HRP20191744T1 - 1-[2-(aminometil)benzil]-2-tiokso-1,2,3,5-tetrahidro-4h-pirolo[3,2-d]pirimidin-4-oni kao inhibitori mijeloperoksidaze - Google Patents
1-[2-(aminometil)benzil]-2-tiokso-1,2,3,5-tetrahidro-4h-pirolo[3,2-d]pirimidin-4-oni kao inhibitori mijeloperoksidaze Download PDFInfo
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- HRP20191744T1 HRP20191744T1 HRP20191744TT HRP20191744T HRP20191744T1 HR P20191744 T1 HRP20191744 T1 HR P20191744T1 HR P20191744T T HRP20191744T T HR P20191744TT HR P20191744 T HRP20191744 T HR P20191744T HR P20191744 T1 HRP20191744 T1 HR P20191744T1
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- Prior art keywords
- thioxo
- pyrrolo
- pyrimidin
- tetrahydro
- compound according
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- CPBCADIXBKGTOI-UHFFFAOYSA-N 1-[[2-(aminomethyl)phenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical class NCC1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC=C1 CPBCADIXBKGTOI-UHFFFAOYSA-N 0.000 title 1
- 102000003896 Myeloperoxidases Human genes 0.000 title 1
- 108090000235 Myeloperoxidases Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- MFCVOLWLNXXQFY-UHFFFAOYSA-N 1-[[2-(aminomethyl)-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound NCC1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl MFCVOLWLNXXQFY-UHFFFAOYSA-N 0.000 claims 2
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 claims 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 2
- BHKKSKOHRFHHIN-UHFFFAOYSA-N 1-[[2-(1-aminoethyl)-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound NC(C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-UHFFFAOYSA-N 0.000 claims 1
- KOPUWFPQOGVDBZ-UHFFFAOYSA-N 1-[[2-(aminomethyl)-4-(trifluoromethyl)phenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound NCC1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)C(F)(F)F KOPUWFPQOGVDBZ-UHFFFAOYSA-N 0.000 claims 1
- YKCTXOZWOMACTO-UHFFFAOYSA-N 1-[[2-(methylaminomethyl)-4-(trifluoromethyl)phenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound CNCC1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)C(F)(F)F YKCTXOZWOMACTO-UHFFFAOYSA-N 0.000 claims 1
- TZUWRLCRGQTVLE-GFCCVEGCSA-N 1-[[2-[(1R)-1-aminopropyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](CC)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl TZUWRLCRGQTVLE-GFCCVEGCSA-N 0.000 claims 1
- BHKKSKOHRFHHIN-QMMMGPOBSA-N 1-[[2-[(1S)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-QMMMGPOBSA-N 0.000 claims 1
- GAYJRJUSCBZATB-UHFFFAOYSA-N 1-[[2-[(2-methylpropylamino)methyl]phenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound CC(CNCC1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC=C1)C GAYJRJUSCBZATB-UHFFFAOYSA-N 0.000 claims 1
- PVUWJFQCPJQRNY-UHFFFAOYSA-N 1-[[2-[(cyclobutylmethylamino)methyl]phenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound C1(CCC1)CNCC1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC=C1 PVUWJFQCPJQRNY-UHFFFAOYSA-N 0.000 claims 1
- JZRGPABFYJPXQJ-UHFFFAOYSA-N 1-[[4-chloro-2-(ethylaminomethyl)phenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound ClC1=CC(=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=C1)CNCC JZRGPABFYJPXQJ-UHFFFAOYSA-N 0.000 claims 1
- QNKLBACGOUFKKR-UHFFFAOYSA-N 1-[[4-chloro-2-(methylaminomethyl)phenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound ClC1=CC(=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=C1)CNC QNKLBACGOUFKKR-UHFFFAOYSA-N 0.000 claims 1
- KMQDMKOHXUMLRM-UHFFFAOYSA-N 1-[[4-chloro-2-[1-(methylamino)ethyl]phenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound ClC1=CC(=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=C1)C(C)NC KMQDMKOHXUMLRM-UHFFFAOYSA-N 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 208000038003 heart failure with preserved ejection fraction Diseases 0.000 claims 1
- 208000038002 heart failure with reduced ejection fraction Diseases 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- -1 propan-2-ylamino Chemical group 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 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
- A61K31/495—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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (16)
1. Spoj s formulom (I)
naznačen time što
R1 je H, F, Cl ili CF3;
R2 je H, CH3 ili C2H5; i
R3 je H, CH3, C2H5, n-propil, izopropil, n-butil, izobutil, sec-butil, tert-butil, ciklopropil, ciklopropilmetil, ciklobutil, ciklobutilmetil ili ciklopentil;
ili njegova farmaceutski prihvatljiva sol.
2. Spoj prema patentnom zahtjevu 1 naznačen time što R1 je Cl.
3. Spoj prema patentnom zahtjevu 1 naznačen time što R2 je CH3.
4. Spoj prema patentnom zahtjevu 1 naznačen time što R2 je H.
5. Spoj prema patentnom zahtjevu 1 naznačen time što R3 je H.
6. Spoj prema patentnom zahtjevu 1 naznačen time što ugljikov atom na koji je R2 vezan ima R-konfiguraciju kada R2 je CH3 ili C2H5.
7. Spoj prema patentnom zahtjevu 1, naznačen time što je 1-{2-[(1R)-1-aminoetil]-4-klorobenzil}-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on:
ili njegova farmaceutski prihvatljiva sol.
8. Spoj prema patentnom zahtjevu 1, naznačen time što je 1-{2-[(1R)-1-aminoetil]-4-klorobenzil}-2-tiokso-1,2,3 ,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on:
9. Spoj prema patentnom zahtjevu 1, naznačen time što je 1-[2-(aminometil)-4-klorobenzil]-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on:
ili njegova farmaceutski prihvatljiva sol.
10. Spoj prema patentnom zahtjevu 1, naznačen time što je 1-[2-(aminometil)-4-klorobenzil]-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on:
11. Spoj prema patentnom zahtjevu 1 naznačen time što je odabran iz niza koji čine
1-{2-[(1R)-1-aminopropil]-4-klorobenzil}-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on;
1-[2-(1-aminoetil)-4-klorobenzil]-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on;
1-{2-[(1S)-1-aminoetil]-4-klorobenzil}-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on;
1-{4-kloro-2-[1 -(metilamino)etil]benzil}-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on;
1-{4-kloro-2-[(etilamino)metil]benzil}-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on;
1-{4-kloro-2-[(metilamino)metil]benzil}-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on;
1-(2-{[(ciklobutilmetil)amino]metil}benzil)-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on;
1-(2-[(ciklobutilamino)metil]benzil[-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on;
1-{2-[(ciklopentilamino)metil]benzil[-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on;
1-(2-{[(2-metilpropil)amino]metil}benzil)-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on;
1-(2-[(propan-2-ilamino)metil]benzil[-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on;
1-[2-(aminometil)-4-(trifluorometil)benzil]-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on;
1-{2-[(metilamino)metil]-4-(trifluorometil)benzil}-2-tiokso-1,2,3,5-tetrahidro-4H-pirolo[3,2-d]pirimidin-4-on;
ili njihova farmaceutski prihvatljiva sol.
12. Farmaceutski pripravak naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 11, ili njegovu farmaceutski prihvatljivu sol, proizvoljno u smjesi s farmaceutski prihvatljivim pomoćnom tvari, razrjeđivačima ili nosačem.
13. Spoj prema bilo kojem od patentnih zahtjeva 1 do 11, ili njegova farmaceutski prihvatljiva sol, naznačen time što je za uporabu kao lijek.
14. Spoj prema bilo kojem od patentnih zahtjeva 1 do 11 naznačen time što je za uporabu za liječenje zatajenja srca.
15. Spoj prema bilo kojem od patentnih zahtjeva 1 do 11 naznačen time što je za uporabu za liječenje zatajenja srca sa smanjenom ejekcijskom frakcijom.
16. Spoj prema bilo kojem od patentnih zahtjeva 1 do 11 naznačen time što je za uporabu za liječenje zatajenja srca sa sačuvanom ejekcijskom frakcijom.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462085722P | 2014-12-01 | 2014-12-01 | |
| US201562166808P | 2015-05-27 | 2015-05-27 | |
| PCT/EP2015/077998 WO2016087338A1 (en) | 2014-12-01 | 2015-11-30 | 1-[2-(aminomethyl)benzyl]-2-thioxo-1,2,3,5-tetrahydro-4h-pyrrolo[3,2-d]pyrimidin-4-ones as inhibitors of myeloperoxidase |
| EP15802075.0A EP3227294B1 (en) | 2014-12-01 | 2015-11-30 | 1-[2-(aminomethyl)benzyl]-2-thioxo-1,2,3,5-tetrahydro-4h-pyrrolo[3,2-d]pyrimidin-4-ones as inhibitors of myeloperoxidase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20191744T1 true HRP20191744T1 (hr) | 2019-12-27 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20191744TT HRP20191744T1 (hr) | 2014-12-01 | 2019-09-26 | 1-[2-(aminometil)benzil]-2-tiokso-1,2,3,5-tetrahidro-4h-pirolo[3,2-d]pirimidin-4-oni kao inhibitori mijeloperoksidaze |
Country Status (38)
| Country | Link |
|---|---|
| US (4) | US9616063B2 (hr) |
| EP (1) | EP3227294B1 (hr) |
| JP (1) | JP6616417B2 (hr) |
| KR (1) | KR102543404B1 (hr) |
| CN (1) | CN107001374B (hr) |
| AU (1) | AU2015357290B2 (hr) |
| BR (1) | BR112017011124B1 (hr) |
| CA (1) | CA2968449C (hr) |
| CL (1) | CL2017001380A1 (hr) |
| CO (1) | CO2017006658A2 (hr) |
| CY (1) | CY1122587T1 (hr) |
| DK (1) | DK3227294T3 (hr) |
| DO (1) | DOP2017000129A (hr) |
| EA (1) | EA030805B1 (hr) |
| ES (1) | ES2751690T3 (hr) |
| GT (1) | GT201700114A (hr) |
| HK (1) | HK1245270A1 (hr) |
| HR (1) | HRP20191744T1 (hr) |
| HU (1) | HUE045606T2 (hr) |
| IL (1) | IL252436B (hr) |
| LT (1) | LT3227294T (hr) |
| ME (1) | ME03568B (hr) |
| MX (1) | MX370492B (hr) |
| MY (1) | MY195816A (hr) |
| NI (1) | NI201700065A (hr) |
| NZ (1) | NZ732164A (hr) |
| PE (1) | PE20170914A1 (hr) |
| PH (1) | PH12017500977A1 (hr) |
| PL (1) | PL3227294T3 (hr) |
| PT (1) | PT3227294T (hr) |
| RS (1) | RS59375B1 (hr) |
| SG (1) | SG11201703961UA (hr) |
| SI (1) | SI3227294T1 (hr) |
| SV (1) | SV2017005451A (hr) |
| TN (1) | TN2017000208A1 (hr) |
| TW (1) | TWI681963B (hr) |
| UY (1) | UY36416A (hr) |
| WO (1) | WO2016087338A1 (hr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9616063B2 (en) * | 2014-12-01 | 2017-04-11 | Astrazeneca Ab | 1-[2-(aminomethyl)benzyl]-2-thioxo-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-d]pyrimidin-4-ones as inhibitors of myeloperoxidase |
| US11246870B2 (en) * | 2017-07-17 | 2022-02-15 | Astrazenca Ab | MPO inhibitors for use in medicine |
| CN112151111B (zh) * | 2020-08-27 | 2022-10-11 | 上海大学 | 基于多元线性回归快速预测黄嘌呤衍生物抑制活性的qsar方法 |
| CN115403584B (zh) * | 2021-05-26 | 2024-04-02 | 长春金赛药业有限责任公司 | 2-硫代-2,3-二氢嘧啶-4-酮衍生物、药物组合物及其制备方法和应用 |
| US20240166642A1 (en) | 2022-08-18 | 2024-05-23 | Astrazeneca Ab | Inhibitors of myeloperoxidase |
| US20240092787A1 (en) | 2022-08-24 | 2024-03-21 | Astrazeneca Ab | Pharmaceutical process and intermediates |
| US20240091231A1 (en) | 2022-08-31 | 2024-03-21 | Astrazeneca Ab | Pharmaceutical formulations |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR039385A1 (es) | 2002-04-19 | 2005-02-16 | Astrazeneca Ab | Derivados de tioxantina como inhibidores de la mieloperoxidasa |
| US20050130983A1 (en) * | 2002-05-02 | 2005-06-16 | Dae-Kee Kim | Pyrrolopyrimidinone derivatives, process for preparation thereof, and method of using and composition comprising them |
| SE0302756D0 (sv) | 2003-10-17 | 2003-10-17 | Astrazeneca Ab | Novel Compounds |
| GB0401269D0 (en) * | 2004-01-21 | 2004-02-25 | Astrazeneca Ab | Compounds |
| MY140748A (en) * | 2004-12-06 | 2010-01-15 | Astrazeneca Ab | Novel pyrrolo [3,2-d] pyrimidin-4-one derivatives and their use in therapy |
| CN101124228B (zh) * | 2004-12-14 | 2011-06-15 | 阿斯利康(瑞典)有限公司 | 用作抗肿瘤药物的吡唑并嘧啶化合物 |
| UY30267A1 (es) | 2006-04-13 | 2007-11-30 | Astrazeneca Ab | Nuevos derivados de la tioxantina , composiciones farmacéuticas que los contienen, procedimientos de preparacion y aplicaciones |
| WO2007120097A1 (en) | 2006-04-13 | 2007-10-25 | Astrazeneca Ab | Thioxanthine derivatives and their use as inhibitors of mpo |
| CN101460501A (zh) | 2006-06-05 | 2009-06-17 | 阿斯利康(瑞典)有限公司 | 作为髓过氧化物酶抑制剂的吡咯并[3，2-d]嘧啶-4-酮衍生物 |
| TW200804383A (en) | 2006-06-05 | 2008-01-16 | Astrazeneca Ab | New compounds |
| US20090054468A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Use 938 |
| USRE47009E1 (en) | 2011-02-01 | 2018-08-28 | The Children's Hospital Of Philadelphia | HDAC inhibitors and therapeutic methods using the same |
| WO2013068875A1 (en) | 2011-11-11 | 2013-05-16 | Pfizer Inc. | 2-thiopyrimidinones |
| US9616063B2 (en) * | 2014-12-01 | 2017-04-11 | Astrazeneca Ab | 1-[2-(aminomethyl)benzyl]-2-thioxo-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-d]pyrimidin-4-ones as inhibitors of myeloperoxidase |
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