LV13469B - Treatment of latent tuberculosis - Google Patents
Treatment of latent tuberculosis Download PDFInfo
- Publication number
- LV13469B LV13469B LVP-05-161A LV050161A LV13469B LV 13469 B LV13469 B LV 13469B LV 050161 A LV050161 A LV 050161A LV 13469 B LV13469 B LV 13469B
- Authority
- LV
- Latvia
- Prior art keywords
- alkyl
- phenyl
- hydrogen
- use according
- formula
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims abstract description 13
- 206010065048 Latent tuberculosis Diseases 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 168
- 239000003814 drug Substances 0.000 claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- -1 cyano, hydroxy Chemical group 0.000 claims description 165
- 125000000217 alkyl group Chemical group 0.000 claims description 126
- 229910052739 hydrogen Inorganic materials 0.000 claims description 85
- 239000001257 hydrogen Substances 0.000 claims description 83
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
- 125000005843 halogen group Chemical group 0.000 claims description 72
- 150000003254 radicals Chemical class 0.000 claims description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 54
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 36
- 125000001188 haloalkyl group Chemical group 0.000 claims description 36
- 201000008827 tuberculosis Diseases 0.000 claims description 32
- 125000004122 cyclic group Chemical group 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 229940079593 drug Drugs 0.000 claims description 27
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 22
- 229940125797 compound 12 Drugs 0.000 claims description 22
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 125000001624 naphthyl group Chemical group 0.000 claims description 21
- 125000003386 piperidinyl group Chemical group 0.000 claims description 21
- 239000000460 chlorine Chemical group 0.000 claims description 20
- 230000000694 effects Effects 0.000 claims description 20
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000002883 imidazolyl group Chemical group 0.000 claims description 17
- 125000002757 morpholinyl group Chemical group 0.000 claims description 16
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 230000005059 dormancy Effects 0.000 claims description 15
- 244000052616 bacterial pathogen Species 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 241001467552 Mycobacterium bovis BCG Species 0.000 claims description 13
- 125000004193 piperazinyl group Chemical group 0.000 claims description 13
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 13
- 229960003350 isoniazid Drugs 0.000 claims description 12
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000001425 triazolyl group Chemical group 0.000 claims description 12
- 108060001084 Luciferase Proteins 0.000 claims description 11
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims description 11
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 claims description 10
- 229960000282 metronidazole Drugs 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 239000005089 Luciferase Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 8
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 238000003556 assay Methods 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 230000002085 persistent effect Effects 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 238000000338 in vitro Methods 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- 229960001225 rifampicin Drugs 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 4
- 239000011630 iodine Chemical group 0.000 claims description 4
- 229910052740 iodine Chemical group 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 208000027531 mycobacterial infectious disease Diseases 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
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- 230000004044 response Effects 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 claims description 3
- 241000186359 Mycobacterium Species 0.000 claims description 3
- 230000001355 anti-mycobacterial effect Effects 0.000 claims description 3
- QUIJNHUBAXPXFS-XLJNKUFUSA-N bedaquiline Chemical compound C1([C@H](C2=CC3=CC(Br)=CC=C3N=C2OC)[C@@](O)(CCN(C)C)C=2C3=CC=CC=C3C=CC=2)=CC=CC=C1 QUIJNHUBAXPXFS-XLJNKUFUSA-N 0.000 claims description 3
- 230000001954 sterilising effect Effects 0.000 claims description 3
- GOBOQBZOZDRXCQ-UHFFFAOYSA-N 1-(6-bromo-2-methoxyquinolin-3-yl)-4-(methylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol Chemical compound C=1C=CC2=CC=CC=C2C=1C(O)(CCNC)C(C=1C(=NC2=CC=C(Br)C=C2C=1)OC)C1=CC=CC=C1 GOBOQBZOZDRXCQ-UHFFFAOYSA-N 0.000 claims description 2
- 206010018691 Granuloma Diseases 0.000 claims description 2
- 239000003926 antimycobacterial agent Substances 0.000 claims description 2
- 229940072185 drug for treatment of tuberculosis Drugs 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
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- 238000001727 in vivo Methods 0.000 claims description 2
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- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
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- 206010062207 Mycobacterial infection Diseases 0.000 claims 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 210000000115 thoracic cavity Anatomy 0.000 claims 2
- CLLPSOGUEAXIIW-UHFFFAOYSA-N 1-(6-bromo-2-methoxyquinolin-3-yl)-2-(2,5-difluorophenyl)-4-(dimethylamino)-1-phenylbutan-2-ol Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1C(C(O)(CCN(C)C)C=1C(=CC=C(F)C=1)F)C1=CC=CC=C1 CLLPSOGUEAXIIW-UHFFFAOYSA-N 0.000 claims 1
- KDBDODKQLZKLIU-UHFFFAOYSA-N 2-nitropyrano[2,3-d]imidazole Chemical compound C1=COC2=NC([N+](=O)[O-])=NC2=C1 KDBDODKQLZKLIU-UHFFFAOYSA-N 0.000 claims 1
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- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- JQXXHWHPUNPDRT-YOPQJBRCSA-N chembl1332716 Chemical compound O([C@](C1=O)(C)O\C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)/C=C\C=C(C)/C(=O)NC=2C(O)=C3C(O)=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CCN(C)CC1 JQXXHWHPUNPDRT-YOPQJBRCSA-N 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
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- DZZWHBIBMUVIIW-DTORHVGOSA-N sparfloxacin Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F DZZWHBIBMUVIIW-DTORHVGOSA-N 0.000 claims 1
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
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- 238000013461 design Methods 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 125000005670 ethenylalkyl group Chemical group 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 239000012458 free base Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000005745 host immune response Effects 0.000 description 1
- 230000007236 host immunity Effects 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical class C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002806 hypometabolic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 229940125721 immunosuppressive agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
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- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229960003130 interferon gamma Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
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- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000003670 luciferase enzyme activity assay Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 210000003563 lymphoid tissue Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000006997 middlebrook medium Substances 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 239000013605 shuttle vector Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229940056345 tums Drugs 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
Classifications
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4704—2-Quinolinones, e.g. carbostyril
-
- 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
-
- 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
- A61P31/06—Antibacterial agents for tuberculosis
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04078529 | 2004-12-24 | ||
| EP05105008 | 2005-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LV13469B true LV13469B (en) | 2007-01-20 |
Family
ID=35717702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-05-161A LV13469B (en) | 2004-12-24 | 2005-12-09 | Treatment of latent tuberculosis |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US20060142279A1 (fr) |
| EP (1) | EP1830850B1 (fr) |
| CN (1) | CN103142595B (fr) |
| AP (1) | AP2327A (fr) |
| AR (1) | AR051790A1 (fr) |
| AT (1) | ATE501721T1 (fr) |
| AU (1) | AU2005242138B2 (fr) |
| BR (1) | BRPI0506400B8 (fr) |
| CA (1) | CA2529265C (fr) |
| CR (1) | CR9267A (fr) |
| CY (1) | CY1112247T1 (fr) |
| DE (1) | DE602005026984D1 (fr) |
| DK (1) | DK1830850T3 (fr) |
| EE (1) | EE05394B1 (fr) |
| HR (1) | HRP20110392T1 (fr) |
| IL (1) | IL184123A (fr) |
| LV (1) | LV13469B (fr) |
| ME (1) | ME01207B (fr) |
| MY (1) | MY145845A (fr) |
| NI (1) | NI200700146A (fr) |
| NO (1) | NO340376B1 (fr) |
| NZ (1) | NZ555460A (fr) |
| PA (1) | PA8654801A1 (fr) |
| PL (1) | PL1830850T3 (fr) |
| PT (1) | PT1830850E (fr) |
| RS (1) | RS51730B (fr) |
| SI (1) | SI1830850T1 (fr) |
| TR (1) | TR200504892A1 (fr) |
| TW (1) | TWI404535B (fr) |
| WO (1) | WO2006067048A1 (fr) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE463482T1 (de) * | 2002-07-25 | 2010-04-15 | Janssen Pharmaceutica Nv | Chinolinderivate und deren verwendung als mycobakterielle inhibitoren |
| KR101329587B1 (ko) * | 2005-06-28 | 2013-11-15 | 얀센 파마슈티카 엔.브이. | 항균제로서의 퀴놀린 유도체 |
| JO2752B1 (en) | 2005-06-28 | 2014-03-15 | شركة جانسين فارماسوتيكا ان. في | Quinoline derivatives acting as antibacterial agents |
| JO3270B1 (ar) * | 2005-06-28 | 2018-09-16 | Janssen Pharmaceutica Nv | مشتقات كوينولين بصفة عوامل مضادة للبكتيريا |
| JO3271B1 (ar) | 2006-12-06 | 2018-09-16 | Janssen Pharmaceutica Nv | مشتقات الكوينولين المضادة للجراثيم |
| JO2970B1 (en) | 2006-12-06 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Quinoline antibacterial derivatives |
| JO2683B1 (en) * | 2006-12-06 | 2013-03-03 | جانسين فارماسوتيكا ان. في | Quinoline antibacterial derivatives |
| JO2725B1 (en) * | 2006-12-06 | 2013-09-15 | جانسين فارماسوتيكا ان. في | Quinoline antibacterial derivatives |
| CA2711912A1 (fr) * | 2008-01-14 | 2009-07-23 | Jyoti Chattopadhyaya | Derives de quinoleine, de naphtalene, de quinoleine ou de naphtalene contraint au niveau conformation en tant qu'agents antimycobacteriens |
| RU2404971C2 (ru) * | 2008-12-02 | 2010-11-27 | ЗАО "Фарм-Синтез" | Новые производные хинолина, способ их получения, их применение для лечения микобактериальных инфекций, фармацевтическая композиция на их основе |
| EP2387564A1 (fr) | 2009-01-15 | 2011-11-23 | Rutgers, The State University of New Jersey | Benzoýc¨phénanthridines comme agents antimicrobiens |
| CA2760526A1 (fr) | 2009-04-30 | 2010-11-04 | Rutgers, The State University Of New Jersey | Agents antimicrobiens |
| US8933096B2 (en) | 2010-06-09 | 2015-01-13 | Rugers, The State University of New Jersey | Antimicrobial agents |
| CA2803890A1 (fr) | 2010-06-25 | 2011-12-29 | Rutgers, The State University Of New Jersey | Agents antimicrobiens |
| WO2013106756A2 (fr) | 2012-01-13 | 2013-07-18 | Rutgers, The State University Of New Jersey | Agents antimicrobiens |
| EP2828245A1 (fr) | 2012-03-21 | 2015-01-28 | Rutgers, The State University of New Jersey | Agents anti-microbiens |
| ES2607879T3 (es) | 2012-04-27 | 2017-04-04 | Janssen Pharmaceutica N.V. | Derivados de quinolina antibacterianos |
| CN104254527B (zh) | 2012-04-27 | 2017-05-31 | 詹森药业有限公司 | 抗菌的喹啉衍生物 |
| US9458150B2 (en) | 2013-11-08 | 2016-10-04 | Rutgers, The State University Of New Jersey | Antimicrobial agents |
| IL310920A (en) | 2015-01-27 | 2024-04-01 | Janssen Pharmaceutica Nv | Dispersible compositions |
| US10513528B2 (en) | 2016-02-25 | 2019-12-24 | Taxis Pharmaceuticals, Inc. | Synthetic processes and intermediates |
| BR122023025283A2 (pt) * | 2016-03-07 | 2024-02-20 | Global Alliance For Tb Drug Development Inc | Compostos antibacterianos e seus usos |
| RU2629369C1 (ru) * | 2016-10-05 | 2017-08-29 | Федеральное Государственное Унитарное Предприятие "Государственный Ордена Трудового Красного Знамени Научно-Исследовательский Институт Химических Реактивов И Особо Чистых Химических Веществ" | Четвертичные аммонийные производные 2-аминотиофен-3-карбоксилатов, обладающие противотуберкулезной активностью |
| WO2018183917A1 (fr) | 2017-03-30 | 2018-10-04 | Taxis Pharmaceuticals, Inc. | Procédés de synthèse et intermédiaires de synthèse |
| SI3943070T1 (sl) | 2017-07-14 | 2024-03-29 | Janssen Pharmaceutica Nv, | Dolgo delujoče formulacije bedakilina |
| RU2661151C1 (ru) * | 2017-12-14 | 2018-07-12 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) | Селективные ингибиторы глицеральдегид-3-фосфатдегидрогеназы микобактерий |
| WO2020144197A1 (fr) | 2019-01-09 | 2020-07-16 | Janssen Pharmaceutica Nv | Combinaison dans le traitement de maladies mycobactériennes non tuberculeuses |
| MX2023000439A (es) | 2020-07-09 | 2023-02-09 | Janssen Pharmaceutica Nv | Formulaciones a largo plazo. |
| CN115776882A (zh) | 2020-07-09 | 2023-03-10 | 詹森药业有限公司 | 长效配制品 |
| KR20230107275A (ko) | 2020-11-12 | 2023-07-14 | 얀센 파마슈티카 엔.브이. | 비결핵성 마이코박테리아 질환의 치료에서 베다퀼린, 에탐부톨 및 마크롤라이드의 조합물 |
| WO2023232838A1 (fr) | 2022-05-31 | 2023-12-07 | Janssen Pharmaceutica Nv | Bédaquiline destinée à être utilisée dans le traitement de la lèpre |
| CN119968203A (zh) | 2022-09-28 | 2025-05-09 | 詹森药业有限公司 | 长效配制品 |
| WO2024068693A1 (fr) | 2022-09-28 | 2024-04-04 | Janssen Pharmaceutica Nv | Formulations à action prolongée |
| WO2025068448A1 (fr) | 2023-09-28 | 2025-04-03 | Janssen Pharmaceutica Nv | Inhibiteurs de l'atp synthase destinés à être utilisés dans le traitement de mycobactéries non tuberculeuses |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR038536A1 (es) * | 2002-02-25 | 2005-01-19 | Upjohn Co | N-aril-2-oxazolidinona-5- carboxamidas y sus derivados |
| ATE463482T1 (de) * | 2002-07-25 | 2010-04-15 | Janssen Pharmaceutica Nv | Chinolinderivate und deren verwendung als mycobakterielle inhibitoren |
-
2005
- 2005-12-05 EE EEP200500033A patent/EE05394B1/xx unknown
- 2005-12-06 CA CA2529265A patent/CA2529265C/fr not_active Expired - Lifetime
- 2005-12-07 PA PA20058654801A patent/PA8654801A1/es unknown
- 2005-12-07 AU AU2005242138A patent/AU2005242138B2/en not_active Expired
- 2005-12-07 MY MYPI20055732A patent/MY145845A/en unknown
- 2005-12-08 SI SI200531294T patent/SI1830850T1/sl unknown
- 2005-12-08 EP EP05815816A patent/EP1830850B1/fr not_active Expired - Lifetime
- 2005-12-08 PL PL05815816T patent/PL1830850T3/pl unknown
- 2005-12-08 ME MEP-2011-92A patent/ME01207B/fr unknown
- 2005-12-08 TW TW094143290A patent/TWI404535B/zh active
- 2005-12-08 AT AT05815816T patent/ATE501721T1/de active
- 2005-12-08 BR BRPI0506400A patent/BRPI0506400B8/pt not_active IP Right Cessation
- 2005-12-08 AP AP2007004054A patent/AP2327A/xx active
- 2005-12-08 CN CN201210507318.XA patent/CN103142595B/zh not_active Expired - Fee Related
- 2005-12-08 TR TR2005/04892A patent/TR200504892A1/xx unknown
- 2005-12-08 WO PCT/EP2005/056594 patent/WO2006067048A1/fr not_active Ceased
- 2005-12-08 US US11/296,992 patent/US20060142279A1/en not_active Abandoned
- 2005-12-08 DE DE602005026984T patent/DE602005026984D1/de not_active Expired - Lifetime
- 2005-12-08 RS RS20110221A patent/RS51730B/sr unknown
- 2005-12-08 PT PT05815816T patent/PT1830850E/pt unknown
- 2005-12-08 DK DK05815816.3T patent/DK1830850T3/da active
- 2005-12-08 NZ NZ555460A patent/NZ555460A/en not_active IP Right Cessation
- 2005-12-08 HR HR20110392T patent/HRP20110392T1/hr unknown
- 2005-12-09 AR ARP050105140A patent/AR051790A1/es unknown
- 2005-12-09 LV LVP-05-161A patent/LV13469B/lv unknown
-
2007
- 2007-06-05 NI NI200700146A patent/NI200700146A/es unknown
- 2007-06-21 IL IL184123A patent/IL184123A/en active IP Right Grant
- 2007-07-20 CR CR9267A patent/CR9267A/es not_active Application Discontinuation
- 2007-07-23 NO NO20073823A patent/NO340376B1/no unknown
-
2011
- 2011-06-15 CY CY20111100563T patent/CY1112247T1/el unknown
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