BR112019013244A2 - sais e polimorfos de oxalato de tianeptina - Google Patents
sais e polimorfos de oxalato de tianeptina Download PDFInfo
- Publication number
- BR112019013244A2 BR112019013244A2 BR112019013244A BR112019013244A BR112019013244A2 BR 112019013244 A2 BR112019013244 A2 BR 112019013244A2 BR 112019013244 A BR112019013244 A BR 112019013244A BR 112019013244 A BR112019013244 A BR 112019013244A BR 112019013244 A2 BR112019013244 A2 BR 112019013244A2
- Authority
- BR
- Brazil
- Prior art keywords
- tianeptine
- oxalate
- crystalline
- hemioxalate
- mono
- Prior art date
Links
- 150000003891 oxalate salts Chemical class 0.000 title abstract description 5
- JICJBGPOMZQUBB-UHFFFAOYSA-N 7-[(3-chloro-6-methyl-5,5-dioxido-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic acid Chemical compound O=S1(=O)N(C)C2=CC=CC=C2C(NCCCCCCC(O)=O)C2=CC=C(Cl)C=C21 JICJBGPOMZQUBB-UHFFFAOYSA-N 0.000 claims abstract description 189
- 229960005138 tianeptine Drugs 0.000 claims abstract description 188
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 70
- -1 3-chloro-6-methyl-6,11-dihydrodibenzo [c , f] [1,2] thiazepin-11-ylamino Chemical group 0.000 claims abstract description 11
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 238000001157 Fourier transform infrared spectrum Methods 0.000 claims description 10
- 230000002035 prolonged effect Effects 0.000 claims description 7
- 238000002441 X-ray diffraction Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 230000001747 exhibiting effect Effects 0.000 claims description 5
- 230000003111 delayed effect Effects 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 239000012730 sustained-release form Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 3
- 239000003246 corticosteroid Substances 0.000 description 18
- 229960001334 corticosteroids Drugs 0.000 description 15
- 238000000113 differential scanning calorimetry Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 235000006408 oxalic acid Nutrition 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 150000003431 steroids Chemical class 0.000 description 8
- 238000002411 thermogravimetry Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 208000028173 post-traumatic stress disease Diseases 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000013270 controlled release Methods 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000001757 thermogravimetry curve Methods 0.000 description 5
- 208000019022 Mood disease Diseases 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000035882 stress Effects 0.000 description 4
- 208000019901 Anxiety disease Diseases 0.000 description 3
- 208000028698 Cognitive impairment Diseases 0.000 description 3
- 206010012289 Dementia Diseases 0.000 description 3
- 208000020401 Depressive disease Diseases 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 208000010877 cognitive disease Diseases 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000013265 extended release Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000004927 fusion Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 230000003204 osmotic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000000392 somatic effect Effects 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010012218 Delirium Diseases 0.000 description 2
- 102100021202 Desmocollin-1 Human genes 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 102000003676 Glucocorticoid Receptors Human genes 0.000 description 2
- 108090000079 Glucocorticoid Receptors Proteins 0.000 description 2
- 101000968043 Homo sapiens Desmocollin-1 Proteins 0.000 description 2
- 101000880960 Homo sapiens Desmocollin-3 Proteins 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 2
- 210000004100 adrenal gland Anatomy 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 230000001149 cognitive effect Effects 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229930195712 glutamate Natural products 0.000 description 2
- 230000000848 glutamatergic effect Effects 0.000 description 2
- 210000001320 hippocampus Anatomy 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 229960000890 hydrocortisone Drugs 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 230000027928 long-term synaptic potentiation Effects 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000015654 memory Effects 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000009461 neurocognitive dysfunction Effects 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 230000002085 persistent 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
- 239000006187 pill Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000001304 sample melting Methods 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- 238000004922 13C solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 208000026872 Addison Disease Diseases 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 1
- 206010003827 Autoimmune hepatitis Diseases 0.000 description 1
- 208000030016 Avascular necrosis Diseases 0.000 description 1
- 208000020925 Bipolar disease Diseases 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 208000004930 Fatty Liver Diseases 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 206010072079 Glucocorticoid deficiency Diseases 0.000 description 1
- 206010019708 Hepatic steatosis Diseases 0.000 description 1
- 206010020112 Hirsutism Diseases 0.000 description 1
- 101000687911 Homo sapiens Transcription factor SOX-3 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010021067 Hypopituitarism Diseases 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 206010025327 Lymphopenia Diseases 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 206010026865 Mass Diseases 0.000 description 1
- 208000021642 Muscular disease Diseases 0.000 description 1
- 201000009623 Myopathy Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010065673 Nephritic syndrome Diseases 0.000 description 1
- 208000029726 Neurodevelopmental disease Diseases 0.000 description 1
- 206010029379 Neutrophilia Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000007027 Oral Candidiasis Diseases 0.000 description 1
- 206010031264 Osteonecrosis Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 208000027030 Premenstrual dysphoric disease Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 206010041277 Sodium retention Diseases 0.000 description 1
- 208000031439 Striae Distensae Diseases 0.000 description 1
- 208000011963 Substance-induced psychotic disease Diseases 0.000 description 1
- 102100024276 Transcription factor SOX-3 Human genes 0.000 description 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 208000026345 acute stress disease Diseases 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 210000004727 amygdala Anatomy 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 208000028683 bipolar I disease Diseases 0.000 description 1
- 208000025307 bipolar depression Diseases 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 230000001269 cardiogenic effect Effects 0.000 description 1
- 206010007625 cardiogenic shock Diseases 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000010326 executive functioning Effects 0.000 description 1
- 208000010706 fatty liver disease Diseases 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000008297 genomic mechanism Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 206010024378 leukocytosis Diseases 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 231100001023 lymphopenia Toxicity 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960001810 meprednisone Drugs 0.000 description 1
- PIDANAQULIKBQS-RNUIGHNZSA-N meprednisone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)CC2=O PIDANAQULIKBQS-RNUIGHNZSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000000955 neuroendocrine Effects 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000008298 non-genomic mechanism Effects 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 201000009958 panhypopituitarism Diseases 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 210000002442 prefrontal cortex Anatomy 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 238000003196 serial analysis of gene expression Methods 0.000 description 1
- 230000006403 short-term memory Effects 0.000 description 1
- ZLBSUOGMZDXYKE-UHFFFAOYSA-M sodium;7-[(3-chloro-6-methyl-5,5-dioxo-11h-benzo[c][2,1]benzothiazepin-11-yl)amino]heptanoate Chemical compound [Na+].O=S1(=O)N(C)C2=CC=CC=C2C(NCCCCCCC([O-])=O)C2=CC=C(Cl)C=C21 ZLBSUOGMZDXYKE-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000547 structure data Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000000003 thermogravimetry coupled to Fourier transform infrared spectroscopy Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000003936 working memory Effects 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P25/18—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662439533P | 2016-12-28 | 2016-12-28 | |
| PCT/IB2017/001709 WO2018122606A1 (en) | 2016-12-28 | 2017-12-28 | Tianeptine oxalate salts and polymorphs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BR112019013244A2 true BR112019013244A2 (pt) | 2019-12-24 |
Family
ID=61283255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112019013244A BR112019013244A2 (pt) | 2016-12-28 | 2017-12-28 | sais e polimorfos de oxalato de tianeptina |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US10449203B2 (enExample) |
| EP (1) | EP3562812A1 (enExample) |
| JP (2) | JP2020503330A (enExample) |
| CN (1) | CN110418785A (enExample) |
| AU (1) | AU2017385958B2 (enExample) |
| BR (1) | BR112019013244A2 (enExample) |
| CA (1) | CA3048324A1 (enExample) |
| IL (1) | IL267708A (enExample) |
| MX (1) | MX2019007891A (enExample) |
| MY (1) | MY199385A (enExample) |
| NZ (1) | NZ754797A (enExample) |
| WO (1) | WO2018122606A1 (enExample) |
| ZA (1) | ZA201904185B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ754797A (en) * | 2016-12-28 | 2022-05-27 | Tonix Pharma Holdings Ltd | Tianeptine oxalate salts and polymorphs |
| US20240165126A1 (en) | 2021-03-15 | 2024-05-23 | Tonix Pharmaceuticals Holding Corp. | Tianeptine oxalate and naloxone combination for the treatment of major depressive disorder |
| CN117769540A (zh) * | 2021-05-11 | 2024-03-26 | 亚士德制药公司 | 4-[5-[(3S)-3-氨基吡咯烷-l-羰基]-2-[2-氟-4-(2-羟基-2-乙基丙基)苯基]苯基]-2-氟-苯甲腈的盐的固体形式 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3758528A (en) * | 1970-03-13 | 1973-09-11 | Science Union & Cie | Tricyclic compounds |
| FR2635461B1 (fr) * | 1988-08-18 | 1992-01-17 | Adir | Utilisation de derives tricycliques pour l'obtention de medicaments destines au traitement du stress |
| US5405842A (en) | 1994-01-28 | 1995-04-11 | Silverman; Bernard A. | Treatment of steroid dependent asthmatics |
| FR2791891A1 (fr) | 1999-04-07 | 2000-10-13 | Adir | Utilisation de la tianeptine pour l'obtention de medicaments destines au traitement des pathologies de la neurodegenerescence |
| TW200517114A (en) | 2003-10-15 | 2005-06-01 | Combinatorx Inc | Methods and reagents for the treatment of immunoinflammatory disorders |
| US9314469B2 (en) | 2008-05-05 | 2016-04-19 | Tonix Pharma Holdings Limited | Method for treating neurocognitive dysfunction |
| US8198268B2 (en) * | 2008-10-31 | 2012-06-12 | Janssen Biotech, Inc. | Tianeptine sulfate salt forms and methods of making and using the same |
| NZ754797A (en) * | 2016-12-28 | 2022-05-27 | Tonix Pharma Holdings Ltd | Tianeptine oxalate salts and polymorphs |
-
2017
- 2017-12-28 NZ NZ754797A patent/NZ754797A/en not_active IP Right Cessation
- 2017-12-28 WO PCT/IB2017/001709 patent/WO2018122606A1/en not_active Ceased
- 2017-12-28 MX MX2019007891A patent/MX2019007891A/es unknown
- 2017-12-28 US US15/856,818 patent/US10449203B2/en active Active
- 2017-12-28 AU AU2017385958A patent/AU2017385958B2/en not_active Ceased
- 2017-12-28 CN CN201780085697.9A patent/CN110418785A/zh active Pending
- 2017-12-28 CA CA3048324A patent/CA3048324A1/en active Pending
- 2017-12-28 JP JP2019535330A patent/JP2020503330A/ja active Pending
- 2017-12-28 MY MYPI2019003711A patent/MY199385A/en unknown
- 2017-12-28 EP EP17844642.3A patent/EP3562812A1/en not_active Withdrawn
- 2017-12-28 BR BR112019013244A patent/BR112019013244A2/pt not_active IP Right Cessation
-
2019
- 2019-06-26 ZA ZA2019/04185A patent/ZA201904185B/en unknown
- 2019-06-27 IL IL267708A patent/IL267708A/en unknown
- 2019-10-09 US US16/597,065 patent/US10946027B2/en active Active
-
2022
- 2022-11-10 JP JP2022180549A patent/JP2023001340A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US10449203B2 (en) | 2019-10-22 |
| AU2017385958B2 (en) | 2021-12-02 |
| CN110418785A (zh) | 2019-11-05 |
| MY199385A (en) | 2023-10-25 |
| US10946027B2 (en) | 2021-03-16 |
| WO2018122606A1 (en) | 2018-07-05 |
| US20200276208A1 (en) | 2020-09-03 |
| JP2023001340A (ja) | 2023-01-04 |
| NZ754797A (en) | 2022-05-27 |
| EP3562812A1 (en) | 2019-11-06 |
| ZA201904185B (en) | 2021-10-27 |
| AU2017385958A1 (en) | 2019-07-11 |
| IL267708A (en) | 2019-08-29 |
| US20180338984A1 (en) | 2018-11-29 |
| MX2019007891A (es) | 2019-12-16 |
| CA3048324A1 (en) | 2018-07-05 |
| JP2020503330A (ja) | 2020-01-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Fucke et al. | How good are the crystallisation methods for co-crystals? A comparative study of piroxicam | |
| WO2021244323A1 (zh) | 一种乌帕替尼的晶型及其制备方法和用途 | |
| JP6720280B2 (ja) | 新規アベキシノスタット塩、関連結晶形態、それらの調製方法およびそれらを含有する医薬組成物 | |
| JP2018515569A (ja) | キナーゼを調節するための化合物の固体形態 | |
| Khatioda et al. | Solubility and in vitro drug permeation behavior of ethenzamide cocrystals regulated in physiological pH environments | |
| JP2013173788A (ja) | ２−メチル−２−［４−（３−メチル−２−オキソ−８−キノリン−３−イル−２，３−ジヒドロ−イミダゾ［４，５−ｃ］キノリン−１−イル）−フェニル］−プロピオニトリルの塩および結晶形態 | |
| JP2023001340A (ja) | チアネプチンシュウ酸塩および多形 | |
| US12285396B2 (en) | Co-crystal of ketoprofen, compositions comprising the same, process of producing the same, and uses thereof | |
| Ma et al. | Preparation of meloxicam-salicylic acid co-crystal and its application in the treatment of rheumatoid arthritis | |
| Li et al. | The delivery of arbidol by salt engineering: Synthesis, physicochemical properties and pharmacokinetics | |
| CN111320583A (zh) | 诺德司他新晶型及其制备方法 | |
| PT898579E (pt) | Derivados de pregnano sem substituinte na posicao 17alfa sua utilizacao como medicamento processo para a sua preparacao intermediarios do processo e composicoes que os contem | |
| Yu et al. | Salt or/and cocrystal? The case of the antidepressant drug venlafaxine | |
| JP2013538872A (ja) | 癌治療における使用のためのピクロポドフィリン多形体ｂ又はｃ | |
| WO2013097835A1 (es) | Sistemas espiroesteroidales con efectos neuroactivos y anti- inflamatorios | |
| JP2000503985A (ja) | 増強剤としての新規なステロイドカルバメート | |
| CN112898168B (zh) | 一种2-羟基苄胺-丁二酸的盐及其制备方法 | |
| BR112016017490B1 (pt) | Composição farmacêutica incluindo 5-{4-(aminossulfonil)fenil}-2,2- dimetil-4-(3-fluorfenil)-3(2h)-furanona e formulação de cápsula incluindo a composição farmacêutica | |
| Sahu et al. | An Updated Review on Pharmaceutical Co-Crystals: Characterization and Preparation | |
| RU2844681C2 (ru) | Новые кристаллические формы mcl-1 ингибитора, способ их получения и содержащие их фармацевтические композиции | |
| HK40016628A (zh) | 噻奈普汀草酸盐和多晶型 | |
| JP2021527119A (ja) | 塩形態 | |
| TWI535725B (zh) | 用以治療發炎和／或腫瘤的新穎倍半萜類化合物之衍生物及包含此新穎倍半萜類化合物之衍生物的組合物 | |
| Xu et al. | Discovery of novel long-acting co-prodrugs NSAIDs-PEA: synthesis, nanocrystals preparation, characterizations and antinociceptive effects | |
| WO2026017797A1 (en) | Crystalline forms |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B07D | Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette] |
Free format text: DE ACORDO COM O ARTIGO 229-C DA LEI N? 10196/2001, QUE MODIFICOU A LEI N? 9279/96, A CONCESS?O DA PATENTE EST? CONDICIONADA ? ANU?NCIA PR?VIA DA ANVISA. CONSIDERANDO A APROVA??O DOS TERMOS DO PARECER N? 337/PGF/EA/2010, BEM COMO A PORTARIA INTERMINISTERIAL N? 1065 DE 24/05/2012, ENCAMINHA-SE O PRESENTE PEDIDO PARA AS PROVID?NCIAS CAB?VEIS. |
|
| B07E | Notification of approval relating to section 229 industrial property law [chapter 7.5 patent gazette] | ||
| B06W | Patent application suspended after preliminary examination (for patents with searches from other patent authorities) chapter 6.23 patent gazette] | ||
| B350 | Update of information on the portal [chapter 15.35 patent gazette] | ||
| B08F | Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette] |
Free format text: REFERENTE A 7A ANUIDADE. |
|
| B08K | Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette] |
Free format text: EM VIRTUDE DO ARQUIVAMENTO PUBLICADO NA RPI 2807 DE 22-10-2024 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDO O ARQUIVAMENTO DO PEDIDO DE PATENTE, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013. |