JP2017519801A - 犬糸状虫に対する駆虫薬の使用 - Google Patents
犬糸状虫に対する駆虫薬の使用 Download PDFInfo
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- JP2017519801A JP2017519801A JP2017500885A JP2017500885A JP2017519801A JP 2017519801 A JP2017519801 A JP 2017519801A JP 2017500885 A JP2017500885 A JP 2017500885A JP 2017500885 A JP2017500885 A JP 2017500885A JP 2017519801 A JP2017519801 A JP 2017519801A
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- alkoxy
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- 229940079593 drug Drugs 0.000 title description 4
- 239000003814 drug Substances 0.000 title description 4
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- 208000015181 infectious disease Diseases 0.000 claims abstract description 36
- 241000282465 Canis Species 0.000 claims abstract description 34
- 241001465754 Metazoa Species 0.000 claims abstract description 18
- 201000006353 Filariasis Diseases 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 247
- 125000001424 substituent group Chemical group 0.000 claims description 230
- -1 arylalkylsulfanyl Chemical group 0.000 claims description 174
- 229910052736 halogen Inorganic materials 0.000 claims description 173
- 150000002367 halogens Chemical class 0.000 claims description 145
- 125000003545 alkoxy group Chemical group 0.000 claims description 118
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 108
- 125000001072 heteroaryl group Chemical group 0.000 claims description 101
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 87
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 125000005647 linker group Chemical group 0.000 claims description 57
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 53
- 125000001188 haloalkyl group Chemical group 0.000 claims description 52
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 41
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- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims description 32
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000004439 haloalkylsulfanyl group Chemical group 0.000 claims description 28
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 26
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
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- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 18
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 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 description 14
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
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- 238000000034 method Methods 0.000 claims description 9
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
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- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
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- 238000002560 therapeutic procedure Methods 0.000 abstract 1
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- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 30
- 125000000623 heterocyclic group Chemical group 0.000 description 19
- 229910052799 carbon Inorganic materials 0.000 description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 16
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- 241000282472 Canis lupus familiaris Species 0.000 description 15
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 125000001309 chloro group Chemical group Cl* 0.000 description 13
- 238000001514 detection method Methods 0.000 description 13
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 12
- 150000001768 cations Chemical class 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 10
- 239000000047 product Substances 0.000 description 10
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000011067 equilibration Methods 0.000 description 9
- 125000001153 fluoro group Chemical group F* 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 238000012856 packing Methods 0.000 description 9
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- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 8
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- 125000004076 pyridyl group Chemical group 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 241000255925 Diptera Species 0.000 description 7
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 241000282421 Canidae Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000282326 Felis catus Species 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000004602 benzodiazinyl group Chemical group N1=NC(=CC2=C1C=CC=C2)* 0.000 description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000005990 isobenzothienyl group Chemical group 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 244000052769 pathogen Species 0.000 description 6
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- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 5
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- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 5
- 238000000105 evaporative light scattering detection Methods 0.000 description 5
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- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 5
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- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 4
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
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- 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
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- Animal Behavior & Ethology (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
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| EP14176737.6 | 2014-07-11 | ||
| EP14176737 | 2014-07-11 | ||
| PCT/EP2015/065870 WO2016005577A1 (en) | 2014-07-11 | 2015-07-10 | Use of anthelmintic agents against dirofilaria immitis |
Publications (2)
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| JP2017519801A true JP2017519801A (ja) | 2017-07-20 |
| JP2017519801A5 JP2017519801A5 (enExample) | 2018-07-26 |
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| JP2017500885A Withdrawn JP2017519801A (ja) | 2014-07-11 | 2015-07-10 | 犬糸状虫に対する駆虫薬の使用 |
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| EP (1) | EP3166605A1 (enExample) |
| JP (1) | JP2017519801A (enExample) |
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| AU (1) | AU2015286635A1 (enExample) |
| BR (1) | BR112017000520A2 (enExample) |
| WO (1) | WO2016005577A1 (enExample) |
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| KR102007135B1 (ko) | 2017-03-20 | 2019-08-02 | 포르마 세라퓨틱스 인크. | 피루베이트 키나제 (pkr) 활성화제로서의 피롤로피롤 조성물 |
| JOP20190223A1 (ar) | 2017-04-01 | 2019-09-26 | Novartis Ag | عملية لتحضير حمض 1-(4- ميثان سلفونيل -2- تراي فلورو ميثيل - بنزيل)-2- ميثيل -1h- بيرولو [2، 3-b] بيريدين -3- يل- أسيتيك |
| US20200129485A1 (en) | 2018-09-19 | 2020-04-30 | Forma Therapeutics, Inc. | Treating sickle cell disease with a pyruvate kinase r activating compound |
| EP3852791B1 (en) | 2018-09-19 | 2024-07-03 | Novo Nordisk Health Care AG | Activating pyruvate kinase r |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| EP3980414A1 (en) | 2019-06-07 | 2022-04-13 | Elanco Tiergesundheit AG | Bicyclic derivatives for treating endoparasites |
| US20220378756A1 (en) | 2019-09-19 | 2022-12-01 | Forma Therapeutics, Inc. | Activating pyruvate kinase r |
| WO2021174069A1 (en) | 2020-02-28 | 2021-09-02 | Auburn University | Dirofilaria volatile organic compound signatures and uses thereof |
| US12473300B2 (en) | 2020-03-06 | 2025-11-18 | Guangzhou Maxinovel Pharmaceuticals Co., Ltd. | Thienopyrimidine derivative and preparation method therefor |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
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| TW200938203A (en) * | 2007-12-17 | 2009-09-16 | Intervet Int Bv | Anthelmintic agents and their use |
| TW201041868A (en) * | 2009-03-20 | 2010-12-01 | Intervet Int Bv | Anthelmintic agents and their use |
| TW201111358A (en) * | 2009-06-18 | 2011-04-01 | Intervet Int Bv | Anthelmintic agents and their use |
| EP2468096A1 (en) * | 2010-12-21 | 2012-06-27 | Intervet International BV | Anthelmintic combinations |
| AU2013348175B2 (en) * | 2012-11-20 | 2016-11-17 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic compounds and compositions and method of using thereof |
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2015
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- 2015-07-10 US US15/324,896 patent/US20170196854A1/en not_active Abandoned
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- 2015-07-10 AU AU2015286635A patent/AU2015286635A1/en not_active Abandoned
- 2015-07-10 EP EP15738607.9A patent/EP3166605A1/en not_active Withdrawn
- 2015-07-10 JP JP2017500885A patent/JP2017519801A/ja not_active Withdrawn
- 2015-07-10 CN CN201580037488.8A patent/CN106470683A/zh active Pending
Also Published As
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| BR112017000520A2 (pt) | 2017-11-14 |
| US20170196854A1 (en) | 2017-07-13 |
| EP3166605A1 (en) | 2017-05-17 |
| WO2016005577A1 (en) | 2016-01-14 |
| CN106470683A (zh) | 2017-03-01 |
| AU2015286635A1 (en) | 2017-01-19 |
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