HRP20221381T1 - C-manozidni spojevi korisni za liječenje infekcija urinarnog trakta - Google Patents
C-manozidni spojevi korisni za liječenje infekcija urinarnog trakta Download PDFInfo
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- HRP20221381T1 HRP20221381T1 HRP20221381TT HRP20221381T HRP20221381T1 HR P20221381 T1 HRP20221381 T1 HR P20221381T1 HR P20221381T T HRP20221381T T HR P20221381TT HR P20221381 T HRP20221381 T HR P20221381T HR P20221381 T1 HRP20221381 T1 HR P20221381T1
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- Prior art keywords
- methyl
- compound
- pharmaceutically acceptable
- acceptable salt
- hydroxy
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- 208000019206 urinary tract infection Diseases 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 13
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- BADJNWXRFSOAJF-VWJUVAHCSA-N (2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[(R)-hydroxy-[2-methyl-4-(3,4,5-trifluorophenyl)phenyl]methyl]oxane-3,4,5-triol Chemical compound O[C@@H]([C@H]1O[C@@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)C1=C(C=C(C=C1)C1=CC(=C(C(=C1)F)F)F)C BADJNWXRFSOAJF-VWJUVAHCSA-N 0.000 claims 1
- OHRKGBOWYXFISR-COXXTLHVSA-N (2R,3S,4S,5S,6R)-2-[(R)-[4-(3,5-difluoro-4-methylphenyl)-2-methylphenyl]-hydroxymethyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound FC=1C=C(C=C(C=1C)F)C1=CC(=C(C=C1)[C@H]([C@H]1O[C@@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)O)C OHRKGBOWYXFISR-COXXTLHVSA-N 0.000 claims 1
- LRMFLEFADGSAHB-HMSXXHTOSA-N (2R,3S,4S,5S,6R)-2-[(R)-[4-(3,5-difluorophenyl)-2-(trifluoromethyl)phenyl]-hydroxymethyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound FC=1C=C(C=C(C=1)F)C1=CC(=C(C=C1)[C@H]([C@H]1O[C@@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)O)C(F)(F)F LRMFLEFADGSAHB-HMSXXHTOSA-N 0.000 claims 1
- MDGCFZRSOKMPFJ-QONVVCGCSA-N (2R,3S,4S,5S,6R)-2-[(R)-[4-(3,5-difluorophenyl)-2-methylphenyl]-hydroxymethyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound FC=1C=C(C=C(C=1)F)C1=CC(=C(C=C1)[C@H]([C@H]1O[C@@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)O)C MDGCFZRSOKMPFJ-QONVVCGCSA-N 0.000 claims 1
- KAQJBNAPTMRIML-VWJUVAHCSA-N (2R,3S,4S,5S,6R)-2-[(R)-[4-(4-bromo-3,5-difluorophenyl)-2-methylphenyl]-hydroxymethyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound BrC1=C(C=C(C=C1F)C1=CC(=C(C=C1)[C@H]([C@H]1O[C@@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)O)C)F KAQJBNAPTMRIML-VWJUVAHCSA-N 0.000 claims 1
- LJPYWHRAOWHWOW-VWJUVAHCSA-N (2R,3S,4S,5S,6R)-2-[(R)-[4-(4-chloro-3,5-difluorophenyl)-2-methylphenyl]-hydroxymethyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound ClC1=C(C=C(C=C1F)C1=CC(=C(C=C1)[C@H]([C@H]1O[C@@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)O)C)F LJPYWHRAOWHWOW-VWJUVAHCSA-N 0.000 claims 1
- LRYBBHPUXCKNAH-YGBDOONVSA-N (2R,3S,4S,5S,6R)-2-[(R)-[4-(4-ethenyl-3,5-difluorophenyl)-2-methylphenyl]-hydroxymethyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound FC=1C=C(C=C(C=1C=C)F)C1=CC(=C(C=C1)[C@H]([C@H]1O[C@@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)O)C LRYBBHPUXCKNAH-YGBDOONVSA-N 0.000 claims 1
- YUCALQYRMQHOKX-QONVVCGCSA-N (2R,3S,4S,5S,6R)-2-[(R)-[4-[3-fluoro-4-(trifluoromethyl)phenyl]-2-methylphenyl]-hydroxymethyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound FC=1C=C(C=CC=1C(F)(F)F)C1=CC(=C(C=C1)[C@H]([C@H]1O[C@@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)O)C YUCALQYRMQHOKX-QONVVCGCSA-N 0.000 claims 1
- KABWSTXLWRAXMO-QONVVCGCSA-N (2R,3S,4S,5S,6R)-2-[(R)-[4-[3-fluoro-5-(trifluoromethyl)phenyl]-2-methylphenyl]-hydroxymethyl]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C(C=C1)[C@H]([C@H]1O[C@@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)O)C KABWSTXLWRAXMO-QONVVCGCSA-N 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000001668 ameliorated effect Effects 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/04—Carbocyclic radicals
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (15)
1. Spoj formule I, ili njegova farmaceutski prihvatljiva sol,
[image]
u kojem
Rl je CH3, CF3 ili Cl;
R2 je F, Cl, OR' ili H;
R3, R4 i R5 su neovisno H, F, Cl, Br, C3-6cikloalkil, OR', -N(C1-6alkil)2, C2-6 alkenil, C2-6 alkinil ili
C1-6 alkil izborno supstituiran sa do sedam atoma fluora, do jednog hidroksi, do jednog -N(C1-6 alkil)2,
i do jednog -OC1-6alkila; pod uvjetom da svi R3, R4 i R5 nisu istovremeno vodik.
R5 je H ili F;
R' je neovisno H ili C1-6 alkil izborno supstituiran sa do sedam atoma fluora.
2. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time što Rl je CH3 ili CF3.
3. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1 ili 2, naznačen time što R1 je CH3.
4. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time što
Rl je CH3 ili CF3;
R2 je H;
R3 je F;
R4 je CH3, Cl, Br, vinil, CF3, F ili H;
R5 je F ili H; i
R6 je H.
5. Spoj prema zahtjevu 4 koji je odabran između:
(2R,3S,4S,5S,6R)-2-((R)-(3',5'-difluoro-3,4'-dimetil-[1,1'-bifenil]-4-il)(hidroksi)metil)-6-(hidroksimetil)tetrahidro-2H-piran-3,4,5-triol;
(2R,3S,4S,5S,6R)-2-((R)-(4'-kloro-3',5'-difluoro-3-metil-[1,1'-bifenil]-4-il) (hidroksi)metil)-6-(hidroksimetil)tetrahidro-2H-piran-3,4,5-triol;
(2R,3S,4S,5S,6R)-2-((R)-(4'-bromo-3',5'-difluoro-3-metil-[1,1'-bifenil]-4-il) (hidroksi)metil)-6-(hidroksimetil)tetrahidro-2H-piran-3,4,5-triol;
(2R,3S,4S,5S,6R)-2-((R)-(3',5'-difluoro-3-metil-4'-vinil-[l,l'-bifenil]-4-il) (hidroksi)metil)-6-(hidroksimetil)tetrahidro-2H-piran-3,4,5-triol;
(2R,3S,4S,5S,6R)-2-((R)-(3'-fluoro-3-metil-4'-(trifluorometil)-[1,1'-bifenil]-4-il) (hidroksi)metil)-6-(hidroksimetil)tetrahidro-2H-piran-3,4,5-triol;
(2R,3S,4S,5S,6R)-2-((R)-(3'-fluoro-3-metil-5'-(trifluorometil)-[1,1'-bifenil]-4-il) (hidroksi)metil)-6-(hidroksimetil)tetrahidro-2H-piran-3,4,5-triol;
(2R,3S,4S,5S,6R)-2-((R)-hidroksi(3',4',5'-trifluoro-3-metil-[1,1'-bifenil]-4-il) metil)-6-(hidroksimetil)tetrahidro-2H-piran-3,4,5-triol;
(2R,3S,4S,5S,6R)-2-((R)-(3',5'-difluoro-3-(trifluorometil)-[1,1'-bifenil]-4-il)(hidroksi)metil)-6-(hidroksimetil)tetrahidro-2H-piran-3,4,5-triol; i
(2R,3S,4S,5S,6R)-2-((R)-(3',5'-difluoro-3-metil-[1,1'-bifenil]-4-il)(hidroksi)metil) -6-(hidroksimetil)tetrahidro-2H-piran-3,4,5-triol.
6. Spoj prema bilo kojem od zahtjeva 1 do 5, naznačen time što je spoj
[image]
7. Spoj ili njegova farmaceutski prihvatljiva sol naveden u bilo kojem od zahtjeva 1-6 za uporabu kao lijek.
8. Spoj ili njegova farmaceutski prihvatljiva sol kako je navedeno u bilo kojem od zahtjeva 1-6 za uporabu u prevenciji ili liječenju bolesti ili stanja poboljšanog inhibicijom funkcije ili aktivnosti FimH.
9. Spoj ili njegova farmaceutski prihvatljiva sol kako je navedeno u bilo kojem od zahtjeva 1-6 za uporabu u prevenciji ili liječenju bakterijske infekcije, Crohnove bolesti (CD), i upalne bolesti crijeva (IBD).
10. Spoj ili njegova farmaceutski prihvatljiva sol kako je navedeno u bilo kojem od zahtjeva 1-6 za uporabu u prevenciji ili liječenju infekcije urinarnog trakta (UTI).
11. Spoj ili njegova farmaceutski prihvatljiva sol kako je navedeno u zahtjevu 10, naznačen time što je navedena infekcija urinarnog trakta rekurentna ili kronična.
12. Spoj ili njegova farmaceutski prihvatljiva sol kako je navedeno u zahtjevu 9, naznačen time što navedena bakterijska je infekcija bakterijska infekcija otporna na antibiotike.
13. Farmaceutski pripravak koji sadrži spoj ili njegovu farmaceutski prihvatljivu sol kako je navedeno u bilo kojem od zahtjeva 1-6 zajedno s farmaceutski prihvatljivim nosačem.
14. Farmaceutski pripravak koji sadrži spoj ili njegovu farmaceutski prihvatljivu sol kako je navedeno u bilo kojem od zahtjeva 1-6 formuliran za oralnu (PO) primjenu, posebno naznačen time što je navedeni pripravak tableta ili kapsula.
15. Spoj ili njegova farmaceutski prihvatljiva sol kako je navedeno u bilo kojem od zahtjeva 1-6; i drugo terapeutsko sredstvo.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862695993P | 2018-07-10 | 2018-07-10 | |
| US201862755588P | 2018-11-05 | 2018-11-05 | |
| EP19769220.5A EP3820856B9 (en) | 2018-07-10 | 2019-07-08 | C-mannoside compopunds useful for the treatment of urinary tract infections |
| PCT/IB2019/055806 WO2020012336A1 (en) | 2018-07-10 | 2019-07-08 | C-mannoside compounds useful for the treatment of urinary tract infections |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20221381T1 true HRP20221381T1 (hr) | 2023-01-06 |
Family
ID=67957191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20221381TT HRP20221381T1 (hr) | 2018-07-10 | 2019-07-08 | C-manozidni spojevi korisni za liječenje infekcija urinarnog trakta |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US11111262B2 (hr) |
| EP (1) | EP3820856B9 (hr) |
| JP (2) | JP7309862B2 (hr) |
| KR (1) | KR20210031682A (hr) |
| CN (1) | CN112334455B (hr) |
| AU (1) | AU2019301946B2 (hr) |
| BR (1) | BR112021000370A2 (hr) |
| CA (1) | CA3105940A1 (hr) |
| CL (1) | CL2021000033A1 (hr) |
| DK (1) | DK3820856T3 (hr) |
| ES (1) | ES2928634T3 (hr) |
| HR (1) | HRP20221381T1 (hr) |
| HU (1) | HUE060140T2 (hr) |
| IL (1) | IL279993B2 (hr) |
| LT (1) | LT3820856T (hr) |
| MX (1) | MX2021000340A (hr) |
| PH (1) | PH12020551905A1 (hr) |
| PL (1) | PL3820856T3 (hr) |
| PT (1) | PT3820856T (hr) |
| RS (1) | RS63712B1 (hr) |
| SG (1) | SG11202011066XA (hr) |
| TW (1) | TWI821328B (hr) |
| UY (1) | UY38293A (hr) |
| WO (1) | WO2020012336A1 (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11202011066XA (en) | 2018-07-10 | 2021-01-28 | Glaxosmithkline Ip Dev Ltd | C-mannoside compounds useful for the treatment of urinary tract infections |
| CA3133100A1 (en) | 2019-03-19 | 2020-09-24 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic aza-benzothiophene and aza-benzofuran compounds |
| WO2021197363A1 (zh) * | 2020-03-31 | 2021-10-07 | 苏州大学 | 2-炔基甘露糖衍生物及其应用 |
| BR112022024156A2 (pt) | 2020-05-29 | 2023-02-14 | Boehringer Ingelheim Animal Health Usa Inc | Compostos heterocílicos antelmínticos |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5122602A (en) | 1989-02-13 | 1992-06-16 | Miles Inc. | Chromogenic merocyanine enzyme substrates |
| DK0730601T3 (da) | 1993-11-18 | 2005-06-06 | Univ Washington | Forbindelser og farmaceutiske præparater til behandling af profylakse af bakterieinfektioner |
| US6420127B1 (en) | 1994-11-18 | 2002-07-16 | Washington University | Compounds and pharmaceutical compositions for the treatment and prophylaxis of bacterial infections |
| DE60006390T2 (de) | 1999-06-28 | 2004-05-13 | Lear Corp., Southfield | Verfahren zum formen eines blasgeformten kunststoffteils mit filmscharnier |
| WO2001010386A2 (en) | 1999-08-11 | 2001-02-15 | Washington University | Anti-bacterial compounds directed against pilus biogenesis, adhesion and activity; co-crystals of pilus subunits and methods of use thereof |
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