LT3601B - Derivatives of 2-amino-4-morpholino-6-propyl-1,3,5,-triazine and salts thereof - Google Patents

Derivatives of 2-amino-4-morpholino-6-propyl-1,3,5,-triazine and salts thereof Download PDF

Info

Publication number: LT3601B
Authority: LT; Lithuania
Prior art keywords: propyl; radical; morpholino; alkyl; amino
Prior art date: 1988-08-16

Application number

LTIP829A

Other languages

English (en)

Lithuanian (lt)

Inventor

Eric Cossement

Jean Gobert

Roland Boydens

Jacques Mathieu

Original Assignee

Ucb Sa

Priority date (The priority date 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 date listed.)

1988-08-16

Filing date

1993-08-03

Publication date

1995-12-27

1993-08-03 Application filed by Ucb Sa filed Critical Ucb Sa

1995-02-27 Publication of LTIP829A publication Critical patent/LTIP829A/xx

1995-12-27 Publication of LT3601B publication Critical patent/LT3601B/lt

Links

150000003839 salts Chemical class 0.000 title claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 17
230000001713 cholinergic effect Effects 0.000 claims description 17
GOIPIEMTOZZMNH-UHFFFAOYSA-N 4-morpholin-4-yl-6-propyl-1,3,5-triazin-2-amine Chemical class CCCC1=NC(N)=NC(N2CCOCC2)=N1 GOIPIEMTOZZMNH-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
150000007513 acids Chemical class 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
231100000252 nontoxic Toxicity 0.000 claims description 6
230000003000 nontoxic effect Effects 0.000 claims description 6
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
125000004663 dialkyl amino group Chemical group 0.000 claims description 5
125000005350 hydroxycycloalkyl group Chemical group 0.000 claims description 5
125000006213 aryl hydroxyalkyl group Chemical group 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000005041 acyloxyalkyl group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 72
-1 alkenium Chemical group 0.000 description 57
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
238000012360 testing method Methods 0.000 description 33
241001465754 Metazoa Species 0.000 description 32
229930000680 A04AD01 - Scopolamine Natural products 0.000 description 30
STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 30
STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 30
STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 30
229960002646 scopolamine Drugs 0.000 description 30
239000000243 solution Substances 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
230000000694 effects Effects 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 20
239000000203 mixture Substances 0.000 description 19
238000000034 method Methods 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 15
238000002474 experimental method Methods 0.000 description 15
238000002844 melting Methods 0.000 description 15
230000008018 melting Effects 0.000 description 15
150000003254 radicals Chemical class 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 14
PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 14
229960001697 physostigmine Drugs 0.000 description 14
230000002829 reductive effect Effects 0.000 description 14
238000004458 analytical method Methods 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
238000012549 training Methods 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
239000007928 intraperitoneal injection Substances 0.000 description 10
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
241000700159 Rattus Species 0.000 description 8
210000003296 saliva Anatomy 0.000 description 8
238000001228 spectrum Methods 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
239000000812 cholinergic antagonist Substances 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
231100000636 lethal dose Toxicity 0.000 description 5
238000005259 measurement Methods 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
230000002093 peripheral effect Effects 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
210000002966 serum Anatomy 0.000 description 5
239000007858 starting material Substances 0.000 description 5
GWZHFTVSEHQITC-UHFFFAOYSA-N 2-[(4-chloro-6-propyl-1,3,5-triazin-2-yl)amino]ethanol Chemical compound CCCC1=NC(Cl)=NC(NCCO)=N1 GWZHFTVSEHQITC-UHFFFAOYSA-N 0.000 description 4
NERMEVBNTXXDNG-UHFFFAOYSA-N 2-[(4-morpholin-4-yl-6-propyl-1,3,5-triazin-2-yl)amino]ethanol Chemical compound CCCC1=NC(NCCO)=NC(N2CCOCC2)=N1 NERMEVBNTXXDNG-UHFFFAOYSA-N 0.000 description 4
208000000044 Amnesia Diseases 0.000 description 4
208000031091 Amnestic disease Diseases 0.000 description 4
206010012289 Dementia Diseases 0.000 description 4
206010044565 Tremor Diseases 0.000 description 4
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 4
HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000011707 mineral Substances 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
230000008569 process Effects 0.000 description 4
230000028327 secretion Effects 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
VGVDKHQHGQNHLT-UHFFFAOYSA-N 2,4-dichloro-6-propyl-1,3,5-triazine Chemical compound CCCC1=NC(Cl)=NC(Cl)=N1 VGVDKHQHGQNHLT-UHFFFAOYSA-N 0.000 description 3
UWJDXCSJNFALGW-UHFFFAOYSA-N 4-chloro-6-propyl-1,3,5-triazin-2-amine Chemical compound CCCC1=NC(N)=NC(Cl)=N1 UWJDXCSJNFALGW-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
230000009471 action Effects 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
230000006986 amnesia Effects 0.000 description 3
239000003480 eluent Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
238000007912 intraperitoneal administration Methods 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
YEFBYCDRWIBCPG-UHFFFAOYSA-N 1,1-dimethyl-3-(4-morpholin-4-yl-6-propyl-1,3,5-triazin-2-yl)urea Chemical compound CCCC1=NC(NC(=O)N(C)C)=NC(N2CCOCC2)=N1 YEFBYCDRWIBCPG-UHFFFAOYSA-N 0.000 description 2
LUOSAHLDFNGBQX-UHFFFAOYSA-N 4-(4-propyl-1,3,5-triazin-2-yl)morpholine Chemical class CCCC1=NC=NC(N2CCOCC2)=N1 LUOSAHLDFNGBQX-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
DNJFTXKSFAMXQF-UHFFFAOYSA-N Arecaidine Chemical compound CN1CCC=C(C(O)=O)C1 DNJFTXKSFAMXQF-UHFFFAOYSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
208000026139 Memory disease Diseases 0.000 description 2
229940121948 Muscarinic receptor antagonist Drugs 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
206010039424 Salivary hypersecretion Diseases 0.000 description 2
230000004913 activation Effects 0.000 description 2
230000032683 aging Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
230000007423 decrease Effects 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
235000013305 food Nutrition 0.000 description 2
210000001061 forehead Anatomy 0.000 description 2
244000144993 groups of animals Species 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000003902 lesion Effects 0.000 description 2
230000000670 limiting effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000012423 maintenance Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000000902 placebo Substances 0.000 description 2
229940068196 placebo Drugs 0.000 description 2
238000004445 quantitative analysis Methods 0.000 description 2
230000011514 reflex Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
208000026451 salivation Diseases 0.000 description 2
239000000829 suppository Substances 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
SLTBMTIRYMGWLX-XMMPIXPASA-N (2r)-2-[(4-chloroanilino)carbamoylamino]-3-(1h-indol-3-yl)-n-(2-phenylethyl)propanamide Chemical compound C1=CC(Cl)=CC=C1NNC(=O)N[C@@H](C(=O)NCCC=1C=CC=CC=1)CC1=CNC2=CC=CC=C12 SLTBMTIRYMGWLX-XMMPIXPASA-N 0.000 description 1
IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
IWZBGBLNAFYBMG-UHFFFAOYSA-N (4-morpholin-4-yl-6-propyl-1,3,5-triazin-2-yl) N-phenylcarbamate Chemical compound O1CCN(CC1)C1=NC(=NC(=N1)CCC)OC(NC1=CC=CC=C1)=O IWZBGBLNAFYBMG-UHFFFAOYSA-N 0.000 description 1
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical class NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 1
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
JBZKXLKJDXNOES-UHFFFAOYSA-N 2-[(4-morpholin-4-yl-6-propyl-1,3,5-triazin-2-yl)amino]ethyl phenyl carbonate Chemical compound N=1C(N2CCOCC2)=NC(CCC)=NC=1NCCOC(=O)OC1=CC=CC=C1 JBZKXLKJDXNOES-UHFFFAOYSA-N 0.000 description 1
IZWZQJUDLYIMLI-UHFFFAOYSA-N 2-[acetyl-(4-morpholin-4-yl-6-propyl-1,3,5-triazin-2-yl)amino]ethyl acetate Chemical compound CCCC1=NC(N(CCOC(C)=O)C(C)=O)=NC(N2CCOCC2)=N1 IZWZQJUDLYIMLI-UHFFFAOYSA-N 0.000 description 1
XVEPBYZYNPTQFF-UHFFFAOYSA-N 2-aminoethanol;hypochlorous acid Chemical compound ClO.NCCO XVEPBYZYNPTQFF-UHFFFAOYSA-N 0.000 description 1
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 description 1
HNFMVVHMKGFCMB-UHFFFAOYSA-N 3-[3-[4-(1-aminocyclobutyl)phenyl]-5-phenylimidazo[4,5-b]pyridin-2-yl]pyridin-2-amine Chemical compound NC1=NC=CC=C1C1=NC2=CC=C(C=3C=CC=CC=3)N=C2N1C1=CC=C(C2(N)CCC2)C=C1 HNFMVVHMKGFCMB-UHFFFAOYSA-N 0.000 description 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
VBNOJXKRMKUFPO-UHFFFAOYSA-N 4-(4-chloro-6-propyl-1,3,5-triazin-2-yl)morpholine Chemical compound CCCC1=NC(Cl)=NC(N2CCOCC2)=N1 VBNOJXKRMKUFPO-UHFFFAOYSA-N 0.000 description 1
GRJZBGMZDLOHRG-UHFFFAOYSA-N 4-chloro-n-methyl-6-propyl-1,3,5-triazin-2-amine Chemical compound CCCC1=NC(Cl)=NC(NC)=N1 GRJZBGMZDLOHRG-UHFFFAOYSA-N 0.000 description 1
102000012440 Acetylcholinesterase Human genes 0.000 description 1
108010022752 Acetylcholinesterase Proteins 0.000 description 1
229910002012 Aerosil® Inorganic materials 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
PLBVJJMEICHJAG-UHFFFAOYSA-N ClO.N1CCOCC1 Chemical compound ClO.N1CCOCC1 PLBVJJMEICHJAG-UHFFFAOYSA-N 0.000 description 1
206010052804 Drug tolerance Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
238000011785 NMRI mouse Methods 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
241001494479 Pecora Species 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229940022698 acetylcholinesterase Drugs 0.000 description 1
239000003470 adrenal cortex hormone Substances 0.000 description 1
230000001780 adrenocortical effect Effects 0.000 description 1
125000004171 alkoxy aryl group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000003109 amnesic effect Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229960004543 anhydrous citric acid Drugs 0.000 description 1
230000001078 anti-cholinergic effect Effects 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000006399 behavior Effects 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
230000006949 cholinergic function Effects 0.000 description 1
230000000718 cholinopositive effect Effects 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
230000001149 cognitive effect Effects 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940126086 compound 21 Drugs 0.000 description 1
229940126208 compound 22 Drugs 0.000 description 1
229940125807 compound 37 Drugs 0.000 description 1
229940126540 compound 41 Drugs 0.000 description 1
229940125936 compound 42 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
230000004064 dysfunction Effects 0.000 description 1
238000000537 electroencephalography Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000009408 flooring Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
238000002695 general anesthesia Methods 0.000 description 1
230000026781 habituation Effects 0.000 description 1
125000003106 haloaryl group Chemical group 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
BGMIRDHBNWQSGE-UHFFFAOYSA-N hypochlorous acid;pyridine Chemical compound ClO.C1=CC=NC=C1 BGMIRDHBNWQSGE-UHFFFAOYSA-N 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
235000019988 mead Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
206010027175 memory impairment Diseases 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
DUEIIRPCSTVNKO-UHFFFAOYSA-N n-(2-methoxyethyl)-4-morpholin-4-yl-6-propyl-1,3,5-triazin-2-amine Chemical compound CCCC1=NC(NCCOC)=NC(N2CCOCC2)=N1 DUEIIRPCSTVNKO-UHFFFAOYSA-N 0.000 description 1
FWQLJUGGYCPTMQ-UHFFFAOYSA-N n-(4-morpholin-4-yl-6-propyl-1,3,5-triazin-2-yl)acetamide Chemical compound CCCC1=NC(NC(C)=O)=NC(N2CCOCC2)=N1 FWQLJUGGYCPTMQ-UHFFFAOYSA-N 0.000 description 1
DEEJUOIMQOMMJA-UHFFFAOYSA-N n-methyl-4-morpholin-4-yl-6-propyl-1,3,5-triazin-2-amine Chemical compound CCCC1=NC(NC)=NC(N2CCOCC2)=N1 DEEJUOIMQOMMJA-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000007170 pathology Effects 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/08—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Ophthalmology & Optometry (AREA)
Neurosurgery (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Cosmetics (AREA)

LTIP829A 1988-08-16 1993-08-03 Derivatives of 2-amino-4-morpholino-6-propyl-1,3,5,-triazine and salts thereof LT3601B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888819493A GB8819493D0 (en)	1988-08-16	1988-08-16	2-amino-4-morpholino-6-propyl-1 3 5-triazines

Publications (2)

Publication Number	Publication Date
LTIP829A LTIP829A (en)	1995-02-27
LT3601B true LT3601B (en)	1995-12-27

Family

ID=10642235

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP829A LT3601B (en)	1988-08-16	1993-08-03	Derivatives of 2-amino-4-morpholino-6-propyl-1,3,5,-triazine and salts thereof

Country Status (28)

Country	Link
US (1)	US4956367A (de)
EP (1)	EP0356413B1 (de)
JP (1)	JPH02108675A (de)
KR (1)	KR0136108B1 (de)
AT (1)	ATE72241T1 (de)
AU (1)	AU614247B2 (de)
CA (1)	CA1317944C (de)
CY (1)	CY1709A (de)
DE (1)	DE68900794D1 (de)
DK (1)	DK171698B1 (de)
ES (1)	ES2038849T3 (de)
FI (1)	FI102065B1 (de)
GB (1)	GB8819493D0 (de)
GR (1)	GR3004267T3 (de)
HK (1)	HK95693A (de)
HU (1)	HUT58087A (de)
IE (1)	IE61205B1 (de)
IL (1)	IL91243A (de)
LT (1)	LT3601B (de)
MY (1)	MY105008A (de)
NO (1)	NO179206C (de)
NZ (1)	NZ230290A (de)
PL (2)	PL161591B1 (de)
PT (1)	PT91438B (de)
RU (3)	RU1806142C (de)
SG (1)	SG27893G (de)
UA (1)	UA11064A (de)
ZA (1)	ZA896222B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9024617D0 (en) *	1989-12-05	1991-01-02	Ici Plc	Heterocyclic compounds
GB9008818D0 (en) *	1990-04-19	1990-06-13	Ici Plc	Amine derivatives
IT1240690B (it) *	1990-04-30	1993-12-17	Ciba Geigy Ag	Composti piperdin-triazinici atti all'impiego come stabilizzanti per materiali organici
GB9116039D0 (en) *	1991-07-25	1991-09-11	Ucb Sa	Substituted cyclopropylamino-1,3,5-triazines

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4969688A (de)	1972-11-02	1974-07-05

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3549755A (en) *	1968-03-27	1970-12-22	Shell Oil Co	Use of 2-trichloromethyl-4-morpholinoor piperazino-6-substituted-s-triazines for inducing depressant effects in animals
FR2262512A1 (en) *	1974-03-01	1975-09-26	Synthelabo	2,4,6-Tri-substd. -1,3,5-triazines - with analgesic and psychotropic activity

1988
- 1988-08-16 GB GB888819493A patent/GB8819493D0/en active Pending
1989
- 1989-07-28 EP EP89870120A patent/EP0356413B1/de not_active Expired - Lifetime
- 1989-07-28 AT AT89870120T patent/ATE72241T1/de not_active IP Right Cessation
- 1989-07-28 DE DE8989870120T patent/DE68900794D1/de not_active Expired - Lifetime
- 1989-07-28 ES ES198989870120T patent/ES2038849T3/es not_active Expired - Lifetime
- 1989-08-07 FI FI893714A patent/FI102065B1/fi not_active IP Right Cessation
- 1989-08-08 US US07/390,878 patent/US4956367A/en not_active Expired - Fee Related
- 1989-08-08 IL IL9124389A patent/IL91243A/en not_active IP Right Cessation
- 1989-08-09 MY MYPI89001088A patent/MY105008A/en unknown
- 1989-08-09 CA CA000607834A patent/CA1317944C/en not_active Expired - Fee Related
- 1989-08-11 PT PT91438A patent/PT91438B/pt not_active IP Right Cessation
- 1989-08-11 PL PL89283603A patent/PL161591B1/pl unknown
- 1989-08-11 PL PL1989281021A patent/PL161161B1/pl unknown
- 1989-08-14 DK DK398189A patent/DK171698B1/da active
- 1989-08-14 NZ NZ230290A patent/NZ230290A/xx unknown
- 1989-08-15 JP JP1210547A patent/JPH02108675A/ja active Pending
- 1989-08-15 RU SU894614758A patent/RU1806142C/ru active
- 1989-08-15 NO NO893279A patent/NO179206C/no unknown
- 1989-08-15 IE IE261989A patent/IE61205B1/en not_active IP Right Cessation
- 1989-08-15 AU AU39917/89A patent/AU614247B2/en not_active Ceased
- 1989-08-15 ZA ZA896222A patent/ZA896222B/xx unknown
- 1989-08-15 HU HU894192A patent/HUT58087A/hu unknown
- 1989-08-16 KR KR1019890011696A patent/KR0136108B1/ko not_active Expired - Fee Related
- 1989-12-21 UA UA4742645A patent/UA11064A/uk unknown
- 1989-12-21 RU SU894742645A patent/RU1822403C/ru active
1990
- 1990-08-20 RU SU904830673A patent/RU1838312C/ru active
1992
- 1992-04-02 GR GR920400622T patent/GR3004267T3/el unknown
1993
- 1993-03-16 SG SG278/93A patent/SG27893G/en unknown
- 1993-08-03 LT LTIP829A patent/LT3601B/lt not_active IP Right Cessation
- 1993-09-16 HK HK956/93A patent/HK95693A/xx not_active IP Right Cessation
1994
- 1994-01-14 CY CY170994A patent/CY1709A/xx unknown

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4969688A (de)	1972-11-02	1974-07-05

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ALAIN PLATEL, ROGER D. PORSOLT: "Habituation of exploratory activity in mice: A screening test for memory enhancing drugs", PSYCHOPHARMACOLOGY, 1982, pages 346 - 352
GLICK, S.D.; ZIMMERBERG, B.: "Amnesic effects of scopolamine", BEHAVIORAL BIOLOGY, 1972, pages 245 - 254
P.ETEVENON: "Elektroencefalografija su ESM. Kiekybinė analizė ir statistika."
U. SCHINDLER, D. K. RUSH ANDS. FIELDING: "Nootropic drugs: Animal models for studying effects on cognition", DRUG DEVELOPMENT RESEARC, 1984, pages 567 - 576, XP001050360, DOI: doi:10.1002/ddr.430040510

Also Published As

Publication number	Publication date
IE61205B1 (en)	1994-10-19
NO893279L (no)	1990-02-19
IL91243A (en)	1995-05-26
HUT58087A (en)	1992-01-28
JPH02108675A (ja)	1990-04-20
GR3004267T3 (de)	1993-03-31
MY105008A (en)	1994-07-30
CY1709A (en)	1994-01-14
GB8819493D0 (en)	1988-09-21
NO179206C (no)	1996-08-28
US4956367A (en)	1990-09-11
CA1317944C (en)	1993-05-18
RU1806142C (ru)	1993-03-30
FI893714A7 (fi)	1990-02-17
EP0356413A1 (de)	1990-02-28
UA11064A (uk)	1996-12-25
AU3991789A (en)	1990-04-05
ES2038849T3 (es)	1993-08-01
DE68900794D1 (en)	1992-03-12
KR0136108B1 (ko)	1998-04-25
AU614247B2 (en)	1991-08-22
NZ230290A (en)	1991-10-25
SG27893G (en)	1993-06-25
PL161161B1 (pl)	1993-05-31
FI102065B (fi)	1998-10-15
NO179206B (no)	1996-05-20
ZA896222B (en)	1990-05-30
IL91243A0 (en)	1990-03-19
DK398189D0 (da)	1989-08-14
RU1822403C (ru)	1993-06-15
FI102065B1 (fi)	1998-10-15
ATE72241T1 (de)	1992-02-15
LTIP829A (en)	1995-02-27
PT91438B (pt)	1995-05-04
HK95693A (en)	1993-09-24
DK398189A (da)	1990-02-17
EP0356413B1 (de)	1992-01-29
FI893714A0 (fi)	1989-08-07
KR900003165A (ko)	1990-03-23
PL161591B1 (pl)	1993-07-30
IE892619L (en)	1990-02-16
NO893279D0 (no)	1989-08-15
DK171698B1 (da)	1997-03-24
RU1838312C (ru)	1993-08-30
PT91438A (pt)	1990-03-08

Legal Events

Date	Code	Title	Description
2000-03-27	MM9A	Lapsed patents	Effective date: 19990803

Publication	Publication Date	Title
RU2095353C1 (ru)	1997-11-10	Замещенные циклопропиламино-1,3,5-триазины, их оптические изомеры, рацемические смеси или их соли присоединения нетоксичных фармацевтически приемлемых кислот, проявляющие фармакологическую активность, способ их получения и фармацевтическая композиция на их основе
DE69532811T2 (de)	2005-03-17	Heterocyclische Derivative und Arzneimittel
Jacobsen et al.	1990	Novel 21-aminosteroids that inhibit iron-dependent lipid peroxidation and protect against central nervous system trauma
KR0137660B1 (ko)	1998-05-15	노화와 치매증에 관련된 인식 및 행동장애 치료제
KR100263495B1 (ko)	2000-11-01	5-ht1a 및 5-ht2 길항제로서의 벤즈이미다졸론 유도체,이의 제조방법 및 이를 함유하는 약제학적 조성물
SK281211B6 (sk)	2001-01-18	1,5-benzodiazepínové deriváty, spôsob ich výroby, použitie a farmaceutické prostriedky s ich obsahom
PT96228A (pt)	1992-09-30	Processo para a preparacao de composicoes de analogos da benzodiazepina para o tratamento da reaccao de panico e para inducao directa da analgesia e respectivos metodos de tratamento
FR2804113A1 (fr)	2001-07-27	Derives animes de dihydro-1,3,5-triazine et leurs applications en therapeutique
CS240954B2 (en)	1986-03-13	Preparation method of 1,2-dihydropyridines
PL183837B1 (pl)	2002-07-31	Pochodna difenylometylenopiperydyny, sposób wytwarzania pochodnej difenylometylenopiperydyny, kompozycja farmaceutyczna i zastosowanie pochodnej difenylometylenopiperydyny
LT3601B (en)	1995-12-27	Derivatives of 2-amino-4-morpholino-6-propyl-1,3,5,-triazine and salts thereof
JPH0723365B2 (ja)	1995-03-15	フエノキシアルキルまたはチオフエノキシアルキル側鎖を有する新規ピペラジンカルボキシアミド化合物
HUT70148A (en)	1995-09-28	Isoquinolone derivatives as techykinin receptor antagonists, process for producing thereof and pharmaceutical compositions comprising them
HU222246B1 (hu)	2003-05-28	Piperidin-karbaminsav-származékok, eljárás előállításukra és az ezeket tartalmazó gyógyászati készítmények
EP0197386A1 (de)	1986-10-15	2-(Sulfamylsubstituierte) Derivate von 6-Nitrobenzoesäure, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen