DE3338753A1 - Heterocyclische aminoverbindungen und verfahren zu ihrer herstellung - Google Patents
Heterocyclische aminoverbindungen und verfahren zu ihrer herstellungInfo
- Publication number
- DE3338753A1 DE3338753A1 DE19833338753 DE3338753A DE3338753A1 DE 3338753 A1 DE3338753 A1 DE 3338753A1 DE 19833338753 DE19833338753 DE 19833338753 DE 3338753 A DE3338753 A DE 3338753A DE 3338753 A1 DE3338753 A1 DE 3338753A1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- general formula
- group
- trans
- solution
- 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.)
- Ceased
Links
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- 238000004519 manufacturing process Methods 0.000 title claims description 6
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
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- 239000002904 solvent Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
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- 239000003054 catalyst Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
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- 239000004480 active ingredient Substances 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
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- 239000002244 precipitate Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 239000003643 water by type Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
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- 125000005002 aryl methyl group Chemical group 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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- 125000003342 alkenyl group Chemical group 0.000 description 4
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- 229960002896 clonidine Drugs 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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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
- C07D491/02—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 two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- C07D491/02—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 two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Endocrinology (AREA)
- Anesthesiology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8230379 | 1982-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3338753A1 true DE3338753A1 (de) | 1984-04-26 |
Family
ID=10533819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833338753 Ceased DE3338753A1 (de) | 1982-10-25 | 1983-10-25 | Heterocyclische aminoverbindungen und verfahren zu ihrer herstellung |
Country Status (18)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8410459D0 (en) * | 1984-04-24 | 1984-05-31 | Glaxo Group Ltd | Chemical compounds |
| DE3579189D1 (de) * | 1984-04-24 | 1990-09-20 | Glaxo Group Ltd | Heterocyclische aminoverbindungen. |
| GB8526210D0 (en) * | 1985-10-23 | 1985-11-27 | Glaxo Group Ltd | Chemical compounds |
| US4769367A (en) * | 1984-04-24 | 1988-09-06 | Glaxo Group Limited | Heterocyclic amino compounds |
| GB8526209D0 (en) * | 1985-10-23 | 1985-11-27 | Glaxo Group Ltd | Chemical process |
| US5225431A (en) * | 1987-10-23 | 1993-07-06 | Burroughs Wellcome Co. | Therapeutic substituted indole compounds and compositions thereof |
| GB8828032D0 (en) * | 1988-12-01 | 1989-01-05 | Glaxo Group Ltd | Medicaments |
| DE10107243A1 (de) * | 2001-02-16 | 2002-08-22 | Bayer Ag | Benzodioxinopyrrole, deren Herstellung und Verwendung |
| US8099200B2 (en) | 2005-09-30 | 2012-01-17 | Coombs Joshua D | Vehicle interface based on the weight distribution of a user |
| US20070074922A1 (en) * | 2005-09-30 | 2007-04-05 | Coombs Joshua D | Vehicle interface based on a shift of the torso of a user |
| US20070074921A1 (en) * | 2005-09-30 | 2007-04-05 | Coombs Joshua D | Vehicle interface based on a shift of the appendages of a user |
| US20090076686A1 (en) * | 2005-09-30 | 2009-03-19 | Jeffrey Schox | Vehicle interface to communicate a safety alert mode command |
| US20070078569A1 (en) * | 2005-09-30 | 2007-04-05 | Jeffrey Schox | Vehicle interface to communicate a safety alert mode command |
-
1983
- 1983-10-24 IL IL70034A patent/IL70034A0/xx unknown
- 1983-10-25 US US06/545,191 patent/US4496579A/en not_active Expired - Fee Related
- 1983-10-25 SE SE8305866A patent/SE8305866L/xx not_active Application Discontinuation
- 1983-10-25 BE BE0/211766A patent/BE898072A/fr not_active IP Right Cessation
- 1983-10-25 GB GB08328468A patent/GB2129795B/en not_active Expired
- 1983-10-25 FI FI833887A patent/FI833887A7/fi not_active Application Discontinuation
- 1983-10-25 NL NL8303673A patent/NL8303673A/nl not_active Application Discontinuation
- 1983-10-25 IT IT8349214A patent/IT1212893B/it active
- 1983-10-25 LU LU85059A patent/LU85059A1/fr unknown
- 1983-10-25 FR FR8316989A patent/FR2534921B1/fr not_active Expired
- 1983-10-25 GR GR72780A patent/GR79405B/el unknown
- 1983-10-25 KR KR1019830005035A patent/KR840006486A/ko not_active Withdrawn
- 1983-10-25 DE DE19833338753 patent/DE3338753A1/de not_active Ceased
- 1983-10-25 ZA ZA837921A patent/ZA837921B/xx unknown
- 1983-10-25 ES ES526738A patent/ES526738A0/es active Granted
- 1983-10-25 JP JP58199871A patent/JPS5998086A/ja active Pending
- 1983-10-25 CH CH5771/83A patent/CH661046A5/fr not_active IP Right Cessation
- 1983-10-25 AU AU20552/83A patent/AU2055283A/en not_active Abandoned
Non-Patent Citations (3)
| Title |
|---|
| J. Med. Chem. 20(1977) 880-85 * |
| J. Med. Chem. 9(1965) 446-456 * |
| J. Org. Chem. 39(1974) 1808-11 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FI833887A7 (fi) | 1984-04-26 |
| FR2534921A1 (fr) | 1984-04-27 |
| SE8305866D0 (sv) | 1983-10-25 |
| CH661046A5 (fr) | 1987-06-30 |
| IT1212893B (it) | 1989-11-30 |
| JPS5998086A (ja) | 1984-06-06 |
| ES8504200A1 (es) | 1985-04-16 |
| BE898072A (fr) | 1984-04-25 |
| FR2534921B1 (fr) | 1987-01-16 |
| GB2129795B (en) | 1986-02-12 |
| IL70034A0 (en) | 1984-01-31 |
| LU85059A1 (fr) | 1985-06-19 |
| GR79405B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-10-22 |
| KR840006486A (ko) | 1984-11-30 |
| ES526738A0 (es) | 1985-04-16 |
| ZA837921B (en) | 1985-04-24 |
| NL8303673A (nl) | 1984-05-16 |
| SE8305866L (sv) | 1984-04-26 |
| AU2055283A (en) | 1984-05-03 |
| IT8349214A0 (it) | 1983-10-25 |
| FI833887A0 (fi) | 1983-10-25 |
| GB2129795A (en) | 1984-05-23 |
| GB8328468D0 (en) | 1983-11-23 |
| US4496579A (en) | 1985-01-29 |
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| 8110 | Request for examination paragraph 44 | ||
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