CA2462142A1 - Benzisothiazolyl-substituted aminomethyl chromanes for treating diseases of the central nervous system - Google Patents
Benzisothiazolyl-substituted aminomethyl chromanes for treating diseases of the central nervous system Download PDFInfo
- Publication number
- CA2462142A1 CA2462142A1 CA002462142A CA2462142A CA2462142A1 CA 2462142 A1 CA2462142 A1 CA 2462142A1 CA 002462142 A CA002462142 A CA 002462142A CA 2462142 A CA2462142 A CA 2462142A CA 2462142 A1 CA2462142 A1 CA 2462142A1
- Authority
- CA
- Canada
- Prior art keywords
- mmol
- dihydro
- mixture
- chromen
- 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.)
- Abandoned
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract description 10
- 210000003169 central nervous system Anatomy 0.000 title abstract description 6
- 201000010099 disease Diseases 0.000 title abstract description 3
- -1 Benzisothiazolyl-substituted aminomethyl chromanes Chemical class 0.000 title description 9
- 239000003814 drug Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 10
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 2
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical group C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 150000001843 chromanes Chemical class 0.000 abstract 1
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- 239000000203 mixture Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 31
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- WLLIXJBWWFGEHT-UHFFFAOYSA-N [tert-butyl(dimethyl)silyl] trifluoromethanesulfonate Chemical compound CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F WLLIXJBWWFGEHT-UHFFFAOYSA-N 0.000 description 1
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- RBIGRACRIIVDDP-AREMUKBSSA-N benzyl n-[[(2r)-6-acetyl-3,4-dihydro-2h-chromen-2-yl]methyl]-n-[4-(1,1,3-trioxo-1,2-benzothiazol-2-yl)butyl]carbamate Chemical compound C([C@@H]1OC2=CC=C(C=C2CC1)C(=O)C)N(CCCCN1S(C2=CC=CC=C2C1=O)(=O)=O)C(=O)OCC1=CC=CC=C1 RBIGRACRIIVDDP-AREMUKBSSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
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- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- GRPGDBKIWXIPHM-MRXNPFEDSA-N ethyl (2r)-6-methoxy-7-phenylmethoxy-3,4-dihydro-2h-chromene-2-carboxylate Chemical compound C([C@@H](OC1=C2)C(=O)OCC)CC1=CC(OC)=C2OCC1=CC=CC=C1 GRPGDBKIWXIPHM-MRXNPFEDSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 210000001320 hippocampus Anatomy 0.000 description 1
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- 201000006417 multiple sclerosis Diseases 0.000 description 1
- IRZXLQJVOAQNAO-UHFFFAOYSA-N n-benzyl-1-[4-[tert-butyl(dimethyl)silyl]oxy-3,4-dihydro-2h-chromen-2-yl]methanamine Chemical compound O1C2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)CC1CNCC1=CC=CC=C1 IRZXLQJVOAQNAO-UHFFFAOYSA-N 0.000 description 1
- BHAGEKGIBBDSFZ-UHFFFAOYSA-N n-benzyl-4-[tert-butyl(dimethyl)silyl]oxy-3,4-dihydro-2h-chromene-2-carboxamide Chemical compound O1C2=CC=CC=C2C(O[Si](C)(C)C(C)(C)C)CC1C(=O)NCC1=CC=CC=C1 BHAGEKGIBBDSFZ-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
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- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- YGYBFMRFXNDIPO-QGZVFWFLSA-N repinotan Chemical class O=S1(=O)C2=CC=CC=C2C(=O)N1CCCCNC[C@@H]1OC2=CC=CC=C2CC1 YGYBFMRFXNDIPO-QGZVFWFLSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000002295 serotoninergic effect Effects 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002739 subcortical effect Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10148425.9 | 2001-10-01 | ||
| DE10148425A DE10148425A1 (de) | 2001-10-01 | 2001-10-01 | Chromane |
| PCT/EP2002/010447 WO2003029250A1 (de) | 2001-10-01 | 2002-09-18 | Benzisothiazolyl-substituerte aminomethylcromane zur behandlung von erkrankungen des zentralen nervensystems |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2462142A1 true CA2462142A1 (en) | 2003-04-10 |
Family
ID=7700998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002462142A Abandoned CA2462142A1 (en) | 2001-10-01 | 2002-09-18 | Benzisothiazolyl-substituted aminomethyl chromanes for treating diseases of the central nervous system |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6919360B2 (https=) |
| EP (1) | EP1434777A1 (https=) |
| JP (1) | JP2005507901A (https=) |
| CA (1) | CA2462142A1 (https=) |
| DE (1) | DE10148425A1 (https=) |
| WO (1) | WO2003029250A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2199086B1 (es) | 2002-07-31 | 2005-06-01 | Cepa Schwarz Pharma Sl | Nuevos derivados de cicloalcanodionas, procedimiento para su preparacion y sus aplicaciones farmacologicas. |
| ES2238015B1 (es) * | 2004-01-30 | 2006-11-01 | Cepa Schwarz Pharma, S.L. | Derivados de cicloalcanodionas con actividad neuroprotectora. |
| EP1856126A2 (en) * | 2005-02-17 | 2007-11-21 | Wyeth a Corporation of the State of Delaware | Cycloalkylfused indole, benzothiophene, benzofuran and indene derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3901814A1 (de) | 1988-07-28 | 1990-02-01 | Bayer Ag | Substituierte aminomethylzetraline sowie ihre heterocyclischen analoga |
| DE19522088A1 (de) * | 1995-06-19 | 1997-01-02 | Bayer Ag | Benzisothiazolyl-substituierte Aminomethylchromane |
| DE19543476A1 (de) * | 1995-11-22 | 1997-05-28 | Troponwerke Gmbh & Co Kg | Verwendung von substituierten Aminomethyl-chromanen zur Behandlung von Schädel-Hirn-Trauma |
-
2001
- 2001-10-01 DE DE10148425A patent/DE10148425A1/de not_active Withdrawn
-
2002
- 2002-09-18 EP EP02767489A patent/EP1434777A1/de not_active Withdrawn
- 2002-09-18 JP JP2003532498A patent/JP2005507901A/ja not_active Withdrawn
- 2002-09-18 WO PCT/EP2002/010447 patent/WO2003029250A1/de not_active Ceased
- 2002-09-18 US US10/490,315 patent/US6919360B2/en not_active Expired - Fee Related
- 2002-09-18 CA CA002462142A patent/CA2462142A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE10148425A1 (de) | 2003-04-17 |
| US6919360B2 (en) | 2005-07-19 |
| JP2005507901A (ja) | 2005-03-24 |
| US20040259924A1 (en) | 2004-12-23 |
| WO2003029250A1 (de) | 2003-04-10 |
| EP1434777A1 (de) | 2004-07-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |