IL94914A - Acid separation. - Google Patents

Acid separation.

Info

Publication number: IL94914A
Authority: IL; Israel
Prior art keywords: threo; acid; pga; mixture; hereinafter
Prior art date: 1989-06-30

Application number

IL9491490A

Other languages

English (en)

Hebrew (he)

Other versions

IL94914A0 (en

Original Assignee

Richter Gedeon Vegyeszet

Priority date (The priority date 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 date listed.)

1989-06-30

Filing date

1990-06-29

Publication date

1994-07-31

1989-06-30 Priority claimed from HU333589A external-priority patent/HU205896B/hu

1989-06-30 Priority claimed from HU333689A external-priority patent/HU204774B/hu

1990-06-29 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1991-04-15 Publication of IL94914A0 publication Critical patent/IL94914A0/xx

1994-07-31 Publication of IL94914A publication Critical patent/IL94914A/en

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)

IL9491490A 1989-06-30 1990-06-29 Acid separation. IL94914A (en)

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 (en)	1994-07-31

Family

ID=26317626

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9491490A IL94914A (en)	1989-06-30	1990-06-29	Acid separation.

Country Status (10)

Country	Link
US (1)	US5292933A (de)
EP (1)	EP0431121B1 (de)
JP (1)	JPH04500528A (de)
AT (1)	ATE93516T1 (de)
DE (1)	DE69002924T2 (de)
DK (1)	DK0431121T3 (de)
ES (1)	ES2060180T3 (de)
IE (1)	IE62410B1 (de)
IL (1)	IL94914A (de)
WO (1)	WO1991000270A1 (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
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
CA3134427A1 (en) *	2019-03-22	2020-10-01	Tyme, Inc.	D-metyrosine compositions and methods for preparing same
EP3968785A4 (de)	2019-05-14	2023-01-11	Tyme, Inc.	Zusammensetzungen und verfahren zur behandlung von krebs
US10905698B1 (en)	2020-05-14	2021-02-02	Tyme, Inc.	Methods of treating SARS-COV-2 infections
EP4175938A1 (de) *	2020-07-01	2023-05-10	Tyme, Inc.	Kristalline formen von metyrosin

Family Cites Families (8)

* Cited by examiner, † Cited by third party
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 (de) *	1986-07-15	1989-06-21	Nihon Iyakuhin Kogyo Co., Ltd.	Optisch aktives Carbonsäurederivat-l-Lysinsalz und Verfahren zu dessen Herstellung
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 AT AT90909482T patent/ATE93516T1/de not_active IP Right Cessation
- 1990-06-29 WO PCT/HU1990/000045 patent/WO1991000270A1/en not_active Ceased
- 1990-06-29 ES ES90909482T patent/ES2060180T3/es not_active Expired - Lifetime
- 1990-06-29 IE IE236090A patent/IE62410B1/en not_active IP Right Cessation
- 1990-06-29 EP EP90909482A patent/EP0431121B1/de not_active Expired - Lifetime
- 1990-06-29 IL IL9491490A patent/IL94914A/en not_active IP Right Cessation
- 1990-06-29 DE DE90909482T patent/DE69002924T2/de not_active Expired - Fee Related
- 1990-06-29 DK DK90909482.3T patent/DK0431121T3/da active
- 1990-06-29 US US07/684,892 patent/US5292933A/en not_active Expired - Fee Related
- 1990-06-29 JP JP2508964A patent/JPH04500528A/ja active Pending

Also Published As

Publication number	Publication date
DE69002924D1 (en)	1993-09-30
IE902360L (en)	1990-12-30
US5292933A (en)	1994-03-08
DK0431121T3 (da)	1993-10-11
IE902360A1 (en)	1991-06-19
JPH04500528A (ja)	1992-01-30
EP0431121A1 (de)	1991-06-12
DE69002924T2 (de)	1993-12-23
IL94914A0 (en)	1991-04-15
ES2060180T3 (es)	1994-11-16
IE62410B1 (en)	1995-01-25
EP0431121B1 (de)	1993-08-25
WO1991000270A1 (en)	1991-01-10
ATE93516T1 (de)	1993-09-15

Legal Events

Date	Code	Title	Description
1997-03-18	RH	Patent void

Publication	Publication Date	Title
JP2010159292A (ja)	2010-07-22	イミダゾリル化合物の塩酸塩一水和物
EP0298395A1 (de)	1989-01-11	Verfahren zur optischen Spaltung von 2-(6-Methoxy-2-naphtyl)propionsäure
IE69017B1 (en)	1996-07-24	Improved process for resolution of racemic cimaterol (-)-cimaterol and derivatives thereof
JPH02231457A (ja)	1990-09-13	Ｌ―（―）―２―アミノ―３―（３，４―ジヒドロキシフェニル）プロパン酸の合成方法
EP0213785A1 (de)	1987-03-11	Verfahren zur optischen Trennung von DL-Cystein und (R,S)-1-(1-Naphthyl)ethylamin
IL94914A (en)	1994-07-31	Acid separation.
EP0173921B1 (de)	1988-05-18	Verfahren zur Racemisierung einer alpha-Aminocarbonsäure
JPH01135747A (ja)	1989-05-29	光学活性塩、その製法および光学活性３‐クロル‐２‐ヒドロキシプロピルトリメチルアンモニウムクロリドの製法
HU195764B (en)	1988-07-28	Process for production of optically active carnitinenitril-chloride
JPH0135821B2 (de)	1989-07-27
US4325886A (en)	1982-04-20	Optical resolution of acylthiopropionic acid
FR2571366A1 (fr)	1986-04-11	Procede de preparation de la l-carnitine et de ses sels
EP0036265B1 (de)	1986-06-18	Verfahren zur optischen Trennung von (+/-)-2-Amino-1-butanol und/oder (+/-)-mandelsäure
EP0123832B1 (de)	1987-11-19	Verfahren zur optischen Trennung einer Enantiomer-Mischung von Trans-3-((4-Methoxyphenoxy)-Methyl)-1-Methyl-4-Phenyl-Piperidin
US6054594A (en)	2000-04-25	Process for the production of enantiomerically enriched N-acylazetidine-2-carboxylic acids
EP0171616B1 (de)	1989-07-12	Verwendung von alpha-amino-epsilon-caprolactam für die optische Spaltung von N-acetylindolin-2-Karbonsäure und Verfahren zur Herstellung von optisch aktiver N-acetylindolin-2-Karbonsäure
US4411836A (en)	1983-10-25	Racemization of an α-methyl-β-acylthiopropionic acid
JPS6320817B2 (de)	1988-04-30
KR100235374B1 (ko)	1999-12-15	2-아미노나프티리딘 유도체의 광학 이성질체 제조 방법
EP0320898A2 (de)	1989-06-21	Verfahren und Verbindungen zum Auflösen von 1-Methyl-3-phenylpropylamin
JPH09143128A (ja)	1997-06-03	光学活性１−フェニルエチルアミンの製造法
US4230860A (en)	1980-10-28	Processes for the separation of enantiomers by selective crystallization
US4285884A (en)	1981-08-25	Process for resolution of racemic DL-α-aminocarboxylic acids
HU205896B (en)	1992-07-28	Process for resolving treo-3-//2-amino-phenyl/-thio/-2-hydroxy-3-/4-methoxy-phenyl/-propionic acid
JP3663643B2 (ja)	2005-06-22	光学活性１−（２，４−ジクロロフェニル）エチルアミンの製造法