JP2020510041A5 - - Google Patents
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- Publication number
- JP2020510041A5 JP2020510041A5 JP2019549366A JP2019549366A JP2020510041A5 JP 2020510041 A5 JP2020510041 A5 JP 2020510041A5 JP 2019549366 A JP2019549366 A JP 2019549366A JP 2019549366 A JP2019549366 A JP 2019549366A JP 2020510041 A5 JP2020510041 A5 JP 2020510041A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- formula
- carboxylic acid
- alkyl
- pyrazolo
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 33
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 10
- 230000003287 optical effect Effects 0.000 claims 7
- -1 piperidine-3-carboxylic acid (3R) -3-methyl-1-[(8R) -8- Methyl-2- [trans-4- (trifluoromethyl) cyclohexyl] -5H, 6H, 7H, 8H-pyrazolo [3,2-b] quinazoline-9-yl] piperidine-3-carboxylic acid Chemical compound 0.000 claims 7
- 229940002612 prodrug Drugs 0.000 claims 7
- 239000000651 prodrug Substances 0.000 claims 7
- AVJDMXZYANABIA-MHPIHPPYSA-N CC1=NC=2N(C(=C1C(C)C)N1C[C@](CCC1)(C(=O)O)CCC)N=C(C=2)[C@@H]1CC[C@H](CC1)C(F)(F)F Chemical compound CC1=NC=2N(C(=C1C(C)C)N1C[C@](CCC1)(C(=O)O)CCC)N=C(C=2)[C@@H]1CC[C@H](CC1)C(F)(F)F AVJDMXZYANABIA-MHPIHPPYSA-N 0.000 claims 6
- AWYMBGGHSHQBKP-DFFLPILJSA-N C[C@@]1(CCCN(C1)C1=C2CCOCC2=NC2=CC(=NN12)[C@H]1CC[C@@H](CC1)C(F)(F)F)C(O)=O Chemical compound C[C@@]1(CCCN(C1)C1=C2CCOCC2=NC2=CC(=NN12)[C@H]1CC[C@@H](CC1)C(F)(F)F)C(O)=O AWYMBGGHSHQBKP-DFFLPILJSA-N 0.000 claims 6
- 239000002207 metabolite Substances 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 150000004677 hydrates Chemical class 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 229940126027 positive allosteric modulator Drugs 0.000 claims 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 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 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 2
- 230000004048 modification Effects 0.000 claims 2
- 238000012986 modification Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- RUGCBFURIOPNHR-JOCHJYFZSA-N (3R)-1-[2-(4,4-difluorocyclohexyl)-5,6-diethylpyrazolo[1,5-a]pyrimidin-7-yl]-3-methylpiperidine-3-carboxylic acid Chemical compound FC1(CCC(CC1)C1=NN2C(N=C(C(=C2N2C[C@@](CCC2)(C(=O)O)C)CC)CC)=C1)F RUGCBFURIOPNHR-JOCHJYFZSA-N 0.000 claims 1
- UTYQOINWQJGILD-HSZRJFAPSA-N (3R)-1-[2-(4,4-difluorocyclohexyl)-5-methyl-6-propan-2-ylpyrazolo[1,5-a]pyrimidin-7-yl]-3-ethylpiperidine-3-carboxylic acid Chemical compound FC1(CCC(CC1)C1=NN2C(N=C(C(=C2N2C[C@@](CCC2)(C(=O)O)CC)C(C)C)C)=C1)F UTYQOINWQJGILD-HSZRJFAPSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- ZGAWLQDDQDAAFE-QQMNAOGKSA-N CC(C)C1=C(N2N=C(C=C2N=C1C)[C@H]1CC[C@@H](CC1)C(F)(F)F)N1CCC[C@@](C)(C1)C(O)=O Chemical compound CC(C)C1=C(N2N=C(C=C2N=C1C)[C@H]1CC[C@@H](CC1)C(F)(F)F)N1CCC[C@@](C)(C1)C(O)=O ZGAWLQDDQDAAFE-QQMNAOGKSA-N 0.000 claims 1
- DMFLJSHKIOZINU-BRWVUGGUSA-N CC(C)C1=C(N2N=C(C=C2N=C1C)[C@H]1CC[C@@H](CC1)C(F)(F)F)N1CCC[C@H](C1)C(O)=O Chemical compound CC(C)C1=C(N2N=C(C=C2N=C1C)[C@H]1CC[C@@H](CC1)C(F)(F)F)N1CCC[C@H](C1)C(O)=O DMFLJSHKIOZINU-BRWVUGGUSA-N 0.000 claims 1
- VIKYRFJZDYMDMY-CKNGIIGNSA-N CC(C)C1=C(N2N=C([C@H]3CC[C@@H](CC3)C(F)(F)F)C(F)=C2N=C1C)N1CCC[C@](C)(C1)C(O)=O Chemical compound CC(C)C1=C(N2N=C([C@H]3CC[C@@H](CC3)C(F)(F)F)C(F)=C2N=C1C)N1CCC[C@](C)(C1)C(O)=O VIKYRFJZDYMDMY-CKNGIIGNSA-N 0.000 claims 1
- AVJDMXZYANABIA-MPCDZSKCSA-N CC1=NC=2N(C(=C1C(C)C)N1C[C@@](CCC1)(C(=O)O)CCC)N=C(C=2)[C@@H]1CC[C@H](CC1)C(F)(F)F Chemical compound CC1=NC=2N(C(=C1C(C)C)N1C[C@@](CCC1)(C(=O)O)CCC)N=C(C=2)[C@@H]1CC[C@H](CC1)C(F)(F)F AVJDMXZYANABIA-MPCDZSKCSA-N 0.000 claims 1
- DMFLJSHKIOZINU-ULQDDVLXSA-N CC1=NC=2N(C(=C1C(C)C)N1C[C@H](CCC1)C(=O)O)N=C(C=2)[C@@H]1CC[C@H](CC1)C(F)(F)F Chemical compound CC1=NC=2N(C(=C1C(C)C)N1C[C@H](CCC1)C(=O)O)N=C(C=2)[C@@H]1CC[C@H](CC1)C(F)(F)F DMFLJSHKIOZINU-ULQDDVLXSA-N 0.000 claims 1
- SHIQMGZZVCRUAO-UAVUOLJFSA-N CC[C@@]1(CCCN(C1)C1=C(C(C)C)C(C)=NC2=C(F)C(=NN12)[C@H]1CC[C@@H](CC1)C(F)(F)F)C(O)=O Chemical compound CC[C@@]1(CCCN(C1)C1=C(C(C)C)C(C)=NC2=C(F)C(=NN12)[C@H]1CC[C@@H](CC1)C(F)(F)F)C(O)=O SHIQMGZZVCRUAO-UAVUOLJFSA-N 0.000 claims 1
- SADJPECUPDDDQB-WCJKSRRJSA-N CC[C@@]1(CCCN(C1)C1=C(OC)C(C)=NC2=CC(=NN12)[C@H]1CC[C@@H](CC1)C(F)(F)F)C(O)=O Chemical compound CC[C@@]1(CCCN(C1)C1=C(OC)C(C)=NC2=CC(=NN12)[C@H]1CC[C@@H](CC1)C(F)(F)F)C(O)=O SADJPECUPDDDQB-WCJKSRRJSA-N 0.000 claims 1
- SHIQMGZZVCRUAO-HOZJOUCCSA-N CC[C@]1(CCCN(C1)C1=C(C(C)C)C(C)=NC2=C(F)C(=NN12)[C@H]1CC[C@@H](CC1)C(F)(F)F)C(O)=O Chemical compound CC[C@]1(CCCN(C1)C1=C(C(C)C)C(C)=NC2=C(F)C(=NN12)[C@H]1CC[C@@H](CC1)C(F)(F)F)C(O)=O SHIQMGZZVCRUAO-HOZJOUCCSA-N 0.000 claims 1
- JKIFTUMUUABDBR-DOQJBMMISA-N C[C@@](CCC1)(CN1C1=C(COCC2)C2=NC2=CC([C@H](CC3)CC[C@@H]3C(F)(F)F)=NN12)C(O)=O Chemical compound C[C@@](CCC1)(CN1C1=C(COCC2)C2=NC2=CC([C@H](CC3)CC[C@@H]3C(F)(F)F)=NN12)C(O)=O JKIFTUMUUABDBR-DOQJBMMISA-N 0.000 claims 1
- AGPHNAQRSJNYHH-CKNGIIGNSA-N C[C@@]1(CN(CCC1)C=1N2C(N=C3CCCCC=13)=CC(=N2)[C@@H]1CC[C@H](CC1)C(F)(F)F)C(=O)O Chemical compound C[C@@]1(CN(CCC1)C=1N2C(N=C3CCCCC=13)=CC(=N2)[C@@H]1CC[C@H](CC1)C(F)(F)F)C(=O)O AGPHNAQRSJNYHH-CKNGIIGNSA-N 0.000 claims 1
- DRENYLRLZYSFGR-HOZJOUCCSA-N C[C@@]1(CN(CCC1)C=1N2N=C(C=C2N=C2CCCCCC=12)[C@@H]1CC[C@H](CC1)C(F)(F)F)C(=O)O Chemical compound C[C@@]1(CN(CCC1)C=1N2N=C(C=C2N=C2CCCCCC=12)[C@@H]1CC[C@H](CC1)C(F)(F)F)C(=O)O DRENYLRLZYSFGR-HOZJOUCCSA-N 0.000 claims 1
- 206010011224 Cough Diseases 0.000 claims 1
- 206010013654 Drug abuse Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 208000001914 Fragile X syndrome Diseases 0.000 claims 1
- 206010020710 Hyperphagia Diseases 0.000 claims 1
- 208000008238 Muscle Spasticity Diseases 0.000 claims 1
- 206010052904 Musculoskeletal stiffness Diseases 0.000 claims 1
- 208000029726 Neurodevelopmental disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 150000007960 acetonitrile Chemical class 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000029560 autism spectrum disease Diseases 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 206010008129 cerebral palsy Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229940126523 co-drug Drugs 0.000 claims 1
- 229960003920 cocaine Drugs 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 201000006517 essential tremor Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 201000010901 lateral sclerosis Diseases 0.000 claims 1
- 210000000111 lower esophageal sphincter Anatomy 0.000 claims 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical class N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 208000005264 motor neuron disease Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 230000001123 neurodevelopmental effect Effects 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 235000020830 overeating Nutrition 0.000 claims 1
- 208000019906 panic disease Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 210000002027 skeletal muscle Anatomy 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 208000018198 spasticity Diseases 0.000 claims 1
- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
- 208000009935 visceral pain Diseases 0.000 claims 1
- 0 *C(*)(CC1)CCC1c1n[n]c(N)c1* Chemical compound *C(*)(CC1)CCC1c1n[n]c(N)c1* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU1700108A HU231058B1 (hu) | 2017-03-13 | 2017-03-13 | Gyógyászatilag hatékony aliciklusos-szubsztituált pirazolo[1,5-a]pirimidin származékok |
| HUP1700108 | 2017-03-13 | ||
| PCT/IB2018/051599 WO2018167630A1 (en) | 2017-03-13 | 2018-03-12 | PHARMACOLOGICALLY ACTIVE ALICYCLIC-SUBSTITUTED PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVES |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020510041A JP2020510041A (ja) | 2020-04-02 |
| JP2020510041A5 true JP2020510041A5 (enExample) | 2021-02-12 |
| JP7153662B2 JP7153662B2 (ja) | 2022-10-14 |
Family
ID=89992389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019549366A Active JP7153662B2 (ja) | 2017-03-13 | 2018-03-12 | 薬理学的に活性な脂環式置換ピラゾロ［１，５－ａ］ピリミジン誘導体 |
Country Status (32)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT3595665T (pt) | 2017-03-13 | 2024-11-21 | Lundbeck La Jolla Research Center Inc | Inibidores duplos de magl e faah |
| HU231057B1 (hu) | 2017-03-13 | 2020-04-28 | Richter Gedeon Nyrt | Gyógyászatilag hatékony aril-szubsztituált pirazolo[1,5-a]pirimidin származékok |
| US12649738B2 (en) | 2020-03-26 | 2026-06-09 | Richter Gedeon Nyrt. | 1,3-dihydro-2H-pyrrolo[3,4-c]pyridine derivatives as GABAA α5 receptor modulators |
| TWI901650B (zh) | 2020-03-26 | 2025-10-21 | 匈牙利商羅特格登公司 | 啶及吡啶并〔３，４－ｃ〕嗒衍生物 |
| WO2021239558A1 (en) | 2020-05-27 | 2021-12-02 | Esteve Pharmaceuticals, S.A. | Pyrazolo[1,5-a]pyrimidine derivatives having multimodal activity against pain |
| TWI907472B (zh) | 2020-08-05 | 2025-12-11 | 匈牙利商羅特格登公司 | 具藥理活性之經雜環取代的吡唑并〔１，５－ａ〕嘧啶衍生物 |
| HU231691B1 (hu) | 2021-09-29 | 2025-10-28 | Richter Gedeon Nyrt | GABAA ALFA5 receptor modulátor hatású biciklusos aminszármazékok |
| CN115872095A (zh) * | 2022-11-28 | 2023-03-31 | 南通三鑫车灯配件有限公司 | 一种汽车车灯反光罩的生产线流转装置 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0508310A (pt) | 2004-03-02 | 2007-07-24 | Hoffmann La Roche | derivados de 4-(sulfanil-pirimidin-4-ilmetil)-morfolina e compostos relacionados como ligandos do receptor gaba, para o tratamento de ansiedade, depressão e epilepsia |
| GB0512844D0 (en) | 2005-06-23 | 2005-08-03 | Novartis Ag | Organic compounds |
| KR100753017B1 (ko) * | 2006-05-25 | 2007-08-30 | 한국화학연구원 | 7-(3,4-디알콕시페닐)-피라졸로[1,5-ａ]피리미딘 화합물을포함하는 관절염, 아토피 피부염, 백혈병을 포함한 암 및알쯔하이머, 우울증 또는 기억력 감소 등의 뇌질환의 치료및 예방을 위한 약제학적 조성물 |
| WO2009123986A1 (en) * | 2008-03-31 | 2009-10-08 | Takeda Pharmaceutical Company Limited | Apoptosis signal-regulating kinase 1 inhibitors |
| TWI648281B (zh) | 2013-10-17 | 2019-01-21 | 日商安斯泰來製藥股份有限公司 | 含硫二環式化合物 |
| WO2016169995A1 (en) * | 2015-04-20 | 2016-10-27 | AbbVie Deutschland GmbH & Co. KG | Substituted pyrazolopyrimidines and method of use |
| JP2018199623A (ja) * | 2015-10-22 | 2018-12-20 | 大正製薬株式会社 | 含窒素縮合複素環化合物 |
| HU231057B1 (hu) | 2017-03-13 | 2020-04-28 | Richter Gedeon Nyrt | Gyógyászatilag hatékony aril-szubsztituált pirazolo[1,5-a]pirimidin származékok |
-
2017
- 2017-03-13 HU HU1700108A patent/HU231058B1/hu not_active IP Right Cessation
-
2018
- 2018-03-12 US US16/493,453 patent/US11026946B2/en active Active
- 2018-03-12 MY MYPI2019004947A patent/MY195262A/en unknown
- 2018-03-12 JP JP2019549366A patent/JP7153662B2/ja active Active
- 2018-03-12 GE GEAP201815192A patent/GEP20217256B/en unknown
- 2018-03-12 PL PL18713016T patent/PL3596080T3/pl unknown
- 2018-03-12 SG SG11201907864YA patent/SG11201907864YA/en unknown
- 2018-03-12 CA CA3056185A patent/CA3056185A1/en active Pending
- 2018-03-12 HU HUE18713016A patent/HUE056562T2/hu unknown
- 2018-03-12 HR HRP20211850TT patent/HRP20211850T1/hr unknown
- 2018-03-12 ES ES18713016T patent/ES2893824T3/es active Active
- 2018-03-12 EA EA201992127A patent/EA038756B1/ru unknown
- 2018-03-12 WO PCT/IB2018/051599 patent/WO2018167630A1/en not_active Ceased
- 2018-03-12 UA UAA201910328A patent/UA124783C2/uk unknown
- 2018-03-12 SI SI201830495T patent/SI3596080T1/sl unknown
- 2018-03-12 CN CN201880017859.XA patent/CN110431142A/zh active Pending
- 2018-03-12 LT LTEPPCT/IB2018/051599T patent/LT3596080T/lt unknown
- 2018-03-12 PT PT18713016T patent/PT3596080T/pt unknown
- 2018-03-12 BR BR112019018843A patent/BR112019018843A2/pt not_active Application Discontinuation
- 2018-03-12 PE PE2019001773A patent/PE20191646A1/es unknown
- 2018-03-12 EP EP18713016.6A patent/EP3596080B1/en active Active
- 2018-03-12 RS RS20211334A patent/RS62533B1/sr unknown
- 2018-03-12 DK DK18713016.6T patent/DK3596080T3/da active
- 2018-03-12 KR KR1020197028833A patent/KR20190127779A/ko not_active Ceased
- 2018-03-12 MX MX2019011000A patent/MX2019011000A/es unknown
- 2018-03-12 AU AU2018235266A patent/AU2018235266B2/en not_active Ceased
- 2018-03-13 AR ARP180100580A patent/AR111176A1/es unknown
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2019
- 2019-08-26 IL IL26892319A patent/IL268923A/en unknown
- 2019-08-27 PH PH12019501968A patent/PH12019501968A1/en unknown
- 2019-09-12 CL CL2019002601A patent/CL2019002601A1/es unknown
- 2019-09-18 CO CONC2019/0010120A patent/CO2019010120A2/es unknown
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2021
- 2021-11-08 CY CY20211100964T patent/CY1124708T1/el unknown
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