HRP20120118T1 - Postupak proizvodnje [fenilsulfanilfenil] piperidina - Google Patents
Postupak proizvodnje [fenilsulfanilfenil] piperidina Download PDFInfo
- Publication number
- HRP20120118T1 HRP20120118T1 HR20120118T HRP20120118T HRP20120118T1 HR P20120118 T1 HRP20120118 T1 HR P20120118T1 HR 20120118 T HR20120118 T HR 20120118T HR P20120118 T HRP20120118 T HR P20120118T HR P20120118 T1 HRP20120118 T1 HR P20120118T1
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- Prior art keywords
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- compound
- alkyl
- formula
- process according
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract 23
- 238000004519 manufacturing process Methods 0.000 title claims 4
- NUVVEDILYSTVDX-UHFFFAOYSA-N 1-(2-phenylsulfanylphenyl)piperidine Chemical class C1CCCCN1C1=CC=CC=C1SC1=CC=CC=C1 NUVVEDILYSTVDX-UHFFFAOYSA-N 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 10
- 239000001257 hydrogen Substances 0.000 claims abstract 10
- SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 claims abstract 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 6
- 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 claims abstract 6
- 150000001875 compounds Chemical class 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 14
- 239000002253 acid Substances 0.000 claims 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 4
- -1 alkyl lithium Chemical compound 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 229910052749 magnesium Inorganic materials 0.000 claims 4
- 239000011777 magnesium Substances 0.000 claims 4
- 229910052751 metal Inorganic materials 0.000 claims 4
- 239000002184 metal Substances 0.000 claims 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 2
- 229910052744 lithium Inorganic materials 0.000 claims 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- LPLUHSYAFSMXGF-UHFFFAOYSA-N 1-benzyl-4-[2-(4-methylphenyl)sulfanylphenyl]piperidin-4-ol Chemical compound C1=CC(C)=CC=C1SC1=CC=CC=C1C1(O)CCN(CC=2C=CC=CC=2)CC1 LPLUHSYAFSMXGF-UHFFFAOYSA-N 0.000 claims 1
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 claims 1
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 claims 1
- WCZWFNWHXKDCFB-UHFFFAOYSA-N ethyl 4-ethoxycarbonyloxy-4-[2-(4-methylphenyl)sulfanylphenyl]piperidine-1-carboxylate Chemical compound C=1C=CC=C(SC=2C=CC(C)=CC=2)C=1C1(OC(=O)OCC)CCN(C(=O)OCC)CC1 WCZWFNWHXKDCFB-UHFFFAOYSA-N 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Postupak gdje spoj formule IIpri čemu R' i R" nezavisno predstavljaju jedan, dva ili tri vodika, halogen, C1-6-alkil ili C2-6-alkilen i L predstavlja odlazeću skupinu, reagira s N-benzil-4-piperidonom koji može biti po izboru supstituirangdje R"' predstavlja vodik ili -O-C1-6-alkil, radi dobivanja spoja formule IIIPatent sadrži još 19 patentnih zahtjeva.
Claims (20)
1. Postupak gdje spoj formule II
[image]
pri čemu R’ i R" nezavisno predstavljaju jedan, dva ili tri vodika, halogen, C1-6-alkil ili C2-6-alkilen i L predstavlja odlazeću skupinu, reagira s N-benzil-4-piperidonom koji može biti po izboru supstituiran
[image]
gdje R"’ predstavlja vodik ili -O-C1-6-alkil, radi dobivanja spoja formule III
[image]
2. Postupak prema zahtjevu 1, gdje spoj formule II
[image]
pri čemu R’ i R" nezavisno predstavljaju jedan, dva ili tri vodika, halogen, C1-6-alkil ili C2-6-alkilen i L predstavlja odlazeću skupinu, reagira sa sredstvom za dodavanje atoma metala izabranim između alkil litija, alkil magnezija ili magnezija i N-benzil-4-piperidonom koji može biti po izboru supstituiran
[image]
gdje R"’ predstavlja vodik ili -O-C1-6-alkil, pri temperaturi između oko -25°C i oko 5°C radi dobivanja spoja formule III
[image]
3. Postupak prema bilo kojem od zahtjeva 1-2, gdje R’ je 4-metil i R" je vodik.
4. Postupak prema bilo kojem od zahtjeva 1-3, gdje R"’ je vodik.
5. Postupak prema bilo kojem od zahtjeva 2-4, gdje sredstvo za dodavanje atoma metala n-butil litij.
6. Postupak proizvodnje spoja I
[image]
i njegovih kiselih adicijskih soli, gdje R’ i R" nezavisno predstavljaju jedan, dva ili tri vodika, halogen, C1-6-alkil ili C2-6-alkilen, a postupak obuhvaća korak reakcije spoja formule II
[image]
gdje L predstavlja odlazeću skupinu, s N-benzil-4-piperidonom koji može biti po izboru supstituiran
[image]
gdje R"’ predstavlja vodik ili O-C1-6-alkil, radi dobivanja spoja formule III
[image]
7. Postupak prema zahtjevu 6 za proizvodnju spoja I
[image]
i njegovih kiselih adicijskih soli, gdje R’ i R" nezavisno predstavljaju jedan, dva ili tri vodika, halogen, C1-6-alkil ili C2-6-alkilen, a postupak obuhvaća korake reakcije spoja formule II
[image]
gdje L predstavlja odlazeću skupinu, sa sredstvom za dodavanje atoma metala izabranim između alkil litija, alkil magnezija ili magnezija i N-benzil-4-piperidonom koji može biti po izboru supstituiran
[image]
gdje R"’ predstavlja vodik ili O-C1-6-alkil, pri temperaturi između -25°C i 5°C radi dobivanja spoja formule III
[image]
8. Postupak prema bilo kojem od zahtjeva 6-7, gdje R’ je 4-metil i R" je vodik.
9. Postupak prema bilo kojem od zahtjeva 6-8, gdje R"’ je vodik.
10. Postupak prema bilo kojem od zahtjeva 7-9, gdje je sredstvo za dodavanje atoma metala n-butil litij
11. Postupak prema bilo kojem od zahtjeva 6-10, gdje je spoj II
[image]
12. Postupak prema bilo kojem od zahtjeva 6-11, gdje je navedena sol adicijska sol bromovodične kiseline.
13. Postupak prema zahtjevu 6, gdje je spoj I
[image]
ili njegove kisele adicijske soli
taj postupak obuhvaća korake reakcije
[image]
s n-butil litijem pri temperaturi ispod 0°C, nakon čega slijedi reakcija s N-benzil-4-piperidonom pri temperaturi između oko 5°C i oko -25°C i HCl radi dobivanja spoja formule
[image]
a taj spoj dalje reagira s etil kloroformatom radi dobivanja spoja formule
[image]
a taj spoj dalje reagira s Et3SiH i trifluor octenom kiselinom, nakon čega slijedi reakcija s kiselinom da se ukloni N-piperidin zaštitna skupina i po izboru da se dobije željena kisela adicijska sol.
14. Postupak prema zahtjevu 13, gdje L je Br.
15. Postupak prema bilo kojem od zahtjeva 13-14, gdje je navedena sol adicijska sol bromovodične kiseline i gdje se N-zaštitna skupina uklanja reakcijom s bromovodičnom kiselinom u octenoj kiselini.
16. Postupak proizvodnje spoja formule
[image]
ili njegovih kiselih adicijskih soli, postupak obuhvaća korake reakcije spoja formule
[image]
s etil kloroformatom radi dobivanja spoja formule
[image]
a taj spoj dalje reagira s Et3SiH i trifluor octenom kiselinom, nakon čega slijedi reakcija s kiselinom da se ukloni N-piperidin zaštitna skupina i po izboru da se dobije željena kisela adicijska sol.
17. Postupak prema zahtjevu 16, gdje je navedena sol adicijska sol bromovodične kiseline i gdje se N-zaštitna skupina uklanja reakcijom s bromovodičnom kiselinom u octenoj kiselini.
18. Postupak prema zahtjevu 14, gdje se spoj
[image]
priprema u početnom koraku gdje 4-metiltiofenol i 2-jodobromobenzen reagiraju u prisutnosti izvora paladija i bidentatnog liganda fosfina pri lužnatom pH na povišenim temperaturama.
19. Spoj prema formuli i) ili ii)
[image]
i
[image]
gdje R’ i R" nezavisno predstavljaju jedan, dva ili tri vodika, halogen, C1-6-alkil ili C2-6-alkilen, i gdje R"’ predstavlja vodik ili -O-C1-6-alkil, i njegove kisele adicijske soli.
20. Spoj prema zahtjevu 19 izabran između
1-benzil-4-hidroksi-4-[2-(4-metilfenilsulfanil)fenil]piperidin; i
etilni ester 4-etoksikarboniloksi-4-(2-p-tolilsulfanil-fenil)-piperidin-1-karboksilne kiseline;
te njegove kisele adicijske soli.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3309308P | 2008-03-03 | 2008-03-03 | |
| DKPA200800314 | 2008-03-03 | ||
| PCT/EP2009/052440 WO2009109541A1 (en) | 2008-03-03 | 2009-03-02 | Process for the manufacture of [phenylsulfanylphenyl]piperidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20120118T1 true HRP20120118T1 (hr) | 2012-03-31 |
Family
ID=40547924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20120118T HRP20120118T1 (hr) | 2008-03-03 | 2012-02-03 | Postupak proizvodnje [fenilsulfanilfenil] piperidina |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US8362255B2 (hr) |
| EP (1) | EP2260024B1 (hr) |
| JP (1) | JP5564439B2 (hr) |
| KR (1) | KR20100122914A (hr) |
| CN (1) | CN101959859B (hr) |
| AR (1) | AR070737A1 (hr) |
| AT (1) | ATE539055T1 (hr) |
| AU (1) | AU2009221170B2 (hr) |
| BR (1) | BRPI0908166A2 (hr) |
| CA (1) | CA2715579A1 (hr) |
| CL (1) | CL2009000490A1 (hr) |
| CO (1) | CO6290758A2 (hr) |
| CY (1) | CY1113887T1 (hr) |
| DK (1) | DK2260024T3 (hr) |
| EA (1) | EA017855B1 (hr) |
| ES (1) | ES2377862T3 (hr) |
| HK (1) | HK1153458A1 (hr) |
| HR (1) | HRP20120118T1 (hr) |
| IL (1) | IL207471A (hr) |
| MX (1) | MX2010008729A (hr) |
| NZ (1) | NZ587593A (hr) |
| PL (1) | PL2260024T3 (hr) |
| PT (1) | PT2260024E (hr) |
| RS (1) | RS52128B (hr) |
| SI (1) | SI2260024T1 (hr) |
| TW (1) | TW200940505A (hr) |
| UA (1) | UA98698C2 (hr) |
| WO (1) | WO2009109541A1 (hr) |
| ZA (1) | ZA201006135B (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA016054B1 (ru) * | 2006-06-16 | 2012-01-30 | Х. Лундбекк А/С | Кристаллические формы 4-[2-(4-метилфенилсульфанил)фенил] пиперидина с объединенным ингибированием повторного поглощения серотонина и норадреналина для лечения невропатической боли |
| JP2012163850A (ja) * | 2011-02-08 | 2012-08-30 | Nippon Sheet Glass Co Ltd | 正立等倍レンズアレイプレート、光走査ユニット、画像読取装置および画像書込装置 |
| PE20150194A1 (es) | 2012-05-21 | 2015-02-08 | Novartis Ag | Novedosas n-piridinil amidas ciclicas sustituidas como inhibidores de quinasa |
| CN104710345B (zh) * | 2013-12-17 | 2017-09-05 | 江苏恩华药业股份有限公司 | 用于制备4‑（2‑（4‑甲基苯基硫基））苯基哌啶的化合物、其制备方法及应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2324087A (en) * | 1997-04-10 | 1998-10-14 | Merck & Co Inc | Preparation of (S)-3-Carbethoxy-3-benzylpiperidine |
| WO2001046143A1 (en) | 1999-12-20 | 2001-06-28 | Eli Lilly And Company | A process for preparing trans-2,4-disubstituted piperidines |
| UA81749C2 (uk) * | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
| UA81300C2 (en) * | 2003-04-04 | 2007-12-25 | Lundbeck & Co As H | Derivates of 4-(2-fenilsulfanilfenil)-1,2,3,6-tetrahydropiridin as retarding agents of serotonin recapture |
| JP4667366B2 (ja) * | 2003-04-04 | 2011-04-13 | ハー・ルンドベック・アクチエゼルスカベット | セロトニン再取り込み阻害剤としての４−（２−フェニルスルファニル−フェニル）−ピペリジン誘導体 |
| EA016054B1 (ru) | 2006-06-16 | 2012-01-30 | Х. Лундбекк А/С | Кристаллические формы 4-[2-(4-метилфенилсульфанил)фенил] пиперидина с объединенным ингибированием повторного поглощения серотонина и норадреналина для лечения невропатической боли |
-
2009
- 2009-02-03 UA UAA201011031A patent/UA98698C2/ru unknown
- 2009-02-19 TW TW098105235A patent/TW200940505A/zh unknown
- 2009-03-02 US US12/920,357 patent/US8362255B2/en not_active Expired - Fee Related
- 2009-03-02 AU AU2009221170A patent/AU2009221170B2/en not_active Ceased
- 2009-03-02 KR KR1020107019480A patent/KR20100122914A/ko not_active Application Discontinuation
- 2009-03-02 WO PCT/EP2009/052440 patent/WO2009109541A1/en active Application Filing
- 2009-03-02 EP EP09717792A patent/EP2260024B1/en active Active
- 2009-03-02 CL CL2009000490A patent/CL2009000490A1/es unknown
- 2009-03-02 AT AT09717792T patent/ATE539055T1/de active
- 2009-03-02 PT PT09717792T patent/PT2260024E/pt unknown
- 2009-03-02 MX MX2010008729A patent/MX2010008729A/es active IP Right Grant
- 2009-03-02 CN CN200980108235XA patent/CN101959859B/zh not_active Expired - Fee Related
- 2009-03-02 SI SI200930184T patent/SI2260024T1/sl unknown
- 2009-03-02 AR ARP090100734A patent/AR070737A1/es unknown
- 2009-03-02 PL PL09717792T patent/PL2260024T3/pl unknown
- 2009-03-02 CA CA2715579A patent/CA2715579A1/en not_active Abandoned
- 2009-03-02 ES ES09717792T patent/ES2377862T3/es active Active
- 2009-03-02 NZ NZ587593A patent/NZ587593A/en not_active IP Right Cessation
- 2009-03-02 RS RS20120063A patent/RS52128B/en unknown
- 2009-03-02 EA EA201071025A patent/EA017855B1/ru not_active IP Right Cessation
- 2009-03-02 JP JP2010549114A patent/JP5564439B2/ja not_active Expired - Fee Related
- 2009-03-02 DK DK09717792.7T patent/DK2260024T3/da active
- 2009-03-02 BR BRPI0908166-6A patent/BRPI0908166A2/pt not_active IP Right Cessation
-
2010
- 2010-08-08 IL IL207471A patent/IL207471A/en not_active IP Right Cessation
- 2010-08-27 ZA ZA2010/06135A patent/ZA201006135B/en unknown
- 2010-09-02 CO CO10108740A patent/CO6290758A2/es active IP Right Grant
-
2011
- 2011-07-18 HK HK11107430.0A patent/HK1153458A1/xx not_active IP Right Cessation
-
2012
- 2012-02-03 HR HR20120118T patent/HRP20120118T1/hr unknown
- 2012-02-13 CY CY20121100145T patent/CY1113887T1/el unknown
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