KR20180002886A - 구충성 뎁시펩티드 화합물 - Google Patents
구충성 뎁시펩티드 화합물 Download PDFInfo
- Publication number
- KR20180002886A KR20180002886A KR1020177036636A KR20177036636A KR20180002886A KR 20180002886 A KR20180002886 A KR 20180002886A KR 1020177036636 A KR1020177036636 A KR 1020177036636A KR 20177036636 A KR20177036636 A KR 20177036636A KR 20180002886 A KR20180002886 A KR 20180002886A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- independently
- group
- halogen
- heteroaryl
- 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
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- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical class O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 title claims description 10
- 230000000507 anthelmentic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 231
- 239000000203 mixture Substances 0.000 claims abstract description 107
- 244000045947 parasite Species 0.000 claims abstract description 62
- 241001465754 Metazoa Species 0.000 claims abstract description 60
- 108010002156 Depsipeptides Proteins 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 35
- 206010061217 Infestation Diseases 0.000 claims abstract description 19
- 230000002265 prevention Effects 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 289
- 229910052739 hydrogen Inorganic materials 0.000 claims description 245
- 239000001257 hydrogen Substances 0.000 claims description 243
- 125000000217 alkyl group Chemical group 0.000 claims description 232
- 125000001424 substituent group Chemical group 0.000 claims description 227
- -1 Kiel Chemical group 0.000 claims description 214
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 195
- 125000000623 heterocyclic group Chemical group 0.000 claims description 190
- 150000002367 halogens Chemical class 0.000 claims description 188
- 125000001072 heteroaryl group Chemical group 0.000 claims description 171
- 125000003545 alkoxy group Chemical group 0.000 claims description 165
- 150000002431 hydrogen Chemical class 0.000 claims description 137
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 131
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 130
- 125000004414 alkyl thio group Chemical group 0.000 claims description 128
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 128
- 125000003118 aryl group Chemical group 0.000 claims description 127
- 125000005843 halogen group Chemical group 0.000 claims description 126
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 124
- 125000003282 alkyl amino group Chemical group 0.000 claims description 117
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 112
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 106
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 103
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 90
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 75
- 125000001188 haloalkyl group Chemical group 0.000 claims description 67
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 65
- 125000000304 alkynyl group Chemical group 0.000 claims description 62
- 125000003342 alkenyl group Chemical group 0.000 claims description 57
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 54
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 53
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 52
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 51
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 51
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 51
- 125000002757 morpholinyl group Chemical group 0.000 claims description 49
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 45
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 43
- 125000004043 oxo group Chemical group O=* 0.000 claims description 43
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 42
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 36
- 125000004076 pyridyl group Chemical group 0.000 claims description 34
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 33
- 125000002541 furyl group Chemical group 0.000 claims description 32
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 32
- 125000002883 imidazolyl group Chemical group 0.000 claims description 31
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 31
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 30
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- 125000001544 thienyl group Chemical group 0.000 claims description 28
- 125000001153 fluoro group Chemical group F* 0.000 claims description 27
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 27
- 125000002971 oxazolyl group Chemical group 0.000 claims description 27
- 238000011282 treatment Methods 0.000 claims description 23
- 239000013543 active substance Substances 0.000 claims description 21
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 230000003071 parasitic effect Effects 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000004001 thioalkyl group Chemical group 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- 108010069514 Cyclic Peptides Proteins 0.000 claims 2
- 102000001189 Cyclic Peptides Human genes 0.000 claims 2
- 230000001270 agonistic effect Effects 0.000 claims 2
- 230000003001 depressive effect Effects 0.000 claims 1
- 230000009545 invasion Effects 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 241000124008 Mammalia Species 0.000 abstract description 16
- 241000195493 Cryptophyta Species 0.000 abstract description 4
- 230000008029 eradication Effects 0.000 abstract description 2
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 112
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 54
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 description 50
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 description 50
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 46
- 125000003386 piperidinyl group Chemical group 0.000 description 45
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 41
- 238000009472 formulation Methods 0.000 description 38
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 34
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 33
- 229920000728 polyester Polymers 0.000 description 31
- 239000002904 solvent Substances 0.000 description 30
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 26
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 26
- 229920001223 polyethylene glycol Polymers 0.000 description 24
- 239000004094 surface-active agent Substances 0.000 description 24
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 23
- 125000004306 triazinyl group Chemical group 0.000 description 22
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 21
- 239000002202 Polyethylene glycol Substances 0.000 description 20
- 230000000694 effects Effects 0.000 description 19
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- 238000002425 crystallisation Methods 0.000 description 18
- 230000008025 crystallization Effects 0.000 description 18
- 208000015181 infectious disease Diseases 0.000 description 18
- 239000003112 inhibitor Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 241000002163 Mesapamea fractilinea Species 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 16
- 239000000796 flavoring agent Substances 0.000 description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 14
- 241000282472 Canis lupus familiaris Species 0.000 description 13
- 241000243988 Dirofilaria immitis Species 0.000 description 13
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 208000030852 Parasitic disease Diseases 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
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- ZNJAGNYIIOMLFU-UHFFFAOYSA-N 4-(oxan-2-yl)morpholine Chemical group O1CCCCC1N1CCOCC1 ZNJAGNYIIOMLFU-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 108010004210 PF 1022A Proteins 0.000 description 9
- YJNUXGPXJFAUQJ-LYWANRAQSA-N PF1022A Chemical compound C([C@@H]1C(=O)N(C)[C@H](C(O[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](CC=2C=CC=CC=2)C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)O1)=O)CC(C)C)C1=CC=CC=C1 YJNUXGPXJFAUQJ-LYWANRAQSA-N 0.000 description 9
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K11/00—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K11/02—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof cyclic, e.g. valinomycins ; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P17/00—Pest repellants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/15—Depsipeptides; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562163997P | 2015-05-20 | 2015-05-20 | |
| US62/163,997 | 2015-05-20 | ||
| PCT/US2016/033522 WO2016187534A1 (en) | 2015-05-20 | 2016-05-20 | Anthelmintic depsipeptide compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20180002886A true KR20180002886A (ko) | 2018-01-08 |
Family
ID=56322274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020177036636A Ceased KR20180002886A (ko) | 2015-05-20 | 2016-05-20 | 구충성 뎁시펩티드 화합물 |
Country Status (32)
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20211041T1 (hr) | 2015-05-20 | 2021-10-01 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintski depsipeptidni spojevi |
| RU2715556C2 (ru) * | 2015-12-28 | 2020-03-02 | Мериал, Инк. | Противогельминтные депсипептидные соединения |
| WO2018039508A1 (en) | 2016-08-25 | 2018-03-01 | Merial, Inc. | Method for reducing unwanted effects in parasiticidal treatments |
| JP2020504710A (ja) | 2016-11-16 | 2020-02-13 | ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド | 駆虫性デプシペプチド化合物 |
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