JP2007504176A - グアニジン誘導体 - Google Patents
グアニジン誘導体 Download PDFInfo
- Publication number
- JP2007504176A JP2007504176A JP2006525025A JP2006525025A JP2007504176A JP 2007504176 A JP2007504176 A JP 2007504176A JP 2006525025 A JP2006525025 A JP 2006525025A JP 2006525025 A JP2006525025 A JP 2006525025A JP 2007504176 A JP2007504176 A JP 2007504176A
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- JP
- Japan
- Prior art keywords
- tetrahydro
- compound
- guanidine
- rac
- formula
- Prior art date
- 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.)
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- 150000002357 guanidines Chemical class 0.000 title claims abstract description 10
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 title claims abstract description 7
- 238000011282 treatment Methods 0.000 claims abstract description 23
- 208000002193 Pain Diseases 0.000 claims abstract description 18
- 230000036407 pain Effects 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003792 electrolyte Substances 0.000 claims abstract description 7
- 230000037406 food intake Effects 0.000 claims abstract description 7
- 235000012631 food intake Nutrition 0.000 claims abstract description 7
- 230000006386 memory function Effects 0.000 claims abstract description 7
- 239000012453 solvate Substances 0.000 claims abstract description 7
- 206010012335 Dependence Diseases 0.000 claims abstract description 6
- 206010057852 Nicotine dependence Diseases 0.000 claims abstract description 6
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims abstract description 6
- 208000025569 Tobacco Use disease Diseases 0.000 claims abstract description 6
- 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 6
- 206010048010 Withdrawal syndrome Diseases 0.000 claims abstract description 6
- 230000003914 insulin secretion Effects 0.000 claims abstract description 6
- 229940001470 psychoactive drug Drugs 0.000 claims abstract description 6
- 239000004089 psychotropic agent Substances 0.000 claims abstract description 6
- 208000004454 Hyperalgesia Diseases 0.000 claims abstract description 5
- 208000035154 Hyperesthesia Diseases 0.000 claims abstract description 5
- 150000004677 hydrates Chemical class 0.000 claims abstract description 5
- 229940122109 Neuropeptide FF receptor antagonist Drugs 0.000 claims abstract 2
- UMKHUSRDQFQHAK-RNJMTYCLSA-N RF9 Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)C12CC3CC(CC(C3)C1)C2)CCCNC(=N)N)C(N)=O)C1=CC=CC=C1 UMKHUSRDQFQHAK-RNJMTYCLSA-N 0.000 claims abstract 2
- -1 thiadiazanaphthalene Chemical compound 0.000 claims description 135
- 150000001875 compounds Chemical class 0.000 claims description 113
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 10
- LFVVNPBBFUSSHL-UHFFFAOYSA-N alexidine Chemical compound CCCCC(CC)CNC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NCC(CC)CCCC LFVVNPBBFUSSHL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 9
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 8
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 8
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 7
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 7
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
- 125000004967 formylalkyl group Chemical group 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229950010221 alexidine Drugs 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 5
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 5
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 5
- 230000008030 elimination Effects 0.000 claims description 5
- 238000003379 elimination reaction Methods 0.000 claims description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- XCZPDOCRSYZOBI-UHFFFAOYSA-N 5,6,7,8-Tetrahydroquinoxaline Chemical compound C1=CN=C2CCCCC2=N1 XCZPDOCRSYZOBI-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 125000005116 aryl carbamoyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 229940127557 pharmaceutical product Drugs 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000005594 diketone group Chemical group 0.000 claims description 3
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 3
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 230000006872 improvement Effects 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 3
- JZVATIQSUFESHS-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,2,3-benzotriazine Chemical compound C1=CC=C2CNNNC2=C1 JZVATIQSUFESHS-UHFFFAOYSA-N 0.000 claims description 2
- ZCZVGQCBSJLDDS-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,8-naphthyridine Chemical compound C1=CC=C2CCCNC2=N1 ZCZVGQCBSJLDDS-UHFFFAOYSA-N 0.000 claims description 2
- BHKODZGDVUUACI-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrido[3,2-d]triazine Chemical compound C1=CN=C2CNNNC2=C1 BHKODZGDVUUACI-UHFFFAOYSA-N 0.000 claims description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical class N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 2
- REOZEPNIJZQMLX-UHFFFAOYSA-N 1h-cyclohepta[b]pyrazine Chemical compound C1=CC=CC=C2NC=CN=C21 REOZEPNIJZQMLX-UHFFFAOYSA-N 0.000 claims description 2
- HCLXLZGAYCTHQJ-UHFFFAOYSA-N 1h-cyclohepta[b]pyridine Chemical class C1=CC=CC=C2NC=CC=C21 HCLXLZGAYCTHQJ-UHFFFAOYSA-N 0.000 claims description 2
- BKARLPMXLIRRID-UHFFFAOYSA-N 1h-cyclohepta[d]pyrimidine Chemical compound C1=CC=CC=C2NC=NC=C21 BKARLPMXLIRRID-UHFFFAOYSA-N 0.000 claims description 2
- KEOWKZFSSBVUIW-UHFFFAOYSA-N 1h-cyclopenta[b]pyrazine Chemical compound C1=CNC2=CC=CC2=N1 KEOWKZFSSBVUIW-UHFFFAOYSA-N 0.000 claims description 2
- LTFBFZBWUKWXID-UHFFFAOYSA-N 1h-cyclopenta[d]pyrimidine Chemical compound N1=CNC2=CC=CC2=C1 LTFBFZBWUKWXID-UHFFFAOYSA-N 0.000 claims description 2
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical class C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims description 2
- LJGKMJWLEQYVEG-UHFFFAOYSA-N 2,3,4,4a-tetrahydro-1h-cyclohepta[d]triazine Chemical compound C1=CC=CC2CNNNC2=C1 LJGKMJWLEQYVEG-UHFFFAOYSA-N 0.000 claims description 2
- JKWQHCSGMTWRIQ-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NCCC2=N1 JKWQHCSGMTWRIQ-UHFFFAOYSA-N 0.000 claims description 2
- PJVQPPHJEYPUDB-UHFFFAOYSA-N 2,3-dihydrofuro[3,2-b]pyridine Chemical compound C1=CC=C2OCCC2=N1 PJVQPPHJEYPUDB-UHFFFAOYSA-N 0.000 claims description 2
- YBMFFLZLOZRFDD-UHFFFAOYSA-N 2,3-dihydrothieno[3,2-b]pyridine Chemical compound C1=CC=C2SCCC2=N1 YBMFFLZLOZRFDD-UHFFFAOYSA-N 0.000 claims description 2
- DZVMZYRUBJDTPQ-UHFFFAOYSA-N 2-(4,5-dimethyl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound NC(=N)NC1=NC(C)=C2C(C)CCCC2=N1 DZVMZYRUBJDTPQ-UHFFFAOYSA-N 0.000 claims description 2
- AQIXPPDRNFNPRW-UHFFFAOYSA-N 2-(4,6-dimethyl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound NC(=N)NC1=NC(C)=C2CC(C)CCC2=N1 AQIXPPDRNFNPRW-UHFFFAOYSA-N 0.000 claims description 2
- HRCXBKBEBGJMDJ-UHFFFAOYSA-N 2-(4,8-dimethyl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound N1=C(NC(N)=N)N=C2C(C)CCCC2=C1C HRCXBKBEBGJMDJ-UHFFFAOYSA-N 0.000 claims description 2
- IXDXFXQFNMXQQU-UHFFFAOYSA-N 2-(4-methyl-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidin-2-yl)guanidine Chemical compound C1CCCCCC2=C1N=C(N=C(N)N)N=C2C IXDXFXQFNMXQQU-UHFFFAOYSA-N 0.000 claims description 2
- ATKAGXXVMZWYGM-UHFFFAOYSA-N 2-(4-methyl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound C1CCCC2=C1N=C(N=C(N)N)N=C2C ATKAGXXVMZWYGM-UHFFFAOYSA-N 0.000 claims description 2
- NIULILZCZJKURO-UHFFFAOYSA-N 2-(4-methyl-6,7,8,9-tetrahydro-5h-cyclohepta[d]pyrimidin-2-yl)guanidine Chemical compound C1CCCCC2=C1N=C(NC(N)=N)N=C2C NIULILZCZJKURO-UHFFFAOYSA-N 0.000 claims description 2
- VVUHTEPXYZVIAU-UHFFFAOYSA-N 2-(4-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl)guanidine Chemical compound CC1=NC(NC(N)=N)=NC2=C1CCC2 VVUHTEPXYZVIAU-UHFFFAOYSA-N 0.000 claims description 2
- KDKLJCVVZFYRKV-UHFFFAOYSA-N 2-(4-methyl-6-phenyl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound C1C=2C(C)=NC(NC(N)=N)=NC=2CCC1C1=CC=CC=C1 KDKLJCVVZFYRKV-UHFFFAOYSA-N 0.000 claims description 2
- ZXRRRMMSIMSGTN-UHFFFAOYSA-N 2-(4-methyl-6-propan-2-yl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound NC(=N)NC1=NC(C)=C2CC(C(C)C)CCC2=N1 ZXRRRMMSIMSGTN-UHFFFAOYSA-N 0.000 claims description 2
- IWTUDKQIQBGRFW-UHFFFAOYSA-N 2-(4-methyl-6-propyl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound NC(=N)NC1=NC(C)=C2CC(CCC)CCC2=N1 IWTUDKQIQBGRFW-UHFFFAOYSA-N 0.000 claims description 2
- NWMKMGDIVMWXAX-UHFFFAOYSA-N 2-(4-methyl-8-phenyl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound C1CCC=2C(C)=NC(NC(N)=N)=NC=2C1C1=CC=CC=C1 NWMKMGDIVMWXAX-UHFFFAOYSA-N 0.000 claims description 2
- CWWOITPDZXNTSJ-UHFFFAOYSA-N 2-(5,6,7,8-tetrahydroquinolin-2-yl)guanidine Chemical compound C1CCCC2=NC(NC(=N)N)=CC=C21 CWWOITPDZXNTSJ-UHFFFAOYSA-N 0.000 claims description 2
- IJKMBMJUQLLNQO-UHFFFAOYSA-N 2-(5,6,7,8-tetrahydroquinoxalin-2-yl)guanidine Chemical compound C1CCCC2=NC(NC(=N)N)=CN=C21 IJKMBMJUQLLNQO-UHFFFAOYSA-N 0.000 claims description 2
- MOMBHZPOPKWDCA-UHFFFAOYSA-N 2-(6-phenyl-5,6,7,8-tetrahydro-1,2,4-benzotriazin-3-yl)guanidine Chemical compound C1C2=NC(NC(=N)N)=NN=C2CCC1C1=CC=CC=C1 MOMBHZPOPKWDCA-UHFFFAOYSA-N 0.000 claims description 2
- QFZUFBREJJYXLW-UHFFFAOYSA-N 2-(6-phenyl-5,6,7,8-tetrahydroquinolin-2-yl)guanidine Chemical compound C1CC2=NC(NC(=N)N)=CC=C2CC1C1=CC=CC=C1 QFZUFBREJJYXLW-UHFFFAOYSA-N 0.000 claims description 2
- IIZDBUQDDYDOEV-UHFFFAOYSA-N 2-(6-phenyl-5,6,7,8-tetrahydroquinoxalin-2-yl)guanidine Chemical compound C1CC2=NC(NC(=N)N)=CN=C2CC1C1=CC=CC=C1 IIZDBUQDDYDOEV-UHFFFAOYSA-N 0.000 claims description 2
- YDHAPKSUPXKXQA-UHFFFAOYSA-N 2-(6-propan-2-yl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound NC(=N)NC1=NC=C2CC(C(C)C)CCC2=N1 YDHAPKSUPXKXQA-UHFFFAOYSA-N 0.000 claims description 2
- SANNPHRRXQXGBH-UHFFFAOYSA-N 2-(6-propyl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound NC(=N)NC1=NC=C2CC(CCC)CCC2=N1 SANNPHRRXQXGBH-UHFFFAOYSA-N 0.000 claims description 2
- ASOOANNKZUSTMO-UHFFFAOYSA-N 2-(6-tert-butyl-4-methyl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound C1CC(C(C)(C)C)CC2=C1N=C(NC(N)=N)N=C2C ASOOANNKZUSTMO-UHFFFAOYSA-N 0.000 claims description 2
- OSXJUJDGUHKTJQ-UHFFFAOYSA-N 2-(6-tert-butyl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound NC(=N)NC1=NC=C2CC(C(C)(C)C)CCC2=N1 OSXJUJDGUHKTJQ-UHFFFAOYSA-N 0.000 claims description 2
- KMPYHOTXRHIQTQ-UHFFFAOYSA-N 2-(7-phenyl-5,6,7,8-tetrahydro-1,2,4-benzotriazin-3-yl)guanidine Chemical compound C1CC2=NC(NC(=N)N)=NN=C2CC1C1=CC=CC=C1 KMPYHOTXRHIQTQ-UHFFFAOYSA-N 0.000 claims description 2
- TVFFYWZXKFWYAR-UHFFFAOYSA-N 2-(7-phenyl-5,6,7,8-tetrahydroquinoxalin-2-yl)guanidine Chemical compound C1C2=NC(NC(=N)N)=CN=C2CCC1C1=CC=CC=C1 TVFFYWZXKFWYAR-UHFFFAOYSA-N 0.000 claims description 2
- MRFZBGDHMXHWBR-UHFFFAOYSA-N 2-(8-butan-2-yl-4-methyl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound N1=C(NC(N)=N)N=C2C(C(C)CC)CCCC2=C1C MRFZBGDHMXHWBR-UHFFFAOYSA-N 0.000 claims description 2
- YIFCRDLYZJGGJW-UHFFFAOYSA-N 2-(8-tert-butyl-4-methyl-5,6,7,8-tetrahydroquinazolin-2-yl)guanidine Chemical compound CC(C)(C)C1CCCC2=C1N=C(NC(N)=N)N=C2C YIFCRDLYZJGGJW-UHFFFAOYSA-N 0.000 claims description 2
- OFXMDUCSFGSEME-UHFFFAOYSA-N 2-[4-methyl-6-(2-methylbutan-2-yl)-5,6,7,8-tetrahydroquinazolin-2-yl]guanidine Chemical compound NC(=N)NC1=NC(C)=C2CC(C(C)(C)CC)CCC2=N1 OFXMDUCSFGSEME-UHFFFAOYSA-N 0.000 claims description 2
- UTTPPNFLOYXXBU-UHFFFAOYSA-N 2-[6-phenyl-4-(trifluoromethyl)-5,6,7,8-tetrahydroquinazolin-2-yl]guanidine Chemical compound C1C=2C(C(F)(F)F)=NC(NC(=N)N)=NC=2CCC1C1=CC=CC=C1 UTTPPNFLOYXXBU-UHFFFAOYSA-N 0.000 claims description 2
- FPTNCEKIDSBEQH-UHFFFAOYSA-N 2-[6-propan-2-yl-4-(trifluoromethyl)-5,6,7,8-tetrahydroquinazolin-2-yl]guanidine Chemical compound NC(=N)NC1=NC(C(F)(F)F)=C2CC(C(C)C)CCC2=N1 FPTNCEKIDSBEQH-UHFFFAOYSA-N 0.000 claims description 2
- DJAZRDWUHJGBPP-UHFFFAOYSA-N 2-[6-tert-butyl-4-(trifluoromethyl)-5,6,7,8-tetrahydroquinazolin-2-yl]guanidine Chemical compound NC(=N)NC1=NC(C(F)(F)F)=C2CC(C(C)(C)C)CCC2=N1 DJAZRDWUHJGBPP-UHFFFAOYSA-N 0.000 claims description 2
- GBCUUAHMGWGOBZ-UHFFFAOYSA-N 2-[8-(2-cyanoethyl)-4-methyl-5,6,7,8-tetrahydroquinazolin-2-yl]guanidine Chemical compound N#CCCC1CCCC2=C1N=C(NC(N)=N)N=C2C GBCUUAHMGWGOBZ-UHFFFAOYSA-N 0.000 claims description 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/84—Nitrogen atoms
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Addiction (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH15262003 | 2003-09-05 | ||
| PCT/CH2004/000556 WO2005023781A1 (de) | 2003-09-05 | 2004-09-03 | Guanidinderivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007504176A true JP2007504176A (ja) | 2007-03-01 |
| JP2007504176A5 JP2007504176A5 (enExample) | 2007-10-11 |
Family
ID=34230846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006525025A Pending JP2007504176A (ja) | 2003-09-05 | 2004-09-03 | グアニジン誘導体 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7544691B2 (enExample) |
| EP (1) | EP1663993B1 (enExample) |
| JP (1) | JP2007504176A (enExample) |
| KR (1) | KR20060064065A (enExample) |
| CN (1) | CN1845907B (enExample) |
| AT (1) | ATE388943T1 (enExample) |
| AU (1) | AU2004270304A1 (enExample) |
| BR (1) | BRPI0414103A (enExample) |
| CA (1) | CA2536927A1 (enExample) |
| DE (1) | DE502004006515D1 (enExample) |
| ES (1) | ES2300807T3 (enExample) |
| IL (1) | IL173853A0 (enExample) |
| NO (1) | NO20061531L (enExample) |
| PL (1) | PL1663993T3 (enExample) |
| RU (1) | RU2006110738A (enExample) |
| WO (1) | WO2005023781A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013515728A (ja) * | 2009-12-24 | 2013-05-09 | ノボマー， インコーポレイテッド | 多環式グアニジン化合物の合成のための方法 |
| WO2015002150A1 (ja) | 2013-07-03 | 2015-01-08 | 株式会社新日本科学 | 新規化合物，有機カチオントランスポーター３の検出剤及び活性阻害剤 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE521512C2 (sv) | 2001-06-25 | 2003-11-11 | Niconovum Ab | Anordning för administrering av en substans till främre delen av en individs munhåla |
| ATE359075T1 (de) | 2002-12-20 | 2007-05-15 | Niconovum Ab | Chemisch und physikalisch stabiles teilchenförmiges material enthaltend nikotin und microcrystalline cellulose |
| CA2646942C (en) | 2006-03-16 | 2014-07-29 | Niconovum Ab | Improved snuff composition |
| MX2019008078A (es) | 2017-02-14 | 2019-11-05 | Res Triangle Inst | Moduladores de receptores neuropeptido basados en prolina. |
| CN108159032A (zh) * | 2018-01-24 | 2018-06-15 | 昆明理工大学 | 二甲双胍在制备预防和/或治疗阿片类毒品成瘾药物中的应用和药物及制备方法 |
| CN108159031A (zh) * | 2018-01-24 | 2018-06-15 | 昆明理工大学 | 二甲双胍在制备预防和/或治疗苯丙胺类毒品成瘾药物中的应用和药物及制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003026667A1 (en) * | 2001-09-24 | 2003-04-03 | Synaptic Pharmaceutical Corporation | Quinazolino- and quinolino- guanidines as ligands for the neurop eptide ff (npff) receptors |
| WO2003026657A1 (en) * | 2001-09-24 | 2003-04-03 | Synaptic Pharmaceutical Corporation | Compounds for the treatment of pain |
| US20030139431A1 (en) * | 2001-09-24 | 2003-07-24 | Kawakami Joel K. | Guanidines which are agonist/antagonist ligands for neuropeptide FF (NPFF) receptors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3505327A (en) | 1967-08-07 | 1970-04-07 | American Cyanamid Co | Tetrahydroquinoxalinyl phosphates or thiophosphates |
| BE795257A (fr) | 1972-02-10 | 1973-08-09 | Thomae Gmbh Dr K | Nouveaux oxazols |
| DE3334455A1 (de) * | 1983-03-04 | 1984-09-06 | Bayer Ag, 5090 Leverkusen | Guanidin - derivate |
-
2004
- 2004-09-03 US US10/570,517 patent/US7544691B2/en not_active Expired - Fee Related
- 2004-09-03 AU AU2004270304A patent/AU2004270304A1/en not_active Abandoned
- 2004-09-03 WO PCT/CH2004/000556 patent/WO2005023781A1/de not_active Ceased
- 2004-09-03 AT AT04761896T patent/ATE388943T1/de not_active IP Right Cessation
- 2004-09-03 KR KR1020067004345A patent/KR20060064065A/ko not_active Withdrawn
- 2004-09-03 EP EP04761896A patent/EP1663993B1/de not_active Expired - Lifetime
- 2004-09-03 BR BRPI0414103-2A patent/BRPI0414103A/pt not_active IP Right Cessation
- 2004-09-03 RU RU2006110738/04A patent/RU2006110738A/ru not_active Application Discontinuation
- 2004-09-03 CN CN2004800253298A patent/CN1845907B/zh not_active Expired - Fee Related
- 2004-09-03 JP JP2006525025A patent/JP2007504176A/ja active Pending
- 2004-09-03 DE DE502004006515T patent/DE502004006515D1/de not_active Expired - Lifetime
- 2004-09-03 ES ES04761896T patent/ES2300807T3/es not_active Expired - Lifetime
- 2004-09-03 CA CA002536927A patent/CA2536927A1/en not_active Abandoned
- 2004-09-03 PL PL04761896T patent/PL1663993T3/pl unknown
-
2006
- 2006-02-21 IL IL173853A patent/IL173853A0/en unknown
- 2006-04-04 NO NO20061531A patent/NO20061531L/no not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003026667A1 (en) * | 2001-09-24 | 2003-04-03 | Synaptic Pharmaceutical Corporation | Quinazolino- and quinolino- guanidines as ligands for the neurop eptide ff (npff) receptors |
| WO2003026657A1 (en) * | 2001-09-24 | 2003-04-03 | Synaptic Pharmaceutical Corporation | Compounds for the treatment of pain |
| US20030139431A1 (en) * | 2001-09-24 | 2003-07-24 | Kawakami Joel K. | Guanidines which are agonist/antagonist ligands for neuropeptide FF (NPFF) receptors |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013515728A (ja) * | 2009-12-24 | 2013-05-09 | ノボマー， インコーポレイテッド | 多環式グアニジン化合物の合成のための方法 |
| WO2015002150A1 (ja) | 2013-07-03 | 2015-01-08 | 株式会社新日本科学 | 新規化合物，有機カチオントランスポーター３の検出剤及び活性阻害剤 |
| US9745274B2 (en) | 2013-07-03 | 2017-08-29 | Shin Nippon Biomedical Laboratories, Ltd. | Compound, organic cation transporter 3 detection agent, and organic cation transporter 3 activity inhibitor |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1845907B (zh) | 2010-07-28 |
| EP1663993A1 (de) | 2006-06-07 |
| US7544691B2 (en) | 2009-06-09 |
| BRPI0414103A (pt) | 2006-10-31 |
| KR20060064065A (ko) | 2006-06-12 |
| DE502004006515D1 (en) | 2008-04-24 |
| AU2004270304A1 (en) | 2005-03-17 |
| NO20061531L (no) | 2006-04-04 |
| EP1663993B1 (de) | 2008-03-12 |
| IL173853A0 (en) | 2006-07-05 |
| PL1663993T3 (pl) | 2008-08-29 |
| US20070123510A1 (en) | 2007-05-31 |
| WO2005023781A1 (de) | 2005-03-17 |
| RU2006110738A (ru) | 2007-12-10 |
| CN1845907A (zh) | 2006-10-11 |
| CA2536927A1 (en) | 2005-03-17 |
| ATE388943T1 (de) | 2008-03-15 |
| ES2300807T3 (es) | 2008-06-16 |
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