CN103739531B - 新型氨基酸衍生物、其制备方法和治疗用途 - Google Patents
新型氨基酸衍生物、其制备方法和治疗用途 Download PDFInfo
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- CN103739531B CN103739531B CN201310736987.9A CN201310736987A CN103739531B CN 103739531 B CN103739531 B CN 103739531B CN 201310736987 A CN201310736987 A CN 201310736987A CN 103739531 B CN103739531 B CN 103739531B
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003214 pyranose derivatives Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 235000008790 seltzer Nutrition 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000020341 sensory perception of pain Effects 0.000 description 1
- 230000036259 sexual stimuli Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000010572 single replacement reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
- 229960001052 streptozocin Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- SJMDMGHPMLKLHQ-UHFFFAOYSA-N tert-butyl 2-aminoacetate Chemical compound CC(C)(C)OC(=O)CN SJMDMGHPMLKLHQ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 210000002303 tibia Anatomy 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C323/64—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 sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
- C07C323/65—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 sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0853092A FR2931151A1 (fr) | 2008-05-13 | 2008-05-13 | Nouveaux derives d'amino-acides, leur procede de preparation et leur utilisation therapeutique |
| FR0853092 | 2008-05-13 | ||
| CN200980116831.2A CN102026966B (zh) | 2008-05-13 | 2009-05-13 | 新型氨基酸衍生物、其制备方法和治疗用途 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980116831.2A Division CN102026966B (zh) | 2008-05-13 | 2009-05-13 | 新型氨基酸衍生物、其制备方法和治疗用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103739531A CN103739531A (zh) | 2014-04-23 |
| CN103739531B true CN103739531B (zh) | 2016-09-14 |
Family
ID=40225670
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310736987.9A Active CN103739531B (zh) | 2008-05-13 | 2009-05-13 | 新型氨基酸衍生物、其制备方法和治疗用途 |
| CN200980116831.2A Active CN102026966B (zh) | 2008-05-13 | 2009-05-13 | 新型氨基酸衍生物、其制备方法和治疗用途 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980116831.2A Active CN102026966B (zh) | 2008-05-13 | 2009-05-13 | 新型氨基酸衍生物、其制备方法和治疗用途 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8466309B2 (https=) |
| EP (1) | EP2297095B9 (https=) |
| JP (1) | JP5642664B2 (https=) |
| KR (1) | KR20110008325A (https=) |
| CN (2) | CN103739531B (https=) |
| AT (1) | ATE555084T1 (https=) |
| AU (1) | AU2009248056A1 (https=) |
| BR (1) | BRPI0912398A2 (https=) |
| CA (1) | CA2722840C (https=) |
| EA (1) | EA201071272A1 (https=) |
| FR (1) | FR2931151A1 (https=) |
| IL (1) | IL209214A (https=) |
| MX (1) | MX2010012273A (https=) |
| NZ (1) | NZ588955A (https=) |
| WO (1) | WO2009138436A1 (https=) |
| ZA (1) | ZA201008029B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2934267B1 (fr) * | 2008-07-23 | 2010-08-13 | Pharmaleads | Derives aminophosphiniques utiles dans le traitement de la douleur |
| FR2997080B1 (fr) * | 2012-10-23 | 2015-11-27 | Pharmaleads | Inhibiteurs de neprilysine |
| FR2997081B1 (fr) | 2012-10-23 | 2015-11-27 | Pharmaleads | Inhibiteurs mixtes de l'aminopeptidase n et de la neprilysine |
| TWI712582B (zh) * | 2015-10-14 | 2020-12-11 | 法商領先藥物公司 | 用來製備(5s,10s)-10-苄基-16-甲基-11,14,18-三側氧基-15,17,19-三氧雜-2,7,8-三噻基-12-氮二十一烷基-5-銨基(e)-3-羧基丙烯酸鹽的工業方法 |
| FR3077201B1 (fr) * | 2018-01-26 | 2020-01-17 | Pharmaleads | Derives aminoacides contenant un groupement disulfanyle sous forme d'un inhibiteur de nep et d'apn pour la prevention et le traitement des douleurs relatives au nerf trijumeau |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4426391A (en) * | 1982-09-15 | 1984-01-17 | Merck & Co., Inc. | [(Alkoxycarbonyl)oxy]alkyl esters of methyldopa |
| EP1178034A1 (en) * | 2000-08-01 | 2002-02-06 | Warner-Lambert Company | Alkyl amino acid derivatives useful as pharmaceutical agents |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2480747A1 (fr) | 1980-04-17 | 1981-10-23 | Roques Bernard | Derives d'acides amines et leur application therapeutique |
| FR2488253A1 (fr) | 1980-08-08 | 1982-02-12 | Roques Bernard | Nouveaux peptides et leur application en therapeutique |
| FR2518088B1 (fr) | 1981-12-16 | 1987-11-27 | Roques Bernard | Nouveaux derives d'aminoacides, et leur application therapeutique |
| EP0130119B1 (en) * | 1983-06-23 | 1988-11-09 | Merck & Co. Inc. | (acyloxyalkoxy) carbonyl derivatives as bioreversible prodrug moieties for primary and secondary amine functions in drugs, their preparation and pharmaceutical compositions containing said derivatives |
| US4916230A (en) * | 1984-07-02 | 1990-04-10 | Merck & Co., Inc. | Process for preparing novel N-(acyloxy-alkoxy)carbonyl derivatives useful as bioreversible prodrug moieties for primary and secondary amine functions in drugs |
| FR2605004B1 (fr) | 1986-09-25 | 1989-01-13 | Centre Nat Rech Scient | Nouveaux derives d'amino-acides, leur procede de preparation et composition pharmaceutiques les contenant |
| FR2611722B1 (fr) | 1987-03-02 | 1989-08-11 | Inst Nat Sante Rech Med | Nouveaux peptides derives de la cck8, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2634763B1 (fr) | 1988-08-01 | 1991-07-12 | Inst Nat Sante Rech Med | Amino-acides et peptides presentant un residu tyrosine modifiee, leur preparation et leur application comme medicaments |
| FR2651229B1 (fr) | 1989-08-24 | 1991-12-13 | Inst Nat Sante Rech Med | Nouveaux derives d'amino-acides, leur procede de preparation et leur application therapeutique. |
| FR2679564A1 (fr) | 1991-07-23 | 1993-01-29 | Inst Nat Sante Rech Med | Nouveaux acylmercaptoalcanoldipeptides, leur preparation et les compositions qui les contiennent. |
| FR2729668A1 (fr) | 1995-01-23 | 1996-07-26 | Adir | Nouveaux derives de mercaptoalcanoyldipeptides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2745571B1 (fr) | 1996-03-04 | 1998-06-19 | Inst Nat Sante Rech Med | Nouveaux derives soufres comportant une liaison amide, leur procede de preparation, leur application a titre de medicaments, et les compositions pharmaceutiques les renfermant |
| FR2755135B1 (fr) | 1996-10-25 | 2002-12-27 | Inst Nat Sante Rech Med | Nouveaux derives d'(alpha-aminophosphino)peptides, leur procede de preparation et les compositions qui les contiennent |
| FR2773712B1 (fr) | 1998-01-16 | 2000-06-02 | Inst Nat Sante Rech Med | Composition pharmaceutique comprenant au moins un inhibiteur de l'aminopeptidase a |
| FR2777780B1 (fr) | 1998-04-22 | 2001-05-04 | Inst Nat Sante Rech Med | Derives d'(alpha-aminophosphino) peptides, leur procede de preparation et les compositions qui les contiennent |
| US20020055463A1 (en) | 1998-12-24 | 2002-05-09 | Christiane Garbay | Pseudopeptide compounds having an inhibiting activity with respect to paths activated by proteins with active tyrosine kinase activity and pharmaceutical compositions containing same |
| FR2788526B1 (fr) | 1999-01-20 | 2002-07-05 | Inst Nat Sante Rech Med | Composes tripeptidiques utiles a titre d'hinhibiteurs selectifs de l'aminopeptidase a et compositions pharmaceutiques correspondantes |
| FR2805259B1 (fr) | 2000-02-17 | 2002-03-29 | Inst Nat Sante Rech Med | Nouveaux derives d'aminoacides n-mercaptoacyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2807523B1 (fr) | 2000-04-07 | 2002-08-30 | Inst Nat Sante Rech Med | UTILISATION D'UN RESTE PyA-(Z)x-pNF A DES FINS DE DETECTION, IDENTIFICATION ET/OU DOSAGE PAR FLUORESCENCE |
| GB2362646A (en) * | 2000-05-26 | 2001-11-28 | Warner Lambert Co | Cyclic amino acid derivatives useful as pharmaceutical agents |
| FR2809733B1 (fr) | 2000-06-02 | 2004-04-30 | Inst Nat Sante Rech Med | Substrat peptidique reconnu par la toxine botulique de type bont/b et son utilisation pour doser et/ou detecter ladite toxine ou des inhibiteurs correspondants |
| ES2369256T3 (es) * | 2000-06-26 | 2011-11-28 | Helen Of Troy Limited | Sistema de lámpara recargable. |
| DE60136747D1 (de) | 2000-09-11 | 2009-01-08 | Pasteur Institut | Mitochondrialen membrane permeabilisierung durch hiv-1 vpr und screeningsverfahren |
| FR2823212B1 (fr) | 2001-04-10 | 2005-12-02 | Inst Nat Sante Rech Med | Inhibiteurs de la toxine botulique de type b |
| ES2309336T3 (es) | 2002-07-16 | 2008-12-16 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Derivados de 4,4-ditiobis-(3-aminobutano-1-sulfanatos) nuevos y composiciones que los contienen. |
| FR2858617A1 (fr) | 2003-08-06 | 2005-02-11 | Inst Nat Sante Rech Med | Derives de 4',4'-dithiobis-(3-aminobutane-1-sulfonate-1- sulfonates) nouveaux et compositions les contenant |
| ES2297742T3 (es) | 2004-05-05 | 2008-05-01 | Pharmaleads | Sustratos peptidicos reconocidos por la toxina botulinica de tipo a, bont/a y sus usos. |
| WO2007027477A2 (en) * | 2005-08-23 | 2007-03-08 | Xenoport, Inc. | Treating vulvodynia using prodrugs of gaba analogs |
| US8247609B2 (en) * | 2005-10-25 | 2012-08-21 | Pharamleads | Aminoacid derivatives containing a disulfanyl group in the form of mixed disulfanyl and aminopeptidase N inhibitors |
| WO2007048787A1 (fr) * | 2005-10-25 | 2007-05-03 | Pharmaleads | Derives d'amino-acides contenant un groupement disulfanyle comme inhibiteurs mixtes de la neprilysine et de l 'aminopeptidase n |
-
2008
- 2008-05-13 FR FR0853092A patent/FR2931151A1/fr not_active Withdrawn
-
2009
- 2009-05-13 KR KR1020107028001A patent/KR20110008325A/ko not_active Withdrawn
- 2009-05-13 WO PCT/EP2009/055787 patent/WO2009138436A1/fr not_active Ceased
- 2009-05-13 JP JP2011508908A patent/JP5642664B2/ja active Active
- 2009-05-13 EA EA201071272A patent/EA201071272A1/ru unknown
- 2009-05-13 CN CN201310736987.9A patent/CN103739531B/zh active Active
- 2009-05-13 BR BRPI0912398A patent/BRPI0912398A2/pt not_active IP Right Cessation
- 2009-05-13 MX MX2010012273A patent/MX2010012273A/es not_active Application Discontinuation
- 2009-05-13 AT AT09745768T patent/ATE555084T1/de active
- 2009-05-13 EP EP09745768A patent/EP2297095B9/fr active Active
- 2009-05-13 CN CN200980116831.2A patent/CN102026966B/zh active Active
- 2009-05-13 NZ NZ588955A patent/NZ588955A/en not_active IP Right Cessation
- 2009-05-13 AU AU2009248056A patent/AU2009248056A1/en not_active Abandoned
- 2009-05-13 CA CA2722840A patent/CA2722840C/fr active Active
- 2009-05-13 US US12/991,999 patent/US8466309B2/en active Active
-
2010
- 2010-11-09 ZA ZA2010/08029A patent/ZA201008029B/en unknown
- 2010-11-09 IL IL209214A patent/IL209214A/en active IP Right Grant
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4426391A (en) * | 1982-09-15 | 1984-01-17 | Merck & Co., Inc. | [(Alkoxycarbonyl)oxy]alkyl esters of methyldopa |
| EP1178034A1 (en) * | 2000-08-01 | 2002-02-06 | Warner-Lambert Company | Alkyl amino acid derivatives useful as pharmaceutical agents |
Non-Patent Citations (2)
| Title |
|---|
| (acyloxy)alkyl carbamates as nover bioreversible prodrugs for amines:increased permeation through biological membranes;Alenxander J.等;《Journal of medicinal chemistry》;19880101;第31卷(第2期);第318-322页 * |
| 硫乙内酰脲衍生物的合成与镇痛作用;李志裕 等;《中国药科大学学报》;19991231;第30卷(第4期);第253-255页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5642664B2 (ja) | 2014-12-17 |
| WO2009138436A1 (fr) | 2009-11-19 |
| CN102026966A (zh) | 2011-04-20 |
| MX2010012273A (es) | 2010-12-02 |
| FR2931151A1 (fr) | 2009-11-20 |
| EP2297095B1 (fr) | 2012-04-25 |
| CA2722840A1 (fr) | 2009-11-19 |
| CN102026966B (zh) | 2014-02-12 |
| KR20110008325A (ko) | 2011-01-26 |
| IL209214A (en) | 2014-08-31 |
| ZA201008029B (en) | 2011-08-31 |
| US20110071218A1 (en) | 2011-03-24 |
| BRPI0912398A2 (pt) | 2016-03-15 |
| EA201071272A1 (ru) | 2011-04-29 |
| CA2722840C (fr) | 2017-04-11 |
| ATE555084T1 (de) | 2012-05-15 |
| EP2297095B9 (fr) | 2013-01-09 |
| CN103739531A (zh) | 2014-04-23 |
| NZ588955A (en) | 2012-07-27 |
| JP2011522797A (ja) | 2011-08-04 |
| EP2297095A1 (fr) | 2011-03-23 |
| AU2009248056A1 (en) | 2009-11-19 |
| IL209214A0 (en) | 2011-01-31 |
| US8466309B2 (en) | 2013-06-18 |
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