KR20100075518A - 인돌린 화합물 - Google Patents
인돌린 화합물 Download PDFInfo
- Publication number
- KR20100075518A KR20100075518A KR1020107008669A KR20107008669A KR20100075518A KR 20100075518 A KR20100075518 A KR 20100075518A KR 1020107008669 A KR1020107008669 A KR 1020107008669A KR 20107008669 A KR20107008669 A KR 20107008669A KR 20100075518 A KR20100075518 A KR 20100075518A
- Authority
- KR
- South Korea
- Prior art keywords
- indol
- ethyl
- dihydro
- acetamide
- methoxy
- 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- Withdrawn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
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 title 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 45
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract description 26
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims abstract description 26
- -1 indolin compound Chemical class 0.000 claims abstract description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 8
- BEGUCBIBFPEXBJ-UHFFFAOYSA-N 1-[2-(6-methoxy-2,3-dihydroindol-1-yl)ethyl]cyclopropane-1-carboxamide Chemical compound C12=CC(OC)=CC=C2CCN1CCC1(C(N)=O)CC1 BEGUCBIBFPEXBJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- FZIOCLNQSSZLEQ-UHFFFAOYSA-N 1-[2-[6-(2-phenylethoxy)-2,3-dihydroindol-1-yl]ethyl]cyclopropane-1-carboxamide Chemical compound C1CC2=CC=C(OCCC=3C=CC=CC=3)C=C2N1CCC1(C(=O)N)CC1 FZIOCLNQSSZLEQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- VGEGJTNFJKGJSG-UHFFFAOYSA-N 2,2,2-trifluoro-n-[2-(6-methoxy-2,3-dihydroindol-1-yl)ethyl]acetamide Chemical compound COC1=CC=C2CCN(CCNC(=O)C(F)(F)F)C2=C1 VGEGJTNFJKGJSG-UHFFFAOYSA-N 0.000 claims abstract description 5
- VUEUYLMHINPZCP-UHFFFAOYSA-N 2,2,2-trifluoro-n-[2-[6-(3-phenylpropoxy)-2,3-dihydroindol-1-yl]ethyl]acetamide Chemical compound C1=C2N(CCNC(=O)C(F)(F)F)CCC2=CC=C1OCCCC1=CC=CC=C1 VUEUYLMHINPZCP-UHFFFAOYSA-N 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 5
- HTQZTNCKIQGQLW-UHFFFAOYSA-N n-[2-(5-bromo-6-methoxy-2,3-dihydroindol-1-yl)ethyl]acetamide Chemical compound C1=C(Br)C(OC)=CC2=C1CCN2CCNC(C)=O HTQZTNCKIQGQLW-UHFFFAOYSA-N 0.000 claims abstract description 5
- SAUVZPBRAOWWHN-UHFFFAOYSA-N n-[2-(6-methoxy-2,3-dihydroindol-1-yl)ethyl]propanamide Chemical compound C1=C(OC)C=C2N(CCNC(=O)CC)CCC2=C1 SAUVZPBRAOWWHN-UHFFFAOYSA-N 0.000 claims abstract description 5
- DCNUJKSLBGXCCL-UHFFFAOYSA-N n-[2-(6-methoxy-3-methyl-2,3-dihydroindol-1-yl)ethyl]acetamide Chemical compound COC1=CC=C2C(C)CN(CCNC(C)=O)C2=C1 DCNUJKSLBGXCCL-UHFFFAOYSA-N 0.000 claims abstract description 5
- BBCSQPHKBFZMRF-UHFFFAOYSA-N n-[2-(6-methoxy-5-phenyl-2,3-dihydroindol-1-yl)ethyl]acetamide Chemical compound COC1=CC=2N(CCNC(C)=O)CCC=2C=C1C1=CC=CC=C1 BBCSQPHKBFZMRF-UHFFFAOYSA-N 0.000 claims abstract description 5
- KVBUIYXZHDWRSA-UHFFFAOYSA-N n-[2-(6-methoxy-5-pyridin-4-yl-2,3-dihydroindol-1-yl)ethyl]acetamide Chemical compound COC1=CC=2N(CCNC(C)=O)CCC=2C=C1C1=CC=NC=C1 KVBUIYXZHDWRSA-UHFFFAOYSA-N 0.000 claims abstract description 5
- LIGFXOOCMXHVFZ-UHFFFAOYSA-N n-[2-[6-(2-phenylethoxy)-2,3-dihydroindol-1-yl]ethyl]acetamide Chemical compound C1=C2N(CCNC(=O)C)CCC2=CC=C1OCCC1=CC=CC=C1 LIGFXOOCMXHVFZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- NNMKLYXVTDXENJ-UHFFFAOYSA-N n-[2-[6-(2-phenylethoxy)-2,3-dihydroindol-1-yl]ethyl]propanamide Chemical compound C1=C2N(CCNC(=O)CC)CCC2=CC=C1OCCC1=CC=CC=C1 NNMKLYXVTDXENJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- GXCQXEGURQQACG-UHFFFAOYSA-N n-[2-[6-(3-phenylpropoxy)-2,3-dihydroindol-1-yl]ethyl]butanamide Chemical compound C1=C2N(CCNC(=O)CCC)CCC2=CC=C1OCCCC1=CC=CC=C1 GXCQXEGURQQACG-UHFFFAOYSA-N 0.000 claims abstract description 5
- HRDIWAMPNHYPTG-UHFFFAOYSA-N n-[2-[6-(3-phenylpropoxy)-2,3-dihydroindol-1-yl]ethyl]propanamide Chemical compound C1=C2N(CCNC(=O)CC)CCC2=CC=C1OCCCC1=CC=CC=C1 HRDIWAMPNHYPTG-UHFFFAOYSA-N 0.000 claims abstract description 5
- SBYZSLNIQGCLLI-UHFFFAOYSA-N n-[2-[6-(4-phenylbutoxy)-2,3-dihydroindol-1-yl]ethyl]acetamide Chemical compound C1=C2N(CCNC(=O)C)CCC2=CC=C1OCCCCC1=CC=CC=C1 SBYZSLNIQGCLLI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
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- 238000000034 method Methods 0.000 claims description 24
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- 208000012672 seasonal affective disease Diseases 0.000 claims description 9
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- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 8
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 8
- 208000020401 Depressive disease Diseases 0.000 claims description 7
- 210000002249 digestive system Anatomy 0.000 claims description 7
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 7
- 208000024714 major depressive disease Diseases 0.000 claims description 7
- 201000003995 melancholia Diseases 0.000 claims description 7
- 230000001193 melatoninergic effect Effects 0.000 claims description 7
- 206010027599 migraine Diseases 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
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- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 4
- 206010016256 fatigue Diseases 0.000 claims description 4
- 150000002475 indoles Chemical class 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims 2
- 230000036528 appetite Effects 0.000 claims 1
- 235000019789 appetite Nutrition 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- LRSCUDLZEOJNEN-UHFFFAOYSA-N n-[2-(6-methoxy-2,3-dihydroindol-1-yl)ethyl]acetamide Chemical compound COC1=CC=C2CCN(CCNC(C)=O)C2=C1 LRSCUDLZEOJNEN-UHFFFAOYSA-N 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 230000009257 reactivity Effects 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 102100024930 Melatonin receptor type 1A Human genes 0.000 description 10
- 101710098568 Melatonin receptor type 1A Proteins 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 9
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 8
- 102100024970 Melatonin receptor type 1B Human genes 0.000 description 8
- 101710098567 Melatonin receptor type 1B Proteins 0.000 description 8
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 8
- 229960003987 melatonin Drugs 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical class C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 7
- YHIPILPTUVMWQT-UHFFFAOYSA-N Oplophorus luciferin Chemical compound C1=CC(O)=CC=C1CC(C(N1C=C(N2)C=3C=CC(O)=CC=3)=O)=NC1=C2CC1=CC=CC=C1 YHIPILPTUVMWQT-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000556 agonist Substances 0.000 description 6
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 102100029698 Metallothionein-1A Human genes 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 230000008484 agonism Effects 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 102000001419 Melatonin receptor Human genes 0.000 description 3
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- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
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- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
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- IZQAUUVBKYXMET-UHFFFAOYSA-N 2-bromoethanamine Chemical compound NCCBr IZQAUUVBKYXMET-UHFFFAOYSA-N 0.000 description 1
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- C07D209/04—Indoles; Hydrogenated indoles
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200702798A ES2331274B1 (es) | 2007-10-25 | 2007-10-25 | Compuesto de indolina. |
| ESP200702798 | 2007-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20100075518A true KR20100075518A (ko) | 2010-07-02 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020107008669A Withdrawn KR20100075518A (ko) | 2007-10-25 | 2008-10-23 | 인돌린 화합물 |
Country Status (16)
| Country | Link |
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| US (1) | US20110112148A1 (enExample) |
| EP (1) | EP2203423A1 (enExample) |
| JP (1) | JP2011500763A (enExample) |
| KR (1) | KR20100075518A (enExample) |
| CN (1) | CN101878200A (enExample) |
| AR (1) | AR069003A1 (enExample) |
| AU (1) | AU2008316472A1 (enExample) |
| BR (1) | BRPI0818850A2 (enExample) |
| CA (1) | CA2703453A1 (enExample) |
| CL (1) | CL2008003139A1 (enExample) |
| ES (1) | ES2331274B1 (enExample) |
| MX (1) | MX2010004463A (enExample) |
| RU (1) | RU2010120847A (enExample) |
| TW (1) | TW200934760A (enExample) |
| UY (1) | UY31423A1 (enExample) |
| WO (1) | WO2009053440A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102942516B (zh) * | 2012-11-05 | 2015-02-25 | 宁波大学 | 一种生物碱类化合物及其制备方法和应用 |
| CN103044310B (zh) * | 2013-01-18 | 2015-02-04 | 贵阳医学院 | 二氢吲哚-3-乙酸衍生物、其制备方法以及在药物中的应用 |
| EP3405454B1 (en) * | 2016-01-21 | 2021-12-29 | Yissum Research Development Company of The Hebrew University of Jerusalem Ltd. | Indoline derivatives, compositions comprising them and uses thereof |
| AR121842A1 (es) * | 2020-04-15 | 2022-07-13 | Ache Laboratorios Farmaceuticos Sa | Compuesto de benzimidazol para el tratamiento de trastornos metabólicos |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2680366B1 (fr) * | 1991-08-13 | 1995-01-20 | Adir | Nouveaux derives d'arylethylamines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| GB9326192D0 (en) * | 1993-12-22 | 1994-02-23 | Glaxo Group Ltd | Chemical compounds |
| CA2186412A1 (en) * | 1995-10-31 | 1997-05-01 | Katherine S. Takaki | Ethylamino carbazole melatonergic agents |
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2007
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2008
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- 2008-10-23 JP JP2010530462A patent/JP2011500763A/ja not_active Abandoned
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- 2008-10-23 CN CN200880118151XA patent/CN101878200A/zh active Pending
- 2008-10-23 US US12/739,666 patent/US20110112148A1/en not_active Abandoned
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- 2008-10-23 EP EP08842562A patent/EP2203423A1/en not_active Withdrawn
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- 2008-10-23 RU RU2010120847/04A patent/RU2010120847A/ru not_active Application Discontinuation
- 2008-10-23 AU AU2008316472A patent/AU2008316472A1/en not_active Abandoned
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- 2008-10-24 CL CL2008003139A patent/CL2008003139A1/es unknown
- 2008-10-24 UY UY31423A patent/UY31423A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2010120847A (ru) | 2011-11-27 |
| MX2010004463A (es) | 2010-05-03 |
| EP2203423A1 (en) | 2010-07-07 |
| AR069003A1 (es) | 2009-12-23 |
| TW200934760A (en) | 2009-08-16 |
| UY31423A1 (es) | 2009-04-30 |
| CN101878200A (zh) | 2010-11-03 |
| CL2008003139A1 (es) | 2009-03-06 |
| AU2008316472A1 (en) | 2009-04-30 |
| WO2009053440A1 (en) | 2009-04-30 |
| ES2331274B1 (es) | 2010-10-21 |
| ES2331274A1 (es) | 2009-12-28 |
| US20110112148A1 (en) | 2011-05-12 |
| JP2011500763A (ja) | 2011-01-06 |
| BRPI0818850A2 (pt) | 2019-09-24 |
| CA2703453A1 (en) | 2009-04-30 |
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