NO313292B1 - Forbedret fremgangsmåte for fremstilling av tiazolidindioner, nye tiazolidindioner, anvendelse derav samt legemiddel - Google Patents
Forbedret fremgangsmåte for fremstilling av tiazolidindioner, nye tiazolidindioner, anvendelse derav samt legemiddel Download PDFInfo
- Publication number
- NO313292B1 NO313292B1 NO19994505A NO994505A NO313292B1 NO 313292 B1 NO313292 B1 NO 313292B1 NO 19994505 A NO19994505 A NO 19994505A NO 994505 A NO994505 A NO 994505A NO 313292 B1 NO313292 B1 NO 313292B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- salts
- compounds
- ethoxy
- thiazolidinediones
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000003814 drug Substances 0.000 title claims description 5
- 150000001467 thiazolidinediones Chemical class 0.000 title description 5
- 229940123464 Thiazolidinedione Drugs 0.000 title description 4
- 229940079593 drug Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000003586 protic polar solvent Substances 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical group O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- JFFJKYJTOPCQCK-UHFFFAOYSA-N 5-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]naphthalen-1-yl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C1=CC=CC=C11)=CC=C1C=C1SC(=O)NC1=O JFFJKYJTOPCQCK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001398 aluminium Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- -1 ethylene-iamine Chemical compound 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Endocrinology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19711616A DE19711616A1 (de) | 1997-03-20 | 1997-03-20 | Verbessertes Verfahren zur Herstellung von Thiazolidindionen |
| PCT/EP1998/001535 WO1998042704A1 (de) | 1997-03-20 | 1998-03-17 | Verbessertes verfahren zur herstellung von thiazolidindionen und neue thiazolidindione |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO994505D0 NO994505D0 (no) | 1999-09-17 |
| NO994505L NO994505L (no) | 1999-11-17 |
| NO313292B1 true NO313292B1 (no) | 2002-09-09 |
Family
ID=7824011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19994505A NO313292B1 (no) | 1997-03-20 | 1999-09-17 | Forbedret fremgangsmåte for fremstilling av tiazolidindioner, nye tiazolidindioner, anvendelse derav samt legemiddel |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US6258832B1 (zh) |
| EP (1) | EP0970077B1 (zh) |
| JP (2) | JP3484200B2 (zh) |
| KR (1) | KR100340353B1 (zh) |
| CN (1) | CN1105718C (zh) |
| AR (1) | AR012124A1 (zh) |
| AT (1) | ATE240324T1 (zh) |
| AU (1) | AU726048B2 (zh) |
| BR (1) | BR9808029A (zh) |
| CA (1) | CA2285208C (zh) |
| DE (2) | DE19711616A1 (zh) |
| DK (1) | DK0970077T3 (zh) |
| ES (1) | ES2198053T3 (zh) |
| HK (1) | HK1025965A1 (zh) |
| HU (1) | HUP0001551A3 (zh) |
| IL (1) | IL131772A (zh) |
| NO (1) | NO313292B1 (zh) |
| NZ (1) | NZ337608A (zh) |
| PL (1) | PL192201B1 (zh) |
| PT (1) | PT970077E (zh) |
| RS (1) | RS49771B (zh) |
| RU (1) | RU2181724C2 (zh) |
| TR (1) | TR199902197T2 (zh) |
| TW (1) | TW487707B (zh) |
| WO (1) | WO1998042704A1 (zh) |
| ZA (1) | ZA982326B (zh) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1078923E (pt) | 1999-08-02 | 2006-07-31 | Hoffmann La Roche | Processo para a preparacao de derivados de benzotiofeno |
| US6531609B2 (en) * | 2000-04-14 | 2003-03-11 | Hoffmann-La Roche Inc. | Process for the preparation of thiazolidinedione derivatives |
| FR2820742B1 (fr) * | 2001-02-14 | 2005-03-11 | Ppg Sipsy | Procede de preparation de composes derives de thiazolidinedione, d'oxazolidinedione ou d'hydantoine |
| FR2820741A1 (fr) * | 2001-02-14 | 2002-08-16 | Ppg Sipsy | Procede de preparation de composes derives de thiazolidinedione, d'oxazolidinedione ou d'hydantoine |
| US7323481B2 (en) | 2001-04-06 | 2008-01-29 | Hoffmann-La Roche Inc. | Thiazolidinediones alone or in combination with other therapeutic agents for inhibiting or reducing tumour growth |
| RU2278859C2 (ru) * | 2001-05-15 | 2006-06-27 | Ф.Хоффманн-Ля Рош Аг | Замещенные карбоновыми кислотами оксазоловые производные в качестве ppar-альфа и гамма-активаторов при лечении диабета |
| ES2291688T3 (es) * | 2002-07-03 | 2008-03-01 | F. Hoffmann-La Roche Ag | Derivados de oxazol y su empleo como sensibilizadores a la insulina. |
| RU2296754C2 (ru) * | 2002-08-30 | 2007-04-10 | Ф.Хоффманн-Ля Рош Аг | НОВЫЕ СОЕДИНЕНИЯ 2-АРИЛТИАЗОЛА В КАЧЕСТВЕ АГОНИСТОВ PPAR α И PPAR γ |
| BR0314261A (pt) * | 2002-09-12 | 2005-07-26 | Hoffmann La Roche | Compostos, processo de preparação de um composto, composição farmacêutica que compreende o mesmo, utilização de um composto, método para tratamento e/ou profilaxia de enfermidades e utilização e/ou método de tratamento |
| JP4384052B2 (ja) * | 2002-11-25 | 2009-12-16 | エフ．ホフマン−ラ ロシュ アーゲー | インドリル誘導体 |
| CA2530309A1 (en) * | 2003-06-26 | 2005-01-06 | F. Hoffmann-La Roche Ag | Process for the preparation of insulin sensitizer and intermediate compound thereof |
| US20210172624A1 (en) | 2019-12-10 | 2021-06-10 | Lg Electronics Inc. | Air management apparatus or device |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1003445B (zh) | 1984-10-03 | 1989-03-01 | 武田药品工业株式会社 | 噻唑烷二酮衍生物，其制备方法和用途 |
| US4703052A (en) | 1985-05-21 | 1987-10-27 | Pfizer Inc. | Hypoglycemic thiazolidinediones |
| GB8713861D0 (en) | 1987-06-13 | 1987-07-15 | Beecham Group Plc | Compounds |
| ATE186724T1 (de) * | 1987-09-04 | 1999-12-15 | Beecham Group Plc | Substituierte thiazolidindionderivate |
| US5330998A (en) | 1988-03-08 | 1994-07-19 | Pfizer Inc. | Thiazolidinedione derivatives as hypoglycemic agents |
| MX15171A (es) | 1988-03-08 | 1993-05-01 | Pfizer | Derivados de tiazolidinodiona hipoglicemicos |
| US5061717A (en) | 1988-03-08 | 1991-10-29 | Pfizer Inc. | Thiazolidinedione hypoglycemic agents |
| HU217432B (hu) | 1988-03-08 | 2000-01-28 | Pfizer Inc. | Eljárás tiazolidin-dion-származékok és az ezeket tartalmazó gyógyszerkészítmények előállítására, a vegyületek és a készítmények |
| ATE205206T1 (de) * | 1990-04-27 | 2001-09-15 | Sankyo Co | Benzylidenthiazolidinderivate, ihre herstellung und ihre anwendung als lipidperoxid-inhibitoren |
| JPH0678326B2 (ja) | 1990-08-23 | 1994-10-05 | フアイザー・インコーポレイテツド | 血糖低下性ヒドロキシ尿素誘導体 |
| WO1993013095A1 (en) | 1991-12-20 | 1993-07-08 | The Upjohn Company | A reduction method for substituted 5-methylene-thiazolidinediones |
| FR2688220A1 (fr) | 1992-03-06 | 1993-09-10 | Adir | Nouveaux derives de thiazolidine-2,4-dione, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| DE4317320A1 (de) * | 1993-05-25 | 1994-12-01 | Boehringer Mannheim Gmbh | Neue Thiazolidindione und diese enthaltende Arzneimittel |
| DK0684242T3 (da) | 1993-12-27 | 1999-11-01 | Japan Tobacco Inc | Isoxazolidindionderivat og anvendelse deraf |
-
1997
- 1997-03-20 DE DE19711616A patent/DE19711616A1/de not_active Withdrawn
-
1998
- 1998-03-17 NZ NZ337608A patent/NZ337608A/en unknown
- 1998-03-17 RS YUP-466/99A patent/RS49771B/sr unknown
- 1998-03-17 IL IL13177298A patent/IL131772A/en not_active IP Right Cessation
- 1998-03-17 RU RU99122023/04A patent/RU2181724C2/ru not_active IP Right Cessation
- 1998-03-17 AU AU70361/98A patent/AU726048B2/en not_active Ceased
- 1998-03-17 CA CA002285208A patent/CA2285208C/en not_active Expired - Fee Related
- 1998-03-17 ES ES98916974T patent/ES2198053T3/es not_active Expired - Lifetime
- 1998-03-17 PT PT98916974T patent/PT970077E/pt unknown
- 1998-03-17 WO PCT/EP1998/001535 patent/WO1998042704A1/de active IP Right Grant
- 1998-03-17 CN CN98803388A patent/CN1105718C/zh not_active Expired - Fee Related
- 1998-03-17 US US09/381,247 patent/US6258832B1/en not_active Expired - Fee Related
- 1998-03-17 PL PL335903A patent/PL192201B1/pl not_active IP Right Cessation
- 1998-03-17 TR TR1999/02197T patent/TR199902197T2/xx unknown
- 1998-03-17 DK DK98916974T patent/DK0970077T3/da active
- 1998-03-17 JP JP54484098A patent/JP3484200B2/ja not_active Expired - Fee Related
- 1998-03-17 HU HU0001551A patent/HUP0001551A3/hu unknown
- 1998-03-17 TW TW087103935A patent/TW487707B/zh not_active IP Right Cessation
- 1998-03-17 DE DE59808365T patent/DE59808365D1/de not_active Expired - Fee Related
- 1998-03-17 EP EP98916974A patent/EP0970077B1/de not_active Expired - Lifetime
- 1998-03-17 AT AT98916974T patent/ATE240324T1/de not_active IP Right Cessation
- 1998-03-17 KR KR1019997008445A patent/KR100340353B1/ko not_active IP Right Cessation
- 1998-03-17 BR BR9808029-6A patent/BR9808029A/pt not_active Application Discontinuation
- 1998-03-19 ZA ZA9802326A patent/ZA982326B/xx unknown
- 1998-03-20 AR ARP980101266A patent/AR012124A1/es active IP Right Grant
-
1999
- 1999-09-17 NO NO19994505A patent/NO313292B1/no unknown
-
2000
- 2000-08-18 HK HK00105205A patent/HK1025965A1/xx not_active IP Right Cessation
-
2001
- 2001-02-14 US US09/783,494 patent/US6441185B2/en not_active Expired - Fee Related
-
2003
- 2003-08-21 JP JP2003297751A patent/JP2004067697A/ja active Pending
Also Published As
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