KR20050107611A - 구아니딘 유도체 및 신경펩티드 ｆｆ 수용체 길항제로서이들의 용도 - Google Patents

Info

Publication number

KR20050107611A

KR20050107611A KR1020057016769A KR20057016769A KR20050107611A KR 20050107611 A KR20050107611 A KR 20050107611A KR 1020057016769 A KR1020057016769 A KR 1020057016769A KR 20057016769 A KR20057016769 A KR 20057016769A KR 20050107611 A KR20050107611 A KR 20050107611A

Authority

KR

South Korea

Prior art keywords

tetrahydro

guanidine

benzothiazol

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.)

Withdrawn

Links

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• 150000002357 guanidines Chemical class 0.000 title claims abstract description 9
• 102000011015 Neuropeptide FF receptor Human genes 0.000 title abstract description 11
• 108010061550 Neuropeptide FF receptor Proteins 0.000 title abstract description 11
• 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 title abstract description 6
• 229940044551 receptor antagonist Drugs 0.000 title description 6
• 239000002464 receptor antagonist Substances 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 135
• 150000003839 salts Chemical class 0.000 claims abstract description 28
• 125000000524 functional group Chemical group 0.000 claims abstract description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
• 125000001424 substituent group Chemical group 0.000 claims abstract description 24
• 239000002253 acid Substances 0.000 claims abstract description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 17
• 150000002148 esters Chemical class 0.000 claims abstract description 16
• 208000002193 Pain Diseases 0.000 claims abstract description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
• 238000000034 method Methods 0.000 claims abstract description 12
• 125000004429 atom Chemical group 0.000 claims abstract description 11
• 238000011282 treatment Methods 0.000 claims abstract description 11
• 150000004677 hydrates Chemical class 0.000 claims abstract description 9
• 239000012453 solvate Substances 0.000 claims abstract description 9
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 8
• 239000001257 hydrogen Substances 0.000 claims abstract description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
• 150000007514 bases Chemical class 0.000 claims abstract description 7
• 230000036407 pain Effects 0.000 claims abstract description 7
• 208000005374 Poisoning Diseases 0.000 claims abstract description 6
• 239000003814 drug Substances 0.000 claims abstract description 6
• 231100000572 poisoning Toxicity 0.000 claims abstract description 6
• 230000000607 poisoning effect Effects 0.000 claims abstract description 6
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims abstract description 5
• 230000036772 blood pressure Effects 0.000 claims abstract description 5
• 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
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 4
• 230000035987 intoxication Effects 0.000 claims abstract description 4
• 231100000566 intoxication Toxicity 0.000 claims abstract description 4
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims abstract description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
• 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 3
• 206010048010 Withdrawal syndrome Diseases 0.000 claims abstract description 3
• 229960002715 nicotine Drugs 0.000 claims abstract description 3
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims abstract description 3
• 229940001470 psychoactive drug Drugs 0.000 claims abstract description 3
• 239000004089 psychotropic agent Substances 0.000 claims abstract description 3
• 230000010656 regulation of insulin secretion Effects 0.000 claims abstract description 3
• -1 arylalkanoyl Chemical group 0.000 claims description 151
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 86
• XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 69
• 238000002360 preparation method Methods 0.000 claims description 51
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 125000003118 aryl group Chemical group 0.000 claims description 26
• 239000002904 solvent Substances 0.000 claims description 23
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 17
• 125000003342 alkenyl group Chemical group 0.000 claims description 14
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000004966 cyanoalkyl group Chemical group 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
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• UELDUEAYRHAPRG-UHFFFAOYSA-N 2-(diaminomethylideneamino)-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxylic acid Chemical compound OC(=O)C1CCCC2=C1N=C(NC(=N)N)S2 UELDUEAYRHAPRG-UHFFFAOYSA-N 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
• 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
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 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 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
• 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 4
• ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 claims description 4
• TWUFTVMULHEFJW-UHFFFAOYSA-N ethyl 2-(diaminomethylideneamino)-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxylate Chemical compound CCOC(=O)C1CCCC2=C1N=C(NC(N)=N)S2 TWUFTVMULHEFJW-UHFFFAOYSA-N 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• CKBIOORETGHJLB-UHFFFAOYSA-N 2-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)guanidine Chemical compound C1CCCC2=C1N=C(NC(=N)N)S2 CKBIOORETGHJLB-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• IQSJJHUZFHAQCL-UHFFFAOYSA-N 2-(diaminomethylideneamino)-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1CC(C(O)=O)CC2=C1N=C(NC(=N)N)S2 IQSJJHUZFHAQCL-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• GYHPCMXILICUER-UHFFFAOYSA-N 2-[4-(aminomethyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]guanidine Chemical compound NCC1CCCC2=C1N=C(NC(N)=N)S2 GYHPCMXILICUER-UHFFFAOYSA-N 0.000 claims description 3
• UNBXYGBSCOOLMA-UHFFFAOYSA-N 2-[4-(azidomethyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]guanidine Chemical compound [N-]=[N+]=NCC1CCCC2=C1N=C(NC(=N)N)S2 UNBXYGBSCOOLMA-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• LYOYGNAUXUNRNG-UHFFFAOYSA-N 2-[4-(hydroxymethyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]guanidine Chemical compound OCC1CCCC2=C1N=C(NC(=N)N)S2 LYOYGNAUXUNRNG-UHFFFAOYSA-N 0.000 claims description 3
• KUORHFIBNWNBCM-UHFFFAOYSA-N 2-[4-methyl-4-(2-methylpropyl)-6,7-dihydro-5h-1,3-benzothiazol-2-yl]guanidine Chemical compound CC(C)CC1(C)CCCC2=C1N=C(NC(N)=N)S2 KUORHFIBNWNBCM-UHFFFAOYSA-N 0.000 claims description 3
• VBWKHBVNGLOMEL-UHFFFAOYSA-N 2-[6-(3,4-dimethoxyphenyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]guanidine Chemical compound C1=C(OC)C(OC)=CC=C1C1CC(SC(NC(N)=N)=N2)=C2CC1 VBWKHBVNGLOMEL-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
• RWOUHUFQVUBVRO-UHFFFAOYSA-N [2-(diaminomethylideneamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-4-yl]methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1C(N=C(NC(N)=N)S2)=C2CCC1 RWOUHUFQVUBVRO-UHFFFAOYSA-N 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
• DCGJECYGJUQGCL-UHFFFAOYSA-N benzyl 2-(diaminomethylideneamino)-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carboxylate Chemical compound C1C=2SC(NC(=N)N)=NC=2CCN1C(=O)OCC1=CC=CC=C1 DCGJECYGJUQGCL-UHFFFAOYSA-N 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
• YIXNBCRNHLMGKU-UHFFFAOYSA-N ethyl 2-(diaminomethylideneamino)-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylate Chemical compound C1C(C(=O)OCC)CCC2=C1SC(NC(N)=N)=N2 YIXNBCRNHLMGKU-UHFFFAOYSA-N 0.000 claims description 3
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• OYDVACUZLCNVEJ-UHFFFAOYSA-N n-[[2-(diaminomethylideneamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl]methyl]acetamide Chemical compound C1C(CNC(=O)C)CCC2=C1SC(NC(N)=N)=N2 OYDVACUZLCNVEJ-UHFFFAOYSA-N 0.000 claims description 3
• YFAYZKDRBXKNLV-UHFFFAOYSA-N n-benzyl-2-(diaminomethylideneamino)-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxamide Chemical compound C1CCC=2SC(NC(=N)N)=NC=2C1C(=O)NCC1=CC=CC=C1 YFAYZKDRBXKNLV-UHFFFAOYSA-N 0.000 claims description 3
• RZCYPAMUJHRHHV-UHFFFAOYSA-N n-benzyl-2-(diaminomethylideneamino)-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carbothioamide Chemical compound C1C=2SC(NC(=N)N)=NC=2CCN1C(=S)NCC1=CC=CC=C1 RZCYPAMUJHRHHV-UHFFFAOYSA-N 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
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