BR112015003232B1 - composto de pirimidina substituído por grupo bicíclico, seu uso como inibidor de pde-5, bem como formulação farmacêutica compreendendo o dito composto - Google Patents
composto de pirimidina substituído por grupo bicíclico, seu uso como inibidor de pde-5, bem como formulação farmacêutica compreendendo o dito composto Download PDFInfo
- Publication number
- BR112015003232B1 BR112015003232B1 BR112015003232A BR112015003232A BR112015003232B1 BR 112015003232 B1 BR112015003232 B1 BR 112015003232B1 BR 112015003232 A BR112015003232 A BR 112015003232A BR 112015003232 A BR112015003232 A BR 112015003232A BR 112015003232 B1 BR112015003232 B1 BR 112015003232B1
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- Brazil
- Prior art keywords
- amino
- compound
- chloro
- methoxy
- substituent
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Links
- 0 C*c(ccc(CNc(nc(N1C(C*)C(C2)C2C1)nc1)c1C(NC1CCCCC1)=O)c1)c1Cl Chemical compound C*c(ccc(CNc(nc(N1C(C*)C(C2)C2C1)nc1)c1C(NC1CCCCC1)=O)c1)c1Cl 0.000 description 41
- ZWYNHXMZWYVAJS-UHFFFAOYSA-N C1C2=CNCC12 Chemical compound C1C2=CNCC12 ZWYNHXMZWYVAJS-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N CC(CC1)CCC1O Chemical compound CC(CC1)CCC1O MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- RKHIMLYCTQVKGQ-UHFFFAOYSA-N CC(Cc(cc1N)ccc1O)=C Chemical compound CC(Cc(cc1N)ccc1O)=C RKHIMLYCTQVKGQ-UHFFFAOYSA-N 0.000 description 1
- YLULMQLBEAXJFL-UHFFFAOYSA-N CCOC(c(cn1)c(NCc(cc2)cc(C)c2O)nc1SC)=O Chemical compound CCOC(c(cn1)c(NCc(cc2)cc(C)c2O)nc1SC)=O YLULMQLBEAXJFL-UHFFFAOYSA-N 0.000 description 1
- SNNHLSHDDGJVDM-UHFFFAOYSA-N CCOC(c(cnc(SC)n1)c1Cl)=O Chemical compound CCOC(c(cnc(SC)n1)c1Cl)=O SNNHLSHDDGJVDM-UHFFFAOYSA-N 0.000 description 1
- QDQMEHXIUFCIGR-UHFFFAOYSA-N CCc(cc1C)ccc1O Chemical compound CCc(cc1C)ccc1O QDQMEHXIUFCIGR-UHFFFAOYSA-N 0.000 description 1
- BACLRPFZQCWHJH-UHFFFAOYSA-N COc(ccc(CNc(nc(N1CC2(CC2)CC1)nc1)c1C(NCc1ncccn1)=O)c1)c1Cl Chemical compound COc(ccc(CNc(nc(N1CC2(CC2)CC1)nc1)c1C(NCc1ncccn1)=O)c1)c1Cl BACLRPFZQCWHJH-UHFFFAOYSA-N 0.000 description 1
- UKRWMOAZEZXCCW-UHFFFAOYSA-N COc(ccc(CNc(nc(nc1)S(C)=O)c1C(NCc1ccccc1)=O)c1)c1Cl Chemical compound COc(ccc(CNc(nc(nc1)S(C)=O)c1C(NCc1ccccc1)=O)c1)c1Cl UKRWMOAZEZXCCW-UHFFFAOYSA-N 0.000 description 1
- NKAVILAJSNUOES-VNGAXPGBSA-N COc(ccc(CNc1nc(N2CC(C3)C3C2)ncc1C(N[C@H](CC1)CC[C@@H]1O)=O)c1)c1Cl Chemical compound COc(ccc(CNc1nc(N2CC(C3)C3C2)ncc1C(N[C@H](CC1)CC[C@@H]1O)=O)c1)c1Cl NKAVILAJSNUOES-VNGAXPGBSA-N 0.000 description 1
- RFJPUCRDADKNGX-ZDUSSCGKSA-N C[C@@H](C=C1C(O)=O)[I]=C(N2CC3(CC3)CC2)N=C1NCc(cc1)cc(Cl)c1OC Chemical compound C[C@@H](C=C1C(O)=O)[I]=C(N2CC3(CC3)CC2)N=C1NCc(cc1)cc(Cl)c1OC RFJPUCRDADKNGX-ZDUSSCGKSA-N 0.000 description 1
- XIBPEVWGRFTYJA-UHFFFAOYSA-N Cc(cc(CNc(nc(C)nc1)c1C(NCc1ccccc1)=O)cc1)c1OC Chemical compound Cc(cc(CNc(nc(C)nc1)c1C(NCc1ccccc1)=O)cc1)c1OC XIBPEVWGRFTYJA-UHFFFAOYSA-N 0.000 description 1
- MQJPVOVUEKWANU-UHFFFAOYSA-N Cc(nc(N1CC2(CC2)CC1)nc1)c1C(O)=O Chemical compound Cc(nc(N1CC2(CC2)CC1)nc1)c1C(O)=O MQJPVOVUEKWANU-UHFFFAOYSA-N 0.000 description 1
- MSARRSNHWLPURH-UHFFFAOYSA-N Cc1cc(CCc2nc(N3CC4(CC4)CC3)ncc2C(O)=O)ccc1OC Chemical compound Cc1cc(CCc2nc(N3CC4(CC4)CC3)ncc2C(O)=O)ccc1OC MSARRSNHWLPURH-UHFFFAOYSA-N 0.000 description 1
- PWCYCEMYVBORME-UHFFFAOYSA-N NC(N1C2(CC2)CCC1)=N Chemical compound NC(N1C2(CC2)CCC1)=N PWCYCEMYVBORME-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
-
- 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
- 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
- A61P13/08—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
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems
-
- 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
- C07D471/10—Spiro-condensed systems
-
- 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
- C07D487/08—Bridged systems
-
- 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
- C07D487/10—Spiro-condensed systems
-
- 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
- C07D498/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Vascular Medicine (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210289185 | 2012-08-14 | ||
| PCT/CN2013/000953 WO2014026467A1 (zh) | 2012-08-14 | 2013-08-14 | 双环取代的嘧啶类化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112015003232A2 BR112015003232A2 (pt) | 2017-10-24 |
| BR112015003232B1 true BR112015003232B1 (pt) | 2020-04-07 |
Family
ID=50101233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112015003232A BR112015003232B1 (pt) | 2012-08-14 | 2013-08-14 | composto de pirimidina substituído por grupo bicíclico, seu uso como inibidor de pde-5, bem como formulação farmacêutica compreendendo o dito composto |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9359371B2 (https=) |
| EP (1) | EP2886540B1 (https=) |
| JP (1) | JP6037489B2 (https=) |
| KR (1) | KR101794321B1 (https=) |
| CN (1) | CN104487434B (https=) |
| BR (1) | BR112015003232B1 (https=) |
| ES (1) | ES2641992T3 (https=) |
| WO (1) | WO2014026467A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101749314B1 (ko) | 2013-03-29 | 2017-07-03 | 수안주 파마 코포레이션 리미티드 | 비사이클릭-치환된 피리미딘 타입 pde-5 억제제의 프로드러그 |
| CN111406053B (zh) * | 2017-12-11 | 2023-03-31 | 轩竹生物科技股份有限公司 | 磷酸二酯酶-5抑制剂的晶型 |
| CN109438421A (zh) * | 2018-11-13 | 2019-03-08 | 扬州市三药制药有限公司 | 一种阿伐那非中间体的精制纯化方法 |
| WO2020177129A1 (zh) * | 2019-03-07 | 2020-09-10 | 华东理工大学 | 2,7-二氮杂-螺[4.4]壬烷类异羟肟酸嘧啶类化合物及其制备和应用 |
| WO2020177128A1 (zh) * | 2019-03-07 | 2020-09-10 | 华东理工大学 | 2,6-二氮杂螺[3.4]辛烷类嘧啶-异羟肟酸化合物及其用途 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1219609B1 (en) | 1999-09-16 | 2007-04-04 | Tanabe Seiyaku Co., Ltd. | Aromatic nitrogenous six-membered ring compounds |
| JP3637961B2 (ja) * | 1999-09-16 | 2005-04-13 | 田辺製薬株式会社 | 芳香族含窒素六員環化合物 |
| US7087597B1 (en) * | 1999-10-12 | 2006-08-08 | Takeda Pharmaceutical Company Limited | Pyrimidine 5-carboxamide compounds, process for producing the same and use thereof |
| JP2001233875A (ja) * | 1999-10-12 | 2001-08-28 | Takeda Chem Ind Ltd | ピリミジン−５−カルボキサミド化合物、その製造法およびその用途 |
| NZ522217A (en) * | 2000-04-28 | 2004-04-30 | Tanabe Seiyaku Co | Cyclic compounds |
| NZ524572A (en) | 2000-09-06 | 2004-08-27 | Tanabe Seiyaku Co | Oral compositions comprising phosphodiesterase inhibitors ( PDE inhibitor )and an acidic substance such as fumaric acid with improved drug efficacy due to decrease solubility in neutral and alkaline regions |
| JP4178816B2 (ja) * | 2001-03-15 | 2008-11-12 | 田辺三菱製薬株式会社 | 医薬組成物 |
| WO2008024974A1 (en) | 2006-08-24 | 2008-02-28 | Serenex, Inc. | Pyrimidine and pyrazine derivatives |
| NZ588830A (en) * | 2008-04-22 | 2012-11-30 | Portola Pharm Inc | Inhibitors of protein kinases |
| CN102372697A (zh) | 2010-08-19 | 2012-03-14 | 山东轩竹医药科技有限公司 | 取代的嘧啶类化合物 |
| US20140107100A1 (en) | 2010-11-24 | 2014-04-17 | Exelixis, Inc. | Benzoxazepines as Inhibitors of PI3K/mTOR and Methods of Their Use and Manufacture |
| JP5697800B2 (ja) | 2011-07-21 | 2015-04-08 | シュエンジュウ・ファーマ・カンパニー・リミテッド | 複素環置換ピリミジン化合物 |
-
2013
- 2013-08-14 CN CN201380039519.4A patent/CN104487434B/zh active Active
- 2013-08-14 KR KR1020157006568A patent/KR101794321B1/ko active Active
- 2013-08-14 BR BR112015003232A patent/BR112015003232B1/pt active IP Right Grant
- 2013-08-14 WO PCT/CN2013/000953 patent/WO2014026467A1/zh not_active Ceased
- 2013-08-14 US US14/421,703 patent/US9359371B2/en active Active
- 2013-08-14 ES ES13829720.5T patent/ES2641992T3/es active Active
- 2013-08-14 EP EP13829720.5A patent/EP2886540B1/en active Active
- 2013-08-14 JP JP2015526856A patent/JP6037489B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015524828A (ja) | 2015-08-27 |
| EP2886540A4 (en) | 2015-06-24 |
| US20150232474A1 (en) | 2015-08-20 |
| EP2886540A1 (en) | 2015-06-24 |
| KR20150042846A (ko) | 2015-04-21 |
| ES2641992T3 (es) | 2017-11-14 |
| BR112015003232A2 (pt) | 2017-10-24 |
| EP2886540B1 (en) | 2017-07-26 |
| HK1205738A1 (en) | 2015-12-24 |
| CN104487434A (zh) | 2015-04-01 |
| CN104487434B (zh) | 2018-05-22 |
| KR101794321B1 (ko) | 2017-12-01 |
| US9359371B2 (en) | 2016-06-07 |
| WO2014026467A1 (zh) | 2014-02-20 |
| JP6037489B2 (ja) | 2016-12-07 |
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