AR082661A1 - DERIVADOS DE 6,7-DIHIDRO-3H-OXAZOLO[3,4-a]PIRAZIN-5,8-DIONA - Google Patents
DERIVADOS DE 6,7-DIHIDRO-3H-OXAZOLO[3,4-a]PIRAZIN-5,8-DIONAInfo
- Publication number
- AR082661A1 AR082661A1 ARP110102892A ARP110102892A AR082661A1 AR 082661 A1 AR082661 A1 AR 082661A1 AR P110102892 A ARP110102892 A AR P110102892A AR P110102892 A ARP110102892 A AR P110102892A AR 082661 A1 AR082661 A1 AR 082661A1
- Authority
- AR
- Argentina
- Prior art keywords
- heteroatoms
- alkyl
- positions
- optionally substituted
- cycloalkyl
- Prior art date
Links
- 125000005842 heteroatom Chemical group 0.000 abstract 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 2
- 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- -1 1H-indole-3-yl Chemical group 0.000 abstract 1
- DRJBVJCTNYPBHF-UHFFFAOYSA-N 3H-[1,3]oxazolo[3,4-a]pyrazine-5,8-dione Chemical compound O=C1C=NC(=O)C2=COCN12 DRJBVJCTNYPBHF-UHFFFAOYSA-N 0.000 abstract 1
- SPNMSIYOCYTIIH-UHFFFAOYSA-N 6,7-dihydro-3h-[1,3]oxazolo[3,4-a]pyrazine-5,8-dione Chemical class O=C1CNC(=O)C2=COCN12 SPNMSIYOCYTIIH-UHFFFAOYSA-N 0.000 abstract 1
- 208000010228 Erectile Dysfunction Diseases 0.000 abstract 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract 1
- 125000005090 alkenylcarbonyl group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 125000004404 heteroalkyl group Chemical group 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 201000001881 impotence Diseases 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 229940124549 vasodilator Drugs 0.000 abstract 1
- 239000003071 vasodilator agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—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
- A61K31/495—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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/04—Drugs for disorders of the urinary system for urolithiasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D503/02—Preparation
- C07D503/04—Preparation by forming the ring or condensed ring systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Molecular Biology (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Describe una serie de derivados de 6,7-dihidro-3H-oxazolo[3,4-a]pirazin-5,8-diona, sus mezclas, sus sales farmacéuticamente aceptables, que son inhibidores de PDE-5, que poseen propiedades vasodilatadoras y efectos de relajación. En particular, el derivado (R)-3-(1,3-dibenzodioxol-5-il)-1-(1H-indol-3-il)-7-metil-6,7-dihidro[1,3]oxazolo[3,4-a]pirazin-5,8-diona, su enantiómero (S)-3-(1,3-dibenzodioxol-5-il)-1-(1H-indol-3-il)-7-metil-6,7-dihidro[1,3]oxazolo[3,4-a]pirazin-5,8-diona. Describe además, procesos para la preparación de dichos compuestos, composiciones farmacéuticas que los contienen, así como usos como inhibidores de la enzima fosfodiesterasa de tipo 5 (PDE-5) en el tratamiento de la disfunción eréctil y trastornos tratables con inhibidor de PDE-5.Reivindicación 1: Un compuesto de la fórmula (1) o sus sales, solvatos o hidratos; en donde R1 es un grupo aromático, opcionalmente condensado, opcionalmente sustituido con RB en una o más posiciones; un grupo heteroaromático que contiene uno o más heteroátomos, opcionalmente sustituido con RB o un grupo indol en una o más posiciones; un alquenil C1-6-carbonilo, opcionalmente sustituido con RB en una o más posiciones; un aromático bicíclico, opcionalmente sustituido con RB en una o más posiciones o un heteroaromático bicíclico que contiene uno o más heteroátomos, opcionalmente sustituido con RB en una o más posiciones; RB es un halógeno, hidroxilo, nitrógeno, ciano, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, cicloalquilo C3-8, cicloalquil C3-8-alquilo C1-3, arilalquilo C1-3 o heteroarilalquilo C1-3; R2 es un grupo aromático que contiene uno o más heteroátomos, un grupo heteroaromático que contiene uno o más heteroátomos o grupos metileno-3,4-dioxifenilo o uno aromático bicíclico que contiene uno o más heteroátomos o grupos metileno-3,4-dioxifenilo; R3 es hidrógeno, halógeno, haloalquilo C1-6, heteroalquilo C1-3, o alquilo C1-3; y R4 es hidrógeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, cicloalquilo C3-8, cicloalquil C3-8-alquilo C1-3, arilalquilo C1-3 o heteroarilalquilo C1-3.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37348310P | 2010-08-13 | 2010-08-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR082661A1 true AR082661A1 (es) | 2012-12-26 |
Family
ID=45023415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP110102892A AR082661A1 (es) | 2010-08-13 | 2011-08-09 | DERIVADOS DE 6,7-DIHIDRO-3H-OXAZOLO[3,4-a]PIRAZIN-5,8-DIONA |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8338432B2 (es) |
| EP (1) | EP2603512B1 (es) |
| JP (1) | JP5940535B2 (es) |
| KR (1) | KR101871856B1 (es) |
| CN (1) | CN103108878B (es) |
| AR (1) | AR082661A1 (es) |
| BR (1) | BR112013003225B1 (es) |
| CA (1) | CA2807872C (es) |
| CL (1) | CL2013000434A1 (es) |
| CO (1) | CO6680703A2 (es) |
| DK (1) | DK2603512T3 (es) |
| EC (1) | ECSP13012486A (es) |
| ES (1) | ES2565493T3 (es) |
| HU (1) | HUE027903T2 (es) |
| IL (1) | IL224683A (es) |
| MX (1) | MX347632B (es) |
| PL (1) | PL2603512T3 (es) |
| RU (1) | RU2581831C2 (es) |
| UY (1) | UY33535A (es) |
| WO (1) | WO2012019254A1 (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY33535A (es) * | 2010-08-13 | 2011-12-01 | Biolab Sanus Farmaceutuca Limitada | Derivados de 6,7-dihidro-3h-oxazolo[3,4]pirazin-5,8-diona |
| AR099523A1 (es) * | 2014-02-24 | 2016-07-27 | Biolab Sanus Farmacêutica Ltda | Compuestos derivados de 6,7-dihidro-3h-oxazolo[3,4-a]pirazina-5,8-diona |
| CN114751905A (zh) * | 2014-09-12 | 2022-07-15 | 生物实验萨纽斯药物有限公司 | 新的吡啶并嘧啶衍生物化合物、其药物组合物及其用途 |
| MX2021015425A (es) * | 2019-07-15 | 2022-02-21 | Biolab Sanus Farmaceutica Ltda | Estereoisomeros del compuesto 3-(benzo[d][1,3]dioxol-5-il)-7-(1-hi droxipropano-2-il)-1-(1h-indol-3-il)-6,7-dihidro-3h-oxazol[3,4-a] pirazina-5,8-diona y su uso como antitumoral y inhibidor de la enzima fosfodiesterasa. |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996026940A1 (en) | 1995-03-01 | 1996-09-06 | Kyowa Hakko Kogyo Co., Ltd. | Imidazoquinazoline derivatives |
| GB9514464D0 (en) | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Medicaments |
| MXPA03011082A (es) * | 2001-06-05 | 2004-07-08 | Lilly Icos Llc | Derivados de pirazino-1',2': 1,6-prirido-3,4-b-indol-1,4-diona. |
| CA2445189C (en) | 2001-06-21 | 2009-02-17 | Lilly Icos Llc | Carboline derivatives as pdev inhibitors |
| AR045950A1 (es) | 2003-10-09 | 2005-11-16 | Speedel Experimenta Ag | Compuestos derivados de piperazina, composiciones farmaceuticas que los contienen y su uso en la fabricacion de medicamentos. |
| CA2562251C (en) | 2004-04-07 | 2009-04-28 | Pfizer Inc. | Pyrazolo'4,3-d pyrimidines |
| RU2418590C2 (ru) * | 2006-04-04 | 2011-05-20 | Донг-А Фарматех Ко. Лтд. | Средство для предупреждения и лечения гиперплазии предстательной железы, содержащее производное пиразолопиримидинона |
| BRPI0903803B1 (pt) * | 2009-09-30 | 2019-07-09 | Biolab Sanus Farmacêutica Ltda. | Composto, processo de preparação, composição farmacêutica e uso dos compostos |
| UY33535A (es) * | 2010-08-13 | 2011-12-01 | Biolab Sanus Farmaceutuca Limitada | Derivados de 6,7-dihidro-3h-oxazolo[3,4]pirazin-5,8-diona |
-
2011
- 2011-07-27 UY UY0001033535A patent/UY33535A/es active IP Right Grant
- 2011-08-02 MX MX2013001692A patent/MX347632B/es active IP Right Grant
- 2011-08-02 CN CN201180039626.8A patent/CN103108878B/zh active Active
- 2011-08-02 JP JP2013523443A patent/JP5940535B2/ja active Active
- 2011-08-02 CA CA2807872A patent/CA2807872C/en active Active
- 2011-08-02 HU HUE11815927A patent/HUE027903T2/hu unknown
- 2011-08-02 KR KR1020137006343A patent/KR101871856B1/ko active Active
- 2011-08-02 US US13/196,363 patent/US8338432B2/en active Active
- 2011-08-02 BR BR112013003225-1A patent/BR112013003225B1/pt active IP Right Grant
- 2011-08-02 DK DK11815927.6T patent/DK2603512T3/en active
- 2011-08-02 ES ES11815927.6T patent/ES2565493T3/es active Active
- 2011-08-02 EP EP11815927.6A patent/EP2603512B1/en active Active
- 2011-08-02 PL PL11815927.6T patent/PL2603512T3/pl unknown
- 2011-08-02 WO PCT/BR2011/000255 patent/WO2012019254A1/en not_active Ceased
- 2011-08-02 RU RU2013110795/04A patent/RU2581831C2/ru active
- 2011-08-09 AR ARP110102892A patent/AR082661A1/es active IP Right Grant
-
2013
- 2013-02-12 IL IL224683A patent/IL224683A/en active IP Right Grant
- 2013-02-12 CL CL2013000434A patent/CL2013000434A1/es unknown
- 2013-03-08 CO CO13046988A patent/CO6680703A2/es active IP Right Grant
- 2013-03-12 EC ECSP13012486 patent/ECSP13012486A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2013110795A (ru) | 2014-09-20 |
| EP2603512A4 (en) | 2014-07-16 |
| CL2013000434A1 (es) | 2013-06-07 |
| RU2581831C2 (ru) | 2016-04-20 |
| CA2807872C (en) | 2018-07-24 |
| WO2012019254A1 (en) | 2012-02-16 |
| KR101871856B1 (ko) | 2018-06-28 |
| MX2013001692A (es) | 2013-03-18 |
| DK2603512T3 (en) | 2016-04-04 |
| BR112013003225A2 (pt) | 2016-06-07 |
| EP2603512A1 (en) | 2013-06-19 |
| ECSP13012486A (es) | 2013-04-30 |
| BR112013003225B1 (pt) | 2021-03-30 |
| PL2603512T3 (pl) | 2016-09-30 |
| HUE027903T2 (hu) | 2016-11-28 |
| KR20130109110A (ko) | 2013-10-07 |
| US8338432B2 (en) | 2012-12-25 |
| UY33535A (es) | 2011-12-01 |
| HK1184786A1 (zh) | 2014-01-30 |
| CN103108878A (zh) | 2013-05-15 |
| ES2565493T3 (es) | 2016-04-05 |
| CO6680703A2 (es) | 2013-05-31 |
| MX347632B (es) | 2017-05-04 |
| US20120040988A1 (en) | 2012-02-16 |
| CN103108878B (zh) | 2016-01-27 |
| JP5940535B2 (ja) | 2016-06-29 |
| JP2013533290A (ja) | 2013-08-22 |
| EP2603512B1 (en) | 2015-12-30 |
| IL224683A (en) | 2016-03-31 |
| CA2807872A1 (en) | 2012-02-16 |
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