JP7049349B2 - ベンジルアミノピラジニルシクロプロパンカルボン酸、その医薬組成物及び使用 - Google Patents
ベンジルアミノピラジニルシクロプロパンカルボン酸、その医薬組成物及び使用 Download PDFInfo
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- JP7049349B2 JP7049349B2 JP2019540030A JP2019540030A JP7049349B2 JP 7049349 B2 JP7049349 B2 JP 7049349B2 JP 2019540030 A JP2019540030 A JP 2019540030A JP 2019540030 A JP2019540030 A JP 2019540030A JP 7049349 B2 JP7049349 B2 JP 7049349B2
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- alkyl
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- cycloalkyl
- heterocyclyl
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 18
- SYPQXIFWJJEWSR-UHFFFAOYSA-N 2-(benzylamino)-1-pyrazin-2-ylcyclopropane-1-carboxylic acid Chemical compound C(C1=CC=CC=C1)NC1C(C1)(C(=O)O)C1=NC=CN=C1 SYPQXIFWJJEWSR-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 146
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- -1 NC- Chemical group 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 48
- 229910052731 fluorine Inorganic materials 0.000 claims description 41
- 229910052801 chlorine Inorganic materials 0.000 claims description 40
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 238000011282 treatment Methods 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 208000008589 Obesity Diseases 0.000 claims description 15
- 235000020824 obesity Nutrition 0.000 claims description 15
- 230000002265 prevention Effects 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
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- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000003566 oxetanyl group Chemical group 0.000 claims description 8
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
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- 239000000969 carrier Substances 0.000 claims description 7
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
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- 125000004076 pyridyl group Chemical group 0.000 claims description 4
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 14
- 230000001404 mediated effect Effects 0.000 description 14
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- 239000008103 glucose Substances 0.000 description 12
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- 229910052723 transition metal Inorganic materials 0.000 description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
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Classifications
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- 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
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
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- 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
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/04—Anorexiants; Antiobesity agents
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
- C07D241/20—Nitrogen atoms
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- 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
- C07D403/12—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 chain containing hetero atoms as chain links
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- 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
- C07D405/12—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 chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17153386.2 | 2017-01-26 | ||
| EP17153386 | 2017-01-26 | ||
| PCT/EP2018/051385 WO2018138028A1 (en) | 2017-01-26 | 2018-01-22 | Benzylaminopyrazinylcyclopropanecarboxylic acids, pharmaceutical compositions and uses thereof |
Publications (3)
| Publication Number | Publication Date |
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| JP2020505393A JP2020505393A (ja) | 2020-02-20 |
| JP2020505393A5 JP2020505393A5 (enExample) | 2021-01-21 |
| JP7049349B2 true JP7049349B2 (ja) | 2022-04-06 |
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| JP2019540030A Active JP7049349B2 (ja) | 2017-01-26 | 2018-01-22 | ベンジルアミノピラジニルシクロプロパンカルボン酸、その医薬組成物及び使用 |
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| US (1) | US10793530B2 (enExample) |
| EP (1) | EP3573959B1 (enExample) |
| JP (1) | JP7049349B2 (enExample) |
| CN (1) | CN110248929B (enExample) |
| WO (1) | WO2018138028A1 (enExample) |
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| WO2018138028A1 (en) * | 2017-01-26 | 2018-08-02 | Boehringer Ingelheim International Gmbh | Benzylaminopyrazinylcyclopropanecarboxylic acids, pharmaceutical compositions and uses thereof |
| WO2018138026A1 (en) * | 2017-01-26 | 2018-08-02 | Boehringer Ingelheim International Gmbh | Indanylaminopyrazinylcyclopropanecarboxylic acids, pharmaceutical compositions and uses thereof |
| WO2018138030A1 (en) * | 2017-01-26 | 2018-08-02 | Boehringer Ingelheim International Gmbh | Benzyloxypyrazinylcyclopropanecarboxylic acids, pharmaceutical compositions and uses thereof |
| CN110198928B (zh) | 2017-01-26 | 2023-08-29 | 勃林格殷格翰国际有限公司 | 苄氧基吡啶基环丙烷甲酸、其药物组合物和用途 |
| EP3573952B1 (en) * | 2017-01-26 | 2021-07-14 | Boehringer Ingelheim International GmbH | Benzylaminopyridylcyclopropanecarboxylic acids, pharmaceuticalcompositions and uses thereof |
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| US10793530B2 (en) | 2020-10-06 |
| US20190389815A1 (en) | 2019-12-26 |
| CN110248929B (zh) | 2023-05-12 |
| EP3573959A1 (en) | 2019-12-04 |
| WO2018138028A1 (en) | 2018-08-02 |
| CN110248929A (zh) | 2019-09-17 |
| JP2020505393A (ja) | 2020-02-20 |
| EP3573959B1 (en) | 2021-07-28 |
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