ES2885573T3 - Nuevos compuestos de tetrazol y su uso en el tratamiento de la tuberculosis - Google Patents
Nuevos compuestos de tetrazol y su uso en el tratamiento de la tuberculosis Download PDFInfo
- Publication number
- ES2885573T3 ES2885573T3 ES18755815T ES18755815T ES2885573T3 ES 2885573 T3 ES2885573 T3 ES 2885573T3 ES 18755815 T ES18755815 T ES 18755815T ES 18755815 T ES18755815 T ES 18755815T ES 2885573 T3 ES2885573 T3 ES 2885573T3
- Authority
- ES
- Spain
- Prior art keywords
- tetrazol
- benzenesulfonamide
- hydroxyethyl
- methyl
- mmol
- 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.)
- Active
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- -1 tetrazole compounds Chemical class 0.000 title claims abstract description 130
- 238000011282 treatment Methods 0.000 title claims description 46
- 201000008827 tuberculosis Diseases 0.000 title claims description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 172
- 150000003839 salts Chemical class 0.000 claims abstract description 69
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 66
- 125000001424 substituent group Chemical group 0.000 claims abstract description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 21
- 125000005843 halogen group Chemical group 0.000 claims abstract description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 13
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 10
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 9
- 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 7
- JIYAUZMNUQFTOM-UHFFFAOYSA-N acetamidomethyl acetate Chemical compound CC(=O)NCOC(C)=O JIYAUZMNUQFTOM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 21
- 208000027531 mycobacterial infectious disease Diseases 0.000 claims description 19
- 206010062207 Mycobacterial infection Diseases 0.000 claims description 18
- 241000186359 Mycobacterium Species 0.000 claims description 17
- 208000015181 infectious disease Diseases 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 8
- ZADGDPAVPJLDBU-UHFFFAOYSA-N FC=1C=CC(=NC=1)CN1N=C(N=N1)C1=CC=C(C=C1)S(=O)(=O)NCCO Chemical compound FC=1C=CC(=NC=1)CN1N=C(N=N1)C1=CC=C(C=C1)S(=O)(=O)NCCO ZADGDPAVPJLDBU-UHFFFAOYSA-N 0.000 claims description 8
- 239000000814 tuberculostatic agent Substances 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 229940124522 antiretrovirals Drugs 0.000 claims description 6
- 239000003903 antiretrovirus agent Substances 0.000 claims description 6
- 229960003350 isoniazid Drugs 0.000 claims description 6
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical group NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 6
- 229960001225 rifampicin Drugs 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- MWTWVBRUCLGTKZ-UHFFFAOYSA-N C(#N)CNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1OCCCC1 Chemical compound C(#N)CNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1OCCCC1 MWTWVBRUCLGTKZ-UHFFFAOYSA-N 0.000 claims description 5
- YVQFTBCCLOPEHL-UHFFFAOYSA-N 2-[[4-[2-(pyridin-4-ylmethyl)tetrazol-5-yl]phenyl]sulfonylamino]acetamide Chemical compound N1=CC=C(C=C1)CN1N=C(N=N1)C1=CC=C(C=C1)S(=O)(=O)NCC(=O)N YVQFTBCCLOPEHL-UHFFFAOYSA-N 0.000 claims description 4
- DFMKQIBSFUFCFB-UHFFFAOYSA-N 2-[[4-[2-[(4-fluorophenyl)methyl]tetrazol-5-yl]phenyl]sulfonylamino]acetamide Chemical compound FC1=CC=C(CN2N=C(N=N2)C2=CC=C(C=C2)S(=O)(=O)NCC(=O)N)C=C1 DFMKQIBSFUFCFB-UHFFFAOYSA-N 0.000 claims description 4
- KYZDYKMOJSXPTN-UHFFFAOYSA-N 3-fluoro-4-[2-[(5-fluoropyridin-2-yl)methyl]tetrazol-5-yl]-N-(2-hydroxyethyl)benzenesulfonamide Chemical compound FC=1C=C(C=CC=1C=1N=NN(N=1)CC1=NC=C(C=C1)F)S(=O)(=O)NCCO KYZDYKMOJSXPTN-UHFFFAOYSA-N 0.000 claims description 4
- VMWKDHXOEVMTHN-UHFFFAOYSA-N 4-[2-[(4-fluorophenyl)methyl]tetrazol-5-yl]-N-methylbenzenesulfonamide Chemical compound FC1=CC=C(CN2N=C(N=N2)C2=CC=C(C=C2)S(=O)(=O)NC)C=C1 VMWKDHXOEVMTHN-UHFFFAOYSA-N 0.000 claims description 4
- NZHRWCHXZZTFGN-UHFFFAOYSA-N C(#N)C1=CC=C(CN2N=C(N=N2)C2=CC(=C(C=C2)S(=O)(=O)NCCO)OC)C=C1 Chemical compound C(#N)C1=CC=C(CN2N=C(N=N2)C2=CC(=C(C=C2)S(=O)(=O)NCCO)OC)C=C1 NZHRWCHXZZTFGN-UHFFFAOYSA-N 0.000 claims description 4
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- LHNLBRNTQXXTEI-UHFFFAOYSA-N N-(2-hydroxyethyl)-4-[2-(oxan-2-ylmethyl)tetrazol-5-yl]benzenesulfonamide Chemical compound OCCNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1OCCCC1 LHNLBRNTQXXTEI-UHFFFAOYSA-N 0.000 claims description 4
- MINDENKOQXRZKY-UHFFFAOYSA-N N-(2-hydroxyethyl)-4-[2-[(5-methoxypyridin-2-yl)methyl]tetrazol-5-yl]benzenesulfonamide Chemical compound OCCNS(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC1=NC=C(C=C1)OC MINDENKOQXRZKY-UHFFFAOYSA-N 0.000 claims description 4
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229950000448 sutezolid Drugs 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 210000001171 synovial bursa Anatomy 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- SVTGOXHRPOOLLN-UHFFFAOYSA-N tert-butyl N-(2-amino-2-oxoethyl)-N-[2-methoxy-4-[2-(pyridin-4-ylmethyl)tetrazol-5-yl]phenyl]sulfonylcarbamate Chemical compound NC(CN(C(OC(C)(C)C)=O)S(=O)(=O)C1=C(C=C(C=C1)C=1N=NN(N=1)CC1=CC=NC=C1)OC)=O SVTGOXHRPOOLLN-UHFFFAOYSA-N 0.000 description 1
- ZJRQFZKAPWERSF-UHFFFAOYSA-N tert-butyl N-(2-amino-2-oxoethyl)-N-[4-[2-[(4-cyanophenyl)methyl]tetrazol-5-yl]-2-methoxyphenyl]sulfonylcarbamate Chemical compound NC(CN(C(OC(C)(C)C)=O)S(=O)(=O)C1=C(C=C(C=C1)C=1N=NN(N=1)CC1=CC=C(C=C1)C#N)OC)=O ZJRQFZKAPWERSF-UHFFFAOYSA-N 0.000 description 1
- RYBHZGLIGINQKX-UHFFFAOYSA-N tert-butyl N-(2-amino-2-oxoethyl)-N-[4-[2-[1-(4-fluorophenyl)ethyl]tetrazol-5-yl]-2-methoxyphenyl]sulfonylcarbamate Chemical compound NC(CN(C(OC(C)(C)C)=O)S(=O)(=O)C1=C(C=C(C=C1)C=1N=NN(N=1)C(C)C1=CC=C(C=C1)F)OC)=O RYBHZGLIGINQKX-UHFFFAOYSA-N 0.000 description 1
- CRBPSFDRGBETCS-UHFFFAOYSA-N tert-butyl N-(cyanomethyl)-N-[4-[1-(pyridin-4-ylmethyl)triazol-4-yl]phenyl]sulfonylcarbamate Chemical compound C(#N)CN(C(OC(C)(C)C)=O)S(=O)(=O)C1=CC=C(C=C1)C=1N=NN(C=1)CC1=CC=NC=C1 CRBPSFDRGBETCS-UHFFFAOYSA-N 0.000 description 1
- HPYSHEIXVDVRKD-UHFFFAOYSA-N tert-butyl N-(cyanomethyl)-N-[4-[1-[(5-fluoropyridin-2-yl)methyl]triazol-4-yl]phenyl]sulfonylcarbamate Chemical compound C(#N)CN(C(OC(C)(C)C)=O)S(=O)(=O)C1=CC=C(C=C1)C=1N=NN(C=1)CC1=NC=C(C=C1)F HPYSHEIXVDVRKD-UHFFFAOYSA-N 0.000 description 1
- IGEYMTXFWMGZNC-UHFFFAOYSA-N tert-butyl N-(cyanomethyl)-N-[4-[2-[(6-methoxypyridin-3-yl)methyl]tetrazol-5-yl]phenyl]sulfonylcarbamate Chemical compound C(#N)CN(C(OC(C)(C)C)=O)S(=O)(=O)C1=CC=C(C=C1)C=1N=NN(N=1)CC=1C=NC(=CC=1)OC IGEYMTXFWMGZNC-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 229940075466 undecylenate Drugs 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17382574 | 2017-08-17 | ||
| PCT/EP2018/072205 WO2019034729A1 (en) | 2017-08-17 | 2018-08-16 | NOVEL TETRAZOLE COMPOUNDS AND THEIR USE IN THE TREATMENT OF TUBERCULOSIS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2885573T3 true ES2885573T3 (es) | 2021-12-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES18755815T Active ES2885573T3 (es) | 2017-08-17 | 2018-08-16 | Nuevos compuestos de tetrazol y su uso en el tratamiento de la tuberculosis |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US11072591B2 (https=) |
| EP (1) | EP3668856B1 (https=) |
| JP (1) | JP7410017B2 (https=) |
| KR (1) | KR102661367B1 (https=) |
| CN (1) | CN110997651B (https=) |
| AU (1) | AU2018317812C1 (https=) |
| CA (1) | CA3072854A1 (https=) |
| CY (1) | CY1124577T1 (https=) |
| DK (1) | DK3668856T3 (https=) |
| ES (1) | ES2885573T3 (https=) |
| HR (1) | HRP20211326T1 (https=) |
| HU (1) | HUE055732T2 (https=) |
| LT (1) | LT3668856T (https=) |
| PL (1) | PL3668856T3 (https=) |
| PT (1) | PT3668856T (https=) |
| RS (1) | RS62267B1 (https=) |
| SI (1) | SI3668856T1 (https=) |
| SM (1) | SMT202100515T1 (https=) |
| WO (1) | WO2019034729A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111184718A (zh) * | 2018-11-15 | 2020-05-22 | 鲁南制药集团股份有限公司 | 法罗培南在制备治疗初治病原学阳性肺结核药物中的用途 |
| CN115403533B (zh) * | 2021-05-28 | 2023-08-25 | 永康市第一人民医院 | 一种1-苯乙烯基-1,2,3-三氮唑化合物及其制备方法和应用 |
| CN116102483B (zh) * | 2021-11-09 | 2025-01-17 | 中国医学科学院药物研究所 | 取代吡咯-2,5-二酮类化合物及其制备方法和用途 |
| CN116726018A (zh) * | 2023-08-02 | 2023-09-12 | 上海市肺科医院（上海市职业病防治院） | 一种贝达喹啉、德拉马尼、氯法齐明和吡嗪酰胺的联用和应用 |
| CN117379430A (zh) * | 2023-10-11 | 2024-01-12 | 深圳市第三人民医院(深圳市肝病研究所) | 一种地拉韦啶的用途 |
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| JP3621427B2 (ja) | 1997-07-22 | 2005-02-16 | 塩野義製薬株式会社 | 糸球体障害治療または予防剤 |
| KR20120003499A (ko) * | 2007-04-05 | 2012-01-10 | 지멘스 메디컬 솔루션즈 유에스에이, 인크. | 클릭 화학을 이용한 탄산탈수효소―ⅰⅹ에 대한 분자 영상화 프로브의 제조 |
| WO2017066964A1 (en) | 2015-10-22 | 2017-04-27 | Merck Sharp & Dohme Corp. | Oxazolidinone compounds and methods of use thereof as antibacterial agents |
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2018
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- 2018-08-16 ES ES18755815T patent/ES2885573T3/es active Active
- 2018-08-16 HR HRP20211326TT patent/HRP20211326T1/hr unknown
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- 2018-08-16 CN CN201880053320.XA patent/CN110997651B/zh active Active
- 2018-08-16 CA CA3072854A patent/CA3072854A1/en active Pending
- 2018-08-16 LT LTEPPCT/EP2018/072205T patent/LT3668856T/lt unknown
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2021
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Also Published As
| Publication number | Publication date |
|---|---|
| EP3668856B1 (en) | 2021-06-23 |
| WO2019034729A1 (en) | 2019-02-21 |
| BR112020003247A2 (pt) | 2020-08-18 |
| JP2020531425A (ja) | 2020-11-05 |
| CA3072854A1 (en) | 2019-02-21 |
| CN110997651A (zh) | 2020-04-10 |
| SMT202100515T1 (it) | 2021-11-12 |
| PL3668856T3 (pl) | 2021-12-13 |
| CY1124577T1 (el) | 2022-07-22 |
| RU2020110818A (ru) | 2021-09-17 |
| EP3668856A1 (en) | 2020-06-24 |
| US20200231555A1 (en) | 2020-07-23 |
| RS62267B1 (sr) | 2021-09-30 |
| US11072591B2 (en) | 2021-07-27 |
| KR20200041915A (ko) | 2020-04-22 |
| JP7410017B2 (ja) | 2024-01-09 |
| HRP20211326T1 (hr) | 2021-11-26 |
| CN110997651B (zh) | 2023-01-03 |
| PT3668856T (pt) | 2021-09-15 |
| AU2018317812B2 (en) | 2021-04-15 |
| DK3668856T3 (da) | 2021-09-20 |
| HUE055732T2 (hu) | 2021-12-28 |
| RU2020110818A3 (https=) | 2021-10-11 |
| AU2018317812A1 (en) | 2020-02-20 |
| AU2018317812C1 (en) | 2021-08-26 |
| KR102661367B1 (ko) | 2024-04-29 |
| SI3668856T1 (sl) | 2021-11-30 |
| LT3668856T (lt) | 2021-09-27 |
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