JP4292738B2 - インドール誘導体およびその医薬用途 - Google Patents
インドール誘導体およびその医薬用途 Download PDFInfo
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- JP4292738B2 JP4292738B2 JP2001357400A JP2001357400A JP4292738B2 JP 4292738 B2 JP4292738 B2 JP 4292738B2 JP 2001357400 A JP2001357400 A JP 2001357400A JP 2001357400 A JP2001357400 A JP 2001357400A JP 4292738 B2 JP4292738 B2 JP 4292738B2
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- carbons
- alkyl
- carbon atoms
- hydrogen
- hydroxy
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- 150000002475 indoles Chemical class 0.000 title claims abstract description 16
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 82
- 239000001257 hydrogen Substances 0.000 claims abstract description 82
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 79
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 58
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000003814 drug Substances 0.000 claims abstract description 16
- -1 trifluoro Methoxy, cyano, phenyl Chemical group 0.000 claims description 104
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 51
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000004043 oxo group Chemical group O=* 0.000 claims description 25
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 21
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
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- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 10
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 11
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- 101100244562 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) oprD gene Proteins 0.000 abstract description 14
- 108700023159 delta Opioid Receptors Proteins 0.000 abstract description 14
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- 150000001721 carbon Chemical group 0.000 description 22
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- 239000000203 mixture Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000012153 distilled water Substances 0.000 description 14
- 229910002092 carbon dioxide Inorganic materials 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
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- 239000000047 product Substances 0.000 description 12
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- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 description 9
- OFDNQWIFNXBECV-VFSYNPLYSA-N dolastatin 10 Chemical compound CC(C)[C@H](N(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)[C@H](OC)CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@H](C=1SC=CN=1)CC1=CC=CC=C1 OFDNQWIFNXBECV-VFSYNPLYSA-N 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 229940098779 methanesulfonic acid Drugs 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 235000011054 acetic acid Nutrition 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- 230000000954 anitussive effect Effects 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001357400A JP4292738B2 (ja) | 2000-11-22 | 2001-11-22 | インドール誘導体およびその医薬用途 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000356382 | 2000-11-22 | ||
| JP2000-356382 | 2000-11-22 | ||
| JP2001357400A JP4292738B2 (ja) | 2000-11-22 | 2001-11-22 | インドール誘導体およびその医薬用途 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002220391A JP2002220391A (ja) | 2002-08-09 |
| JP2002220391A5 JP2002220391A5 (enExample) | 2005-06-30 |
| JP4292738B2 true JP4292738B2 (ja) | 2009-07-08 |
Family
ID=18828643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001357400A Expired - Fee Related JP4292738B2 (ja) | 2000-11-22 | 2001-11-22 | インドール誘導体およびその医薬用途 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6770654B2 (enExample) |
| EP (1) | EP1342723B1 (enExample) |
| JP (1) | JP4292738B2 (enExample) |
| KR (1) | KR20030053530A (enExample) |
| CN (1) | CN1247591C (enExample) |
| AT (1) | ATE402179T1 (enExample) |
| AU (2) | AU2408602A (enExample) |
| CA (1) | CA2427931A1 (enExample) |
| DE (1) | DE60135016D1 (enExample) |
| ES (1) | ES2311034T3 (enExample) |
| WO (1) | WO2002042309A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11324742B2 (en) | 2018-03-08 | 2022-05-10 | Victoria Link Ltd. | Treatment of demyelinating diseases |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1424337A1 (en) * | 2002-11-26 | 2004-06-02 | Solvay Pharmaceuticals GmbH | 4-hydroxy derivatives of 5,6,9,10-tetrahydro-10-((2-methyl-1h-imidazol-1-yl)methyl)-4h-pyrido-(3,2,1-jk)-carbazol-11(8h)-one |
| EP1602374A4 (en) * | 2003-03-07 | 2007-03-07 | Toray Industries | MEANS FOR TREATMENT OF MEDICAMENT / SUBSTANCE DEPENDENCE |
| US20060069086A1 (en) * | 2004-09-23 | 2006-03-30 | Alexander Michalow | Methods for regulating neurotransmitter systems by inducing counteradaptations |
| WO2006126529A1 (ja) | 2005-05-25 | 2006-11-30 | Shionogi & Co., Ltd. | ６，７－不飽和－７－カルバモイル置換モルヒナン誘導体 |
| WO2008001859A1 (fr) * | 2006-06-30 | 2008-01-03 | School Juridical Person Kitasato Gakuen | AGONISTE DES RÉCEPTEURS δ DES OPIOÏDES |
| EP2149370A1 (en) | 2008-07-31 | 2010-02-03 | Neuroscienze Pharmaness S.C. A R.L. | Diazabicyclic compounds and microemulsions thereof |
| IT1390848B1 (it) | 2008-07-31 | 2011-10-19 | Neuroscienze Pharmaness S C A R L | Composti farmaceutici |
| IT1396951B1 (it) | 2009-12-18 | 2012-12-20 | Neuroscienze Pharmaness S C A R L | Composti farmaceutici |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2205664C (en) * | 1995-09-26 | 2008-05-20 | Toray Industries, Inc. | Indole derivatives and medicinal use thereof |
-
2001
- 2001-11-22 WO PCT/JP2001/010249 patent/WO2002042309A1/ja not_active Ceased
- 2001-11-22 ES ES01997196T patent/ES2311034T3/es not_active Expired - Lifetime
- 2001-11-22 AU AU2408602A patent/AU2408602A/xx active Pending
- 2001-11-22 CA CA002427931A patent/CA2427931A1/en not_active Abandoned
- 2001-11-22 DE DE60135016T patent/DE60135016D1/de not_active Expired - Fee Related
- 2001-11-22 JP JP2001357400A patent/JP4292738B2/ja not_active Expired - Fee Related
- 2001-11-22 AT AT01997196T patent/ATE402179T1/de not_active IP Right Cessation
- 2001-11-22 CN CNB018221122A patent/CN1247591C/zh not_active Expired - Fee Related
- 2001-11-22 EP EP01997196A patent/EP1342723B1/en not_active Expired - Lifetime
- 2001-11-22 AU AU2002224086A patent/AU2002224086B8/en not_active Ceased
- 2001-11-22 US US10/432,011 patent/US6770654B2/en not_active Expired - Fee Related
- 2001-11-22 KR KR10-2003-7006870A patent/KR20030053530A/ko not_active Ceased
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11324742B2 (en) | 2018-03-08 | 2022-05-10 | Victoria Link Ltd. | Treatment of demyelinating diseases |
| US12318380B2 (en) | 2018-03-08 | 2025-06-03 | Victoria Link Ltd. | Treatment of demyelinating diseases |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2408602A (en) | 2002-06-03 |
| US20040019071A1 (en) | 2004-01-29 |
| KR20030053530A (ko) | 2003-06-28 |
| DE60135016D1 (de) | 2008-09-04 |
| ATE402179T1 (de) | 2008-08-15 |
| WO2002042309A1 (en) | 2002-05-30 |
| CA2427931A1 (en) | 2002-05-30 |
| ES2311034T3 (es) | 2009-02-01 |
| CN1247591C (zh) | 2006-03-29 |
| JP2002220391A (ja) | 2002-08-09 |
| EP1342723A4 (en) | 2005-02-09 |
| US6770654B2 (en) | 2004-08-03 |
| EP1342723A1 (en) | 2003-09-10 |
| AU2002224086B1 (en) | 2006-11-16 |
| EP1342723B1 (en) | 2008-07-23 |
| AU2002224086B8 (en) | 2002-06-03 |
| CN1486321A (zh) | 2004-03-31 |
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