IL91244A - Pharmaceutical preparations containing 2-amino-4-morpholino-6-profile-1,3,5-triazines - Google Patents

Pharmaceutical preparations containing 2-amino-4-morpholino-6-profile-1,3,5-triazines

Info

Publication number: IL91244A
Authority: IL; Israel
Prior art keywords: morpholino; amino; compound; formula; propyl
Prior art date: 1988-08-16

Application number

IL9124489A

Other languages

English (en)

Hebrew (he)

Other versions

IL91244A0 (en

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

1989-08-08

Publication date

1994-07-31

1989-08-08 Application filed by Ucb Sa filed Critical Ucb Sa

1990-03-19 Publication of IL91244A0 publication Critical patent/IL91244A0/xx

1994-07-31 Publication of IL91244A publication Critical patent/IL91244A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 8
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 title abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
230000032683 aging Effects 0.000 claims abstract description 9
206010012289 Dementia Diseases 0.000 claims abstract description 8
230000003542 behavioural effect Effects 0.000 claims abstract description 8
230000001149 cognitive effect Effects 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 7
208000011580 syndromic disease Diseases 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 70
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
231100000252 nontoxic Toxicity 0.000 claims description 7
230000003000 nontoxic effect Effects 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 4
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
-1 halogenoaryl Chemical group 0.000 abstract description 15
238000000034 method Methods 0.000 abstract description 15
208000024827 Alzheimer disease Diseases 0.000 abstract description 4
206010039966 Senile dementia Diseases 0.000 abstract description 3
125000003118 aryl group Chemical group 0.000 abstract description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
229910052739 hydrogen Inorganic materials 0.000 abstract 3
239000001257 hydrogen Substances 0.000 abstract 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 2
125000003710 aryl alkyl group Chemical group 0.000 abstract 2
125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
101100295738 Gallus gallus COR3 gene Proteins 0.000 abstract 1
125000005041 acyloxyalkyl group Chemical group 0.000 abstract 1
125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
125000004171 alkoxy aryl group Chemical group 0.000 abstract 1
125000002877 alkyl aryl group Chemical group 0.000 abstract 1
125000006213 aryl hydroxyalkyl group Chemical group 0.000 abstract 1
125000004104 aryloxy group Chemical group 0.000 abstract 1
125000004663 dialkyl amino group Chemical group 0.000 abstract 1
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
125000005350 hydroxycycloalkyl group Chemical group 0.000 abstract 1
241001465754 Metazoa Species 0.000 description 36
229930000680 A04AD01 - Scopolamine Natural products 0.000 description 32
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 32
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 32
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 32
229960002646 scopolamine Drugs 0.000 description 32
238000012360 testing method Methods 0.000 description 23
230000000694 effects Effects 0.000 description 22
230000001713 cholinergic effect Effects 0.000 description 15
PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 13
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 13
229960001697 physostigmine Drugs 0.000 description 13
239000000243 solution Substances 0.000 description 13
239000007928 intraperitoneal injection Substances 0.000 description 12
RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 11
241000700159 Rattus Species 0.000 description 10
230000013016 learning Effects 0.000 description 10
238000002474 experimental method Methods 0.000 description 9
208000035475 disorder Diseases 0.000 description 8
238000001228 spectrum Methods 0.000 description 8
HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
206010044565 Tremor Diseases 0.000 description 6
239000012266 salt solution Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000000812 cholinergic antagonist Substances 0.000 description 5
208000013403 hyperactivity Diseases 0.000 description 5
230000002093 peripheral effect Effects 0.000 description 5
210000003296 saliva Anatomy 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000003981 vehicle Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
231100000636 lethal dose Toxicity 0.000 description 4
238000005259 measurement Methods 0.000 description 4
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
230000003389 potentiating effect Effects 0.000 description 4
230000009467 reduction Effects 0.000 description 4
239000007858 starting material Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
208000000044 Amnesia Diseases 0.000 description 3
208000031091 Amnestic disease Diseases 0.000 description 3
239000001828 Gelatine Substances 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
230000006986 amnesia Effects 0.000 description 3
230000003109 amnesic effect Effects 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000003086 colorant Substances 0.000 description 3
229940125782 compound 2 Drugs 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
238000007912 intraperitoneal administration Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229940068918 polyethylene glycol 400 Drugs 0.000 description 3
230000008569 process Effects 0.000 description 3
230000000750 progressive effect Effects 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000004913 activation Effects 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
235000013305 food Nutrition 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
244000144993 groups of animals Species 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
229960002216 methylparaben Drugs 0.000 description 2
239000000902 placebo Substances 0.000 description 2
229940068196 placebo Drugs 0.000 description 2
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
230000011514 reflex Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
235000020374 simple syrup Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000012453 sprague-dawley rat model Methods 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
231100000816 toxic dose Toxicity 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical class NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 1
QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
QPJGOZXYYJDTID-UHFFFAOYSA-N 4-(4-methyl-6-morpholin-4-yl-1,3,5-triazin-2-yl)morpholine Chemical group N=1C(C)=NC(N2CCOCC2)=NC=1N1CCOCC1 QPJGOZXYYJDTID-UHFFFAOYSA-N 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
102000012440 Acetylcholinesterase Human genes 0.000 description 1
108010022752 Acetylcholinesterase Proteins 0.000 description 1
208000031872 Body Remains Diseases 0.000 description 1
206010052804 Drug tolerance Diseases 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
238000011785 NMRI mouse Methods 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
206010039424 Salivary hypersecretion Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
229940022698 acetylcholinesterase Drugs 0.000 description 1
230000009471 action Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000001078 anti-cholinergic effect Effects 0.000 description 1
230000002082 anti-convulsion Effects 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
230000000141 anti-hypoxic effect Effects 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
239000003416 antiarrhythmic agent Substances 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000000064 cholinergic agonist 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
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000006735 deficit Effects 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
239000003527 fibrinolytic agent Substances 0.000 description 1
230000003480 fibrinolytic effect Effects 0.000 description 1
230000006870 function Effects 0.000 description 1
238000002695 general anesthesia Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003862 glucocorticoid Substances 0.000 description 1
230000026781 habituation Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
230000001900 immune effect Effects 0.000 description 1
230000006872 improvement Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 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
238000007911 parenteral administration Methods 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 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
RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
238000004445 quantitative analysis Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
NXLOLUFNDSBYTP-UHFFFAOYSA-N retene Chemical compound C1=CC=C2C3=CC=C(C(C)C)C=C3C=CC2=C1C NXLOLUFNDSBYTP-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
208000026451 salivation Diseases 0.000 description 1
230000028327 secretion Effects 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
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238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
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230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
210000001364 upper extremity Anatomy 0.000 description 1

Classifications

- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids

Landscapes

Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Neurosurgery (AREA)
Bioinformatics & Cheminformatics (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Plant Substances (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

IL9124489A 1988-08-16 1989-08-08 Pharmaceutical preparations containing 2-amino-4-morpholino-6-profile-1,3,5-triazines IL91244A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888819494A GB8819494D0 (en)	1988-08-16	1988-08-16	Use of 2-amino-4-morpholino-6-propyl-1 3 5-triazines for preparation of psychotropic medicaments

Publications (2)

Publication Number	Publication Date
IL91244A0 IL91244A0 (en)	1990-03-19
IL91244A true IL91244A (en)	1994-07-31

Family

ID=10642236

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9124489A IL91244A (en)	1988-08-16	1989-08-08	Pharmaceutical preparations containing 2-amino-4-morpholino-6-profile-1,3,5-triazines

Country Status (15)

Country	Link
US (1)	US4956363A (de)
EP (1)	EP0356412B1 (de)
JP (1)	JPH02108676A (de)
KR (1)	KR0137660B1 (de)
AT (1)	ATE75942T1 (de)
AU (1)	AU616140B2 (de)
CA (1)	CA1329772C (de)
DE (1)	DE68901511D1 (de)
DK (1)	DK398289A (de)
GB (1)	GB8819494D0 (de)
IE (1)	IE61828B1 (de)
IL (1)	IL91244A (de)
MY (1)	MY104150A (de)
PH (1)	PH26119A (de)
ZA (1)	ZA896223B (de)

Families Citing this family (15)

* 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
FR2665636B1 (fr) *	1990-08-10	1994-10-07	Adir	Utilisation d'un derive de la trimethyl-1,3,7 xanthine pour le traitement des troubles de la memoire, des troubles intellectuels de la senescence et de la maladie d'alzheimer.
GB9116039D0 (en) *	1991-07-25	1991-09-11	Ucb Sa	Substituted cyclopropylamino-1,3,5-triazines
DE19531084A1 (de) *	1995-08-24	1997-02-27	Hoechst Schering Agrevo Gmbh	2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
EP1185528A4 (de) *	1999-06-17	2003-03-26	Shionogi Biores Corp	Inhibitoren der il-12 herstellung
US20060004005A1 (en) *	2003-09-25	2006-01-05	Sattigeri Viswajanani J	Triazines derivatives as cell adhesion inhibitors
WO2006053227A2 (en) *	2004-11-10	2006-05-18	Synta Pharmaceuticals Corp.	Il-12 modulatory compounds
EP2389187B1 (de)	2009-01-20	2016-11-16	Los Angeles Biomedical Research Institute at Harbor-UCLA Medical Center	Sorbin- und benzoesäure und derivate daraus zur verstärkung der wirkung eines neuropharmakons
WO2016204988A1 (en) *	2015-06-18	2016-12-22	The United States Of America, As Represented By The Secretary, Department Of Health And Human Services	Autophagy modulators for treating neurodegenerative diseases
US10815184B2 (en)	2016-06-13	2020-10-27	Syneurx International (Taiwan) Corp.	Co-crystals of lithium benzoate and uses thereof
US11008277B2 (en)	2016-06-13	2021-05-18	Syneurx International (Taiwan) Corp.	Co-crystals of sodium benzoate and uses thereof
US10336679B2 (en)	2016-10-24	2019-07-02	Syneurx International (Taiwan) Corp.	Polymorphic forms of sodium benzoate and uses thereof
US11369579B2 (en)	2016-10-24	2022-06-28	Syneurx International (Taiwan) Corp.	Polymorphic forms of sodium benzoate and uses thereof
US10098861B1 (en)	2017-10-24	2018-10-16	Syneurx International (Taiwan) Corp.	Pharmaceutical composition comprising sodium benzoate compound and clozapine, and uses thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3549757A (en) *	1968-03-27	1970-12-22	Shell Oil Co	Use of 2-morpholino - 4 - amino-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 GB888819494A patent/GB8819494D0/en active Pending
1989
- 1989-07-28 DE DE8989870119T patent/DE68901511D1/de not_active Expired - Lifetime
- 1989-07-28 EP EP89870119A patent/EP0356412B1/de not_active Expired - Lifetime
- 1989-07-28 AT AT89870119T patent/ATE75942T1/de not_active IP Right Cessation
- 1989-08-08 IL IL9124489A patent/IL91244A/en not_active IP Right Cessation
- 1989-08-08 US US07/309,877 patent/US4956363A/en not_active Expired - Fee Related
- 1989-08-09 MY MYPI89001087A patent/MY104150A/en unknown
- 1989-08-09 CA CA000607833A patent/CA1329772C/en not_active Expired - Fee Related
- 1989-08-09 PH PH39076A patent/PH26119A/en unknown
- 1989-08-14 DK DK398289A patent/DK398289A/da not_active Application Discontinuation
- 1989-08-15 JP JP1210548A patent/JPH02108676A/ja active Pending
- 1989-08-15 AU AU39918/89A patent/AU616140B2/en not_active Ceased
- 1989-08-15 IE IE262089A patent/IE61828B1/en not_active IP Right Cessation
- 1989-08-15 ZA ZA896223A patent/ZA896223B/xx unknown
- 1989-08-16 KR KR1019890011697A patent/KR0137660B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
KR900002780A (ko)	1990-03-23
ATE75942T1 (de)	1992-05-15
ZA896223B (en)	1990-05-30
AU3991889A (en)	1990-02-22
JPH02108676A (ja)	1990-04-20
MY104150A (en)	1994-02-28
DK398289D0 (da)	1989-08-14
DE68901511D1 (de)	1992-06-17
DK398289A (da)	1990-02-17
CA1329772C (en)	1994-05-24
EP0356412A1 (de)	1990-02-28
EP0356412B1 (de)	1992-05-13
GB8819494D0 (en)	1988-09-21
IE892620L (en)	1990-02-16
IE61828B1 (en)	1994-11-30
IL91244A0 (en)	1990-03-19
PH26119A (en)	1992-02-24
US4956363A (en)	1990-09-11
KR0137660B1 (ko)	1998-05-15
AU616140B2 (en)	1991-10-17

Legal Events

Date	Code	Title	Description
2000-12-06	RH	Patent void

Publication	Publication Date	Title
IL91244A (en)	1994-07-31	Pharmaceutical preparations containing 2-amino-4-morpholino-6-profile-1,3,5-triazines
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
DE69219394T2 (de)	1997-12-11	Heterozyklische Alkylamide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
SE448730B (sv)	1987-03-16	Nya 1-(4,4-difenylbutyl)piperazin-karboxamider och karbotioamider samt anvendning av dessa foreningar for framstellning av medel for behandling av vissa sjukdomstillstand
SE457081B (sv)	1988-11-28	1,2-diaminocyklobutan-3,4-dioner, foerfarande foer framstaellning av dessa, mellanprodukt och en farmaceutisk komposition
JPS61183223A (ja)	1986-08-15	アリールアミドアザビシクロアルカンを含む記憶増強または記憶欠損矯正用組成物
US4960776A (en)	1990-10-02	4-aryl-N-(alkylaminoalkyl, heterocyclicamino and heterocyclicamino)alkyl)-1-piperazinecarboxamides
RU2021269C1 (ru)	1994-10-15	Пиридил- или пиримидилсодержащие производные пиперазина или 1,4-диазациклогептана или их фармакологически активные кислотно-аддитивные соли, обладающие психотропным действием
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
US3474090A (en)	1969-10-21	3-aminoalkyl-1,3-benzodiazepin-2-ones
RU1822403C (ru)	1993-06-15	Производные 2-амино-4-морфолино-6-пропил-1,3,5,-триазина в виде свободного основани или в виде гидрохлорида, обладающие активностью потенциализации холинэргического эффекта, улучшающего пам ть и способность к учению
US4855308A (en)	1989-08-08	Method of treating senile cognitive decline with N'-substituted aminopyridine adrenergic agents
US5086055A (en)	1992-02-04	Series of 5-[-(4-aryl-1-piperazinyl)alkyl]-2-oxazolidinone derivatives useful in the treatment of allergic conditions
US4540696A (en)	1985-09-10	1-Piperazinyl 4-phenylquinazoline compounds having antidepressant properties and drugs containing same
US3331845A (en)	1967-07-18	1-substituted-4-substituted amino alkylene piperazines
EP0405905B1 (de)	1995-12-06	Verwendung von Isoxazolin-3-one-Derivaten als Antidepressiva
GB2162843A (en)	1986-02-12	Piperazine derivatives
JPS636068B2 (de)	1988-02-08
KR100556559B1 (ko)	2006-03-06	2-(4-(4-(4,5-디클로로-2-메틸이미다졸-1-일)부틸)-1-피페라지닐)-5-플루오로피리미딘, 이것의 제조 방법 및 이것의치료적 용도
IE44696B1 (en)	1982-02-24	Pyrodoxine derivatives
US3398144A (en)	1968-08-20	Substituted 3-amino-2'-hydroxyacrylophenones
US3751414A (en)	1973-08-07	3-substituted derivatives or 1,3(3h)-benzoxazine-2,4-dione
JP3681770B2 (ja)	2005-08-10	老年性痴呆症又はアルツハイマー病治療剤
CZ230893A3 (en)	1994-06-15	Benzindene derivatives
KR910007969B1 (ko)	1991-10-05	새로운 1-피페라진카르복스아마이드 유도체의 제조방법