JP2011500537A - Ｈ１受容体アンタゴニストとしてのフタラジンおよびピリド［３，４−ｄ］ピリダジン化合物 - Google Patents
Ｈ１受容体アンタゴニストとしてのフタラジンおよびピリド［３，４−ｄ］ピリダジン化合物 Download PDFInfo
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- JP2011500537A JP2011500537A JP2010528414A JP2010528414A JP2011500537A JP 2011500537 A JP2011500537 A JP 2011500537A JP 2010528414 A JP2010528414 A JP 2010528414A JP 2010528414 A JP2010528414 A JP 2010528414A JP 2011500537 A JP2011500537 A JP 2011500537A
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- Prior art keywords
- methyl
- chlorophenyl
- formula
- pyrrolidinyl
- acid
- 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.)
- Ceased
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- 108090000110 Histamine H1 Receptors Proteins 0.000 title description 14
- 229940044551 receptor antagonist Drugs 0.000 title description 7
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- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 title 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 title 1
- IHYJXEQIZYROGA-UHFFFAOYSA-N pyrido[3,4-d]pyridazine Chemical class N1=NC=C2C=NC=CC2=C1 IHYJXEQIZYROGA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 268
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 18
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
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- 125000003118 aryl group Chemical group 0.000 claims description 7
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
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- YXICCMIPIPEESR-SIKLNZKXSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-[(3s)-3-ethylsulfonylbutyl]pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCS(=O)(=O)[C@@H](C)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YXICCMIPIPEESR-SIKLNZKXSA-N 0.000 claims description 3
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- TWRLBTGKEAFDGO-LJQANCHMSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(2-ethylsulfonylethyl)pyrrolidin-2-yl]methyl]pyrido[3,4-d]pyridazin-1-one Chemical compound CCS(=O)(=O)CCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 TWRLBTGKEAFDGO-LJQANCHMSA-N 0.000 claims description 2
- OVMCRVJLHVRHKE-HSZRJFAPSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(2-piperidin-1-ylsulfonylethyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C[C@@H]1N(CCS(=O)(=O)N2CCCCC2)CCC1 OVMCRVJLHVRHKE-HSZRJFAPSA-N 0.000 claims description 2
- YXICCMIPIPEESR-AVKWCDSFSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(3-ethylsulfonylbutyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCS(=O)(=O)C(C)CCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YXICCMIPIPEESR-AVKWCDSFSA-N 0.000 claims description 2
- DLHRVVJGYOTOOA-OAQYLSRUSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(3-ethylsulfonylpropyl)pyrrolidin-2-yl]methyl]phthalazin-1-one Chemical compound CCS(=O)(=O)CCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 DLHRVVJGYOTOOA-OAQYLSRUSA-N 0.000 claims description 2
- JETJHTYYZHIZRJ-HXUWFJFHSA-N 4-[(4-chlorophenyl)methyl]-2-[[(2r)-1-(3-ethylsulfonylpropyl)pyrrolidin-2-yl]methyl]pyrido[3,4-d]pyridazin-1-one Chemical compound CCS(=O)(=O)CCCN1CCC[C@@H]1CN1C(=O)C2=CC=NC=C2C(CC=2C=CC(Cl)=CC=2)=N1 JETJHTYYZHIZRJ-HXUWFJFHSA-N 0.000 claims description 2
- 125000005275 alkylenearyl group Chemical group 0.000 claims description 2
- VTQRKNRZSDZHPN-HXUWFJFHSA-N n-[2-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]ethyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 VTQRKNRZSDZHPN-HXUWFJFHSA-N 0.000 claims description 2
- YOJGSGWWEUHPBC-JOCHJYFZSA-N n-[4-[(2r)-2-[[4-[(4-chlorophenyl)methyl]-1-oxophthalazin-2-yl]methyl]pyrrolidin-1-yl]butyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NCCCCN1CCC[C@@H]1CN1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YOJGSGWWEUHPBC-JOCHJYFZSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 195
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- 239000002904 solvent Substances 0.000 description 80
- 239000000543 intermediate Substances 0.000 description 69
- 239000000243 solution Substances 0.000 description 65
- -1 n- Hexyl Chemical group 0.000 description 56
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- 238000002360 preparation method Methods 0.000 description 48
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
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- UISARWKNNNHPGI-UHFFFAOYSA-N terodiline Chemical compound C=1C=CC=CC=1C(CC(C)NC(C)(C)C)C1=CC=CC=C1 UISARWKNNNHPGI-UHFFFAOYSA-N 0.000 description 1
- BFFLLBPMZCIGRM-QMMMGPOBSA-N tert-butyl (2s)-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1CO BFFLLBPMZCIGRM-QMMMGPOBSA-N 0.000 description 1
- CVXMKJURRKNXKA-UHFFFAOYSA-N tert-butyl 2-(4-chlorophenyl)acetate Chemical compound CC(C)(C)OC(=O)CC1=CC=C(Cl)C=C1 CVXMKJURRKNXKA-UHFFFAOYSA-N 0.000 description 1
- YDPHNHBVCNPHHZ-UHFFFAOYSA-N tert-butyl 4-hydroxy-2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC=C(O)C=C1 YDPHNHBVCNPHHZ-UHFFFAOYSA-N 0.000 description 1
- TZRQZPMQUXEZMC-UHFFFAOYSA-N tert-butyl n-(2-bromoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCBr TZRQZPMQUXEZMC-UHFFFAOYSA-N 0.000 description 1
- VDFBCTSISJDKNW-UHFFFAOYSA-N tert-butyl n-(3-bromophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC(Br)=C1 VDFBCTSISJDKNW-UHFFFAOYSA-N 0.000 description 1
- NXQXVXILNVTMNA-UHFFFAOYSA-N tert-butyl n-(6-bromohexyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCBr NXQXVXILNVTMNA-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical compound O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 1
- 229940110309 tiotropium Drugs 0.000 description 1
- 229960004045 tolterodine Drugs 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 229960001530 trospium chloride Drugs 0.000 description 1
- RVCSYOQWLPPAOA-DHWZJIOFSA-M trospium chloride Chemical compound [Cl-].[N+]12([C@@H]3CC[C@H]2CC(C3)OC(=O)C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CCCC1 RVCSYOQWLPPAOA-DHWZJIOFSA-M 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229940063390 vesicare Drugs 0.000 description 1
- DAFYYTQWSAWIGS-DEOSSOPVSA-N vilanterol Chemical compound C1=C(O)C(CO)=CC([C@@H](O)CNCCCCCCOCCOCC=2C(=CC=CC=2Cl)Cl)=C1 DAFYYTQWSAWIGS-DEOSSOPVSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XOFLBQFBSOEHOG-UUOKFMHZSA-N γS-GTP Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=S)[C@@H](O)[C@H]1O XOFLBQFBSOEHOG-UUOKFMHZSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- 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
- C07D471/04—Ortho-condensed 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)
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97910507P | 2007-10-11 | 2007-10-11 | |
| PCT/EP2008/063642 WO2009047336A1 (en) | 2007-10-11 | 2008-10-10 | Phthalazine and pyrido [3,4-d] pyridaz ine compounds as h1 receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011500537A true JP2011500537A (ja) | 2011-01-06 |
| JP2011500537A5 JP2011500537A5 (enExample) | 2011-12-01 |
Family
ID=40104668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010528414A Ceased JP2011500537A (ja) | 2007-10-11 | 2008-10-10 | Ｈ１受容体アンタゴニストとしてのフタラジンおよびピリド［３，４−ｄ］ピリダジン化合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20100216799A1 (enExample) |
| EP (1) | EP2215082B1 (enExample) |
| JP (1) | JP2011500537A (enExample) |
| AT (1) | ATE525370T1 (enExample) |
| ES (1) | ES2369320T3 (enExample) |
| WO (1) | WO2009047336A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006115221A1 (ja) * | 2005-04-21 | 2006-11-02 | Nippon Shinyaku Co., Ltd. | フタラジノン誘導体及びその医薬 |
| UA97506C2 (xx) * | 2006-12-28 | 2012-02-27 | Эбботт Лаборетриз | Інгібітори полі(adp-рибозо)полімерази$ингибиторы поли(adp-рибозо)полимеразы |
| CA2685219C (en) * | 2007-05-04 | 2012-06-19 | Amgen Inc. | Diazaquinolones that inhibit prolyl hydroxylase activity |
| CN115135315B (zh) | 2019-12-20 | 2024-11-26 | 米拉蒂治疗股份有限公司 | Sos1抑制剂 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60185777A (ja) * | 1984-01-09 | 1985-09-21 | ジヤンセン・フア−マシユ−チカ・ナ−ムロ−ゼ・フエンノ−トシヤツプ | ４―〔（二環式複素環）―メチル及びヘテロ〕ピペリジン類及びその製法 |
| JPS62114987A (ja) * | 1985-11-11 | 1987-05-26 | アスタ・メディカ・アクチエンゲゼルシャフト | 新規４―ベンジル―１―（２ｈ）―フタラジノン―誘導体及びその製法 |
| JP2005501085A (ja) * | 2001-08-07 | 2005-01-13 | フアルマシア・イタリア・エツセ・ピー・アー | キナーゼ阻害剤として活性なアミノフタラジノン誘導体、それらを調製する方法およびそれらを含有する薬剤組成物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3813384A (en) * | 1972-01-17 | 1974-05-28 | Asta Werke Ag Chem Fab | Basically substituted benzyl phthalazone derivatives,acid salts thereof and process for the production thereof |
| DE3575135D1 (de) * | 1984-09-14 | 1990-02-08 | Asta Pharma Ag | Substituierte benzylphthalazinon-derivate. |
| DE3634942A1 (de) * | 1985-11-11 | 1987-05-14 | Asta Werke Ag Chem Fab | Neue 4-benzyl-1-(2h)-phthalazinon-derivate |
| EP0289939A1 (de) * | 1987-05-08 | 1988-11-09 | ASTA Pharma AG | Neue 4-Benzyl-1-(2H)-phthalazinon-Derivate mit einem Aminosäurerest |
| CZ199593A3 (en) * | 1992-10-02 | 1994-04-13 | Asta Medica Ag | Phthalazinone derivatives exhibiting anti-arrhythmic and analgesic activity and eliminating resistance to a plurality of medicaments (mdr) |
| 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 |
| ES2209337T3 (es) * | 1998-08-14 | 2004-06-16 | Pfizer Inc. | Agentes antitromboticos. |
| CA2519220A1 (en) * | 2003-03-18 | 2004-09-30 | Merck & Co., Inc. | Amino cyclobutylamide modulators of chemokine receptor activity |
| JP4735261B2 (ja) * | 2003-06-27 | 2011-07-27 | Ｍｓｄ株式会社 | ヘテロアリールオキシ含窒素飽和ヘテロ環誘導体 |
| ES2341813T3 (es) * | 2006-12-20 | 2010-06-28 | Glaxo Group Limited | 4-bencil-1 (2h)-ftalazinonas como antagonistas del receptor h1. |
-
2008
- 2008-10-10 EP EP08805231A patent/EP2215082B1/en not_active Not-in-force
- 2008-10-10 JP JP2010528414A patent/JP2011500537A/ja not_active Ceased
- 2008-10-10 WO PCT/EP2008/063642 patent/WO2009047336A1/en not_active Ceased
- 2008-10-10 US US12/681,945 patent/US20100216799A1/en not_active Abandoned
- 2008-10-10 ES ES08805231T patent/ES2369320T3/es active Active
- 2008-10-10 AT AT08805231T patent/ATE525370T1/de not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60185777A (ja) * | 1984-01-09 | 1985-09-21 | ジヤンセン・フア−マシユ−チカ・ナ−ムロ−ゼ・フエンノ−トシヤツプ | ４―〔（二環式複素環）―メチル及びヘテロ〕ピペリジン類及びその製法 |
| JPS62114987A (ja) * | 1985-11-11 | 1987-05-26 | アスタ・メディカ・アクチエンゲゼルシャフト | 新規４―ベンジル―１―（２ｈ）―フタラジノン―誘導体及びその製法 |
| JP2005501085A (ja) * | 2001-08-07 | 2005-01-13 | フアルマシア・イタリア・エツセ・ピー・アー | キナーゼ阻害剤として活性なアミノフタラジノン誘導体、それらを調製する方法およびそれらを含有する薬剤組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009047336A1 (en) | 2009-04-16 |
| EP2215082B1 (en) | 2011-09-21 |
| EP2215082A1 (en) | 2010-08-11 |
| US20100216799A1 (en) | 2010-08-26 |
| ES2369320T3 (es) | 2011-11-29 |
| ATE525370T1 (de) | 2011-10-15 |
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