NO135903B - - Google Patents

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Info

Publication number: NO135903B
Authority: NO; Norway
Prior art keywords: penicillamine; norephedrine; formyl; mol; carboxylic acid
Prior art date: 1971-07-30

Application number

NO2163/72A

Other languages

English (en)

Norwegian (no)

Other versions

NO135903C (fi

Inventor

F Asinger

K-H Gluzek

H Offermanns

W Von Bebenburg

Original Assignee

Degussa

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.)

1971-07-30

Filing date

1972-06-16

Publication date

1977-03-14

1972-06-16 Application filed by Degussa filed Critical Degussa

1977-03-14 Publication of NO135903B publication Critical patent/NO135903B/no

1977-06-22 Publication of NO135903C publication Critical patent/NO135903C/no

Links

229960001639 penicillamine Drugs 0.000 claims description 28
DLNKOYKMWOXYQA-CBAPKCEASA-N (-)-norephedrine Chemical compound C[C@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-CBAPKCEASA-N 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 19
VVNCNSJFMMFHPL-UHFFFAOYSA-N penicillamine Chemical compound CC(C)(S)C(N)C(O)=O VVNCNSJFMMFHPL-UHFFFAOYSA-N 0.000 claims description 16
238000000034 method Methods 0.000 claims description 14
230000003287 optical effect Effects 0.000 claims description 5
238000011084 recovery Methods 0.000 claims description 2
239000011833 salt mixture Substances 0.000 claims description 2
VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 claims 2
VVNCNSJFMMFHPL-GSVOUGTGSA-N L-penicillamine Chemical compound CC(C)(S)[C@H](N)C(O)=O VVNCNSJFMMFHPL-GSVOUGTGSA-N 0.000 description 29
238000003776 cleavage reaction Methods 0.000 description 20
230000007017 scission Effects 0.000 description 20
238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 0.000 description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000012452 mother liquor Substances 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
229910052500 inorganic mineral Inorganic materials 0.000 description 6
239000011707 mineral Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
238000010992 reflux Methods 0.000 description 5
150000001413 amino acids Chemical class 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229940049954 penicillin Drugs 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
-1 D,L-penicillamine amine Chemical class 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
206010036030 Polyarthritis Diseases 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000003791 organic solvent mixture Substances 0.000 description 2
229960000395 phenylpropanolamine Drugs 0.000 description 2
239000000047 product Substances 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
125000003396 thiol group Chemical group [H]S* 0.000 description 2
DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 2
239000000052 vinegar Substances 0.000 description 2
235000021419 vinegar Nutrition 0.000 description 2
CZDHUFYOXKHLME-UHFFFAOYSA-N 2-amino-3-methyl-3-sulfanylbutanoic acid;hydron;chloride Chemical compound Cl.CC(C)(S)C(N)C(O)=O CZDHUFYOXKHLME-UHFFFAOYSA-N 0.000 description 1
QEIKJZZSMZXSAI-UHFFFAOYSA-N 3-formyl-2,2,5,5-tetramethyl-1,3-thiazolidine-4-carboxylic acid Chemical compound CC1(C)SC(C)(C)N(C=O)C1C(O)=O QEIKJZZSMZXSAI-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
206010011778 Cystinuria Diseases 0.000 description 1
125000003047 N-acetyl group Chemical group 0.000 description 1
230000006181 N-acylation Effects 0.000 description 1
206010039710 Scleroderma Diseases 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000000729 antidote Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
230000002950 deficient Effects 0.000 description 1
DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
229960002179 ephedrine Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
208000006454 hepatitis Diseases 0.000 description 1
231100000283 hepatitis Toxicity 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
231100000566 intoxication Toxicity 0.000 description 1
230000035987 intoxication Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Tires In General (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Peptides Or Proteins (AREA)

NO2163/72A 1971-07-30 1972-06-16 NO135903C (fi)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2138122A DE2138122C3 (de)	1971-07-30	1971-07-30	Verfahren zur Gewinnung von D-Penicillamin

Publications (2)

Publication Number	Publication Date
NO135903B true NO135903B (fi)	1977-03-14
NO135903C NO135903C (fi)	1977-06-22

Family

ID=5815277

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO2163/72A NO135903C (fi)	1971-07-30	1972-06-16

Country Status (27)

Country	Link
JP (1)	JPS544937B1 (fi)
AR (1)	AR196077A1 (fi)
AT (1)	AT320607B (fi)
AU (1)	AU465833B2 (fi)
BE (1)	BE786964A (fi)
BR (1)	BR7205067D0 (fi)
CA (1)	CA979924A (fi)
CH (1)	CH580044A5 (fi)
CS (1)	CS183662B2 (fi)
DD (1)	DD98093A5 (fi)
DE (1)	DE2138122C3 (fi)
DK (1)	DK145780C (fi)
EG (1)	EG10792A (fi)
ES (1)	ES402609A1 (fi)
FI (1)	FI56527C (fi)
FR (1)	FR2148050B1 (fi)
GB (1)	GB1394855A (fi)
IE (1)	IE36577B1 (fi)
IL (1)	IL39963A (fi)
IT (1)	IT1059660B (fi)
NL (1)	NL165153C (fi)
NO (1)	NO135903C (fi)
RO (1)	RO70841A (fi)
SE (1)	SE383739B (fi)
SU (1)	SU501669A3 (fi)
YU (2)	YU36016B (fi)
ZA (1)	ZA723486B (fi)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1424432A (en) *	1972-03-25	1976-02-11	Degussa	Pharmaceutical compositions
DE2304055C3 (de) *	1973-01-27	1982-04-29	Degussa Ag, 6000 Frankfurt	Verfahren zur Gewinnung von D- Penicillamin
DE2362687C3 (de) *	1973-12-17	1982-01-14	Degussa Ag, 6000 Frankfurt	Verfahren zur Gewinnung der optischen Isomeren des Penicillamins
US4075219A (en) *	1977-03-31	1978-02-21	Eli Lilly And Company	Epimerization process
DE3134106A1 (de) *	1981-08-28	1983-03-17	Degussa Ag, 6000 Frankfurt	Verfahren zur trennung des racemats s-(carboxymethyl)-(r,s)-cystein (b)
DE3134042A1 (de) *	1981-08-28	1983-03-10	Degussa Ag, 6000 Frankfurt	Verfahren zur trennung des racemats s-(carboxymethyl)-(r,s)-cystein (a)

0
- BE BE786964D patent/BE786964A/xx not_active IP Right Cessation
1971
- 1971-07-30 DE DE2138122A patent/DE2138122C3/de not_active Expired
1972
- 1972-05-10 ES ES402609A patent/ES402609A1/es not_active Expired
- 1972-05-16 RO RO7270911A patent/RO70841A/ro unknown
- 1972-05-17 FI FI1403/72A patent/FI56527C/fi active
- 1972-05-22 ZA ZA723486A patent/ZA723486B/xx unknown
- 1972-05-25 DD DD163190A patent/DD98093A5/xx unknown
- 1972-06-06 DK DK280972A patent/DK145780C/da active
- 1972-06-16 NO NO2163/72A patent/NO135903C/no unknown
- 1972-06-20 EG EG269/72A patent/EG10792A/xx active
- 1972-06-22 CS CS7200004425A patent/CS183662B2/cs unknown
- 1972-06-30 NL NL7209189.A patent/NL165153C/xx not_active IP Right Cessation
- 1972-06-30 SU SU1806149A patent/SU501669A3/ru active
- 1972-07-07 YU YU1514/72A patent/YU36016B/xx unknown
- 1972-07-13 GB GB3272672A patent/GB1394855A/en not_active Expired
- 1972-07-17 CH CH1064972A patent/CH580044A5/xx not_active IP Right Cessation
- 1972-07-20 IE IE1016/72A patent/IE36577B1/xx unknown
- 1972-07-21 IL IL39963A patent/IL39963A/xx unknown
- 1972-07-27 AR AR243308A patent/AR196077A1/es active
- 1972-07-27 FR FR7227091A patent/FR2148050B1/fr not_active Expired
- 1972-07-27 AT AT647072A patent/AT320607B/de not_active IP Right Cessation
- 1972-07-28 IT IT51845/72A patent/IT1059660B/it active
- 1972-07-28 CA CA148,203A patent/CA979924A/en not_active Expired
- 1972-07-28 SE SE7209900A patent/SE383739B/xx unknown
- 1972-07-28 AU AU45107/72A patent/AU465833B2/en not_active Expired
- 1972-07-28 BR BR5067/72A patent/BR7205067D0/pt unknown
- 1972-07-31 JP JP7684772A patent/JPS544937B1/ja active Pending
1973
- 1973-10-03 YU YU2593/73A patent/YU36017B/xx unknown

Also Published As

Publication number	Publication date
IE36577B1 (en)	1976-12-08
IE36577L (en)	1973-01-30
AU465833B2 (en)	1975-10-09
FR2148050A1 (fi)	1973-03-11
CA979924A (en)	1975-12-16
SE383739B (sv)	1976-03-29
IL39963A0 (en)	1972-09-28
FR2148050B1 (fi)	1976-01-16
FI56527C (fi)	1980-02-11
NO135903C (fi)	1977-06-22
FI56527B (fi)	1979-10-31
JPS544937B1 (fi)	1979-03-12
ZA723486B (en)	1973-03-28
DK145780C (da)	1983-08-22
DD98093A5 (fi)	1973-06-05
NL7209189A (fi)	1973-02-01
DE2138122B2 (de)	1978-10-05
IL39963A (en)	1975-02-10
NL165153B (nl)	1980-10-15
YU36016B (en)	1981-11-13
YU151472A (en)	1981-02-28
AR196077A1 (es)	1973-11-30
BE786964A (fr)	1973-01-29
BR7205067D0 (pt)	1974-04-25
DE2138122C3 (de)	1979-07-19
EG10792A (en)	1976-11-30
DE2138122A1 (de)	1973-06-07
GB1394855A (en)	1975-05-21
DK145780B (da)	1983-02-28
CS183662B2 (en)	1978-07-31
SU501669A3 (ru)	1976-01-30
NL165153C (nl)	1981-03-16
YU259373A (en)	1981-02-28
AT320607B (de)	1975-02-25
IT1059660B (it)	1982-06-21
AU4510772A (en)	1974-01-31
CH580044A5 (fi)	1976-09-30
RO70841A (ro)	1982-08-17
ES402609A1 (es)	1975-04-16
YU36017B (en)	1981-11-13

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NO135903B (fi)	1977-03-14
CZ285157B6 (cs)	1999-05-12	Způsob čištění 1-[N2-((S)-ethoxykarbonyl)-3-fenylpropyl)-N6-trifluoracetyl]-L-lysyl-L-prolinu
US3062804A (en)	1962-11-06	Peptide synthesis and intermediates therefor
US3980665A (en)	1976-09-14	Optically active salt of protected D-penicillamine and L-lysine
US2867654A (en)	1959-01-06	Acylation of alpha-monoamino carboxylic acids
Harington et al.	1940	Experiments on the biogenesis of vitamin B1
EP0581899A1 (en)	1994-02-09	Improved process for the preparation of 1s-(1r, 2s, 3r*)]-n-(4-(morpholinylsulfonyl)-l-phenylalanyl-3-(2-amino-4-thiazolyl)-n- (1-cyclohexylmethyl)-2,3-dihydroxy-5-methylhexyl]-l-alaninamide
US5359074A (en)	1994-10-25	Process for the preparation of racemic and optically active 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and its precursors
US3966752A (en)	1976-06-29	Resolution of D,L-protected-penicillamine
JP2000516586A (ja)	2000-12-12	３―ピロリン―２―カルボン酸誘導体の製法
EP0159396A2 (en)	1985-10-30	Carboxyalkyl peptide derivatives
US3954783A (en)	1976-05-04	Resolution process and salt of protected D-penicillamine and L-pseudonorephedrine
US3983162A (en)	1976-09-28	Optical resolution of alkyl esters of DL-phenylalanine
US2794025A (en)	1957-05-28	Process of resolving amino acids of the proline type
Benoiton	1968	Conversion of β-chloro-l-alanine to α-carbobenzoxy-dl-diaminopropionic acid
CA1040205A (en)	1978-10-10	Process for the racemate splitting of d,l-penicillamine
JPH082791B2 (ja)	1996-01-17	健忘症治療剤
Cox et al.	2003	The synthesis of some chiral 2-aminoalkyloxazole-4-carboxylates from isoxazol-5 (2H)-ones
JPH0776211B2 (ja)	1995-08-16	ピログルタミン酸誘導体
US3959302A (en)	1976-05-25	Process for the splitting of the racemate of d-1-phenylpropanolamine
JPS625140B2 (fi)	1987-02-03