NO331272B1 - Syreaddisjonssalter av polysure basiske forbindelser samt fremgangsmate for fremstilling derav - Google Patents
Syreaddisjonssalter av polysure basiske forbindelser samt fremgangsmate for fremstilling derav Download PDFInfo
- Publication number
- NO331272B1 NO331272B1 NO20054100A NO20054100A NO331272B1 NO 331272 B1 NO331272 B1 NO 331272B1 NO 20054100 A NO20054100 A NO 20054100A NO 20054100 A NO20054100 A NO 20054100A NO 331272 B1 NO331272 B1 NO 331272B1
- Authority
- NO
- Norway
- Prior art keywords
- acid
- ylthio
- ethyl
- pyridyl
- methyl
- Prior art date
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- 239000002253 acid Substances 0.000 title claims abstract description 107
- 150000003839 salts Chemical class 0.000 title claims abstract description 78
- 238000000034 method Methods 0.000 title claims abstract description 24
- 150000007514 bases Chemical class 0.000 title abstract description 19
- 238000002360 preparation method Methods 0.000 title description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 109
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 66
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 47
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 42
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- 239000013078 crystal Substances 0.000 claims description 27
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 26
- 150000004885 piperazines Chemical class 0.000 claims description 25
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 24
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- VGGMTOYKEDKFLN-UHFFFAOYSA-N 2-[4-[2-(1h-benzimidazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[6-methyl-2,4-bis(methylsulfanyl)pyridin-3-yl]acetamide Chemical group CSC1=CC(C)=NC(SC)=C1NC(=O)CN1CCN(CCSC=2NC3=CC=CC=C3N=2)CC1 VGGMTOYKEDKFLN-UHFFFAOYSA-N 0.000 claims description 15
- FIESYXUDBWMLRP-UHFFFAOYSA-N 2-[4-[2-(1h-benzimidazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[6-methyl-2,4-bis(methylsulfanyl)pyridin-3-yl]acetamide;hydrochloride Chemical group Cl.CSC1=CC(C)=NC(SC)=C1NC(=O)CN1CCN(CCSC=2NC3=CC=CC=C3N=2)CC1 FIESYXUDBWMLRP-UHFFFAOYSA-N 0.000 claims description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- -1 methylthio, trifluoroethoxy Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- DYXZQYKQRNTJHR-UHFFFAOYSA-N 2-[4-[2-(1,3-benzoxazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[2-(2-methoxyethoxy)-6-methyl-4-(2,2,2-trifluoroethoxy)pyridin-3-yl]acetamide Chemical compound COCCOC1=NC(C)=CC(OCC(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2OC3=CC=CC=C3N=2)CC1 DYXZQYKQRNTJHR-UHFFFAOYSA-N 0.000 claims description 6
- SZLMBHBRSADVAR-UHFFFAOYSA-N 2-[4-[2-[(5,6-difluoro-1h-benzimidazol-2-yl)sulfanyl]ethyl]piperazin-1-yl]-n-[6-methyl-2,4-bis(2,2,2-trifluoroethoxy)pyridin-3-yl]acetamide Chemical compound FC(F)(F)COC1=NC(C)=CC(OCC(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2NC3=CC(F)=C(F)C=C3N=2)CC1 SZLMBHBRSADVAR-UHFFFAOYSA-N 0.000 claims description 6
- CMISTLFCNNXRRS-UHFFFAOYSA-N 2-[4-[2-[(5,6-difluoro-1h-benzimidazol-2-yl)sulfanyl]ethyl]piperazin-1-yl]-n-[6-methyl-2,4-bis(2,2,2-trifluoroethoxy)pyridin-3-yl]acetamide;hydrochloride Chemical group Cl.FC(F)(F)COC1=NC(C)=CC(OCC(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2NC3=CC(F)=C(F)C=C3N=2)CC1 CMISTLFCNNXRRS-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- ZPROUZXZOZJFTI-UHFFFAOYSA-N n-[6-methyl-2,4-bis(methylsulfanyl)pyridin-3-yl]-2-[4-[2-[[5-(trifluoromethyl)-1,3-benzoxazol-2-yl]sulfanyl]ethyl]piperazin-1-yl]acetamide Chemical compound CSC1=CC(C)=NC(SC)=C1NC(=O)CN1CCN(CCSC=2OC3=CC=C(C=C3N=2)C(F)(F)F)CC1 ZPROUZXZOZJFTI-UHFFFAOYSA-N 0.000 claims description 6
- OATIVIRLRZWRAT-UHFFFAOYSA-N n-[6-methyl-2,4-bis(methylsulfanyl)pyridin-3-yl]-2-[4-[2-[[5-(trifluoromethyl)-1,3-benzoxazol-2-yl]sulfanyl]ethyl]piperazin-1-yl]acetamide;hydrochloride Chemical compound Cl.CSC1=CC(C)=NC(SC)=C1NC(=O)CN1CCN(CCSC=2OC3=CC=C(C=C3N=2)C(F)(F)F)CC1 OATIVIRLRZWRAT-UHFFFAOYSA-N 0.000 claims description 6
- LIFBIPOMKGMSFM-UHFFFAOYSA-N 2-[4-[2-(1,3-benzothiazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[2,6-dimethyl-4-(trifluoromethyl)pyridin-3-yl]acetamide Chemical compound CC1=NC(C)=CC(C(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2SC3=CC=CC=C3N=2)CC1 LIFBIPOMKGMSFM-UHFFFAOYSA-N 0.000 claims description 5
- SRBPYSVRCCDDNI-UHFFFAOYSA-N 2-[4-[2-(1,3-benzothiazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[2,6-dimethyl-4-(trifluoromethyl)pyridin-3-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.CC1=NC(C)=CC(C(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2SC3=CC=CC=C3N=2)CC1 SRBPYSVRCCDDNI-UHFFFAOYSA-N 0.000 claims description 5
- ZXWDDGWHGFZRRF-UHFFFAOYSA-N 2-[4-[2-(1h-benzimidazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[6-methyl-2,4-bis(2,2,2-trifluoroethoxy)pyridin-3-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.FC(F)(F)COC1=NC(C)=CC(OCC(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2NC3=CC=CC=C3N=2)CC1 ZXWDDGWHGFZRRF-UHFFFAOYSA-N 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
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- ODYLAJPEWLKGCS-UHFFFAOYSA-N 2-[4-[2-(1,3-benzoxazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[2-(2-methoxyethoxy)-6-methyl-4-(2,2,2-trifluoroethoxy)pyridin-3-yl]acetamide;hydrochloride Chemical compound Cl.COCCOC1=NC(C)=CC(OCC(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2OC3=CC=CC=C3N=2)CC1 ODYLAJPEWLKGCS-UHFFFAOYSA-N 0.000 claims description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 4
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
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- 239000001263 FEMA 3042 Substances 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- 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
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003052700 | 2003-02-28 | ||
| PCT/JP2004/002375 WO2004076441A1 (ja) | 2003-02-28 | 2004-02-27 | 多酸性塩基化合物の酸付加塩の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20054100D0 NO20054100D0 (no) | 2005-09-02 |
| NO20054100L NO20054100L (no) | 2005-09-22 |
| NO331272B1 true NO331272B1 (no) | 2011-11-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20054100A NO331272B1 (no) | 2003-02-28 | 2005-09-02 | Syreaddisjonssalter av polysure basiske forbindelser samt fremgangsmate for fremstilling derav |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7750150B2 (pt) |
| EP (1) | EP1598346B1 (pt) |
| JP (2) | JP4594863B2 (pt) |
| KR (1) | KR101106127B1 (pt) |
| CN (2) | CN102702171B (pt) |
| AT (1) | ATE554083T1 (pt) |
| AU (1) | AU2004215523B2 (pt) |
| BR (1) | BRPI0407908A (pt) |
| CA (1) | CA2516822C (pt) |
| DK (1) | DK1598346T3 (pt) |
| EA (1) | EA009045B1 (pt) |
| ES (1) | ES2384517T3 (pt) |
| IL (1) | IL170093A (pt) |
| IS (1) | IS7978A (pt) |
| MX (1) | MXPA05009129A (pt) |
| MY (1) | MY140618A (pt) |
| NO (1) | NO331272B1 (pt) |
| NZ (1) | NZ541716A (pt) |
| PL (1) | PL378292A1 (pt) |
| TW (2) | TWI374136B (pt) |
| WO (1) | WO2004076441A1 (pt) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY140849A (en) * | 2003-07-07 | 2010-01-29 | Kowa Co | 2, 4-bis (trifluoroethoxy) pyridine compound and drug containing the compound |
| CA2535920C (en) | 2003-08-29 | 2009-06-23 | Kowa Co., Ltd. | Method of stabilizing lipid-rich plaque and method of preventing rupture thereof |
| TW200619204A (en) * | 2004-12-10 | 2006-06-16 | Kowa Co | Method for reduction, stabilization and prevention of rupture of lipid rich plaque |
| BRPI0614974A2 (pt) | 2005-08-30 | 2010-12-14 | Asahi Kasei Pharma Corp | composto, medicamento, inibidor da fosforilaÇço da cadeia leve regulatària da miosina, inibidor da via rho/rho quinase, e, mÉtodo para tratamento terapÊutico e/ou profilÁtico de glaucoma |
| US8415372B2 (en) * | 2007-02-27 | 2013-04-09 | Asahi Kasei Pharma Corporation | Sulfonamide compound |
| EP2130828A4 (en) * | 2007-02-28 | 2010-12-29 | Asahi Kasei Pharma Corp | sulfonamide |
| JP5234825B2 (ja) * | 2007-07-02 | 2013-07-10 | 旭化成ファーマ株式会社 | スルホンアミド化合物及びその結晶 |
| US9273209B2 (en) * | 2007-11-30 | 2016-03-01 | Braggone Oy | Siloxane polymer compositions |
| US20120289517A1 (en) * | 2009-12-29 | 2012-11-15 | Kowa Co., Ltd. | Solid pharmaceutical composition for oral administration |
| US20130035344A1 (en) * | 2009-12-29 | 2013-02-07 | Kowa Co., Ltd. | Pharmaceutical composition for oral administration |
| CA2798735A1 (en) * | 2010-05-19 | 2011-11-24 | Haruki Shibata | Prophylactic and/or therapeutic agent for non-alcoholic steatohepatitis |
| WO2016205141A1 (en) * | 2015-06-17 | 2016-12-22 | Gilead Sciences, Inc. | Co-crystals, salts and solid forms of tenofovir alafenamide |
| WO2018092765A1 (ja) * | 2016-11-15 | 2018-05-24 | 学校法人同志社 | 経鼻投与用医薬組成物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL112152A (en) * | 1994-12-26 | 2000-11-21 | Identa Ltd | Process and test kit for cocaine detection |
| EP0987254B1 (en) | 1997-05-26 | 2004-12-22 | Kowa Co., Ltd. | Novel cyclic diamine compounds and medicine containing the same |
| US6969711B2 (en) * | 1997-05-26 | 2005-11-29 | Kowa Company, Ltd. | Cyclic diamine compounds and medicine containing the same |
| GB9826180D0 (en) * | 1998-11-30 | 1999-01-20 | Smithkline Beecham Plc | Novel process |
| US20060165605A1 (en) * | 2001-12-28 | 2006-07-27 | Ye-Mon Chen | Process to regenerate fcc spent catalyst |
| JP4745666B2 (ja) * | 2002-12-12 | 2011-08-10 | 興和株式会社 | ヒドロキシアルキル環状ジアミン化合物 |
| MY140849A (en) * | 2003-07-07 | 2010-01-29 | Kowa Co | 2, 4-bis (trifluoroethoxy) pyridine compound and drug containing the compound |
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2004
- 2004-02-25 MY MYPI20040608A patent/MY140618A/en unknown
- 2004-02-27 WO PCT/JP2004/002375 patent/WO2004076441A1/ja active Search and Examination
- 2004-02-27 AT AT04715495T patent/ATE554083T1/de active
- 2004-02-27 DK DK04715495.0T patent/DK1598346T3/da active
- 2004-02-27 PL PL378292A patent/PL378292A1/pl not_active IP Right Cessation
- 2004-02-27 CN CN201210189482.0A patent/CN102702171B/zh not_active Expired - Fee Related
- 2004-02-27 MX MXPA05009129A patent/MXPA05009129A/es active IP Right Grant
- 2004-02-27 TW TW100135167A patent/TWI374136B/zh not_active IP Right Cessation
- 2004-02-27 NZ NZ541716A patent/NZ541716A/en not_active IP Right Cessation
- 2004-02-27 JP JP2005502951A patent/JP4594863B2/ja not_active Expired - Fee Related
- 2004-02-27 ES ES04715495T patent/ES2384517T3/es not_active Expired - Lifetime
- 2004-02-27 KR KR1020057015048A patent/KR101106127B1/ko not_active IP Right Cessation
- 2004-02-27 TW TW093105174A patent/TWI355384B/zh not_active IP Right Cessation
- 2004-02-27 CN CN2004800052621A patent/CN1753886B/zh not_active Expired - Fee Related
- 2004-02-27 US US10/545,200 patent/US7750150B2/en not_active Expired - Fee Related
- 2004-02-27 EP EP04715495A patent/EP1598346B1/en not_active Expired - Lifetime
- 2004-02-27 CA CA2516822A patent/CA2516822C/en not_active Expired - Fee Related
- 2004-02-27 BR BRPI0407908-6A patent/BRPI0407908A/pt not_active Application Discontinuation
- 2004-02-27 AU AU2004215523A patent/AU2004215523B2/en not_active Ceased
- 2004-02-27 EA EA200501379A patent/EA009045B1/ru not_active IP Right Cessation
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2005
- 2005-08-04 IL IL170093A patent/IL170093A/en not_active IP Right Cessation
- 2005-08-12 IS IS7978A patent/IS7978A/is unknown
- 2005-09-02 NO NO20054100A patent/NO331272B1/no not_active IP Right Cessation
-
2010
- 2010-04-16 US US12/762,111 patent/US8518936B2/en not_active Expired - Fee Related
- 2010-07-15 JP JP2010160354A patent/JP5180998B2/ja not_active Expired - Fee Related
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