FI112484B - Menetelmä 2-(2-alkoksifenyyli)pyrido[3,2-d]pyrimidin-4(3H)-onijohdannaisten valmistamiseksi - Google Patents
Menetelmä 2-(2-alkoksifenyyli)pyrido[3,2-d]pyrimidin-4(3H)-onijohdannaisten valmistamiseksi Download PDFInfo
- Publication number
- FI112484B FI112484B FI950889A FI950889A FI112484B FI 112484 B FI112484 B FI 112484B FI 950889 A FI950889 A FI 950889A FI 950889 A FI950889 A FI 950889A FI 112484 B FI112484 B FI 112484B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- alkyl
- preparation
- pyrimidin
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 55
- 238000000034 method Methods 0.000 title claims description 36
- 230000008569 process Effects 0.000 title claims description 13
- FSKYZRCACCHDGR-UHFFFAOYSA-N 1h-pyrido[3,2-d]pyrimidin-4-one Chemical class C1=CN=C2C(=O)N=CNC2=C1 FSKYZRCACCHDGR-UHFFFAOYSA-N 0.000 title claims description 8
- -1 1-imidazolidin-2-onyl Chemical group 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 136
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 230000000802 nitrating effect Effects 0.000 claims description 9
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
- 150000001266 acyl halides Chemical class 0.000 claims description 7
- 238000006172 aromatic nitration reaction Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000002828 nitro derivatives Chemical class 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 4
- VVPKDBSEKFTDKW-UHFFFAOYSA-N 3-pyridin-3-ylsulfonylpyridine Chemical group C=1C=CN=CC=1S(=O)(=O)C1=CC=CN=C1 VVPKDBSEKFTDKW-UHFFFAOYSA-N 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- AAVBDGPWCBSBTN-UHFFFAOYSA-N 2-[2-ethoxy-5-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonylphenyl]-8-propyl-1h-pyrido[3,2-d]pyrimidin-4-one Chemical compound CCCC1=CC=NC(C(N=2)=O)=C1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CCO)CC1 AAVBDGPWCBSBTN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 2
- ZJOXWRFJOUWUKX-GOSISDBHSA-N 2-[[4-[(3R)-1-oxo-3,4-dihydroisochromene-3-carbonyl]piperazin-1-yl]methyl]-5,6,7,8-tetrahydro-3H-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound C1CCCC2=C1SC1=C2C(=O)NC(CN2CCN(CC2)C([C@@H]2OC(=O)C3=CC=CC=C3C2)=O)=N1 ZJOXWRFJOUWUKX-GOSISDBHSA-N 0.000 claims 1
- 229940125773 compound 10 Drugs 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000005121 nitriding Methods 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 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 abstract description 13
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Liquid Crystal Substances (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Road Signs Or Road Markings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929218322A GB9218322D0 (en) | 1992-08-28 | 1992-08-28 | Therapeutic agents |
| GB9218322 | 1992-08-28 | ||
| PCT/EP1993/002097 WO1994005661A1 (fr) | 1992-08-28 | 1993-08-04 | Agents antiangineux a la pyridopyrimidinone |
| EP9302097 | 1993-08-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI950889A FI950889A (fi) | 1995-02-27 |
| FI950889A0 FI950889A0 (fi) | 1995-02-27 |
| FI112484B true FI112484B (fi) | 2003-12-15 |
Family
ID=10721102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI950889A FI112484B (fi) | 1992-08-28 | 1995-02-27 | Menetelmä 2-(2-alkoksifenyyli)pyrido[3,2-d]pyrimidin-4(3H)-onijohdannaisten valmistamiseksi |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5591742A (fr) |
| EP (1) | EP0656898B1 (fr) |
| JP (1) | JP2660103B2 (fr) |
| AT (1) | ATE148118T1 (fr) |
| CA (1) | CA2138298C (fr) |
| DE (1) | DE69307712T2 (fr) |
| DK (1) | DK0656898T3 (fr) |
| ES (1) | ES2096936T3 (fr) |
| FI (1) | FI112484B (fr) |
| GB (1) | GB9218322D0 (fr) |
| GR (1) | GR3022852T3 (fr) |
| WO (1) | WO1994005661A1 (fr) |
Families Citing this family (82)
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| US5298518A (en) * | 1989-09-29 | 1994-03-29 | Eisai Co., Ltd. | Biphenylmethane derivative and pharmacological use |
| PT100905A (pt) * | 1991-09-30 | 1994-02-28 | Eisai Co Ltd | Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem |
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| GB9423910D0 (en) | 1994-11-26 | 1995-01-11 | Pfizer Ltd | Therapeutic agents |
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| US6200980B1 (en) | 1995-06-07 | 2001-03-13 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl purinone derivatives |
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| US6060477A (en) * | 1995-06-07 | 2000-05-09 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl cycloamino pyrimidinone derivatives |
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| US5874440A (en) * | 1995-06-07 | 1999-02-23 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl pyrimidinone derivatives |
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| GB9514473D0 (en) * | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
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| UA46166C2 (uk) * | 1997-11-12 | 2002-05-15 | Баєр Акцієнгезельшафт | 2-фенілзаміщені імідазотриазинони як інгібітори фосфодіестерази, спосіб їх одержання та лікарський засіб на їх основі |
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| US5990117A (en) * | 1998-04-15 | 1999-11-23 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to quinazoline derivatives |
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| US6087368A (en) * | 1998-06-08 | 2000-07-11 | Bristol-Myers Squibb Company | Quinazolinone inhibitors of cGMP phosphodiesterase |
| DE19827640A1 (de) * | 1998-06-20 | 1999-12-23 | Bayer Ag | 7-Alkyl- und Cycloalkyl-substituierte Imidazotriazinone |
| US6180629B1 (en) | 1998-08-14 | 2001-01-30 | Cell Pathways, Inc. | [4,5]-Fused-1,3-disubstituted-1,2-diazine-6-one derivatives with nitrogen containing substitutents in position one for the treatment of neoplasia |
| US6268372B1 (en) | 1998-09-11 | 2001-07-31 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 2,9-disubstituted purin-6-ones |
| US6124303A (en) * | 1998-09-11 | 2000-09-26 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 9-substituted 2-(2-N-aloxyphenyl) purin-6-ones |
| US6200771B1 (en) | 1998-10-15 | 2001-03-13 | Cell Pathways, Inc. | Method of using a novel phosphodiesterase in pharmaceutical screeing to identify compounds for treatment of neoplasia |
| GB9823101D0 (en) | 1998-10-23 | 1998-12-16 | Pfizer Ltd | Pharmaceutically active compounds |
| GB9823103D0 (en) | 1998-10-23 | 1998-12-16 | Pfizer Ltd | Pharmaceutically active compounds |
| GB9823102D0 (en) | 1998-10-23 | 1998-12-16 | Pfizer Ltd | Pharmaceutically active compounds |
| US6133271A (en) * | 1998-11-19 | 2000-10-17 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure thienopyrimidine derivatives |
| US6187779B1 (en) | 1998-11-20 | 2001-02-13 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 2,8-disubstituted quinazoline derivatives |
| US6369092B1 (en) | 1998-11-23 | 2002-04-09 | Cell Pathways, Inc. | Method for treating neoplasia by exposure to substituted benzimidazole derivatives |
| US6486155B1 (en) | 1998-11-24 | 2002-11-26 | Cell Pathways Inc | Method of inhibiting neoplastic cells with isoquinoline derivatives |
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| US6225315B1 (en) | 1998-11-30 | 2001-05-01 | Pfizer Inc | Method of treating nitrate-induced tolerance |
| US6025394A (en) | 1999-01-29 | 2000-02-15 | Cell Pathways, Inc. | Method for treating patients with acne by administering substituted sulfonyl indenyl acetic acids, amides and alcohols |
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| US7235625B2 (en) | 1999-06-29 | 2007-06-26 | Palatin Technologies, Inc. | Multiple agent therapy for sexual dysfunction |
| AU7547900A (en) | 1999-10-11 | 2001-04-23 | Pfizer Inc. | 5-(2-substituted-5-heterocyclylsulphonylpyrid-3-yl)- dihydropyrazolo(4,3-d)pyrimidin-7-ones as phosphodiesterase inhibitors |
| TWI265925B (en) | 1999-10-11 | 2006-11-11 | Pfizer | Pyrazolo[4,3-d]pyrimidin-7-ones useful in inhibiting type 5 cyclic guanosine 3',5'-monophosphate phosphodiesterases(cGMP PDE5), process and intermediates for their preparation, their uses and composition comprising them |
| PL356848A1 (en) * | 1999-12-24 | 2004-07-12 | Bayer Aktiengesellschaft | Novel imidazo[1,3,5]triazinones and the use thereof |
| CA2406947A1 (fr) * | 2000-04-19 | 2001-10-25 | Johns Hopkins University | Procedes de prevention et de traitement des troubles gastro-intestinaux |
| WO2001087888A1 (fr) * | 2000-05-17 | 2001-11-22 | Sk Chemicals Co., Ltd. | Derives de pyrazolopyrimidinone, leur procede de preparation et leur utilisation |
| US6548508B2 (en) | 2000-10-20 | 2003-04-15 | Pfizer, Inc. | Use of PDE V inhibitors for improved fecundity in mammals |
| WO2002070483A1 (fr) * | 2001-03-05 | 2002-09-12 | E. I. Du Pont De Nemours And Company | Agents heterocycliques diamide de lutte contre des parasites invertebres |
| US20040102324A1 (en) | 2002-02-28 | 2004-05-27 | Annis Gary David | Heterocyclic diamide invertebrate pest control agents |
| CA2449163C (fr) * | 2001-05-09 | 2010-07-13 | Bayer Healthcare Ag | Utilisation nouvelle d'imidazotriazinones 2-phenyl-substituees |
| ATE455758T1 (de) | 2001-12-20 | 2010-02-15 | Merck Serono Sa | Pyrrolidin-derivatie als prostaglandin- modulatoren |
| GB0202282D0 (en) | 2002-01-31 | 2002-03-20 | Pfizer Ltd | Treatment of male sexual dysfunction |
| US7208516B2 (en) | 2002-03-20 | 2007-04-24 | Celgene Corporation | Methods of the treatment of psoriatic arthritis using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione |
| US6962940B2 (en) | 2002-03-20 | 2005-11-08 | Celgene Corporation | (+)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione: methods of using and compositions thereof |
| US7276529B2 (en) | 2002-03-20 | 2007-10-02 | Celgene Corporation | Methods of the treatment or prevention of exercise-induced asthma using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione |
| US7893101B2 (en) | 2002-03-20 | 2011-02-22 | Celgene Corporation | Solid forms comprising (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione, compositions thereof, and uses thereof |
| KR100490970B1 (ko) * | 2002-03-22 | 2005-05-24 | 씨제이 주식회사 | 신규 피리도[2,3-ｄ]피리미딘 카르보알데히드 옥심계ＰＤＥ Ⅳ 효소 저해 화합물 및 이의 제조방법 |
| DE10232113A1 (de) * | 2002-07-16 | 2004-01-29 | Bayer Ag | Vardenafil Hydrochlorid Trihydrat enthaltende Arzneimittel |
| GB0219961D0 (en) | 2002-08-28 | 2002-10-02 | Pfizer Ltd | Oxytocin inhibitors |
| US7323462B2 (en) | 2002-12-10 | 2008-01-29 | Pfizer Inc. | Morpholine dopamine agonists |
| JP2006511606A (ja) | 2002-12-13 | 2006-04-06 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | 下部尿路症状を治療するα−２−δリガンド |
| AU2004234158B2 (en) | 2003-04-29 | 2010-01-28 | Pfizer Inc. | 5,7-diaminopyrazolo[4,3-D]pyrimidines useful in the treatment of hypertension |
| EP2526958B1 (fr) | 2003-06-13 | 2017-10-18 | Ironwood Pharmaceuticals, Inc. | Procédé et compositions de traitement des troubles gastro-intestinaux |
| US7572799B2 (en) | 2003-11-24 | 2009-08-11 | Pfizer Inc | Pyrazolo[4,3-d]pyrimidines as Phosphodiesterase Inhibitors |
| BRPI0506994A (pt) | 2004-01-22 | 2007-07-03 | Pfizer | derivados de triazol que inibem a atividade antagonista da vasopressina |
| 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 |
| DE102004023069A1 (de) * | 2004-05-11 | 2005-12-08 | Bayer Healthcare Ag | Neue Darreichungsformen des PDE 5-Inhibitors Vardenafil |
| DE102005001989A1 (de) * | 2005-01-15 | 2006-07-20 | Bayer Healthcare Ag | Intravenöse Formulierungen von PDE-Inhibitoren |
| DE102005009241A1 (de) * | 2005-03-01 | 2006-09-07 | Bayer Healthcare Ag | Arzneiformen mit kontrollierter Bioverfügbarkeit |
| DE102005009240A1 (de) * | 2005-03-01 | 2006-09-07 | Bayer Healthcare Ag | Arzneiformen mit verbesserten pharmakokinetischen Eigenschaften |
| DE602006003416D1 (de) | 2005-03-21 | 2008-12-11 | Pfizer Ltd | Substituierte triazolderivate als oxytocinantagonisten |
| WO2006120552A2 (fr) | 2005-05-12 | 2006-11-16 | Pfizer Inc. | Formes cristallines anhydres de n-[1-(2-ethoxyethyl)-5-(n-ethyl-n-methylamino)-7-(4-methylpyridin-2-yl-amino)-1h-pyrazolo[4,3-d]pyrimidine-3-carbonyl]methanesulfonamide |
| WO2007020521A1 (fr) * | 2005-08-16 | 2007-02-22 | Pharmacia & Upjohn Company Llc | Pyridoyrazinones comme inhibiteurs de la pde-5 |
| AU2006299232A1 (en) * | 2005-09-29 | 2007-04-12 | Bayer Schering Pharma Aktiengesellschaft | PDE inhibitors and combinations thereof for the treatment of urological disorders |
| WO2008151734A1 (fr) * | 2007-06-13 | 2008-12-18 | Bayer Schering Pharma Aktiengesellschaft | Inhibiteurs de la phosphodiestérase (pde) destinés au traitement des troubles de l'audition |
| US9402877B2 (en) | 2011-11-04 | 2016-08-02 | Xion Pharmaceuticals Corporation | Methods and compositions for oral administration of melanocortin receptor agonist compounds |
| WO2013115884A2 (fr) | 2011-11-15 | 2013-08-08 | Trustees Of Boston University | Inhibiteurs de virus, de type pyridopyrimidinone |
| JP6687550B2 (ja) | 2014-06-23 | 2020-04-22 | セルジーン コーポレイション | 肝疾患又は肝機能異常を治療するためのアプレミラスト |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1493685A (en) * | 1970-12-15 | 1977-11-30 | May & Baker Ltd | 8-azapurinones |
| JPS5393520A (en) * | 1977-01-24 | 1978-08-16 | Shin Meiwa Ind Co Ltd | Canopy device for rear body of vehicle |
| SE406624B (sv) * | 1977-07-12 | 1979-02-19 | Stal Laval Turbin Ab | Turbomaskin |
| JPS5670998A (en) * | 1979-11-15 | 1981-06-13 | Toppan Printing Co Ltd | Laser carving method and mask board used for said method |
| ES2058527T3 (es) * | 1988-06-16 | 1994-11-01 | Smith Kline French Lab | Derivados de pirimidina condensados procedimiento y compuestos intermedios para su preparacion y composiciones farmaceuticas que los contienen. |
| US5075310A (en) * | 1988-07-01 | 1991-12-24 | Smith Kline & French Laboratories, Ltd. | Pyrimidone derivatives as bronchodilators |
| JPH0216563U (fr) * | 1988-07-19 | 1990-02-02 | ||
| GB8817651D0 (en) * | 1988-07-25 | 1988-09-01 | Smith Kline French Lab | Chemical compounds |
| GB9013750D0 (en) * | 1990-06-20 | 1990-08-08 | Pfizer Ltd | Therapeutic agents |
| GB9114760D0 (en) * | 1991-07-09 | 1991-08-28 | Pfizer Ltd | Therapeutic agents |
-
1992
- 1992-08-28 GB GB929218322A patent/GB9218322D0/en active Pending
-
1993
- 1993-08-04 DE DE69307712T patent/DE69307712T2/de not_active Expired - Fee Related
- 1993-08-04 CA CA002138298A patent/CA2138298C/fr not_active Expired - Fee Related
- 1993-08-04 EP EP93917761A patent/EP0656898B1/fr not_active Expired - Lifetime
- 1993-08-04 DK DK93917761.4T patent/DK0656898T3/da active
- 1993-08-04 ES ES93917761T patent/ES2096936T3/es not_active Expired - Lifetime
- 1993-08-04 JP JP6506786A patent/JP2660103B2/ja not_active Expired - Fee Related
- 1993-08-04 AT AT93917761T patent/ATE148118T1/de not_active IP Right Cessation
- 1993-08-04 US US08/379,531 patent/US5591742A/en not_active Expired - Fee Related
- 1993-08-04 WO PCT/EP1993/002097 patent/WO1994005661A1/fr active IP Right Grant
-
1995
- 1995-02-27 FI FI950889A patent/FI112484B/fi not_active IP Right Cessation
-
1997
- 1997-03-17 GR GR970400527T patent/GR3022852T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0656898B1 (fr) | 1997-01-22 |
| DE69307712D1 (de) | 1997-03-06 |
| GR3022852T3 (en) | 1997-06-30 |
| DK0656898T3 (da) | 1997-08-18 |
| FI950889A (fi) | 1995-02-27 |
| JPH07506838A (ja) | 1995-07-27 |
| JP2660103B2 (ja) | 1997-10-08 |
| CA2138298A1 (fr) | 1994-03-17 |
| ATE148118T1 (de) | 1997-02-15 |
| FI950889A0 (fi) | 1995-02-27 |
| WO1994005661A1 (fr) | 1994-03-17 |
| ES2096936T3 (es) | 1997-03-16 |
| EP0656898A1 (fr) | 1995-06-14 |
| US5591742A (en) | 1997-01-07 |
| DE69307712T2 (de) | 1997-05-15 |
| GB9218322D0 (en) | 1992-10-14 |
| CA2138298C (fr) | 1998-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |