FR2459240A1 - Aminopiperidines anorexigenes, procede pour leur preparation, intermediaires dans ledit procede et medicaments qui les contiennent - Google Patents
Aminopiperidines anorexigenes, procede pour leur preparation, intermediaires dans ledit procede et medicaments qui les contiennent Download PDFInfo
- Publication number
- FR2459240A1 FR2459240A1 FR7915974A FR7915974A FR2459240A1 FR 2459240 A1 FR2459240 A1 FR 2459240A1 FR 7915974 A FR7915974 A FR 7915974A FR 7915974 A FR7915974 A FR 7915974A FR 2459240 A1 FR2459240 A1 FR 2459240A1
- Authority
- FR
- France
- Prior art keywords
- group
- pyridyl
- amino
- piperidine
- halogen
- 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
- 238000000034 method Methods 0.000 title claims abstract description 18
- 230000008569 process Effects 0.000 title claims abstract description 7
- 239000003814 drug Substances 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 239000000543 intermediate Substances 0.000 title description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
- 239000000047 product Substances 0.000 claims description 12
- CZINLSYKXBADTA-UHFFFAOYSA-N 1-pyridin-2-ylpiperidin-4-amine Chemical class C1CC(N)CCN1C1=CC=CC=N1 CZINLSYKXBADTA-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- YLWUSMHZABTZGP-UHFFFAOYSA-N n-piperidin-4-ylacetamide Chemical compound CC(=O)NC1CCNCC1 YLWUSMHZABTZGP-UHFFFAOYSA-N 0.000 claims description 8
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 4
- WPVVMKYQOMJPIN-UHFFFAOYSA-N 1-(6-chloro-2-pyridinyl)-4-piperidinamine Chemical compound C1CC(N)CCN1C1=CC=CC(Cl)=N1 WPVVMKYQOMJPIN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
- 150000005749 2-halopyridines Chemical class 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
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- UVZFVSNJAQJYCQ-UHFFFAOYSA-N 1-(6-methoxypyridin-2-yl)piperidin-4-amine;hydrochloride Chemical compound Cl.COC1=CC=CC(N2CCC(N)CC2)=N1 UVZFVSNJAQJYCQ-UHFFFAOYSA-N 0.000 claims description 2
- FHBCTQQQTPYSTA-UHFFFAOYSA-N 1-(6-methylpyridin-2-yl)piperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC(N2CCC(N)CC2)=N1 FHBCTQQQTPYSTA-UHFFFAOYSA-N 0.000 claims description 2
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- SGLJQTKFRSTKLJ-UHFFFAOYSA-N 1-(6-bromopyridin-2-yl)piperidin-4-amine;hydrochloride Chemical compound Cl.C1CC(N)CCN1C1=CC=CC(Br)=N1 SGLJQTKFRSTKLJ-UHFFFAOYSA-N 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- CXEJLCGIRISACP-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)formamide Chemical compound C1CC(NC=O)CCN1CC1=CC=CC=C1 CXEJLCGIRISACP-UHFFFAOYSA-N 0.000 description 1
- IMFINBLMVWTWQX-UHFFFAOYSA-N n-[1-(6-chloropyridin-2-yl)piperidin-4-yl]acetamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC=CC(Cl)=N1 IMFINBLMVWTWQX-UHFFFAOYSA-N 0.000 description 1
- MQBHRQVKQODGLJ-UHFFFAOYSA-N n-[1-(6-methoxypyridin-2-yl)piperidin-4-yl]acetamide Chemical compound COC1=CC=CC(N2CCC(CC2)NC(C)=O)=N1 MQBHRQVKQODGLJ-UHFFFAOYSA-N 0.000 description 1
- WDOWZTLOVXPBHR-UHFFFAOYSA-N n-[1-(6-phenylsulfanylpyridin-2-yl)piperidin-4-yl]acetamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC=CC(SC=2C=CC=CC=2)=N1 WDOWZTLOVXPBHR-UHFFFAOYSA-N 0.000 description 1
- OVFHYSUFZYZAEA-UHFFFAOYSA-N n-[1-[6-(2,2,2-trifluoroethoxy)pyridin-2-yl]piperidin-4-yl]acetamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC=CC(OCC(F)(F)F)=N1 OVFHYSUFZYZAEA-UHFFFAOYSA-N 0.000 description 1
- NLTYRNPXSYWTID-UHFFFAOYSA-N n-[2-(3-chloropyridin-2-yl)piperidin-4-yl]acetamide Chemical compound C1C(NC(=O)C)CCNC1C1=NC=CC=C1Cl NLTYRNPXSYWTID-UHFFFAOYSA-N 0.000 description 1
- VXPPKXMXWAXARF-UHFFFAOYSA-N n-[2-(6-phenylsulfanylpyridin-2-yl)piperidin-4-yl]acetamide Chemical compound C1C(NC(=O)C)CCNC1C1=CC=CC(SC=2C=CC=CC=2)=N1 VXPPKXMXWAXARF-UHFFFAOYSA-N 0.000 description 1
- SXESBRNYONQKLV-UHFFFAOYSA-N n-piperidin-1-ylacetamide Chemical compound CC(=O)NN1CCCCC1 SXESBRNYONQKLV-UHFFFAOYSA-N 0.000 description 1
- QQWXHHWNGQDRCX-UHFFFAOYSA-N n-piperidin-4-ylformamide Chemical compound O=CNC1CCNCC1 QQWXHHWNGQDRCX-UHFFFAOYSA-N 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
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000012154 norepinephrine uptake Effects 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- PFWWZGINJSDVGU-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1.C1CCNCC1 PFWWZGINJSDVGU-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 231100000316 potential neurotoxicity Toxicity 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- MSGMXYUAWZYTFC-UHFFFAOYSA-N sodium;2,2,2-trifluoroethanolate Chemical compound [Na+].[O-]CC(F)(F)F MSGMXYUAWZYTFC-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 125000005490 tosylate group Chemical group 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Obesity (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Child & Adolescent Psychology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7915974A FR2459240A1 (fr) | 1979-06-21 | 1979-06-21 | Aminopiperidines anorexigenes, procede pour leur preparation, intermediaires dans ledit procede et medicaments qui les contiennent |
| ES492484A ES492484A0 (es) | 1979-06-21 | 1980-06-16 | Procedimiento para la preparacion de 4-amino-1-(2-piridil) piperidinas |
| EP81107653A EP0045980B1 (fr) | 1979-06-21 | 1980-06-17 | Composés utiles notamment pour la préparation d'aminopipéridines ayant des propriétés anorexigènes |
| EP80400874A EP0021973B1 (fr) | 1979-06-21 | 1980-06-17 | Aminopipéridines anorexigènes, procédé pour leur préparation et médicaments les contenant |
| AT80400874T ATE1930T1 (de) | 1979-06-21 | 1980-06-17 | Appetithemmende aminopiperidine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel. |
| AT81107653T ATE4901T1 (de) | 1979-06-21 | 1980-06-17 | Fuer die herstellung von aminopiperidinen mit appetithemmender wirkung nuetzliche verbindungen. |
| DE8080400874T DE3061266D1 (en) | 1979-06-21 | 1980-06-17 | Anorectic amino piperidines, process for their preparation and medicaments containing them |
| DE8181107653T DE3065220D1 (en) | 1979-06-21 | 1980-06-17 | Compounds useful in the preparation of aminopiperidines with anorectic properties |
| CA000354142A CA1142936A (en) | 1979-06-21 | 1980-06-17 | 4-amino-1-(2-pyridyl)piperidine compounds |
| AR281448A AR229088A1 (es) | 1979-06-21 | 1980-06-18 | Procedimiento para preparar nuevas aminopiperidinas que tienen una actividad anorexica |
| MX10144180U MX6113E (es) | 1979-06-21 | 1980-06-18 | Procedimiento para preparar 4-amino-1-(2-piridil)-piperidinas |
| JP8300880A JPS5636481A (en) | 1979-06-21 | 1980-06-20 | Aminopiperidine* its manufacture* intermediate and medicine |
| US06/327,022 US4409228A (en) | 1979-06-21 | 1981-12-03 | Andrexiant aminopiperidines intermediates thereto and drugs containing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7915974A FR2459240A1 (fr) | 1979-06-21 | 1979-06-21 | Aminopiperidines anorexigenes, procede pour leur preparation, intermediaires dans ledit procede et medicaments qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2459240A1 true FR2459240A1 (fr) | 1981-01-09 |
| FR2459240B1 FR2459240B1 (enExample) | 1982-10-22 |
Family
ID=9226937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7915974A Granted FR2459240A1 (fr) | 1979-06-21 | 1979-06-21 | Aminopiperidines anorexigenes, procede pour leur preparation, intermediaires dans ledit procede et medicaments qui les contiennent |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4409228A (enExample) |
| EP (2) | EP0021973B1 (enExample) |
| JP (1) | JPS5636481A (enExample) |
| AR (1) | AR229088A1 (enExample) |
| AT (1) | ATE4901T1 (enExample) |
| CA (1) | CA1142936A (enExample) |
| DE (1) | DE3061266D1 (enExample) |
| ES (1) | ES492484A0 (enExample) |
| FR (1) | FR2459240A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA848275B (en) * | 1983-12-28 | 1985-08-28 | Degussa | New piridine-2-ethers or pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring |
| GB8710494D0 (en) * | 1987-05-02 | 1987-06-03 | Pfizer Ltd | Antiarrhythmic agents |
| FR2674435B1 (fr) * | 1991-03-27 | 1995-03-10 | Sanofi Elf | Utilisation de 4-amino-1-(2-pyridyl) piperidines pour la preparation d'agents psychotropes. |
| EP0506545B1 (fr) * | 1991-03-27 | 1998-12-30 | Sanofi | Utilisation de 4-amino-1-(2-pyridyl)pipéridines comme agonistes 5-HT3 pour le traitement et la prophylaxie des dysfonctionnements sérotoninergiques |
| FR2674752B1 (fr) * | 1991-09-03 | 1995-03-10 | Sanofi Elf | Utilisation de 4-amino-1-(2-pyridyl)piperidines pour la preparation de medicaments pour le traitement et la prophylaxie des etats decoulant d'un dysfonctionnement du systeme serotoninergique. |
| FR2681785B1 (fr) * | 1991-09-30 | 1995-05-24 | Sanofi Elf | Utilisation de 4-amino-1-(2-pyridyl)piperidines en tant qu'agents anticonvulsivants et antiepileptiques. |
| CN1052224C (zh) * | 1993-04-07 | 2000-05-10 | 大塚制药株式会社 | 哌啶衍生物、含有它的外周血管舒张剂及其应用 |
| US6632823B1 (en) * | 1997-12-22 | 2003-10-14 | Merck & Co., Inc. | Substituted pyridine compounds useful as modulators of acetylcholine receptors |
| KR100713572B1 (ko) * | 1999-05-21 | 2007-05-02 | 아보트 러보러터리즈 | 중추 신경계 제제로서 유용한 헤테로사이클릭 치환된 아미노아자사이클 및 이를 포함하는 약제학적 조성물 |
| BR0007229A (pt) | 1999-05-21 | 2002-09-10 | Abbott Lab | Aminoazaciclos heterocìclicos substituìdos úteis como agentes de sistema nervoso central |
| US6833370B1 (en) * | 1999-05-21 | 2004-12-21 | Abbott Laboratories | Heterocycle substituted aminoazacycles useful as central nervous system agents |
| AU782648B2 (en) * | 1999-11-23 | 2005-08-18 | Janssen Pharmaceutica N.V. | Use of 5HT3 agonists for relaxing the fundus |
| NZ520041A (en) * | 2000-01-20 | 2004-11-26 | Eisai Co Ltd | Novel piperidine compounds and drugs containing the same |
| TW200303201A (en) * | 2001-12-10 | 2003-09-01 | Bristol Myers Squibb Co | Synthesis of 4,5-dihydro-pyrazolo [3,4-c] pyrid-2-ones |
| GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| PT2013211E (pt) | 2006-04-21 | 2012-06-21 | Novartis Ag | Derivados de purina para utilização como agonistas de receptores a2a de adenosina |
| CN102452978A (zh) * | 2010-11-01 | 2012-05-16 | 重庆康丁医药技术有限公司 | 2-氯-取代或未取代脂族烃氧基吡啶及其制备方法 |
| CN111050800B (zh) | 2017-06-28 | 2023-04-04 | 国立大学法人大阪大学 | 血清素3受体激动剂对疼痛的治疗 |
| TW202508584A (zh) | 2023-05-25 | 2025-03-01 | 日商丸石製藥股份有限公司 | 癌性疼痛預防或治療用組成物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE738495C (de) * | 1941-08-10 | 1943-08-18 | Kastel Tvornica Kemijsko Farma | Verfahren zur Darstellung von substituierten 4-Aminopiperidinen |
-
1979
- 1979-06-21 FR FR7915974A patent/FR2459240A1/fr active Granted
-
1980
- 1980-06-16 ES ES492484A patent/ES492484A0/es active Granted
- 1980-06-17 EP EP80400874A patent/EP0021973B1/fr not_active Expired
- 1980-06-17 DE DE8080400874T patent/DE3061266D1/de not_active Expired
- 1980-06-17 CA CA000354142A patent/CA1142936A/en not_active Expired
- 1980-06-17 AT AT81107653T patent/ATE4901T1/de not_active IP Right Cessation
- 1980-06-17 EP EP81107653A patent/EP0045980B1/fr not_active Expired
- 1980-06-18 AR AR281448A patent/AR229088A1/es active
- 1980-06-20 JP JP8300880A patent/JPS5636481A/ja active Pending
-
1981
- 1981-12-03 US US06/327,022 patent/US4409228A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3061266D1 (en) | 1983-01-13 |
| FR2459240B1 (enExample) | 1982-10-22 |
| JPS5636481A (en) | 1981-04-09 |
| CA1142936A (en) | 1983-03-15 |
| ES8104274A1 (es) | 1981-04-16 |
| ATE4901T1 (de) | 1983-10-15 |
| EP0021973A3 (en) | 1981-04-29 |
| EP0045980B1 (fr) | 1983-10-05 |
| US4409228A (en) | 1983-10-11 |
| EP0045980A1 (fr) | 1982-02-17 |
| EP0021973A2 (fr) | 1981-01-07 |
| ES492484A0 (es) | 1981-04-16 |
| EP0021973B1 (fr) | 1982-12-08 |
| AR229088A1 (es) | 1983-06-15 |
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| TP | Transmission of property | ||
| ST | Notification of lapse |