IL216214A - History of Oxidized - Recycled Drugs for Use in the Treatment of Bacterial Infection - Google Patents
History of Oxidized - Recycled Drugs for Use in the Treatment of Bacterial InfectionInfo
- Publication number
- IL216214A IL216214A IL216214A IL21621411A IL216214A IL 216214 A IL216214 A IL 216214A IL 216214 A IL216214 A IL 216214A IL 21621411 A IL21621411 A IL 21621411A IL 216214 A IL216214 A IL 216214A
- Authority
- IL
- Israel
- Prior art keywords
- group
- compound
- compounds
- substituted
- alkyl
- Prior art date
Links
- 208000035143 Bacterial infection Diseases 0.000 title description 3
- 208000022362 bacterial infectious disease Diseases 0.000 title description 3
- 239000003118 drug derivative Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 131
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000004429 atom Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000006413 ring segment Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 239000000203 mixture Substances 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- -1 4-aza-chromane compound Chemical class 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- 230000002829 reductive effect Effects 0.000 description 30
- 238000003756 stirring Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 239000000284 extract Substances 0.000 description 13
- 238000003818 flash chromatography Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229960001233 pregabalin Drugs 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 229960003376 levofloxacin Drugs 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 9
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 8
- 239000003814 drug Substances 0.000 description 7
- 229940124307 fluoroquinolone Drugs 0.000 description 7
- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 description 7
- 125000004043 oxo group Chemical group O=* 0.000 description 7
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 229960001699 ofloxacin Drugs 0.000 description 6
- 229960003752 oseltamivir Drugs 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 229960004236 pefloxacin Drugs 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 4
- 150000001408 amides Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- FHFYDNQZQSQIAI-UHFFFAOYSA-N pefloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C)CC1 FHFYDNQZQSQIAI-UHFFFAOYSA-N 0.000 description 4
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 3
- CYMRPDYINXWJFU-UHFFFAOYSA-N 2-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=CC=C1C(O)=O CYMRPDYINXWJFU-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- HXGBXQDTNZMWGS-RUZDIDTESA-N darifenacin Chemical compound C=1C=CC=CC=1C([C@H]1CN(CCC=2C=C3CCOC3=CC=2)CC1)(C(=O)N)C1=CC=CC=C1 HXGBXQDTNZMWGS-RUZDIDTESA-N 0.000 description 3
- 229960002677 darifenacin Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
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- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- 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 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- 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
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- 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
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/52—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0908338A GB0908338D0 (en) | 2009-05-15 | 2009-05-15 | Redox drug derivatives |
| GBGB1006112.5A GB201006112D0 (en) | 2010-04-13 | 2010-04-13 | Redox drug derivatives |
| PCT/GB2010/050797 WO2010131054A1 (en) | 2009-05-15 | 2010-05-17 | Redox drug derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL216214A0 IL216214A0 (en) | 2012-01-31 |
| IL216214A true IL216214A (en) | 2015-01-29 |
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| Application Number | Title | Priority Date | Filing Date |
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| IL216214A IL216214A (en) | 2009-05-15 | 2011-11-08 | History of Oxidized - Recycled Drugs for Use in the Treatment of Bacterial Infection |
Country Status (15)
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| US (1) | US8877945B2 (https=) |
| EP (1) | EP2429991B1 (https=) |
| JP (1) | JP2012526793A (https=) |
| KR (1) | KR20120025519A (https=) |
| CN (1) | CN102459169B (https=) |
| AU (1) | AU2010247141A1 (https=) |
| BR (1) | BRPI1010981A2 (https=) |
| CA (1) | CA2762022A1 (https=) |
| EA (1) | EA201101564A1 (https=) |
| IL (1) | IL216214A (https=) |
| MX (1) | MX2011012134A (https=) |
| NZ (2) | NZ610978A (https=) |
| SG (1) | SG176056A1 (https=) |
| WO (1) | WO2010131054A1 (https=) |
| ZA (1) | ZA201108276B (https=) |
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| GB2496972A (en) * | 2011-11-18 | 2013-05-29 | Redx Pharma Ltd | Oxime and hydrazone derivatives of fluoroquinolone antibacterial drugs |
| WO2013093458A2 (en) * | 2011-12-21 | 2013-06-27 | Redx Pharma Limited | Antiviral drug derivatives |
| CN102827187B (zh) * | 2012-07-18 | 2014-05-14 | 河南大学 | 氟喹诺酮醛缩异烟腙及其制备方法和应用 |
| CA2911424C (en) | 2013-05-14 | 2021-11-30 | Biocryst Pharmaceuticals, Inc. | Anti-influenza imino-ribose pyrrolopyrimidine derivatives |
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| CA1175836A (en) | 1977-09-20 | 1984-10-09 | Marcel Pesson | Production of 1,4-dihydroquinoline-3-carboxylic acid derivatives |
| SE444566B (sv) | 1977-09-20 | 1986-04-21 | Bellon Labor Sa Roger | 7-dialkylamin-6-halogen-4-oxo-1,4-dihydrokinolin-3-karboxylsyra, forfarande for framstellning derav och farmaceutiskt preparat derav |
| JPS5746986A (en) | 1980-09-02 | 1982-03-17 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazine derivative |
| DE3333719A1 (de) | 1983-09-17 | 1985-04-04 | Bayer Ag | Loesungen milchsaurer salze von piperazinylchinolon- und piperazinyl-azachinoloncarbonsaeuren |
| JPH0635458B2 (ja) | 1985-02-15 | 1994-05-11 | 大日本製薬株式会社 | ピリドンカルボン酸誘導体、そのエステルおよびその塩 |
| DK170473B1 (da) | 1985-06-20 | 1995-09-11 | Daiichi Seiyaku Co | S(-)-pyridobenzoxazinforbindelser |
| EP0286802B1 (en) | 1987-02-26 | 1993-06-23 | Rohto Pharmaceutical Co., Ltd. | Use of ofloxacin in treating or preventing locally periodontal disease |
| JPH07113026B2 (ja) * | 1988-06-01 | 1995-12-06 | ダイセル化学工業株式会社 | オフロキサシンのエステル類の光学分割方法 |
| DE3906365A1 (de) | 1988-07-15 | 1990-01-18 | Bayer Ag | 7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
| JP2777661B2 (ja) | 1988-10-20 | 1998-07-23 | 大塚製薬株式会社 | ベンゾヘテロ環化合物 |
| GB8906166D0 (en) | 1989-03-17 | 1989-05-04 | Pfizer Ltd | Therapeutic agents |
| AP249A (en) | 1990-04-24 | 1993-03-17 | Biota Scient Management Pty Ltd | Anti-viral compounds. |
| US6197819B1 (en) * | 1990-11-27 | 2001-03-06 | Northwestern University | Gamma amino butyric acid analogs and optical isomers |
| NO179912C (no) | 1990-11-28 | 1997-01-08 | Daiichi Seiyaku Co | Analogifremgangsmåte for fremstilling av et terapeutisk virksomt optisk aktivt pyridobenzoksazinderivat |
| AU659501B2 (en) | 1991-10-23 | 1995-05-18 | Biota Scientific Management Pty Ltd | Antiviral 4-substituted-2-deoxy-2,3-didehydro-derivatives of alpha-D-neuraminic acid |
| DE4200414A1 (de) | 1992-01-10 | 1993-07-15 | Bayer Ag | Chinolon- und naphthyridon-carbonsaeure-derivate |
| NO304832B1 (no) | 1992-05-27 | 1999-02-22 | Ube Industries | Aminokinolonderivater samt middel mot HIV |
| AU673824B2 (en) | 1992-05-29 | 1996-11-28 | Bayer Aktiengesellschaft | Cyclopentane- and -pentene-beta-amino acids |
| US5235054A (en) | 1992-07-15 | 1993-08-10 | Pfizer Inc. | 3-carboxaldehyde substituted quinolines and naphthyridines |
| DE4234078A1 (de) | 1992-10-09 | 1994-04-14 | Bayer Ag | Chinoloncarbonsäuren |
| CA2112165C (en) | 1992-12-25 | 2003-04-08 | Makoto Takemura | Bicyclic amine derivatives |
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| KR0148277B1 (ko) * | 1993-01-18 | 1998-11-02 | 채영복 | 신규한 플루오르퀴놀론계 유도체 및 그의 제조방법 |
| DE4301246A1 (de) | 1993-01-19 | 1994-07-21 | Bayer Ag | Chinolon- und Naphthyridoncarbonsäurederivate |
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| DE19546249A1 (de) | 1995-12-12 | 1997-06-19 | Bayer Ag | Neue Kristallmodifikation des 1-Cyclopropyl-7-([S,S]-2,8-diazabicyclo[4,3,0]non-8-yl)-6-fluor-1,4-dihydro-8-methoxy-4-oxo-3-chinolincarbonsäure Hydrochlorid (CDCH), Verfahren zu dessen Herstellung und diese enthaltende pharmazeutische Zubereitungen |
| US5763483A (en) | 1995-12-29 | 1998-06-09 | Gilead Sciences, Inc. | Carbocyclic compounds |
| BR9707606B1 (pt) | 1996-02-23 | 2010-08-10 | ácidos 8-ciano-1-ciclopropil-7-(2,8-diazabiciclo(4.3.0) nonan-8-il)-6-flúor-1,4-diidro-4-oxo-3-quinolinocarbo xìlicos, bem como medicamentos que os compreendem. | |
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| DE19941217A1 (de) | 1999-08-30 | 2001-03-15 | Asta Medica Ag | Behandlung der Migräne durch Verabreichung von alpha-Liponsäure oder Derivaten derselben |
| MXPA02007667A (es) | 2000-02-09 | 2003-04-14 | Daiichi Seiyaku Co | Agentes antibacterianos antiacidos-resistentes que contienen acidos piridoncarboxilicos como el ingrediente activo. |
| JP2004099494A (ja) | 2002-09-09 | 2004-04-02 | Shiono Chemical Co Ltd | 光学活性三環式化合物の製造方法 |
| WO2005033108A1 (en) | 2003-09-22 | 2005-04-14 | Janssen Pharmaceutica, N.V. | 7-amino alkylidenyl-heterocyclic quinolones and naphthyridones |
| CN101010077A (zh) | 2004-06-23 | 2007-08-01 | 罗伯特·F·霍夫曼 | 靶向的氧化性治疗制剂在烧伤治疗中的用途 |
| WO2007100652A2 (en) | 2006-02-22 | 2007-09-07 | Edison Pharmaceuticals, Inc. | Side chain variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers |
| EP2017273A1 (en) | 2007-07-18 | 2009-01-21 | Laboratorios del Dr. Esteve S.A. | Process for the enantioselective preparation of pregabalin |
| EP2190439B1 (en) | 2007-08-31 | 2016-03-09 | Academia Sinica | Oseltamivir phosphonate derivatives with anti-influenza activity and synthesis thereof |
| EP2053040A1 (en) | 2007-10-26 | 2009-04-29 | Chemo Ibérica, S.A. | Pregabalin intermediates and process for preparing them and Pregabalin |
-
2010
- 2010-05-17 NZ NZ610978A patent/NZ610978A/en not_active IP Right Cessation
- 2010-05-17 AU AU2010247141A patent/AU2010247141A1/en not_active Abandoned
- 2010-05-17 NZ NZ596492A patent/NZ596492A/xx not_active IP Right Cessation
- 2010-05-17 EA EA201101564A patent/EA201101564A1/ru unknown
- 2010-05-17 SG SG2011083797A patent/SG176056A1/en unknown
- 2010-05-17 MX MX2011012134A patent/MX2011012134A/es active IP Right Grant
- 2010-05-17 CN CN201080026597.7A patent/CN102459169B/zh not_active Expired - Fee Related
- 2010-05-17 WO PCT/GB2010/050797 patent/WO2010131054A1/en not_active Ceased
- 2010-05-17 KR KR1020117029829A patent/KR20120025519A/ko not_active Ceased
- 2010-05-17 EP EP10721845.5A patent/EP2429991B1/en not_active Not-in-force
- 2010-05-17 JP JP2012510375A patent/JP2012526793A/ja active Pending
- 2010-05-17 BR BRPI1010981A patent/BRPI1010981A2/pt not_active IP Right Cessation
- 2010-05-17 US US13/319,377 patent/US8877945B2/en not_active Expired - Fee Related
- 2010-05-17 CA CA2762022A patent/CA2762022A1/en not_active Abandoned
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2011
- 2011-11-08 IL IL216214A patent/IL216214A/en not_active IP Right Cessation
- 2011-11-10 ZA ZA2011/08276A patent/ZA201108276B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN102459169B (zh) | 2014-12-31 |
| IL216214A0 (en) | 2012-01-31 |
| JP2012526793A (ja) | 2012-11-01 |
| EA201101564A1 (ru) | 2012-07-30 |
| MX2011012134A (es) | 2012-02-08 |
| SG176056A1 (en) | 2011-12-29 |
| CA2762022A1 (en) | 2010-11-18 |
| EP2429991B1 (en) | 2014-09-10 |
| EP2429991A1 (en) | 2012-03-21 |
| US8877945B2 (en) | 2014-11-04 |
| WO2010131054A1 (en) | 2010-11-18 |
| KR20120025519A (ko) | 2012-03-15 |
| ZA201108276B (en) | 2015-08-26 |
| AU2010247141A1 (en) | 2011-12-15 |
| NZ596492A (en) | 2013-08-30 |
| BRPI1010981A2 (pt) | 2018-12-04 |
| US20120077974A1 (en) | 2012-03-29 |
| CN102459169A (zh) | 2012-05-16 |
| NZ610978A (en) | 2014-11-28 |
| WO2010131054A9 (en) | 2011-05-12 |
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