
- Netherlands
- Prior art keywords
- group
- formula
- carbon atoms
- small number
- compound
- Prior art date
Links
- -1 GUANIDINOTHIAZOLE COMPOUNDS Chemical class 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 33
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- DFHYHFAHYAJKDU-UHFFFAOYSA-N n'-cyano-3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]propanimidamide Chemical compound NC(N)=NC1=NC(CSCCC(N)=NC#N)=CS1 DFHYHFAHYAJKDU-UHFFFAOYSA-N 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- DDFUGJYDTVVFBO-UHFFFAOYSA-N (z)-[1-amino-3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]propylidene]urea Chemical compound NC(N)=NC1=NC(CSCCC(N)=NC(N)=O)=CS1 DDFUGJYDTVVFBO-UHFFFAOYSA-N 0.000 claims 1
- 239000004236 Ponceau SX Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 141
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 74
- 239000000243 solution Substances 0.000 description 71
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
- 239000000203 mixture Substances 0.000 description 60
- 239000002904 solvent Substances 0.000 description 48
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- 238000000921 elemental analysis Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 238000001914 filtration Methods 0.000 description 16
- 238000003756 stirring Methods 0.000 description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 238000001816 cooling Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 230000027119 gastric acid secretion Effects 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- HBAPPYPITGPMPF-UHFFFAOYSA-N methyl 5-[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]pentanimidate Chemical compound COC(=N)CCCCC1=CSC(NC(N)=N)=N1 HBAPPYPITGPMPF-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- GNFWGDKKNWGGJY-UHFFFAOYSA-N propanimidamide Chemical compound CCC(N)=N GNFWGDKKNWGGJY-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- FSKYYRZENXOYAP-UHFFFAOYSA-N 2-[4-(2-cyanoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine Chemical compound NC(=N)NC1=NC(CSCCC#N)=CS1 FSKYYRZENXOYAP-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 239000012264 purified product Substances 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- FHKFQNWWGRESEI-UHFFFAOYSA-N 2-[4-(4-cyanobutyl)-1,3-thiazol-2-yl]guanidine Chemical compound NC(=N)NC1=NC(CCCCC#N)=CS1 FHKFQNWWGRESEI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 230000001078 anti-cholinergic effect Effects 0.000 description 3
- 238000001647 drug administration Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- ZTEHTGMWGUKFNE-UHFFFAOYSA-N methyl 3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]propanimidate Chemical compound COC(=N)CCSCC1=CSC(N=C(N)N)=N1 ZTEHTGMWGUKFNE-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 3
- 210000001187 pylorus Anatomy 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- LIOIEWPUGWMDPT-UHFFFAOYSA-N 1,6-dichlorohexan-2-one Chemical compound ClCCCCC(=O)CCl LIOIEWPUGWMDPT-UHFFFAOYSA-N 0.000 description 2
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 102000000543 Histamine Receptors Human genes 0.000 description 2
- 108010002059 Histamine Receptors Proteins 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- OGEZDRXXLRLJNU-UHFFFAOYSA-N [2-cyanoethylsulfanyl(1,3-thiazol-4-yl)methyl]thiourea Chemical compound N#CCCSC(NC(=S)N)C1=CSC=N1 OGEZDRXXLRLJNU-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 201000006549 dyspepsia Diseases 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000004211 gastric acid Anatomy 0.000 description 2
- 210000004051 gastric juice Anatomy 0.000 description 2
- 208000024798 heartburn Diseases 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- ZJOZQGURSDEMQX-UHFFFAOYSA-N (2-amino-1,3-thiazol-4-yl)methyl carbamimidothioate Chemical compound NC(=N)SCC1=CSC(N)=N1 ZJOZQGURSDEMQX-UHFFFAOYSA-N 0.000 description 1
- SWGZHHCRMZDRSN-BTJKTKAUSA-N (Z)-but-2-enedioic acid 1-phenoxypropan-2-ylhydrazine Chemical compound OC(=O)\C=C/C(O)=O.NNC(C)COC1=CC=CC=C1 SWGZHHCRMZDRSN-BTJKTKAUSA-N 0.000 description 1
- QFUSOYKIDBRREL-NSCUHMNNSA-N (e)-but-2-en-1-amine Chemical compound C\C=C\CN QFUSOYKIDBRREL-NSCUHMNNSA-N 0.000 description 1
- YVHJJBZJOXANIM-UHFFFAOYSA-N (z)-[1-amino-3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]propylidene]urea;dihydrochloride Chemical compound Cl.Cl.NC(=N)NC1=NC(CSCCC(=N)NC(N)=O)=CS1 YVHJJBZJOXANIM-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- NYKBWTIYNMXTOC-UHFFFAOYSA-N 2-(4-pentyl-1,3-thiazol-2-yl)guanidine Chemical compound CCCCCC1=CSC(N=C(N)N)=N1 NYKBWTIYNMXTOC-UHFFFAOYSA-N 0.000 description 1
- NGEJTCZHQLIDMF-UHFFFAOYSA-N 2-[4-(4-chlorobutyl)-1,3-thiazol-2-yl]guanidine Chemical compound NC(=N)NC1=NC(CCCCCl)=CS1 NGEJTCZHQLIDMF-UHFFFAOYSA-N 0.000 description 1
- AOQGICFDBKEGJR-UHFFFAOYSA-N 2-[4-(4-chlorobutyl)-1,3-thiazol-2-yl]guanidine;hydrochloride Chemical compound Cl.NC(=N)NC1=NC(CCCCCl)=CS1 AOQGICFDBKEGJR-UHFFFAOYSA-N 0.000 description 1
- JNAYPRPPXRWGQO-UHFFFAOYSA-N 2-chloropropanenitrile Chemical compound CC(Cl)C#N JNAYPRPPXRWGQO-UHFFFAOYSA-N 0.000 description 1
- AITCACNVHHBAAG-UHFFFAOYSA-N 2-methylsulfanylpropanimidamide;hydrochloride Chemical compound Cl.CSC(C)C(N)=N AITCACNVHHBAAG-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 1
- PRNYOEGYIXYGFB-UHFFFAOYSA-N 3-[(2-amino-1,3-thiazol-4-yl)methylsulfanyl]propanenitrile Chemical compound NC1=NC(CSCCC#N)=CS1 PRNYOEGYIXYGFB-UHFFFAOYSA-N 0.000 description 1
- AOCKQODHRGLCJY-UHFFFAOYSA-N 3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]-N'-prop-2-ynylpropanimidamide Chemical compound C(C#C)NC(CCSCC=1N=C(SC=1)NC(=N)N)=N AOCKQODHRGLCJY-UHFFFAOYSA-N 0.000 description 1
- UAYVSMQUIRERCK-UHFFFAOYSA-N 3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]-n-hydroxypropanamide Chemical compound NC(N)=NC1=NC(CSCCC(=O)NO)=CS1 UAYVSMQUIRERCK-UHFFFAOYSA-N 0.000 description 1
- 101150017816 40 gene Proteins 0.000 description 1
- COOZINGKDXSHQL-UHFFFAOYSA-N 5-[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]-n'-prop-2-ynylpentanimidamide Chemical compound NC(N)=NC1=NC(CCCCC(N)=NCC#C)=CS1 COOZINGKDXSHQL-UHFFFAOYSA-N 0.000 description 1
- ASXCXALZXYORND-UHFFFAOYSA-N 5-[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]-n-methylpentanamide Chemical compound CNC(=O)CCCCC1=CSC(NC(N)=N)=N1 ASXCXALZXYORND-UHFFFAOYSA-N 0.000 description 1
- NFLLKCVHYJRNRH-UHFFFAOYSA-N 8-chloro-1,3-dimethyl-7H-purine-2,6-dione 2-(diphenylmethyl)oxy-N,N-dimethylethanamine Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(Cl)=N2.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 NFLLKCVHYJRNRH-UHFFFAOYSA-N 0.000 description 1
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- NFUBCFKVZMOTED-SPIKMXEPSA-N C(\C=C/C(=O)O)(=O)O.C(\C=C/C(=O)O)(=O)O.C(CCCC)(=N)N Chemical compound C(\C=C/C(=O)O)(=O)O.C(\C=C/C(=O)O)(=O)O.C(CCCC)(=N)N NFUBCFKVZMOTED-SPIKMXEPSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- LNBNICMKLBBRMB-UHFFFAOYSA-N Famotidine acid methyl ester Chemical compound COC(=O)CCSCC1=CSC(NC(N)=N)=N1 LNBNICMKLBBRMB-UHFFFAOYSA-N 0.000 description 1
- 102100021022 Gastrin Human genes 0.000 description 1
- 108010052343 Gastrins Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 108050006617 Interleukin-1 receptor Proteins 0.000 description 1
- 102000019223 Interleukin-1 receptor Human genes 0.000 description 1
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 1
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
- FPBPLBWLMYGIQR-UHFFFAOYSA-N Metiamide Chemical compound CNC(=S)NCCSCC=1N=CNC=1C FPBPLBWLMYGIQR-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- RULCEMDFXABODO-UHFFFAOYSA-N N-[[1-amino-3-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]propylidene]amino]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NNC(CCSCC=1N=C(SC=1)NC(=N)N)=N RULCEMDFXABODO-UHFFFAOYSA-N 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 210000003815 abdominal wall Anatomy 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001411 amidrazones Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 229960002319 barbital Drugs 0.000 description 1
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 1
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- WDJQAYUPVJEQJW-UHFFFAOYSA-N chloroform;n,n-diethylethanamine;methanol Chemical compound OC.ClC(Cl)Cl.CCN(CC)CC WDJQAYUPVJEQJW-UHFFFAOYSA-N 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- NQXSIMCIJSTZQB-UHFFFAOYSA-N cyanamide;urea Chemical compound NC#N.NC(N)=O NQXSIMCIJSTZQB-UHFFFAOYSA-N 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- OKGXJRGLYVRVNE-UHFFFAOYSA-N diaminomethylidenethiourea Chemical compound NC(N)=NC(N)=S OKGXJRGLYVRVNE-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
- IENVYYDJUAUCRS-UHFFFAOYSA-N ethyl 5-[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]pentanimidate Chemical compound CCOC(=N)CCCCC1=CSC(NC(N)=N)=N1 IENVYYDJUAUCRS-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- XUFQPHANEAPEMJ-UHFFFAOYSA-N famotidine Chemical compound NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1 XUFQPHANEAPEMJ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 210000003736 gastrointestinal content Anatomy 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 239000000938 histamine H1 antagonist Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
- 229960000582 mepyramine Drugs 0.000 description 1
- NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 1
- 229960002329 methacholine Drugs 0.000 description 1
- AALPPSRGMZDWBX-UHFFFAOYSA-N methyl 3-[[(n'-methylcarbamimidoyl)amino]-(1,3-thiazol-4-yl)methyl]sulfanylpropanimidate Chemical compound COC(=N)CCSC(NC(N)=NC)C1=CSC=N1 AALPPSRGMZDWBX-UHFFFAOYSA-N 0.000 description 1
- WSDUOQZGIBCGON-UHFFFAOYSA-N methyl propanimidothioate Chemical compound CCC(=N)SC WSDUOQZGIBCGON-UHFFFAOYSA-N 0.000 description 1
- 229950003251 metiamide Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- FSBLQQPYVMVSEN-UHFFFAOYSA-N n'-cyano-3-[[(n'-methylcarbamimidoyl)amino]-(1,3-thiazol-4-yl)methyl]sulfanylpropanimidamide Chemical compound N#CNC(=N)CCSC(NC(N)=NC)C1=CSC=N1 FSBLQQPYVMVSEN-UHFFFAOYSA-N 0.000 description 1
- OTONQHQAXUYNSI-UHFFFAOYSA-N n'-cyano-5-[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]pentanimidamide Chemical compound NC(=N)NC1=NC(CCCCC(=N)NC#N)=CS1 OTONQHQAXUYNSI-UHFFFAOYSA-N 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- NFVFJORFTLHBCY-UHFFFAOYSA-N n-[[4-(2-cyanoethylsulfanylmethyl)-1,3-thiazol-2-yl]carbamothioyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(=S)NC1=NC(CSCCC#N)=CS1 NFVFJORFTLHBCY-UHFFFAOYSA-N 0.000 description 1
- JRWICMWBCXNHQK-UHFFFAOYSA-N n-[n-acetyl-c-[2-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]ethyl]carbonimidoyl]acetamide Chemical compound CC(=O)NC(=NC(C)=O)CCSCC1=CSC(NC(N)=N)=N1 JRWICMWBCXNHQK-UHFFFAOYSA-N 0.000 description 1
- PPKKOTLGXBHLAB-XVHSACDVSA-N nocii Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(O)=O)C(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCSC)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1C=CC=CC=1)C1=CC=C(O)C=C1 PPKKOTLGXBHLAB-XVHSACDVSA-N 0.000 description 1
- WCVVIGQKJZLJDB-UHFFFAOYSA-N o-butylhydroxylamine Chemical compound CCCCON WCVVIGQKJZLJDB-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- DHGXIXIPKCFMNO-UHFFFAOYSA-N pent-1-yn-1-amine Chemical compound CCCC#CN DHGXIXIPKCFMNO-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- VHWJSJBTUWUEAL-UHFFFAOYSA-N propanamide;hydrochloride Chemical compound Cl.CCC(N)=O VHWJSJBTUWUEAL-UHFFFAOYSA-N 0.000 description 1
- WFMVWGHNHRXONA-UHFFFAOYSA-N propanenitrile hydroiodide Chemical compound I.C(CC)#N WFMVWGHNHRXONA-UHFFFAOYSA-N 0.000 description 1
- UQNCOOZDFCLMGG-UHFFFAOYSA-N propanimidamide;dihydrochloride Chemical compound Cl.Cl.CCC(N)=N UQNCOOZDFCLMGG-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000002731 stomach secretion inhibitor Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000691 up-and-down procedure Toxicity 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2574579A JPS55118476A (en) | 1979-03-06 | 1979-03-06 | Novel amidine derivative and its preparation |
JP2574579 | 1979-03-06 | ||
JP7950879A JPS565469A (en) | 1979-06-23 | 1979-06-23 | Novel amidine derivative and its preparation |
JP7950879 | 1979-06-23 | ||
KR800000932 | 1980-03-06 | ||
KR1019800000932A KR830002478B1 (ko) | 1979-03-06 | 1980-03-06 | 구아니디노 티아졸 화합물의 제조방법 |
Publications (1)
Publication Number | Publication Date |
---|---|
NL8001361A true NL8001361A (nl) | 1980-09-09 |
Family
ID=27285138
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NL8001361A NL8001361A (nl) | 1979-03-06 | 1980-03-06 | Guanidinothiazoolverbindingen, werkwijzen ter bereiding ervan, alsmede farmaceutische preparaten die de guanidinothiazoolverbindingen bevatten. |
Country Status (11)
Country | Link |
---|---|
US (1) | US4362736A (da) |
CA (1) | CA1145345A (da) |
CH (1) | CH644114A5 (da) |
DE (1) | DE3008056A1 (da) |
ES (1) | ES8103070A1 (da) |
FR (1) | FR2450827A1 (da) |
GB (1) | GB2052478B (da) |
IT (1) | IT1165509B (da) |
NL (1) | NL8001361A (da) |
PH (1) | PH16099A (da) |
SE (1) | SE447253B (da) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ196923A (en) * | 1980-04-29 | 1983-12-16 | Shionogi & Co | 2-guanidino-4-(-acylaminoalkyl(thio)methyl)thiazoles and analogs |
CA1233818A (en) * | 1981-03-09 | 1988-03-08 | David J. Gilman | Guanidine derivatives as histamine h-2 receptor antagonists |
CA1209998A (en) * | 1981-03-09 | 1986-08-19 | David J. Gilman | Amide derivatives as histamine h-2 receptor antagonists |
IN158869B (da) * | 1981-03-18 | 1987-02-07 | Ici Plc | |
US4451463A (en) * | 1981-03-24 | 1984-05-29 | Imperial Chemical Industries Plc | Alcohol derivatives |
DE3267110D1 (de) * | 1981-05-18 | 1985-12-05 | Ici Plc | Amidine derivatives |
JPS5872571A (ja) * | 1981-10-27 | 1983-04-30 | Shionogi & Co Ltd | 2−グアニジノ−4−〔2−(ホルムアミド)エチルチオメチル〕チアゾ−ルの製法 |
US4808589A (en) * | 1982-02-20 | 1989-02-28 | Smith Kline & French Laboratories Limited | Pyrimidone derivatives |
EP0103390A3 (en) * | 1982-08-13 | 1986-02-26 | Imperial Chemical Industries Plc | Guanidine-containing esters as histamine h2 receptor blockers |
DE3238867A1 (de) * | 1982-10-20 | 1984-04-26 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | Heterocyclische verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
JPS59104370A (ja) * | 1982-12-03 | 1984-06-16 | Kotobuki Seiyaku Kk | チアゾ−ル誘導体及びその製造方法 |
JPS59227870A (ja) * | 1983-06-07 | 1984-12-21 | Yamanouchi Pharmaceut Co Ltd | 新規2−グアニジノチアゾリン誘導体ならびにその製造法 |
US4663347A (en) | 1983-10-31 | 1987-05-05 | Merck Frosst Canada, Inc. | Benzofuran 2-carboxylic acid esters useful as inhibitors of leukotriene biosynthesis |
GB8401751D0 (en) * | 1984-01-24 | 1984-02-29 | Ici Plc | Guanidine derivatives |
JPS6160673A (ja) * | 1984-08-30 | 1986-03-28 | Yamanouchi Pharmaceut Co Ltd | グアニジノチアゾ−ル誘導体の製造法 |
CA1309557C (en) | 1985-06-18 | 1992-10-27 | Robert N. Young | Leukotriene antagonists |
DE3786030T2 (de) | 1986-03-27 | 1993-12-02 | Merck Frosst Canada Inc | Tetrahydrocarbazole Ester. |
EP0284536A1 (en) * | 1987-02-20 | 1988-09-28 | Centro Marga Para La Investigacion S.A. | A process for the preparation of 3-(2-guanidinothiazol-4-yl-methylthio)propionitrile |
EP0480716A1 (en) | 1990-10-12 | 1992-04-15 | Merck Frosst Canada Inc. | Saturated hydroxyalkylquinoline acids as leukotriene antagonists |
US5410054A (en) * | 1993-07-20 | 1995-04-25 | Merck Frosst Canada, Inc. | Heteroaryl quinolines as inhibitors of leukotriene biosynthesis |
TW200517114A (en) | 2003-10-15 | 2005-06-01 | Combinatorx Inc | Methods and reagents for the treatment of immunoinflammatory disorders |
CA2628570A1 (en) | 2005-11-09 | 2007-05-18 | Combinatorx, Incorporated | Methods, compositions, and kits for the treatment of medical conditions |
EP3018125B1 (en) | 2013-07-03 | 2020-08-05 | Shin Nippon Biomedical Laboratories, Ltd. | Novel compound, organic cation transporter 3 detection agent, and organic cation transporter 3 activity inhibitor |
WO2015155297A1 (en) | 2014-04-11 | 2015-10-15 | Sanovel Ilac Sanayi Ve Ticaret A.S. | Pharmaceutical combinations of dabigatran and h2-receptor antagonists |
EP2942058A1 (en) | 2014-05-09 | 2015-11-11 | Sanovel Ilac Sanayi ve Ticaret A.S. | Pharmaceutical combinations of rivaroxaban and H2-receptor antagonists |
WO2021183259A1 (en) * | 2020-03-12 | 2021-09-16 | Nanopharmaceutics, Inc. | Famotidine and famotidine analogs for corona virus treatment |
EP4196793A1 (en) | 2020-08-11 | 2023-06-21 | Université de Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ186965A (en) * | 1977-04-20 | 1980-02-21 | Ici Ltd | Guanidino derivatives and pharmaceutical compositions |
US4165378A (en) * | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
DE2817078C2 (de) * | 1977-04-20 | 1995-06-14 | Zeneca Ltd | Guanidinderivate |
JPS6056143B2 (ja) * | 1979-08-02 | 1985-12-09 | 山之内製薬株式会社 | アミジン誘導体ならびにその製造法 |
-
1980
- 1980-02-26 PH PH23689A patent/PH16099A/en unknown
- 1980-03-03 DE DE19803008056 patent/DE3008056A1/de active Granted
- 1980-03-03 FR FR8004690A patent/FR2450827A1/fr active Granted
- 1980-03-04 CA CA000346986A patent/CA1145345A/en not_active Expired
- 1980-03-04 CH CH171680A patent/CH644114A5/de not_active IP Right Cessation
- 1980-03-05 ES ES80489222A patent/ES8103070A1/es not_active Expired
- 1980-03-05 SE SE8001691A patent/SE447253B/sv not_active IP Right Cessation
- 1980-03-05 IT IT67346/80A patent/IT1165509B/it active
- 1980-03-06 NL NL8001361A patent/NL8001361A/nl not_active Application Discontinuation
- 1980-03-06 GB GB8007702A patent/GB2052478B/en not_active Expired
- 1980-03-06 US US06/127,902 patent/US4362736A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CH644114A5 (de) | 1984-07-13 |
FR2450827A1 (fr) | 1980-10-03 |
ES489222A0 (es) | 1981-02-16 |
FR2450827B1 (da) | 1983-03-25 |
GB2052478B (en) | 1983-04-07 |
DE3008056A1 (de) | 1980-09-18 |
SE447253B (sv) | 1986-11-03 |
IT8067346A0 (it) | 1980-03-05 |
DE3008056C2 (da) | 1988-07-21 |
SE8001691L (sv) | 1980-09-07 |
US4362736A (en) | 1982-12-07 |
ES8103070A1 (es) | 1981-02-16 |
GB2052478A (en) | 1981-01-28 |
IT1165509B (it) | 1987-04-22 |
PH16099A (en) | 1983-06-24 |
CA1145345A (en) | 1983-04-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NL8001361A (nl) | Guanidinothiazoolverbindingen, werkwijzen ter bereiding ervan, alsmede farmaceutische preparaten die de guanidinothiazoolverbindingen bevatten. | |
US4283408A (en) | Guanidinothiazole compounds, process for preparation and gastric inhibiting compositions containing them | |
US3897444A (en) | Pharmacologically active compounds | |
SU1400508A3 (ru) | Способ получени производных арилтиазолов | |
PL98616B1 (pl) | Sposob wytwarzania trojpodstawionych guanidyn | |
SE416049B (sv) | Forfarande for framstellning av 1,1-diaminoctylenderivat, som kan anvendas for hemning av vissa histaminverkningar | |
CH626883A5 (da) | ||
PL118387B1 (en) | Process for preparing novel derivatives of thiadiazole | |
CS199255B2 (en) | Method of preparing pharmacologically active compounds | |
GB2088375A (en) | Imidazolylphenyl amidines | |
PL98615B1 (pl) | Sposob wytwarzania amidyn z mostkiem metylenowym | |
PL100317B1 (pl) | Sposob wytwarzania nowych pochodnych amidyny | |
NO781572L (no) | Fremgangsmaate for fremstilling av bisamidiner | |
US4728655A (en) | Sulfonamidines, process for the production thereof and pharmaceutical compositions containing the same | |
US3911010A (en) | Aminophenylamidines, their production and their pharmaceutical use | |
KR830002478B1 (ko) | 구아니디노 티아졸 화합물의 제조방법 | |
US4492711A (en) | Benzamides, their salts, and pharmaceutical compositions containing them | |
FI70890C (fi) | Foerfarande foer framstaellning av farmakologiskt vaerdefulla guanidinotiazolfoereningar | |
HU187877B (en) | Process for preparing guanidino-heterocyclyl-phenyl-amidines and pharmaceutical compositions containing thereof | |
CA1178590A (en) | Imidazolecarboxamide derivatives | |
US4093729A (en) | N-Oxy and N-amino guanidines | |
SK9842001A3 (en) | ((aminoiminomethyl)amino) alkanecarboxamides and their applications in therapy | |
US4090026A (en) | Certain nitrogen heterocyclic isothiocyanate esters | |
SI8010622A8 (sl) | Postopek pridobivanja gvanidintiazolnih spojin | |
GB2192884A (en) | Substituted ethanediimidamides |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
BA | A request for search or an international-type search has been filed | ||
BB | A search report has been drawn up | ||
BC | A request for examination has been filed | ||
A85 | Still pending on 85-01-01 | ||
BV | The patent application has lapsed |