KR20090021346A - 트리메부틴 및 ｎ-데스메틸 트리메부틴 염 - Google Patents
트리메부틴 및 ｎ-데스메틸 트리메부틴 염Info
- Publication number
- KR20090021346A KR20090021346A KR1020087029794A KR20087029794A KR20090021346A KR 20090021346 A KR20090021346 A KR 20090021346A KR 1020087029794 A KR1020087029794 A KR 1020087029794A KR 20087029794 A KR20087029794 A KR 20087029794A KR 20090021346 A KR20090021346 A KR 20090021346A
- Authority
- KR
- South Korea
- Prior art keywords
- nitroargininate
- trimebutine
- compound
- thione
- desmethyltrimebutine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229960005345 trimebutine Drugs 0.000 title claims abstract description 42
- LORDFXWUHHSAQU-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid [2-(dimethylamino)-2-phenylbutyl] ester Chemical compound C=1C=CC=CC=1C(CC)(N(C)C)COC(=O)C1=CC(OC)=C(OC)C(OC)=C1 LORDFXWUHHSAQU-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 150000003839 salts Chemical class 0.000 title claims abstract description 31
- ZFPDLGDYDUPYEZ-UHFFFAOYSA-N [2-(methylamino)-2-phenylbutyl] 3,4,5-trimethoxybenzoate Chemical compound C=1C=CC=CC=1C(CC)(NC)COC(=O)C1=CC(OC)=C(OC)C(OC)=C1 ZFPDLGDYDUPYEZ-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 208000009935 visceral pain Diseases 0.000 claims abstract description 29
- 208000004998 Abdominal Pain Diseases 0.000 claims abstract description 17
- 208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 16
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims abstract description 14
- 201000006549 dyspepsia Diseases 0.000 claims abstract description 11
- 206010051153 Diabetic gastroparesis Diseases 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 38
- WRLUODMOTSXWIP-BYPYZUCNSA-N (2s)-5-(diaminomethylideneamino)-2-nitramidopentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)N[N+]([O-])=O WRLUODMOTSXWIP-BYPYZUCNSA-N 0.000 claims description 24
- -1 trimethoxy butyne p-hydroxy-benzamide Chemical compound 0.000 claims description 23
- WDPJBSOGQXMVEC-UHFFFAOYSA-N carbamothioyl benzoate Chemical compound NC(=S)OC(=O)C1=CC=CC=C1 WDPJBSOGQXMVEC-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- QXSAKPUBHTZHKW-UHFFFAOYSA-N 4-hydroxybenzamide Chemical compound NC(=O)C1=CC=C(O)C=C1 QXSAKPUBHTZHKW-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 3
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 2
- 235000018417 cysteine Nutrition 0.000 claims description 2
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- 206010033799 Paralysis Diseases 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-M argininate Chemical compound [O-]C(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-M 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- 239000000243 solution Substances 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 36
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- 239000000203 mixture Substances 0.000 description 23
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- 239000003981 vehicle Substances 0.000 description 17
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
- QCKWLHVPJKUAEI-UHFFFAOYSA-N ethyl 2-anilinoacetate;hydrochloride Chemical compound Cl.CCOC(=O)CNC1=CC=CC=C1 QCKWLHVPJKUAEI-UHFFFAOYSA-N 0.000 description 16
- 230000001149 cognitive effect Effects 0.000 description 15
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- 235000019441 ethanol Nutrition 0.000 description 13
- 238000011552 rat model Methods 0.000 description 13
- MRAUNPAHJZDYCK-BYPYZUCNSA-N L-nitroarginine Chemical compound OC(=O)[C@@H](N)CCCNC(=N)N[N+]([O-])=O MRAUNPAHJZDYCK-BYPYZUCNSA-N 0.000 description 11
- 241000700159 Rattus Species 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- GVEVKAIAOIRIAL-UHFFFAOYSA-N 4-carbamothioylbenzoic acid Chemical compound NC(=S)C1=CC=C(C(O)=O)C=C1 GVEVKAIAOIRIAL-UHFFFAOYSA-N 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- UMWBHGDTJNLDHJ-VWMHFEHESA-N (2S)-5-(diaminomethylideneamino)-2-nitramidopentanoic acid 4-hydroxybenzenecarbothioamide Chemical compound NC(=S)C1=CC=C(O)C=C1.NC(=N)NCCC[C@@H](C(O)=O)N[N+]([O-])=O UMWBHGDTJNLDHJ-VWMHFEHESA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 208000002193 Pain Diseases 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- FSRLGULMGJGKGI-BTJKTKAUSA-N Trimebutine maleate Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=CC=1C(CC)(N(C)C)COC(=O)C1=CC(OC)=C(OC)C(OC)=C1 FSRLGULMGJGKGI-BTJKTKAUSA-N 0.000 description 6
- 210000001072 colon Anatomy 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 210000001035 gastrointestinal tract Anatomy 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000009278 visceral effect Effects 0.000 description 6
- HRQGMPWJXQSTEH-UHFFFAOYSA-N 2-(methylamino)-2-phenylbutan-1-ol Chemical compound CCC(CO)(NC)C1=CC=CC=C1 HRQGMPWJXQSTEH-UHFFFAOYSA-N 0.000 description 5
- 230000006399 behavior Effects 0.000 description 5
- IWBBKLMHAILHAR-UHFFFAOYSA-N chembl402341 Chemical compound C1=CC(O)=CC=C1C1=CC(=S)SS1 IWBBKLMHAILHAR-UHFFFAOYSA-N 0.000 description 5
- PRQUMJAKVLLZHP-UHFFFAOYSA-N ethyl 2-(benzylideneamino)acetate Chemical compound CCOC(=O)CN=CC1=CC=CC=C1 PRQUMJAKVLLZHP-UHFFFAOYSA-N 0.000 description 5
- HVNIWFRPHRZUCM-UHFFFAOYSA-N ethyl 2-amino-2-phenylbutanoate;hydrochloride Chemical compound Cl.CCOC(=O)C(N)(CC)C1=CC=CC=C1 HVNIWFRPHRZUCM-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 4
- MXDJHSXVRYNXQJ-UHFFFAOYSA-N 2-(diaminomethylideneamino)-5-nitro-2-[[4-(5-sulfanylidenedithiol-3-yl)phenoxy]carbonylamino]pentanoic acid Chemical compound [N+](=O)([O-])CCCC(C(=O)O)(NC(=O)OC1=CC=C(C=C1)C=1SSC(C1)=S)NC(=N)N MXDJHSXVRYNXQJ-UHFFFAOYSA-N 0.000 description 4
- LKXJHOUMFBVYGX-UHFFFAOYSA-N 2-[(4-carbamothioylphenoxy)carbonylamino]-2-(diaminomethylideneamino)-5-nitropentanoic acid Chemical compound [N+](=O)([O-])CCCC(C(=O)O)(NC(=O)OC1=CC=C(C=C1)C(N)=S)NC(=N)N LKXJHOUMFBVYGX-UHFFFAOYSA-N 0.000 description 4
- FEGRFVVWVLMNIC-UHFFFAOYSA-N 2-[[amino-[2-(2-amino-3-sulfanylpropanoyl)hydrazinyl]methylidene]amino]-5-nitropentanoic acid Chemical compound SCC(N)C(=O)NNC(N)=NC(C(O)=O)CCC[N+]([O-])=O FEGRFVVWVLMNIC-UHFFFAOYSA-N 0.000 description 4
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 210000001015 abdomen Anatomy 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- JLEZVTIYNCKTNH-UHFFFAOYSA-N ethyl 2-amino-2-phenylbutanoate Chemical compound CCOC(=O)C(N)(CC)C1=CC=CC=C1 JLEZVTIYNCKTNH-UHFFFAOYSA-N 0.000 description 4
- GOFCZGZYFDCXFH-UHFFFAOYSA-N ethyl 2-formamido-2-phenylbutanoate Chemical compound CCOC(=O)C(CC)(NC=O)C1=CC=CC=C1 GOFCZGZYFDCXFH-UHFFFAOYSA-N 0.000 description 4
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- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/14—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/30—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to nitro or nitroso groups
- C07C279/32—N-nitroguanidines
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/20—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/48—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80406706P | 2006-06-06 | 2006-06-06 | |
| US60/804,067 | 2006-06-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20090021346A true KR20090021346A (ko) | 2009-03-03 |
Family
ID=38801016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087029794A Withdrawn KR20090021346A (ko) | 2006-06-06 | 2007-06-06 | 트리메부틴 및 ｎ-데스메틸 트리메부틴 염 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US20110144188A1 (https=) |
| EP (1) | EP2024323B1 (https=) |
| JP (1) | JP5421098B2 (https=) |
| KR (1) | KR20090021346A (https=) |
| CN (1) | CN101489986A (https=) |
| AU (1) | AU2007257174B2 (https=) |
| BR (1) | BRPI0712417A2 (https=) |
| CA (1) | CA2653869A1 (https=) |
| RU (1) | RU2008152751A (https=) |
| WO (1) | WO2007140611A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7741359B2 (en) * | 2005-05-27 | 2010-06-22 | Antibe Therapeutics Inc. | Hydrogen sulfide derivatives of non-steroidal anti-inflammatory drugs |
| US7932286B2 (en) * | 2007-07-31 | 2011-04-26 | Martin Francois | Method for treating colonic viscerosensitivity and spasticity |
| FR2927076B1 (fr) * | 2008-01-31 | 2010-03-26 | Oroxcell | Derives de 2-amino-2-phenyl-alkanol, leur preparation et les compositions pharmaceutiques qui les contiennent |
| EP2744487B1 (en) | 2011-08-15 | 2016-10-05 | Research Foundation Of The City University Of New York | No- and h2s- releasing compounds |
| IN2014DN08379A (https=) * | 2012-03-12 | 2015-05-08 | Gicare Pharma Inc | |
| WO2016044951A1 (en) * | 2014-09-25 | 2016-03-31 | The Hospital For Sick Children | Compositions and methods for enhancing hair growth, promoting skin regeneration, and wound healing |
| RU2752086C1 (ru) | 2020-04-27 | 2021-07-22 | Общество С Ограниченной Ответственностью "Валента-Интеллект" | Новое соединение [2-(диметиламино)-2-фенилбутил]-3,4,5-триметоксибензоата 4-метил-2н-хромен-2-он-7-илсульфат и его применение |
| CN114916547B (zh) * | 2021-12-06 | 2024-11-15 | 南京天秾生物技术有限公司 | 2,6-二氨基-3-甲基己酸作为植物免疫诱抗剂的应用 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2460919A1 (fr) * | 1979-07-11 | 1981-01-30 | Prod Synthese Ste Indle | Amino-ethers oxydes, leur procede de preparation et leur application en therapeutique |
| JPS57500432A (https=) * | 1980-03-20 | 1982-03-11 | ||
| US4412992A (en) * | 1980-07-21 | 1983-11-01 | Biorex Laboratories Limited | 2-Hydroxy-5-phenylazobenzoic acid derivatives and method of treating ulcerative colitis therewith |
| US4440763A (en) * | 1981-03-18 | 1984-04-03 | Block Drug Company, Inc. | Use of 4-aminosalicyclic acid as an anti-inflammatory agent |
| ZA825384B (en) * | 1981-07-31 | 1983-05-25 | Tillott J B Ltd | Orally administrable pharmaceutical compositions |
| US4751221A (en) * | 1985-10-18 | 1988-06-14 | Sloan-Kettering Institute For Cancer Research | 2-fluoro-arabinofuranosyl purine nucleosides |
| US5245080A (en) * | 1989-02-20 | 1993-09-14 | Jouveinal Sa | (+)-1-[(3,4,5-trimethoxy)-benzyloxymethyl]-1-phenyl-N,N-dimethyl-N-propylamine, process for preparing it and its therapeutical use |
| US5811547A (en) * | 1992-10-14 | 1998-09-22 | Nippon Shinyaju Co., Ltd. | Method for inducing crystalline state transition in medicinal substance |
| CA2204747C (en) | 1995-09-08 | 2009-05-05 | Elena Carceller | New azo derivatives of 5-aminosalicylic acid |
| SE9700934D0 (sv) * | 1997-03-14 | 1997-03-14 | Astra Ab | New formulation |
| WO1998048826A1 (en) * | 1997-04-30 | 1998-11-05 | Northwestern University | Inhibition of nitric oxide synthase by amino acids and dipeptides |
| SV2001000242A (es) * | 1999-12-23 | 2001-10-25 | Warner Lambert Co | Combinacion de trimebutina con un analgesico derivado del opio |
| EP1110549A1 (en) * | 1999-12-23 | 2001-06-27 | Warner-Lambert Company | Use of trimebutine for treating pain |
| EP1296943A1 (fr) * | 2000-05-05 | 2003-04-02 | Societe De Conseils De Recherches Et D'applications Scientifiques S.A. (S.C.R.A.S.) | Derives d'aminoacides et leur application a titre de medicaments |
| US6602915B2 (en) * | 2000-07-27 | 2003-08-05 | Rutgers, The State University Of New Jersey | Therapeutic azo-compounds for drug delivery |
| AU2001285489A1 (en) * | 2000-08-29 | 2002-03-13 | Nobex Corporation | 5-ASA derivatives having anti-inflammatory and antibiotic activity and methods of treating diseases therewith |
| US6986901B2 (en) * | 2002-07-15 | 2006-01-17 | Warner-Lambert Company Llc | Gastrointestinal compositions |
| JP2005533101A (ja) * | 2002-07-10 | 2005-11-04 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | アロステリック阻害剤又はマトリックス金属タンパク質分解酵素−１３の、セレコキシブでもバルデコキシブでもないシクロオキシゲナーゼ−２の選択的阻害剤との組合せ物 |
| US20040213842A1 (en) * | 2003-01-30 | 2004-10-28 | Dynogen Pharmaceuticals, Inc. | Methods of treating gastrointestinal tract disorders using sodium channel modulators |
| EP1645288A1 (en) | 2004-10-07 | 2006-04-12 | CTG Pharma S.r.l. | New nuclear transcription factors regulators |
-
2007
- 2007-06-06 US US12/303,082 patent/US20110144188A1/en not_active Abandoned
- 2007-06-06 US US11/759,154 patent/US7666907B2/en not_active Expired - Fee Related
- 2007-06-06 BR BRPI0712417-1A patent/BRPI0712417A2/pt not_active IP Right Cessation
- 2007-06-06 AU AU2007257174A patent/AU2007257174B2/en not_active Ceased
- 2007-06-06 EP EP07719924A patent/EP2024323B1/en not_active Not-in-force
- 2007-06-06 WO PCT/CA2007/001008 patent/WO2007140611A1/en not_active Ceased
- 2007-06-06 CA CA002653869A patent/CA2653869A1/en not_active Abandoned
- 2007-06-06 JP JP2009513524A patent/JP5421098B2/ja not_active Expired - Fee Related
- 2007-06-06 RU RU2008152751/04A patent/RU2008152751A/ru unknown
- 2007-06-06 CN CNA2007800264544A patent/CN101489986A/zh active Pending
- 2007-06-06 KR KR1020087029794A patent/KR20090021346A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US20070275905A1 (en) | 2007-11-29 |
| EP2024323B1 (en) | 2013-03-27 |
| EP2024323A1 (en) | 2009-02-18 |
| EP2024323A4 (en) | 2010-07-28 |
| WO2007140611A1 (en) | 2007-12-13 |
| AU2007257174B2 (en) | 2012-07-12 |
| BRPI0712417A2 (pt) | 2012-09-04 |
| JP2009539777A (ja) | 2009-11-19 |
| RU2008152751A (ru) | 2010-07-20 |
| US20110144188A1 (en) | 2011-06-16 |
| JP5421098B2 (ja) | 2014-02-19 |
| AU2007257174A1 (en) | 2007-12-13 |
| CN101489986A (zh) | 2009-07-22 |
| US7666907B2 (en) | 2010-02-23 |
| CA2653869A1 (en) | 2007-12-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20081205 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |