CS249191A3 - 1-(pyridinylalkyl)-1h-indoles, indolines and related analogs, process of their preparation and pharmaceuticals comprising them - Google Patents
1-(pyridinylalkyl)-1h-indoles, indolines and related analogs, process of their preparation and pharmaceuticals comprising them Download PDFInfo
- Publication number
- CS249191A3 CS249191A3 CS912491A CS249191A CS249191A3 CS 249191 A3 CS249191 A3 CS 249191A3 CS 912491 A CS912491 A CS 912491A CS 249191 A CS249191 A CS 249191A CS 249191 A3 CS249191 A3 CS 249191A3
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- formula
- indole
- pyridinylmethyl
- lower alkyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000002476 indolines Chemical class 0.000 title description 4
- 239000003814 drug Substances 0.000 title 1
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- -1 nitro, amino Chemical group 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
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- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 3
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- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- NHZIVCMHWXXFDA-UHFFFAOYSA-N 1-(pyridin-4-ylmethyl)indol-5-ol Chemical compound C1=CC2=CC(O)=CC=C2N1CC1=CC=NC=C1 NHZIVCMHWXXFDA-UHFFFAOYSA-N 0.000 claims description 5
- SMUOMHZNGDJUDJ-UHFFFAOYSA-N 5-phenylmethoxy-1-(pyridin-4-ylmethyl)indole Chemical compound C=1C=CC=CC=1COC(C=C1C=C2)=CC=C1N2CC1=CC=NC=C1 SMUOMHZNGDJUDJ-UHFFFAOYSA-N 0.000 claims description 5
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- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000001638 cerebellum Anatomy 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 229940048961 cholinesterase Drugs 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RBLWMQWAHONKNC-UHFFFAOYSA-N hydroxyazanium Chemical compound O[NH3+] RBLWMQWAHONKNC-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000005855 radiation 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
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000012773 waffles Nutrition 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Classifications
-
- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P25/28—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Display Devices Of Pinball Game Machines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56657590A | 1990-08-13 | 1990-08-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS249191A3 true CS249191A3 (en) | 1992-03-18 |
Family
ID=24263468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS912491A CS249191A3 (en) | 1990-08-13 | 1991-08-12 | 1-(pyridinylalkyl)-1h-indoles, indolines and related analogs, process of their preparation and pharmaceuticals comprising them |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0471296B1 (de) |
| JP (1) | JP3057828B2 (de) |
| KR (1) | KR100223133B1 (de) |
| AT (1) | ATE130002T1 (de) |
| AU (1) | AU637249B2 (de) |
| CA (1) | CA2048980C (de) |
| CS (1) | CS249191A3 (de) |
| DE (1) | DE69114404T2 (de) |
| DK (1) | DK0471296T3 (de) |
| ES (1) | ES2079530T3 (de) |
| FI (1) | FI103341B (de) |
| GR (1) | GR3018187T3 (de) |
| HU (1) | HUT58722A (de) |
| IE (1) | IE70596B1 (de) |
| IL (1) | IL99168A (de) |
| MX (1) | MX9100638A (de) |
| NO (1) | NO179583C (de) |
| NZ (2) | NZ260632A (de) |
| PL (1) | PL291408A1 (de) |
| ZA (1) | ZA916341B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5068234A (en) * | 1990-02-26 | 1991-11-26 | Sterling Drug Inc. | 3-arylcarbonyl-1-(c-attached-n-heteryl)-1h-indoles |
| DE69114210T2 (de) * | 1990-08-13 | 1996-05-02 | Hoechst Roussel Pharma | Carbamoyl-1-(pyridinylalkyl)-1H-indole, -indoline und verwandte Verbindungen. |
| FR2674522B1 (fr) * | 1991-03-26 | 1993-07-16 | Lipha | Nouveaux derives de l'indole, procedes de preparation et medicaments les contenant. |
| WO2003087087A2 (en) * | 2002-04-09 | 2003-10-23 | Astex Technology Limited | Heterocyclic compounds and their use as modulators of p38 map kinase |
-
1991
- 1991-08-08 AT AT91113333T patent/ATE130002T1/de not_active IP Right Cessation
- 1991-08-08 DE DE69114404T patent/DE69114404T2/de not_active Expired - Fee Related
- 1991-08-08 EP EP91113333A patent/EP0471296B1/de not_active Expired - Lifetime
- 1991-08-08 DK DK91113333.8T patent/DK0471296T3/da active
- 1991-08-08 ES ES91113333T patent/ES2079530T3/es not_active Expired - Lifetime
- 1991-08-09 NZ NZ260632A patent/NZ260632A/en unknown
- 1991-08-09 FI FI913799A patent/FI103341B/fi active
- 1991-08-09 NZ NZ239328A patent/NZ239328A/en unknown
- 1991-08-12 HU HU912674A patent/HUT58722A/hu unknown
- 1991-08-12 CA CA002048980A patent/CA2048980C/en not_active Expired - Fee Related
- 1991-08-12 IE IE285091A patent/IE70596B1/en not_active IP Right Cessation
- 1991-08-12 IL IL9916891A patent/IL99168A/en unknown
- 1991-08-12 CS CS912491A patent/CS249191A3/cs unknown
- 1991-08-12 KR KR1019910013849A patent/KR100223133B1/ko not_active Expired - Fee Related
- 1991-08-12 PL PL29140891A patent/PL291408A1/xx unknown
- 1991-08-12 ZA ZA916341A patent/ZA916341B/xx unknown
- 1991-08-12 JP JP3201711A patent/JP3057828B2/ja not_active Expired - Fee Related
- 1991-08-12 AU AU81767/91A patent/AU637249B2/en not_active Ceased
- 1991-08-12 MX MX9100638A patent/MX9100638A/es not_active IP Right Cessation
- 1991-08-12 NO NO913140A patent/NO179583C/no unknown
-
1995
- 1995-11-22 GR GR950403313T patent/GR3018187T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE130002T1 (de) | 1995-11-15 |
| JPH05132481A (ja) | 1993-05-28 |
| EP0471296A1 (de) | 1992-02-19 |
| ZA916341B (en) | 1992-04-29 |
| FI913799A7 (fi) | 1992-02-14 |
| FI103341B1 (fi) | 1999-06-15 |
| PL291408A1 (en) | 1992-12-28 |
| KR920004379A (ko) | 1992-03-27 |
| AU8176791A (en) | 1992-02-20 |
| FI103341B (fi) | 1999-06-15 |
| DK0471296T3 (da) | 1996-03-11 |
| NO179583C (no) | 1996-11-06 |
| DE69114404T2 (de) | 1996-05-02 |
| HU912674D0 (en) | 1992-01-28 |
| NZ260632A (en) | 1997-06-24 |
| NZ239328A (en) | 1996-03-26 |
| IL99168A (en) | 1995-07-31 |
| NO913140L (no) | 1992-02-14 |
| IE70596B1 (en) | 1996-12-11 |
| ES2079530T3 (es) | 1996-01-16 |
| JP3057828B2 (ja) | 2000-07-04 |
| GR3018187T3 (en) | 1996-02-29 |
| MX9100638A (es) | 1992-04-01 |
| EP0471296B1 (de) | 1995-11-08 |
| DE69114404D1 (de) | 1995-12-14 |
| NO179583B (no) | 1996-07-29 |
| AU637249B2 (en) | 1993-05-20 |
| KR100223133B1 (ko) | 1999-10-15 |
| IL99168A0 (en) | 1992-07-15 |
| IE912850A1 (en) | 1992-02-26 |
| NO913140D0 (no) | 1991-08-12 |
| CA2048980C (en) | 2003-05-13 |
| FI913799A0 (fi) | 1991-08-09 |
| CA2048980A1 (en) | 1992-02-14 |
| HUT58722A (en) | 1992-03-30 |
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