JP2006513243A5 - - Google Patents
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- Publication number
- JP2006513243A5 JP2006513243A5 JP2004566248A JP2004566248A JP2006513243A5 JP 2006513243 A5 JP2006513243 A5 JP 2006513243A5 JP 2004566248 A JP2004566248 A JP 2004566248A JP 2004566248 A JP2004566248 A JP 2004566248A JP 2006513243 A5 JP2006513243 A5 JP 2006513243A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- amino
- aspartic acid
- ester
- 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 claims 9
- CKLJMWTZIZZHCS-UWTATZPHSA-N D-aspartic acid Chemical class OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims 7
- 230000007062 hydrolysis Effects 0.000 claims 4
- 238000006460 hydrolysis reaction Methods 0.000 claims 4
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Chemical class OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 229960005261 aspartic acid Drugs 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 229940006015 4-hydroxybutyric acid Drugs 0.000 claims 2
- 150000008557 D-aspartic acids Chemical class 0.000 claims 2
- 229940124277 aminobutyric acid Drugs 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 150000002596 lactones Chemical class 0.000 claims 2
- 238000011084 recovery Methods 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- DAWBGYHPBBDHMQ-ZCFIWIBFSA-N (3r)-3-amino-4-(trimethylazaniumyl)butanoate Chemical compound C[N+](C)(C)C[C@H](N)CC([O-])=O DAWBGYHPBBDHMQ-ZCFIWIBFSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- NYSTXWQMQQTMBC-UHFFFAOYSA-N C[N+](C)(C)CC(CC([O-])=O)(N)O.P Chemical compound C[N+](C)(C)CC(CC([O-])=O)(N)O.P NYSTXWQMQQTMBC-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- XGCKLPDYTQRDTR-UHFFFAOYSA-H indium(iii) sulfate Chemical compound [In+3].[In+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O XGCKLPDYTQRDTR-UHFFFAOYSA-H 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000007142 ring opening reaction Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 1
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical group CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 claims 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/338,045 US20030153783A1 (en) | 1999-06-30 | 2003-01-08 | Synthesis of (R) and (S)-aminocarnitine, (R) and (S)-4-phosphonium-3-amino-butanoate, (R) and (S) 3,4-diaminobutanoic acid, and their derivatives starting from D- and L-aspartic acid |
| US10/372,627 US6822115B2 (en) | 1999-06-30 | 2003-02-25 | Synthesis of (R) and (S)-aminocarnitine, (R) and (S)-4-phosphonium-3-amino-butanoate, (R) and (S) 3,4-diaminobutanoic acid, and their derivatives starting from D- and L-aspartic acid |
| PCT/IT2003/000846 WO2004063143A1 (en) | 2003-01-08 | 2003-12-19 | Synthesis fo (r) and (s)-aminocarnitine and derivatives thereof from d-and l-aspartic acid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006513243A JP2006513243A (ja) | 2006-04-20 |
| JP2006513243A5 true JP2006513243A5 (enExample) | 2007-02-08 |
| JP4642476B2 JP4642476B2 (ja) | 2011-03-02 |
Family
ID=32716886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004566248A Expired - Fee Related JP4642476B2 (ja) | 2003-01-08 | 2003-12-19 | （ｒ）および（ｓ）−アミノカルニチンおよびその誘導体のｄ−およびｌ−アスパラギン酸からの合成 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6822115B2 (enExample) |
| EP (1) | EP1581475B1 (enExample) |
| JP (1) | JP4642476B2 (enExample) |
| KR (1) | KR20050092398A (enExample) |
| CN (1) | CN1735588B (enExample) |
| AT (1) | ATE443039T1 (enExample) |
| AU (1) | AU2003295219B2 (enExample) |
| BR (1) | BR0317956A (enExample) |
| CA (1) | CA2512679A1 (enExample) |
| CY (1) | CY1109545T1 (enExample) |
| DE (1) | DE60329325D1 (enExample) |
| DK (1) | DK1581475T3 (enExample) |
| ES (1) | ES2333523T3 (enExample) |
| MX (1) | MXPA05007315A (enExample) |
| PL (1) | PL378538A1 (enExample) |
| PT (1) | PT1581475E (enExample) |
| SI (1) | SI1581475T1 (enExample) |
| WO (1) | WO2004063143A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1299266B1 (it) * | 1998-05-15 | 2000-02-29 | Sigma Tau Ind Farmaceuti | Inibitori reversibili della carnitina palmitoil trasferasi |
| ITRM20050090A1 (it) * | 2005-03-02 | 2006-09-03 | Sigma Tau Ind Farmaceutiche Riunite Spa | Derivati dell'acido ammino-butanoico inibitore della cpt. |
| US7776915B2 (en) * | 2005-03-24 | 2010-08-17 | Tracie Martyn International, Llc | Topical formulations and methods of use |
| US8410150B2 (en) * | 2007-03-09 | 2013-04-02 | University Health Network | Inhibitors of carnitine palmitoyltransferase and treating cancer |
| CA2677049A1 (en) * | 2007-08-01 | 2009-02-05 | Sionex Corporation | Cyclic inhibitors of carnitine palmitoyltransferase and treating cancer |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1136945B (it) * | 1981-03-18 | 1986-09-03 | Anic Spa | Processo per la preparazione di l-carnitina |
| IT1261489B (it) | 1993-07-29 | 1996-05-23 | Sigma Tau Ind Farmaceuti | Procedimento per la produzione di r amminocarnitina e s amminocarnitina. |
| IT1299266B1 (it) * | 1998-05-15 | 2000-02-29 | Sigma Tau Ind Farmaceuti | Inibitori reversibili della carnitina palmitoil trasferasi |
| US20030153783A1 (en) * | 1999-06-30 | 2003-08-14 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Synthesis of (R) and (S)-aminocarnitine, (R) and (S)-4-phosphonium-3-amino-butanoate, (R) and (S) 3,4-diaminobutanoic acid, and their derivatives starting from D- and L-aspartic acid |
| IT1306162B1 (it) * | 1999-06-30 | 2001-05-30 | Sigma Tau Ind Farmaceuti | Sintesi di (r) e (s)-amminocarnitina e di suoi derivati a partire daacido d e l-aspartico. |
-
2003
- 2003-02-25 US US10/372,627 patent/US6822115B2/en not_active Expired - Fee Related
- 2003-12-19 MX MXPA05007315A patent/MXPA05007315A/es active IP Right Grant
- 2003-12-19 JP JP2004566248A patent/JP4642476B2/ja not_active Expired - Fee Related
- 2003-12-19 PT PT03786222T patent/PT1581475E/pt unknown
- 2003-12-19 DE DE60329325T patent/DE60329325D1/de not_active Expired - Lifetime
- 2003-12-19 AU AU2003295219A patent/AU2003295219B2/en not_active Ceased
- 2003-12-19 BR BRPI0317956-7A patent/BR0317956A/pt not_active IP Right Cessation
- 2003-12-19 ES ES03786222T patent/ES2333523T3/es not_active Expired - Lifetime
- 2003-12-19 KR KR1020057012832A patent/KR20050092398A/ko not_active Abandoned
- 2003-12-19 SI SI200331683T patent/SI1581475T1/sl unknown
- 2003-12-19 AT AT03786222T patent/ATE443039T1/de active
- 2003-12-19 CN CN2003801085435A patent/CN1735588B/zh not_active Expired - Fee Related
- 2003-12-19 DK DK03786222.4T patent/DK1581475T3/da active
- 2003-12-19 CA CA002512679A patent/CA2512679A1/en not_active Abandoned
- 2003-12-19 PL PL378538A patent/PL378538A1/pl not_active Application Discontinuation
- 2003-12-19 EP EP03786222A patent/EP1581475B1/en not_active Expired - Lifetime
- 2003-12-19 WO PCT/IT2003/000846 patent/WO2004063143A1/en not_active Ceased
-
2009
- 2009-12-04 CY CY20091101274T patent/CY1109545T1/el unknown
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