SK3712001A3 - Benzoxazine and benzothiazine derivatives and their use in medicines - Google Patents
Benzoxazine and benzothiazine derivatives and their use in medicines Download PDFInfo
- Publication number
- SK3712001A3 SK3712001A3 SK371-2001A SK3712001A SK3712001A3 SK 3712001 A3 SK3712001 A3 SK 3712001A3 SK 3712001 A SK3712001 A SK 3712001A SK 3712001 A3 SK3712001 A3 SK 3712001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- methyl
- amino
- group
- carbon atoms
- aminomethyl
- Prior art date
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- 239000003814 drug Substances 0.000 title claims abstract description 9
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title claims description 12
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical class C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 title claims 8
- 229940079593 drug Drugs 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- -1 = N-NH-aryl Chemical group 0.000 claims description 136
- 125000004432 carbon atom Chemical group C* 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical compound C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- SYCFXYZHEGWMKD-UHFFFAOYSA-N 2-methyl-1,4-benzoxazin-2-amine Chemical compound C1=CC=C2N=CC(C)(N)OC2=C1 SYCFXYZHEGWMKD-UHFFFAOYSA-N 0.000 claims 1
- LVPQWZMSHDHTJO-UHFFFAOYSA-N 2-methyl-2h-1,4-benzoxazin-3-amine Chemical compound C1=CC=C2N=C(N)C(C)OC2=C1 LVPQWZMSHDHTJO-UHFFFAOYSA-N 0.000 claims 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 61
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 59
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 49
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- FBOSKQVOIHEWAX-UHFFFAOYSA-N benzothiazine Chemical class C1=CC=C2N=CCSC2=C1 FBOSKQVOIHEWAX-UHFFFAOYSA-N 0.000 description 5
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- 239000000047 product Substances 0.000 description 5
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- QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 description 4
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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- 150000001409 amidines Chemical class 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 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 4
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- 239000003112 inhibitor Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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- 238000004587 chromatography analysis Methods 0.000 description 3
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- 238000004440 column chromatography Methods 0.000 description 3
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/16—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Psychology (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Transplantation (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19844291A DE19844291A1 (de) | 1998-09-18 | 1998-09-18 | Benzoxazin- und Benzothiazin-Derivate und deren Verwendung in Arzneimitteln |
| PCT/EP1999/007089 WO2000017173A1 (de) | 1998-09-18 | 1999-09-16 | Benzoxazin- und benzothiazin-derivate und deren verwendung in arzneimitteln |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK3712001A3 true SK3712001A3 (en) | 2001-09-11 |
Family
ID=7882416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK371-2001A SK3712001A3 (en) | 1998-09-18 | 1999-09-16 | Benzoxazine and benzothiazine derivatives and their use in medicines |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6841550B1 (hu) |
| EP (1) | EP1114037B1 (hu) |
| JP (1) | JP2002526481A (hu) |
| KR (1) | KR20010075199A (hu) |
| CN (1) | CN1144794C (hu) |
| AR (1) | AR020474A1 (hu) |
| AT (1) | ATE266647T1 (hu) |
| AU (1) | AU751381B2 (hu) |
| BR (1) | BR9913856A (hu) |
| CA (1) | CA2341170A1 (hu) |
| CZ (1) | CZ2001988A3 (hu) |
| DE (2) | DE19844291A1 (hu) |
| DK (1) | DK1114037T3 (hu) |
| ES (1) | ES2221442T3 (hu) |
| HU (1) | HUP0103505A3 (hu) |
| NO (1) | NO20011339L (hu) |
| NZ (1) | NZ510562A (hu) |
| PE (1) | PE20001035A1 (hu) |
| PL (1) | PL346699A1 (hu) |
| PT (1) | PT1114037E (hu) |
| SK (1) | SK3712001A3 (hu) |
| WO (1) | WO2000017173A1 (hu) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10020667A1 (de) * | 2000-04-19 | 2001-11-22 | Schering Ag | Neue Benzoxazin- und Benzothiazin-Derivate und deren Verwendung in Arzneimitteln |
| AU2001262200A1 (en) * | 2000-04-25 | 2001-11-07 | Schering Aktiengesellschaft | Benzoxazine derivatives and benzothiazine derivatives having nos-inhibitory and antioxidant properties |
| UA105182C2 (ru) * | 2008-07-03 | 2014-04-25 | Ньюрексон, Інк. | Бензоксазины, бензотиазины и родственные соединения, которые имеют ингибирующую nos активность |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2509155A1 (de) * | 1975-03-03 | 1976-09-09 | Hoechst Ag | 1,4-benzoxazinderivate und verfahren zu ihrer herstellung |
| US4254121A (en) * | 1979-08-13 | 1981-03-03 | Ayerst, Mckenna & Harrison Inc. | 3-Oxo-5H-pyrimido[2,1-c][1,4 ]benzoxazines |
| US4254118A (en) * | 1979-08-13 | 1981-03-03 | Ayerst, Mckenna & Harrison Inc. | 1-Oxo-5H-pyrimido[2,1-c][1,4]benzthiazine-2-carboxylic acid esters |
| US4547499A (en) * | 1984-05-10 | 1985-10-15 | The Upjohn Company | 2,4-Dihydro-2(omega-aminoalkyl)-1H-[1,2,4]triazolo[3,4-c]benzoxazin-1-one anti-allergy drug compounds, compositions and use |
| RU2136661C1 (ru) * | 1993-10-21 | 1999-09-10 | Джи Ди Сирл энд Ко. | Амидинопроизводные, их применение и фармацевтическая композиция |
| US5629322A (en) * | 1994-11-15 | 1997-05-13 | Merck & Co., Inc. | Cyclic amidine analogs as inhibitors of nitric oxide synthase |
| DE4442116A1 (de) * | 1994-11-25 | 1996-05-30 | Cassella Ag | 2-Amino-1,3-thiazine als Hemmstoffe der Stickstoffmonoxid-Synthase |
| DE19530870A1 (de) * | 1994-12-14 | 1996-06-20 | Japan Tobacco Inc | Thiazin- oder Thiazepinderivate |
| TW397812B (en) * | 1995-02-11 | 2000-07-11 | Astra Ab | Bicyclic isothiourea derivatives useful in therapy |
| CZ287969B6 (cs) * | 1995-08-10 | 2001-03-14 | Astra Pharmaceuticals Limited | Amidinový derivát, způsob jeho přípravy, farmaceutický prostředek s jeho obsahem a použití |
| TW440563B (en) * | 1996-05-23 | 2001-06-16 | Hoffmann La Roche | Aryl pyrimidine derivatives and a pharmaceutical composition thereof |
| EP0906294B1 (en) * | 1996-05-29 | 2003-01-29 | Warner-Lambert Company | Benzoxazinone dopamine d4 receptor antagonists |
| ATE336485T1 (de) * | 1997-05-02 | 2006-09-15 | Schering Ag | Substituierte heterocyclen und deren verwendung in arzneimitteln |
| DE59810359D1 (de) | 1997-09-08 | 2004-01-15 | Schering Ag | Benzoxazin- und benzothiazin-derivate und deren verwendung in arzneimitteln |
-
1998
- 1998-09-18 DE DE19844291A patent/DE19844291A1/de not_active Withdrawn
-
1999
- 1999-09-15 PE PE1999000934A patent/PE20001035A1/es not_active Application Discontinuation
- 1999-09-16 PT PT99948841T patent/PT1114037E/pt unknown
- 1999-09-16 AT AT99948841T patent/ATE266647T1/de not_active IP Right Cessation
- 1999-09-16 US US09/787,396 patent/US6841550B1/en not_active Expired - Fee Related
- 1999-09-16 JP JP2000574083A patent/JP2002526481A/ja active Pending
- 1999-09-16 PL PL99346699A patent/PL346699A1/xx not_active Application Discontinuation
- 1999-09-16 ES ES99948841T patent/ES2221442T3/es not_active Expired - Lifetime
- 1999-09-16 KR KR1020017003496A patent/KR20010075199A/ko not_active Application Discontinuation
- 1999-09-16 DE DE59909486T patent/DE59909486D1/de not_active Expired - Fee Related
- 1999-09-16 BR BR9913856-5A patent/BR9913856A/pt not_active IP Right Cessation
- 1999-09-16 NZ NZ510562A patent/NZ510562A/en unknown
- 1999-09-16 AU AU61954/99A patent/AU751381B2/en not_active Ceased
- 1999-09-16 WO PCT/EP1999/007089 patent/WO2000017173A1/de not_active Application Discontinuation
- 1999-09-16 EP EP99948841A patent/EP1114037B1/de not_active Expired - Lifetime
- 1999-09-16 DK DK99948841T patent/DK1114037T3/da active
- 1999-09-16 CN CNB998111244A patent/CN1144794C/zh not_active Expired - Fee Related
- 1999-09-16 CZ CZ2001988A patent/CZ2001988A3/cs unknown
- 1999-09-16 HU HU0103505A patent/HUP0103505A3/hu unknown
- 1999-09-16 CA CA002341170A patent/CA2341170A1/en not_active Abandoned
- 1999-09-16 SK SK371-2001A patent/SK3712001A3/sk unknown
- 1999-09-17 AR ARP990104683A patent/AR020474A1/es unknown
-
2001
- 2001-03-16 NO NO20011339A patent/NO20011339L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PT1114037E (pt) | 2004-09-30 |
| WO2000017173A1 (de) | 2000-03-30 |
| CN1319097A (zh) | 2001-10-24 |
| ES2221442T3 (es) | 2004-12-16 |
| AU6195499A (en) | 2000-04-10 |
| DE19844291A1 (de) | 2000-03-23 |
| HUP0103505A3 (en) | 2003-05-28 |
| CN1144794C (zh) | 2004-04-07 |
| JP2002526481A (ja) | 2002-08-20 |
| AR020474A1 (es) | 2002-05-15 |
| NO20011339D0 (no) | 2001-03-16 |
| DK1114037T3 (da) | 2004-08-16 |
| ATE266647T1 (de) | 2004-05-15 |
| NO20011339L (no) | 2001-05-09 |
| CZ2001988A3 (cs) | 2001-08-15 |
| PE20001035A1 (es) | 2000-10-18 |
| NZ510562A (en) | 2003-08-29 |
| HUP0103505A2 (hu) | 2002-02-28 |
| DE59909486D1 (de) | 2004-06-17 |
| BR9913856A (pt) | 2001-06-12 |
| EP1114037B1 (de) | 2004-05-12 |
| US6841550B1 (en) | 2005-01-11 |
| EP1114037A1 (de) | 2001-07-11 |
| CA2341170A1 (en) | 2000-03-30 |
| AU751381B2 (en) | 2002-08-15 |
| KR20010075199A (ko) | 2001-08-09 |
| PL346699A1 (en) | 2002-02-25 |
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