ES2980131T3 - Agente terapéutico para la demencia que combina derivado de pirazoloquinolina y donepezilo - Google Patents
Agente terapéutico para la demencia que combina derivado de pirazoloquinolina y donepezilo Download PDFInfo
- Publication number
- ES2980131T3 ES2980131T3 ES18810578T ES18810578T ES2980131T3 ES 2980131 T3 ES2980131 T3 ES 2980131T3 ES 18810578 T ES18810578 T ES 18810578T ES 18810578 T ES18810578 T ES 18810578T ES 2980131 T3 ES2980131 T3 ES 2980131T3
- Authority
- ES
- Spain
- Prior art keywords
- pharmaceutically acceptable
- acceptable salt
- donepezil
- disease
- tetrahydrofuran
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 title claims abstract description 82
- 229960003530 donepezil Drugs 0.000 title claims abstract description 41
- 239000003814 drug Substances 0.000 title claims abstract description 39
- 229940124597 therapeutic agent Drugs 0.000 title claims abstract description 34
- 206010012289 Dementia Diseases 0.000 title description 11
- UXYHZIYEDDINQH-UHFFFAOYSA-N C1=CNC2=C3C=NN=C3C=CC2=C1 Chemical class C1=CNC2=C3C=NN=C3C=CC2=C1 UXYHZIYEDDINQH-UHFFFAOYSA-N 0.000 title description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 93
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 52
- CKJDCNZBABIEBZ-HNNXBMFYSA-N 7-(2-methoxy-3,5-dimethylpyridin-4-yl)-1-[(3S)-oxolan-3-yl]-5H-pyrazolo[4,3-c]quinolin-4-one Chemical compound COC1=NC=C(C)C(C=2C=C3NC(=O)C=4C=NN(C=4C3=CC=2)[C@@H]2COCC2)=C1C CKJDCNZBABIEBZ-HNNXBMFYSA-N 0.000 claims abstract description 26
- 201000002832 Lewy body dementia Diseases 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims description 33
- 229960003135 donepezil hydrochloride Drugs 0.000 claims description 21
- XWAIAVWHZJNZQQ-UHFFFAOYSA-N donepezil hydrochloride Chemical compound [H+].[Cl-].O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 XWAIAVWHZJNZQQ-UHFFFAOYSA-N 0.000 claims description 21
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 14
- AFKSGMDXSLTKSU-DASCVMRKSA-N (Z)-but-2-enedioic acid 7-(2-methoxy-3,5-dimethylpyridin-4-yl)-1-[(3S)-oxolan-3-yl]-5H-pyrazolo[4,3-c]quinolin-4-one Chemical compound OC(=O)\C=C/C(O)=O.COc1ncc(C)c(c1C)-c1ccc2c3n(ncc3c(=O)[nH]c2c1)[C@H]1CCOC1 AFKSGMDXSLTKSU-DASCVMRKSA-N 0.000 claims description 11
- 208000009829 Lewy Body Disease Diseases 0.000 abstract description 6
- 230000000694 effects Effects 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- 241000700159 Rattus Species 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 10
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 10
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 10
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 10
- 229960002646 scopolamine Drugs 0.000 description 10
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 description 9
- 239000008194 pharmaceutical composition Substances 0.000 description 9
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 7
- 229960004640 memantine Drugs 0.000 description 7
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- -1 inorganic acid salts Chemical class 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- 101001117256 Drosophila melanogaster High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A Proteins 0.000 description 5
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 5
- 229960004373 acetylcholine Drugs 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 208000010877 cognitive disease Diseases 0.000 description 4
- 230000003920 cognitive function Effects 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 208000028698 Cognitive impairment Diseases 0.000 description 3
- 206010052804 Drug tolerance Diseases 0.000 description 3
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 230000006399 behavior Effects 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 229960003980 galantamine Drugs 0.000 description 3
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 description 3
- 230000026781 habituation Effects 0.000 description 3
- 210000000653 nervous system Anatomy 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 229960004136 rivastigmine Drugs 0.000 description 3
- 206010001497 Agitation Diseases 0.000 description 2
- 208000000044 Amnesia Diseases 0.000 description 2
- 208000031091 Amnestic disease Diseases 0.000 description 2
- 208000036574 Behavioural and psychiatric symptoms of dementia Diseases 0.000 description 2
- 108090000371 Esterases Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 230000006986 amnesia Effects 0.000 description 2
- 238000011284 combination treatment Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical group OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 206010000117 Abnormal behaviour Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 206010002942 Apathy Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010012218 Delirium Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010013142 Disinhibition Diseases 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 208000004547 Hallucinations Diseases 0.000 description 1
- 101000604027 Homo sapiens Nuclear protein localization protein 4 homolog Proteins 0.000 description 1
- 101000974007 Homo sapiens Nucleosome assembly protein 1-like 3 Proteins 0.000 description 1
- 101001099181 Homo sapiens TATA-binding protein-associated factor 2N Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 206010024642 Listless Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 1
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 1
- 229940099433 NMDA receptor antagonist Drugs 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 102100038438 Nuclear protein localization protein 4 homolog Human genes 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 102100038917 TATA-binding protein-associated factor 2N Human genes 0.000 description 1
- 230000001594 aberrant effect Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000006999 cognitive decline Effects 0.000 description 1
- 230000037411 cognitive enhancing Effects 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000021824 exploration behavior Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 208000017971 listlessness Diseases 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000013289 male long evans rat Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- NRNCYVBFPDDJNE-UHFFFAOYSA-N pemoline Chemical compound O1C(N)=NC(=O)C1C1=CC=CC=C1 NRNCYVBFPDDJNE-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011870 unpaired t-test Methods 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
- A61K31/435—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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762513692P | 2017-06-01 | 2017-06-01 | |
| PCT/JP2018/020638 WO2018221545A1 (ja) | 2017-06-01 | 2018-05-30 | ピラゾロキノリン誘導体とドネペジルの併用による認知症治療剤 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2980131T3 true ES2980131T3 (es) | 2024-09-30 |
Family
ID=64455958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES18810578T Active ES2980131T3 (es) | 2017-06-01 | 2018-05-30 | Agente terapéutico para la demencia que combina derivado de pirazoloquinolina y donepezilo |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US11833146B2 (https=) |
| EP (1) | EP3632439B1 (https=) |
| JP (2) | JP7079777B2 (https=) |
| KR (1) | KR102627787B1 (https=) |
| CN (1) | CN110603040B (https=) |
| AU (1) | AU2018276565A1 (https=) |
| BR (1) | BR112019023569A2 (https=) |
| CA (1) | CA3060030A1 (https=) |
| ES (1) | ES2980131T3 (https=) |
| IL (1) | IL270395B (https=) |
| RU (1) | RU2019135834A (https=) |
| SG (2) | SG11201909595VA (https=) |
| WO (1) | WO2018221545A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018221550A1 (ja) | 2017-06-01 | 2018-12-06 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ピラゾロキノリン誘導体とメマンチンの併用による認知症治療剤 |
| BR112019023552A2 (pt) | 2017-06-01 | 2020-06-02 | Eisai R&D Management Co., Ltd. | Agente terapêutico para a demência com corpos de lewy contendo derivado de pirazoloquinolina |
| KR20200010211A (ko) | 2017-06-01 | 2020-01-30 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | Pde9 저해제를 포함하는 약제학적 조성물 |
| KR102271305B1 (ko) | 2020-05-21 | 2021-06-30 | 주식회사 아리바이오 | 치매 예방 및 치료용 조성물 |
| KR102272907B1 (ko) | 2020-11-05 | 2021-07-05 | 주식회사 아리바이오 | 치매 예방 및 치료용 조성물 |
| KR102272910B1 (ko) | 2021-01-28 | 2021-07-06 | 주식회사 아리바이오 | 당뇨병을 동반한 치매 예방 및 치료용 조성물 |
| KR20220140960A (ko) | 2021-04-12 | 2022-10-19 | 주식회사 아리바이오 | 당뇨병을 동반한 치매 예방 및 치료용 조성물 |
| KR102311224B1 (ko) * | 2021-04-23 | 2021-10-13 | 주식회사 아리바이오 | Pde5 억제제와 글루코코르티코이드 수용체 길항제 병용투여를 통한 치매 예방 및 치료용 조성물 |
| KR20220146095A (ko) | 2021-04-23 | 2022-11-01 | 주식회사 아리바이오 | Pde5 억제제와 글루코코르티코이드 수용체 길항제 병용투여를 통한 치매 예방 및 치료용 조성물 |
| WO2023064857A1 (en) | 2021-10-14 | 2023-04-20 | Incyte Corporation | Quinoline compounds as inhibitors of kras |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05132484A (ja) | 1991-04-26 | 1993-05-28 | Otsuka Pharmaceut Factory Inc | ピラゾロキノリン及びピラゾロナフチリジン誘導体 |
| DK0760819T3 (da) | 1994-05-24 | 2000-10-09 | Hoffmann La Roche | Tricykliske dicarbonylderivater |
| GB9612710D0 (en) * | 1996-06-18 | 1996-08-21 | Pfizer Ltd | Method of treatment |
| WO1998030243A1 (en) * | 1997-01-08 | 1998-07-16 | Warner-Lambert Company | Acetylcholinesterase inhibitors in combination with muscarinic agonists for the treatment of alzheimer's disease |
| US5962535A (en) * | 1997-01-17 | 1999-10-05 | Takeda Chemical Industries, Ltd. | Composition for alzheimer's disease |
| HN2002000317A (es) | 2001-11-02 | 2003-05-21 | Pfizer | Inhibidores de pde9 para tratamiento de trastornos cardiovasculares |
| BR0313262A (pt) | 2002-08-07 | 2005-07-12 | Mitsubishi Pharma Corp | Compostos de dihidropirazolpiridina |
| DE10238722A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse |
| DE102004004142A1 (de) | 2003-05-09 | 2004-11-25 | Bayer Healthcare Ag | 6-Cyclylmethyl- und 6-Alkylmethyl-substituierte Pyrazolopyrimidine |
| RU2426734C2 (ru) | 2003-10-03 | 2011-08-20 | Зм Инновейтив Пропертиз Компани | Пиразолопиридины и их аналоги |
| WO2005118583A1 (en) | 2004-05-28 | 2005-12-15 | Millennium Pharmaceuticals, Inc. | 2, 5-dihydro-pyrazolo`4, 3-c!quinolin-4-ones as chk-1 inhibitors |
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- 2018-05-30 CA CA3060030A patent/CA3060030A1/en active Pending
- 2018-05-30 CN CN201880030220.5A patent/CN110603040B/zh active Active
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- 2018-05-30 JP JP2019521248A patent/JP7079777B2/ja active Active
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| SG11201909595VA (en) | 2019-11-28 |
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| IL270395B (en) | 2022-08-01 |
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| SG10202113198TA (en) | 2021-12-30 |
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| CN110603040A (zh) | 2019-12-20 |
| CN110603040B (zh) | 2023-02-28 |
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| EP3632439A1 (en) | 2020-04-08 |
| WO2018221545A1 (ja) | 2018-12-06 |
| US11833146B2 (en) | 2023-12-05 |
| BR112019023569A2 (pt) | 2020-06-02 |
| CA3060030A1 (en) | 2018-12-06 |
| JPWO2018221545A1 (ja) | 2020-04-02 |
| AU2018276565A1 (en) | 2019-11-07 |
| EP3632439A4 (en) | 2021-02-17 |
| RU2019135834A3 (https=) | 2021-10-15 |
| JP2022110143A (ja) | 2022-07-28 |
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