CA2536927A1 - Guanidine derivatives - Google Patents
Guanidine derivatives Download PDFInfo
- Publication number
- CA2536927A1 CA2536927A1 CA002536927A CA2536927A CA2536927A1 CA 2536927 A1 CA2536927 A1 CA 2536927A1 CA 002536927 A CA002536927 A CA 002536927A CA 2536927 A CA2536927 A CA 2536927A CA 2536927 A1 CA2536927 A1 CA 2536927A1
- Authority
- CA
- Canada
- Prior art keywords
- tetrahydro
- guanidine
- rac
- quinazolin
- methyl
- 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.)
- Abandoned
Links
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 title claims description 9
- 150000002357 guanidines Chemical class 0.000 title claims description 8
- 208000002193 Pain Diseases 0.000 claims abstract description 19
- 238000011282 treatment Methods 0.000 claims abstract description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 230000036407 pain Effects 0.000 claims abstract description 14
- 230000036772 blood pressure Effects 0.000 claims abstract description 7
- 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
- 230000002265 prevention Effects 0.000 claims abstract description 7
- 208000004454 Hyperalgesia Diseases 0.000 claims abstract description 6
- 208000035154 Hyperesthesia Diseases 0.000 claims abstract description 6
- 208000007271 Substance Withdrawal Syndrome Diseases 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
- 230000010656 regulation of insulin secretion Effects 0.000 claims abstract description 6
- 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 5
- 150000004677 hydrates Chemical class 0.000 claims abstract description 4
- 239000002464 receptor antagonist Substances 0.000 claims abstract description 3
- 229940044551 receptor antagonist Drugs 0.000 claims abstract description 3
- -1 furopyrazine Chemical compound 0.000 claims description 170
- 150000001875 compounds Chemical class 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio 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
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 150000002148 esters Chemical class 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
- 102400001095 Neuropeptide FF Human genes 0.000 claims description 9
- 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
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000004391 aryl sulfonyl 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
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 108010055752 phenylalanyl-leucyl-phenylalanyl-glutaminyl-prolyl-glutaminyl-arginyl-phenylalaninamide Proteins 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 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 8
- 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
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 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
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- 229940126601 medicinal product Drugs 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- HWYCFZUSOBOBIN-AQJXLSMYSA-N (2s)-2-[[(2s)-1-[(2s)-5-amino-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-amino-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-3-phenylpropanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]amino]-n-[(2s)-1-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-5-(diaminome Chemical compound C([C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)C1=CC=CC=C1 HWYCFZUSOBOBIN-AQJXLSMYSA-N 0.000 claims description 5
- 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
- 206010057852 Nicotine dependence Diseases 0.000 claims description 5
- 208000025569 Tobacco Use disease Diseases 0.000 claims description 5
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims description 5
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 5
- 150000007514 bases Chemical class 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 230000008030 elimination Effects 0.000 claims description 5
- 238000003379 elimination reaction Methods 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 230000000506 psychotropic effect Effects 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- KRNSYSYRLQDHDK-UHFFFAOYSA-N 6,7-dihydro-5h-cyclopenta[b]pyridine Chemical compound C1=CN=C2CCCC2=C1 KRNSYSYRLQDHDK-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
- 229950010221 alexidine Drugs 0.000 claims description 4
- 125000006193 alkinyl group Chemical group 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
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004446 heteroarylalkyl group Chemical group 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 238000007363 ring formation reaction Methods 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 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
- 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
- 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 group 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 group C1=CN=C2CNNNC2=C1 BHKODZGDVUUACI-UHFFFAOYSA-N 0.000 claims description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound 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 compound 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
- FGFBEHFJSQBISW-UHFFFAOYSA-N 1h-cyclopenta[b]pyridine Chemical compound C1=CNC2=CC=CC2=C1 FGFBEHFJSQBISW-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 compound 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
- 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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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- YKFKEYKJGVSEIX-UHFFFAOYSA-N cyclohexanone, 4-(1,1-dimethylethyl)- Chemical compound CC(C)(C)C1CCC(=O)CC1 YKFKEYKJGVSEIX-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 230000001419 dependent effect Effects 0.000 description 1
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- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
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- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
- JCAKGXYKOIRKMC-UHFFFAOYSA-N guanidine;quinazoline Chemical compound NC(N)=N.N1=CN=CC2=CC=CC=C21 JCAKGXYKOIRKMC-UHFFFAOYSA-N 0.000 description 1
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- QWMUDOFWQWBHFI-UHFFFAOYSA-N hydroxy-imino-diphenoxy-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(=O)(N)OC1=CC=CC=C1 QWMUDOFWQWBHFI-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
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- 238000011534 incubation Methods 0.000 description 1
- 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
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- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
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- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 238000011551 log transformation method Methods 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical class O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 201000005040 opiate dependence Diseases 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
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- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
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- 230000035945 sensitivity Effects 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- FPTVEOPNJVOJBF-UHFFFAOYSA-M sodium;oxolane;hydroxide Chemical compound [OH-].[Na+].C1CCOC1 FPTVEOPNJVOJBF-UHFFFAOYSA-M 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- FTGIVLQZVUPSAJ-UHFFFAOYSA-N tert-butyl 3-acetyl-4-oxopiperidine-1-carboxylate Chemical compound CC(=O)C1CN(C(=O)OC(C)(C)C)CCC1=O FTGIVLQZVUPSAJ-UHFFFAOYSA-N 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Addiction (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Endocrinology (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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH15262003 | 2003-09-05 | ||
| CH1526/03 | 2003-09-05 | ||
| PCT/CH2004/000556 WO2005023781A1 (de) | 2003-09-05 | 2004-09-03 | Guanidinderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2536927A1 true CA2536927A1 (en) | 2005-03-17 |
Family
ID=34230846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002536927A Abandoned CA2536927A1 (en) | 2003-09-05 | 2004-09-03 | Guanidine derivatives |
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) |
Families Citing this family (8)
| 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 |
| EP1578422B1 (en) | 2002-12-20 | 2007-04-11 | NicoNovum AB | A physically and chemically stable nicotine and micorcrystalline cellulose containing particulate material |
| US9402809B2 (en) | 2006-03-16 | 2016-08-02 | Niconovum Usa, Inc. | Snuff composition |
| KR101885503B1 (ko) | 2009-12-24 | 2018-08-07 | 사우디 아람코 테크놀로지스 컴퍼니 | 폴리사이클릭 구아니딘 화합물의 합성방법 |
| 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 |
| JP7153653B2 (ja) | 2017-02-14 | 2022-10-14 | リサーチ トライアングル インスティテュート | プロリン系神経ペプチドｆｆ受容体モジュレーター |
| 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 |
| 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 |
Family Cites Families (6)
| 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 |
| 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 |
| WO2003026667A1 (en) * | 2001-09-24 | 2003-04-03 | Synaptic Pharmaceutical Corporation | Quinazolino- and quinolino- guanidines as ligands for the neurop eptide ff (npff) receptors |
-
2004
- 2004-09-03 CA CA002536927A patent/CA2536927A1/en not_active Abandoned
- 2004-09-03 PL PL04761896T patent/PL1663993T3/pl unknown
- 2004-09-03 DE DE502004006515T patent/DE502004006515D1/de not_active Expired - Lifetime
- 2004-09-03 BR BRPI0414103-2A patent/BRPI0414103A/pt not_active IP Right Cessation
- 2004-09-03 AU AU2004270304A patent/AU2004270304A1/en not_active Abandoned
- 2004-09-03 ES ES04761896T patent/ES2300807T3/es not_active Expired - Lifetime
- 2004-09-03 WO PCT/CH2004/000556 patent/WO2005023781A1/de not_active Ceased
- 2004-09-03 CN CN2004800253298A patent/CN1845907B/zh not_active Expired - Fee Related
- 2004-09-03 AT AT04761896T patent/ATE388943T1/de not_active IP Right Cessation
- 2004-09-03 US US10/570,517 patent/US7544691B2/en not_active Expired - Fee Related
- 2004-09-03 JP JP2006525025A patent/JP2007504176A/ja active Pending
- 2004-09-03 RU RU2006110738/04A patent/RU2006110738A/ru not_active Application Discontinuation
- 2004-09-03 KR KR1020067004345A patent/KR20060064065A/ko not_active Withdrawn
- 2004-09-03 EP EP04761896A patent/EP1663993B1/de not_active Expired - Lifetime
-
2006
- 2006-02-21 IL IL173853A patent/IL173853A0/en unknown
- 2006-04-04 NO NO20061531A patent/NO20061531L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL1663993T3 (pl) | 2008-08-29 |
| JP2007504176A (ja) | 2007-03-01 |
| BRPI0414103A (pt) | 2006-10-31 |
| DE502004006515D1 (en) | 2008-04-24 |
| EP1663993A1 (de) | 2006-06-07 |
| EP1663993B1 (de) | 2008-03-12 |
| ATE388943T1 (de) | 2008-03-15 |
| KR20060064065A (ko) | 2006-06-12 |
| US20070123510A1 (en) | 2007-05-31 |
| CN1845907B (zh) | 2010-07-28 |
| NO20061531L (no) | 2006-04-04 |
| WO2005023781A1 (de) | 2005-03-17 |
| ES2300807T3 (es) | 2008-06-16 |
| AU2004270304A1 (en) | 2005-03-17 |
| CN1845907A (zh) | 2006-10-11 |
| IL173853A0 (en) | 2006-07-05 |
| US7544691B2 (en) | 2009-06-09 |
| RU2006110738A (ru) | 2007-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |