DE1493824A1 - Verfahren zur Herstellung von Aminocarbonsaeureamiden - Google Patents
Verfahren zur Herstellung von AminocarbonsaeureamidenInfo
- Publication number
- DE1493824A1 DE1493824A1 DE19641493824 DE1493824A DE1493824A1 DE 1493824 A1 DE1493824 A1 DE 1493824A1 DE 19641493824 DE19641493824 DE 19641493824 DE 1493824 A DE1493824 A DE 1493824A DE 1493824 A1 DE1493824 A1 DE 1493824A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- amide
- phenyl
- amphetamine
- amino
- 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.)
- Pending
Links
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- 230000008569 process Effects 0.000 title claims description 10
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- 238000002360 preparation method Methods 0.000 title description 4
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 24
- 150000001408 amides Chemical class 0.000 claims description 15
- 229940025084 amphetamine Drugs 0.000 claims description 13
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 230000010933 acylation Effects 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- PVFCXMDXBIEMQG-JTQLQIEISA-N (2s)-2-(phenylmethoxycarbonylamino)pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 PVFCXMDXBIEMQG-JTQLQIEISA-N 0.000 claims description 2
- 239000004201 L-cysteine Substances 0.000 claims description 2
- 235000013878 L-cysteine Nutrition 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000002844 melting Methods 0.000 description 17
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- 229960000583 acetic acid Drugs 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
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- 125000004149 thio group Chemical group *S* 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH93064 | 1964-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1493824A1 true DE1493824A1 (de) | 1969-05-22 |
Family
ID=4198470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641493824 Pending DE1493824A1 (de) | 1964-01-27 | 1964-11-23 | Verfahren zur Herstellung von Aminocarbonsaeureamiden |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE658748A (enrdf_load_stackoverflow) |
| DE (1) | DE1493824A1 (enrdf_load_stackoverflow) |
| ES (1) | ES308571A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1421130A (enrdf_load_stackoverflow) |
| NL (1) | NL6414901A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120157706A1 (en) * | 2010-12-20 | 2012-06-21 | Bauer Michael J | Methods and Compositions for Preparing Lisdexamfetamine and Salts Thereof |
| EP2560486A4 (en) * | 2010-04-21 | 2014-09-17 | Signature Therapeutics Inc | COMPOSITIONS OF ENZYMSPALTBAR AMPHETAMINE PRODRUGS AND INHIBITORS THEREFOR |
| US12384744B2 (en) | 2021-09-29 | 2025-08-12 | Ensysce Biosciences Inc. | Enzyme-cleavable methadone prodrugs and methods of use thereof |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6716452B1 (en) | 2000-08-22 | 2004-04-06 | New River Pharmaceuticals Inc. | Active agent delivery systems and methods for protecting and administering active agents |
| US8394813B2 (en) | 2000-11-14 | 2013-03-12 | Shire Llc | Active agent delivery systems and methods for protecting and administering active agents |
| US20060014697A1 (en) | 2001-08-22 | 2006-01-19 | Travis Mickle | Pharmaceutical compositions for prevention of overdose or abuse |
| US7169752B2 (en) | 2003-09-30 | 2007-01-30 | New River Pharmaceuticals Inc. | Compounds and compositions for prevention of overdose of oxycodone |
| US7105486B2 (en) * | 2002-02-22 | 2006-09-12 | New River Pharmaceuticals Inc. | Abuse-resistant amphetamine compounds |
| IL163667A0 (en) * | 2002-02-22 | 2005-12-18 | New River Pharmaceuticals Inc | Novel sustained release pharmaceutical compounds to preventabuse of controlled substances |
| US7700561B2 (en) * | 2002-02-22 | 2010-04-20 | Shire Llc | Abuse-resistant amphetamine prodrugs |
| US7659253B2 (en) | 2002-02-22 | 2010-02-09 | Shire Llc | Abuse-resistant amphetamine prodrugs |
| CA2527646C (en) * | 2003-05-29 | 2011-08-23 | New River Pharmaceuticals Inc. | Abuse resistant amphetamine compounds |
| NZ546226A (en) | 2003-09-30 | 2009-03-31 | Shire Llc | Oxycodone conjugates for prevention of overdose or abuse |
| CA2672138A1 (en) | 2006-12-11 | 2008-06-19 | Kempharm, Inc. | Non-standard amino acid conjugates of amphetamine and processes for making and using the same |
| DK3459538T3 (da) * | 2017-09-20 | 2020-08-03 | Sandoz Ag | Krystallinske salte af et dextroamfetamin-prodrug |
-
1964
- 1964-11-23 DE DE19641493824 patent/DE1493824A1/de active Pending
- 1964-12-21 NL NL6414901A patent/NL6414901A/xx unknown
-
1965
- 1965-01-20 FR FR2532A patent/FR1421130A/fr not_active Expired
- 1965-01-25 BE BE658748D patent/BE658748A/fr unknown
- 1965-01-26 ES ES0308571A patent/ES308571A1/es not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2560486A4 (en) * | 2010-04-21 | 2014-09-17 | Signature Therapeutics Inc | COMPOSITIONS OF ENZYMSPALTBAR AMPHETAMINE PRODRUGS AND INHIBITORS THEREFOR |
| US11179355B2 (en) | 2010-04-21 | 2021-11-23 | Signature Therapeutics, Inc. | Compositions comprising enzyme-cleavable amphetamine prodrugs and inhibitors thereof |
| US11400062B2 (en) | 2010-04-21 | 2022-08-02 | Signature Therapeutics, Inc. | Compositions comprising enzyme-cleavable amphetamine prodrugs and inhibitors thereof |
| US20120157706A1 (en) * | 2010-12-20 | 2012-06-21 | Bauer Michael J | Methods and Compositions for Preparing Lisdexamfetamine and Salts Thereof |
| US8779191B2 (en) * | 2010-12-20 | 2014-07-15 | Cambrex Charles City, Inc. | Methods and compositions for preparing lisdexamfetamine and salts thereof |
| US12384744B2 (en) | 2021-09-29 | 2025-08-12 | Ensysce Biosciences Inc. | Enzyme-cleavable methadone prodrugs and methods of use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6414901A (enrdf_load_stackoverflow) | 1965-07-28 |
| FR1421130A (fr) | 1965-12-10 |
| BE658748A (enrdf_load_stackoverflow) | 1965-07-26 |
| ES308571A1 (es) | 1966-06-01 |
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