ZA200502330B - 4-aminopiperidine derivatives processes for their preparation and their use as medicaments - Google Patents
4-aminopiperidine derivatives processes for their preparation and their use as medicaments Download PDFInfo
- Publication number
- ZA200502330B ZA200502330B ZA200502330A ZA200502330A ZA200502330B ZA 200502330 B ZA200502330 B ZA 200502330B ZA 200502330 A ZA200502330 A ZA 200502330A ZA 200502330 A ZA200502330 A ZA 200502330A ZA 200502330 B ZA200502330 B ZA 200502330B
- Authority
- ZA
- South Africa
- Prior art keywords
- piperidinecarboxylate
- tert
- butyl
- piperidinamine
- hydrogen
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title description 15
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical class NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 title description 7
- 230000008569 process Effects 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 62
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 239000011737 fluorine Substances 0.000 claims description 22
- -1 4-aminopiperidine compound Chemical class 0.000 claims description 20
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 238000003786 synthesis reaction Methods 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- ORKNCAZKJYJQJX-UHFFFAOYSA-N n-(3-fluorophenyl)-n-[(4-fluorophenyl)methyl]piperidin-4-amine Chemical compound C1=CC(F)=CC=C1CN(C=1C=C(F)C=CC=1)C1CCNCC1 ORKNCAZKJYJQJX-UHFFFAOYSA-N 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- NHENINYMLDQOSV-UHFFFAOYSA-N n-(3-fluorophenyl)-n-[(4-methylphenyl)methyl]piperidin-4-amine Chemical compound C1=CC(C)=CC=C1CN(C=1C=C(F)C=CC=1)C1CCNCC1 NHENINYMLDQOSV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- VLXRFBGQEPJBBY-UHFFFAOYSA-N n-[(4-methylphenyl)methyl]-n-phenylpiperidin-4-amine Chemical compound C1=CC(C)=CC=C1CN(C=1C=CC=CC=1)C1CCNCC1 VLXRFBGQEPJBBY-UHFFFAOYSA-N 0.000 claims description 5
- ZJWJLMVMSWQJEG-UHFFFAOYSA-N tert-butyl 4-(3-fluoroanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=CC(F)=C1 ZJWJLMVMSWQJEG-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- WFFKVJOHXLLCQR-UHFFFAOYSA-N n-(4-fluorophenyl)-n-[(4-fluorophenyl)methyl]piperidin-4-amine Chemical compound C1=CC(F)=CC=C1CN(C=1C=CC(F)=CC=1)C1CCNCC1 WFFKVJOHXLLCQR-UHFFFAOYSA-N 0.000 claims description 4
- XZCRHOZHVXRABP-UHFFFAOYSA-N n-(4-fluorophenyl)-n-[(4-methylphenyl)methyl]piperidin-4-amine Chemical compound C1=CC(C)=CC=C1CN(C=1C=CC(F)=CC=1)C1CCNCC1 XZCRHOZHVXRABP-UHFFFAOYSA-N 0.000 claims description 4
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
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- ODEAURLEPIKBBQ-UHFFFAOYSA-N tert-butyl 4-[4-fluoro-n-[(4-fluorophenyl)methyl]anilino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N(C=1C=CC(F)=CC=1)CC1=CC=C(F)C=C1 ODEAURLEPIKBBQ-UHFFFAOYSA-N 0.000 claims description 2
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- WHFOYQBREFHZHD-UHFFFAOYSA-N tert-butyl 4-[3-fluoro-n-[[4-(trifluoromethyl)phenyl]methyl]anilino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N(C=1C=C(F)C=CC=1)CC1=CC=C(C(F)(F)F)C=C1 WHFOYQBREFHZHD-UHFFFAOYSA-N 0.000 description 1
- PBVWEAJGULJUQL-UHFFFAOYSA-N tert-butyl 4-[3-methyl-n-[[4-(trifluoromethyl)phenyl]methyl]anilino]piperidine-1-carboxylate Chemical compound CC1=CC=CC(N(CC=2C=CC(=CC=2)C(F)(F)F)C2CCN(CC2)C(=O)OC(C)(C)C)=C1 PBVWEAJGULJUQL-UHFFFAOYSA-N 0.000 description 1
- MHCRFLOBVBFWPR-UHFFFAOYSA-N tert-butyl 4-[n-[(3,4-dichlorophenyl)methyl]-3-fluoroanilino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N(C=1C=C(F)C=CC=1)CC1=CC=C(Cl)C(Cl)=C1 MHCRFLOBVBFWPR-UHFFFAOYSA-N 0.000 description 1
- AQIHGXOWQRJHOK-UHFFFAOYSA-N tert-butyl 4-[n-[(3-chlorophenyl)methyl]-3-methylanilino]piperidine-1-carboxylate Chemical compound CC1=CC=CC(N(CC=2C=C(Cl)C=CC=2)C2CCN(CC2)C(=O)OC(C)(C)C)=C1 AQIHGXOWQRJHOK-UHFFFAOYSA-N 0.000 description 1
- RYQRFXJOCVNKAN-UHFFFAOYSA-N tert-butyl 4-[n-[(4-chlorophenyl)methyl]-3-methylanilino]piperidine-1-carboxylate Chemical compound CC1=CC=CC(N(CC=2C=CC(Cl)=CC=2)C2CCN(CC2)C(=O)OC(C)(C)C)=C1 RYQRFXJOCVNKAN-UHFFFAOYSA-N 0.000 description 1
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- 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
- A61K31/4465—Non condensed piperidines, e.g. piperocaine only substituted in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- 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
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02022191 | 2002-10-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200502330B true ZA200502330B (en) | 2006-05-31 |
Family
ID=32049973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200502330A ZA200502330B (en) | 2002-10-04 | 2005-03-18 | 4-aminopiperidine derivatives processes for their preparation and their use as medicaments |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US7488741B2 (da) |
| EP (2) | EP1556045B1 (da) |
| JP (1) | JP2006513151A (da) |
| KR (1) | KR20050055748A (da) |
| CN (1) | CN1688307A (da) |
| AT (1) | ATE334680T1 (da) |
| AU (1) | AU2003270291A1 (da) |
| BR (1) | BR0314811A (da) |
| CA (1) | CA2500664A1 (da) |
| DE (1) | DE60307308T2 (da) |
| DK (1) | DK1556045T3 (da) |
| ES (1) | ES2268406T3 (da) |
| MX (1) | MXPA05003290A (da) |
| NO (1) | NO20052172L (da) |
| NZ (1) | NZ539015A (da) |
| PL (1) | PL376368A1 (da) |
| PT (1) | PT1556045E (da) |
| RU (1) | RU2005110409A (da) |
| SI (1) | SI1556045T1 (da) |
| WO (1) | WO2004030668A1 (da) |
| ZA (1) | ZA200502330B (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003290735A1 (en) * | 2002-12-06 | 2004-06-30 | Eli Lilly And Company | Inhibitors of monoamine uptake |
| ES2298782T3 (es) * | 2003-06-11 | 2008-05-16 | Eli Lilly And Company | 3-aminopirrolidinas como inhibidores de la reabsorcion de monoaminas. |
| WO2005053663A2 (en) * | 2003-11-24 | 2005-06-16 | Eli Lilly And Company | Norepinephrine reuptake inhibitors useful for treatment of cognitive failure |
| US7615648B2 (en) * | 2004-06-01 | 2009-11-10 | Eli Lilly And Company | Aminomethyl-azacycle derivatives as inhibitors of monoamine uptake |
| EP2968359B1 (en) | 2013-03-12 | 2021-01-20 | Celltaxis, LLC | Methods of inhibiting leukotriene a4 hydrolase |
| JP2016513681A (ja) * | 2013-03-14 | 2016-05-16 | セルタクシス，インコーポレイテッド | ロイコトリエンａ４加水分解酵素の阻害剤 |
| JP7386815B2 (ja) | 2018-05-31 | 2023-11-27 | セルタクシー、エルエルシー | 呼吸器疾患患者の肺増悪を軽減する方法 |
| CN111233751B (zh) * | 2020-03-25 | 2021-02-02 | 丽水绿氟科技有限公司 | 一种3,3-二氟-4-氨基哌啶类化合物及其衍生物的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EG12406A (en) * | 1976-08-12 | 1979-03-31 | Janssen Pharmaceutica Nv | Process for preparing of novel n-aryl-n-(1-l-4-piperidinyl)-arylacetamides |
| JPH05148234A (ja) * | 1991-10-02 | 1993-06-15 | Hokuriku Seiyaku Co Ltd | アルカン酸誘導体 |
| DE4404183A1 (de) * | 1994-02-10 | 1995-08-17 | Merck Patent Gmbh | 4-Amino-1-piperidylbenzoylguanidine |
| GB0108876D0 (en) * | 2001-04-09 | 2001-05-30 | Novartis Ag | Organic Compounds |
-
2003
- 2003-09-30 US US10/528,924 patent/US7488741B2/en not_active Expired - Fee Related
- 2003-09-30 AU AU2003270291A patent/AU2003270291A1/en not_active Abandoned
- 2003-09-30 RU RU2005110409/04A patent/RU2005110409A/ru not_active Application Discontinuation
- 2003-09-30 SI SI200330506T patent/SI1556045T1/sl unknown
- 2003-09-30 PT PT03750658T patent/PT1556045E/pt unknown
- 2003-09-30 KR KR1020057005877A patent/KR20050055748A/ko not_active Application Discontinuation
- 2003-09-30 ES ES03750658T patent/ES2268406T3/es not_active Expired - Lifetime
- 2003-09-30 EP EP03750658A patent/EP1556045B1/en not_active Expired - Lifetime
- 2003-09-30 JP JP2004540745A patent/JP2006513151A/ja active Pending
- 2003-09-30 BR BR0314811-4A patent/BR0314811A/pt not_active IP Right Cessation
- 2003-09-30 DE DE60307308T patent/DE60307308T2/de not_active Expired - Lifetime
- 2003-09-30 WO PCT/EP2003/010824 patent/WO2004030668A1/en active IP Right Grant
- 2003-09-30 CA CA002500664A patent/CA2500664A1/en not_active Abandoned
- 2003-09-30 AT AT03750658T patent/ATE334680T1/de not_active IP Right Cessation
- 2003-09-30 PL PL03376368A patent/PL376368A1/xx not_active Application Discontinuation
- 2003-09-30 EP EP06008607A patent/EP1693061A1/en not_active Withdrawn
- 2003-09-30 NZ NZ539015A patent/NZ539015A/en unknown
- 2003-09-30 DK DK03750658T patent/DK1556045T3/da active
- 2003-09-30 MX MXPA05003290A patent/MXPA05003290A/es not_active Application Discontinuation
- 2003-09-30 CN CNA03823730XA patent/CN1688307A/zh active Pending
-
2005
- 2005-03-18 ZA ZA200502330A patent/ZA200502330B/en unknown
- 2005-05-03 NO NO20052172A patent/NO20052172L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004030668A1 (en) | 2004-04-15 |
| AU2003270291A1 (en) | 2004-04-23 |
| MXPA05003290A (es) | 2005-07-05 |
| PL376368A1 (en) | 2005-12-27 |
| KR20050055748A (ko) | 2005-06-13 |
| NO20052172L (no) | 2005-06-30 |
| EP1693061A1 (en) | 2006-08-23 |
| ATE334680T1 (de) | 2006-08-15 |
| SI1556045T1 (sl) | 2007-02-28 |
| US7488741B2 (en) | 2009-02-10 |
| JP2006513151A (ja) | 2006-04-20 |
| BR0314811A (pt) | 2005-08-02 |
| RU2005110409A (ru) | 2005-09-10 |
| US20060128753A1 (en) | 2006-06-15 |
| ES2268406T3 (es) | 2007-03-16 |
| EP1556045B1 (en) | 2006-08-02 |
| NZ539015A (en) | 2006-02-24 |
| EP1556045A1 (en) | 2005-07-27 |
| DK1556045T3 (da) | 2006-11-27 |
| CN1688307A (zh) | 2005-10-26 |
| DE60307308D1 (de) | 2006-09-14 |
| NO20052172D0 (no) | 2005-05-03 |
| CA2500664A1 (en) | 2004-04-15 |
| PT1556045E (pt) | 2006-12-29 |
| DE60307308T2 (de) | 2006-12-28 |
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