DK169269B1 - Analogifremgangsmåde til fremstilling af 4-(3-trifluormethylphenyl)-1,2,3,6-tetrahydropyridiner - Google Patents
Analogifremgangsmåde til fremstilling af 4-(3-trifluormethylphenyl)-1,2,3,6-tetrahydropyridiner Download PDFInfo
- Publication number
- DK169269B1 DK169269B1 DK371983A DK371983A DK169269B1 DK 169269 B1 DK169269 B1 DK 169269B1 DK 371983 A DK371983 A DK 371983A DK 371983 A DK371983 A DK 371983A DK 169269 B1 DK169269 B1 DK 169269B1
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- DK
- Denmark
- Prior art keywords
- formula
- trifluoromethylphenyl
- group
- carbon atoms
- tetrahydropyridine
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- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- AQXXZDYPVDOQEE-MXDQRGINSA-N Pyrantel pamoate Chemical compound CN1CCCN=C1\C=C\C1=CC=CS1.C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 AQXXZDYPVDOQEE-MXDQRGINSA-N 0.000 description 1
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- 229930006000 Sucrose Natural products 0.000 description 1
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- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
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- 230000026781 habituation Effects 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000008517 inhibition of serotonin uptake Effects 0.000 description 1
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- 231100000053 low toxicity Toxicity 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
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000002474 noradrenergic effect Effects 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 235000006286 nutrient intake Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 231100000316 potential neurotoxicity Toxicity 0.000 description 1
- 230000008307 presynaptic mechanism Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
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- 230000002936 tranquilizing effect Effects 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Obesity (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Photoreceptors In Electrophotography (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8214169 | 1982-08-16 | ||
| FR8214169A FR2531707A1 (fr) | 1982-08-16 | 1982-08-16 | Trifluoromethylphenyltetrahydropyridines substituees a activite anorexigene, un procede de preparation et compositions pharmaceutiques |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK371983D0 DK371983D0 (da) | 1983-08-15 |
| DK371983A DK371983A (da) | 1984-02-17 |
| DK169269B1 true DK169269B1 (da) | 1994-09-26 |
Family
ID=9276890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK371983A DK169269B1 (da) | 1982-08-16 | 1983-08-15 | Analogifremgangsmåde til fremstilling af 4-(3-trifluormethylphenyl)-1,2,3,6-tetrahydropyridiner |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4521428A (fi) |
| EP (1) | EP0101381B1 (fi) |
| JP (1) | JPS5984865A (fi) |
| AT (1) | ATE16805T1 (fi) |
| AU (1) | AU562789B2 (fi) |
| CA (1) | CA1245662A (fi) |
| DE (1) | DE3361424D1 (fi) |
| DK (1) | DK169269B1 (fi) |
| ES (1) | ES8500264A1 (fi) |
| FI (1) | FI73992C (fi) |
| FR (1) | FR2531707A1 (fi) |
| GR (1) | GR78690B (fi) |
| IE (1) | IE55870B1 (fi) |
| IL (1) | IL69348A (fi) |
| NO (1) | NO161855C (fi) |
| NZ (1) | NZ205269A (fi) |
| PT (1) | PT77205B (fi) |
| YU (1) | YU44750B (fi) |
| ZA (1) | ZA835577B (fi) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3438394A1 (de) * | 1984-10-19 | 1986-04-30 | Merck Patent Gmbh, 6100 Darmstadt | Pyridinderivate |
| FR2639226B1 (fr) * | 1988-11-18 | 1993-11-05 | Sanofi | Utilisation de trifluoromethylphenyltetrahydropyridines pour la preparation de medicaments destines a combattre les troubles anxio-depressifs |
| FR2650505B1 (fr) * | 1989-08-07 | 1994-06-03 | Midy Spa | Utilisation de trifluoromethylphenyltetrahydropyridines pour la preparation de medicaments destines a combattre les troubles de la motricite intestinale |
| US5266573A (en) * | 1989-08-07 | 1993-11-30 | Elf Sanofi | Trifluoromethylphenyltetrahydropyridines for the treatment and/or prophylaxis of intestinal motility disorders |
| US5149817A (en) * | 1990-03-05 | 1992-09-22 | Shionogi & Co., Ltd. | Teirahydropyridine derivatives |
| FR2662355B1 (fr) * | 1990-05-22 | 1994-11-10 | Sanofi Sa | Utilisation de la 1-[2-(2-naphtyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine pour la preparation de medicaments destines au traitement de troubles cerebraux et neuronaux. |
| FR2662442A1 (fr) * | 1990-05-23 | 1991-11-29 | Midy Spa | Trifluoromethylphenyltetrahydropyridines n-substituees procede pour leur preparation, intermediaires du procede et compositions pharmaceutiques les contenant. |
| US5618822A (en) * | 1990-05-23 | 1997-04-08 | Sanofi | N-substituted trifluoromethylphenyltetrahydropyridines, process for the preparation thereof, intermediates in said process and pharmaceutical compositions containing them |
| FR2672213B1 (fr) * | 1991-02-05 | 1995-03-10 | Sanofi Sa | Utilisation de derives 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridiniques comme capteurs de radicaux libres. |
| FR2690158B1 (fr) * | 1992-04-17 | 1994-07-22 | Sanofi Elf | Nouveau derive arylpiperidinique, procede pour sa preparation et compositions pharmaceutiques le contenant. |
| FR2757510B1 (fr) * | 1996-12-23 | 2000-01-07 | Sanofi Sa | Forme microparticulaire d'un derive de tetrahydropyridine |
| US6489334B2 (en) | 1996-12-23 | 2002-12-03 | Sanofi-Synthelabo | Method for the crystallization of a tetrahydropyridin derivative and resulting crystalline forms |
| FR2757511B1 (fr) * | 1996-12-23 | 2001-05-04 | Sanofi Sa | Procede pour la preparation d'un derive de tetrahydropyridine |
| FR2757543B1 (fr) * | 1996-12-23 | 1999-04-02 | Sanofi Sa | Procede pour la cristallisation d'un derive de tetrahydropyridine et formes cristallines ainsi obtenues |
| FR2762514B1 (fr) | 1997-04-29 | 1999-10-22 | Sanofi Sa | Utilisation de derives de la tetrahydropyridine pour la preparation de medicaments pour le traitement des maladies entrainant une demyelinisation |
| FR2763847B1 (fr) | 1997-05-28 | 2003-06-06 | Sanofi Sa | Utilisation de tetrahydropyridines 4-substituees pour fabriquer des medicaments agissant sur le tgf-beta-1 |
| WO2002012191A1 (fr) * | 2000-08-08 | 2002-02-14 | Shionogi & Co., Ltd. | Derives d'amines cycliques et utilisation |
| AU2012318528A1 (en) | 2011-10-07 | 2014-05-22 | Boral Ip Holdings (Australia) Pty Limited | Inorganic polymer/organic polymer composites and methods of making same |
| WO2016022103A1 (en) | 2014-08-05 | 2016-02-11 | Amitabha Kumar | Filled polymeric composites including short length fibers |
| US9988512B2 (en) | 2015-01-22 | 2018-06-05 | Boral Ip Holdings (Australia) Pty Limited | Highly filled polyurethane composites |
| WO2016195717A1 (en) | 2015-06-05 | 2016-12-08 | Boral Ip Holdings (Australia) Pty Limited | Filled polyurethane composites with lightweight fillers |
| US20170267585A1 (en) | 2015-11-12 | 2017-09-21 | Amitabha Kumar | Filled polyurethane composites with size-graded fillers |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB948071A (en) * | 1959-05-01 | 1964-01-29 | May & Baker Ltd | New heterocyclic compounds |
| FR86403E (fr) * | 1959-05-01 | 1966-02-04 | May & Baker Ltd | Nouveaux dérivés de la phényl-4 pipéridine et leur préparation |
| GB984364A (en) * | 1961-07-28 | 1965-02-24 | May & Baker Ltd | Substituted piperidines and tetrahydropyridines |
| DE2101997A1 (en) * | 1971-01-16 | 1972-08-03 | Farbenfabriken Bayer AG, 509öfLeverkusen | 1-benzyl-4-subst-tetrahydropyridines - useful as intermediates for pharmaceuticals |
| FR2416886A1 (fr) * | 1978-02-08 | 1979-09-07 | Roussel Uclaf | Nouveaux derives de la 3-phenyl-tetrahydropyridine et leurs sels, procedes de preparation et application a titre de medicaments |
| FR2501682A1 (fr) * | 1981-03-11 | 1982-09-17 | Sanofi Sa | Trifluoromethylphenylpyridines a activite anorexigene, un procede de preparation et compositions pharmaceutiques en contenant |
| FR2501506A1 (fr) * | 1981-03-11 | 1982-09-17 | Sanofi Sa | Compositions pharmaceutiques a action anorexigene contenant des derives de la tetrahydropyridine |
-
1982
- 1982-08-16 FR FR8214169A patent/FR2531707A1/fr active Granted
-
1983
- 1983-07-26 IL IL69348A patent/IL69348A/xx not_active IP Right Cessation
- 1983-07-29 ZA ZA835577A patent/ZA835577B/xx unknown
- 1983-08-03 CA CA000433799A patent/CA1245662A/en not_active Expired
- 1983-08-04 AU AU17579/83A patent/AU562789B2/en not_active Expired
- 1983-08-10 DE DE8383401639T patent/DE3361424D1/de not_active Expired
- 1983-08-10 EP EP83401639A patent/EP0101381B1/fr not_active Expired
- 1983-08-10 AT AT83401639T patent/ATE16805T1/de not_active IP Right Cessation
- 1983-08-11 IE IE1885/83A patent/IE55870B1/en not_active IP Right Cessation
- 1983-08-12 GR GR72212A patent/GR78690B/el unknown
- 1983-08-12 ES ES525358A patent/ES8500264A1/es not_active Expired
- 1983-08-15 DK DK371983A patent/DK169269B1/da not_active IP Right Cessation
- 1983-08-15 NO NO832923A patent/NO161855C/no not_active IP Right Cessation
- 1983-08-15 NZ NZ205269A patent/NZ205269A/en unknown
- 1983-08-15 FI FI832930A patent/FI73992C/fi not_active IP Right Cessation
- 1983-08-16 JP JP58149513A patent/JPS5984865A/ja active Granted
- 1983-08-16 PT PT77205A patent/PT77205B/pt unknown
- 1983-08-16 US US06/523,565 patent/US4521428A/en not_active Expired - Lifetime
- 1983-08-16 YU YU1706/83A patent/YU44750B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT77205A (en) | 1983-09-01 |
| FI73992B (fi) | 1987-08-31 |
| IL69348A (en) | 1986-09-30 |
| FI73992C (fi) | 1987-12-10 |
| DE3361424D1 (en) | 1986-01-16 |
| EP0101381B1 (fr) | 1985-12-04 |
| IL69348A0 (en) | 1983-11-30 |
| JPH0557266B2 (fi) | 1993-08-23 |
| JPS5984865A (ja) | 1984-05-16 |
| PT77205B (en) | 1986-03-20 |
| EP0101381A1 (fr) | 1984-02-22 |
| ES525358A0 (es) | 1984-10-01 |
| ATE16805T1 (de) | 1985-12-15 |
| FR2531707A1 (fr) | 1984-02-17 |
| GR78690B (fi) | 1984-09-27 |
| AU1757983A (en) | 1984-02-23 |
| NO832923L (no) | 1984-02-17 |
| FI832930L (fi) | 1984-02-17 |
| US4521428A (en) | 1985-06-04 |
| FI832930A0 (fi) | 1983-08-15 |
| FR2531707B1 (fi) | 1985-01-18 |
| YU44750B (en) | 1991-02-28 |
| DK371983A (da) | 1984-02-17 |
| AU562789B2 (en) | 1987-06-18 |
| NO161855C (no) | 1989-10-04 |
| NO161855B (no) | 1989-06-26 |
| ZA835577B (en) | 1984-04-25 |
| CA1245662A (en) | 1988-11-29 |
| DK371983D0 (da) | 1983-08-15 |
| NZ205269A (en) | 1986-06-11 |
| YU170683A (en) | 1986-06-30 |
| ES8500264A1 (es) | 1984-10-01 |
| IE831885L (en) | 1984-02-16 |
| IE55870B1 (en) | 1991-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |