PE20191323A1 - PIRAZOLO[3,4-b]PIRIDINAS E IMIDAZO[1,5-b]PIRIDAZINAS COMO INHIBIDORES DE PDE1 - Google Patents
PIRAZOLO[3,4-b]PIRIDINAS E IMIDAZO[1,5-b]PIRIDAZINAS COMO INHIBIDORES DE PDE1Info
- Publication number
- PE20191323A1 PE20191323A1 PE2019001294A PE2019001294A PE20191323A1 PE 20191323 A1 PE20191323 A1 PE 20191323A1 PE 2019001294 A PE2019001294 A PE 2019001294A PE 2019001294 A PE2019001294 A PE 2019001294A PE 20191323 A1 PE20191323 A1 PE 20191323A1
- Authority
- PE
- Peru
- Prior art keywords
- pyrazolo
- methyl
- branched
- alkyl
- linear
- Prior art date
Links
- 229940121836 Phosphodiesterase 1 inhibitor Drugs 0.000 title 1
- 150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 title 1
- 150000004892 pyridazines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- FOVDMANDBXNDTK-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(1-methylimidazol-4-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC=1N=CN(C=1)C FOVDMANDBXNDTK-UHFFFAOYSA-N 0.000 abstract 1
- WYHCKHHDBOXJTM-UHFFFAOYSA-N 6-(2-ethoxypyridin-3-yl)-1-methyl-N-[(2-methyl-1,3-oxazol-4-yl)methyl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-4-amine Chemical compound C(C)OC1=NC=CC=C1C=1C=C(C2=C(N=1)N(N=C2C(C)C)C)NCC=1N=C(OC=1)C WYHCKHHDBOXJTM-UHFFFAOYSA-N 0.000 abstract 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 208000015122 neurodegenerative disease Diseases 0.000 abstract 1
- 230000000626 neurodegenerative effect Effects 0.000 abstract 1
- 125000003566 oxetanyl group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 208000020016 psychiatric disease Diseases 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 abstract 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/502—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with carbocyclic ring systems, e.g. cinnoline, phthalazine
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- 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
- A61P25/28—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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Referido a un compuesto de formula I y sales aceptables del mismo, donde: Y1 = N-R1, Y2 = C e Y3 = C, o Y1 = C-R1, Y2 = N e Y3 = C; Z1 se selecciona de NH, CH2 , O y S; Z2 se selecciona entre NH, CH2 , O y S; R1 es hidrogeno, alquilo C1-4 lineal o ramificado y cicloalquilo C3-4 monociclico saturado, opcionalmente sustituido con uno o mas halogenos; R2 es alquilo C1-6 lineal o ramificado, cicloalquilo C3-6 monociclico saturado, oxetanilo, tetrahidrofuranilo y tetrahidropiranilo, todos opcionalmente sustituidos con uno o mas halogenos; R3 es un heteroarilo de 5 o 6 miembros, que puede estar opcionalmente sustituido con uno o mas sustituyentes seleccionados de alquilo C1-4 lineal o ramificado, entre otros; y R4 es un heteroarilo de 5 o 6 miembros. Son compuestos preferidos: 6-(2-etoxi-3-piridil)-3-isopropil-1-metil-N-[(1-metilimidazol-4-il) metil]pirazolo[3,4-b]piridin-4-amina; 6-(2-etoxi-3-piridil)-3-isopropil-1-metil-N-[(2-metiloxazol-4-il)metil]pirazolo[3,4-b]piridin-4-amina; entre otros. Dichos compuestos son inhibidores de la enzima fosfodiesterasa tipo 1 (PDE1), utiles en el tratamiento de trastornos neurodegenerativos y psiquiatricos. Tambien se refiere a una composicion farmaceutica que comprende dichos compuestos.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA201600784 | 2016-12-22 | ||
| DKPA201700404 | 2017-07-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20191323A1 true PE20191323A1 (es) | 2019-09-24 |
Family
ID=60812077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2019001294A PE20191323A1 (es) | 2016-12-22 | 2017-12-20 | PIRAZOLO[3,4-b]PIRIDINAS E IMIDAZO[1,5-b]PIRIDAZINAS COMO INHIBIDORES DE PDE1 |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US10351561B2 (es) |
| EP (1) | EP3558988B1 (es) |
| JP (1) | JP7074758B2 (es) |
| KR (1) | KR20190095301A (es) |
| CN (1) | CN110099901B (es) |
| AU (1) | AU2017384481A1 (es) |
| BR (1) | BR112018017067A2 (es) |
| CA (1) | CA3046588A1 (es) |
| CL (1) | CL2019001669A1 (es) |
| CO (1) | CO2019005538A2 (es) |
| CR (1) | CR20190302A (es) |
| DO (1) | DOP2019000169A (es) |
| EC (1) | ECSP19043790A (es) |
| ES (1) | ES2882335T3 (es) |
| IL (1) | IL267561A (es) |
| JO (1) | JOP20190126A1 (es) |
| MX (1) | MX2019007509A (es) |
| PE (1) | PE20191323A1 (es) |
| PH (1) | PH12019501324A1 (es) |
| RU (1) | RU2019116251A (es) |
| TW (1) | TW201829405A (es) |
| WO (1) | WO2018115067A1 (es) |
| ZA (1) | ZA201904236B (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10034861B2 (en) | 2016-07-04 | 2018-07-31 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| JOP20190126A1 (ar) | 2016-12-22 | 2019-05-28 | H Lundbeck As | بيرازولو [3، 4-b] بيريدينات وإيميدازو [1، 5-b] بيريدازينات على هيئة مثبطات PDE1 |
| AR113926A1 (es) | 2017-12-14 | 2020-07-01 | H Lundbeck As | Derivados de 1h-pirazolo[4,3-b]piridinas |
| PT3723807T (pt) | 2017-12-14 | 2021-11-26 | H Lundbeck As | Tratamentos de associação que compreendem a administração de 1h-pirazolo[4,3-b]piridinas |
| CN117447475A (zh) | 2017-12-20 | 2024-01-26 | H.隆德贝克有限公司 | 作为PDE1抑制剂的吡唑并[4,3-b]吡啶和咪唑并[1,5-a]嘧啶 |
| TW201927784A (zh) | 2017-12-20 | 2019-07-16 | 丹麥商Ｈ 朗德貝克公司 | 作為pde1抑制劑之大環 |
| US10766893B2 (en) | 2017-12-20 | 2020-09-08 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| CA3162047A1 (en) * | 2019-12-23 | 2021-07-01 | Anthony Pinkerton | Ectonucleotide pyrophosphatase/phosphodiesterase 1 (enpp1) modulators and uses thereof |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6326379B1 (en) * | 1998-09-16 | 2001-12-04 | Bristol-Myers Squibb Co. | Fused pyridine inhibitors of cGMP phosphodiesterase |
| WO2006004188A1 (en) * | 2004-07-05 | 2006-01-12 | Astellas Pharma Inc. | Pyrazolopyridine derivatives |
| JP2008517060A (ja) | 2004-10-19 | 2008-05-22 | エスビー・ファルムコ・プエルト・リコ・インコーポレイテッド | Ｃｒｆ受容体アンタゴニストおよびその製法 |
| EP2089034A4 (en) | 2006-12-05 | 2010-07-28 | Intra Cellular Therapies Inc | NEW USES |
| NZ579645A (en) | 2007-03-14 | 2012-01-12 | Ranbaxy Lab Ltd | Pyrazolo (3, 4-b) pyridine derivatives as phosphodiesterase inhibitors |
| WO2009067607A2 (en) * | 2007-11-20 | 2009-05-28 | Memory Pharmaceuticals Corporation | Combinations of pde4 inhibitors and antipsychotics for the treatment of psychotic disorders |
| BRPI0922700A2 (pt) * | 2008-12-06 | 2015-08-11 | Intracellular Therapies Inc | Compostos orgânicos |
| CN104379578B (zh) | 2012-03-19 | 2017-06-09 | 阿比德治疗公司 | 氨基甲酸酯化合物及其制备和使用方法 |
| TW201533043A (zh) * | 2013-04-18 | 2015-09-01 | Lundbeck & Co As H | 作爲ｌｒｒｋ２抑制劑的芳基吡咯并吡啶衍生化合物 |
| US20160083400A1 (en) | 2014-09-18 | 2016-03-24 | Sunovion Pharmaceuticals Inc. | Tricyclic guanidine derivative |
| JP2017527606A (ja) | 2014-09-18 | 2017-09-21 | サノビオン ファーマシューティカルズ インクＳｕｎｏｖｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | 三環系誘導体 |
| US20160083391A1 (en) | 2014-09-18 | 2016-03-24 | Sunovion Pharmaceuticals Inc. | Tricyclic piperazine derivative |
| TW201629064A (zh) | 2014-10-10 | 2016-08-16 | Ｈ 朗德貝克公司 | 作爲ｐｄｅ１抑制劑之三唑並吡酮 |
| WO2016147659A1 (en) | 2015-03-16 | 2016-09-22 | Sumitomo Dainippon Pharma Co., Ltd. | Bicyclic imidazolo derivative |
| TW201643167A (zh) * | 2015-04-22 | 2016-12-16 | Ｈ 朗德貝克公司 | 作爲ｐｄｅ１抑制劑之咪唑並三酮 |
| JO3627B1 (ar) | 2015-04-30 | 2020-08-27 | H Lundbeck As | إيميدازو بيرازينونات على هيئة مثبطات pde1 |
| WO2017172795A1 (en) | 2016-03-28 | 2017-10-05 | Intra-Cellular Therapies, Inc. | Novel compositions and methods |
| US10034861B2 (en) | 2016-07-04 | 2018-07-31 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| JOP20190126A1 (ar) | 2016-12-22 | 2019-05-28 | H Lundbeck As | بيرازولو [3، 4-b] بيريدينات وإيميدازو [1، 5-b] بيريدازينات على هيئة مثبطات PDE1 |
| TW201927784A (zh) | 2017-12-20 | 2019-07-16 | 丹麥商Ｈ 朗德貝克公司 | 作為pde1抑制劑之大環 |
| US10766893B2 (en) | 2017-12-20 | 2020-09-08 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
-
2017
- 2017-06-16 JO JOP/2019/0126A patent/JOP20190126A1/ar unknown
- 2017-12-19 TW TW106144606A patent/TW201829405A/zh unknown
- 2017-12-20 BR BR112018017067A patent/BR112018017067A2/pt not_active Application Discontinuation
- 2017-12-20 AU AU2017384481A patent/AU2017384481A1/en not_active Abandoned
- 2017-12-20 PE PE2019001294A patent/PE20191323A1/es unknown
- 2017-12-20 CA CA3046588A patent/CA3046588A1/en not_active Abandoned
- 2017-12-20 JP JP2019534197A patent/JP7074758B2/ja active Active
- 2017-12-20 RU RU2019116251A patent/RU2019116251A/ru not_active Application Discontinuation
- 2017-12-20 EP EP17821622.2A patent/EP3558988B1/en active Active
- 2017-12-20 CN CN201780079553.2A patent/CN110099901B/zh not_active Expired - Fee Related
- 2017-12-20 MX MX2019007509A patent/MX2019007509A/es unknown
- 2017-12-20 WO PCT/EP2017/083721 patent/WO2018115067A1/en not_active Ceased
- 2017-12-20 KR KR1020197017840A patent/KR20190095301A/ko not_active Ceased
- 2017-12-20 ES ES17821622T patent/ES2882335T3/es active Active
- 2017-12-20 CR CR20190302A patent/CR20190302A/es unknown
- 2017-12-21 US US15/849,798 patent/US10351561B2/en active Active
-
2019
- 2019-05-28 CO CONC2019/0005538A patent/CO2019005538A2/es unknown
- 2019-05-29 US US16/424,585 patent/US10689379B2/en active Active
- 2019-06-11 PH PH12019501324A patent/PH12019501324A1/en unknown
- 2019-06-17 CL CL2019001669A patent/CL2019001669A1/es unknown
- 2019-06-18 DO DO2019000169A patent/DOP2019000169A/es unknown
- 2019-06-19 EC ECSENADI201943790A patent/ECSP19043790A/es unknown
- 2019-06-20 IL IL267561A patent/IL267561A/en unknown
- 2019-06-27 ZA ZA2019/04236A patent/ZA201904236B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2019007509A (es) | 2019-09-04 |
| CN110099901B (zh) | 2023-01-03 |
| US10689379B2 (en) | 2020-06-23 |
| ECSP19043790A (es) | 2019-06-30 |
| JP7074758B2 (ja) | 2022-05-24 |
| ES2882335T3 (es) | 2021-12-01 |
| JP2020502230A (ja) | 2020-01-23 |
| CO2019005538A2 (es) | 2019-06-11 |
| KR20190095301A (ko) | 2019-08-14 |
| TW201829405A (zh) | 2018-08-16 |
| CR20190302A (es) | 2019-08-21 |
| WO2018115067A1 (en) | 2018-06-28 |
| DOP2019000169A (es) | 2019-07-31 |
| RU2019116251A3 (es) | 2021-03-31 |
| RU2019116251A (ru) | 2021-01-22 |
| ZA201904236B (en) | 2020-12-23 |
| CL2019001669A1 (es) | 2019-09-06 |
| US10351561B2 (en) | 2019-07-16 |
| EP3558988A1 (en) | 2019-10-30 |
| JOP20190126A1 (ar) | 2019-05-28 |
| IL267561A (en) | 2019-08-29 |
| US20190352302A1 (en) | 2019-11-21 |
| PH12019501324A1 (en) | 2019-09-16 |
| CN110099901A (zh) | 2019-08-06 |
| BR112018017067A2 (pt) | 2019-07-02 |
| US20180179200A1 (en) | 2018-06-28 |
| CA3046588A1 (en) | 2018-06-28 |
| EP3558988B1 (en) | 2021-07-07 |
| AU2017384481A1 (en) | 2019-06-13 |
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