KR20180011772A - 신규 아미도헤테로아릴 아로일 히드라지드 에틴 - Google Patents
신규 아미도헤테로아릴 아로일 히드라지드 에틴 Download PDFInfo
- Publication number
- KR20180011772A KR20180011772A KR1020177033739A KR20177033739A KR20180011772A KR 20180011772 A KR20180011772 A KR 20180011772A KR 1020177033739 A KR1020177033739 A KR 1020177033739A KR 20177033739 A KR20177033739 A KR 20177033739A KR 20180011772 A KR20180011772 A KR 20180011772A
- Authority
- KR
- South Korea
- Prior art keywords
- pyridin
- alkyl
- methyl
- hydrazinocarbonyl
- formula
- 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.)
- Withdrawn
Links
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title description 9
- 238000000034 method Methods 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims description 55
- -1 4-methylpyridin-2-ylmethyl Chemical group 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 13
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 6
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 4
- NZXDVMRNUSTTGO-UHFFFAOYSA-N N-[5-[2-[5-[[(2-chloro-6-methylbenzoyl)amino]carbamoyl]-2-methylphenyl]ethynyl]pyridin-2-yl]cyclopropanecarboxamide Chemical compound ClC1=C(C(=O)NNC(=O)C=2C=CC(=C(C=2)C#CC=2C=CC(=NC=2)NC(=O)C2CC2)C)C(=CC=C1)C NZXDVMRNUSTTGO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- AUIIWQULVSVOFU-UHFFFAOYSA-N 1-[5-[2-[5-[[(2-chloro-6-methylbenzoyl)amino]carbamoyl]-2-methylphenyl]ethynyl]pyridin-2-yl]-3-cyclopropylurea Chemical compound ClC1=C(C(=O)NNC(=O)C=2C=CC(=C(C=2)C#CC=2C=CC(=NC=2)NC(=O)NC2CC2)C)C(=CC=C1)C AUIIWQULVSVOFU-UHFFFAOYSA-N 0.000 claims description 3
- YZCRMPXTSFCUNW-UHFFFAOYSA-N 2-fluoro-n-pyridin-2-ylacetamide Chemical compound FCC(=O)NC1=CC=CC=N1 YZCRMPXTSFCUNW-UHFFFAOYSA-N 0.000 claims description 2
- IFLOEAVTCNHYAU-UHFFFAOYSA-N N-[5-[2-[5-[[(2-chloro-6-methylbenzoyl)amino]carbamoyl]-2-methylphenyl]ethynyl]pyridin-2-yl]acetamide Chemical compound ClC1=C(C(=O)NNC(=O)C=2C=CC(=C(C=2)C#CC=2C=CC(=NC=2)NC(C)=O)C)C(=CC=C1)C IFLOEAVTCNHYAU-UHFFFAOYSA-N 0.000 claims description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940080818 propionamide Drugs 0.000 claims description 2
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
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- 238000005859 coupling reaction Methods 0.000 description 5
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- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
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- 125000005843 halogen group Chemical group 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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- 108091000080 Phosphotransferase Proteins 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 229960002448 dasatinib Drugs 0.000 description 3
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 description 3
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- 230000035772 mutation Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 102000020233 phosphotransferase Human genes 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- MZCCTJNGVFSINC-UHFFFAOYSA-N 1-cyclopropyl-3-(5-iodopyridin-2-yl)urea Chemical compound N1=CC(I)=CC=C1NC(=O)NC1CC1 MZCCTJNGVFSINC-UHFFFAOYSA-N 0.000 description 2
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
-
- 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
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/06—Formation or introduction of functional groups containing nitrogen of amide groups
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (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)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1953MU2015 | 2015-05-18 | ||
| IN1953/MUM/2015 | 2015-05-18 | ||
| PCT/IN2016/050142 WO2016185490A1 (en) | 2015-05-18 | 2016-05-18 | Novel amidoheteroaryl aroyl hydrazide ethynes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20180011772A true KR20180011772A (ko) | 2018-02-02 |
Family
ID=57319598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020177033739A Withdrawn KR20180011772A (ko) | 2015-05-18 | 2016-05-18 | 신규 아미도헤테로아릴 아로일 히드라지드 에틴 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US10150733B2 (enExample) |
| EP (1) | EP3297991B1 (enExample) |
| JP (1) | JP6689887B2 (enExample) |
| KR (1) | KR20180011772A (enExample) |
| CN (1) | CN107709300A (enExample) |
| AU (1) | AU2016263311A1 (enExample) |
| BR (1) | BR112017024633A2 (enExample) |
| CA (1) | CA2985161A1 (enExample) |
| EA (1) | EA032697B1 (enExample) |
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| EA037697B1 (ru) * | 2016-06-02 | 2021-05-12 | Сан Фарма Адвансед Ресёрч Компани Лимитед | Лечение болезни паркинсона |
| US11273126B2 (en) | 2017-03-15 | 2022-03-15 | Sun Pharma Advanced Research Company Limited | Amorphous dispersion of cyclopropanecarboxylic acid (5-{5-[N′-(2-chloro-6-methylbenzoyl) hydrazinocarbonyl]-2-methyl-phenylethynyl}-pyridin-2-yl) amide |
| EP3806858A4 (en) | 2018-06-15 | 2022-03-09 | Handa Pharmaceuticals, Inc. | KINA INHIBITOR SALTS AND COMPOSITIONS THEREOF |
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| MX2008014289A (es) * | 2006-05-08 | 2008-11-26 | Ariad Pharma Inc | Compuestos heteroarilicos acetilenicos. |
| CN103370324B (zh) * | 2010-12-27 | 2016-05-18 | 孙树萍 | 作为蛋白激酶抑制剂的芳炔类衍生物及其医疗用途 |
| EA024194B8 (ru) * | 2011-01-21 | 2016-11-30 | Сан Фарма Адвансед Ресьорч Компани Лтд | Содержащие диарилацетиленгидразид ингибиторы тирозинкиназы |
| US8859541B2 (en) * | 2012-02-27 | 2014-10-14 | Boehringer Ingelheim International Gmbh | 6-alkynylpyridines |
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| KR20190015257A (ko) * | 2016-06-02 | 2019-02-13 | 썬 파마 어드밴스트 리서치 컴패니 리미티드 | 파킨슨병의 치료 |
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| CN107709300A (zh) | 2018-02-16 |
| EP3297991A4 (en) | 2018-11-21 |
| JP6689887B2 (ja) | 2020-04-28 |
| BR112017024633A2 (pt) | 2018-07-31 |
| EP3297991B1 (en) | 2020-01-29 |
| EA201792445A1 (ru) | 2018-04-30 |
| ES2774501T3 (es) | 2020-07-21 |
| ZA201707664B (en) | 2019-08-28 |
| AU2016263311A1 (en) | 2017-11-30 |
| US10150733B2 (en) | 2018-12-11 |
| JP2018515550A (ja) | 2018-06-14 |
| EA032697B1 (ru) | 2019-07-31 |
| CA2985161A1 (en) | 2016-11-24 |
| MX2017014752A (es) | 2018-03-23 |
| US20180127372A1 (en) | 2018-05-10 |
| WO2016185490A1 (en) | 2016-11-24 |
| EP3297991A1 (en) | 2018-03-28 |
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