TWI359660B - Succinate salt of 2-((4-(1-methyl-4-(pyridin-4-yl) - Google Patents
Succinate salt of 2-((4-(1-methyl-4-(pyridin-4-yl) Download PDFInfo
- Publication number
- TWI359660B TWI359660B TW096148920A TW96148920A TWI359660B TW I359660 B TWI359660 B TW I359660B TW 096148920 A TW096148920 A TW 096148920A TW 96148920 A TW96148920 A TW 96148920A TW I359660 B TWI359660 B TW I359660B
- Authority
- TW
- Taiwan
- Prior art keywords
- salt
- depression
- dementia
- disease
- application
- Prior art date
Links
- 150000003890 succinate salts Chemical class 0.000 title description 11
- 239000003814 drug Substances 0.000 claims description 26
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 25
- 229940079593 drug Drugs 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 10
- 208000019901 Anxiety disease Diseases 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 230000004770 neurodegeneration Effects 0.000 claims description 9
- 208000024891 symptom Diseases 0.000 claims description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 201000000980 schizophrenia Diseases 0.000 claims description 8
- 206010033864 Paranoia Diseases 0.000 claims description 7
- 208000027099 Paranoid disease Diseases 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 206010013663 drug dependence Diseases 0.000 claims description 7
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 7
- 208000020925 Bipolar disease Diseases 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 208000020016 psychiatric disease Diseases 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 208000011117 substance-related disease Diseases 0.000 claims description 6
- 208000012661 Dyskinesia Diseases 0.000 claims description 5
- 208000011963 Substance-induced psychotic disease Diseases 0.000 claims description 5
- 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims description 5
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 5
- 201000002545 drug psychosis Diseases 0.000 claims description 5
- 230000002996 emotional effect Effects 0.000 claims description 5
- 210000005036 nerve Anatomy 0.000 claims description 5
- 208000027534 Emotional disease Diseases 0.000 claims description 4
- 208000019022 Mood disease Diseases 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 3
- 206010022998 Irritability Diseases 0.000 claims description 3
- 206010026749 Mania Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 229940025084 amphetamine Drugs 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 3
- 238000012986 modification Methods 0.000 claims description 3
- 230000036651 mood Effects 0.000 claims description 3
- 229940127240 opiate Drugs 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 206010010904 Convulsion Diseases 0.000 claims description 2
- 206010036790 Productive cough Diseases 0.000 claims description 2
- 230000007000 age related cognitive decline Effects 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 208000024794 sputum Diseases 0.000 claims description 2
- 210000003802 sputum Anatomy 0.000 claims description 2
- 238000012360 testing method Methods 0.000 claims description 2
- 206010012289 Dementia Diseases 0.000 claims 8
- 206010061216 Infarction Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 230000007574 infarction Effects 0.000 claims 2
- 208000022821 personality disease Diseases 0.000 claims 2
- 206010065040 AIDS dementia complex Diseases 0.000 claims 1
- 208000000044 Amnesia Diseases 0.000 claims 1
- 208000031091 Amnestic disease Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 244000025254 Cannabis sativa Species 0.000 claims 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims 1
- 206010012239 Delusion Diseases 0.000 claims 1
- 240000006890 Erythroxylum coca Species 0.000 claims 1
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- 206010020565 Hyperaemia Diseases 0.000 claims 1
- 208000013016 Hypoglycemia Diseases 0.000 claims 1
- 208000020358 Learning disease Diseases 0.000 claims 1
- 208000036626 Mental retardation Diseases 0.000 claims 1
- 208000001089 Multiple system atrophy Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010029350 Neurotoxicity Diseases 0.000 claims 1
- 108010010677 Phosphodiesterase I Proteins 0.000 claims 1
- 208000028810 Shared psychotic disease Diseases 0.000 claims 1
- 206010041235 Snoring Diseases 0.000 claims 1
- 206010044221 Toxic encephalopathy Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 230000006986 amnesia Effects 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 230000004888 barrier function Effects 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 208000026106 cerebrovascular disease Diseases 0.000 claims 1
- 235000008957 cocaer Nutrition 0.000 claims 1
- 231100000868 delusion Toxicity 0.000 claims 1
- 239000000380 hallucinogen Substances 0.000 claims 1
- 230000002218 hypoglycaemic effect Effects 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 230000003340 mental effect Effects 0.000 claims 1
- 230000007135 neurotoxicity Effects 0.000 claims 1
- 231100000228 neurotoxicity Toxicity 0.000 claims 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims 1
- 229950010883 phencyclidine Drugs 0.000 claims 1
- 230000000698 schizophrenic effect Effects 0.000 claims 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 238000000034 method Methods 0.000 description 21
- 241000124008 Mammalia Species 0.000 description 16
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- 238000000634 powder X-ray diffraction Methods 0.000 description 12
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 9
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 9
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 108090000623 proteins and genes Proteins 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 108010044467 Isoenzymes Proteins 0.000 description 5
- 210000003169 central nervous system Anatomy 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- -1 soft f Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 102000030621 adenylate cyclase Human genes 0.000 description 2
- 108060000200 adenylate cyclase Proteins 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 229960003920 cocaine Drugs 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 230000004807 localization Effects 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
- 108020004999 messenger RNA Proteins 0.000 description 2
- 150000004712 monophosphates Chemical class 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 101710095468 Cyclase Proteins 0.000 description 1
- 206010012218 Delirium Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 208000010228 Erectile Dysfunction Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 108010078321 Guanylate Cyclase Proteins 0.000 description 1
- 102000014469 Guanylate cyclase Human genes 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 101100028926 Mus musculus Pde10a gene Proteins 0.000 description 1
- 208000011623 Obstructive Lung disease Diseases 0.000 description 1
- 206010068319 Oropharyngeal pain Diseases 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 201000007100 Pharyngitis Diseases 0.000 description 1
- 206010034912 Phobia Diseases 0.000 description 1
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 206010041250 Social phobia Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000026345 acute stress disease Diseases 0.000 description 1
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- XMPZLAQHPIBDSO-UHFFFAOYSA-N argon dimer Chemical compound [Ar].[Ar] XMPZLAQHPIBDSO-UHFFFAOYSA-N 0.000 description 1
- 208000025748 atypical depressive disease Diseases 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- RQFCJASXJCIDSX-UUOKFMHZSA-N guanosine 5'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O RQFCJASXJCIDSX-UUOKFMHZSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002055 immunohistochemical effect Effects 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000006525 intracellular process Effects 0.000 description 1
- 230000031146 intracellular signal transduction Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 201000003995 melancholia Diseases 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000956 olfactory bulb Anatomy 0.000 description 1
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 208000008148 parkinson disease 12 Diseases 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 208000019899 phobic disease Diseases 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000001907 polarising light microscopy Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000014786 regulation of synaptic transmission Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000008844 regulatory mechanism Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 201000001716 specific phobia Diseases 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
- C07D401/14—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 three or more hetero rings
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (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 |
|---|---|---|---|
| US87126006P | 2006-12-21 | 2006-12-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200833337A TW200833337A (en) | 2008-08-16 |
| TWI359660B true TWI359660B (en) | 2012-03-11 |
Family
ID=39321475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW096148920A TWI359660B (en) | 2006-12-21 | 2007-12-20 | Succinate salt of 2-((4-(1-methyl-4-(pyridin-4-yl) |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US8283471B2 (enExample) |
| EP (1) | EP2125786B1 (enExample) |
| JP (1) | JP5254602B2 (enExample) |
| KR (2) | KR20090092338A (enExample) |
| CN (1) | CN101611029B (enExample) |
| AR (1) | AR064417A1 (enExample) |
| AT (1) | ATE502028T1 (enExample) |
| AU (1) | AU2007343135B2 (enExample) |
| BR (1) | BRPI0720936A2 (enExample) |
| CA (1) | CA2673435C (enExample) |
| CY (1) | CY1111919T1 (enExample) |
| DE (1) | DE602007013294D1 (enExample) |
| DK (1) | DK2125786T3 (enExample) |
| ES (1) | ES2360014T3 (enExample) |
| IL (1) | IL199389A (enExample) |
| MX (1) | MX2009006528A (enExample) |
| NZ (1) | NZ577716A (enExample) |
| PL (1) | PL2125786T3 (enExample) |
| PT (1) | PT2125786E (enExample) |
| RU (1) | RU2430918C2 (enExample) |
| SI (1) | SI2125786T1 (enExample) |
| TW (1) | TWI359660B (enExample) |
| WO (1) | WO2008084299A1 (enExample) |
| ZA (1) | ZA200904230B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010033045A1 (en) * | 2008-09-16 | 2010-03-25 | Igor Anatolievich Pomytkin | Compositions and methods for prevention or treatment of beta amyloid deposition |
| TWI396689B (zh) | 2008-11-14 | 2013-05-21 | Amgen Inc | 作為磷酸二酯酶10抑制劑之吡衍生物 |
| US20120214842A1 (en) * | 2011-02-18 | 2012-08-23 | Exonhit Therapeutics Sa | Methods for treating diseases of the retina |
| EP2975037A4 (en) | 2013-03-15 | 2016-08-10 | Daiichi Sankyo Co Ltd | benzothiophene derivative |
| US10039764B2 (en) | 2013-07-12 | 2018-08-07 | University Of South Alabama | Treatment and diagnosis of cancer and precancerous conditions using PDE10A inhibitors and methods to measure PDE10A expression |
| KR102233916B1 (ko) * | 2019-05-28 | 2021-03-30 | 주식회사 엘지생활건강 | Pq1 숙신산을 포함하는 피부 보습, 주름 개선 및 탄력 증진용 조성물 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4105551A1 (de) * | 1991-02-22 | 1992-08-27 | Bayer Ag | 2-substituierte chinoline, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| US5795909A (en) * | 1996-05-22 | 1998-08-18 | Neuromedica, Inc. | DHA-pharmaceutical agent conjugates of taxanes |
| EA011451B1 (ru) * | 2001-02-12 | 2009-04-28 | Уайт | Новая соль сукцинат о-десметилвенлафаксина |
| IL161326A0 (en) * | 2001-11-29 | 2004-09-27 | Pfizer Prod Inc | Succinic acid salts of 5,8,14-triazatetracyclo'10.3.1.0<2,11>.0<4,9>-hexadeca-2 (11),3,5,7,9-pentaene and pharmaceutical compositions thereof |
| CN1608062A (zh) * | 2001-12-12 | 2005-04-20 | 辉瑞产品公司 | E-2-甲氧基-n-(3-{4-[3-甲基-4-(6-甲基-吡啶-3-基氧基) -苯氨基]-喹唑啉-6基}-烯丙基)-乙酰胺的盐,其制备和抗癌用途 |
| CA2536073A1 (en) * | 2003-08-18 | 2005-02-24 | H. Lundbeck A/S | Trans-1(6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine |
| WO2006072828A2 (en) * | 2005-01-07 | 2006-07-13 | Pfizer Products Inc. | Heteroaromatic quinoline compounds and their use as pde10 inhibitors |
| WO2006078825A2 (en) | 2005-01-21 | 2006-07-27 | Cabot Corporation | Processes for forming nanoparticles |
| AU2006329849A1 (en) * | 2005-12-16 | 2007-07-05 | Wyeth | Lyophilized compositions of a triazolopyrimidine compound |
-
2007
- 2007-12-03 CN CN200780051566.5A patent/CN101611029B/zh not_active Expired - Fee Related
- 2007-12-03 EP EP07858987A patent/EP2125786B1/en not_active Not-in-force
- 2007-12-03 AU AU2007343135A patent/AU2007343135B2/en not_active Ceased
- 2007-12-03 CA CA2673435A patent/CA2673435C/en not_active Expired - Fee Related
- 2007-12-03 SI SI200730561T patent/SI2125786T1/sl unknown
- 2007-12-03 PL PL07858987T patent/PL2125786T3/pl unknown
- 2007-12-03 DK DK07858987.6T patent/DK2125786T3/da active
- 2007-12-03 KR KR1020097015193A patent/KR20090092338A/ko not_active Ceased
- 2007-12-03 MX MX2009006528A patent/MX2009006528A/es active IP Right Grant
- 2007-12-03 AT AT07858987T patent/ATE502028T1/de active
- 2007-12-03 KR KR1020127009903A patent/KR20120043775A/ko not_active Ceased
- 2007-12-03 RU RU2009123347/04A patent/RU2430918C2/ru not_active IP Right Cessation
- 2007-12-03 PT PT07858987T patent/PT2125786E/pt unknown
- 2007-12-03 BR BRPI0720936-3A patent/BRPI0720936A2/pt not_active IP Right Cessation
- 2007-12-03 ES ES07858987T patent/ES2360014T3/es active Active
- 2007-12-03 NZ NZ577716A patent/NZ577716A/xx not_active IP Right Cessation
- 2007-12-03 WO PCT/IB2007/003819 patent/WO2008084299A1/en not_active Ceased
- 2007-12-03 US US12/515,612 patent/US8283471B2/en not_active Expired - Fee Related
- 2007-12-03 DE DE602007013294T patent/DE602007013294D1/de active Active
- 2007-12-18 AR ARP070105692A patent/AR064417A1/es not_active Application Discontinuation
- 2007-12-19 JP JP2007327323A patent/JP5254602B2/ja not_active Expired - Fee Related
- 2007-12-20 TW TW096148920A patent/TWI359660B/zh not_active IP Right Cessation
-
2009
- 2009-06-16 IL IL199389A patent/IL199389A/en active IP Right Review Request
- 2009-06-17 ZA ZA200904230A patent/ZA200904230B/xx unknown
-
2011
- 2011-05-17 CY CY20111100481T patent/CY1111919T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2673435C (en) | 2012-10-09 |
| KR20090092338A (ko) | 2009-08-31 |
| BRPI0720936A2 (pt) | 2014-03-11 |
| AR064417A1 (es) | 2009-04-01 |
| ATE502028T1 (de) | 2011-04-15 |
| JP5254602B2 (ja) | 2013-08-07 |
| AU2007343135A1 (en) | 2008-07-17 |
| IL199389A (en) | 2014-01-30 |
| CN101611029A (zh) | 2009-12-23 |
| HK1134670A1 (en) | 2010-05-07 |
| EP2125786B1 (en) | 2011-03-16 |
| PL2125786T3 (pl) | 2011-07-29 |
| EP2125786A1 (en) | 2009-12-02 |
| SI2125786T1 (sl) | 2011-05-31 |
| MX2009006528A (es) | 2009-06-26 |
| WO2008084299A1 (en) | 2008-07-17 |
| NZ577716A (en) | 2012-10-26 |
| PT2125786E (pt) | 2011-04-21 |
| US20100063089A1 (en) | 2010-03-11 |
| CY1111919T1 (el) | 2015-11-04 |
| ES2360014T3 (es) | 2011-05-31 |
| RU2009123347A (ru) | 2011-01-27 |
| ZA200904230B (en) | 2010-04-28 |
| TW200833337A (en) | 2008-08-16 |
| AU2007343135B2 (en) | 2013-03-21 |
| JP2008208114A (ja) | 2008-09-11 |
| RU2430918C2 (ru) | 2011-10-10 |
| CA2673435A1 (en) | 2008-07-17 |
| DK2125786T3 (da) | 2011-05-09 |
| DE602007013294D1 (de) | 2011-04-28 |
| KR20120043775A (ko) | 2012-05-04 |
| CN101611029B (zh) | 2014-09-10 |
| US8283471B2 (en) | 2012-10-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3423443B1 (en) | Cyano-substituted indole compounds and uses thereof as lsd1 inhibitors | |
| JP7397452B2 (ja) | ヘテロアリールカルボキシアミド化合物 | |
| JP7710223B2 (ja) | 置換ピロロトリアジン系化合物およびその医薬組成物並びにそれらの使用 | |
| TW200538119A (en) | GSK-3 inhibitors | |
| CN115403626A (zh) | 新结晶形式 | |
| JP6928986B2 (ja) | キナーゼ活性を阻害するためのインダゾール系化合物、その組成物および使用 | |
| JP2009535321A (ja) | Gsk−3阻害剤としてのn−(2−チアゾリル)アミド誘導体 | |
| BR112021014977A2 (pt) | Derivados de acetamido como inibidores de dna polimerase teta | |
| CN105980389B (zh) | 一种jak激酶抑制剂的硫酸氢盐的结晶形式及其制备方法 | |
| JP2021519297A (ja) | Trkキナーゼ阻害剤としての大環状化合物 | |
| JPH11504905A (ja) | 新規複素環の化学 | |
| JP7018944B2 (ja) | PDE2阻害剤としての[1,2,4]トリアゾロ[1,5-a]ピリミジン化合物 | |
| JP5254602B2 (ja) | 2−((4−(1−メチル−4−(ピリジン−4−イル)−1h−ピラゾール−3−イル)フェノキシ)メチル)キノリンのコハク酸塩 | |
| WO2023093861A1 (zh) | Axl激酶抑制剂的单对甲苯磺酸盐及其晶型 | |
| CN111518082A (zh) | 一种氨基嘧啶类化合物及包含该化合物的组合物及其用途 | |
| EP2188290B1 (en) | Pyrazolo[3,4-d]-pyramidine derivatives as antiproliferative agents | |
| TW200927090A (en) | Novel sulfamate compounds for medical use | |
| WO2023093859A1 (zh) | Axl激酶抑制剂的盐、其制备方法和用途 | |
| CN117794913A (zh) | 嘧啶衍生物及其药学上可接受的盐的多晶型物和应用 | |
| EA043251B1 (ru) | Кристаллическая форма соединения для ингибирования активности cdk4/6 и ее применение | |
| CN118812503A (zh) | 作为aak1抑制剂的杂环类化合物 | |
| JP2021509398A (ja) | 二重作用fkbp12およびfkbp52阻害剤 | |
| HK1134670B (en) | Succinate salt of 2-((4-(1-methyl-4-(pyridin-4-yl)-1h-pyrazol-3-yl) phenoxy)methyl)quinoline |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |