NZ546111A - Crystal of sulfonamide-containing indole compound and process for producing the same - Google Patents
Crystal of sulfonamide-containing indole compound and process for producing the sameInfo
- Publication number
- NZ546111A NZ546111A NZ546111A NZ54611104A NZ546111A NZ 546111 A NZ546111 A NZ 546111A NZ 546111 A NZ546111 A NZ 546111A NZ 54611104 A NZ54611104 A NZ 54611104A NZ 546111 A NZ546111 A NZ 546111A
- Authority
- NZ
- New Zealand
- Prior art keywords
- cyano
- methyl
- indol
- cyanobenzenesulfonamide
- crystalline form
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 44
- 230000008569 process Effects 0.000 title claims abstract description 25
- 239000013078 crystal Substances 0.000 title description 181
- -1 indole compound Chemical class 0.000 title description 13
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title description 3
- 229940124530 sulfonamide Drugs 0.000 title description 3
- 150000003456 sulfonamides Chemical class 0.000 title description 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 32
- LWGUASZLXHYWIV-UHFFFAOYSA-N 3-cyano-n-(3-cyano-4-methyl-1h-indol-7-yl)benzenesulfonamide Chemical compound C1=2NC=C(C#N)C=2C(C)=CC=C1NS(=O)(=O)C1=CC=CC(C#N)=C1 LWGUASZLXHYWIV-UHFFFAOYSA-N 0.000 claims abstract description 3
- XKJMSWSCNHVIQW-UHFFFAOYSA-N 3-cyano-n-(3-cyano-4-methyl-1h-indol-7-yl)benzenesulfonamide;hydrate Chemical compound O.C1=2NC=C(C#N)C=2C(C)=CC=C1NS(=O)(=O)C1=CC=CC(C#N)=C1 XKJMSWSCNHVIQW-UHFFFAOYSA-N 0.000 claims abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 66
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- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 22
- 238000002425 crystallisation Methods 0.000 claims description 17
- 238000000862 absorption spectrum Methods 0.000 claims description 16
- 238000004922 13C solid-state nuclear magnetic resonance spectroscopy Methods 0.000 claims description 15
- 230000008025 crystallization Effects 0.000 claims description 15
- 239000000843 powder Substances 0.000 claims description 14
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 11
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 claims description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
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- 239000003655 absorption accelerator Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000305 astragalus gummifer gum Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
- 239000001354 calcium citrate Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000005384 cross polarization magic-angle spinning Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003410 keratolytic agent Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229940073665 octyldodecyl myristate Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003318953 | 2003-09-10 | ||
| PCT/JP2004/012649 WO2005026118A1 (ja) | 2003-09-10 | 2004-09-01 | スルホンアミド含有インドール化合物の結晶およびその製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ546111A true NZ546111A (en) | 2008-11-28 |
Family
ID=34308544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ546111A NZ546111A (en) | 2003-09-10 | 2004-09-01 | Crystal of sulfonamide-containing indole compound and process for producing the same |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US7754894B2 (https=) |
| EP (1) | EP1666463B1 (https=) |
| JP (1) | JP4435090B2 (https=) |
| KR (1) | KR20060120644A (https=) |
| CN (2) | CN101165049A (https=) |
| AT (1) | ATE486849T1 (https=) |
| AU (1) | AU2004272400B2 (https=) |
| BR (1) | BRPI0414314A (https=) |
| CA (1) | CA2536995C (https=) |
| CY (1) | CY1110975T1 (https=) |
| DE (1) | DE602004029907D1 (https=) |
| DK (1) | DK1666463T3 (https=) |
| ES (1) | ES2354286T3 (https=) |
| HR (1) | HRP20100631T1 (https=) |
| IL (2) | IL174059A0 (https=) |
| MX (1) | MXPA06002732A (https=) |
| NO (1) | NO335256B1 (https=) |
| NZ (1) | NZ546111A (https=) |
| PL (1) | PL1666463T3 (https=) |
| PT (1) | PT1666463E (https=) |
| RU (1) | RU2336269C2 (https=) |
| SI (1) | SI1666463T1 (https=) |
| TW (1) | TW200514770A (https=) |
| WO (1) | WO2005026118A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1666463T3 (da) * | 2003-09-10 | 2010-12-20 | Eisai R&D Man Co Ltd | Krystal af sulfonamidholdig indolforbindelse og fremgangsmåde til fremstilling deraf |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3868534B2 (ja) | 1996-05-24 | 2007-01-17 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | スルホンアミド誘導体の製造法および中間体 |
| JP2000247949A (ja) | 1999-02-26 | 2000-09-12 | Eisai Co Ltd | スルホンアミド含有インドール化合物 |
| WO2001056607A1 (en) * | 2000-02-03 | 2001-08-09 | Eisai Co., Ltd. | Integrin expression inhibitors |
| TWI283575B (en) * | 2000-10-31 | 2007-07-11 | Eisai Co Ltd | Medicinal compositions for concomitant use as anticancer agent |
| DK1666463T3 (da) * | 2003-09-10 | 2010-12-20 | Eisai R&D Man Co Ltd | Krystal af sulfonamidholdig indolforbindelse og fremgangsmåde til fremstilling deraf |
-
2004
- 2004-09-01 DK DK04772605.4T patent/DK1666463T3/da active
- 2004-09-01 ES ES04772605T patent/ES2354286T3/es not_active Expired - Lifetime
- 2004-09-01 RU RU2006111454/04A patent/RU2336269C2/ru not_active IP Right Cessation
- 2004-09-01 KR KR1020067004877A patent/KR20060120644A/ko not_active Ceased
- 2004-09-01 MX MXPA06002732A patent/MXPA06002732A/es active IP Right Grant
- 2004-09-01 CN CNA2007101667949A patent/CN101165049A/zh active Pending
- 2004-09-01 WO PCT/JP2004/012649 patent/WO2005026118A1/ja not_active Ceased
- 2004-09-01 PT PT04772605T patent/PT1666463E/pt unknown
- 2004-09-01 CA CA2536995A patent/CA2536995C/en not_active Expired - Fee Related
- 2004-09-01 BR BRPI0414314-0A patent/BRPI0414314A/pt not_active IP Right Cessation
- 2004-09-01 CN CNB2004800260696A patent/CN100406440C/zh not_active Expired - Fee Related
- 2004-09-01 NZ NZ546111A patent/NZ546111A/en not_active IP Right Cessation
- 2004-09-01 AU AU2004272400A patent/AU2004272400B2/en not_active Ceased
- 2004-09-01 DE DE602004029907T patent/DE602004029907D1/de not_active Expired - Lifetime
- 2004-09-01 US US10/571,279 patent/US7754894B2/en not_active Expired - Lifetime
- 2004-09-01 PL PL04772605T patent/PL1666463T3/pl unknown
- 2004-09-01 HR HR20100631T patent/HRP20100631T1/hr unknown
- 2004-09-01 JP JP2005513843A patent/JP4435090B2/ja not_active Expired - Fee Related
- 2004-09-01 EP EP04772605A patent/EP1666463B1/en not_active Expired - Lifetime
- 2004-09-01 SI SI200431578T patent/SI1666463T1/sl unknown
- 2004-09-01 AT AT04772605T patent/ATE486849T1/de active
- 2004-09-06 TW TW093126889A patent/TW200514770A/zh not_active IP Right Cessation
-
2006
- 2006-03-02 IL IL174059A patent/IL174059A0/en not_active IP Right Cessation
- 2006-04-05 NO NO20061545A patent/NO335256B1/no not_active IP Right Cessation
-
2009
- 2009-01-18 IL IL196569A patent/IL196569A0/en unknown
- 2009-06-09 US US12/480,959 patent/US20090247768A1/en not_active Abandoned
-
2010
- 2010-12-10 CY CY20101101136T patent/CY1110975T1/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ASS | Change of ownership |
Owner name: EISAI RANDD MANAGEMENT CO., JP Free format text: OLD OWNER(S): EISAI CO., LTD. |
|
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 3 YEARS UNTIL 01 SEP 2017 BY DENNEMEYER + CO Effective date: 20140801 |
|
| LAPS | Patent lapsed |