SA07280004B1 - ملح سترات من مركب 2- هيدروكسي –3- [5- (مورفولين –4- يل ميثيل) بيريدين –2- يل] 1h- إندول –5- كربونيتريل سترات - Google Patents
ملح سترات من مركب 2- هيدروكسي –3- [5- (مورفولين –4- يل ميثيل) بيريدين –2- يل] 1h- إندول –5- كربونيتريل سترات Download PDFInfo
- Publication number
- SA07280004B1 SA07280004B1 SA07280004A SA07280004A SA07280004B1 SA 07280004 B1 SA07280004 B1 SA 07280004B1 SA 07280004 A SA07280004 A SA 07280004A SA 07280004 A SA07280004 A SA 07280004A SA 07280004 B1 SA07280004 B1 SA 07280004B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- disease
- dementia
- salt
- morpholin
- pyridin
- Prior art date
Links
- QIXMKFAORYGAFN-UHFFFAOYSA-N 2-hydroxy-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-1H-indole-5-carbonitrile 2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(CC(O)=O)C(O)=O.Oc1[nH]c2ccc(cc2c1-c1ccc(CN2CCOCC2)cn1)C#N QIXMKFAORYGAFN-UHFFFAOYSA-N 0.000 title abstract description 14
- 150000001860 citric acid derivatives Chemical class 0.000 title description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
- 238000011282 treatment Methods 0.000 claims abstract description 28
- 102000001267 GSK3 Human genes 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 13
- 230000008569 process Effects 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 37
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 25
- 206010012289 Dementia Diseases 0.000 claims description 20
- 208000024827 Alzheimer disease Diseases 0.000 claims description 17
- 102000004190 Enzymes Human genes 0.000 claims description 17
- 108090000790 Enzymes Proteins 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 17
- 241000124008 Mammalia Species 0.000 claims description 16
- 210000000988 bone and bone Anatomy 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 206010012601 diabetes mellitus Diseases 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 230000002265 prevention Effects 0.000 claims description 14
- 208000001132 Osteoporosis Diseases 0.000 claims description 12
- BLTVBQXJFVRPFK-UHFFFAOYSA-N AZD1080 Chemical compound OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 BLTVBQXJFVRPFK-UHFFFAOYSA-N 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- -1 organic acids organic acids Chemical class 0.000 claims description 9
- 201000000980 schizophrenia Diseases 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 208000010877 cognitive disease Diseases 0.000 claims description 8
- 230000011164 ossification Effects 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 208000020925 Bipolar disease Diseases 0.000 claims description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 6
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 6
- 208000027089 Parkinsonian disease Diseases 0.000 claims description 6
- 206010034010 Parkinsonism Diseases 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 201000004384 Alopecia Diseases 0.000 claims description 5
- 208000019022 Mood disease Diseases 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
- 230000003176 fibrotic effect Effects 0.000 claims description 4
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 208000024714 major depressive disease Diseases 0.000 claims description 4
- 230000036651 mood Effects 0.000 claims description 4
- 210000002569 neuron Anatomy 0.000 claims description 4
- 201000001119 neuropathy Diseases 0.000 claims description 4
- 230000007823 neuropathy Effects 0.000 claims description 4
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 4
- 206010003694 Atrophy Diseases 0.000 claims description 3
- 206010026749 Mania Diseases 0.000 claims description 3
- 208000014060 Niemann-Pick disease Diseases 0.000 claims description 3
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 3
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 3
- 231100000360 alopecia Toxicity 0.000 claims description 3
- 230000037444 atrophy Effects 0.000 claims description 3
- 229940093915 gynecological organic acid Drugs 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 230000009529 traumatic brain injury Effects 0.000 claims description 3
- 208000028698 Cognitive impairment Diseases 0.000 claims description 2
- 102100038076 DNA dC->dU-editing enzyme APOBEC-3G Human genes 0.000 claims description 2
- 101000742736 Homo sapiens DNA dC->dU-editing enzyme APOBEC-3G Proteins 0.000 claims description 2
- 102000029797 Prion Human genes 0.000 claims description 2
- 108091000054 Prion Proteins 0.000 claims description 2
- 208000028017 Psychotic disease Diseases 0.000 claims description 2
- 206010048327 Supranuclear palsy Diseases 0.000 claims description 2
- 206010044688 Trisomy 21 Diseases 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 230000001054 cortical effect Effects 0.000 claims description 2
- 230000006866 deterioration Effects 0.000 claims description 2
- 206010014599 encephalitis Diseases 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 210000004558 lewy body Anatomy 0.000 claims description 2
- 206010027175 memory impairment Diseases 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims description 2
- 210000000225 synapse Anatomy 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 208000031124 Dementia Alzheimer type Diseases 0.000 claims 1
- 208000030451 Vascular dementia disease Diseases 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 208000025307 bipolar depression Diseases 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 208000024732 dysthymic disease Diseases 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 208000035475 disorder Diseases 0.000 abstract description 12
- 238000002360 preparation method Methods 0.000 abstract description 5
- 108060006662 GSK3 Proteins 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 210000004556 brain Anatomy 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 230000004770 neurodegeneration Effects 0.000 description 5
- 102000013498 tau Proteins Human genes 0.000 description 5
- 108010026424 tau Proteins Proteins 0.000 description 5
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 4
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- 206010017076 Fracture Diseases 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
- IDSXLJLXYMLSJM-UHFFFAOYSA-N morpholine;propane-1-sulfonic acid Chemical compound C1COCCN1.CCCS(O)(=O)=O IDSXLJLXYMLSJM-UHFFFAOYSA-N 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- YHYLDEVWYOFIJK-UHFFFAOYSA-N 1h-indole-5-carbonitrile Chemical compound N#CC1=CC=C2NC=CC2=C1 YHYLDEVWYOFIJK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000010392 Bone Fractures Diseases 0.000 description 3
- 102000016362 Catenins Human genes 0.000 description 3
- 108010067316 Catenins Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 108010001483 Glycogen Synthase Proteins 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 102000029749 Microtubule Human genes 0.000 description 3
- 108091022875 Microtubule Proteins 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 210000004688 microtubule Anatomy 0.000 description 3
- 208000015122 neurodegenerative disease Diseases 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 210000001428 peripheral nervous system Anatomy 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 208000006386 Bone Resorption Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 201000010374 Down Syndrome Diseases 0.000 description 2
- 102000038624 GSKs Human genes 0.000 description 2
- 108091007911 GSKs Proteins 0.000 description 2
- 229920002527 Glycogen Polymers 0.000 description 2
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 description 2
- 102100038104 Glycogen synthase kinase-3 beta Human genes 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 102000003982 Parathyroid hormone Human genes 0.000 description 2
- 108090000445 Parathyroid hormone Proteins 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
- 239000000164 antipsychotic agent Substances 0.000 description 2
- 229940005529 antipsychotics Drugs 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000024279 bone resorption Effects 0.000 description 2
- 230000030833 cell death Effects 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229940096919 glycogen Drugs 0.000 description 2
- 239000003102 growth factor Substances 0.000 description 2
- 230000003676 hair loss Effects 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- 201000010901 lateral sclerosis Diseases 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
- 238000002156 mixing Methods 0.000 description 2
- 208000005264 motor neuron disease Diseases 0.000 description 2
- 210000000963 osteoblast Anatomy 0.000 description 2
- 239000000199 parathyroid hormone Substances 0.000 description 2
- 229960001319 parathyroid hormone Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 102100027831 14-3-3 protein theta Human genes 0.000 description 1
- 206010065040 AIDS dementia complex Diseases 0.000 description 1
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 1
- 208000037259 Amyloid Plaque Diseases 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 102100030013 Endoribonuclease Human genes 0.000 description 1
- 101710199605 Endoribonuclease Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000282412 Homo Species 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
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 102000005877 Peptide Initiation Factors Human genes 0.000 description 1
- 108010044843 Peptide Initiation Factors Proteins 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 108091008611 Protein Kinase B Proteins 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
- 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010039984 Senile osteoporosis Diseases 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 101710113029 Serine/threonine-protein kinase Proteins 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000013528 artificial neural network Methods 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 210000003050 axon Anatomy 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 125000004057 biotinyl group Chemical group [H]N1C(=O)N([H])[C@]2([H])[C@@]([H])(SC([H])([H])[C@]12[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 230000008468 bone growth Effects 0.000 description 1
- 230000010478 bone regeneration Effects 0.000 description 1
- 239000012888 bovine serum Substances 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000033077 cellular process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 229960004170 clozapine Drugs 0.000 description 1
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 230000007278 cognition impairment Effects 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 208000021863 corticosteroid-induced osteoporosis Diseases 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000007357 depressive behavior Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000001544 dysphoric effect Effects 0.000 description 1
- 230000013020 embryo development Effects 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 238000012048 forced swim test Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 230000003779 hair growth Effects 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000000971 hippocampal effect Effects 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000005497 microtitration Methods 0.000 description 1
- 208000027061 mild cognitive impairment Diseases 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 201000000585 muscular atrophy Diseases 0.000 description 1
- 201000006938 muscular dystrophy Diseases 0.000 description 1
- 201000000050 myeloid neoplasm Diseases 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000004766 neurogenesis Effects 0.000 description 1
- 230000016273 neuron death Effects 0.000 description 1
- 230000006576 neuronal survival Effects 0.000 description 1
- 229960005017 olanzapine Drugs 0.000 description 1
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 1
- 238000011458 pharmacological treatment Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 208000001685 postmenopausal osteoporosis Diseases 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 229960004431 quetiapine Drugs 0.000 description 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000012089 stop solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004441 surface measurement Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000008736 traumatic injury Effects 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229960000607 ziprasidone Drugs 0.000 description 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/24—Antidepressants
-
- 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
- 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
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76455106P | 2006-02-02 | 2006-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SA07280004B1 true SA07280004B1 (ar) | 2011-10-29 |
Family
ID=38327680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SA07280004A SA07280004B1 (ar) | 2006-02-02 | 2007-01-23 | ملح سترات من مركب 2- هيدروكسي –3- [5- (مورفولين –4- يل ميثيل) بيريدين –2- يل] 1h- إندول –5- كربونيتريل سترات |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US8008294B2 (enExample) |
| EP (1) | EP1981869A4 (enExample) |
| JP (1) | JP2009525324A (enExample) |
| KR (1) | KR20080098022A (enExample) |
| CN (2) | CN101378754A (enExample) |
| AR (1) | AR059225A1 (enExample) |
| AU (1) | AU2007210336B2 (enExample) |
| BR (1) | BRPI0706745A2 (enExample) |
| CA (1) | CA2641900A1 (enExample) |
| EC (1) | ECSP088647A (enExample) |
| IL (1) | IL192888A0 (enExample) |
| MX (1) | MX2008009719A (enExample) |
| MY (1) | MY146102A (enExample) |
| NO (1) | NO20083784L (enExample) |
| NZ (1) | NZ570849A (enExample) |
| PE (1) | PE20090192A1 (enExample) |
| RU (1) | RU2415137C2 (enExample) |
| SA (1) | SA07280004B1 (enExample) |
| SG (1) | SG169381A1 (enExample) |
| TW (1) | TW200800977A (enExample) |
| UA (1) | UA94251C2 (enExample) |
| UY (1) | UY30126A1 (enExample) |
| WO (1) | WO2007089191A1 (enExample) |
| ZA (1) | ZA200806725B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SA07280004B1 (ar) * | 2006-02-02 | 2011-10-29 | استرازينيكا ايه بي | ملح سترات من مركب 2- هيدروكسي –3- [5- (مورفولين –4- يل ميثيل) بيريدين –2- يل] 1h- إندول –5- كربونيتريل سترات |
| CN101679353A (zh) * | 2007-04-18 | 2010-03-24 | 阿斯利康(瑞典)有限公司 | 制备化合物2-羟基-3-[5-(吗啉-4-基甲基)吡啶-2-基]1h-吲哚-5-腈701的新方法 |
| US20100267720A1 (en) * | 2007-07-30 | 2010-10-21 | Astrazeneca Ab | Crystalline Forms of 2-Hydroxy-3- [5- (Morpholin- 4- Ylmethyl) Pyridin-2-YL] IH- Indole- 5 -Carbonitrile Citrate |
| US20100189790A1 (en) | 2009-01-23 | 2010-07-29 | Teva Pharmaceutical Industries, Ltd. | Delayed release rasagiline formulation |
| WO2020163812A1 (en) | 2019-02-08 | 2020-08-13 | Frequency Therapeutics, Inc. | Valproic acid compounds and wnt agonists for treating ear disorders |
| CN120441567A (zh) * | 2020-04-07 | 2025-08-08 | Crt先锋基金有限公司 | Chk1抑制剂的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1373263T1 (en) | 2001-04-05 | 2005-04-30 | Torrent Pharmaceuticals Ltd | Heterocyclic compounds for aging-related and diabetic vascular complications |
| JP2003009588A (ja) | 2001-06-20 | 2003-01-10 | Toshiba Corp | 車両連続運転装置用インバータ装置 |
| SE0200979D0 (sv) * | 2002-03-28 | 2002-03-28 | Astrazeneca Ab | New compounds |
| SE0302546D0 (sv) * | 2003-09-24 | 2003-09-24 | Astrazeneca Ab | New compounds |
| JP2007502300A (ja) * | 2003-08-13 | 2007-02-08 | カイロン コーポレイション | Ｇｓｋ−３インヒビターおよびその使用 |
| MX2007008008A (es) | 2004-12-30 | 2007-11-12 | Astex Therapeutics Ltd | Compuestos de pirazol que modulan la actividad de las cinasas cdk, gsk y aurora. |
| SA07280004B1 (ar) * | 2006-02-02 | 2011-10-29 | استرازينيكا ايه بي | ملح سترات من مركب 2- هيدروكسي –3- [5- (مورفولين –4- يل ميثيل) بيريدين –2- يل] 1h- إندول –5- كربونيتريل سترات |
-
2007
- 2007-01-23 SA SA07280004A patent/SA07280004B1/ar unknown
- 2007-01-29 AR ARP070100366A patent/AR059225A1/es not_active Application Discontinuation
- 2007-01-29 TW TW096103245A patent/TW200800977A/zh unknown
- 2007-01-31 MX MX2008009719A patent/MX2008009719A/es active IP Right Grant
- 2007-01-31 SG SG201100793-7A patent/SG169381A1/en unknown
- 2007-01-31 EP EP07709302A patent/EP1981869A4/en not_active Withdrawn
- 2007-01-31 MY MYPI20082900A patent/MY146102A/en unknown
- 2007-01-31 CA CA002641900A patent/CA2641900A1/en not_active Abandoned
- 2007-01-31 NZ NZ570849A patent/NZ570849A/en not_active IP Right Cessation
- 2007-01-31 CN CNA2007800043630A patent/CN101378754A/zh active Pending
- 2007-01-31 BR BRPI0706745-3A patent/BRPI0706745A2/pt not_active IP Right Cessation
- 2007-01-31 WO PCT/SE2007/000086 patent/WO2007089191A1/en not_active Ceased
- 2007-01-31 RU RU2008131906/04A patent/RU2415137C2/ru not_active IP Right Cessation
- 2007-01-31 UA UAA200809265A patent/UA94251C2/ru unknown
- 2007-01-31 JP JP2008553201A patent/JP2009525324A/ja not_active Ceased
- 2007-01-31 CN CNA2007800041531A patent/CN101379053A/zh active Pending
- 2007-01-31 KR KR1020087019047A patent/KR20080098022A/ko not_active Ceased
- 2007-01-31 UY UY30126A patent/UY30126A1/es not_active Application Discontinuation
- 2007-01-31 US US12/162,540 patent/US8008294B2/en not_active Expired - Fee Related
- 2007-01-31 AU AU2007210336A patent/AU2007210336B2/en not_active Ceased
- 2007-02-02 US US11/670,681 patent/US20070203137A1/en not_active Abandoned
- 2007-08-02 PE PE2007001013A patent/PE20090192A1/es not_active Application Discontinuation
-
2008
- 2008-07-17 IL IL192888A patent/IL192888A0/en unknown
- 2008-07-24 EC EC2008008647A patent/ECSP088647A/es unknown
- 2008-08-01 ZA ZA200806725A patent/ZA200806725B/xx unknown
- 2008-09-02 NO NO20083784A patent/NO20083784L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200806725B (en) | 2009-07-29 |
| CN101379053A (zh) | 2009-03-04 |
| EP1981869A4 (en) | 2010-08-25 |
| NO20083784L (no) | 2008-10-13 |
| NZ570849A (en) | 2011-01-28 |
| RU2415137C2 (ru) | 2011-03-27 |
| UA94251C2 (ru) | 2011-04-26 |
| CA2641900A1 (en) | 2007-08-09 |
| AU2007210336B2 (en) | 2011-03-24 |
| MY146102A (en) | 2012-06-29 |
| JP2009525324A (ja) | 2009-07-09 |
| AU2007210336A1 (en) | 2007-08-09 |
| TW200800977A (en) | 2008-01-01 |
| BRPI0706745A2 (pt) | 2011-04-05 |
| SG169381A1 (en) | 2011-03-30 |
| ECSP088647A (es) | 2008-08-29 |
| PE20090192A1 (es) | 2009-03-20 |
| US20090023732A1 (en) | 2009-01-22 |
| UY30126A1 (es) | 2007-09-28 |
| EP1981869A1 (en) | 2008-10-22 |
| KR20080098022A (ko) | 2008-11-06 |
| RU2008131906A (ru) | 2010-03-10 |
| AR059225A1 (es) | 2008-03-19 |
| US8008294B2 (en) | 2011-08-30 |
| MX2008009719A (es) | 2008-09-04 |
| WO2007089191A1 (en) | 2007-08-09 |
| US20070203137A1 (en) | 2007-08-30 |
| IL192888A0 (en) | 2009-02-11 |
| CN101378754A (zh) | 2009-03-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1458395B1 (en) | Medical use of gsk3-inhibiting oxindole derivatives | |
| EP2108648A1 (de) | Ausgewählte CGRP-Antagonisten, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel | |
| JP5501352B2 (ja) | 置換ピリミド［２，１−ａ］イソキノリン−４−オン誘導体 | |
| JP2011525906A (ja) | 置換されたピリミドン誘導体 | |
| ES2222396T3 (es) | Compuestos utiles como ingrediente activo de un medicamento para el tratamiento preventivo y/o terapeutico de enfermedades neurodegenerativas. | |
| JP2010535200A (ja) | ２−ヒドロキシ−３−［５−（モルホリン−４−イルメチル）ピリジン−２−イル］−１ｈ−インドール−５−カルボニトリル・クエン酸塩の新しい結晶形態 | |
| NO325245B1 (no) | Ftalayinon-piperidinderivater, legemidler inneholdende disse og deres anvendelse | |
| JP2013532657A (ja) | 環式ｎ，ｎ’−ジアリールチオ尿素及びｎ，ｎ’−ジアリール尿素−アンドロゲン受容体アンタゴニスト、抗癌剤、その調製のための方法及び使用 | |
| AU2007210336B2 (en) | New citrate salt of an indole derivative and its pharmaceutical use | |
| EP3263573A1 (en) | Crystal of imidazo-oxazine, pharmaceutical composition containing said crystal, and method for producing said crystal | |
| JP2011231022A (ja) | イミダゾロン誘導体 | |
| US20120115865A1 (en) | New Salts of an Indole Derivative and Their Use in Medicine | |
| WO2009050252A1 (en) | Novel sulfamate compounds for medical use | |
| KR102960952B1 (ko) | 골질환 예방 또는 치료용 약학 조성물 | |
| EP4553078A1 (en) | 5h-pyrrolo[2,3-d]pyrimidin-6(7h)-one and crystal of salt thereof | |
| WO2012050517A1 (en) | Imidazole substituted pyrimidine having a high gsk3 inhibiting potency as well as pan-kinase selectivity | |
| HK1129382A (en) | New citrate salt of an indole derivative and its pharmaceutical use | |
| CN121202834A (zh) | 一类胺烷氧基烟碱类化合物及其制备方法和用途 | |
| CA2970232A1 (en) | Pharmaceutical composition having bicyclic nitrogen-containing aromatic heterocyclic amide compound as active component | |
| CN121202835A (zh) | 一类胺烷氧基可替宁类化合物及其制备方法和用途 | |
| CN121758402A (zh) | 一类3-(胺烷硫基)苄氧基苯酞及其制备方法和用途 | |
| CN120607466A (zh) | 酰胺烷硫醇酯类化合物及其制备方法和用途 | |
| CN104017029A (zh) | 氨基葡萄糖衍生物或其药学上可接受的盐 | |
| TW201518276A (zh) | 吲哚衍生物之鹽及其結晶 |