CA2518679A1 - Guanidine derivatives and use thereof as neuropeptide ff receptor antagonists - Google Patents

Info

Publication number

CA2518679A1

CA2518679A1 CA002518679A CA2518679A CA2518679A1 CA 2518679 A1 CA2518679 A1 CA 2518679A1 CA 002518679 A CA002518679 A CA 002518679A CA 2518679 A CA2518679 A CA 2518679A CA 2518679 A1 CA2518679 A1 CA 2518679A1

Authority

CA

Canada

Prior art keywords

tetrahydro

guanidine

benzothiazole

formate

thiazolo

Prior art date

2003-03-20

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 title claims abstract description 10
• 150000002357 guanidines Chemical class 0.000 title claims abstract description 9
• 102000011015 Neuropeptide FF receptor Human genes 0.000 title claims description 12
• 108010061550 Neuropeptide FF receptor Proteins 0.000 title claims description 12
• 239000002464 receptor antagonist Substances 0.000 title claims description 8
• 229940044551 receptor antagonist Drugs 0.000 title claims description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 124
• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 239000002253 acid Substances 0.000 claims abstract description 25
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
• 125000001424 substituent group Chemical group 0.000 claims abstract description 20
• 150000002148 esters Chemical class 0.000 claims abstract description 18
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 17
• 208000002193 Pain Diseases 0.000 claims abstract description 15
• 238000000034 method Methods 0.000 claims abstract description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
• 238000011282 treatment Methods 0.000 claims abstract description 11
• 239000012453 solvate Substances 0.000 claims abstract description 10
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 9
• 230000036407 pain Effects 0.000 claims abstract description 9
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 8
• 150000007514 bases Chemical class 0.000 claims abstract description 8
• 150000004677 hydrates Chemical class 0.000 claims abstract description 7
• 239000003792 electrolyte Substances 0.000 claims abstract description 5
• 230000037406 food intake Effects 0.000 claims abstract description 5
• 235000012631 food intake Nutrition 0.000 claims abstract description 5
• 230000006386 memory function Effects 0.000 claims abstract description 5
• 208000004454 Hyperalgesia Diseases 0.000 claims abstract description 4
• 208000035154 Hyperesthesia Diseases 0.000 claims abstract description 4
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims abstract description 4
• 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 4
• 230000036772 blood pressure Effects 0.000 claims abstract description 4
• 230000006872 improvement Effects 0.000 claims abstract description 3
• 230000000506 psychotropic effect Effects 0.000 claims abstract description 3
• -1 arylalkanoyl Chemical group 0.000 claims description 182
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 83
• 238000002360 preparation method Methods 0.000 claims description 56
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• 125000003118 aryl group Chemical group 0.000 claims description 23
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 17
• 125000003342 alkenyl group Chemical group 0.000 claims description 14
• OKGXJRGLYVRVNE-UHFFFAOYSA-N diaminomethylidenethiourea Chemical compound NC(N)=NC(N)=S OKGXJRGLYVRVNE-UHFFFAOYSA-N 0.000 claims description 14
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
• 229940126601 medicinal product Drugs 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 238000007363 ring formation reaction Methods 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• LNXDWHDZNHLNAB-UHFFFAOYSA-N 2-(5-butyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(CCCC)CCC2=C1N=C(NC(N)=N)S2 LNXDWHDZNHLNAB-UHFFFAOYSA-N 0.000 claims description 3
• QDOXNVJQBUENNN-UHFFFAOYSA-N 2-(6-propan-2-yl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(C(C)C)CCC2=C1SC(NC(N)=N)=N2 QDOXNVJQBUENNN-UHFFFAOYSA-N 0.000 claims description 3
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• 206010048010 Withdrawal syndrome Diseases 0.000 claims description 3
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
• 125000005116 aryl carbamoyl group Chemical group 0.000 claims description 3
• 125000001589 carboacyl group Chemical group 0.000 claims description 3
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
• 230000010656 regulation of insulin secretion Effects 0.000 claims description 3
• OYRIEZNQPFTEKZ-UHFFFAOYSA-N tert-butyl 2-(diaminomethylideneamino)-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1SC(NC(N)=N)=N2 OYRIEZNQPFTEKZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• WUUADCHFBLXQKF-UHFFFAOYSA-N 2-(4,4-dimethyl-6,7-dihydro-5h-1,3-benzothiazol-2-yl)guanidine Chemical compound CC1(C)CCCC2=C1N=C(NC(N)=N)S2 WUUADCHFBLXQKF-UHFFFAOYSA-N 0.000 claims description 2
• FUGBYHUCJPEPJR-UHFFFAOYSA-N 2-(4-benzyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1CCC=2SC(NC(=N)N)=NC=2C1CC1=CC=CC=C1 FUGBYHUCJPEPJR-UHFFFAOYSA-N 0.000 claims description 2
• NDKWSGBHKXFNCC-UHFFFAOYSA-N 2-(4-butan-2-yl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound CCC(C)C1CCCC2=C1N=C(NC(N)=N)S2 NDKWSGBHKXFNCC-UHFFFAOYSA-N 0.000 claims description 2
• QSOMFWDDWOFLBS-UHFFFAOYSA-N 2-(4-ethyl-4-methyl-6,7-dihydro-5h-1,3-benzothiazol-2-yl)guanidine Chemical compound CCC1(C)CCCC2=C1N=C(NC(N)=N)S2 QSOMFWDDWOFLBS-UHFFFAOYSA-N 0.000 claims description 2
• OYBQOMBJSHYEAL-UHFFFAOYSA-N 2-(4-methyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound CC1CCCC2=C1N=C(NC(N)=N)S2 OYBQOMBJSHYEAL-UHFFFAOYSA-N 0.000 claims description 2
• LYLYGOUPJRCBLS-UHFFFAOYSA-N 2-(4-methyl-4-propyl-6,7-dihydro-5h-1,3-benzothiazol-2-yl)guanidine Chemical compound CCCC1(C)CCCC2=C1N=C(NC(N)=N)S2 LYLYGOUPJRCBLS-UHFFFAOYSA-N 0.000 claims description 2
• BYPPQYJAMBPADG-UHFFFAOYSA-N 2-(4-phenyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1CCC=2SC(NC(=N)N)=NC=2C1C1=CC=CC=C1 BYPPQYJAMBPADG-UHFFFAOYSA-N 0.000 claims description 2
• ALIMGROCSLBETQ-UHFFFAOYSA-N 2-(4-tert-butyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound CC(C)(C)C1CCCC2=C1N=C(NC(N)=N)S2 ALIMGROCSLBETQ-UHFFFAOYSA-N 0.000 claims description 2
• UCXUJAFVTACPGW-UHFFFAOYSA-N 2-(4-tert-butyl-6-phenyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C=2SC(NC(N)=N)=NC=2C(C(C)(C)C)CC1C1=CC=CC=C1 UCXUJAFVTACPGW-UHFFFAOYSA-N 0.000 claims description 2
• QXOFHSUKWFCEBI-UHFFFAOYSA-N 2-(5,5,7,7-tetramethyl-4,6-dihydro-1,3-benzothiazol-2-yl)guanidine Chemical compound CC1(C)CC(C)(C)CC2=C1SC(NC(N)=N)=N2 QXOFHSUKWFCEBI-UHFFFAOYSA-N 0.000 claims description 2
• WLACEDJDTIXJHA-UHFFFAOYSA-N 2-(5,5,7-trimethyl-6,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound CC1CC(C)(C)CC2=C1SC(NC(N)=N)=N2 WLACEDJDTIXJHA-UHFFFAOYSA-N 0.000 claims description 2
• KLFUHWVGNPXLLK-UHFFFAOYSA-N 2-(5,5-dimethyl-6,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(C)(C)CCC2=C1N=C(NC(N)=N)S2 KLFUHWVGNPXLLK-UHFFFAOYSA-N 0.000 claims description 2
• JVACMLRJYVWKJM-UHFFFAOYSA-N 2-(5,5-dimethyl-6-phenyl-6,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound CC1(C)CC=2N=C(NC(N)=N)SC=2CC1C1=CC=CC=C1 JVACMLRJYVWKJM-UHFFFAOYSA-N 0.000 claims description 2
• UFTXCRWHCXBQKN-UHFFFAOYSA-N 2-(5,6,7,8-tetrahydro-4h-cyclohepta[d][1,3]thiazol-2-yl)guanidine Chemical compound C1CCCCC2=C1N=C(NC(=N)N)S2 UFTXCRWHCXBQKN-UHFFFAOYSA-N 0.000 claims description 2
• UAIBRYGHVVYQBK-UHFFFAOYSA-N 2-(5,6-dihydro-4h-cyclopenta[d][1,3]thiazol-2-yl)guanidine Chemical compound C1CCC2=C1N=C(NC(=N)N)S2 UAIBRYGHVVYQBK-UHFFFAOYSA-N 0.000 claims description 2
• SABCLZIQZNALTP-UHFFFAOYSA-N 2-(5-benzyl-4,6,7,8-tetrahydro-[1,3]thiazolo[4,5-c]azepin-2-yl)guanidine Chemical compound C1CCC=2SC(NC(=N)N)=NC=2CN1CC1=CC=CC=C1 SABCLZIQZNALTP-UHFFFAOYSA-N 0.000 claims description 2
• FSWGIXWSQKVRBR-UHFFFAOYSA-N 2-(5-benzyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1C=2SC(NC(=N)N)=NC=2CCN1CC1=CC=CC=C1 FSWGIXWSQKVRBR-UHFFFAOYSA-N 0.000 claims description 2
• SGUKNSYVBNMKLK-UHFFFAOYSA-N 2-(5-but-3-enoyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1CN(C(=O)CC=C)CC2=C1N=C(NC(=N)N)S2 SGUKNSYVBNMKLK-UHFFFAOYSA-N 0.000 claims description 2
• GMABAPWOAXNDDE-UHFFFAOYSA-N 2-(5-butyl-5,6,7,8-tetrahydro-4h-cyclohepta[d][1,3]thiazol-2-yl)guanidine Chemical compound C1C(CCCC)CCCC2=C1N=C(NC(N)=N)S2 GMABAPWOAXNDDE-UHFFFAOYSA-N 0.000 claims description 2
• UPEQOVLNRJIVEL-UHFFFAOYSA-N 2-(5-butylsulfonyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1N(S(=O)(=O)CCCC)CCC2=C1SC(NC(N)=N)=N2 UPEQOVLNRJIVEL-UHFFFAOYSA-N 0.000 claims description 2
• ZYPREDXHNDNTCV-UHFFFAOYSA-N 2-(5-ethyl-5-methyl-6,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(CC)(C)CCC2=C1N=C(NC(N)=N)S2 ZYPREDXHNDNTCV-UHFFFAOYSA-N 0.000 claims description 2
• YFOHSVMOPDQBTG-UHFFFAOYSA-N 2-(5-ethyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1N(CC)CCC2=C1SC(NC(N)=N)=N2 YFOHSVMOPDQBTG-UHFFFAOYSA-N 0.000 claims description 2
• DDMZPDGUXYIEAU-UHFFFAOYSA-N 2-(5-hexyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1N(CCCCCC)CCC2=C1SC(NC(N)=N)=N2 DDMZPDGUXYIEAU-UHFFFAOYSA-N 0.000 claims description 2
• RDQBDBMPQLZPSN-UHFFFAOYSA-N 2-(5-methyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(C)CCC2=C1N=C(NC(N)=N)S2 RDQBDBMPQLZPSN-UHFFFAOYSA-N 0.000 claims description 2
• ICDGFGKAIBXUJJ-UHFFFAOYSA-N 2-(5-methyl-5-phenyl-6,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound C1CC=2SC(NC(N)=N)=NC=2CC1(C)C1=CC=CC=C1 ICDGFGKAIBXUJJ-UHFFFAOYSA-N 0.000 claims description 2
• RHNOCHLHOYFGLC-UHFFFAOYSA-N 2-(5-methylsulfonyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1N(S(=O)(=O)C)CCC2=C1SC(NC(N)=N)=N2 RHNOCHLHOYFGLC-UHFFFAOYSA-N 0.000 claims description 2
• BQTZVYKQEGHYIG-UHFFFAOYSA-N 2-(5-pentanoyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1N(C(=O)CCCC)CCC2=C1SC(NC(N)=N)=N2 BQTZVYKQEGHYIG-UHFFFAOYSA-N 0.000 claims description 2
• AOCYGZXXCPMOJM-UHFFFAOYSA-N 2-(5-phenyl-5,6,7,8-tetrahydro-4h-cyclohepta[d][1,3]thiazol-2-yl)guanidine Chemical compound C1CCC=2SC(NC(=N)N)=NC=2CC1C1=CC=CC=C1 AOCYGZXXCPMOJM-UHFFFAOYSA-N 0.000 claims description 2
• SKVHXDFCKUOUHJ-UHFFFAOYSA-N 2-(5-prop-2-ynyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1CN(CC#C)CC2=C1N=C(NC(=N)N)S2 SKVHXDFCKUOUHJ-UHFFFAOYSA-N 0.000 claims description 2
• FBUBOFVNIZACRW-UHFFFAOYSA-N 2-(5-propyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)guanidine Chemical compound C1N(CCC)CCC2=C1SC(NC(N)=N)=N2 FBUBOFVNIZACRW-UHFFFAOYSA-N 0.000 claims description 2
• AKOBTVQNQFUIFL-UHFFFAOYSA-N 2-(6,6-dimethyl-5,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(C)(C)CCC2=C1SC(NC(N)=N)=N2 AKOBTVQNQFUIFL-UHFFFAOYSA-N 0.000 claims description 2
• WVXCYAIRSGWGBV-UHFFFAOYSA-N 2-(6,6-diphenyl-5,7-dihydro-4h-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C=2SC(NC(=N)N)=NC=2CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 WVXCYAIRSGWGBV-UHFFFAOYSA-N 0.000 claims description 2
• CYXYEESUXIALNC-UHFFFAOYSA-N 2-(6,7-dihydro-4h-pyrano[4,3-d][1,3]thiazol-2-yl)guanidine Chemical compound C1COCC2=C1N=C(NC(=N)N)S2 CYXYEESUXIALNC-UHFFFAOYSA-N 0.000 claims description 2
• GUWOIUDVUADBQM-UHFFFAOYSA-N 2-(6-methyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(C)CCC2=C1SC(NC(N)=N)=N2 GUWOIUDVUADBQM-UHFFFAOYSA-N 0.000 claims description 2
• WPRMMSUIODPDQQ-UHFFFAOYSA-N 2-(6-phenyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C=2SC(NC(=N)N)=NC=2CCC1C1=CC=CC=C1 WPRMMSUIODPDQQ-UHFFFAOYSA-N 0.000 claims description 2
• GGSJEFBOSRYGBZ-UHFFFAOYSA-N 2-(6-propyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(CCC)CCC2=C1SC(NC(N)=N)=N2 GGSJEFBOSRYGBZ-UHFFFAOYSA-N 0.000 claims description 2
• RFZXGFBVQUEHCE-UHFFFAOYSA-N 2-(6-tert-butyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C(C(C)(C)C)CCC2=C1SC(NC(N)=N)=N2 RFZXGFBVQUEHCE-UHFFFAOYSA-N 0.000 claims description 2
• XHPLIMKFVJUFOQ-UHFFFAOYSA-N 2-(6-thiophen-2-yl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1C=2SC(NC(=N)N)=NC=2CCC1C1=CC=CS1 XHPLIMKFVJUFOQ-UHFFFAOYSA-N 0.000 claims description 2
• WVIAKQLSKCZTNT-UHFFFAOYSA-N 2-(7-methyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound CC1CCCC2=C1SC(NC(N)=N)=N2 WVIAKQLSKCZTNT-UHFFFAOYSA-N 0.000 claims description 2
• GOJROTMNJNWGMG-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-(1-methoxypropan-2-yl)-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carbothioamide Chemical compound C1N(C(=S)NC(C)COC)CCC2=C1SC(NC(N)=N)=N2 GOJROTMNJNWGMG-UHFFFAOYSA-N 0.000 claims description 2
• GRFKGPRMVDHIBO-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-(3-methylbutyl)-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxamide;formic acid Chemical compound OC=O.CC(C)CCNC(=O)C1CCCC2=C1N=C(NC(N)=N)S2 GRFKGPRMVDHIBO-UHFFFAOYSA-N 0.000 claims description 2
• YHBVQQYSGAVNFE-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-pentyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carboxamide Chemical compound C1N(C(=O)NCCCCC)CCC2=C1SC(NC(N)=N)=N2 YHBVQQYSGAVNFE-UHFFFAOYSA-N 0.000 claims description 2
• QJHYMDXVSYZIDQ-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-phenyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carboxamide Chemical compound C1C=2SC(NC(=N)N)=NC=2CCN1C(=O)NC1=CC=CC=C1 QJHYMDXVSYZIDQ-UHFFFAOYSA-N 0.000 claims description 2
• ZCBZWGQVGHFAOB-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-propan-2-yl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carbothioamide Chemical compound C1N(C(=S)NC(C)C)CCC2=C1SC(N=C(N)N)=N2 ZCBZWGQVGHFAOB-UHFFFAOYSA-N 0.000 claims description 2
• QWHJPAKVYVBKFQ-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-propyl-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxamide Chemical compound C1C(C(=O)NCCC)CCC2=C1SC(NC(N)=N)=N2 QWHJPAKVYVBKFQ-UHFFFAOYSA-N 0.000 claims description 2
• YAJZFNWYKDVSPN-UHFFFAOYSA-N 2-(diaminomethylideneamino)-n-propyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carbothioamide Chemical compound C1N(C(=S)NCCC)CCC2=C1SC(NC(N)=N)=N2 YAJZFNWYKDVSPN-UHFFFAOYSA-N 0.000 claims description 2
• OLDBFYAXTHRQGT-UHFFFAOYSA-N 2-[4-(2-cyanoethyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]guanidine Chemical compound N#CCCC1CCCC2=C1N=C(NC(=N)N)S2 OLDBFYAXTHRQGT-UHFFFAOYSA-N 0.000 claims description 2
• WVJSAIQHGDIBGB-UHFFFAOYSA-N 2-[4-(cyclohexen-1-yl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]guanidine Chemical compound C1CCC=2SC(NC(=N)N)=NC=2C1C1=CCCCC1 WVJSAIQHGDIBGB-UHFFFAOYSA-N 0.000 claims description 2
• PGEHXVOYKVRYKK-UHFFFAOYSA-N 2-[4-(morpholine-4-carbonyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]guanidine Chemical compound C1CCC=2SC(NC(=N)N)=NC=2C1C(=O)N1CCOCC1 PGEHXVOYKVRYKK-UHFFFAOYSA-N 0.000 claims description 2
• QBAXFGDLEDRYCD-UHFFFAOYSA-N 2-[4-(piperidine-1-carbonyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]guanidine Chemical compound C1CCC=2SC(NC(=N)N)=NC=2C1C(=O)N1CCCCC1 QBAXFGDLEDRYCD-UHFFFAOYSA-N 0.000 claims description 2
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