CA2350089A1 - Indole derivatives - Google Patents
Indole derivatives Download PDFInfo
- Publication number
- CA2350089A1 CA2350089A1 CA002350089A CA2350089A CA2350089A1 CA 2350089 A1 CA2350089 A1 CA 2350089A1 CA 002350089 A CA002350089 A CA 002350089A CA 2350089 A CA2350089 A CA 2350089A CA 2350089 A1 CA2350089 A1 CA 2350089A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- aryl
- nr5r6
- useful
- disorders
- 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.)
- Granted
Links
- 150000002475 indoles Chemical class 0.000 title abstract 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract 2
- 208000019901 Anxiety disease Diseases 0.000 abstract 1
- 206010009094 Chronic paroxysmal hemicrania Diseases 0.000 abstract 1
- 208000006561 Cluster Headache Diseases 0.000 abstract 1
- 208000020401 Depressive disease Diseases 0.000 abstract 1
- 206010013654 Drug abuse Diseases 0.000 abstract 1
- 208000030814 Eating disease Diseases 0.000 abstract 1
- 208000019454 Feeding and Eating disease Diseases 0.000 abstract 1
- 206010019233 Headaches Diseases 0.000 abstract 1
- 208000019695 Migraine disease Diseases 0.000 abstract 1
- 208000008589 Obesity Diseases 0.000 abstract 1
- 208000002193 Pain Diseases 0.000 abstract 1
- 239000000556 agonist Substances 0.000 abstract 1
- 230000036506 anxiety Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 208000018912 cluster headache syndrome Diseases 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000002950 deficient Effects 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 235000014632 disordered eating Nutrition 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 231100000869 headache Toxicity 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 206010027599 migraine Diseases 0.000 abstract 1
- 235000020824 obesity Nutrition 0.000 abstract 1
- 208000007777 paroxysmal Hemicrania Diseases 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 230000000862 serotonergic effect Effects 0.000 abstract 1
- 229940076279 serotonin Drugs 0.000 abstract 1
- 208000011117 substance-related disease Diseases 0.000 abstract 1
- 230000005062 synaptic transmission Effects 0.000 abstract 1
- 208000019553 vascular disease Diseases 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Disclosed are indole compounds of the formula:
(wherein n is 0, 1, or 2; X is Cl, Br, or I; Q is CH2 or CO; W
is -CO2R11 or R3; R1 is H; R2 is halo, CN, -OR4, -(CH2)m-(C=O)NR5R6, -(CH2)m-SO2NR5R6, -(CH2)m-NR7(C=O)R8, -(CH2)m-NR7SO2R8, -(CH2)m-S(O)x R8, -(CH2)m-NR7(C=O)NR5R6, -(CH2)m-NR7(C=O)OR9, and -CH=CH(CH2)y R10; R3 is H or alkyl; R4 is H, alkyl or aryl; R5 and R6 are H, alkyl or aryl or together form a ring; R7, R8 and R9 are H, alkyl, aryl or aralkyl; R10 is -CONR5R6 or the like; and R11 is alkyl, benzyl or aryl). These compounds are useful as intermediates for producing indole compounds that are useful as psychotherapeutics and are potent serotonin (5-HT1) agonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain, chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission.
(wherein n is 0, 1, or 2; X is Cl, Br, or I; Q is CH2 or CO; W
is -CO2R11 or R3; R1 is H; R2 is halo, CN, -OR4, -(CH2)m-(C=O)NR5R6, -(CH2)m-SO2NR5R6, -(CH2)m-NR7(C=O)R8, -(CH2)m-NR7SO2R8, -(CH2)m-S(O)x R8, -(CH2)m-NR7(C=O)NR5R6, -(CH2)m-NR7(C=O)OR9, and -CH=CH(CH2)y R10; R3 is H or alkyl; R4 is H, alkyl or aryl; R5 and R6 are H, alkyl or aryl or together form a ring; R7, R8 and R9 are H, alkyl, aryl or aralkyl; R10 is -CONR5R6 or the like; and R11 is alkyl, benzyl or aryl). These compounds are useful as intermediates for producing indole compounds that are useful as psychotherapeutics and are potent serotonin (5-HT1) agonists and may be used in the treatment of depression, anxiety, eating disorders, obesity, drug abuse, cluster headache, migraine, pain, chronic paroxysmal hemicrania and headache associated with vascular disorders, and other disorders arising from deficient serotonergic neurotransmission.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/469,258 US5578612A (en) | 1990-10-15 | 1995-06-06 | Indole derivatives |
| US08/469,258 | 1995-06-06 | ||
| CA002178161A CA2178161C (en) | 1995-06-06 | 1996-06-04 | Indole derivatives |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002178161A Division CA2178161C (en) | 1995-06-06 | 1996-06-04 | Indole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2350089A1 true CA2350089A1 (en) | 1996-12-07 |
| CA2350089C CA2350089C (en) | 2004-07-27 |
Family
ID=25678497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002350089A Expired - Lifetime CA2350089C (en) | 1995-06-06 | 1996-06-04 | Indole derivatives |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2350089C (en) |
-
1996
- 1996-06-04 CA CA002350089A patent/CA2350089C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2350089C (en) | 2004-07-27 |
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| EG20416A (en) | Process for preparing of indole derivatives and their use in treating migraine | |
| DE69301357D1 (en) | INDOL DERIVATIVES AS "5-HT1-LIKE" AGONISTS | |
| CA2350089A1 (en) | Indole derivatives | |
| ES2070772A1 (en) | Acylaminoindole derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20160606 |