NO322362B1 - Substituerte homopiperidinylbenzimidazolanaloger som fundiske relaksanter - Google Patents
Substituerte homopiperidinylbenzimidazolanaloger som fundiske relaksanter Download PDFInfo
- Publication number
- NO322362B1 NO322362B1 NO20022977A NO20022977A NO322362B1 NO 322362 B1 NO322362 B1 NO 322362B1 NO 20022977 A NO20022977 A NO 20022977A NO 20022977 A NO20022977 A NO 20022977A NO 322362 B1 NO322362 B1 NO 322362B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- formula
- aryl
- hydroxy
- compound
- Prior art date
Links
- 239000002249 anxiolytic agent Substances 0.000 title description 3
- LQDRHXXAOXZUME-UHFFFAOYSA-N 2-(azepan-1-yl)-1h-benzimidazole Chemical class C1CCCCCN1C1=NC2=CC=CC=C2N1 LQDRHXXAOXZUME-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 154
- -1 nitro, amino, hydroxy Chemical group 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002348 vinylic group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 11
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 112
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 92
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 62
- 239000002904 solvent Substances 0.000 description 61
- 239000000543 intermediate Substances 0.000 description 33
- 239000012074 organic phase Substances 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
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- 150000003254 radicals Chemical class 0.000 description 27
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000003480 eluent Substances 0.000 description 20
- 238000004440 column chromatography Methods 0.000 description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 19
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- 229910002027 silica gel Inorganic materials 0.000 description 19
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 18
- 235000011114 ammonium hydroxide Nutrition 0.000 description 18
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- 230000002496 gastric effect Effects 0.000 description 15
- 150000002431 hydrogen Chemical class 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 210000002784 stomach Anatomy 0.000 description 13
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
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- 208000024891 symptom Diseases 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 208000024798 heartburn Diseases 0.000 description 8
- 230000001771 impaired effect Effects 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
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- 239000000843 powder Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Chemical class 0.000 description 6
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- 238000012360 testing method Methods 0.000 description 6
- 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 description 5
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- ZXVDQAWXPDYSGO-UHFFFAOYSA-N 2-(1-benzylazepan-4-yl)-1h-imidazo[4,5-b]pyridine Chemical compound C1CCC(C=2NC3=CC=CN=C3N=2)CCN1CC1=CC=CC=C1 ZXVDQAWXPDYSGO-UHFFFAOYSA-N 0.000 description 4
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- 229910052794 bromium Inorganic materials 0.000 description 3
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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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—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)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99204441 | 1999-12-21 | ||
| PCT/EP2000/012858 WO2001046189A1 (en) | 1999-12-21 | 2000-12-14 | Substituted homopiperidinyl benzimidazole analogues as fundic relaxants |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20022977D0 NO20022977D0 (no) | 2002-06-20 |
| NO20022977L NO20022977L (no) | 2002-08-08 |
| NO322362B1 true NO322362B1 (no) | 2006-09-25 |
Family
ID=8241040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20022977A NO322362B1 (no) | 1999-12-21 | 2002-06-20 | Substituerte homopiperidinylbenzimidazolanaloger som fundiske relaksanter |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US7304052B2 (da) |
| EP (1) | EP1250337B1 (da) |
| JP (1) | JP4852210B2 (da) |
| KR (1) | KR100715351B1 (da) |
| CN (1) | CN100343251C (da) |
| AT (1) | ATE416174T1 (da) |
| AU (1) | AU781144B2 (da) |
| BG (1) | BG65784B1 (da) |
| BR (1) | BRPI0016638B8 (da) |
| CA (1) | CA2393158C (da) |
| CY (1) | CY1108844T1 (da) |
| CZ (1) | CZ299803B6 (da) |
| DE (1) | DE60041001D1 (da) |
| DK (1) | DK1250337T3 (da) |
| EA (1) | EA005851B1 (da) |
| EE (1) | EE05182B1 (da) |
| ES (1) | ES2317856T3 (da) |
| HK (1) | HK1053109B (da) |
| HR (1) | HRP20020518B1 (da) |
| HU (1) | HU229929B1 (da) |
| IL (2) | IL150310A0 (da) |
| MX (1) | MXPA02006346A (da) |
| MY (1) | MY127758A (da) |
| NO (1) | NO322362B1 (da) |
| NZ (1) | NZ518816A (da) |
| PL (1) | PL199678B1 (da) |
| PT (1) | PT1250337E (da) |
| SI (1) | SI1250337T1 (da) |
| SK (1) | SK287113B6 (da) |
| TW (1) | TWI225488B (da) |
| UA (1) | UA73963C2 (da) |
| WO (1) | WO2001046189A1 (da) |
| ZA (1) | ZA200204983B (da) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI225488B (en) | 1999-12-21 | 2004-12-21 | Janssen Pharmaceutica Nv | Derivatives of homopiperidinyl substituted benzimidazole analogues |
| JO2352B1 (en) * | 2000-06-22 | 2006-12-12 | جانسين فارماسيوتيكا ان. في | Compounds for the treatment of non-adaptation of the bottom of the uterus |
| JP2005532991A (ja) | 2002-01-10 | 2005-11-04 | ニューロジェン・コーポレーション | メラニン凝集ホルモン受容体リガンド：置換２−（４−ベンジル−ピペラジン−１−イルメチル）−及び２−（４−ベンジル−ジアゼパン−１−イルメチル）−１ｈ−ベンゾイミダゾールアナログ |
| CN100567270C (zh) * | 2004-02-19 | 2009-12-09 | 万有制药株式会社 | 磺酰胺衍生物 |
| EP2121683B1 (en) * | 2007-01-25 | 2011-08-31 | Janssen Pharmaceutica, N.V. | 2-piperazin-1-yl-3h-imidazo[4,5-b]pyridine derivatives |
| BR112012033117A2 (pt) | 2010-06-24 | 2016-11-22 | Gilead Sciences Inc | pirazolo[1,5-a]pirimidinas como agentes antivirais |
| US20130303782A1 (en) * | 2010-11-24 | 2013-11-14 | Sequent Scientific Limited | Process for preparation of albendazole |
| JP2014159375A (ja) * | 2011-06-15 | 2014-09-04 | Takeda Chem Ind Ltd | アゼパン化合物 |
| PT2794611T (pt) | 2011-12-22 | 2017-12-06 | Gilead Sciences Inc | Pirazolo[1,5-a]pirimidinas como agentes antivirais |
| HUE045727T2 (hu) | 2012-04-17 | 2021-12-28 | Gilead Sciences Inc | Vegyületek és eljárások vírusellenes kezeléshez |
| WO2015091584A1 (en) * | 2013-12-18 | 2015-06-25 | F. Hoffmann-La Roche Ag | Thiazolopyridine compounds, compositions and their use as tyk2 kinase inhibitors |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2060197C3 (de) * | 1970-12-08 | 1979-02-22 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 2-Aminobenzothiazol und dessen N-Alkylsubstitutionsprodukten |
| US4093726A (en) * | 1976-12-02 | 1978-06-06 | Abbott Laboratories | N-(2-benzimidazolyl)-piperazines |
| ES8101067A1 (es) * | 1978-08-25 | 1980-12-01 | Thomae Gmbh Dr K | Procedimiento para la preparacion de nuevos bencimidazoles sustituidos en posicion 5 o 6 con un anillo de piridazinona |
| JPS5879983A (ja) * | 1981-11-06 | 1983-05-13 | Kanebo Ltd | 新規なベンズイミダゾ−ル誘導体、その製造法およびその医薬組成物 |
| FR2528526A1 (fr) * | 1982-06-09 | 1983-12-16 | Sfr Sa Robinetterie | Butee se fixant dans un alesage d'un dispositif |
| DE3224512A1 (de) * | 1982-07-01 | 1984-01-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue imidazolderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| PH23995A (en) * | 1984-01-09 | 1990-02-09 | Janssen Pharmaceutica Nv | 4((bicycle heterocyclyl)-methyl and hetero)piperidines |
| DE3634066A1 (de) * | 1986-10-07 | 1988-04-21 | Boehringer Mannheim Gmbh | Neue 5-alkylbenzimidazole, verfahren zu ihrer herstellung sowie arzneimittel |
| JPH0260197A (ja) * | 1988-08-26 | 1990-02-28 | Nec Corp | パッケージ構造 |
| FR2674856B1 (fr) * | 1991-04-05 | 1993-07-30 | Esteve Labor Dr | Nouveaux antihistaminiques non sedatifs, derives de benzimidazole, leur procede de preparation et leur utilisation en tant que medicaments. |
| IL101851A (en) * | 1991-06-13 | 1996-05-14 | Janssen Pharmaceutica Nv | History 01 -) 4 - Pipridinyl - and Pipridinylidene (- Imidazo] A-1,2 [Pirolo, Thiano or Purano (] 3,2 [Azpin, their preparation and pharmaceutical preparations containing them and composition |
| DE4237656A1 (de) * | 1992-06-13 | 1993-12-16 | Merck Patent Gmbh | Benzimidazolderivate |
| WO1994001107A1 (en) * | 1992-07-08 | 1994-01-20 | Monsanto Company | Benzimidazoles for alleviating stomach ulcers in swine |
| ES2048109B1 (es) * | 1992-07-20 | 1994-12-16 | Espanola Prod Quimicos | Procedimiento de preparacion de nuevos derivados piperidicos del bencimidazol. |
| ES2172585T3 (es) * | 1994-05-31 | 2002-10-01 | Mitsui Chemicals Inc | Derivado de benzoimidazol. |
| FR2766822B1 (fr) * | 1997-07-30 | 2001-02-23 | Adir | Nouveaux derives de benzimidazole, de benzoxazole et de benzothiazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6150379A (en) * | 1997-11-26 | 2000-11-21 | Axys Pharmaceuticals, Inc. | Compounds and compositions as anticoagulants |
| TWI225488B (en) | 1999-12-21 | 2004-12-21 | Janssen Pharmaceutica Nv | Derivatives of homopiperidinyl substituted benzimidazole analogues |
-
2000
- 2000-12-11 TW TW089126315A patent/TWI225488B/zh not_active IP Right Cessation
- 2000-12-14 PL PL355442A patent/PL199678B1/pl unknown
- 2000-12-14 AU AU21673/01A patent/AU781144B2/en not_active Ceased
- 2000-12-14 JP JP2001547099A patent/JP4852210B2/ja not_active Expired - Fee Related
- 2000-12-14 NZ NZ518816A patent/NZ518816A/xx not_active IP Right Cessation
- 2000-12-14 WO PCT/EP2000/012858 patent/WO2001046189A1/en active IP Right Grant
- 2000-12-14 CZ CZ20022055A patent/CZ299803B6/cs not_active IP Right Cessation
- 2000-12-14 EE EEP200200326A patent/EE05182B1/xx not_active IP Right Cessation
- 2000-12-14 BR BRPI0016638A patent/BRPI0016638B8/pt not_active IP Right Cessation
- 2000-12-14 CA CA2393158A patent/CA2393158C/en not_active Expired - Fee Related
- 2000-12-14 DE DE60041001T patent/DE60041001D1/de not_active Expired - Lifetime
- 2000-12-14 UA UA2002065092A patent/UA73963C2/uk unknown
- 2000-12-14 IL IL15031000A patent/IL150310A0/xx unknown
- 2000-12-14 HU HU0203847A patent/HU229929B1/hu unknown
- 2000-12-14 EA EA200200700A patent/EA005851B1/ru not_active IP Right Cessation
- 2000-12-14 PT PT00985180T patent/PT1250337E/pt unknown
- 2000-12-14 EP EP00985180A patent/EP1250337B1/en not_active Expired - Lifetime
- 2000-12-14 SI SI200031019T patent/SI1250337T1/sl unknown
- 2000-12-14 MX MXPA02006346A patent/MXPA02006346A/es active IP Right Grant
- 2000-12-14 AT AT00985180T patent/ATE416174T1/de active
- 2000-12-14 KR KR1020027006004A patent/KR100715351B1/ko not_active IP Right Cessation
- 2000-12-14 SK SK854-2002A patent/SK287113B6/sk not_active IP Right Cessation
- 2000-12-14 ES ES00985180T patent/ES2317856T3/es not_active Expired - Lifetime
- 2000-12-14 US US10/169,011 patent/US7304052B2/en not_active Expired - Fee Related
- 2000-12-14 DK DK00985180T patent/DK1250337T3/da active
- 2000-12-14 CN CNB008174458A patent/CN100343251C/zh not_active Expired - Fee Related
- 2000-12-20 MY MYPI20006015A patent/MY127758A/en unknown
-
2002
- 2002-05-29 BG BG106749A patent/BG65784B1/bg unknown
- 2002-06-13 HR HR20020518A patent/HRP20020518B1/xx not_active IP Right Cessation
- 2002-06-19 IL IL150310A patent/IL150310A/en not_active IP Right Cessation
- 2002-06-20 NO NO20022977A patent/NO322362B1/no not_active IP Right Cessation
- 2002-06-20 ZA ZA200204983A patent/ZA200204983B/en unknown
-
2003
- 2003-07-23 HK HK03105325.2A patent/HK1053109B/zh not_active IP Right Cessation
-
2009
- 2009-03-03 CY CY20091100243T patent/CY1108844T1/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |