JP2008546809A - 有機化合物 - Google Patents
有機化合物 Download PDFInfo
- Publication number
- JP2008546809A JP2008546809A JP2008518553A JP2008518553A JP2008546809A JP 2008546809 A JP2008546809 A JP 2008546809A JP 2008518553 A JP2008518553 A JP 2008518553A JP 2008518553 A JP2008518553 A JP 2008518553A JP 2008546809 A JP2008546809 A JP 2008546809A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- salt
- salicylic acid
- compound
- amino
- 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.)
- Pending
Links
- 150000002894 organic compounds Chemical class 0.000 title description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims abstract description 122
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims abstract description 68
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 61
- 229960004889 salicylic acid Drugs 0.000 claims abstract description 61
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims abstract description 59
- 150000003839 salts Chemical class 0.000 claims abstract description 44
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims abstract description 33
- ZRZNJUXESFHSIO-UHFFFAOYSA-N Pleuromutilin Natural products CC1C(O)C(C)(C=C)CC(OC(=O)CO)C2(C)C(C)CCC31C2C(=O)CC3 ZRZNJUXESFHSIO-UHFFFAOYSA-N 0.000 claims abstract description 32
- ZRZNJUXESFHSIO-VYTKZBNOSA-N pleuromutilin Chemical compound C([C@H]([C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CO)C)C[C@]32[C@H]1C(=O)CC3 ZRZNJUXESFHSIO-VYTKZBNOSA-N 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims description 67
- 239000000126 substance Substances 0.000 claims description 33
- 229960002771 retapamulin Drugs 0.000 claims description 13
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 10
- 206010000496 acne Diseases 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 29
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- 239000001257 hydrogen Substances 0.000 description 22
- 229910052717 sulfur Inorganic materials 0.000 description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
- 125000004434 sulfur atom Chemical group 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 229910052805 deuterium Inorganic materials 0.000 description 6
- 125000003386 piperidinyl group Chemical group 0.000 description 6
- -1 CH 2 Cl 2 Chemical class 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- STZYTFJPGGDRJD-NHUWBDDWSA-N retapamulin Chemical compound C([C@H]([C@@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CS[C@@H]3C[C@H]4CC[C@H](N4C)C3)C)C[C@]32[C@H]1C(=O)CC3 STZYTFJPGGDRJD-NHUWBDDWSA-N 0.000 description 5
- OBUUFWIMEGVAQS-UHFFFAOYSA-N Pleuromutenol Natural products CC1C(O)C(C)(C=C)CC(O)C2(C)C(C)CCC31C2C(=O)CC3 OBUUFWIMEGVAQS-UHFFFAOYSA-N 0.000 description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 229960002255 azelaic acid Drugs 0.000 description 3
- 229940067597 azelate Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940116351 sebacate Drugs 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 0 CC(CCC(CC1)(C2C1=O)C(C)C(*)C(C)(*)C1)C2(C)C1OC Chemical compound CC(CCC(CC1)(C2C1=O)C(C)C(*)C(C)(*)C1)C2(C)C1OC 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229950003188 isovaleryl diethylamide Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- LLYYNOVSVPBRGV-MVNKZKPCSA-N valnemulin Chemical compound CC(C)[C@@H](N)C(=O)NCC(C)(C)SCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 LLYYNOVSVPBRGV-MVNKZKPCSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 206010019375 Helicobacter infections Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000222350 Pleurotus Species 0.000 description 1
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 description 1
- 125000005171 cycloalkylsulfanyl group Chemical group 0.000 description 1
- 229960001259 diclofenac Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 229950008166 valnemulin Drugs 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07C323/50—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
- C07C323/52—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 the carbon skeleton being acyclic and saturated
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/54—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/95—Spiro compounds containing "not free" spiro atoms
- C07C2603/98—Spiro compounds containing "not free" spiro atoms containing at least one ring with more than six ring members
- C07C2603/99—Spiro compounds containing "not free" spiro atoms containing at least one ring with more than six ring members containing eight-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0513058.8A GB0513058D0 (en) | 2005-06-27 | 2005-06-27 | Organic compounds |
| PCT/AT2006/000242 WO2007000001A2 (en) | 2005-06-27 | 2006-06-14 | Pleuromutilin salts with salicylic acid, azelaic acid, sebacic acid and diclofenac |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008546809A true JP2008546809A (ja) | 2008-12-25 |
| JP2008546809A5 JP2008546809A5 (enExample) | 2009-07-23 |
Family
ID=34856202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008518553A Pending JP2008546809A (ja) | 2005-06-27 | 2006-06-14 | 有機化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20100160266A1 (enExample) |
| EP (1) | EP1896405B1 (enExample) |
| JP (1) | JP2008546809A (enExample) |
| AT (1) | ATE519737T1 (enExample) |
| GB (1) | GB0513058D0 (enExample) |
| TW (1) | TW200730487A (enExample) |
| WO (1) | WO2007000001A2 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7574259B1 (en) | 2004-11-12 | 2009-08-11 | Pacesetter, Inc. | Capture threshold and lead condition analysis |
| EP1808431A1 (en) * | 2006-01-16 | 2007-07-18 | Nabriva Therapeutics Forschungs GmbH | Mutilin derivatives and their use as pharmaceutical |
| JP4905182B2 (ja) | 2007-03-01 | 2012-03-28 | トヨタ自動車株式会社 | 燃料電池システム |
| EP1972618A1 (en) * | 2007-03-20 | 2008-09-24 | Nabriva Therapeutics AG | Pleuromutilin derivatives for the treatment of diseases mediated by microbes |
| US8222407B2 (en) | 2007-05-24 | 2012-07-17 | Kyorin Pharmaceutical Co., Ltd. | Mutilin derivative having heterocyclic aromatic ring carboxylic acid structure in substituent at 14-position |
| EP2014645A1 (en) * | 2007-07-13 | 2009-01-14 | Nabriva Therapeutics AG | Pleuromutilin derivatives and their use as antimicrobials |
| FR2953493B1 (fr) | 2009-12-08 | 2012-01-27 | Eurocopter France | Aeronef muni d'un dispositif d'aide au pilotage lorsqu'il porte une charge externe avec une elingue, et procede mis en oeuvre par ledit dispositif |
| US9622848B2 (en) | 2011-02-23 | 2017-04-18 | Boston Scientific Scimed, Inc. | Urethral stent system and method |
| US8728240B2 (en) * | 2012-05-02 | 2014-05-20 | Msp Corporation | Apparatus for vapor condensation and recovery |
| WO2014198752A1 (de) | 2013-06-14 | 2014-12-18 | Basf Se | Beheizbare formkörper aus elektrisch leitfähigem thermoplastischem polyurethan |
| CN105916499B (zh) | 2014-01-22 | 2020-02-18 | 纳布里瓦治疗股份公司 | 12-表-截短侧耳素 |
| DE102014115846A1 (de) | 2014-10-30 | 2016-05-04 | Maxitex Gmbh | Vorrichtung mit heizbarer Flächen von homogener Wärmeverteilung |
| TWI762573B (zh) | 2017-02-10 | 2022-05-01 | 奧地利商納畢瓦治療有限責任公司 | 截短側耳素之純化 |
| CN110054629A (zh) * | 2019-03-27 | 2019-07-26 | 广东萱嘉医品健康科技有限公司 | 一种杜鹃花酸生物碱离子盐及其制备方法与应用 |
Citations (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62215522A (ja) * | 1986-01-17 | 1987-09-22 | セレジー ファーマスーティカルズ，インコーポレイテッド | 非アクネ炎症性又は感染性皮膚疾患の治療剤 |
| JPH04264028A (ja) * | 1990-11-06 | 1992-09-18 | Ici Pharma | 相乗剤 |
| JPH05221857A (ja) * | 1992-02-14 | 1993-08-31 | Arakusu:Kk | 配合解熱鎮痛剤 |
| JPH08109120A (ja) * | 1994-10-13 | 1996-04-30 | Kao Corp | 皮膚化粧料 |
| JPH0971527A (ja) * | 1995-07-06 | 1997-03-18 | Kao Corp | 皮膚外用剤 |
| JPH1095773A (ja) * | 1996-09-19 | 1998-04-14 | Inui Kk | 抗菌活性を有するビス第四アンモニウム塩化合物及びその製造方法 |
| JP2000095763A (ja) * | 1998-09-18 | 2000-04-04 | Inui Kk | 抗菌活性を有するビス第四アンモニウム塩化合物 |
| JP2001521033A (ja) * | 1997-10-29 | 2001-11-06 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | 抗菌物質としてのプレウロムチリン誘導体 |
| JP2002284765A (ja) * | 2001-03-23 | 2002-10-03 | Hiroki Koma | ビス型第４アンモニウム塩化合物及びその製造法 |
| JP2002284697A (ja) * | 2001-01-16 | 2002-10-03 | Kanebo Ltd | 皮膚外用剤 |
| JP2003506354A (ja) * | 1999-07-30 | 2003-02-18 | バイオケミ・ゲゼルシヤフト・エム・ベー・ハー | ムチリン誘導体およびそれの抗菌剤としての使用 |
| WO2003082260A2 (en) * | 2002-03-28 | 2003-10-09 | Sandoz Ag | Tuberculosis treatment using pleuromutilin derivatives |
| JP2004502755A (ja) * | 2000-07-11 | 2004-01-29 | バイオケミ・ゲゼルシヤフト・エム・ベー・ハー | 抗細菌活性を有するプレウロムチリン誘導体 |
| JP2004509107A (ja) * | 2000-09-13 | 2004-03-25 | バイオケミ・ゲゼルシヤフト・エム・ベー・ハー | 抗菌性ムチリン |
| WO2004089886A1 (en) * | 2003-04-08 | 2004-10-21 | Glaxo Group Limited | Pleuromutilin derivatives, process for their preparation and uses thereof |
| WO2004108143A1 (de) * | 2003-06-10 | 2004-12-16 | Schering Aktiengesellschaft | Zusammensetzung aus alkandicarbonsäuren und einem pharmazeutischen wirkstoff |
| WO2005009458A1 (en) * | 2003-07-23 | 2005-02-03 | Xoma Technology Ltd. | Use of xmp-629 for the treatment of acne |
| WO2005023257A1 (en) * | 2003-09-03 | 2005-03-17 | Glaxo Group Limited | Novel process, salts, compositions and use |
| JP2005514325A (ja) * | 2001-06-25 | 2005-05-19 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | 抗微生物ナノエマルジョンの組成物および方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US516526A (en) * | 1894-03-13 | Machine for making check-row wire | ||
| BE789629A (fr) * | 1971-10-05 | 1973-04-03 | Sandoz Sa | Nouveaux derives de la pleuromutiline, leur preparation et leurapplication en therapeutique |
| US3987184A (en) * | 1974-06-07 | 1976-10-19 | Glyco Chemicals, Inc. | Dimethylol dimethylhydantoin solution |
| US3987194A (en) * | 1975-05-12 | 1976-10-19 | E. R. Squibb & Sons, Inc. | Use of pleuromutilin derivatives for the treatment of swine dysentery |
| US4130709A (en) * | 1977-12-08 | 1978-12-19 | Eli Lilly And Company | Pleuromutilin glycoside derivatives |
-
2005
- 2005-06-27 GB GBGB0513058.8A patent/GB0513058D0/en not_active Ceased
-
2006
- 2006-06-14 WO PCT/AT2006/000242 patent/WO2007000001A2/en not_active Ceased
- 2006-06-14 EP EP06752578A patent/EP1896405B1/en not_active Not-in-force
- 2006-06-14 AT AT06752578T patent/ATE519737T1/de not_active IP Right Cessation
- 2006-06-14 JP JP2008518553A patent/JP2008546809A/ja active Pending
- 2006-06-14 US US11/993,813 patent/US20100160266A1/en not_active Abandoned
- 2006-06-22 TW TW095122515A patent/TW200730487A/zh unknown
Patent Citations (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62215522A (ja) * | 1986-01-17 | 1987-09-22 | セレジー ファーマスーティカルズ，インコーポレイテッド | 非アクネ炎症性又は感染性皮膚疾患の治療剤 |
| JPH04264028A (ja) * | 1990-11-06 | 1992-09-18 | Ici Pharma | 相乗剤 |
| JPH05221857A (ja) * | 1992-02-14 | 1993-08-31 | Arakusu:Kk | 配合解熱鎮痛剤 |
| JPH08109120A (ja) * | 1994-10-13 | 1996-04-30 | Kao Corp | 皮膚化粧料 |
| JPH0971527A (ja) * | 1995-07-06 | 1997-03-18 | Kao Corp | 皮膚外用剤 |
| JPH1095773A (ja) * | 1996-09-19 | 1998-04-14 | Inui Kk | 抗菌活性を有するビス第四アンモニウム塩化合物及びその製造方法 |
| JP2001521033A (ja) * | 1997-10-29 | 2001-11-06 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | 抗菌物質としてのプレウロムチリン誘導体 |
| JP2000095763A (ja) * | 1998-09-18 | 2000-04-04 | Inui Kk | 抗菌活性を有するビス第四アンモニウム塩化合物 |
| JP2003506354A (ja) * | 1999-07-30 | 2003-02-18 | バイオケミ・ゲゼルシヤフト・エム・ベー・ハー | ムチリン誘導体およびそれの抗菌剤としての使用 |
| JP2004502755A (ja) * | 2000-07-11 | 2004-01-29 | バイオケミ・ゲゼルシヤフト・エム・ベー・ハー | 抗細菌活性を有するプレウロムチリン誘導体 |
| JP2004509107A (ja) * | 2000-09-13 | 2004-03-25 | バイオケミ・ゲゼルシヤフト・エム・ベー・ハー | 抗菌性ムチリン |
| JP2002284697A (ja) * | 2001-01-16 | 2002-10-03 | Kanebo Ltd | 皮膚外用剤 |
| JP2002284765A (ja) * | 2001-03-23 | 2002-10-03 | Hiroki Koma | ビス型第４アンモニウム塩化合物及びその製造法 |
| JP2005514325A (ja) * | 2001-06-25 | 2005-05-19 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | 抗微生物ナノエマルジョンの組成物および方法 |
| WO2003082260A2 (en) * | 2002-03-28 | 2003-10-09 | Sandoz Ag | Tuberculosis treatment using pleuromutilin derivatives |
| JP2005529088A (ja) * | 2002-03-28 | 2005-09-29 | サンド・アクチエンゲゼルシヤフト | プルロムチリン誘導体を使用する結核症治療 |
| WO2004089886A1 (en) * | 2003-04-08 | 2004-10-21 | Glaxo Group Limited | Pleuromutilin derivatives, process for their preparation and uses thereof |
| JP2006523195A (ja) * | 2003-04-08 | 2006-10-12 | グラクソ グループ リミテッド | プレウロムチリン誘導体、その製法およびその使用 |
| WO2004108143A1 (de) * | 2003-06-10 | 2004-12-16 | Schering Aktiengesellschaft | Zusammensetzung aus alkandicarbonsäuren und einem pharmazeutischen wirkstoff |
| WO2005009458A1 (en) * | 2003-07-23 | 2005-02-03 | Xoma Technology Ltd. | Use of xmp-629 for the treatment of acne |
| WO2005023257A1 (en) * | 2003-09-03 | 2005-03-17 | Glaxo Group Limited | Novel process, salts, compositions and use |
| JP2007504231A (ja) * | 2003-09-03 | 2007-03-01 | グラクソ グループ リミテッド | 新規調製方法、塩、組成物及び使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200730487A (en) | 2007-08-16 |
| EP1896405A2 (en) | 2008-03-12 |
| US20100160266A1 (en) | 2010-06-24 |
| ATE519737T1 (de) | 2011-08-15 |
| GB0513058D0 (en) | 2005-08-03 |
| WO2007000001A3 (en) | 2007-03-08 |
| WO2007000001A2 (en) | 2007-01-04 |
| EP1896405B1 (en) | 2011-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101668738B (zh) | 用于治疗微生物介导的疾病的截短侧耳素衍生物 | |
| ES2357443T3 (es) | Derivados mutilina y su uso como antimicrobianos. | |
| JP2008546809A (ja) | 有機化合物 | |
| TW502010B (en) | A pharmaceutical composition for use as nitric oxide synthase inhibitor | |
| JP7015286B2 (ja) | チオ糖粘液溶解薬 | |
| TWI834791B (zh) | 吡咯啶化合物的結晶 | |
| EA026102B1 (ru) | МОДУЛЯТОРЫ СВЯЗАННОГО С РЕТИНОИДОМ СИРОТСКОГО РЕЦЕПТОРА ГАММА (RORγ) | |
| UA122389C2 (uk) | Циклопропіламіни як інгібітори lsd1 | |
| KR20140023869A (ko) | 하이드록삼산 유도체 및 세균 감염 치료에서의 이들의 사용 | |
| CN110049970B (zh) | 作为细菌氨酰-trna合成酶抑制剂的2-氨基-n-(芳基亚磺酰基)-乙酰胺化合物 | |
| EP2321272B1 (en) | Organic compounds | |
| TW201315710A (zh) | Ｎ－（（ｓ）－３－胺基－１－（羥胺基）－３－甲基－１－酮基丁－２－基）－４－（（（１ｒ，２ｒ）－２－（羥甲基）環丙基）丁－１，３－二炔基）苯甲醯胺之多晶型 | |
| EP4603484A2 (en) | Compounds for the treatment of bacterial infections and potentiation of antibiotics | |
| CN114641466B (zh) | 磺酰脲衍生物及其用途 | |
| JPH09508363A (ja) | アミノ酸誘導体およびそのホスホリパーゼａ▲下２▼阻害剤としての用途 | |
| CN1323074C (zh) | 哌啶衍生物以及包含哌啶衍生物作为活性成分的药物组合物 | |
| WO2006090853A1 (ja) | 含窒素複素環化合物およびその医薬用途 | |
| CA2908929C (en) | Deuterated idebenone | |
| JPH03206038A (ja) | 抗菌剤 | |
| JP2025527600A (ja) | グルコシルセラミド合成酵素阻害薬の結晶形及びその使用 | |
| JP2007509905A (ja) | アクレモン酸誘導体 | |
| JPS5892637A (ja) | 新規なシス―ビシクロ［３．３．０］オクタン誘導体、当該誘導体を含有する血小板凝集抑制剤および血圧降下剤ならびに当該誘導体の製造方法 | |
| HK1153726B (en) | Organic compounds | |
| HK1090636B (en) | Mutilin derivatives and their use as antimicrobials | |
| HK1079191B (en) | Pleuromutilin derivatives as antimicrobbials |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090605 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20090605 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20120307 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120313 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20120828 |