TW472059B - Thienopyrimidines, preparation process thereof, and pharmaceutical composition containing the same - Google Patents
Thienopyrimidines, preparation process thereof, and pharmaceutical composition containing the same Download PDFInfo
- Publication number
- TW472059B TW472059B TW087119650A TW87119650A TW472059B TW 472059 B TW472059 B TW 472059B TW 087119650 A TW087119650 A TW 087119650A TW 87119650 A TW87119650 A TW 87119650A TW 472059 B TW472059 B TW 472059B
- Authority
- TW
- Taiwan
- Prior art keywords
- pyrimidin
- acid
- benzothieno
- formula
- tetrahydro
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 title claims 3
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 101
- -1 7- [ 4- (3-chloro-4-methoxyfluorenylamino) -5,6,7,8-tetrahydro [1] benzothieno [2, 3-d] pyrimidin-2-yl] heptanoic acid Chemical compound 0.000 claims description 87
- 150000001875 compounds Chemical class 0.000 claims description 74
- 238000006243 chemical reaction Methods 0.000 claims description 66
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 58
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 47
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 26
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 235000019260 propionic acid Nutrition 0.000 claims description 20
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 5
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 230000002792 vascular Effects 0.000 claims description 3
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 2
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 208000035475 disorder Diseases 0.000 abstract description 4
- 230000005764 inhibitory process Effects 0.000 abstract description 3
- 102000011016 Type 5 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 abstract 1
- 108010037581 Type 5 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 abstract 1
- 210000000748 cardiovascular system Anatomy 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 27
- 150000002169 ethanolamines Chemical class 0.000 description 19
- 230000008018 melting Effects 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 150000003254 radicals Chemical class 0.000 description 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 16
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- 229940070710 valerate Drugs 0.000 description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 7
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- XNCNNDVCAUWAIT-UHFFFAOYSA-N Methyl heptanoate Chemical compound CCCCCCC(=O)OC XNCNNDVCAUWAIT-UHFFFAOYSA-N 0.000 description 6
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- 125000005605 benzo group Chemical group 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- 238000007670 refining Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 125000003277 amino group Chemical group 0.000 description 3
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 3
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
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- 229940017219 methyl propionate Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- UZLITANBGSATPT-UHFFFAOYSA-N 2-(9h-fluoren-1-yloxy)ethanol Chemical compound C1C2=CC=CC=C2C2=C1C(OCCO)=CC=C2 UZLITANBGSATPT-UHFFFAOYSA-N 0.000 description 2
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 2
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- DOTPSQVYOBAWPQ-UHFFFAOYSA-N pyrazolo[4,3-d]pyrimidin-3-one Chemical class N1=CN=C2C(=O)N=NC2=C1 DOTPSQVYOBAWPQ-UHFFFAOYSA-N 0.000 description 1
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- DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Hospice & Palliative Care (AREA)
- Gynecology & Obstetrics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752952A DE19752952A1 (de) | 1997-11-28 | 1997-11-28 | Thienopyrimidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW472059B true TW472059B (en) | 2002-01-11 |
Family
ID=7850200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW087119650A TW472059B (en) | 1997-11-28 | 1998-11-26 | Thienopyrimidines, preparation process thereof, and pharmaceutical composition containing the same |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US6420368B1 (enExample) |
| EP (1) | EP1036078B1 (enExample) |
| JP (1) | JP4314341B2 (enExample) |
| KR (1) | KR20010032445A (enExample) |
| CN (1) | CN1138780C (enExample) |
| AR (1) | AR010962A1 (enExample) |
| AT (1) | ATE361926T1 (enExample) |
| AU (1) | AU742433B2 (enExample) |
| BR (1) | BR9815409A (enExample) |
| CA (1) | CA2311922C (enExample) |
| CO (1) | CO4980884A1 (enExample) |
| CZ (1) | CZ291068B6 (enExample) |
| DE (2) | DE19752952A1 (enExample) |
| ES (1) | ES2285796T3 (enExample) |
| HK (1) | HK1038924A1 (enExample) |
| HU (1) | HUP0100488A3 (enExample) |
| ID (1) | ID24571A (enExample) |
| NO (1) | NO20002702D0 (enExample) |
| PL (1) | PL341156A1 (enExample) |
| RU (1) | RU2217431C2 (enExample) |
| SK (1) | SK7772000A3 (enExample) |
| TW (1) | TW472059B (enExample) |
| WO (1) | WO1999028325A1 (enExample) |
| ZA (1) | ZA9810845B (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19819023A1 (de) | 1998-04-29 | 1999-11-04 | Merck Patent Gmbh | Thienopyrimidine |
| CA2365578A1 (en) | 1999-03-30 | 2000-10-12 | Seiichi Uchida | Thienopyrimidine compounds and salts thereof and process for the preparation of the same |
| DE19942474A1 (de) * | 1999-09-06 | 2001-03-15 | Merck Patent Gmbh | Pyrazolo[4,3-d]pyrimidine |
| CN1436080A (zh) | 2000-04-19 | 2003-08-13 | 利利艾科斯有限公司 | 环gmp－特异性磷酸二酯酶抑制剂治疗帕金森氏病的用途 |
| DE10031584A1 (de) | 2000-06-29 | 2002-01-10 | Merck Patent Gmbh | 5-Aminoalkyl-pyrazolo[4,3-d]pyrimidine |
| DE10031585A1 (de) * | 2000-06-29 | 2002-01-10 | Merck Patent Gmbh | 2-Aminoalkyl-thieno[2,3-d]pyrimidine |
| DE10042997A1 (de) * | 2000-09-01 | 2002-03-14 | Merck Patent Gmbh | Thienopyrimidine |
| CA2423981A1 (en) * | 2000-09-29 | 2003-03-28 | Kimiko Ichikawa | Thienopyrimidine compounds and salts thereof and process for the preparation of the same |
| DE10058663A1 (de) * | 2000-11-25 | 2002-05-29 | Merck Patent Gmbh | Verwendung von Thienopyrimidinen |
| AU2002227957A1 (en) * | 2000-12-19 | 2002-07-01 | Merck Patent Gmbh | Pharmaceutical formulation containing thienopyrimidines and antithrombotics, calcium antagonists, prostaglandins or prostaglandin derivatives |
| DE10064994A1 (de) * | 2000-12-23 | 2002-07-04 | Merck Patent Gmbh | Sulfamidothienopyrimidine |
| DE10103647A1 (de) | 2001-01-27 | 2002-08-01 | Merck Patent Gmbh | Verfahren zur Herstellung eines Pyrazolo (4,3-d) pyrimidinderivates |
| WO2002060449A2 (de) * | 2001-01-31 | 2002-08-08 | Merck Patent Gmbh | Pharmazeutische formulierung enthaltend pyrazolo[4,3-d]pyrimidine und nitrate oder thienopyrimidine und nitrate |
| CN101100472A (zh) * | 2001-04-30 | 2008-01-09 | 美国拜尔公司 | 4-氨基-5,6-取代的噻吩并[2,3-d]嘧啶化合物及其应用 |
| DE10148883A1 (de) * | 2001-10-04 | 2003-04-10 | Merck Patent Gmbh | Pyrimidinderivate |
| JPWO2003035653A1 (ja) * | 2001-10-26 | 2005-02-10 | 日本曹達株式会社 | ピリドチエノピリミジン化合物およびその塩 |
| KR100824193B1 (ko) | 2003-04-29 | 2008-04-21 | 화이자 인코포레이티드 | 고혈압 치료에 유용한5,7-디아미노피라졸로[4,3-ｄ]피리미딘 |
| US7572799B2 (en) | 2003-11-24 | 2009-08-11 | Pfizer Inc | Pyrazolo[4,3-d]pyrimidines as Phosphodiesterase Inhibitors |
| JP2007532526A (ja) | 2004-04-07 | 2007-11-15 | ファイザー・インク | ピラゾロ［４，３−ｄ］ピリミジン類 |
| GB0420719D0 (en) * | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| ES2259891B1 (es) * | 2004-11-30 | 2007-11-01 | Laboratorios Almirall S.A. | Nuevos derivados de piridotienopirimidina. |
| ES2259892B1 (es) * | 2004-11-30 | 2007-11-01 | Laboratorios Almirall S.A. | Nuevos derivados de piridotienopirimidina. |
| US9056877B2 (en) | 2011-07-19 | 2015-06-16 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CN109297923A (zh) * | 2018-09-19 | 2019-02-01 | 南通出入境检验检疫局检验检疫综合技术中心 | 纺织品中微量含氟整理剂的测定方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE245666C (enExample) | ||||
| DD245666A1 (de) * | 1985-09-20 | 1987-05-13 | Univ Halle Wittenberg | Verfahren zur herstellung von 4-aminosubstituierten thieno 2,3-d-pyrimidin-2-ylessigsaeureestern |
| GB9301192D0 (en) * | 1993-06-09 | 1993-06-09 | Trott Francis W | Flower shaped mechanised table |
| US5869486A (en) * | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| DE19644228A1 (de) | 1996-10-24 | 1998-04-30 | Merck Patent Gmbh | Thienopyrimidine |
-
1997
- 1997-11-28 DE DE19752952A patent/DE19752952A1/de not_active Withdrawn
-
1998
- 1998-11-19 HK HK02100600.0A patent/HK1038924A1/zh unknown
- 1998-11-19 AT AT98964411T patent/ATE361926T1/de not_active IP Right Cessation
- 1998-11-19 KR KR1020007005686A patent/KR20010032445A/ko not_active Abandoned
- 1998-11-19 CN CNB988113767A patent/CN1138780C/zh not_active Expired - Fee Related
- 1998-11-19 PL PL98341156A patent/PL341156A1/xx not_active Application Discontinuation
- 1998-11-19 HU HU0100488A patent/HUP0100488A3/hu unknown
- 1998-11-19 BR BR9815409-5A patent/BR9815409A/pt not_active Application Discontinuation
- 1998-11-19 WO PCT/EP1998/007436 patent/WO1999028325A1/de not_active Ceased
- 1998-11-19 ES ES98964411T patent/ES2285796T3/es not_active Expired - Lifetime
- 1998-11-19 US US09/555,210 patent/US6420368B1/en not_active Expired - Fee Related
- 1998-11-19 EP EP98964411A patent/EP1036078B1/de not_active Expired - Lifetime
- 1998-11-19 CZ CZ20001962A patent/CZ291068B6/cs not_active IP Right Cessation
- 1998-11-19 ID IDW20000942A patent/ID24571A/id unknown
- 1998-11-19 JP JP2000523217A patent/JP4314341B2/ja not_active Expired - Fee Related
- 1998-11-19 AU AU19625/99A patent/AU742433B2/en not_active Ceased
- 1998-11-19 SK SK777-2000A patent/SK7772000A3/sk unknown
- 1998-11-19 RU RU2000116899/04A patent/RU2217431C2/ru not_active IP Right Cessation
- 1998-11-19 DE DE59814003T patent/DE59814003D1/de not_active Expired - Lifetime
- 1998-11-19 CA CA002311922A patent/CA2311922C/en not_active Expired - Fee Related
- 1998-11-26 TW TW087119650A patent/TW472059B/zh not_active IP Right Cessation
- 1998-11-26 ZA ZA9810845A patent/ZA9810845B/xx unknown
- 1998-11-27 CO CO98070308A patent/CO4980884A1/es unknown
- 1998-11-27 AR ARP980106028A patent/AR010962A1/es not_active Application Discontinuation
-
2000
- 2000-05-26 NO NO20002702A patent/NO20002702D0/no not_active Application Discontinuation
-
2002
- 2002-05-16 US US10/146,028 patent/US6495554B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2311922C (en) | 2009-09-29 |
| JP4314341B2 (ja) | 2009-08-12 |
| CZ20001962A3 (cs) | 2002-01-16 |
| HUP0100488A3 (en) | 2003-03-28 |
| EP1036078A1 (de) | 2000-09-20 |
| AU742433B2 (en) | 2002-01-03 |
| DE59814003D1 (en) | 2007-06-21 |
| PL341156A1 (en) | 2001-03-26 |
| CA2311922A1 (en) | 1999-06-10 |
| CZ291068B6 (cs) | 2002-12-11 |
| EP1036078B1 (de) | 2007-05-09 |
| CO4980884A1 (es) | 2000-11-27 |
| SK7772000A3 (en) | 2000-12-11 |
| US6495554B2 (en) | 2002-12-17 |
| DE19752952A1 (de) | 1999-06-02 |
| AU1962599A (en) | 1999-06-16 |
| RU2217431C2 (ru) | 2003-11-27 |
| NO20002702L (no) | 2000-05-26 |
| ES2285796T3 (es) | 2007-11-16 |
| HUP0100488A2 (hu) | 2001-09-28 |
| US6420368B1 (en) | 2002-07-16 |
| HK1038924A1 (zh) | 2002-04-04 |
| WO1999028325A1 (de) | 1999-06-10 |
| BR9815409A (pt) | 2000-10-24 |
| JP2001525325A (ja) | 2001-12-11 |
| ZA9810845B (en) | 1999-05-26 |
| KR20010032445A (ko) | 2001-04-25 |
| US20020132818A1 (en) | 2002-09-19 |
| CN1306534A (zh) | 2001-08-01 |
| ATE361926T1 (de) | 2007-06-15 |
| ID24571A (id) | 2000-07-27 |
| CN1138780C (zh) | 2004-02-18 |
| NO20002702D0 (no) | 2000-05-26 |
| AR010962A1 (es) | 2000-07-12 |
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