IL94914A - הפרדה של חומצה תראו-3-])2-אמינופניל( תיו[-2-הידרוקסי-3- )4-מתוקסיפניל( פרופיונית - Google Patents
הפרדה של חומצה תראו-3-])2-אמינופניל( תיו[-2-הידרוקסי-3- )4-מתוקסיפניל( פרופיוניתInfo
- Publication number
- IL94914A IL94914A IL9491490A IL9491490A IL94914A IL 94914 A IL94914 A IL 94914A IL 9491490 A IL9491490 A IL 9491490A IL 9491490 A IL9491490 A IL 9491490A IL 94914 A IL94914 A IL 94914A
- Authority
- IL
- Israel
- Prior art keywords
- threo
- acid
- pga
- mixture
- hereinafter
- Prior art date
Links
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 title claims description 9
- 125000000446 sulfanediyl group Chemical group *S* 0.000 title description 2
- 239000002253 acid Substances 0.000 claims abstract description 71
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 6
- GXBRYTMUEZNYJT-UHFFFAOYSA-N 2-anilinoacetamide Chemical compound NC(=O)CNC1=CC=CC=C1 GXBRYTMUEZNYJT-UHFFFAOYSA-N 0.000 claims description 4
- KIYRSYYOVDHSPG-SSDOTTSWSA-N (2r)-2-amino-2-phenylacetamide Chemical compound NC(=O)[C@H](N)C1=CC=CC=C1 KIYRSYYOVDHSPG-SSDOTTSWSA-N 0.000 claims description 3
- KIYRSYYOVDHSPG-ZETCQYMHSA-N (2s)-2-amino-2-phenylacetamide Chemical compound NC(=O)[C@@H](N)C1=CC=CC=C1 KIYRSYYOVDHSPG-ZETCQYMHSA-N 0.000 claims description 3
- KIYRSYYOVDHSPG-UHFFFAOYSA-N 2-amino-2-phenylacetamide Chemical compound NC(=O)C(N)C1=CC=CC=C1 KIYRSYYOVDHSPG-UHFFFAOYSA-N 0.000 claims description 2
- RHNVBCZIMHPLIV-UHFFFAOYSA-N 3-bromo-6-ethylpyridazine Chemical compound CCC1=CC=C(Br)N=N1 RHNVBCZIMHPLIV-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 13
- 239000005457 ice water Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 8
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 4
- 235000019766 L-Lysine Nutrition 0.000 description 3
- 239000004472 Lysine Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 239000004004 anti-anginal agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 1
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 1
- 229960004166 diltiazem Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 i = -335° (c = 0.3 Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 230000000063 preceeding effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- KEAYESYHFKHZAL-BJUDXGSMSA-N sodium-22 Chemical compound [22Na] KEAYESYHFKHZAL-BJUDXGSMSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU333589A HU205896B (en) | 1989-06-30 | 1989-06-30 | Process for resolving treo-3-//2-amino-phenyl/-thio/-2-hydroxy-3-/4-methoxy-phenyl/-propionic acid |
| HU333689A HU204774B (en) | 1989-06-30 | 1989-06-30 | Process for resolving alpha-phenylglycineamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL94914A0 IL94914A0 (en) | 1991-04-15 |
| IL94914A true IL94914A (he) | 1994-07-31 |
Family
ID=26317626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9491490A IL94914A (he) | 1989-06-30 | 1990-06-29 | הפרדה של חומצה תראו-3-])2-אמינופניל( תיו[-2-הידרוקסי-3- )4-מתוקסיפניל( פרופיונית |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5292933A (he) |
| EP (1) | EP0431121B1 (he) |
| JP (1) | JPH04500528A (he) |
| AT (1) | ATE93516T1 (he) |
| DE (1) | DE69002924T2 (he) |
| DK (1) | DK0431121T3 (he) |
| ES (1) | ES2060180T3 (he) |
| IE (1) | IE62410B1 (he) |
| IL (1) | IL94914A (he) |
| WO (1) | WO1991000270A1 (he) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1240651B (it) * | 1990-05-17 | 1993-12-17 | Zambon Spa | Processo per la risoluzione di derivati glicidici |
| EP3941895A1 (en) * | 2019-03-22 | 2022-01-26 | Tyme, Inc. | D-metyrosine compositions and methods for preparing same |
| PH12021552866A1 (en) | 2019-05-14 | 2022-11-07 | Tyme Inc | Compositions and methods for treating cancer |
| US10905698B1 (en) | 2020-05-14 | 2021-02-02 | Tyme, Inc. | Methods of treating SARS-COV-2 infections |
| WO2022006366A1 (en) * | 2020-07-01 | 2022-01-06 | Tyme, Inc. | Crystalline forms of metyrosine |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7413843A (nl) * | 1974-10-23 | 1976-04-27 | Stamicarbon | Optische scheiding van fenylglycine-amide. |
| SE449611B (sv) * | 1982-07-09 | 1987-05-11 | Tanabe Seiyaku Co | Sett att framstella 1,5-bensotiazepinderivat |
| IT1152721B (it) * | 1982-10-15 | 1987-01-07 | Luso Farmaco Inst | Risoluzione ottica dell'acido dl-alfa-2-idrossi-3-(4-metossifenil)-3-(2-amminofeniltio)propionico |
| EP0320532A1 (en) * | 1986-07-15 | 1989-06-21 | Nihon Iyakuhin Kogyo Co., Ltd. | Novel optically active carboxylic acid derivative l-lysine salt and process for production thereof |
| IT1217988B (it) * | 1988-01-28 | 1990-03-30 | Ind Chimica Profarmaco Spa | Procedimento per la risoluzione ottica di un pacemo |
| FR2630107B1 (fr) * | 1988-04-19 | 1990-06-08 | Synthelabo | Procede de preparation du (+) - (2s,3s) (amino-2 phenyl)thio)-3 hydroxy-2 (methoxy-4 phenyl)-3 propionate de methyle |
| US5008433A (en) * | 1988-05-18 | 1991-04-16 | Marion Laboratories, Inc. | 2-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propionic acid, 8'-phenylmenthyl ester, especially for diltiazem |
| FR2637285B1 (fr) * | 1988-10-03 | 1991-04-12 | Synthelabo | Procede de preparation de derives de l'acide propionique et produits obtenus |
-
1990
- 1990-06-29 US US07/684,892 patent/US5292933A/en not_active Expired - Fee Related
- 1990-06-29 WO PCT/HU1990/000045 patent/WO1991000270A1/en not_active Ceased
- 1990-06-29 IL IL9491490A patent/IL94914A/he not_active IP Right Cessation
- 1990-06-29 DE DE90909482T patent/DE69002924T2/de not_active Expired - Fee Related
- 1990-06-29 AT AT90909482T patent/ATE93516T1/de not_active IP Right Cessation
- 1990-06-29 IE IE236090A patent/IE62410B1/en not_active IP Right Cessation
- 1990-06-29 EP EP90909482A patent/EP0431121B1/en not_active Expired - Lifetime
- 1990-06-29 ES ES90909482T patent/ES2060180T3/es not_active Expired - Lifetime
- 1990-06-29 DK DK90909482.3T patent/DK0431121T3/da active
- 1990-06-29 JP JP2508964A patent/JPH04500528A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0431121B1 (en) | 1993-08-25 |
| IE902360L (en) | 1990-12-30 |
| DE69002924D1 (en) | 1993-09-30 |
| IE62410B1 (en) | 1995-01-25 |
| ES2060180T3 (es) | 1994-11-16 |
| IE902360A1 (en) | 1991-06-19 |
| ATE93516T1 (de) | 1993-09-15 |
| DK0431121T3 (da) | 1993-10-11 |
| US5292933A (en) | 1994-03-08 |
| WO1991000270A1 (en) | 1991-01-10 |
| EP0431121A1 (en) | 1991-06-12 |
| JPH04500528A (ja) | 1992-01-30 |
| IL94914A0 (en) | 1991-04-15 |
| DE69002924T2 (de) | 1993-12-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RH | Patent void |