CN1221545C - 制备4－(杂芳基－甲基)－卤素－1(2h)－2,3－二氮杂萘酮的方法 - Google Patents
制备4－(杂芳基－甲基)－卤素－1(2h)－2,3－二氮杂萘酮的方法 Download PDFInfo
- Publication number
- CN1221545C CN1221545C CNB008175608A CN00817560A CN1221545C CN 1221545 C CN1221545 C CN 1221545C CN B008175608 A CNB008175608 A CN B008175608A CN 00817560 A CN00817560 A CN 00817560A CN 1221545 C CN1221545 C CN 1221545C
- Authority
- CN
- China
- Prior art keywords
- methyl
- reaction
- heteroaryl
- pyridine
- hydrazine hydrate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims abstract description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims abstract description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000005633 phthalidyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 abstract description 3
- 238000010306 acid treatment Methods 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- NIQMWTLRDNQDIA-UHFFFAOYSA-N 4-(pyridin-4-ylmethyl)-2h-phthalazin-1-one Chemical compound C12=CC=CC=C2C(=O)NN=C1CC1=CC=NC=C1 NIQMWTLRDNQDIA-UHFFFAOYSA-N 0.000 abstract 1
- 239000012752 auxiliary agent Substances 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- -1 4-pyridine aldehydes Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- SUMAWDZJEIQACJ-UHFFFAOYSA-N 2-methylpyridine-4-carbaldehyde Chemical compound CC1=CC(C=O)=CC=N1 SUMAWDZJEIQACJ-UHFFFAOYSA-N 0.000 description 1
- JDNSRWWEIXTVPA-UHFFFAOYSA-N 2h-pyrazine-1-carbaldehyde Chemical compound O=CN1CC=NC=C1 JDNSRWWEIXTVPA-UHFFFAOYSA-N 0.000 description 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 description 1
- JFFOBFAGCSLMSV-UHFFFAOYSA-N 3-methylpyridine-4-carbaldehyde Chemical compound CC1=CN=CC=C1C=O JFFOBFAGCSLMSV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- JUTDMVMGNNVIOM-UHFFFAOYSA-N chembl1301287 Chemical compound O=C1C2=CC=CC=C2C(O)=C1C1=CC=NC=C1 JUTDMVMGNNVIOM-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229960001708 magnesium carbonate Drugs 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- DXBWJLDFSICTIH-UHFFFAOYSA-N pyrazine-2-carbaldehyde Chemical compound O=CC1=CN=CC=N1 DXBWJLDFSICTIH-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- OKULHRWWYCFJAB-UHFFFAOYSA-N pyrimidine-4-carbaldehyde Chemical compound O=CC1=CC=NC=N1 OKULHRWWYCFJAB-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000004862 vasculogenesis Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19963607.9 | 1999-12-23 | ||
| DE19963607A DE19963607B4 (de) | 1999-12-23 | 1999-12-23 | Verfahren zur Herstellung von 4-(Heteroaryl-methyl) halogen-1(2H)-phthalazinonen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1413203A CN1413203A (zh) | 2003-04-23 |
| CN1221545C true CN1221545C (zh) | 2005-10-05 |
Family
ID=7934888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB008175608A Expired - Fee Related CN1221545C (zh) | 1999-12-23 | 2000-12-20 | 制备4－(杂芳基－甲基)－卤素－1(2h)－2,3－二氮杂萘酮的方法 |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6891041B2 (enExample) |
| EP (1) | EP1242405B1 (enExample) |
| JP (1) | JP2003529555A (enExample) |
| KR (1) | KR100654265B1 (enExample) |
| CN (1) | CN1221545C (enExample) |
| AT (1) | ATE273972T1 (enExample) |
| AU (1) | AU772981B2 (enExample) |
| BG (1) | BG65387B1 (enExample) |
| BR (1) | BR0016634A (enExample) |
| CA (1) | CA2395407C (enExample) |
| CZ (1) | CZ20022146A3 (enExample) |
| DE (2) | DE19963607B4 (enExample) |
| DK (1) | DK1242405T3 (enExample) |
| EE (1) | EE04940B1 (enExample) |
| ES (1) | ES2223626T3 (enExample) |
| HR (1) | HRP20020605B1 (enExample) |
| HU (1) | HUP0300992A3 (enExample) |
| IL (2) | IL150017A0 (enExample) |
| MX (1) | MXPA02006224A (enExample) |
| NO (1) | NO321357B1 (enExample) |
| NZ (1) | NZ519285A (enExample) |
| PL (1) | PL200714B1 (enExample) |
| PT (1) | PT1242405E (enExample) |
| RO (1) | RO121211B1 (enExample) |
| RS (1) | RS50458B (enExample) |
| RU (1) | RU2250900C2 (enExample) |
| SI (1) | SI1242405T1 (enExample) |
| SK (1) | SK285522B6 (enExample) |
| UA (1) | UA72021C2 (enExample) |
| WO (1) | WO2001047912A1 (enExample) |
| ZA (1) | ZA200205853B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1296984B1 (it) * | 1997-12-19 | 1999-08-03 | Zambon Spa | Derivati ftalazinici inibitori della fosfodiesterasi 4 |
| US7151102B2 (en) * | 2000-10-30 | 2006-12-19 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| GB0419072D0 (en) * | 2004-08-26 | 2004-09-29 | Kudos Pharm Ltd | Phthalazinone derivatives |
| TWI404716B (zh) * | 2006-10-17 | 2013-08-11 | Kudos Pharm Ltd | 酞嗪酮（ｐｈｔｈａｌａｚｉｎｏｎｅ）衍生物 |
| KR101598231B1 (ko) * | 2007-10-17 | 2016-02-26 | 쿠도스 파마슈티칼스 리미티드 | 4-[3-(4-시클로프로판카르보닐-피페라진-1-카르보닐)-4-플루오로-벤질]-2ｈ-프탈라진-1-온 |
| CA2737400C (en) * | 2008-10-07 | 2016-11-22 | Astrazeneca Uk Limited | Pharmaceutical formulation 514 |
| JP6545148B2 (ja) | 2013-03-13 | 2019-07-17 | フラットリー ディスカバリー ラブ，エルエルシー | ピリダジノン化合物及び嚢胞性線維症の治療のための方法 |
| WO2016146303A1 (en) * | 2015-03-19 | 2016-09-22 | Clariant International Ltd | Biodegradable sugar-amide-surfactants for enhanced oil recovery |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE567431A (enExample) * | 1957-05-07 | |||
| GB1293565A (en) * | 1969-05-03 | 1972-10-18 | Aspro Nicholas Ltd | Aminophthalazines and pharmaceutical compositions thereof |
| IE47592B1 (en) * | 1977-12-29 | 1984-05-02 | Ici Ltd | Enzyme inhibitory phthalazin-4-ylacetic acid derivatives, pharmaceutical compositions thereof,and process for their manufacture |
| EP0634404A1 (en) * | 1993-07-13 | 1995-01-18 | Rhone Poulenc Agriculture Ltd. | Phtalazin derivatives and their use as pesticides |
| JP3919835B2 (ja) * | 1994-08-09 | 2007-05-30 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 縮合ピリダジン系化合物 |
| NZ290952A (en) * | 1994-08-09 | 1998-05-27 | Eisai Co Ltd | Phthalazine derivatives optionally substituted in position-1 by (generally benzyl) amino groups |
| RU2128175C1 (ru) * | 1994-08-09 | 1999-03-27 | Эйсай Ко., Лтд. | Конденсированный пиридазин или его фармакологически приемлемая соль, средство, проявляющее ингибирующую активность в отношении циклической гмф- фосфодиэстеразы |
| CA2275686C (en) * | 1996-12-18 | 2006-10-17 | Neurogen Corporation | Isoquinolinamine and phthalazinamine derivatives which interact with crf receptors |
| CO4950519A1 (es) * | 1997-02-13 | 2000-09-01 | Novartis Ag | Ftalazinas, preparaciones farmaceuticas que las comprenden y proceso para su preparacion |
| IT1296984B1 (it) * | 1997-12-19 | 1999-08-03 | Zambon Spa | Derivati ftalazinici inibitori della fosfodiesterasi 4 |
| ITMI981671A1 (it) * | 1998-07-21 | 2000-01-21 | Zambon Spa | Derivati ftalazinici inibitori della fosfodisterasi 4 |
| ITMI981670A1 (it) * | 1998-07-21 | 2000-01-21 | Zambon Spa | Derivati ftalazinici inibitori della fosfodiesterasi 4 |
| ITMI20000261A1 (it) * | 2000-02-16 | 2001-08-16 | Zambon Group | Processo per la preparazione di piridiniliden-ftalidi |
-
1999
- 1999-12-23 DE DE19963607A patent/DE19963607B4/de not_active Expired - Fee Related
-
2000
- 2000-12-20 PL PL355525A patent/PL200714B1/pl not_active IP Right Cessation
- 2000-12-20 DK DK00983354T patent/DK1242405T3/da active
- 2000-12-20 DE DE50007520T patent/DE50007520D1/de not_active Expired - Fee Related
- 2000-12-20 BR BR0016634-0A patent/BR0016634A/pt not_active Application Discontinuation
- 2000-12-20 SK SK892-2002A patent/SK285522B6/sk not_active IP Right Cessation
- 2000-12-20 PT PT00983354T patent/PT1242405E/pt unknown
- 2000-12-20 MX MXPA02006224A patent/MXPA02006224A/es active IP Right Grant
- 2000-12-20 CZ CZ20022146A patent/CZ20022146A3/cs unknown
- 2000-12-20 SI SI200030486T patent/SI1242405T1/xx unknown
- 2000-12-20 US US10/168,794 patent/US6891041B2/en not_active Expired - Fee Related
- 2000-12-20 ES ES00983354T patent/ES2223626T3/es not_active Expired - Lifetime
- 2000-12-20 EP EP00983354A patent/EP1242405B1/de not_active Expired - Lifetime
- 2000-12-20 WO PCT/EP2000/013027 patent/WO2001047912A1/de not_active Ceased
- 2000-12-20 UA UA2002076049A patent/UA72021C2/uk unknown
- 2000-12-20 JP JP2001549382A patent/JP2003529555A/ja active Pending
- 2000-12-20 HR HR20020605A patent/HRP20020605B1/xx not_active IP Right Cessation
- 2000-12-20 RS YUP-473/02A patent/RS50458B/sr unknown
- 2000-12-20 RU RU2002119559/04A patent/RU2250900C2/ru not_active IP Right Cessation
- 2000-12-20 AU AU20122/01A patent/AU772981B2/en not_active Ceased
- 2000-12-20 HU HU0300992A patent/HUP0300992A3/hu unknown
- 2000-12-20 CN CNB008175608A patent/CN1221545C/zh not_active Expired - Fee Related
- 2000-12-20 AT AT00983354T patent/ATE273972T1/de not_active IP Right Cessation
- 2000-12-20 EE EEP200200307A patent/EE04940B1/xx not_active IP Right Cessation
- 2000-12-20 RO ROA200200653A patent/RO121211B1/ro unknown
- 2000-12-20 KR KR1020027007997A patent/KR100654265B1/ko not_active Expired - Fee Related
- 2000-12-20 NZ NZ519285A patent/NZ519285A/xx unknown
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