KR20160127127A - １,２-디히드로-3ｈ-피롤로[１,２-ｃ]이미다졸-３-온 유도체 및 항균제로서의 이의 용도 - Google Patents
１,２-디히드로-3ｈ-피롤로[１,２-ｃ]이미다졸-３-온 유도체 및 항균제로서의 이의 용도 Download PDFInfo
- Publication number
- KR20160127127A KR20160127127A KR1020167027128A KR20167027128A KR20160127127A KR 20160127127 A KR20160127127 A KR 20160127127A KR 1020167027128 A KR1020167027128 A KR 1020167027128A KR 20167027128 A KR20167027128 A KR 20167027128A KR 20160127127 A KR20160127127 A KR 20160127127A
- Authority
- KR
- South Korea
- Prior art keywords
- hydroxy
- methyl
- pyrrolo
- methylsulfonyl
- imidazol
- 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.)
- Ceased
Links
- 239000003242 anti bacterial agent Substances 0.000 title description 9
- XTYMYZJHPHOJAW-UHFFFAOYSA-N 1,2-dihydropyrrolo[1,2-c]imidazol-3-one Chemical class C1=CN2C(=O)NCC2=C1 XTYMYZJHPHOJAW-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 579
- 150000003839 salts Chemical class 0.000 claims abstract description 70
- -1 1,2-dihydroxyethyl Chemical group 0.000 claims description 633
- 238000011282 treatment Methods 0.000 claims description 53
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 150000002367 halogens Chemical class 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 32
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 29
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 27
- 208000035143 Bacterial infection Diseases 0.000 claims description 26
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 26
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 26
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 239000011737 fluorine Substances 0.000 claims description 23
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 22
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 22
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 21
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 16
- 238000011321 prophylaxis Methods 0.000 claims description 16
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- 239000003814 drug Substances 0.000 claims description 13
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 10
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 9
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
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- 125000005504 styryl group Chemical group 0.000 claims description 4
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- HIBFYWAPPXOUEE-UHFFFAOYSA-N C1C(=O)CN1C(=O)CO Chemical compound C1C(=O)CN1C(=O)CO HIBFYWAPPXOUEE-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims description 3
- 239000001273 butane Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- PTCSNXOIOPVZMT-UHFFFAOYSA-N 3-bicyclo[1.1.1]pentanylmethanol Chemical compound C1C2CC1(CO)C2 PTCSNXOIOPVZMT-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 208000027096 gram-negative bacterial infections Diseases 0.000 claims description 2
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 2
- SWYHWLFHDVMLHO-UHFFFAOYSA-N oxetan-3-ylmethanol Chemical compound OCC1COC1 SWYHWLFHDVMLHO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- QCYOIFVBYZNUNW-UHFFFAOYSA-N 2-(dimethylazaniumyl)propanoate Chemical compound CN(C)C(C)C(O)=O QCYOIFVBYZNUNW-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
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- 238000002953 preparative HPLC Methods 0.000 description 68
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- 239000011541 reaction mixture Substances 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 54
- 239000012044 organic layer Substances 0.000 description 51
- 206010057190 Respiratory tract infections Diseases 0.000 description 49
- 239000012230 colorless oil Substances 0.000 description 38
- 238000004519 manufacturing process Methods 0.000 description 38
- 239000012267 brine Substances 0.000 description 37
- 239000010410 layer Substances 0.000 description 37
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 239000000706 filtrate Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 32
- 241000894006 Bacteria Species 0.000 description 30
- 208000015181 infectious disease Diseases 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 238000004296 chiral HPLC Methods 0.000 description 28
- 239000003921 oil Substances 0.000 description 26
- 235000019198 oils Nutrition 0.000 description 26
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 229910052740 iodine Inorganic materials 0.000 description 23
- 230000002829 reductive effect Effects 0.000 description 23
- 229920006395 saturated elastomer Polymers 0.000 description 23
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 17
- 239000011630 iodine Substances 0.000 description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 17
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 16
- 229910052794 bromium Inorganic materials 0.000 description 16
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 16
- 239000003480 eluent Substances 0.000 description 16
- 229910052739 hydrogen Inorganic materials 0.000 description 16
- 239000011734 sodium Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
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- 241000589517 Pseudomonas aeruginosa Species 0.000 description 14
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 14
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- 229910052757 nitrogen Inorganic materials 0.000 description 14
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- VTORJPDWMOIOIQ-UHFFFAOYSA-N tert-butyl(diphenyl)silane Chemical compound C=1C=CC=CC=1[SiH](C(C)(C)C)C1=CC=CC=C1 VTORJPDWMOIOIQ-UHFFFAOYSA-N 0.000 description 12
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- ZJEMFURAGDYBTG-UHFFFAOYSA-N tert-butyl n-[1-(4-bromophenyl)cyclopropyl]carbamate Chemical compound C=1C=C(Br)C=CC=1C1(NC(=O)OC(C)(C)C)CC1 ZJEMFURAGDYBTG-UHFFFAOYSA-N 0.000 description 1
- FCADQNBESPLYMJ-UHFFFAOYSA-N tert-butyl n-[1-(4-iodophenyl)cyclopropyl]carbamate Chemical compound C=1C=C(I)C=CC=1C1(NC(=O)OC(C)(C)C)CC1 FCADQNBESPLYMJ-UHFFFAOYSA-N 0.000 description 1
- SHFWKQZWLHGJPA-UHFFFAOYSA-N tert-butyl-[(4-ethynylphenyl)methoxy]-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCC1=CC=C(C#C)C=C1 SHFWKQZWLHGJPA-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
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- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
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- 229960000707 tobramycin Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 206010044008 tonsillitis Diseases 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
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- YEMJHNYABQHWHL-UHFFFAOYSA-N tributyl(ethynyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C#C YEMJHNYABQHWHL-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| EP14157636.3 | 2014-03-04 | ||
| EP14157636 | 2014-03-04 | ||
| PCT/EP2015/054358 WO2015132228A1 (en) | 2014-03-04 | 2015-03-03 | 1,2-dihydro-3h-pyrrolo[1,2-c]imidazol-3-one derivatives and their use as antibacterial agents |
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| KR20160127127A true KR20160127127A (ko) | 2016-11-02 |
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| AR097617A1 (es) | 2013-09-13 | 2016-04-06 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos del 2h-indazol |
| KR20160098503A (ko) | 2013-12-19 | 2016-08-18 | 액테리온 파마슈티칼 리미티드 | 항균성 1h-인다졸 및 1h-인돌 유도체 |
| WO2015173329A1 (en) | 2014-05-16 | 2015-11-19 | Actelion Pharmaceuticals Ltd | Antibacterial quinazoline-4(3h)-one derivatives |
| AR105646A1 (es) * | 2015-08-11 | 2017-10-25 | Actelion Pharmaceuticals Ltd | Agentes antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona sustituida |
| AR105839A1 (es) * | 2015-08-28 | 2017-11-15 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos pirrolidin-2-ona anulares |
| AR105848A1 (es) * | 2015-08-31 | 2017-11-15 | Actelion Pharmaceuticals Ltd | Derivados heterocíclicos antibacterianos |
| AR105889A1 (es) | 2015-09-03 | 2017-11-22 | Actelion Pharmaceuticals Ltd | Compuestos antibacterianos 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona sustituidos |
| TW201840569A (zh) | 2017-03-01 | 2018-11-16 | 瑞士商愛杜西亞製藥有限公司 | (2r)-n-羥基-4-(6-((1-(2-羥基乙基)氮雜環丁烷-3-基)丁-1,3-二炔-1-基)-3-氧基-1h-吡咯并[1,2-c]咪唑-2(3h)-基)-2-甲基-2-(甲磺醯基)丁醯胺之結晶形式 |
| WO2019038362A1 (en) | 2017-08-24 | 2019-02-28 | Idorsia Pharmaceuticals Ltd | ANTIBACTERIAL PYRROLOIMIDAZOLONES |
| WO2019086452A1 (en) | 2017-10-31 | 2019-05-09 | Idorsia Pharmaceuticals Ltd | Antibacterial heteroaromatic compounds |
| WO2023011574A1 (zh) * | 2021-08-05 | 2023-02-09 | 浙江海正药业股份有限公司 | 芳香乙炔类衍生物及其制备方法和用途 |
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| SG2013013339A (en) | 2002-03-13 | 2014-12-30 | Array Biopharma Inc | N3 alkylated benzimidazole derivatives as mek inhibitors |
| US7781591B2 (en) | 2006-06-13 | 2010-08-24 | Wyeth Llc | Substituted 3-cyanopyridines as protein kinase inhibitors |
| DE102004017930A1 (de) | 2004-04-14 | 2005-11-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| EP1828145A4 (en) | 2004-12-10 | 2009-08-19 | Univ Emory | 2'- AND 3'-SUBSTITUTED CYCLOBUTYL NUCLEOSIDE ANALOGUE FOR THE TREATMENT OF VIRAL INFECTIONS AND ANORMAL CELL PROLIFERATION |
| JP2008001635A (ja) | 2006-06-22 | 2008-01-10 | Toray Ind Inc | グリシン誘導体及びその用途 |
| DE102008044132A1 (de) | 2008-11-27 | 2010-06-02 | BSH Bosch und Siemens Hausgeräte GmbH | Kältegerät mit zweiseitig anschlagbarer Tür |
| BRPI1013988A2 (pt) | 2009-04-06 | 2016-04-05 | Daiichi Sankyo Co Ltd | composto, composição farmacêutica , e, uso de um composto ou um sal farmacologicamente aceitável do mesmo |
| WO2010135536A2 (en) | 2009-05-20 | 2010-11-25 | Ardea Biosciences, Inc. | Methods of modulating uric acid levels |
| CN102548975A (zh) | 2009-07-07 | 2012-07-04 | 安瑟生物科技私人有限公司 | 组蛋白去乙酰化酶抑制剂 |
| CA2774250C (en) * | 2009-10-13 | 2013-12-17 | Pfizer Inc. | C-linked hydroxamic acid derivatives useful as antibacterial agents |
| JP5793766B2 (ja) | 2009-12-16 | 2015-10-14 | ファイザー・インク | 抗菌剤として有用なｎ−結合型ヒドロキサム酸誘導体 |
| EP2638006A1 (en) | 2010-11-10 | 2013-09-18 | Achaogen, Inc. | Hydroxamic acid derivatives and their use in the treatment of bacterial infections |
| KR20120079015A (ko) | 2011-01-03 | 2012-07-11 | 한미약품 주식회사 | Ｇ 단백질-커플링된 수용체의 조절을 위한 신규한 비사이클릭 화합물 |
| AP3336A (en) * | 2011-03-07 | 2015-07-31 | Pfizer | Fluoro-pyridinone derivatives useful as antibacterial agents |
| WO2012137094A1 (en) | 2011-04-08 | 2012-10-11 | Pfizer Inc. | Isoxazole derivatives useful as antibacterial agents |
| WO2012137099A1 (en) * | 2011-04-08 | 2012-10-11 | Pfizer Inc. | Imidazole, pyrazole, and triazole derivatives useful as antibacterial agents |
| US8859559B2 (en) | 2011-12-20 | 2014-10-14 | Boehringer Ingelheim International Gmbh | Substituted pyrazines and their use in the treatment of disease |
| EP2847162A1 (en) | 2012-05-09 | 2015-03-18 | Achaogen, Inc. | Antibacterial agents |
| WO2013170165A1 (en) | 2012-05-10 | 2013-11-14 | Achaogen, Inc. | Antibacterial agents |
| WO2014165075A1 (en) | 2013-03-12 | 2014-10-09 | Achaogen, Inc. | Antibacterial agents |
| AR097617A1 (es) | 2013-09-13 | 2016-04-06 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos del 2h-indazol |
| KR20160098503A (ko) | 2013-12-19 | 2016-08-18 | 액테리온 파마슈티칼 리미티드 | 항균성 1h-인다졸 및 1h-인돌 유도체 |
| WO2015173329A1 (en) | 2014-05-16 | 2015-11-19 | Actelion Pharmaceuticals Ltd | Antibacterial quinazoline-4(3h)-one derivatives |
| AR105646A1 (es) | 2015-08-11 | 2017-10-25 | Actelion Pharmaceuticals Ltd | Agentes antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona sustituida |
| AR105839A1 (es) | 2015-08-28 | 2017-11-15 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos pirrolidin-2-ona anulares |
| AR105848A1 (es) | 2015-08-31 | 2017-11-15 | Actelion Pharmaceuticals Ltd | Derivados heterocíclicos antibacterianos |
| AR105889A1 (es) | 2015-09-03 | 2017-11-22 | Actelion Pharmaceuticals Ltd | Compuestos antibacterianos 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona sustituidos |
| WO2017098440A1 (en) | 2015-12-08 | 2017-06-15 | Glaxosmithkline Intellectual Property Development Limited | Substituted benzazinones as antibacterial compounds |
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2015
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- 2015-03-03 HU HUE15707154A patent/HUE042371T2/hu unknown
- 2015-03-03 TR TR2019/00393T patent/TR201900393T4/tr unknown
- 2015-03-03 ES ES15707154T patent/ES2709382T3/es active Active
- 2015-03-03 US US15/123,184 patent/US10106544B2/en not_active Expired - Fee Related
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- 2015-03-03 EP EP15707154.9A patent/EP3114126B1/en not_active Not-in-force
- 2015-03-03 CA CA2938383A patent/CA2938383A1/en not_active Abandoned
- 2015-03-03 PT PT15707154T patent/PT3114126T/pt unknown
- 2015-03-03 KR KR1020167027128A patent/KR20160127127A/ko not_active Ceased
- 2015-03-03 CN CN201580011865.0A patent/CN106061977B/zh not_active Expired - Fee Related
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- 2015-03-03 BR BR112016020278A patent/BR112016020278A8/pt not_active Application Discontinuation
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- 2015-03-03 WO PCT/EP2015/054358 patent/WO2015132228A1/en not_active Ceased
- 2015-03-03 DK DK15707154.9T patent/DK3114126T3/en active
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- 2015-03-03 SI SI201530520T patent/SI3114126T1/sl unknown
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- 2015-03-03 LT LTEP15707154.9T patent/LT3114126T/lt unknown
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2019
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