ES2331274B1 - Compuesto de indolina. - Google Patents
Compuesto de indolina. Download PDFInfo
- Publication number
- ES2331274B1 ES2331274B1 ES200702798A ES200702798A ES2331274B1 ES 2331274 B1 ES2331274 B1 ES 2331274B1 ES 200702798 A ES200702798 A ES 200702798A ES 200702798 A ES200702798 A ES 200702798A ES 2331274 B1 ES2331274 B1 ES 2331274B1
- Authority
- ES
- Spain
- Prior art keywords
- dihydro
- ethyl
- acetamide
- indol
- indole
- 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- Withdrawn - After Issue
Links
- -1 INDOLINE COMPOUND Chemical class 0.000 title description 11
- 230000001193 melatoninergic effect Effects 0.000 claims abstract description 13
- 230000002265 prevention Effects 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 37
- 230000004075 alteration Effects 0.000 claims description 22
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 16
- 206010022437 insomnia Diseases 0.000 claims description 16
- 230000007170 pathology Effects 0.000 claims description 14
- 150000002476 indolines Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 8
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 8
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 208000000044 Amnesia Diseases 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 208000019695 Migraine disease Diseases 0.000 claims description 6
- 208000008589 Obesity Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 208000028017 Psychotic disease Diseases 0.000 claims description 6
- 230000032683 aging Effects 0.000 claims description 6
- 230000036506 anxiety Effects 0.000 claims description 6
- 230000036528 appetite Effects 0.000 claims description 6
- 235000019789 appetite Nutrition 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 6
- 206010027599 migraine Diseases 0.000 claims description 6
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- 208000026139 Memory disease Diseases 0.000 claims description 5
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 208000019116 sleep disease Diseases 0.000 claims description 4
- 208000022925 sleep disturbance Diseases 0.000 claims description 3
- 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 description 2
- 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 description 2
- PWBULZJYQSUOIV-UHFFFAOYSA-N 1-[2-[6-(3-phenylpropoxy)-2,3-dihydroindol-1-yl]ethyl]cyclopropane-1-carboxamide Chemical compound C1CC2=CC=C(OCCCC=3C=CC=CC=3)C=C2N1CCC1(C(=O)N)CC1 PWBULZJYQSUOIV-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 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 description 2
- 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 claims description 2
- 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 description 2
- BTDOHXZTYNXNBL-UHFFFAOYSA-N n-[2-(6-methoxy-2,3-dihydroindol-1-yl)propyl]acetamide Chemical compound COC1=CC=C2CCN(C(C)CNC(C)=O)C2=C1 BTDOHXZTYNXNBL-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- TVOQLWJVRZIPPM-UHFFFAOYSA-N n-[2-[6-(3-phenylpropoxy)-2,3-dihydroindol-1-yl]ethyl]acetamide Chemical compound C1=C2N(CCNC(=O)C)CCC2=CC=C1OCCCC1=CC=CC=C1 TVOQLWJVRZIPPM-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 1
- 239000000203 mixture Substances 0.000 abstract description 6
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
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- 238000000034 method Methods 0.000 description 14
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 9
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- 229960003987 melatonin Drugs 0.000 description 9
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 8
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- 238000006243 chemical reaction Methods 0.000 description 7
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- 102100024930 Melatonin receptor type 1A Human genes 0.000 description 6
- 101710098568 Melatonin receptor type 1A Proteins 0.000 description 6
- 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
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- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 6
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- YLXDSYKOBKBWJQ-LBPRGKRZSA-N N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e]benzofuran-8-yl]ethyl]propanamide Chemical compound C1=C2OCCC2=C2[C@H](CCNC(=O)CC)CCC2=C1 YLXDSYKOBKBWJQ-LBPRGKRZSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- 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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- 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
- C07D401/04—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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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Cardiology (AREA)
- Anesthesiology (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200702798A ES2331274B1 (es) | 2007-10-25 | 2007-10-25 | Compuesto de indolina. |
| MX2010004463A MX2010004463A (es) | 2007-10-25 | 2008-10-23 | Compuestos de indolina. |
| RU2010120847/04A RU2010120847A (ru) | 2007-10-25 | 2008-10-23 | Соединения индолина, фармацевтическая композиция на их основе и способ лечения или профилактики мелатонинергических заболеваний |
| ARP080104617A AR069003A1 (es) | 2007-10-25 | 2008-10-23 | Compuestos de indolina, sus usos en la preparacion de medicamentos y sus usos para el tratamiento de alteraciones melatoninergicas, composiciones farmaceuticas que los comprende y uso de la composicion farmaceutica para preparar un medicamento |
| BRPI0818850A BRPI0818850A2 (pt) | 2007-10-25 | 2008-10-23 | compostos de indolina, uso dos referidos compostos, composição farmacêutica compreendendo os mesmos e uso da referida composição farmacêutica. |
| PCT/EP2008/064389 WO2009053440A1 (en) | 2007-10-25 | 2008-10-23 | Indoline compounds |
| KR1020107008669A KR20100075518A (ko) | 2007-10-25 | 2008-10-23 | 인돌린 화합물 |
| US12/739,666 US20110112148A1 (en) | 2007-10-25 | 2008-10-23 | Indoline compounds |
| AU2008316472A AU2008316472A1 (en) | 2007-10-25 | 2008-10-23 | Indoline compounds |
| CN200880118151XA CN101878200A (zh) | 2007-10-25 | 2008-10-23 | 二氢吲哚化合物 |
| CA2703453A CA2703453A1 (en) | 2007-10-25 | 2008-10-23 | Indoline compounds |
| EP08842562A EP2203423A1 (en) | 2007-10-25 | 2008-10-23 | Indoline compounds |
| JP2010530462A JP2011500763A (ja) | 2007-10-25 | 2008-10-23 | インドリン化合物 |
| CL2008003139A CL2008003139A1 (es) | 2007-10-25 | 2008-10-24 | Compuestos derivados de 6-(alcoxi o fenilalcoxi)-2,3-dihidro-indol-1-il-alquilaminas aciladas, con actividad en los receptores mt1 y mt2; composicion farmaceutica que los comprende; y uso en el tratamiento de alteraciones melatoninergicas tales como depresion, alteraciones del sueño y enfermedad de alzheimer. |
| TW097140812A TW200934760A (en) | 2007-10-25 | 2008-10-24 | Indoline compounds |
| UY31423A UY31423A1 (es) | 2007-10-25 | 2008-10-24 | Compuestos de indolina |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200702798A ES2331274B1 (es) | 2007-10-25 | 2007-10-25 | Compuesto de indolina. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2331274A1 ES2331274A1 (es) | 2009-12-28 |
| ES2331274B1 true ES2331274B1 (es) | 2010-10-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200702798A Withdrawn - After Issue ES2331274B1 (es) | 2007-10-25 | 2007-10-25 | Compuesto de indolina. |
Country Status (16)
| Country | Link |
|---|---|
| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5276051A (en) * | 1991-08-13 | 1994-01-04 | Adir Et Compagnie | Arylethylamine compounds |
| WO1995017405A1 (en) * | 1993-12-22 | 1995-06-29 | Glaxo Group Limited | Indoline derivatives, method of preparation and their use as pharmaceuticals |
| US5677328A (en) * | 1995-10-31 | 1997-10-14 | Bristol-Myers Squibb Company | Ethylamino carbazole melatonergic agents |
-
2007
- 2007-10-25 ES ES200702798A patent/ES2331274B1/es not_active Withdrawn - After Issue
-
2008
- 2008-10-23 KR KR1020107008669A patent/KR20100075518A/ko not_active Withdrawn
- 2008-10-23 CA CA2703453A patent/CA2703453A1/en not_active Abandoned
- 2008-10-23 JP JP2010530462A patent/JP2011500763A/ja not_active Abandoned
- 2008-10-23 WO PCT/EP2008/064389 patent/WO2009053440A1/en not_active Ceased
- 2008-10-23 MX MX2010004463A patent/MX2010004463A/es active IP Right Grant
- 2008-10-23 CN CN200880118151XA patent/CN101878200A/zh active Pending
- 2008-10-23 US US12/739,666 patent/US20110112148A1/en not_active Abandoned
- 2008-10-23 AR ARP080104617A patent/AR069003A1/es not_active Application Discontinuation
- 2008-10-23 EP EP08842562A patent/EP2203423A1/en not_active Withdrawn
- 2008-10-23 BR BRPI0818850A patent/BRPI0818850A2/pt not_active IP Right Cessation
- 2008-10-23 RU RU2010120847/04A patent/RU2010120847A/ru not_active Application Discontinuation
- 2008-10-23 AU AU2008316472A patent/AU2008316472A1/en not_active Abandoned
- 2008-10-24 TW TW097140812A patent/TW200934760A/zh unknown
- 2008-10-24 CL CL2008003139A patent/CL2008003139A1/es unknown
- 2008-10-24 UY UY31423A patent/UY31423A1/es unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5276051A (en) * | 1991-08-13 | 1994-01-04 | Adir Et Compagnie | Arylethylamine compounds |
| WO1995017405A1 (en) * | 1993-12-22 | 1995-06-29 | Glaxo Group Limited | Indoline derivatives, method of preparation and their use as pharmaceuticals |
| US5677328A (en) * | 1995-10-31 | 1997-10-14 | Bristol-Myers Squibb Company | Ethylamino carbazole melatonergic agents |
Non-Patent Citations (1)
| Title |
|---|
| ATTIA, M.I. et al.: "{}Synthesis and pharmacological evaluation of 6a,7 dihydro-6H, 13 H, pyrazino (1,2-a; 4,5-a')diindole analogs as melatoni receptor ligands"{}. Tetrahedron, 2007, vol. 63, 15 enero, páginas 754-760, todo el documento. * |
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 |
| ES2331274A1 (es) | 2009-12-28 |
| US20110112148A1 (en) | 2011-05-12 |
| JP2011500763A (ja) | 2011-01-06 |
| BRPI0818850A2 (pt) | 2019-09-24 |
| KR20100075518A (ko) | 2010-07-02 |
| CA2703453A1 (en) | 2009-04-30 |
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